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My college roommate, although a pretty smart and cool dude when sober, was an annoying alcoholic – to the point of blacking out. The first few weeks of fall term were hell because of him. Through some miracle he’d get through classes, get his s*** done for studying/assignments, then proceed to drink himself stupid and manage to annoy the s*** out of me. After a few weeks of it I decided to get my jollies/revenge by molesting his a****** while he was blacked out. I didn’t want him to notice due to any pain or discomfort and as a gay dude I was well aware if I took my time his a****** would learn to open up.

I spend the rest of fall term working on his a******, at first just r****** and slowly f******** it while I jacked off. It was very resistant at first and I was sure he’d wake up sore and wonder what the f*** happened, but he never did. Once his hole could take one finger I also began to jack him off during my exploration. It was wild watching his body learn to enjoy the a*** stimulation. Over the next many weeks, I coaxed many loads out of him c*** by sucking his c*** and balls while I fingered his a******, learning how to massage his prostate to force him to c**. I managed to resist using my c*** on his hole, although I was incredibly tempted to just do it. I promised myself that if he came back from Christmas break and we were roommates again, I’d reward myself with taking his a** cherry with my c***.

I was a little worried after the first couple of days of spring term. He only had a couple of beers, watched TV, played games. By the third night he was back to his old tricks again, cracking open beers by 3pm after his last class and drinking like a fish. My d*** was leaking precum a little more every time he’d pop another beer can open. Hell, I even encouraged him and drank a little…mixing in some shots of Jack Daniels to encourage him. By 10:30 or so, he was in a coma and drooling on the floor. Being a little skinny s***, he was easy to pick up and carry to his bed – I was very used to this by now and VERY excited to have him helpless for what was coming.

My d*** was rigid and eager to f***, but decided since it had been a few weeks since I’d opened his hole I needed to prep him first. As i’d done over weeks in fall, I started by lifting and spreading his legs and eating his a** first. I’d missed this furry hole for so long so I licked on sucked on it eagerly. I took some time too, to appreciate how different his a****** looked compared to the first time. It had been a tiny little b******* at the beginning of fall term but his hole had grown some and looked bigger. His c*** remembered all my work, too – his c*** was waving around and flexing. I sucked on it after I got his hole wet with spit, and began working the first finger into him. I was a little worried about how hard he was and the way his c*** was flexing while I fingered his hole. I didn’t want him to c** yet, so slowed down and concentrated on his a******, sucking him only enough to keep him hard. He opened up fairly easily and I began working two fingers in and also looking for his prostate. Soon, drops of precum were oozing from his c*** and I knew he was ready.

I stripped my pants off and fetched the lube I’d been carrying in them for this momentous occasion. I worked the lube into his a****** liberally and stoked my c*** until it was slick and wet, too. I got into bed between his legs and raised him to shove a pillow under his a**. After so many weeks and months of waiting, having my rock hard c*** pressed against his a****** was heaven.

I pressed my d*** against his a****** and stroked his c***, wanting him to stay hard while this happened to him. I humped against his a****** and was thrilled to feel his c*** flex in my hand while I did. So slowly, imperceptibly at first, my c*** inched its way into him. That’s when I remembered I’d intended to wear a rubber. I didn’t want him to wake up the next morning and fart my load out of his newly fucked a******. It was too late, though. I couldn’t bear the thought of pulling my c*** head out of him, so I kept pumping it oh so slightly.

I thought he would wake up when the head finally popped past his sphincter. His a****** clamped down on my d***, his legs were squeezing my waist, and he moaned – which was rare. His blackouts were normally pretty coma-like, and my mind started racing with what I’d say if he did. I decided to ride it out and pretend to be drunk as well – no homo, dude! He settled pretty quickly though and relaxed again. I could feel a heartbeat where we were joined a****** to cockhead, but couldn’t tell if it was his or mine.

I took the opportunity to coax his c*** back to erection, and once he was flexing happily in my hand again resumed pumping against his hole. i began withdrawing my c*** some and immediately pumping back in. Only an inch or two at first, but I could feel his hole loosening up more and more, and I’d slide into new territory. It was thriling feeling his a****** contract around my c*** and getting to know it. I was careful to keep adding lube. I didn’t see any way to keep him from waking up sore, but keeping him wet should minimize it, I believed.

After what seemed like hours of working my d*** into him, my bush finally began to scub against his a******. I was thrilled to be completely inside him, and his d*** was rigid and leaking precum. My nuts were aching with the need to c**, and I knew I couldn’t go crazy in his newly broken in hole. So I barely pumped and I decided he needed to c** with my d*** in him. So I began to stoke his c*** with one hand, pumping slightly with my c***, with my free hand holding one of his legs high toward his chest to keep him spread open for me.

It didn’t take long with the constant stimulation – his d*** was rigid and thickened, his balls drew up so tight to his c*** that they almost went away, and his a****** was throbbing around my c***. He was also moaning weirdly, too…and his normally dead weigh began to thrash. When he finally shot it was amazing, spraying j*** all over his belly and chest. And his a****** went nuts, contracting around my d*** and i barely maanged to pull out of him before I too began to c**, spraying my load all over his c*** and balls.

