Everything had been going great. Heather and I had been, I guess, the typical sweethearts – although I'm not quite sure how I got to be that lucky. She was one of the more popular girls at school and I was more of an average guy. I wasn't a geek but I was certainly no jock, and I never thought that she would think of me in a romantic way until we had a few classes together early our senior year and started going out. Things took off really well and we decided, not coincidentally, to go to the same college. It was the next state over, but we would only know each other when we got there. We both got random roommates but lived in the same building and saw each other every spare moment, spending a lot of time in each other's rooms.
I think this is where the problems began. We had always spent a lot of time together, but not every spare waking moment. Also, back home, we had other friends to hang out with, that wasn't the case at college – we only knew each other. The second problem was probably my own entirely. I was a compulsive masturbator. Heather and I fooled around sometimes, but it was never ever enough for me. My sex drive seemed insatiable at times and I had to get off at least once a day, sometimes more. Needless to say, Heather was disgusted and played the usual cards, “Aren't I enough for you?” and, the classic, “You think I am ugly, don't you?” Of course, I thought she was the most beautiful thing on the planet, but that never stopped me from getting off on the side. After awhile, she had had enough and, after a big fight, made me promise that I would stop. I honestly tried, for a day, but then I was right back at it hoping she wouldn't catch me. Inevitably she did and was absolutely furious. She threatened to break up with me and when I said that I would do anything to keep her she could only say that she would think about it. For the first time since we started going out we didn't talk for a few days. I am the one who broke down and called her, left her notes and knocked on her door – she ignored it all and I was lost.
Finally, after a week of complete misery she called me. She said she had been doing some serious contemplation and she couldn't shake the fact that she still loved me. But she also couldn't shake what she referred to as my “disgusting habit.” She had given me a chance to stop and I had failed, obviously I couldn't be trusted. She had been trolling the internet looking for solutions to her problem and finally came across one that might work – a male chastity device. At first I really didn't understand, the idea was foreign to me, but she casually explained that I would be locked up, she would hold the key, and I would only be let out when she allowed it. At first I couldn't think thought the haze, but then I realized that I was infatuated with her and would do anything. I agreed. About a week later we received a package in the mail. That night I got locked up for the first time and she took the key and went back to her room. I had begun a life of chastity.
Things stayed like this for awhile. I was locked up and at her mercy. Occasionally she would unlock me so we could fool around and I would get a handjob or a blowjob out of it. And a few special times we would have sex with a condom. She would also unlock me a few times a week when I took a shower so I could clean myself. I would always end up in the shower with an erection just because I wasn't getting off as often as my sex drive seemed to require. But she would always be near by to make sure I didn't try anything. The worst part was that it was impossible to get the chastity device on my cock when it was hard – and she didn't think that I deserved to get off every time I took a shower. But she soon had a solution to this problem as well. It became my duty to make sure I had ice on hand whenever I would take one of her supervised showers so that we could get my erection down afterwards without me getting off.
At first I bugged her almost constantly to let me out and fool around with me, but I began to notice that the more I bugged her the less and less anything happened. So I decided to try a new tact. I would bring her flowers, wait on her hand and foot, and always make sure she got off two or three times before I did. I think this is where my next set of problems began. She began to see my chastity as less of a liability and more of an asset. It wasn't long before she was holding the key over me, literally and figuratively, to get me to do things she wanted. Soon I found myself eating her out for hours on end just so she would “think about” giving me a handjob. Her permisterality began to change too. After I had been her de facto slave for awhile, she saw me as less of an equal to her and as not really a boyfriend anymore. She never came out and said these things at this stage, but it was apparent in the ways she treated me and the look in her eyes when she did so. I could tell she was really enjoying it.
Up until this point we had kept all of this a secret to everyone, of course this wasn't really hard because we didn't really know anyone else on campus. This began to change when Heather started to get close with her roommate Jane. Jane was a really skinny, rich girl from down south who loved the party scene on campus – especially the frats. I never did know how that girl kept her grades up. From time to time she would try to get Heather to go out with her, but Heather would always say no because she wanted to spend time with me. However, now the status quo had changed. Heather didn't need to keep me happy anymore, she had real power over me now. So one Friday night she nonchalantly announced that she would be going out with Jane. I was taken aback, but there was nothing I could really do, I was too scared of upsetting her. She said she would call me when she got back to the dorm, but she never did. The next morning I went to her room and banged until she answered, obviously annoyed and obviously hungover. I got the classic “What do you want?” look that spoke volumes about how she felt at the moment. It was Jane, however, that threw me off the most. She was peeking out of her bedroom giggling and I had no idea why. Heather and I got into a mini-fight, which I was only capable of after steaming all night about her not calling me, but Jane just kept getting more and more visibly amused. Finally, I had to ask her what was so damn funny. Then, one of the worst things I have ever heard came out of her mouth; “I know all about that thing you wear and your disgusting habit. Heather told me everything last night!”
