It was my final year at college back in the early 90’s. I was 22 years old and she was a freshman who had just turned 18. Despite our age difference she had a control over me. Maybe it was the time in my life, confused and a bit scared of my future in "the real world", being in an unfulfilling on again off again relationship for a couple of years, and my new found interest in the fairly young internet and how it opened my eyes to a world where women could dominate men. But maybe I should start at the beginning.
I met Jane at the college radio station where I DJ’ed once a week. It was right before winter break and most of the other DJs cut out early. I was done with exams and just enjoying my free time on campus, so that day I was filling in for what was supposed to be half the day until I found out my replacement also bailed, so it turned into most of the day. My girlfriend was supposed to be there to help out by reading some news and keeping me company, but she let me down as well. Turned out to be the second to last straw in our relationship. The final one was when Jane walked in.
The door to the station is always locked for security, but there was a buzzer on the door and a camera in the studio to see who was there. I was surprised when the buzzer went off. The camera screen was a tiny black and white, but I could tell it was a woman and not an axe wielding maniac. I had just put a song on so had a few minutes so ran to the door to see what she wanted. When I opened the door I was a little taken aback. I couldn’t tell on the monitor but she was tall. I stood just over 5’9 and it looked like she had an inch on me, with a curvy body. Her hair was jet black, with fair skin and blood red lips. She had the goth look down to a tee.
She wanted to start reading news for the station. I'm sure there was some sort of process to go through to start doing this (not that it required a permit or anything), but at the time I needed the help and company, so I briefly showed her what to do and left her to it. It was pretty simple. We had an old teletype that would print out news. She just needed to grab the printouts, skim through, and read on air every 20 minutes or so. My job was equally easy. Pick out songs to play and throw in some PSAs every once in a while. Between the two we had a lot of down time, so during the music we chatted a bit and hit it off quickly. She had a good sense of humor, very similar to mine, a bit twisted and dark. Physically she was just my type.
Finally my replacement showed up and I could leave. Jane could have stayed and kept doing the news, but instead left with me. She suggested we grab a bite at the student center. While we ate our conversation became flirty. Once we were done she asked if she could come back to my dorm room (luckily I had no roommate). Turned out she lives in the same building, two floors above me. We sat in my room for a while and chatted some more. It wasn’t long before we went from flirty to straight up discussing sex. Mainly our past experiences. I’ve always been shy and awkward, a definite late bloomer. I needed a neon sign to let me know if someone was interested in me, and as a result I had only been with a couple of people. Jane, on the other hand, had a lot more experience. Now I’m not one of those guys who thinks women should all be virgins, otherwise they’re sluts. Quite the opposite, but I had to admit our age and experience difference made her quite intimidating to me. Between that and me being the clueless guy I had no idea what her intentions were, until finally she said to me, "You know, I'm really wondering what it would be like to kiss you."
So me still being shy and unwilling to make the first move reply with, "Well, why don't you come here and find out?"
So she did, and naturally one thing led to another, and we had a night of amazing sex. She was insatiable, and damn near wore me out. So for the rest of the week we'd meet and fuck like bunnies, until winter break started and we went our separate ways. We lived too far apart to meet up since neither of us owned a car, so we talked a few times on the phone. Winter break was four weeks long. That first week we only spoke a couple times and just talked. The second was when we started having phone sex and the calls became more frequent. This continued into week three when one night she started asking about my craziest sexual fantasies. Normally I’m hesitant to share them since I’m afraid it will scare people away, but I had just listened to her bring herself to orgasm and had been stroking myself for a half hour and was on the edge of cumming myself. I told her about my new found interest in BDSM, which seemed to really interest her.
“Oh really? Did you cum yet?” she asked.
“No, but I’m really close.”
“Good, slow down and tell me more. Don’t cum until you’ve told me everything, but keep playing with yourself.” My mind was getting hazy with lust so I told her everything. Liking when the woman is in complete control, focusing on her pleasure, enjoying being teased and denied orgasm, liking pain, especially to my balls. She obviously was enjoying what I told because I soon heard her having a second orgasm. It was almost enough to send me over the edge but I let go at the last second forcing my cock to throb fruitlessly in the air as I listened to her heavy breathing slow down. Once she was calmer, “Goddamn that was amazing. You better not have cum, though.”
“No, I didn’t, but I had to stop touching myself when I heard you. It was too much for me.”
“Good boy.” My cock throbbed again when she called me that. “When we get back to school I’m going to make you my sex slave. Would you like that?”
Again I throbbed and thought I was going to cum without even touching myself. I managed to choke out, “Yes, I’d like that very much.”
“Good. I’m going to have so much fun with you! For now, stop touching yourself and don’t cum. I’ll call you tomorrow. Good night, sweet boy.” Just like that she was gone and all I heard was the dial tone. It took me a few seconds to realize what was happening and hang up the phone. Was this really happening? This already seemed too good to be true because the sex was so good, but now she’s going to make my fantasies a reality? Between my sudden blue balls and these thoughts, it took me a long time to fall asleep that night.
The rest of the week became a routine. She’d call me late and probe me for new ideas and tell me some of her own. At some point I’d hear her cum, sometimes twice. And of course during the entire time I had to keep stroking myself but refrain from finishing. Each night was getting more difficult to hold back, and each day was more tempting to cheat and give myself some relief. After all, she’d never know. I was still young enough to get horny at a moment’s notice the next time I talked to her, but always decided against it. After all, what was the point of having this type of relationship if I was just trying to please myself?
Finally the break was over, and for the first time I couldn’t wait to get back to school. Sunday was the first day we were allowed back in the dorms and we both arranged to get back as early as we could. Once I was back I hurriedly unpacked, anxious to call Jane. As I reached for the phone there was a knock at my door. I opened and there she was, smiling and looking amazing. Without a word she put her hand on my chest and pushed me inside, locking the door behind her. Needless to say, we were both horny as hell (though I’m guessing I was more than her) and quickly ended up naked on my bed. After teasing me all week, I was hoping we would have a day long marathon of mind-blowing sex. And that’s exactly what we had, though not exactly how I was hoping. She made it clear right away that she was the focus and I was still going to wait for my own pleasure. I spent the entire day focused on pleasing her. My world was between her legs using my hands, mouth, and cock to make her cum as many times as she wanted, and she wanted a lot! It wasn’t until around 6pm when she decided we should take a break for dinner. Most of me was glad, except for my penis, of course. It was red and angry and needed some attention, but the rest of me was exhausted.
After a quick bite in the cafeteria, she dragged me back to my room for round two. This time the focus was on me. After stripping me down, she pushed me on my back and told me to just relax. She was still fully clothed, kneeling between my legs, and gently massaging my quickly hardening cock. She spent a long time very slowly and gently playing with me. It took longer than I thought it would in my current state, but I could feel my orgasm approaching. I thought to myself that this has to be it. After a week and everything we did today, no way she makes me go longer. As I get closer, my moans get louder. “You better get my permission before you even think about cumming. And only ask me when you’re right on the very edge. Got it?”
“Yes, ma’am,” I gasp in reply. I’m now convinced this is finally it, which only propels me closer. Only a minute or two later, “Oh god, please Jane, I’m so close, can I please cum now? Please?!” Instead of answering, her movements became even slower, and then stopped. Wordlessly, she got off the bed and kicked off her shoes, leaving me bobbing and throbbing. She grabbed a glass of water and took a drink. She then came back to bed and took the same position.
“Don’t forget, ask permission.” Instead of stroking, she treated me like a lollipop, licking me up and down, concentrating on the head and sensitive underside. It wasn’t long before I was pleading to cum again, but like before she abandoned me, got up and removed her socks. Once she was back in position it dawned on me her new game. Each edge she removed an article of clothing. I only hope once she’s nude she lets me ravage her. She took me fully in her mouth, I begged for permission, her top came off. Back to stroking, this time firm and steady while she rhythmically squeezed my balls, more pleading, there go her jeans. Back to her mouth, deep throating me, begging, no more bra. With her breasts free, she wrapped them around my cock and stroked me. My begging became more pathetic, but of course she stopped and got up again to remove her panties. Standing next to the bed, completely nude, she paused for a moment to watch me plead for release. She licked her lips as she slowly climbed back into bed and on top of me, putting me inside of her and gradually lowering herself until my cock completely disappeared.
“Remember, sweet boy, no cumming until I say and keep still. Let me take care of you. I’ll do all the work.” Once again her movements were excruciatingly slow. She took her time riding me. Stopping anytime I moved my hips even an inch. I could feel my long overdue orgasm approaching. This has to be it. As crazy as she made me, I had to admit this was going to be worth it. Once again I begged for permission and in response she settled on top of me, still deep inside, and started rubbing her clit, again ordering me not to move. Helplessly, I watched as she brought herself to orgasm. I felt her pussy spasm and clench around me, but it’s not enough to tip me over, only keep me riding the edge.
She stays still, eyes closed, content smile on her lips. I couldn’t wait any longer, “Um, Jane, may I please cum now? Please?”
Her eyes snapped open. “Tsk tsk tsk. Silly boy, you went and ruined it.” She got off of me and got out of bed, put on my robe and left the room, I assumed to go use the community bathroom since my room only has a sink. What just happened? I just laid there in shock until she returned. “Well, it’s getting late. We should probably get some sleep.”
“But Jane, I thought...”
“Hush. You said you wanted to be my sex slave, right?” I nodded. “And what’s the job of my sex slave?”
“Um, to please you?”
“That’s right. And if I choose to reward you for pleasing me that’s my decision. You did a really good job tonight, and I was seriously considering rewarding you, but then you got selfish and interrupted my relaxation after that wonderful orgasm. So now we go to bed. I’m too tired to punish you, I’ll think of something tomorrow.” She grabbed my toothbrush and started brushing her teeth.
That finally broke me. I got out of bed, crawled over to her, and started kissing her feet begging for forgiveness, “Please, Jane, please! I’m so sorry, I just couldn’t take anymore and lost my head!” I went on blubbering and kissing as she continued to finish brushing her teeth.
Once she was done rinsing, she leaned down and lifted my head up by my chin with one hand and hushed my lips with the other, “Ssshhhhh. There there. Did I go and break my new toy already?” I could only nod. “Poor thing, but isn’t this exactly what you wanted?” I nodded again. “Is it too much for you? Do you want to stop?”
“I didn’t expect you to be so into it right away and make it so intense. It’s so much more than I expected, but no, I don’t want to stop.”
“Are you sure? Tell you what, I’ll give you a choice right now. No more being my slave and I’ll fuck your brains out until your balls are empty right now. But then that’s it. We go back to normal, awesome sex and no more talk about teasing and torture.”
As tempting as that was, especially after everything we did today, I knew I’d regret it for the rest of my life. “No, please keep me as your slave. I’m sorry for being so selfish.”
“That’s my sweet boy. I forgive you, but you’ll still need to be punished…tomorrow.” She removed the robe and draped it over my head, “There, go get yourself ready for bed and join me.” As she got into bed, I got up, put on the robe and brushed my teeth, allowing the last of my erection to fade before going down the hall to use the bathroom myself. When I came back Jane was already snuggled under the covers. She watched me drop the robe and climb into bed with her. She positioned us so we were spooning, but she was the big spoon and whispered in my ear, “While you were gone I was thinking, and maybe I am going a little overboard right now.” She grabbed my soft cock and quickly massaged it back to hardness, “We should gradually work you up, so just relax but you still need to ask permission, got it slave?”
“Yes, ma’am!” I was ecstatic. I laid on my side, enjoying the feeling of her body pressed against mine. Her breasts pushed against my back. Her hand once again pushing me closer and closer to orgasm. This has to be it, no way would she be this cruel, especially after the break down I just had. Here it was, the moment of truth, “Please, please please, Mistress Jane, please may I cum?”
Her hand stopped and just held me, “Oooohhh, I like the sound of that. Always call me Mistress from now on, understood?”
“Yes, Mistress.”
“Good boy, now roll over and face me.” I obey and she kisses me deeply. We made out for a few minutes while her hand stayed on my cock, moving just enough to keep me on edge. “But what kind of mistress would I be if I gave in so easily? Time for bed.” Before I could say or do anything, she rolled away from me so now I was the big spoon. She made sure to position my cock so it was wedged between her butt cheeks and pulled my free arm around her and rested my hand on one of her breasts.
I was stunned, but managed to whisper, “Thank you, Mistress.” She sighed contentedly and quickly fell asleep in my arms. It was another hour before I finally calmed enough to fall asleep as well, and even then it was restless. At some point I must have finally gone under, but soon awoke to her forcefully stroking my already hard and sore cock. I wanted to either stop her or beg to cum, but before I could do either she climbed on top of me and quickly had me inside her. Fortunately, she only wanted a quickie. Once she was finished, I suggested we get something to eat and get out for a bit. I was hungry, but mainly wanted to get a break from the teasing and give my body a chance to recharge before getting to my first class. Fortunately for me my last semester was pretty light, but I still had to get through them all and graduate, no matter how distracted I might be getting.
She went back to her room to clean up and I did the same with a quick, cold shower. We met up again for a late breakfast. As we ate I felt like a complete mess and in a total daze between the exhaustion and lust clouding my mind. Jane, on the other hand, looked completely relaxed and chipper. She was beaming, “Last night was amazing! I should have found a sex slave sooner! How are you doing this morning?”
I sighed a little deeper than I intended, “Yesterday was great. You were everything I’ve always dreamed about, but I’m so tired right now. I barely slept last night, and you’ve got me so worked up I’m having a hard time thinking straight. Sorry, I probably sound ungrateful, just being honest. I could just really use a nap.”
“Well, what good is a slave if he’s too tired to work? Ok, tell you what. Once you’re done for the day, take a nap and call me as soon as you wake up. By the way, what is your schedule?” I managed to get myself a pretty sweet schedule. I only had four classes this semester, and two of them were blow-off classes. Ones I didn’t need, but sounded interesting and, most importantly, easy. I scheduled them two each day starting at 11am and done by 2pm. At the time my goal was to coast to the finish line, but I had no idea I’d find someone like Jane to make things more complex. After telling her some of this she looked at her watch and realized we’d be late and had to go, so we went our separate ways.
I breeze through my first class and head towards my second and am surprised to find Jane waiting for me outside the building. Before I can say anything, she grabs my hand and pulls me inside. She directs me down a deserted hall and stops us in front of a door. After a quick look around to ensure no one sees us, she opens it and pushes me inside. It’s a small utility closet, barely bigger than an old phone booth. She presses against me, forcing me into the back wall, giving me a big kiss while her hands undo my belt and pants, freeing my quickly stiffening cock. She suddenly breaks the kiss, lowers her own jeans and panties, turns away from me and bends at the waist, bracing herself on the closet’s door frame, “Hurry up, we only have a few minutes!” Not needing to be told twice, I grab her hips, swiftly enter her, and start thrusting while she rubs her clit. I manage to hold out long enough for her to orgasm yet again at my expense. Next thing I know her pants are back up, she gives me a quick kiss and says, “What a sweet boy,” and is gone, leaving me alone in the closet with my pants around my ankles and a raging erection.
