Dorm Room Domme
Posted: Sat Jan 30, 2021 1:29 am
This one is loosely based on real events, but of course it quickly spins out into fantasy. Started this a long time ago, then made some headway a couple years back and stalled again. Finally got the motivation to finish this past week. Funny how easily the story can flow out sometimes. Anyway, a few caveats and other random notes on this one. First, there is some pain and ballbusting, so if you’re not into that you are warned. Overall this is a rambling, unrealistic mess of a wank-fest set in a realistic world (no magic or supernatural stuff) that includes a possible problematic scene in the middle I probably should take out but didn’t. You’ll know it when you read it. And of course, we assume everyone is practicing safe sex even if it isn’t explicitly implied. All that being said, I still kinda like it and want to be the protagonist. Hope ya’ll enjoy, despite its warts.
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…”
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…”