I just laid in my bed, in the dark, for a long time the rest of that Saturday. I had yelled at Jane. I had yelled even louder at Heather, calling her things that I so desperately wished I could take back. Heather had slapped me, causing Jane to burst out in a fit of laughter. I cowered back but Heather must have seen the rage boiling in my cheeks when she slammed the door and shouted “We're over!” I now needed to explore my options. After what had happened, reconciliation seemed impossible. I couldn't go to the police, that would be too embarrassing. I was stronger than Heather, could overpower her and get the key from her, if she even had it on her at the time; but that would constitute assault. She could file charges and I could find myself in court and out of school pretty fast. I considered getting the device off, but I had no idea how to do so without hurting myself severely. There was nothing I could do. I was screwed. Things went like this for two weeks – the worst of my life until that point. I saw Heather around, but she would just turn away, unable to even look at me. Jane, on the other hand, would openly laugh at me and even came up to me one time in the dorm hallway. “How are you feeling down there? Are you getting some blue balls? Does your little guy want out? Too bad you're not much of a man or you would never be in this situation in the first place. That's what Heather needs now, a real man.” With that she licked her lips and walked away. I was humiliated, but all I could do was stare at her ass, I was so horny.
I was locked in a chastity device that my ex-girlfriend had the key to. How could I be any more screwed? To make matters worse, Heather and I weren't even speaking and her roommate Jane was openly mocking me. Finally, a glitter of hope arrived in the form of an e-mail from Heather. It read: “Dear caged. We are in an odd situation, as I am sure you have noticed. I would like to propose a solution. If you would ever like to get relief again I hope you will agree to it. We will no longer be boyfriend and girlfriend. In fact, you will be my servant. I will still hold your key, but you will be allowed out to do that nasty thing you do, but only when I feel like it. To make me feel like it, I suggest you should do everything I want to the exact detail. Also, I feel I should let you know that I will be dating again, and I want no interference from you. You, on the other hand, will not be allowed to date. If you agree, Jane will assist me in keeping you under control. You will also be required to do everything she says. Please reply promptly.” Of course I agreed. What else could I do? About an hour after I replied to the e-mail my cell phone rang with a text message. I expected it to be from Heather, but instead it was Jane. “Get over here. Now,” was all it said.
Needless to say, I didn't hesitate. When Jane opened the door she had the biggest grin I have ever seen. “We're going to have some serious fun today, boy.” I got quite nervous and asked where Heather was. “She'll be back in a few minutes, she had to go to the library. Right now you are to come in here, strip down to that (giggle) cage of yours, then put on the things on Heather's bed.” I stripped down quickly, my cheeks red from embarrassment. For some reamister I didn't speculate on what lay waiting for me on the bed – I guess I was too scared. But when I did see what was there, thats when the reality of the situation finally hit me. This was not going to be some simple thing, Jane did really have it out for me. She was going to have as much fun with this as she could. Still, I was under her control. I put on the bra and panties without a word.
Up until this point I assumed that I would succumb to some offense from the girls then I would be able to get my rocks off, but Jane soon shattered that idea too. “This room is a mess. You are going to clean it while I watch TV.” I hesitated, but only because I thought the closet door moved a little. Jane saw me look and laughed. The door then swung open and I was startled by several flashes. Heather was taking my picture! I didn't think it was possible to be any more embarrassed than I was, but that proved very wrong. “We need some insurance, you see,” Heather said. “We are going to let you out of that thing at some point, and we don't want you running off when we do. These pictures should ensure that you stay ours for as long as we want. That is, unless, you want everyone you know to see proof of your, um, more private habits.” Both girls for a big laugh out of that, I stood silent. “Well, what are you waiting for? Start cleaning. While you do, we are going to lay down some ground rules. First, you will address us both as 'Miss.' You will speak when spoken to. You will do what we say without hesitation. You will worship the ground we walk on.” (The last part being added by Jane, but I could tell by Heather's smile that she certainly agreed.) “Is that understood?” asked Heather. “Yes, Miss Heather... I understand.” I think it goes without saying that I was terrified.