Realizing I’m about to be late I pull my pants up, adjust myself as best as I can, and hurry to my class, keeping my backpack in front of me the entire way. Luckily this one was a simple introductory with minimal reading due before next time. I head back to my room for a much deserved nap, keeping my eyes open for another Jane trap. I’m unsure if I’m more relieved or disappointed that I never saw her. Once back in my room I’m asleep before my head hits the pillow.
My dreams are a jumbled mess with one common theme: sex! Several women are pleasuring me, sometimes Jane, sometimes a celebrity I have a crush on. One is stroking me, the other sucking me. My orgasm builds and just when I’m finally going to explode I wake up to my phone ringing. Groggily, I answer, “Hello?”
“Hello, sleepy slave. I thought you might have forgotten about me.”
Looking around my room I ask, “What time is it?”
She laughs, “It’s a little after 6 and I’m hungry. Come get me and we’ll have some dinner at the student center, then we can play some pool or something. Don’t keep me waiting too long!” and she hung up. I gently shook my head to help clear it, turned on the lights and started putting myself back together. Naturally, I was still hard from my almost wet dream. Ignoring it I splashed some water on my face and brushed my teeth. I still looked a mess and was about to throw a hat on and go, but figured I should put in some effort so basically dunked my head in the sink to both help me wake up and make my hair look less like a hobo.
Once satisfied I did a quick clothes change and left my room. I bounded up the two flights of stairs and was standing in front of her door knocking. As it opened I was a little surprised to find someone else. Physically, she was the complete opposite of Jane. Short, 5’2” tops, and very trim and toned, with shoulder length brown hair. She was really attractive, but not the kind of girl I normally went for. I assumed it was her roommate, Heather, whom I hadn’t met yet but only heard about. She asked, “So are you Jane’s slave boy?”
I blushed, looked down, and could only meekly reply, “Yeah…”
She looked at her watch and said, “Damn,” turned back to the room, “You’re right, you really have him whipped. He got here in less than 5 minutes, guess dinner’s on me.” Turning back towards me she lowers her voice, “I hope she makes you wait all month!” My eyes go wide as my face burns redder. Just how much has Jane told her?
Before I could say anything Jane appears at the door dressed in simple sweatpants and a loose fitting shirt, “There’s my sweet boy. Ok, let’s go, I’m famished! Looks like you met my roommate, Heather. Hope you don’t mind, but I invited her to join us, but good news! Since you were so quick to get here, she’s buying!”
“Hey! I never said I’d buy him dinner too! That’s not fair, I’m sure if I won you would have had him pay.”
Jane shook her head, “Nope. My poor slave has been through a lot. I figure a free meal is the least I could do. A bet’s a bet!”
Heather glared at me, “Fine.” Wow, she really seemed to hate me. No idea why, was the bet that important to her? It’s not like she’s spending any money. When you live on campus you have a food plan and points for the whole semester. It’s really not a big deal. I hope Jane doesn’t take advice from her or else I could be suffering for a long time.
Jane holds my hand as we all take the short walk to the student center. Our campus is pretty small, so everything is a short walk. It feels like we’re a normal couple. So far everything has just been about sex. Neither of us have discussed anything else when it comes to our relationship, so who knows where this will lead. For now, I’m just enjoying fulfilling my fantasies. Once at the student center we get in line. I’m the only one who grabbed a tray, I was confused why the girls didn’t until they started piling their food onto mine. Heather gives me another dirty look as she hands over her ID to pay for everything. I follow Jane, carrying the heavy tray, to a table. As soon as I sit down Heather delivers a line like a classic bad actress, “Oh no, I forgot a fork and knife. Jane, can you have your slave fetch them for me?” She looks at me with a big shit eating grin.
I look to Jane, she nods, “Would you please? That’s my sweet boy.” So I quietly get up and grab them for her, also getting a spoon just in case.
Just as I sit down, Heather again gives a badly acted line, “Oh jeez, forgot a napkin too. Can you…”
But this time Jane cuts her off, “Okay, now you’re just being a bitch. Get your own toy to boss around or get your own damn napkin.” Heather once again gives me a death star as she gets up to grab whatever else she “forgot.”
Quickly I ask Jane, “Why does Heather hate me so much? I never even met her before. Did that silly bet mean that much to her?”
Jane sighed, “No, it’s not you specifically. Over winter break she found out her boyfriend back home cheated on her. Like, a lot. So she’s pretty pissed at everything right now, especially boys. That and I think she’s a little jealous I found you. So don’t take it personally. Don’t worry, I’ll protect you from my big bad roommate!” After Heather got back the conversation became more ordinary and I relaxed a bit. I guess I was making a good impression because she seemed to soften a little. She was even laughing at some of my jokes! Once we were done Jane wanted to play some pool. Our student center had a decent game area with six pool tables and a good sized arcade. I worked there for my first few years at college so was able to get us a table for free. Since there were three of us we played a game called cut throat. Each player has five balls and the goal was to sink the other player’s balls before they got yours. Once your balls were gone you were eliminated. Since I could always play for free I got pretty good over the years. Jane wasn’t too great a player and Heather was decent, but I was just a little better than her so won the first three games. I didn’t think I was being cocky, but Heather was getting annoyed with me again, “Ok big shot, how about next game we make things a little more interesting?”
I saw Jane roll her eyes, “Okay, Heather, what do you want to play for? Dinner again?”
“No, better than that. I know slave boy here wants to cum if he wins, right?” I turned bright red again, looking around to see if anyone was listening. Both the girls laughed at my reaction.
“Yeah, he probably does, but what if I don’t want him to yet?” Jane asked.
“Well then don’t let him win! What do you want?”
Jane thought for a moment, “Alright, if I win then you have to be my slave girl for a weekend and you can both serve me.” I was not expecting that and it caused a stirring in my pants.
Heather just smiled, “Fine, but if I win then you let me give your slave boy his punishment tonight.” The stirring became greater, causing me to adjust, hoping no one noticed.
Jane furrowed her brow, “Only if I’m there too. I’m not going to let you break him. He’s still new.”
“Don’t you trust me? I’m hurt.”
“You’ll get over it.” Jane turned to me, “Be a sweet boy and rack them.” So I guess this is happening. I’m pretty excited. I’m fairly confident I’ll win again, but part of me wants to ensure Jane wins so I can see Heather be put in her place. The game definitely got more interesting. Jane made sure to lean forward on the table whenever I went to shoot. Her top was so loose it gave me a perfect view of her ample cleavage. Heather would describe all the things she planned on doing to me, in graphic detail. I played almost the entire game with a raging erection, and they both noticed and relished in telling me about it. Any thoughts of letting Jane win washed away as I was barely able to stay alive. It came down to one ball left for each of us. Fortunately for me, they both passed up easier shots on each other to try and take me out, and they missed. It set me up for a pair of simple shots. First Jane’s and then Heather’s. I won! I was finally going to cum tonight! I thought I was going to rip my cheeks from smiling so hard.
Heather did not like that, “Double or nothing!”
Jane was confused, “How the hell are you going to do that?”
She first turned to me, “Iif you win again, then I’ll join you guys in a threesome and make you cum as many times as you want tonight.” I almost came right then at the idea.
I finally found my voice, “But if either of you win then nothing?”
Heather rolled her eyes, “Duh, yeah. That’s why it’s called double or nothing.” I was skeptical. I barely won last time and would be insane to pass up my hard earned orgasm.
I was about to decline but Jane chimed in, “C’mon, that sounds like fun. Imagine having both of us touching you.”
Heather added, ‘And sucking you.”
Back to Jane, “Maybe even fucking you. Wouldn’t you like that?”
My head was swimming, I was about to agree but Heather piled on assuming I was still in doubt, “Fine, tell you what. If you win you get a threesome tonight and another day at Jane’s choosing, and if Jane wins then I’ll join you guys as a slave for a week, but if I win then I still get to help punish you tonight. Sound fair?”
That I couldn’t turn down. As blue and aching as my balls were, every guy’s fantasy is a threesome with two women, and she’s guaranteed it’ll happen twice! And if Jane wins, who knows what she’d have us do during a week. I agree to her terms. On the break, I sank one of Jane’s, then managed to pocket a couple of Heather’s before I missed. I’m feeling pretty good about my chances until Heather goes on an incredible run taking out a pair of Jane’s balls and four of mine! She misses my last one but sets up Jane for an easy shot. I look to her with pleading eyes, she blows me a kiss in response and sinks me. “Sorry!” Her apology was not convincing. She takes out one more, but then gives way to Heather who cleans up the rest and wins.
I felt sick to my stomach. Can’t believe I lost the chance at having both of them. Even worse, I’m going to have to wait at least another day before I can cum again. Maybe even longer! To top it all off, I’m now at the mercy of a girl with severe anger issues towards men right now. Heather is all smiles. Jane is just shaking her head. I’m desperate and I blurt out, “Don’t I get a double or nothing chance?”
Jane laughs, but Heather has an evil grin. Like a cat playing with a mouse, but I’m too dumb to notice, “I dunno, I already got what I wanted. How could you possibly make this better for me?”
I hadn’t really thought it through. I quickly rack my brains and come up with a terrible idea, “Well sure, but look how late it is already. Do you have any classes on Wednesdays?”
She looks at me cautiously, “No.”
“Me either. How about instead of tonight, you have all of Wednesday. If Jane’s okay with it.”
Jane could only chuckle again, “You two are being ridiculous. Sure, but on two conditions. This is the last game no matter who wins, like you said it’s getting late. And second, if I manage to win then Heather is my slave for a month!”
Heather didn’t seem too worried about that, “Fine with me,” looking back towards me, “But if you win then you just get your orgasm, no threesomes.”
At this point, I couldn’t push my luck, “Deal.” I hadn’t planned on Jane upping it to a month! I just wanted to get out of Heather punishing me and get my orgasm back, but now I’m having thoughts of somehow getting Jane to win. A whole month with Heather serving beside me is too good to pass up. I do my best to sink Heather’s balls or at least set Jane up for easy shots. It was starting to work but Heather picked up on my plan pretty quickly and took out the rest of Jane’s balls.
“Nice try, you little perv.” We were down to one ball each and it was my turn. It was a tough shot, but one I knew I could make. Just as I was about to shoot Heather upped the ante, “Tell you what, make this shot and the threesome is back on the table.”
I was confused, “And if I miss? What’s the catch?”
She shook her head as she walked over to me, “No catch. You’ve impressed me with your playing.” She got very close to me, “Besides, the three of us could have a lot of fun.” She started whispering in my ear, “And Jane tells me you have a real nice cock and I’d love a good fucking. Now go ahead and shoot!” My erection is back with a vengeance. I gulp and try to calm myself to make the shot. Predictably, I miss. Terribly. Of course Heather doesn’t. “Oh well, too bad. See you Wednesday!” And just like that she left us.
I walked over to Jane, dumbstruck. “You’re not going to let her do this, are you?”
“Hey, you’re the one who doubled down. Don’t worry, I’ll make sure she plays fair, and I’ll be there the whole time. But we can talk about it tomorrow. Right now I need to get you back to your room and dish out my own punishment!”
“What? But Heather…”
She cut me off, “Heather gets you on Wednesday. That doesn’t mean you get out of it from me. You earned it with your selfish behavior last night. Don’t try and weasel out now, you’ll only make it worse.”
Defeated, I simply replied, “Yes, Mistress,” as I collected the pool equipment to return and we headed back to the dorms.
Once again we held hands as we slowly walked back to my room. “You know I don’t have classes Wednesday either. It’s a shame you let her goad you into that dumb bet. I had some great plans for us.” She leaned closer to me, “You were finally going to get to cum, you know. I was going to recreate everything we did yesterday and see how many times I could make you cum in a day.” I audibly whined when she said that. “Maybe we’ll try some other day, I dunno.” I’m guessing she’s just making this up to tease me, but it has the desired effect and I’m devastated. “Oh well, I’m sure you’ll have fun anyway. You told me how much you like pain and being tortured. I think the term you used on the phone was ‘pain slut,’ right?”
Jesus, did I say that? Our phone sex calls were so hot I got caught up in the moment. I can’t even remember exactly what I told her. Quietly, I reply, “Yes, Mistress.”
“Good. Tonight will be a good test for us. We can see what we both enjoy and how much you can take. I’ll need to give Heather some clear boundaries so she doesn’t hurt you in the bad way.” We’re quiet the rest of the way. I assume she wanted that last comment to fill me with dread, and it worked! As soon as we’re in my room and the door’s closed, she locks it and commands, “Take off your clothes. New rule, slaves should never be clothed when we’re alone, got it?”
I quickly strip down, “Yes, Mistress.”
“Good, if I have to remind you in the future then you’ll be punished.” She walked over to my desk, slipping off her shoes, sweat pants, and top revealing her long legs clad in pantyhose and a lacy push-up bra. That explains all the cleavage I saw playing pool. She turned on my stereo a bit louder than normal and sat in my desk chair, “Come over here and lay across my lap. I’ve been wanting to turn your cute butt red for a week now.” The sight of her and knowing what was next caused my cock to rise yet again as I obeyed. She positioned me on her lap so my cock was between her legs as she closed them, trapping it in a silky embrace. She’d occasionally rub her legs together causing me to gasp in pleasure as she rubbed a hand on my behind. I was getting lost in the sensations until a sudden smack rocked me back to reality. She followed with another and another. Slow and steady she spanked my bottom, telling me what a bad slave I was and how I deserved this. After a couple minutes I understood why she made the music so loud. Between the smacks and now my cries of pain, she didn’t want the people in the next room to hear. My ass was getting very sore, the pain was almost unbearable. Mercifully, she stopped. At least I thought it was out of mercy, “My hand’s starting to hurt a little. That’s no fun.” I hear her rummaging through my desk drawer, “Aha! This should work.” The next hit made me yell pretty loud, both out of surprise and pain. “You better keep it down or I’ll have to gag you.” I glance over my shoulder and see she grabbed my wooden ruler and is bringing it down again. I close my eyes, grit my teeth, and try to bear the onslaught as best I can.
My ass feels like it’s on fire. Even my erection has faded. When I feel I couldn’t take anymore I beg, “Please, please Mistress, no more! Please! Mercy! I’m sorry for being bad, please stop!” She lets me go on like this for several more hits before finally stopping.
“Fine, show me how sorry you are.” I froze for a second not knowing what she meant. “I guess you need a few more smacks for motivation.” That broke my paralysis as I scrambled off her lap and onto the floor and began kissing her feet like I did last night. I heard her sigh contentedly, “That’s a sweet boy. Show your Mistress how sorry you are.” I spend several minutes worshipping each stocking-clad foot, then I move to each ankle. Not sensing any resistance I work up to her calves. I keep the same methodical pace as I go to her knees, then thighs as she spreads her legs wide for me. Slow and teasing I work my way to the center to kiss and lick her through the pantyhose. Between her moans of pleasure she keeps calling me a good boy and her sweet boy until she screams out in climax.
She pushes my head away as she comes down, “You dirty boy, trying to distract me. We’re not done yet. Stand up facing away from me with your hands behind your back.” I quickly obey and hear her going through my desk drawer again. I feel cold metal going around my wrists and the unmistakable sound of my handcuffs locking in place. I had told her about them during our winter break sex calls, and she must have found them when she got the ruler. “Turn around.” I spin so my returned erection is pointing right at her. She takes one hand and gently fondles it, lifting it up so her other hand could get a very firm grip of my balls. She squeezes, gently at first, but her grip getting stronger by the second. “Just so you know I do forgive you for last night, but now I’m mad you ruined Wednesday!” Tighter and tighter she squeezes, I can’t move her hands or get away, I can only dance a little in place. “I had such fun plans for us! You would have been begging me to stop making you cum!” She pulled me closer to her and quickly sucked on the head of my cock for a few seconds before letting it pop out, “But you had to get cocky and now Heather is going to make what I’m doing tonight look like a day at the beach.” She releases her death grip and I start to catch my breath until her hand slaps down on the head of my cock. Still rock hard, it bobs up and down. She repeats this a few more times, stinging the sensitive head and then resumes squeezing my balls. She goes through this cycle a couple more times, verbally taunting and teasing me all the while.
“This is getting boring, turn around.” I do and she removes the cuffs, “Now lay down on the bed, face up.” Again I comply and am rewarded with her removing her bra and climbing on top of me so her bare breasts are dangling above my face. “Deep breath now.” I give a confused look before I realize what she intended as she lowers her breasts onto my face, squeezing them together to create a seal over my nose and mouth, smothering me. She holds me in place as I try to move my head and get a breath. She finally lifts up and I gulp down air. “So what do you like better, slave, my breasts or torture?”
Still oblivious I answer the obvious question, “Your breasts, Mistress.”
She smiles, “If you insist!” And again she cuts off my air, longer this time. Once again she allows me a breath and asks, “Breast or torture?” I’m finally wise to the game but would rather have her gorgeous breasts on my face than more pain inflicted on my body right now, even if it means I can’t breathe. Not to mention the fact that my erection is “trapped” between my body and hers, and I’m enjoying the sensations. Fortunately, I got a deeper breath this time. The only problem is she’s laying on me even longer. Another break and some air, same question, same answer. She keeps repeating this routine, lingering on my face more each time. I’m not sure how much more I can take. My lungs are starting to burn and I’m getting a little light headed. After maybe the tenth time (I honestly lost track) I finally relent and say torture between panting breaths. “Hmm, not sure I believe you.” Back on my face. This time my struggle is real, but her leverage is too great and I’m starting to feel weak. When she finally releases me, I do my best to convince her.
“Please, Mistress, please torture me! Spank me! Whip me! Punish me for being bad!”
She laughs at my pathetic display, “Well okay, if that’s what you really want. Roll over on your stomach and grab the bed frame at the head of your bed. Don’t let go no matter what!” I do as she says while she grabs the ruler from my desk and quickly brings it down on my bottom again. I’m still very sore from earlier so this new onslaught is immediately unbearable, but she gives me no choice as she continues to rain down the blows. As my cries get louder she commands me to put my face in the pillow to muffle them, and of course I obey. After a few more minutes of tearing into me she has me roll over again, but still grabbing the bed frame above my head. Thankfully, she puts the ruler down and sits at the foot of the bed, between my legs. With one hand she gets a good grip of my balls and with the other gives them a good, hard slap. I yelp in surprise before Jane tells me to stay quiet as she continues her slaps. I’m able to hold it together for a little while now that I know what’s coming, but soon that becomes too much as well and I can’t help but cry out and beg for her to stop. She sighs and stops, releasing my balls from her grip, but it isn’t out of mercy. Instead she climbs to the head of the bed, turns, and sits her shapely ass right on my face, muffling out any sound as she resumes her assault. The pain is intense and I can’t help but scream and beg into her ass, only to be ignored.
I completely lost track of time. My mind started to float a bit, between the pain endorphins and the lack of oxygen, I was in another world. I almost didn’t notice she stopped. Not only that, but she was gently stroking my somehow still hard cock. The stroking became more firm and quick, bringing me back into the moment, and more importantly, closer to orgasm. I figured this had to be it, after everything she’s made me endure, surely I deserved it by now? No matter what, I knew enough not to expect anything, and because of that I wasn’t disappointed when she stopped and climbed off of me. I gasped for air as I watched her walk to my desk and write something down. Turning back to me, “I have a proposition for you, slave, if you’re interested. I just wrote down a number. It could be one or fifty or even more! I’m going to grab your balls again and punch them. If you want me to stop, just say mercy. If you take more than the number I wrote I’ll make you cum any way you want. If not, then you have to wait. Ready?
Looks like I had little choice, but once again it’s an opportunity I couldn’t afford to pass up, “Yes, Mistress.”
She smiled widely, “Great. Good luck!” She sat between my legs again, got a good grip and slammed her fist into my balls. I howled in pain. She sighed again and had me put my pillow over my face. After several seconds she punched me again, and again. I tried to keep count, thinking I would hold out for ten and then give in. Ten finally came, I was about to give in but thought I should take one more just to be sure, so said nothing. Number eleven felt especially hard and I was done. Taking the pillow off my face I cried mercy. She was still all smiles, “Now let’s see how you did!” She went back to my desk and brought the paper over for me to see. The number eleven was written on it. I was ecstatic, I did it! She saw my reaction and seemed a bit confused, then it dawned on her, “Oh you poor boy. I said more than the number I wrote. If only you took one more, but oh well. Maybe next time.”
I was heartbroken. Not again. For a split second I wanted to end this game, but as I watched her strip out of her pantyhose and climb into bed with me, those thoughts vanished. We wrapped our arms around each other and she was very kind and tender with me, asking how I felt. Checking to make sure she didn’t go too far or seriously hurt me. I just held her, thinking about what happened and how I felt about it. After a few moments I assured her I was good. That I actually enjoyed everything we did. How I could have taken more if she wanted, though I’d probably need to be tied down and gagged. We wound up talking long into the night. Discussing things we should have before we even started down this path. Establishing more boundaries and a safeword. We were so young and horny we dove in too fast, but the upcoming day with Heather had us both thinking in more practical terms. Once both our minds were at ease, we made out for a little bit before drifting off to sleep.
The next day was uneventful. Jane had a pretty full schedule of classes and wanted to give me a chance to recover anyway. Plus she planned on going out to some all ages club that night with her girlfriends. Classes for me were simple again, so I took advantage of the time to relax and catch up on any reading. After dinner, I was in my room playing Nintendo when there was a knock at the door. It was Jane and she looked fantastic! She wore a black corset dress which accentuated her cleavage. Her stocking legs ended in knee high platform boots that made her tower over me in my bare feet. Her pretty face was all made up with dark eye make-up and ruby red lips. I was speechless so she invited herself in. As soon as the door was closed I started removing my clothes. At first because I wanted to throw her on my bed but then I remembered her new rule. “Good boy, you remembered! I’m about to go out but I had something I wanted you to do for me.”
The thought of her going out looking like that without me made me a bit jealous, “Wouldn’t you rather I went with you?”
She smiled, “That would be nice, but tonight is just us girls. Don’t worry, I’m going to come right here when we get back. You’re the only slave for me. But while I‘m gone I want you to stroke yourself for me. I want you super horny and ready for me when I get back, understand?”
I’m disappointed but reply, “Yes, Mistress.”
“Good. So here’s what you’re going to do. You’ll SLOWLY stroke yourself one hundred times. Once you reach one hundred I want you to go as fast and hard as you can until you’re right on the edge and then stop. Take a few deep breaths, relax for a few minutes, then do it all again. Keep repeating that until I get back. I want you to show your self-control and devotion to me. Think you can handle that?”
NO! But I lie, “Yes, Mistress.”
“That’s my sweet boy. Watch some TV while you do it so you’re not bored. We usually stay out pretty late, but I’m going to try and get back earlier than usual. Still probably won’t be until after midnight. Oh, and keep track of how many times you edge, okay babe?”
“Okay, have a good time.”
She winks, “You too!” And then she’s gone. I locked the door behind her, turned on the TV, and laid in bed to start my “assignment.” Looking at my clock, I sighed. It was just after 9pm. I’m going to be teasing myself for at least three hours! I could easily cheat and go back to my Nintendo. Hell, I could even get myself off a few times! There’s nothing stopping me except for my desire to please Jane and be a good slave for her. So instead of doing the normal and rational thing that any early twenties man would do, I instead follow her instructions to the letter. Very slowly and methodically I stroke myself one hundred times. Dragging it out as long as I can for fear of hitting the edge too soon and having to stop, ruining her game. Once I reach a hundred it doesn’t take me long to get to the edge, but it does take all of my will power to stop myself from going over. I want it so bad, I need it so bad, but I want to please her even more, so I stop. I take several deep breaths and calm down, make a check mark on a piece of paper like a prison inmate counting the days and prepare to do it all over again. I try to focus on the TV to make it easier, like the old stereotype of guys thinking about baseball to last longer during sex. I manage to drag it out so it takes around fifteen minutes for each set including my rest period. If I mathed correctly, that’ll put me at approximately twelve to fifteen edges by the time she comes back. Hope she wasn't counting on more. The fact that she wants me to track it must mean something.
Even though I established a good routine, I’m still tempted to not stop at the end of each round. It gets more and more difficult to stop every time. At around twelve thirty I have a new dilemma...I really have to pee! I finish my latest set and take a long break until I’m “calm” enough to put on some clothes and head down the hall to the communal bathroom. I’m sure this wasn’t part of her plan, but nature calls. As I’m walking back to my room I hear my phone ringing! Oh shit, is Jane back? I scramble into the room and quickly grab the phone, “Hello?”
“There you are! What took so long, you weren’t cheating were you?”
I started to panic, “What? No, I had to use the bathroom, I just…”
“Settle down, you’re fine. So how many edges did you do for me?” Took a quick look at my count and was surprised to see I had seventeen. “Hmmm, okay. I’m guessing you’re dressed and relatively calm, so come up to my room.” And she was gone. I was only dressed in a t-shirt and sweatpants, but figured that would be fine. I did decide to brush my teeth and make my best attempt to be more presentable and went up to her room. I knocked and was surprised when Heather answered wearing what looked like pajama pants and a long sleeve t-shirt. She told me to come in and sit down on her chair.
I was surprised that Jane wasn’t there, before I could say anything she said, “Okay, so this is weird. When we made the bet it was stupid and I didn’t expect to win. I was just messing around with you guys and had no intention of doing anything with you. You probably noticed I’m pretty competitive, so when you won again I got pissed and doubled down, and well you know the rest. So anyway, I was going to let you out of it. I never did any of this kinky stuff before and honestly never had any desire to. But then Jane told me about what you guys did last night, and I have to admit I was kind of intrigued. I know she told you about my cheating ex. I’m still pretty pissed about it and I thought this might be a good release for me. You’re obviously into it, so I wanted to do a little test run tonight, see how I feel about it, and go from there. Cool?”
I’m blown away. Guess she doesn’t hate me after all? “Um, sure, whatever you want to do, but where’s Jane?”
“She’s taking a shower. Relax, this was her idea, she’ll be here soon. But don’t give me that ‘yes ma’am whatever you say’ slave bullshit. Are you really okay with this?”
“Yeah, I’m fine with this. Seriously. Plus I’d never back out of a bet.”
She studied me for a moment, “Fine, let’s get started. I want you to lean over the back of the chair you’re sitting on.” Our desk chairs have pretty low backs, so I was able to lean over it easily, bracing my hands on the seat. I watched as she grabbed a hair brush and positioned herself behind me. Her first hit is pretty light, like she’s testing things out. She gives me a few more each a little harder than the last, but still pretty tame. Also I’m still wearing my pants, so she doesn't get much of a reaction out of me. I was about to encourage her to go harder if she wanted but the next hit showed me I didn’t need to. I cried out in surprise as she put her all into it. Then she did it again, and again. I was able to brace myself better now that I knew what was coming, but it was starting to hurt pretty bad. I was sore from last night and I’m thinking Heather is a lot stronger than Jane. She really started getting into it as the blows came harder and faster. Each shot caused an involuntary noise to escape. Grunts and whines, mostly. I started to wonder if she and Jane talked about our safeword discussion from last night.
Before it became an issue Heather stopped and was standing behind me, panting. I wasn’t certain if she was tired or excited, maybe a bit of both? “Stand up and face me.” I did and was a little embarrassed at the erection tenting out. Boxer shorts and sweatpants don’t offer much resistance. “Pervert.” She put her hands under the front of my shirt, sliding them up past my stomach to my nipples. She grabbed each one and pinched, then twisted. “So you really like this stuff, huh?” I was still adjusting to the new sensations so could only nod. “You were making a lot of noises when I was spanking you. Even then you liked it? You didn’t want me to stop?”
I wasn’t sure how to explain this. I don’t really understand it myself, “Yes and no. I mean it hurts and I want it to stop, but I like it at the same time. Especially when someone is forcing me to take it. It really turns me on…obviously.”
“Yeah, I don’t get it, but I have to admit I kinda liked hitting you, and watching you squirm now is pretty cool. But I refuse to believe you like having your balls hit. When Jane told me about that I thought she was bullshitting me.”
I was having a hard time keeping eye contact, “No, it’s true. I…” I was cut off when out of nowhere she swiftly raised her knee into my balls. I would have fallen to the ground but she never let go of my nipples. However, my hands did instinctively grab them.
“So you’re telling me you liked that and want me to do it again?” Once again I could only nod. “Then why are you covering them up?”
“I can’t help it. It’s a reflex.”
“I see, ok, put your hands on my shoulders and leave them there. I want to try a few more.” I again obey and am rewarded with three more swift knees to my balls. It takes a lot of willpower to not move my hands, and her vice like grip on my nipples keeps me in place. She pauses and looks up at me, studying me.
Just then Jane comes in wearing only a towel. “Well don’t you two look cozy?”
I panic for a second thinking I was just caught cheating, but Heather just rolled her eyes, “Well if your slave could just control himself.” And delivered another knee. They both laughed and Heather finally let go and took a step back from me. “Well this was interesting.”
“So you liked your little test drive?”