“Alright Jane, unfortunately I have a quiz tomorrow, so I have to go study, but you stay here and keep having fun with the boy.” With that laughter erupted as Heather left. Jane kept watching TV and I kept cleaning. Finally, when I had finished to Jane's approval, I was ordered to kneel before her at the couch. “Heather did say that you are good for one thing at least,” she said she she casually slipped her panties off out from under her skirt. “I think you know what I want, get that tongue in there.” Surprising even myself, I drove my head under her skirt rather quickly. I think that the absence of any sexuality in my life over the past few weeks made me desperate for anything, even if it was getting someone else off. She kept watching some show on MTV as I did my best to make her happy. At first, she seemed to ignore my efforts, but soon I could taste her getting wet. Not long after, she grabbed my hair, pushing me deeper. Her moans blocked out the TV and I could tell she was on the verge. “Don't you dare stop, even after I come. You are my little bitch-slave and I am going to make you eat my pussy until you agree to worship me as your goddess.” Normally, that would have thrown me off wildly, but she was pushing me in and I was much too scared to stop, especially after that comment. Clearly, this girl had problems. “Do you understand me?” she yelled? Did she expect me to be able to answer? I mumred and groaned some things as I kept licking and that seemed to satisfy her. I wonder if Heather knew how crazy her roommate was? But then I realized that I was the one wearing a male chastity belt, a bra, and panties eating out my ex-girlfriend's roommate. The pot shouldn't call the kettle black.
After an hour or so, Jane let me stop. When I pulled my head into the light, finally, Jane looked as if she had been in a hurricane. Obviously, she had enjoyed my efforts. “That was... adequate,” she panted. “Let me get your key.” Finally, a sign that what I had been waiting for was about to happen! Sweet relief... I couldn't wait. Jane took a chain off from around her neck, the same one that Heather had used, and handed it to me. “You can take it off, but don't try anything funny, don't forget about the pictures.” At this point, I didn't care, my hands were shaking as I put the key in and turned. My cock immediately sprang to life. Jane had her eyes closed, opened them a little, then very wide all of a sudden. “Oh. My. God. You have to be kidding me,” she said. I didn't understand what she was saying or why she was staring so intently at my penis with a small grin on her face. Then Jane corrected my ignorance, “that's all your packing? I've seen babies that were better endowed.” She then broke out in one of her trademark fits of laughter. I stood there, stunned, remembering that I was not permitted to speak unless prompted. “Wow, boy. Heather never said anything about this, although I don't know how she could have left it out. Could it be that she doesn't know any better? I know that you are the only man, or boy I should say, that she has fooled around with. I can't believe she thinks that's the size a man's tool is supposed to be. I have got to get that girl properly laid.” For the first time since I was a little boy, I thought about crying. But what happened instead was even worse. I shot my load all over the floor, never having touched it after Jane started talking, and her next words were practically crippling in their truthfulness: “On my god! You like it!”
Things went on like this for awhile. I would be told to go to Heather and Jane's room where I would do some cleaning or some other chore then eat one or both of the girls out. Sometimes they would let me get off, but that usually involved Jane laughing hysterically at my “baby penis.” The most embarrassing incident occurred when Jane made me stand naked with my erect penis (I am longer allowed to call it a “cock” or a “dick” because Jane says its not big enough to qualify for either of those terms) by her laptop. Jane then went to a few porno and permisteral site where she showed Heather “how big a real cock is.” All Heather could do was stare, mouth agape, at each new guy Jane pulled up. Then she turned to me, obviously angry, “I can't believe you have been depriving me of all this for so long! Why didn't you tell me you were so small? Jane, we are going out this weekend and I am picking up a real man.” Jane laughed, Heather smiled, and I shot my load all over the floor.
The day I had been fearing all week had arrived. It was Friday and Heather and Jane had plans to go out that night. I was ordered to be at their room at precisely 8 pm. When the door opened, I was greeted with a vision of beauty. Heather was done up nicer than any time since we had gone to Prom together in high school, though of course she wasn't wearing a prom dress. Jane looked a lot sluttier, but was still one of the sexiest things I had ever seen up close. Both girls were clearly going to be looked at by every guy in any room. The idea of another man being with Heather scared me to death. I had thought everything was going so well, that we would be married. But there I was standing in her room as she prepared to go find another man to give her what I couldn't. Jane broke the silence, “Boy, Heather has expressed some misgivings about tonight because she is worried about how you will react to her relaxing with another man. I have told her this is nonsense because she deserves better and you aren't really even a man, but her misgivings persist. To rectify this, I want you to get on your knees, kiss her shoes and tell her exactly how okay you are with it.” The look in Jane's eyes said that I better not screw this up. I did what Jane had said to do, I kissed Heather's black, heeled boots and made some things up about how I wasn't good enough for her and how I only wanted her to be happy. Jane seemed pleased, and I was more scared of her than anything, so I guess I had done well. With that I was ordered back to my room, the girls had specified that I would not, under any circumstances, try to follow or contact them. They would get in touch with me when they felt like it. I assumed that I wouldn't see Heather or Jane until at least the next night... how wrong I was.