“Yeah, more than I thought I would. Tomorrow should be fun.” They both look down at the tent I’m still sporting, “Looks like he liked it too!”
“Hmm, maybe I should be jealous.” Jane drops her towel to reveal her nude body to both of us as she grabs and puts on her own sleepwear.
Heather quickly looks away, “Goddammit, will you stop flashing me!” She then looks at me, “She does this all the time. She has no shame.”
I smile as I stare, “I don’t mind.” Out of nowhere Heather delivers a kick to my groin and I immediately drop to the floor as the girls laughed.
Jane finished getting dressed, “Ok, you’ll have your fun tomorrow, he’s mine for tonight.” Jane grabbed my hand and helped me to my feet.
“Fine, but bring him here by 10am. I want to get a light workout in the morning first.”
Jane agreed and pulled me out the door and back to my room. We briefly talked about what Heather did with me. We talked about my stroking assignment and how incredibly horny I am. I asked her about the number of edges I did and she admitted she was just curious how many I’d do. This led to us naked in bed making out and having sex, but of course I still wasn’t allowed to cum, only Jane. After she was finished we drifted off to sleep.
We woke up around 9 and Jane insisted I shower and shave then go get some breakfast. She wanted me to look my best and have enough energy for the day. I felt like I was her prize show dog that she was going to be trotting out for display later. By 10am we were back in her room. Heather was waiting for us, still dressed in what I assume was her workout clothes. Sports bra and gym shorts, bare feet and her hair in a ponytail. She really nailed looking sexy without trying. She also looked disappointed when she saw me, “Jeans? Cheating already?”
Before I could reply Jane stepped in, “I wanted my slave to look nice for you. Figured you’d be stripping him down, anyway.”
“No no no. I don’t need to see your boy toy naked. It’s bad enough I have to deal with you flashing me all the time. Is he at least wearing underwear?”
Again Jane spoke for me, “Yeah, he wears boxers.”
“Ok, that might work. Oh! I have a better idea. Does he have a swimsuit here?”
There’s an indoor pool on campus that I’ve used a few times, so I did have a couple pairs with me. I got so used to Jane speaking for me I didn’t realize they were both staring at me waiting for a response, “Oh, uh, yeah. I have some in my room.”
“Duh, I didn’t think they were in your pocket! Go down and change into a pair. No underwear, keep your shirt but lose the socks and shoes. And hurry!” I jogged down to my room and quickly dug out a pair of swim trunks. Threw off my clothes and put them on. They have an inner lining that’s pretty snug and keeps my junk in place. Once ready I jogged back up to their room. As soon as the door was closed Heather wasted no time, “Good, lean over the back of the chair, same as last night.” I assumed the same position and was surprised when I felt Heather tie something around my right ankle. I looked down to see her with a large bundle of what looked like a clothesline. “Just something I picked up on my run this morning since you had such a hard time controlling yourself.” She secured my ankle to the leg of the chair and did the same with the other. Moving to the front of the chair she secured my wrists as well. She left and came back a moment later, kneeling down in front of me to look me in the eye, holding up a pair of panties. “See these? I wore them all day yesterday, slept in them last night, and had them on during my run this morning. Open your mouth.” I hesitated for a second but realized I was in no position to argue so complied. She wadded them up and put them in my mouth. “Don’t drop them, or I’ll be pissed!” They did not taste good, but her threat was enough motivation to keep my mouth shut. Her final touch was putting a sleep mask over my eyes, blindfolding me.
The stereo came on, not too loud but enough so I couldn’t make out what they were saying to each other. I just heard enough to know they were talking and giggling. So I was pretty surprised when the first blow landed on my behind. It felt like the same hairbrush she used last night. “You know I only had enough time for a run this morning.” Two more hits. “So I had to skip my upper body because of you.” Three smacks. “That means this is going to be my workout.” Four more. “And that’s ten, time to switch arms. Let’s see how many sets I can get in before I feel the burn.” Ten more. “I’m guessing you’ll be feeling the burn way before me, but that’s okay. We’ll whip you into shape in no time!” I groaned more at the bad joke than the pain as she laughed and dealt another ten. This continued for some time. Ten with one arm, ten with another, then a minute or two rest where Heather would either taunt me or talk casually with Jane. On the one hand the frequent breaks were good, it helped me manage the pain better, but that also meant she could drag this out and make the spanking last a long, long time. Which is exactly what she did. I lost track of time as my mind started to float away. Later I would learn it was from pain endorphins, some people call it subspace, but at the time I was oblivious and simply endured. I was helpless to stop it or do much of anything except grunt and squeal through the panties in my mouth. I didn’t notice her last break was longer than normal until the blindfold was removed and Jane was looking at me concerned. “Hey babe, you okay?”
Slowly I came back to the room and nodded my head. Heather was impatient, “See? I told you he’s fine. He likes it. Check his cock I bet it’s like a diamond.” She wasn’t entirely wrong. “So can I keep going? I was just getting warmed up!”
Jane ignored her and moved closer, “You’re taking an awful lot, it must hurt real bad.” I nodded again. “Doesn’t part of you want to stop? We could crawl back into bed together.” I groaned and nodded. “But you don’t want to stop, do you? You want to show your mistress what a big, tough slave you are, don’t you?” I paused for a second and nodded once more. She smiled and gave me a kiss on the cheek, “Good boy. Go ahead and impress me!” She replaced the blindfold and moved away, “He’s all yours.”
“See, told you he was fine. I want to do something different anyway.” She untied my wrists, then my ankles, and stood me up, turned me around and directed me down to my knees. She forced me legs apart and tied rope around my leg, just above the knee, and secured it to the back legs of the chair. More rope around my ankles and I guessed she tied them to the front legs. Then pulled each arm behind me and re-tied my wrists to the front of the chair as well. It was very uncomfortable and left me feeling very vulnerable. I heard her rummage through her desk and then her hand went up my shirt, dragging something very cold. I found out later they were binder clips, I only know when they were attached to my nipples I screamed into her homemade gag. It took several moments for the sharp pain to turn into a dull ache and she just left me there to allow it to happen.
I jumped when I felt hands snake down the front of my trunks, “Relax babe, it’s just me. Need to make some adjustments.” It was Jane. She first positioned my cock so it was pointing straight up, then pulled down slightly on my balls and put something around them. It was like a rubber band but much softer, maybe a scrunchie?
The other desk chair dragged over in front of me. “That was a pretty good upper body workout, but you can’t ignore the legs. My jog this morning was nice, but I think I just need a little more.” Heather’s foot was pushing into my crotch, probing and exploring. It felt good, but I knew what was coming. Sure enough her foot retreated but quickly came back with force. I couldn’t close my legs or move my arms. Once again I was completely helpless. All I could do was scream into her panties as she repeated a similar routine as before. Mercifully, it was cut in half. Five with one foot, five with the other, then a break. Her taunting during breaks was more direct this time, “You’re such a bad boy, you deserve this, don’t you?” I quickly shook my head. “Liar.” Another round of kicks. “You boys are all the same. You act all sweet to get in our pants, but deep down you’re all rotten.” I grunted uh-uh and shook my head, and was rewarded with another flurry. “Sure. It’s only a matter of time before you get bored of this little slave game and hurt my friend Jane.” I kept shaking my head. “She really cares about you, you know?”
Jane yelled, “Hey!” That got my attention.
“What? It’s true isn’t it?”
“Will you shut up already?!”
“What the hell are you smiling about?” I didn’t even realize I was smiling, or at least trying with the panties in my mouth. But that quickly stopped when her next set of kicks hit home. She didn't taunt for the next few sets. Aside from the music, the room was quiet except for Heather counting out each kick like she was lifting weights in the gym and me yelling with pain after each one.
Jane broke the silence, “I better check on him again.”
“See? Told you you cared about him!”
Jane laughed, “Stop! I don’t want you to break the poor boy.”
“I’m telling you, he’s fine. I can still see his big, hard dick through his shorts. Hey slave boy, you okay?” I slowly nodded. “Am I being too rough with you? Need me to stop?” I hesitated and shook my head. “There, happy?” Another set of kicks then I heard Heather get up and go back to her desk. She returned and ran her hands up my shirt again. She was fiddling with the clips that I had not forgotten about. When she finished a new pain set in as the clips, and by extension my nipples, were pulled down. Something heavy was hanging from them. Before I could adjust to the new pain, she went through another set of kicks on my balls. After a few more sets I didn’t know if I could handle anymore, but I also didn’t know how to make it stop. Jane was obviously keeping a close eye and I started to come up with ideas to signal her, but before I had the chance Heather got up and roughly pulled the clips from my nipples. It took a minute but a new, sharp pain flooded over me as the blood rushed back. I howled through the gag. Once I calmed Heather said, “Well I don’t know about you guys, but I’m starving. All this working out really gave me an appetite.”
Jane agreed, “Good idea. He could use the break. Let’s untie him and we’ll get lunch.”
“Oh, no. He’s not going anywhere. You can bring him something back, but he’s staying right there for now.” I groaned. This position was getting really uncomfortable. I was distracted by it from the other pains, but now that they’ve stopped I’m realizing how bad kneeling down here feels.
“Can you at least let him sit on the chair or bed or something? Look at him, we can’t leave him alone like that. What if he cramps up?”
I could picture Heather’s eyes rolling, “Fine, we can sit him on the chair and tie him. Will be easier for you to feed him that way anyway. Oh, I have an idea.” I couldn’t hear what this idea was. All I could hear was the music. Still silent I felt the ropes from my ankles and legs undone, and then my wrists. They both helped me to my feet and sat me in the chair after turning it around. My ankles were again tied to the legs of the chair and my wrists tied behind me. More silence as the girls conspired quietly. Heather finally said, “Fine, meet me downstairs. I’ll save us a seat.” I heard the door open and close.
“Good, I don’t know how much longer I could wait.” During the silence my penis finally relaxed, but Jane put an end to that as she pulled my shorts down enough to set it free and rubbed it wide awake. “I don’t have a lot of time, just enough to get a taste.” I could feel her climbing on the chair and straddling me, then I was deep inside her and it felt like heaven, especially after everything I’d been through. She rode me hard and fast for a few minutes and surprised me when she suddenly got up and off me. “Oooh, what a tease! Is this what you feel like? You must be going crazy! But I need to meet Heather downstairs.” A moment later Jane started rubbing my balls. I felt something cool on them, like some kind of cream, then she pulled the scrunchie off me and pulled my shorts back up. A kiss on my cheek and she was gone.
Whatever she put on me was nice. It was cool and soothing for my poor, aching balls. I relaxed, waiting for them to return. But a few minutes later that cool soothing turned hot. Very hot. It felt like my balls were on fire and it wasn’t going away. Once again I screamed futilly into my gag as intense pain overcame me, only this time there was no one here to care. I don't know how long I sat there alone in agonizing pain. It felt like hours. Eventually the pain subsided as whatever was in that cream wore off and I sagged into the chair, finally able to relax. A few minutes later I heard the door and the girls returned.
Heather spoke first, “Oh good, you’re still here!”
“Funny. How are you doing? Are your balls feeling better?”. I nodded.
“See? I told you that would help. I'm not completely heartless.” I wasn’t sure what Heather was talking about. From my point of view that's exactly what she seemed. Not soon after I felt my shorts pulled down again and that cream being rubbed into my balls! I violently shook my head trying to say no!
Jane shushed me, “Poor slave, I know your balls are still probably sore, I'll just be a second and we'll let the cream do it's trick.” I continued to protest as much as I could. It wasn't until Heather started laughing before Jane realized what was happening. “Fuck. Does this stuff hurt?” I nodded vigorously. “Goddammit Heather!”
She laughed even harder. “My ex told me about this stuff. He pulled a muscle in his thigh once and put some on to help. He told me he accidentally got a small drop on his balls and it felt like they were burning. I think on fire was the way he put it. Takes a few minutes before it kicks in and water only makes it work so you can't wash it off. He just had to ride it out. So nothing to do now except sit back and watch the show!”
Jane didn't seem happy, “I'm sorry, I really didn't know. She told me it helped soothe sore muscles and would help you.” She pulled my shorts back up, gave me another kiss on the cheek and left me. Just like before the burning set in, worse this time. I screamed and thrashed in the chair. I'm sure Heather was very entertained as I heard her giggle every once in a while while Jane would just call her a bitch. After another eternity the cream was wearing off again and I was calming down. The blindfold was removed by Jane who was sitting in the other chair in front of me. Heather was on her bed, dressed in more casual sweats again, reading a textbook. “Let’s get that out of your mouth so you can eat.” I opened my mouth and Jane carefully removed the now drenched underwear. “Maybe I should be jealous, you really soaked Heather’s panties.”
Heather never looked away from her book, “You’re such a dork. He better wash them before giving them back.”
Jane rolled her eyes, “I’ll take care of them.” She untied me from the chair and handed me a tray from the cafeteria that had a sandwich, chips, and a bottle of water. She took her chair over to her desk to let me eat. I downed half the bottle and devoured the food, then finished off the water. Didn’t realize how hungry and thirsty I was.
Once I was finished I wasn’t sure what to do. They were both engrossed in their books and not paying me any attention. I probably should have enjoyed the break but I get bored very easily, “So, um, what now?”
Heather looked up from her book, “Ready for round two already? Jane was right, you are a pain slut.” I blushed forgetting how Jane apparently kept no secrets. “Why don’t you go use the bathroom. Don’t want you making a mess in my room.” Once again I was oblivious to my own body. I really did need to pee, so I travelled down the hall, enjoying the ability to walk around and stretch my limbs. When I returned Heather was back in her workout attire holding the ropes in her hand. She pointed to Jane’s bed, “Lay face down. I don’t want you dirtying up my bed.” I did as directed. She tied my ankles to the bottom of the metal bed frame and had me raise my arms up to tie my wrists to the top of the frame. “During lunch Jane told me about your little safeword. I like it, but I don’t want to use yours. ‘Mercy.’ No fun in that. If you want me to stop you have to say ‘I’m a little pussy bitch.’ Do you understand?”
Ugh, why is she so mean? “Yes, I understand.”
“Well then say it so I know for sure.”
I sigh, “I’m a little pussy bitch.”
“Yeah you are. What do you say, Jane, ready?”
Jane hesitated, “Fine.” She turned to me, “We made a deal. If I leave you two alone for a couple hours you’ll be done for the day, otherwise she gets the full day like you stupidly agreed to. I made her promise to respect your safeword. You okay with this?” I was not! Especially after the trick she just played with the sports cream. But Jane obviously trusted her, and I really wanted it to end. Jane is the one I want to be doing this with, so I reluctantly agreed. “I’ll be in the lounge. See you in two hours.”
Once the door closed Heather Started in, “No one here to protect you now. One thing she didn't mention about your safeword. It’s a test. If you don’t use it, she’s going to make you cum tonight, but if you say it then you’re going to be waiting until the weekend at least! I’m not supposed to tell you, but I wanted to give you some incentive to not use it so it’s more of a challenge for me to make you give up.” If she was trying to scare me it was working. I was tempted to give in right away, consequences be damned. Unfortunately I was so horny I couldn’t pass up any chance to finally get some relief. “I’m not allowed to gag you again, so you better keep your voice down. If anyone on the floor complains, I’m going to be super pissed and you’re going to be really embarrassed when I let them see what all the noise is about. Just shove your face in the pillow if you can’t control yourself.” She grabbed the blindfold and put it back on my head and turned the stereo up a little louder.
I layed there waiting, anticipating another spanking, but there was nothing. I started getting anxious and jumped when I felt a hand lightly touch my back. Heather was right by my ear as she laughed, “Wow, you sure are jumpy! Nervous about something?” She didn’t wait for an answer, “I’ll bet I know what it is. You’re a cheater, aren’t you? You’re afraid I’m going to find you out and tell Jane.”
I quickly protest, “No! I’d never cheat!”
“Uh-huh. We’ll see. I’ll get the truth out of you.” She left me alone again for a couple minutes, heightening my anxiety again until I felt something slap across my back. “I bought a cute, new belt over break. What do you think of it?” It came down again, this time over my upper legs. Then on my butt. She spread the blows out all across the back of my body, randomly hitting me over and over again. “If you admit you’re a cheater I might go easy on you.”
“But I’m not!”
“Have it your way.” She resumed her attack. I managed to not yell out at first, mainly just grunts, but it was slowly becoming more than I could handle. As I gradually got louder she stopped, “I told you, use the pillow if you can’t control yourself. Let me ask you this, cheater. The girl you were dating when you met Jane, did you break up with her before or after you guys started fucking?” Shit. She got me, technically. I did break up with her the next chance I had, but Jane and I got together so fast. When I didn’t promptly answer, “Yeah, that’s what I thought. You’re just like every other guy. You deserve this.” She continued whipping me, harder and faster this time. Almost immediately I had to turn my face into the pillow so I could yell out to help manage the pain. I was getting very close to calling my safeword to make this stop, but managed to outlast her. Instead, she untied me and ordered me to roll over onto my back. Everything back there hurt, so laying on it was a new pain, but better than more whipping.
After securing me back to the bed frame I felt her get on the bed, between my legs. She removed the blindfold, “I want you to watch this part.” I noticed she had on a pair of gloves. They were fingerless with thick padding. “I use these for my kickboxing class. It’s a great workout. You felt the kicks earlier, now you get the boxing.” She delivered a quick one-two punch to my crotch. I howled in pain but she wasn't satisfied. She went back to the desk to grab something, returned and quickly pulled down my trunks enough to expose my cock and balls. She had gotten the scrunchie from the desk and wrapped it back around my balls. She delivered another one-two this time directly on my balls, but she still wasn't happy. Picking up the remaining rope she fished it underneath my back and wrapped it around my stomach and cock, holding it in place and out of the way. Two more punches and she was finally pleased with her set up.
The other night I couldn't handle Jane's eleven punches. Heather was stronger and already gave me six, how could I possibly endure much more? Lucky for me she went easy at first, lightly jabbing with both hands, treating my balls like a speed bag. Out of nowhere she delivered one hard punch, causing me to thrash against the ropes and yell in pain. She went right back to the light jabs, “Admit you’re a rotten cheater, just like every guy.”
“But I’m not, I…” Another hard punch.
“Again with the lies. True or false, you had sex with Jane before you broke up with your ex?”
Ugh, “Technically true, but…” The next punch finished my sentence for me.
“Exactly. So technically that makes you a cheater!” Punch. “So admit it.” Punch. “Admit you’re a cheater!”
Every punch is followed by the steady jabs and she alternated which hand delivered the big punch. Even now it seemed like she was treating this as exercise. I didn’t know what to do. Do I just give in and admit it and she’ll ease up, or will it get worse as punishment? I decided to try and plead my case, “I broke up with her the next time I saw her!”
Punch. “Yeah, only because you found someone else to fuck. So what happens when you find someone you like better than Jane?”
“I already decided to break up with her before I met Jane! Honest!”
One-two punch. “Easy to say that now. Be even easier to just come clean to me.”
The harder punches came more frequently and it wasn't long before I reached my limit. “Okay, okay! I'm a cheater! I'm a cheater! But I won't cheat on Jane, I promise! Just stop, please stop!” Thankfully she did stop completely. I thought she'd be pleased with herself, but the way she was looking at me was concerning. Nothing happened for a while and no words were spoken. I was grateful for the break so I closed my eyes and caught my breath, trying to relax. I hoped our time would be up soon and Jane would return.
I opened my eyes as I felt her cradle my balls with one hand. “I knew it. So why'd you do it? Why'd you cheat on me?”
“What? But I never…” She punched. With her holding my balls they had nowhere to go so I felt the full force and the pain was immense. I was done, “Please stop! Mercy! Mercy!”
Instead she hit them again and again, “I loved you, Mark, and you cheated on me! Why? What did I do wrong?” Mark? Who the fuck was Mark? And what was her safeword? Something about being a pussy, or was it a bitch? Shit! She hit me a few more times, causing tears to stream down my face. In between she kept going on about how terrible I was and how I hurt her and cheated on her, completely ignoring my pleas to stop.
This went on for a couple more minutes and my pleas changed to forgiveness, “I’m sorry! I’m sorry!. Please, I’m sorry I cheated, I’m sorry I hurt you! Please stop! I’m so sorry!”
One more punch on my balls, then a few times pounding on my chest as she broke down in tears, “I hate you.” She then collapsed on top of me, her head on my chest as she cried. I didn’t know what just happened and I was legitimately scared. Still helpless to do anything, and too scared to speak, I simply laid as still as I could wondering how long my balls would be aching. The pain I endured was so great even my penis had had enough and went limp, which I was thankful for since Heather’s chest and bare stomach were now laying on it, rubbing as she sobbed. Once she composed herself she sat up, “Jesus Christ, I’m so sorry.” She released my wrists then got up and untied my ankles. “Are you okay? Fuck, I don’t know what happened. I didn’t mean to, I mean...shit.”
I pulled up my shorts and stood up. Even though everything on me was sore, and probably would be for a few days, I assured her I was fine and asked if she was good? She told me all the details about her ex, Mark. How they dated all through high school and she thought they would get married someday, but when she went home for winter break found out he had been cheating on her all semester. To top it all off, she found out on Christmas! Ever since she’s just been angry and bitter. This was the first time she even cried. She apologized for putting me through everything and for ignoring my calls of mercy at the end. I assured her it was fine, but I was embarrassed that even though I was scared and wanted it to stop, it was exciting that it didn’t and I was helpless to do anything. She shook her head, “I can’t believe you liked all that, then again I can’t believe I liked doing all that to you.”
“Hey, um, since you ignored my safeword, can we not tell Jane about it? I’ve never gone this long before and I’m dying!”
She just laughed, “Oh shit, sorry, but I made that up! She never said anything about holding out and getting to cum or whatever. I was just fucking with you!” She kept laughing but I was both heart broken and a little pissed. “Awww, yeah that seems pretty shitty of me now after all that. I kind of feel like I owe you one.” I arched my eyebrows, hopeful. “Don’t get too excited, I’m not offering to jerk you off or anything, but I can put in a good word with Jane and see what I can do.”
She put her sweats back on and we continued to chat for a bit. Turns out Heather is actually pretty cool. After talking for around ten minutes Jane walked in and did a double take, “Wow, this isn't what I expected to find. What happened? Did he wimp out on you?”
“No, he was good. I was just done and didn’t want to play anymore. I’m going to go shower.” She gave me a hug and thanked me for the fun day, grabbed her things, and left the room.
“That was weird, what happened?” I promised to tell her but asked if we could go back to my room for now, and she agreed. She left a quick note for Heather, grabbed her bookbag, and we left. Once we got to my room, she had me strip so she could inspect my body as I gave her a complete recap of what happened, except I toned down Heather’s break down and ignoring my pleas to stop. I told her the whole story while I was standing, because sitting hurt too much. “Wow. Sounds like I went too easy on you the other night! Or maybe you just weren’t desperate enough to cum yet? I’ll keep that in mind for next time.” It was only around 3:30 and we had the rest of the day with nothing to do. All I wanted was to soak in a bathtub and take a nap, but there was no tub in the dorm and Jane definitely wasn’t sleepy. “You know I’m still worked up from that quickie we had earlier. You have me so spoiled lately, I forgot what sex without an orgasm is like. I thought it might be fun to let you tease me for a bit. What do you think?”
I thought that sounded like a great idea, but I didn’t know if I was up for it physically. However her question was rhetorical as she started removing her own clothes. She went into her bookbag and pulled out the remaining rope that Heather had bought. I didn’t even notice she grabbed it from the room. She handed me the rope and laid out the rules, “I want you to tie me to your bed. You’re still not allowed to cum and no pain. I just want you to get me close to cumming but don’t let me, no matter what I promise or threaten. I want to get an idea of what you’re going through. Got it?”
I smiled, “Yes, Mistress. Or should I be calling you slave now?”
She lightly slapped my balls, but it felt like another punch, “Don’t let it go to your head. I’m still in control, I’m just letting you do this because I want to experience it.” I laid her down and tied her the same way that was done to me, arms raised above her head, wrists and ankles secured to the metal bed frame. I laid on top of her and we kissed. I very slowly started kissing my way down her body. I lingered on her neck. Lingered on each breast and nipple. Then her stomach. Skipping her pussy I went to each thigh and down each leg. I reversed back up her body, purposely skipping the part she wanted my mouth on the most. By the time I got to her mouth she was squirming and calling me a bad boy. We kissed again as I let my hand gently touch her lower lips, gently brushing against her, she moaned into my mouth. I kept sliding my fingers back and forth, barely making contact. Her hips would arch, trying to increase the pressure, but I would just pull them away, keeping it constant. Her moans turned to squeals as she tried in vain to get the stimulation she craved.
She then got demanding, “Fuck me! Fuck me! I want to feel that cock inside me!” I positioned myself on top of her and rubbed my cock head against her opening but never put it inside. “That's it baby, give it to me! Fuck me!” Despite the fact I wanted to do just that, instead I kept rubbing myself on her lips.
I started getting bold, “You want me? Beg for it. Beg for my cock!” And she did. I let her go on for several minutes while I simply kept rubbing, teasing myself at the same time. I finally gave in but just put the tip inside her. At first she shouted “Yes!” until she realized that's all I was giving her, so she reverted back to begging. I pulled out as much as I could and then back in, fucking her with just my cock head. It wasn't enough for either of us but I was determined to tease her as much as I could and give her a taste of her own medicine. She started bucking and thrashing wildly, desperate to get more of me inside her. I had to pull away completely, which made her utter an angry whine.
I climbed off the bed, grabbed the unused rope, and fastened her thighs to the frame. She tried to scold me, “You’re being a very bad boy! You’re going to be in so much trouble once I’m free!”
I smiled, “I’m only following your orders, Mistress.” She did not find that as amusing as I did. I climbed back on top of her, repositioning my cock against her pussy, but not entering, and started focusing all my attention on her breasts. I licked, sucked, and nibbled her nipples, alternating between the two. Her hips kept bucking, but were limited thanks to the ropes.
Her frustration was already starting to boil over. “This is not what I meant! You’re supposed to lick me or fuck me and just stop when I get close!” She thrashed in her bonds, “Well untie me if you aren’t going to do it right!” I ignored her pleas and eventual threats to either make me wait a month to cum or beat my balls. Instead, during the latter threat, I cut her off by swiftly thrusting deep inside her, “I’ll beat your balls so bad you’ll...Oooohhhhhh! Yes!” But I didn’t move after that. I kept myself buried deep and rained kisses on her neck. She’s able to grind her hips around a little bit, getting some much needed friction, but I do my best to match her movements. She eventually tires and lays still, or so I thought until I feel her squeeze around my cock. I stop kissing and gasp in surprise. She begins rhythmically flexing her vaginal muscles, applying just enough pressure on me to drive me crazy. I should pull out and not let her get the upper hand, but the sensations feel so good and at the same time make me want more. Even though she’s the one tied down, I suddenly find myself helpless as I start slowing fucking her, causing her to sigh in contented relief. Somehow I manage enough self control to keep the slow pace so neither of us has an accident, but I have her so amped up she’s quickly approaching orgasm. “”Yes, that’s my sweet boy. Fuck me! Keep fucking your mistress!” That spurs me on to pick up the pace just slightly, but now I can feel my own overdue impending orgasm as well. We’re both getting closer and closer, and I’m certain if I keep going we’d simultaneously cum, but I stop a few strokes short and pull out completely. “No! Dammit, I was so close!” She thrashed in her bonds again, desperate to get free while I caught my breath and slowly backed away from the orgasmic cliff once again.
Once she was done struggling and cursing me, and I was settled, I laid on her side and let my hand drift between her legs. This time instead of barely touching I applied direct pressure, which based on her reactions were much appreciated. Here’s where I decided enough foreplay, time to really show her what the teasing is like. I spent the next half hour rubbing and massaging her sex, stopping anytime she got close, let her catch her breath, and do it again. I lost track of how many times I edged her, but by the end she was a blubbering mess. Now instead of threats she was merely begging and offering me the world if only I would finish her off. I knew the feeling all too well. After she stopped making me false promises I asked, “So how do you like being on the receiving end?”
“Jesus, I’m going out of my mind! If I don’t cum soon I think I’m going to die! Is this how it feels for you?” I nod. “And you like this?”
“Yes and no. Orgasms are different for me and you. After you cum you want to keep playing and want more. For me once I cum, I’m done and lose interest for a little while. Plus, I like giving up control. But don’t get me wrong, all I’m thinking about right now is finally getting to explode.”
“Not me, this is insane. Finish me off already, I’ve had enough!”
I smile as I slowly lower myself down her body, “You never said how long we should do this for and unfortunately we never discussed a safeword. I want to be a good slave and follow orders, so just to be safe I think we should keep going.” Before she could protest I put my tongue to work, temporarily distracting her. I did my best to replicate what I just did with my fingers, but she’s clever. She did her best staying quiet, trying not to give me any clues that she was getting close. Because of that I had to stop much sooner than I probably needed to for fear of pushing her over before I was ready. She quickly realized I was on to her and went back to cursing and threatening me. I had no doubt once I was in her position again I would regret doing this, but in the moment I couldn’t help myself.