To get my mind off things I decided to watch TV all night, maybe a movie or two. I knew that I shouldn't go out and I didn't really know many people on campus besides Heather and Jane, so entertaining myself seemed the only option. Too bad I was still locked up, the TV was all I had. I had thought I would fall arelax kinda early, but the nervous tension, thinking about what Heather was doing at the moment, kept me awake. At around 2:30 something which I did not expect happened, the door to the common area of my dorm room began to open. Oh great, I thought, James has brought another girl back. James, my roommate, was rushing a fraternity and only spent the night in our room when he had picked up some floozy at one of the bars or his frat house. This had been great when Heather and I wanted to be alone. But it was awkward when he did bring a girl back because his type of girls always seemed to be the loud ones. Going through hearing James and a girl for the rest of the night was only going to make my situation tougher. My mild annoyance soon turned to puke-my-guts-out fear when I saw James back into our room kissing Heather. When they noticed me sitting in the couch James simply said “Boy, I think you had better leave.” The look on Heather's face and the way James had said “boy” told me that Heather had told James everything. I hesitated about leaving, so Heather added “you had better get out of here, I can't wait to get your roommate's pants off... I can feel how huge his bulge is... so much bigger than I'm used to.” That was all I could take, I ran out of the room and almost right into Jane who was in the hallway. “Come one boy, back to my room, you are going to be my entertainment for the rest of the night.”
“Here is your key, take that cage off. But you had better not touch that thing and don't you dare cum,” was the first thing that Jane said to me when we got to her room. Watching me undress, I could tell that Jane was very excited about whatever we were going to do. She was still dressed up for going out to the clubs. Extremely slutty and very, very sexy. I couldn't help but get a hard-on once the cage was off. Jane snickered when she looked at my dick, I could tell she detested its size. “On your knees,” she said. “Are you a man?” she asked. I hesitated, but when she frowned I replied “No, Miss Jane.” “Why not?” “Um.... I can't stop from touching myself?” “That's one reamister,” Jane agreed, “But let me tell you a little more about the other reamister.”
“You see,” she began, “There are two types of males in this world. Men and boys. Men, like your roommate James who is currently giving your girlfriend the kind of fucking she has never had before, and boys, like yourself. Men have confidence, self-control and most importantly, cocks that are better then that little thing. Men are for sex, and boys are for service. You don't deserve to ever have sex with a girl again, you are not a man. James, however, deserves everything your ex-girlfriend can give him. What they are doing right now is the most beautiful thing in the world. You, on the other hand, are disgusting. From now on you are to recognize your place in this world by worshiping all women, especially Heather and myself, as goddesses. From now on we are your everything. Tonight we are going to confirm this. Tonight I am going to make you my bitch.”
On my knees, looking up at this beautiful girl dressed like a slut, telling me these things, I couldn't help but cum all over the place, even though she had told me not to. Right away, after my last spurt, Jane grabbed my hair and shoved my face into the mess on the floor. While she yelled about how worthless I was she made me lick it all up. I was soon quite hard again. I didn't want to like this use, I really didn't, but apparently my body couldn't help it. Jane stripped down to her bra, telling me about how I wasn't worthy of seeing her tits. She made me crawl over to her. She then guided me, minute by minute, through a permisteral pleasure massage. I started on her feet while she played with her clit and rubbed her breasts through her bra. I couldn't help but look up, she looked so beautiful and all I wanted to do was kiss her and nibble on her earlobes like any real man would have certainly gotten to do. But I realized that I would never get that pleasure. Luckily she was enjoying herself with her eyes closed, so I didn't get in trouble for paying attention to her and not her toes. She then made me move on to her inner thighs, which she really enjoyed. She started moaning and I couldn't help but feel a sense of pride. I may not be a real man, but I can make this beautiful girl moan. I still had a place in the world.
About an hour later, after Jane had three orgasms and nearly pulled some of my hair out she put her panties back on. Once again, she looked really flustered, I could tell I did a good job even though she would never tell me so. I had had a raging hard-on the whole time and I was really hoping to get off again. Twice in one night would be unprecedented since Heather and I stopped dating. Jane went into the bathroom and I waited obediently on my knees. She came out wearing some knee-high leather boots, which Heather must have told her I absolutely love, and then started looking through the closet. She was saying some things about how worthless I was but all I could think about was how I was falling in love with this girl. She was everything I never knew I wanted. She was my goddess. I had succumbed to her plan. Little did I know that she meant the part about making me her bitch quite literally. Still in my haze, I didn't even see her putting something on over her underwear around her waist. What I didn't miss was her turning around and seeing a dildo swing in front of my face. My ears started ringing, I got a little sick in my stomach realizing what might be about to happen, but I still heard her say, “Suck it, bitch.”