My mouth was getting tired. Come to think of it my entire body was tired from the crazy day I’ve had, and my stomach was starting to rumble. I stopped what I was doing, ignoring her pleas to continue, and crawled back up so I was laying next to her again. Her eyes were closed as she tried to catch her breath. I gently whispered into her ear, “How about we take a break and grab some dinner. We can continue when we get back.”
Her eyes flew open as she turned to me, “Nooo! Don’t you dare!”
I smiled and got a little cocky, “Yeah, I’m starving. C’mon, we can play some more when we get back.” I got out of bed and untied her feet and then her hands, but I wasn’t ready for what was next. Like an idiot I forgot she just let me tie her up and wasn’t committed to a submissive role like I was. She quickly grabbed my balls with a death grip, pulling me back onto the bed. Once she had me laying down she let go and delivered a very hard punch. While I was howling in pain, trying to recover, she took advantage of the moment and tied me to the bed, in the same position she was in moments earlier.
As she climbed onto me in a 69 position she said, “The longer you take the more it’s going to hurt.” I wasn’t sure what she meant as her pussy lowered onto my mouth until the first slap hit my balls. I was still sore from Heather’s session, and that last punch didn’t help matters either, so each slap was excruciating. I quickly went to work, trying to get her off as fast as possible. She leaned forward, putting just my head in her mouth, alternating between pleasurable sucking and painful nibbling. Fortunately I had her so worked up it wasn't long before she stopped hitting me, dropped me from her mouth, and clenched her thighs around my head hard as she started screaming, “Yes, yes, fuck yes!” I didn’t dare stop or slow down until I knew she was finished. I’d never heard her cum for so long or so loudly, even through her legs clamped around my ears. Once she settled down, I slowed my licking and started to relax and was rewarded with another ball punch, “Oh no you don’t. After everything you did you think I’m going to be satisfied with one lousy orgasm? You better get busy down there if you know what’s good for you!” I didn’t need to be told twice. She kept me down there for four more, until my jaw was sore, my balls were in agony, and my tongue exhausted.
Finally sated, she got off of me and the bed, “Ahhh, you know you’re right, we should get some dinner. I’m suddenly famished!” I could only lay there and groan. “My poor sweet boy. Doesn’t seem fair, does it? You did exactly as I asked and this is how I thank you?” She untied me and helped me sit up then sat next to me on the bed. “How you holding up?”
“I feel like I could sleep for a week. And everything just hurts, especially my balls.”
“Yeah, you had a pretty rough day. You really surprised me when you were in control. Truth be told, I can see why you like it so much. Being helpless to you was kinda hot. Makes me wish I gave you permission to cum so you could have really used me.” I involuntarily whined a little when she said that, which made her laugh. “Cheer up, maybe we’ll try that next time. I’m really impressed how you control yourself when not tied up, though! I could never do it, obviously. I almost fucked your brains out but didn’t want to ruin your streak.” She gently squeezed my cock, causing a gasp. I wanted to ask how long she intended this ‘streak’ to go on for, but after how she reacted the other night when I asked, I decided I better not chance it. “C’mon, let’s get dressed, I really am hungry.”
After a quick bathroom break we dragged ourselves down to the cafeteria for some dinner. Afterwards we went back to our own rooms. Jane knew if she was with me she wouldn't be able to help herself and thought I should get some much deserved rest. Once alone I laid in bed and watched some TV, but soon drifted off to sleep and didn’t wake until the next morning. The sleep really did me good. Although most of my body was still sore and hurting from yesterday, especially my bluer by the day, abused balls, I felt refreshed. I leisurely got myself cleaned up and ready for class. The shower never felt so good even though the water hitting my back was pretty uncomfortable. I got myself ready a bit early so thought I’d just take a slow walk to class.
When I opened the door I was surprised to find Jane there, just about to knock. She smiled, threw her arms around me, and gave me a big kiss, pushing us back inside. I started to take my clothes off, but she stopped me, “No, silly, we’ll be late for class. I just came down so we could walk together.” So we did, hand-in-hand. As we walked she told me that we should take the day off from playing but still wanted to hang out together tonight and watch a movie. We made plans to meet at my room at 8pm, kissed our goodbyes and went our separate ways for the day.
My first class let out early and as I was headed to my next I spotted Heather coming in the opposite direction. I was still unsure of our relationship. I assumed after yesterday it would be awkward between us, so I meekly smiled and offered a small wave. In return I got a big smile and a hug! She asked how I was feeling and thanked me again. After assuring her I was good she asked, “So what exactly did you tell Jane? We were talking last night but I was being a little vague because I felt terrible about what I did and didn’t want to make her mad, but it seemed like she knew something.” I quickly explained how I told her everything minus her breakdown at the end. Otherwise I made sure Jane knew exactly what happened. That seemed to put Heather at ease. “Ok, thanks for that. And I was serious about getting her to go easier on you. I’m going home this weekend and I suggested she reward you for yesterday. Figured I owed you that much, but I’m not going to make a habit of this.”
“Wow, thanks. So we’re good? I was afraid it would be weird between us.”
She smiled, “No we’re cool. You’re a good guy. You’re into some weird shit, but who am I to judge?” She wished me luck on the weekend and we went to our classes.
The rest of the day was uneventful. Jane came down at eight and we both stripped down and got under the covers to watch a movie. We just held each other and watched, no teasing (well let’s be honest, holding her naked body was teasing the hell out of me!), just cuddling and relaxing together. At the end of the night she wanted to stay over, so we literally slept together, just enjoying being with each other. The next morning she was about to leave so she could get ready for class, “Hey, Heather is going home for the weekend. I’ll have my room all to myself. She seems to think you deserve a reward for being so good this week and I might have to agree. Any interest in keeping me company?”
I was all smiles, “Oh yes, absolutely!”
“Great! I’m meeting up with my friends for dinner, the same girls I went out with the other night, so come up to my room after, let’s say 8pm again?” Of course I agreed. “Cool. And show up wearing just a towel, nothing else. You won’t be needing your clothes.” She winked, kissed me goodbye and left. I had to stifle my growing erection at the thought of finally getting some relief so I could get myself ready for classes as well. The day seemed to drag by slowly. After classes I did my best to distract myself to force 8pm to get here sooner. The time finally comes and I'm hoping I soon will be as well. I completely strip and wrap a towel around my waist. Taking a quick peek out my door to ensure no one is there I hurriedly go to the stairwell and up to her floor. Again checking that the coast was clear, I entered her floor and rushed to her door.
As I knock I hear loud music coming from the room. The door opens and Jane is there to greet me, but instead of letting me in she places a hand on my chest and pushes me back in the hall. After a quick kiss she turns me around, pulls my hands behind my back and cuffs them together. I didn't even notice anything in her hand! Spinning me back around to face her she places the same sleep mask from the other day over my eyes, blinding me again. Her hands sneak under my towel and start massaging my cock, “Are you happy to see me?”
Gasping I reply, “Yes mistress.”
Once I'm fully erect she simply says, “Good. Now don't go anywhere.” And before I know what's happening she pulls the towel from my body and enters her room, leaving me alone in the hallway completely naked except for the blindfold and cuffs. I desperately hope no one walks by and sees me. My mind races worrying about what kind of trouble I could get into so close to graduating. Somehow my erection doesn't waver and stands tall and proud.
A minute later my fears are realized when I hear woman scream in surprise and asks, “What the fuck? Ugh, is this some kind of lame frat thing?”
Meekly I reply, “No, my miss, er, girlfriend did this as a joke. Sorry.”
I could hear her walking closer, “Miss girlfriend, eh?” I heard her knock on the door. “Hey Jane, lose something? He said you’re his miss girlfriend.”
The door opens and Jane laughs, “Did he? Yeah, sorry Becca, is he bothering you?”
“He scared the shit out of me! You’re lucky I found him and not those girls across the hall. They’d probably call the cops.” They shared a laugh, acting like this was totally normal.
“Yeah, you’re probably right, I’ll take him back inside.”
“What the hell did you do to him? His back looks beat to shit.”
“Oh that? He was misbehaving, weren’t you, slave?”
I blushed deeply as my somehow still erect cock bounced at her calling me slave in front of this stranger, as I stutterd, “Y-yes mistress.”
Becca chuckled, “You’re so weird.” Suddenly I felt a smack on my ass. “You two have fun. Nice cock, by the way.”
I felt Jane grab my ‘nice cock’ and lead me into her room, “That was Becca. She’s pretty cool. I’ll introduce you one of these days.” Not sure how I could face her after that. Though since I have no idea what she looks like, for all I know I’ll see her tomorrow on campus and have no idea! Jane stands me in what I assume is the middle of her room. The music goes down slightly. “So slave, how long has it been since your last orgasm?”
I had to do some quick math, “Twelve days.”
“Wow, almost two weeks! You must be a really horny slave, aren’t you?”
“Yes mistress.” I thought I heard a giggle, but just assumed it was the stereo.
“I’ll bet you really want to cum tonight, don’t you?”
It’s a trap, fortunately she doesn’t have me all worked up yet so it was easy to side-step. “Yes mistress, but only if that’s what you want.”
“Clever boy. What if I wanted to make you wait for another week, would you like that?”
Ugh, god I hope she’s just fucking with me, “Yes mistress.”
“What if instead I wanted to spank your ass, or maybe even your balls, until you were begging me to stop only you know I won’t stop. Would you like that?”
Once again she has my cock throbbing and jumping, betraying me at every turn. I gulp, “Yes mistress.”
“That’s my sweet boy.” I feel her removing the cuffs, freeing my hands. “For now, I want you to stroke your cock for me. Hard and fast, get yourself right to the edge and stop. Can you do that for me?”
I sigh, “Yes mistress.” It doesn’t take me long to do as she commands and with great effort I pull my hand away at the last moment, leaving me panting.
After a few moments she simply says, “Again,” and I comply. She had me edge myself five times for her amusement. “I'll bet you really want to cum now, huh slave?”
At this point I'm well beyond being clever, “Yes mistress, please, please let me cum! I'll do anything for you, please!”
“What do you think, girls?” Girls? Oh Jesus, we’re not alone? At this rate I won’t be able to show my face anywhere on campus for fear of some unknown woman knowing my shameful secrets. And it was girls plural, just how many people are here with us?
There’s an awkward silence for a few seconds that is broken by laughter. “Wow, you’re weren’t making it up!” That’s one.
“Where did you find this boy? Better yet, where can I get one?” That was another.
“Sure, he likes playing with his cock, he’s a guy, duh. But I still don’t believe he likes you hitting his balls. I’ll buy spanking his ass, but no guy likes getting hit in the balls. They cry like little babies if you just joke about it.” The doubter makes three, but it sounds like she’s the last one.
Jane spoke to me, “Looks like someone doesn’t believe you, slave. Let’s prove her wrong!” She re-cuffs my wrists behind my back. She asked one of the ladies to move, I assume from one of the desk chairs. Moving it behind me she tied my ankles to it. Shen then whispers in my ear, “You still have your safeword, but I really want to impress my friends. Don’t disappoint me!” I nod and take a deep breath, steeling myself for the upcoming torture. When I feel her grab my cock I jump, eliciting laughter from the crowd. Instead of pain she ties something around my cock, just below the head. “Open your mouth.” I do and I feel her put what I assume is the other end of the rope in it. “Okay, close and hold onto that. I want to keep that cock of yours out of the way. If you want me to stop, just drop it, but if you do that then you definitely won’t be cumming this weekend, got it?” I nod, pulling my cock up and down as I do, creating more giggles from the peanut gallery. I bite down hard on the rope, determined not to drop it no matter what. The first hit tests me, catching me off guard, but the pain caused me to grit my teeth, strengthening my hold of the rope. The next two shots were a little easier to bear. “Do you like that, slave?” I nodded. “Would you like some more?” Another nod. “Now do you guys believe me?” She then hit my balls two more times, emphasizing her point.
Number three, the doubter, is the only one to respond, “Can I try?”
Jane is quick to answer, “I know how you treat boys. I don't want you to break mine.” They all laugh at their inside joke.
“C'mon, how do we know you're really hitting them? You let Heather play with him, why not us?”
“That was a bet. A dumb bet my slave made that he regrets, don't you babe?” I quickly nod again. “I don't know, what do you think, slave, should we let my friends play with you?” I pause for a second, feeling like I'm being tested again. Eager to please I slowly nod my head. Jane laughs, “You little slut. Fine, but just a few, okay? We still have the weekend and I don't want him too sore.”
I could hear someone walk over to me. A hand gently held my balls before two more hard hits enveloped them causing me to yell in pain, but muffled since I refused to open my mouth and drop the rope. “Wow, you two have to try this!”
“Nah, I'm good.”
“Yeah, no thanks. I kinda feel bad for him.”
“Suit yourself, but I get their turns then.” Before Jane could protest she quickly delivered four more.
“Hey, that's enough. You're such a bitch!” They all laughed. “You okay? Did my mean girlfriend hurt you?”
I mumbled a reply causing Jane to laugh again as she removed the rope from my mouth, “No mistress, I’m fine.”
Back to her friends, “See? Now do you guys believe me?” They all agreed they did and before I knew it they said their goodbyes and left Jane and I alone. She removed the blindfold, “Sorry about that. I was telling them all about you over dinner and they thought I was making it up and exaggerating, so I had to prove how great you are. But now it’s just you and me!” She then kissed me and I was all too eager to return it. She maneuvered me to her bed and pushed me down onto it, giving me a chance to finally get a good look at her. She was still dressed up from her dinner date, all in black as usual. Stockings led up to a tight, short skirt and her blouse was lacy and see through enough that you could see her bra underneath. I’m sure she was turning quite a few heads wherever she went, but for now she was causing me to throb and ache even more. As I settled on the bed, she quickly kicked off her shoes and slid out of her skirt, revealing a garter belt holding up her stockings and no other underwear! My eyes bulged out, causing her to wink at me and giggle, “I was out all night like this. Feeling the cool air hitting me was kind of a turn on, but now I need something to warm me up. Have any ideas?” I was speechless, but my cock throbbing and jumping off my stomach was all the response she needed as she removed her blouse and joined me on the bed. Straddling me, she easily slid me inside of her. I was worried I wouldn’t be able to last more than thirty seconds, but instead of riding me up and down, she leaned forward and began kissing me, grinding herself against me. It was still more sensations than I could handle, but I was able to last much longer than I thought I would before begging her if I could finally cum. Her response was to sit up and stop grinding, instead she gave me a show as she slowly began touching herself, masturbating to a powerful orgasm while my poor, deied cock was buried deep inside of her. The display was almost enough to send me over the edge, but I managed to hold back.
After allowing her breathing to slow, she carefully slid off of me and laid down on my side, resting one stocking clad leg over mine, with her head on my chest and her hand very gently caressing my cock, causing me to gasp and twitch uncontrollably. She sighed contentedly, “This is nice, but I’m getting a little cold.” She sat up a little, removing the rest of her clothes, which she threw on the floor, except for one stocking that she draped over my cock. She then turned on the TV with her remote and pulled a blanket over us. After finding something on TV she liked, she resumed her position except now she was using the stocking to caress me, which was driving me insane! Ignoring my plight, she kept telling me to hush so she could hear the TV. And that’s how we spent Friday night until she was tired and ready for sleep. After we both got ready for bed, including me running down the hall in my towel to use the bathroom, we got under the covers together spooning like we did our first night back, with my quickly hardening cock nestled in her butt cheeks. She kept grinding up against me under the guise of her just getting comfortable, but soon she was sound asleep. As I struggled to fall asleep I wondered how much more of this she planned on subjecting me to and how much more I can even handle.
At some point I must have fallen asleep and was having the most vivid sexual dream I can ever remember. Of course, I couldn’t even cum in my dreams and woke up right before I was about to only to find Jane was also awake and using her stocking again to gently caress me, “Good morning, sleepy head. I was wondering how long I’d have to do this before you woke up.” Before I could say anything, she guided my head under the covers. Taking the hint, I positioned myself between her legs and licked her to a nice morning orgasm. Jane then decided we should grab some breakfast. Instead of letting me go get some clothes from my room, she insisted I stay and she’d bring something up from the cafeteria. And of course while she was gone I was to stroke myself and stay as close to the edge as possible.
The rest of the day was a bit of a blur. We spent it all in her room, with the occasional bathroom break or when she left to grab us some food. I was naked the entire time, as was Jane whenever she was with me. She didn't say it, but I think her goal was to see how many times she could make me edge or maybe see if she could just drive me completely insane with lust and frustration. If she left the room I was stroking myself. Sometimes she would just make me stroke while she watched, always amazed at my self control to stop just because she said so. A few times she masturbated along with me, forcing me to watch her get what I was not allowed. If I wasn’t stroking myself, she would use some part of her sexy body to keep me on edge. Naturally, she experienced many orgasms throughout the day as I pleased her in every way possible. The only breaks I received were when we ate. Mercifully, she let my cock relax and it managed to get semi-soft while I ate as slowly as possible, desperate for some rest. The next closest thing I got to a break is when she ever so lightly and gently teased me with her stockings or some other soft and silky piece of clothing she has. Every time I got close I would beg and plead for relief, and each time she would gleefully say no.
After our dinner break, I realized I was done. I couldn’t handle any more. I didn’t even care if she didn’t let me cum tonight, I just wanted to stop and give my poor, tortured penis a break. Before I could fall to my knees and beg her to stop she said, “Hey, I don’t want you to think I’m not enjoying myself. Today has been amazing! But how about we go out for a little bit?” I’m sure I was visibly relieved as I agreed immediately. I don’t know if she sensed how I was feeling or what, but I was pleasantly surprised! I was grabbing my towel so I could go to my room, clean up and get dressed, but before I could leave she told me to wait. She left the room and returned a minute later, took my hand, and told her to follow her. She led me to the ladies bathroom and quickly took me inside. Luckily, no one else was there. She led me to one of the shower stalls and ran the water for us. While I couldn’t argue that we both really needed a shower, it was just another excuse to tease me some more, but this time I didn’t mind. We spent more time than needed sudsing each other up and cleaning our bodies. A few times we heard someone else come in the bathroom so did our best not to be discovered. Surprisingly, she never had me make her orgasm. I assumed she didn’t want us getting caught, so as we were drying off Jane seemed pretty worked up. It was nothing compared to the state I was in, so I didn’t have too much sympathy for her. After verifying the coast was still clear, we snuck out and I went down to my room and got dressed.
Once in my room I threw on some clothes and brushed my teeth, then just sat and closed my eyes, enjoying some quiet time to myself. I must have dozed off for a moment as the knock on my door startled me awake. Jane was dressed casually in black jeans, sweatshirt, and a jacket, but I still thought she looked amazing. Neither of us had a car on campus, so our options for entertainment were pretty limited, especially since she wasn’t 21 yet, so we couldn’t even hit the campus bar. We decided to head to the student center to see if anything was happening, but in the lobby of our building Jane ran into a friend that was heading up and they began chatting. She seemed familiar to me, but I couldn’t place it, and just assumed I had seen her in passing before since we lived in the same building. After waiting patiently for a few minutes, Jane finally said to me, “Oh Victor, you remember Becca, right?” I froze and turned bright red. Of course she was familiar, but I never saw her before, I only heard her voice. Last night while I was naked in the hallway.
Becca spoke before I could even move, “Don’t worry. I almost didn’t recognize you either. You look a lot different with your clothes on.” That broke my paralysis as I looked down, no longer able to maintain eye contact. They both laughed at how uncomfortable I was. “Oh lighten up, I’m just messing with you. Besides, I told you I liked your cock. That was a compliment!” They laughed again. I was still embarrassed, but I have to admit that was nice to hear. She turned back to Jane, “Hey if you guys are looking for something to do, I’m having a few friends over. Not really a party, just a handful of people hanging out, maybe have a few drinks, watch a movie or something. Wanna come?”
That was the last thing I wanted. I’m still too embarrassed, plus I was looking forward to spending time with Jane that wasn’t just sexual, but she had other ideas, “Sure, sounds fun.” So instead of going out, we went back upstairs. First to my room to ditch my jacket and grab some beer from my mini-fridge, then to Jane’s to do the same. As we walked down the hall I couldn’t believe how nervous I was feeling. Obviously I don’t consider myself an exhibitionist and prefer to keep my kinky escapades private, but I’m starting to worry this entire floor now knows about me! Once we got to her room and inside I met her roommate, Michelle, and began to relax for a bit as everyone settled in and began talking. Just normal, boring college chat.
A few minutes later there’s a knock at the door and two more women came in, Denise and Tara. Becca asked, “I thought you guys were bringing your boyfriends?”
Denise explained, “Jack had to go back home for the weekend.”
While Tara rolled her eyes, “Frank is doing some stupid frat thing. I’m getting pissed just thinking about it.”
Becca laughed, “I told you not to mess with those frat boys. They’re nothing but trouble. You gotta find yourself a guy like Jane did. Oh right, let me introduce you. You guys know Jane, well this is her slave boy, Victor.” I almost spit out my drink while the two of them stared at me, confused.
Michelle exclaimed, “Wait, is this the guy you found naked in the hall last night?”
Not sure if I went beet red for pale white. Either way I just wanted to get the hell out of there. I looked to Jane with wide eyes. Luckily she came to my defense, “C’mon guys, leave him alone. It’s none of your business what we do.”
But Becca wasn’t buying it, “Nah, not when you leave him in the hallway like that. But fine, I’ll drop it for now.” It took a few minutes, but I began relaxing again as the topic was changed, but I was still getting the occasional odd look from everyone. Eventually those stopped as well as we all got a few drinks in us and everyone really loosened up.
It was maybe an hour later when Denise asked me, “Okay, this is killing me. Why the hell were you naked in the hall last night?”
Before I could even think of a response, Becca jumped in, “Oh, you should have seen him, girls. Buck naked, blindfolded, hands cuffed behind his back and his cock...damn! First he has a really nice, big cock and it was so fucking hard! Honestly, Jane, I’m kinda jealous!”
While I was looking for places to hide, Jane had a look of pride to her. As everyone began peppering us with questions she told them all how we met, and in more detail than I would ever dream of sharing how we got to where we are now in our relationship. Meanwhile I kept drinking my beer and refusing to make eye contact with anyone else. Worse of all was how my cock was again betraying me. Instead of shrivelling up and hiding with the rest of my body, it was hard...achingly so. I hoped between my jeans and holding my beer in my lap that no one would notice. Tara was a bit incredulous, “Wait a minute, you mean to tell me you guys have been fooling around for two weeks and he hasn’t cum once? Bullshit! I can barely get guys to wait two minutes!”
Becca again relished in embarrassing me, “Well that explains that big bulge in his pants now. Poor guy’s probably going crazy trapped in a room with five women talking about sex.” Now all eyes were on my crotch as I squirmed in my seat and tried my best to conceal it.
Michelle asked, “Is it wrong that I want to see it? Am I the only one or maybe I had too much to drink.”
“I mean, not really, but I still don’t believe any guy would jerk off and not cum. I still call bullshit on that.” I was hoping Tara wasn’t expecting a demonstration, or that Jane would go along with it, but after last night I had no idea what to expect.
Denise chimed in, “It’s not that big a deal. I tease Jack all the time. I mean, not for days, but I make him wait for a few hours sometimes. Of course I never show him off like Jane does.” Both her and Jane shared a smile as everyone else turned to Denise in surprise and began asking her questions, mercifully taking focus away from me.
Unfortunately, Tara wasn’t buying it, “Sure, fine, but at the end of the night he knows you’re going to make him shoot. But if you decided not to and then he went home, what do you think would happen?”
Laughing, Denise replied, “Oh, he’d be whacking it on the car ride home!”
Everyone joined in on the laugh, to which Tara replied, “Exactly.” She then addressed me, “So c’mon, be honest. You really didn’t jerk it when you’re alone?” I assured her I hadn’t. “Tell me why not. I’m still not sure I believe you.”
I took a deep breath, preparing myself to address the four sets of eyes that are currently judging me. Before I can answer, Jane cuts in, “Because I don’t want him to and he wants to make me happy, right?”
I smile, thankful that she saved me from a rambling and probably even more embarrassing answer, “Right. Exactly.”
As if to prove her point, she kicked off her Mary Janes and put her feet in my lap, “Why don’t you be a sweet boy for me and massage my feet. They’re a little sore.” Without a word, I set my beer aside and began rubbing them, hoping this would appease the others and that this was as far as we’d go tonight.
Tara broke the silence, “That does it. I’m dumping Frank tomorrow.” After another group laugh, and a few more random questions, the conversation thankfully drifted away from our unique relationship. However, I never stopped rubbing Jane’s feet, and the one I wasn’t massaging was gently, yet forcefully, pressing into my erection, ensuring it wasn’t going away anytime soon. A few times one of the other ladies tried to convince Jane to get me to perform some other slightly humiliating trick for them, but thankfully she refused saying she doesn’t want to share me with anyone else tonight.
Some time later it was getting late and everyone decided to leave. Jane was a little drunk and had to rely on me to walk her down the hall to her room. Once inside she begins kissing me and we start removing each other's clothes. In between kisses she tells me, “I’m sorry if that was too embarrassing for you, but I thought it was really cute how flustered you were getting. For being such a good boy, I promise we’re going to spend all day tomorrow draining your balls. Sound good?”
I was ecstatic, “Oh my god, yes, that sounds great!”
She giggled, “Good, but for tonight I want you to fuck me for as long as you can.” Once we were naked and in bed I did just that. We went slow, and while I lasted longer than I expected, it still wasn’t very long. When I knew I couldn’t take anymore I slid under the covers and finished what I started by using my mouth. After she came I crawled back up next to her and we fell asleep in each other’s arms. Well of course she did right away and I joined her eventually.
The next morning I woke up first. I assumed Jane was still sleeping off her drinks from last night. I felt like a kid on Christmas morning and couldn’t wait for my present to finally be unwrapped, but worried if I woke her too soon I could ruin it. So I slipped back under the covers and began slowly and softly kissing and licking her. I figured if I woke her up with another orgasm I’d be easily forgiven. It took some time. At first she began moaning in her sleep. Maybe she was having a sexy dream like I had when I was in her position. A few moments later she woke up but seemed a little confused, but didn’t take long for her to grasp the situation, and my head, as she held me firmly in place until she exploded with a powerful orgasm. Once she calmed, I crawled back up to her, “Good morning.”
She smiled, “It certainly is! Someone is ready to start the day.“ I could only give a big cheesy grin in response. “I’m starved, let’s go get breakfast.” My rock hard cock and grumbling stomach were in disagreement with the idea as I got up and threw my clothes on. As we sat in the cafeteria eating, Jane spotted Becca and Michelle and waved them over to us. They both looked tired. I’m guessing everyone drank more than me last night since I stopped once I had Jane’s feet in my hands. Now that everyone was sober and a little hungover, they weren’t as bold or interested in me and my kinks, thankfully. But when they asked what we were up to today, Jane made up for it, “Well Victor was such a good boy last night, I think he finally earned a reward.”
Becca looked over at me, “So that’s why he’s the only one who looks awake.” I don’t know if they were doing it intentionally or if I was just impatient, but breakfast seemed to drag on as they all continued to talk about god knows what. The conversation felt like it was never going to end, but I wasn’t dumb enough to try and rush anyone, as much as I wanted to.
Jane then leaned over to me and whispered, “Why don’t you clean up everyone’s tray and then we can go back upstairs.” I practically leapt out of my seat and offered to clean up for everyone, quickly stacking everything on one tray and bussing the table for them. I was oblivious to their giggles or comments, all I cared about was finally emptying my aching balls. A few minutes later we said our goodbyes and went back to Jane’s room. As soon as the door was closed I began stripping out of my clothes, but to my surprise Jane stopped me, “You’re gonna hate me, but I’m still really tired and need to take a nap. Why don’t you go back to your room and I’ll call you in a couple hours, okay?” I couldn’t hide the look of disappointment on my face, “Aww, my poor sweet boy. I’ll make it up to you. I just need to be awake to do it! And I won’t even make you tease yourself. Go play a game or do some reading or whatever. I’ll call you in a bit.” Grudgingly, we kiss our goodbyes and I slowly begin making my way back to my room.
As I close the door and turn down the hall I see Becca and Michelle heading towards me on the way to their room. Becca called out louder than I wished she did, “What happened, slave boy? Thought you were getting your big reward. Were you a bad boy?” I explain to them that Jane needed a nap first.
Michelle’s eyes sparkled a bit, “Oh, so you’re still all backed up? Why don’t you hang out with us while you’re waiting?”
That sounded like a bad idea, “Oh, uh, I dunno, Jane said…”
But Michelle cut me off and knocked on her door, “Hey Jane, can we borrow your boytoy for a bit?”
She opened the door, “What the fuck, guys?”
“Hey, sorry, but can we borrow Victor while you’re napping?” Michelle asked.
“What? No. Get out of here. Leave the poor guy alone.”
“Oh c’mon. You’ve already shown him off to your other friends and I saw him the other night. What’s the harm if he hangs with us for a little bit. We can make sure he’s all warmed up for you when you’re ready.” Wait, was she actually considering this? I pleaded to her with my eyes to not let Becca’s argument persuade her.
Jane rolled her eyes, “Fine. But no touching! Next time find your own toy. I’ll call you guys after my nap.” The girls were giddy as they began walking to their room while Jane told me, “I know this wasn’t what we had in mind today, but I find it kind of hot lending out my slave. Now be a good boy and do whatever they want, as long as no one’s touching each other and you don’t cum, got it?”
Defeated, I replied, “Yes Mistress.”
As Jane gave me a goodbye kiss Becca shouted down the hall, ‘C’mon, slave boy, let’s go!” I sighed as I walked after them. As soon as we got to their room Becca asked, “What did Jane tell you?”
Embarrassed, I replied, “Umm, she said to do whatever you say as long as there’s no touching and I don’t cum.”
“That’s fine with me,” Michelle said, “I just want to see this cock everyone was raving about last night. Okay, strip!” I sighed again as I slowly took my clothes off. As embarrassed as I was, I had to admit this was turning me on. I wasn’t sure if it was Jane loaning me out as if she really did own me, stripping in front of two very pretty college girls, or the fact I’ve been teased mercilessly for the past two weeks. Whatever it was, by the time I was naked my cock was standing at full attention. Michelle wolf whistled at me, “That is nice. Okay, give us a show. Stroke it nice and slow to the edge for us.”
Hesitantly, I grabbed my cock and began stroking at a slow and steady pace. I closed my eyes to at least pretend I was somewhere else, but Becca wasn’t having it, “Uh-uh, eyes open. Look at us while you do it. Don’t you think we’re pretty?”
“Of-of course I do. You’re both beautiful.” Then to my surprise they both stripped out of their clothes down to their bra and panties. That caused me to stroke a little faster and a couple minutes later I had to stop. I put my hand at my side and stood there panting, right on the edge of orgasm.
“Damn. Okay that was impressive. What do you think Beck, seen enough?”
Becca thought for a moment, “Yeah, but I hate to waste a perfectly good slave.” She snapped her fingers, “I know, why don’t you clean up our room for us. After all, you helped make this mess last night, seems only fair. I have some reading to do anyway.”
“Yeah, me too. Great idea. Okay Victor, hop to it!” They put on some music and each layed out in their bed, still dressed only in their underwear showing off their sexy bodies to me as they read. I couldn’t help but ogle them as I slowly began cleaning up around the room. After around five minutes, Michelle said to me, “Why don’t you take a break and edge again for us?” So I stopped what I was doing and stroked myself, same as before, until I was right on edge again. For about an hour I alternated between cleaning and taking “breaks” to edge again for them. In my head I was praying for Jane to wake up and call for me.
When I was finally finished with their room, Becca told me, “Wow, nice job. Thanks. Bring that chair over to my bed and sit down”. After I did she repositioned herself on the bed so her feet were resting on the chair, right between my legs. “That foot massage you gave Jane last night looked awesome. Now do me.”
I hesitated, “But Jane said…”
She cut me off, “I know, but pretty sure she meant we can’t grab your cock or sit on your face or whatever. This is sooo innocent. Hell, you did it in front of all of us last night and no one thought it was obscene.” I had to admit she had a point, so I held one of her feet and began rubbing it. What I didn’t expect was her other foot to begin lightly grazing my cock as she slowly moved it around. I couldn’t help but gasp and moan as we continued to rub each other. After several minutes she had me switch to her other foot, but she continued teasing me.
Not too long after that Michelle spoke up, “My turn! Bring that chair over here.”
I looked up at Becca who simply nodded and if I didn't know better I think her panties had a small wet stain. As I moved the chair to Michelle’s bed, Becca got up and grabbed a towel, “I’m uh, going to go take a shower.”
Once I was settled Michelle gave me her foot and we gave each other the same treatment, except she was a little more aggressive with her foot on my cock, almost gripping it with her toes. As soon as Becca left the room she told me, ‘She’s totally going to whack it in the shower.” After a few seconds of my massaging, she said, “Oh, and I can see why. This is nice.” She closed her eyes and began running her hands on her body. Starting on her stomach and slowly up to her breasts, making her nipples hard through her bra. Up and down they went, until a few minutes later when she had me switch feet, then she let her hands drift lower until one went under her panties and began rubbing herself. Her foot was rubbing me a little faster as the hand in her panties did the same. Between her more forceful foot and the fact she was masturbating right in front of me, I was getting close to cumming myself. I tried to concentrate more on the foot in my hand instead of the one on my cock, but luckily (or unluckily?) for me a couple minutes later she pulled both her feet away from me and onto her bed as she rubbed herself to orgasm. I could only sit and stare as my cock bobbed in midair, yet again fooled into thinking this would be the time he’d cum.
Becca came back in soon after, “Jesus, Chelle, I could hear you in the hall.”
Michelle’s face was red, either flushed from excitement or embarrassment. Maybe a bit of both. “Think I’ll grab a shower, too.” She grabbed her towel and toiletries and was quickly gone.
“Okay perv, I think the fun’s over. I’m not getting changed in front of you. Why don’t you head back to your room. I’ll let Jane know where you are when she calls.” I quickly grabbed my clothes and got dressed before she changed her mind. Becca gave me a peck on the cheek, “Thanks Victor, that was fun. Maybe Jane will let us borrow you again sometime.” I awkwardly smiled and left.
Once back in my room I layed on my bed, staring at the ceiling, wondering what the hell was going on. I’m pretty sure I’m the luckiest guy on campus right now, but this whole experience has been so unbelievable. I begin wondering if it’s all a dream or delusion. My sore cock and aching balls are the only things convincing me this is really happening. Next thing I know my phone is ringing, waking me from a peaceful sleep. It’s Jane. As we say hello I glance at my clock to see it’s 2pm. “So, you finally ready to drain those balls?” Honestly, I think I’d rather go back to sleep, but I know I’d regret passing up on finally getting an orgasm. At this rate she’d probably make me wait another week at least if I said no to her now. So instead I said “Yes Mistress,” and walked back up to her room. As soon as I was inside I began stripping naked. It was starting to become second nature now. Jane was wearing the same clothes as this morning She directed me onto her bed. Once there, she pulled out the rope that Heather used the other day and tied my ankles and wrists to the bed frame. After putting a blindfold over my eyes I felt her lightly caress my cock, ensuring it was fully erect, then had me tell her everything that happened with Becca and Michelle. As I recounted the events between gasps, she kept lightly touching me, causing my cock to throb and jump off my stomach. Once I was done she said, “Damn. I should probably be mad at them, but that sounded pretty hot. Did you enjoy yourself?”
I felt like this might be a trap, but went with honesty anyway, “I mean, yeah, sort of. If I wasn’t so tired I probably would have liked it better. It was weird though since I barely know them.”
“Yeah, I’m sure staring at those two in their underwear while they touched your cock and masturbated in front of you must have been real torture for you. What guy would want that?” She laughed at herself. “Would you ever want me to loan you out again?”
I gulped, “You’re right, it was kind of hot you treating me like your property for others to use. And of course they’re both really pretty which made it even easier. So yeah, if that’s something you wanted to do, I’d be okay. As long as it doesn’t ruin what we have.”
She gave my cock a firm squeeze, “Good answer. We’ll see. But for now, you’ve definitely earned a reward for being such a good little sex slave for me. Denise and I chatted a bit last night and I’m dying to try something she told me about. We’re going to wring every last drop of cum out of you. Ready?” I wasn’t sure I had a choice at this point so told her I was. She stopped touching me and got off the bed. Some music began playing and I could barely hear her shuffling around the room. Every now and then she’d come over and give my cock a few strokes, keping me rock hard, while she did whatever it was she was doing.
After several minutes she removed the blindfold and once my eyes adjusted to the light I saw she had changed. “Holy fuck! You look amazing!” She was all in black, starting the same pair of knee high, platform boots I saw the other day that led to stockings held up by a garter belt. A pair of panties and a lacy corset, teddie completed her ensemble. She also put on some makeup giving herself her signature ruby red lips which were a sharp contrast to her light skin and jet black hair that was framed perfectly around her face. She was the embodiment of sex, casuing my cock to jump at the sight of her.
She smiled and slowly walked towards me. My heart was racing faster with every step she took. When she sat down next to me and took my cock in her hand I thought my heart was going to explode before my cock could. “Okay. Are you ready to have your balls drained?” I smiled and nodded like an idiot, because let’s be honest, at this point I obviously was one. “Good, but you still need to ask for permission before you do. Here we go.” Slow and steady she began stroking me. Despite the fact that we’ve done this countless times in the past week, this time felt better than the others knowing I was finally getting my overdue orgasm. She studied my face as I admired her body in that outfit as she brought me closer and closer with each stroke.
“Oh fuck, I’m getting close!” I couldn’t believe this was finally going to happen! “Oh yes! Can I cum, Jane? Please?”
She smiled, “Not yet, what’s my name?”
Shit! Fuck! “ Mistress Jane, please can I cum?!?”
She smiled wider, “No. I changed my mind.” My eyes were saucers and my mouth dropped open in shock as she let go of me. I wanted to yell, scream, and cry. Instead I was speechless as I struggled to free my hands, but it was futile. After letting me stew for a minute she laughed and began stroking again, “Just kidding. Can you imagine? What kind of cruel bitch would I be to do that to you? Damn, you should see the look on your face! I’m sorry babe, that was mean, but I couldn’t resist.” I sagged into the bed and relaxed a bit. I’m sure to anyone else that would have been funny, but to me it was cruel and unusual punishment. I would have stayed mad if not for the fact she had me close to cumming again. It wasn’t long before I was begging for permission, thankfully, this time she said, “Of course, my sweet boy. Cum for me!”
Her hand moved slower and slower, but still enough to drive me over the edge. Finally, it was happening, I was past that glorious point of no return and yelled out, “Oh fuck, yes, I’m cumming!” And just like that she let go of me! I looked down at my cock in shock as it throbbed and bobbed and after a few seconds I watched as a small stream of cum dribbled out. I came, but not really, and somehow I felt even hornier and more frustrated than a few minutes ago. I began babbling, “What? Why?”
“Denise told me about this.She called it a ruined orgasm and said she does it with her boyfriend sometimes. This way she can make him cum over and over again because he stays hard and horny. What do you think?” What did I think? I think I’m going to lose my mind! I think she’s cruel! I said none of these things, I simply struggled in my bonds again, desperate to get my hands on my cock and finish the job. “Yeah, that’s why I wanted to tie you down. She warned me you might react that way.’
I finally found my voice, “Please let me cum? Fuck! This is too much! Please? I can’t take it anymore!”
She hushed me by first kissing my lips, then going down and cleaning up the small mess I made with her tongue. “Just relax, babe, we have all day and I promised I was going to drain you. But make sure you ask for permission each time. If you try and fool me I’m going to be really pissed, and remember you’re still tied down.” And that’s how we spent the afternoon. Again and again she ruined me, ensuring just a small amount of cum escaped each time. Sometimes only a couple drops came out. It was maddening! She went from her hands to her mouth. After removing her boots she used her feet one time since, “You seemed to enjoy it so much from those girls earlier.” After each ruin she would give me a minute to calm and then use her mouth to clean up anything that came out. After a couple of hours and who knows how many times, I was a complete mess. Instead of an orgasm, I began begging her to stop. I couldn’t take anymore. She looked at me with concern, “Uh oh, did I break my toy?” I nodded. “Okay, why don’t we rest for a bit then I’ll make you cum for real, would you like that?” Unsure if it was another trick, I slowly nodded again. She got up and grabbed a glass of water, letting me drink from it slowly. Once done, I rested my head back and closed my eyes. Happy for the break.
A few moments later I could feel Jane getting on the bed with me. I opened my eyes just as she laid her body on top of mine. We began kissing, it was sweet and loving. After a few minutes she stopped and looked me in the eyes, “I know this has been a crazy week, but I really liked it! A lot more than I thought I would. Who knew having a sex slave could be so much fun! I really hope it lived up to your fantasies and you want to keep doing this, because I have a few more ideas for us to try. After today we should probably take a small break so you can recuperate. What do you think?”
As I thought about it, this was exactly what my fantasies were. In each moment, including my current one, all I wanted was for it to end, not believing I could take a second more of whatever was happening to me. But looking back at each scene now and what she put me through was such a turn-on and I found myself wanting to do them all again. Even the ruin marathon she just put me through. I put these thoughts into words as best I could, “Just about everything we’ve done has been absolute torture, but it’s also been the best week of my life. I want to be your sex slave for as long as you’ll have me.” She smiled wide and we began kissing again. Soon she slid my cock inside of her. I guess her panties had come off at some point.
She sat up and rested her hands on my chest while she rode me, “Don’t forget to ask permission!” All those ruins really did a number on me, as I lasted a lot longer than I thought I ever could. Jane had already cum once on me and was showing no signs of slowing down. A few minutes after she did, I finally found my own orgasm approaching. I begged her to let me and not ruin it, she replied, “Yes, but hold back for as long as you can! I want you to cum for me my sweet boy!” So I did. I struggled and strained holding in two weeks of pure frustration until it could no longer be contained and I exploded in the greatest orgasm of my young life! I wasn’t even sure if I had any more cum left to give, only that my body was releasing a ton of built up tension and finally able to relax. The only problem now was Jane. She wasn’t stopping. Right after an orgasm, a real one anyway, my cock gets incredibly sensitive. Like please don’t touch me I’m going insane, sensitive. And here was Jane still riding away and it was immediately unbearable, but I was powerless to stop her.
I began begging, “Please stop, too much, please, no more, can’t take it…”
Ignoring my pleas, she continued, “Fuck, no, not yet, I’m so close!” I had no choice but to lay there and endure until she came again a couple minutes later, collapsing on top of me. We both laid there, panting, completely spent. All I wanted to do was drift off to sleep and would have any moment if Jane didn’t force me up and out of bed after untying me. “I don’t know when Heather’s coming back. Help me clean up and we can go to your room and nap.” Reluctantly, I got up and helped. We also opened a few windows and the door to air out the room. I’m guessing it reeked of sex by now.
Once we were done Jane hopped in the shower and I went back to my floor to do the same. Back in my room Jane joined me shortly after and we grabbed dinner and hung out in my room for the rest of the night. We talked about everything that happened, what we liked and maybe didn’t, and what we wanted to do again. That night we literally slept together and it was the best sleep I ever had in my life.
I spent the rest of the semester as Jane’s sex slave and it was six months of bliss, but with graduation and the next phase of my life staring me in the face, I became sad. Even if we stayed together, I knew we wouldn’t have nearly as much time together as we did, and I wasn’t even sure if she wanted to try and maintain our relationship once our lives took us apart. But on my last night in the dorm she gave me a graduation gift and I knew my fears were unjustified. Inside the little box was a chastity device and around her neck was a new necklace with a key attached. She helped me put it on and locked it shut. After a deep kiss she told me, “You didn’t think I was going to let you go that easily, did you? You’re my slave boy and I’m not letting you forget it!” I spent my last night as a college student with my face between her legs as she reminded me over and over that I belonged to her. Each time she did my cock swelled in its new prison and I couldn’t be happier.