I was afraid to move for several minutes while his body shivered and contracted. Finally he settled down and eased back into his drunken coma. I stripped off my t-shirt and cleaned the our loads off him as best I could, also wiping his a****** of my f*** juice and lube. To be sure, i fetched a warm rag and also cleaned his hole a little better still, because I feared the lube would still be slick when he woke up and pulled his boxers back onto him. I rolled him over onto his belly and covered him up well, then went to bed myself.

Mission accomplished, I slipped off to dream of the next time I was going to s******* him. By the end of spring term, I’m going to be happily f****** him nightly like a b**** until summer. He’d be going home with a well-fucked p****.

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I lost my virginity to my mother, but it was not like it was loving or e***** or passionate. It was not a loving thing. I was a late bloomer and knew nothing about my own body or s e x. It was just her and me. I was 14 and had recently experienced my first w********. I was confused by all that but afraid to ask her. She found it on the sheets and waa disgusted and derogatory about it. She accused me of whatever m a s tur bation was (i did not know) and got otk bare bottol spanked. I was made to wear diapers to bed so that i did not mess the sheets. This was in cloth diaper days, so guess what, as soft as they were i accidentally discovered how it felt to sleep on my stomach and grind my hips against the mattress. An important point is that my g e n i t a ls had not really developed as far as growing larger, so a cloth diaper easily contained me when aroused. She just kept getting angry and spanking me. Ended up forced to sleep in her bed because she was tired of washing diapers and did not trust me not to abuse ot degrade myself. So over time i began to attach to the brief glimpses of her dressing or u*********. What little i saw was fascinating. I could not risk grinding to get off sleeping in her bed. And the spankings were rough. Rarely bruised but extended and very painful, i usually ended up in tears. One day i was walking down the hall to the bathroom and passed her (“our”) bedroom door, it was half closed. I saw her standing in front of a full length mirror, only in panyhose, her back was to me at an angle but i saw her reflected in the mirror. Bare breasted modest breasts, very large prominent n******, broad hips, classically shaped bottom. I stood there frozen and gawking as her hand was fondling her breasts and one of her hands slid down into her pantyhose and was moving. I felt something i could not describe and instinct had me opening my pants and touching myself. Not stroking just fondling myself. No surprise she notices me and gets angry, storms over to me, snatches me into her room, angtily calling me dirty filthy etc. Tells me it was not fair that she had to go without because of being a single mother and she wasnt going to go without any more because of me. Said i was hopeless and an abomination and she was sick and tired of having to watch over me when i would nevrr change. Told me to stand there and watch like a dirty sicko if i wanted to watch so bad and could not control myself. So i stood there afraid to touch myself with her right there in front of me and i watched confused as my mother resumed pleasing her body as if i were not there. I went back and forth between directly watching her and watching her reflection. She only noticed me again when she had caught her breath and saw i was fondling myself still, and she mocked me and called me pathetic for being whatever a dirty little j******* was and not being able to even do that right. She screamed at me to get out and i ran crying. She only ever mentioned it by telling me i was going back to my bed and still sleeping in diapers. I ground myself to climax over and over night after night and she ended up making me do all my laundry. Things changed after that. She fed and clothed me but i only existed after that. She pretended i did not exist and began no longer caring about closing doors or what she wore or did not wear. Told me i was going to be dirty and look so why should she not get to act as she wished and hidjng herself as a woman from my disgusting peeping. Over time it was not uncommon for me to walk by her open bedroom door and see her openly mas tur bating in many ways. Yes i always watched. Yes i always fondled myself. But i had not actually mas tur bated to o r g a sm yet. That came one day when i stood watching an extended period of her self pleasure as i was still fondling myself watching from her bedroom door. She got angry and called me pathetic that i couldnt even be good at abusing my body like a creep. She got a bath towel and laid it on the floor and made me stand on it and instructed me to take my p e n i s between my thumb and finger and directed me how to pleasure myself with my own hand. It was earth shattering as i had that o r g a sm and barely kept my feet. All she said was to make sure the towel was in the laundry. After that it was unspoken. If i saw her mastur bating, i got a towel to stand on when i watched. She would sometimee be naked or nearly so in the house and i would get a towel and do my thing and she paid veru little attention to me. It evolved to me even standing right by her bed and even kneeling on her bed watching closer. One day i forgot to get a towel and was kneeling beside her and came so fast it was on the sheets and across her stomach. She was very angry and i had to get a towel and clean her then change and wash her sheets too. We went through a period where i was pleasuring myself so much that i would watch but did not finish myself and would go to my room to finish. One day she found me touching myself and seemed genuinely worried that i was isolating myself and was degraded with the threat that i was never going to be a man. That hurt and angered me. There came a day when i was atypically bold and knelt between her legs watching very close and curiousity got the best of me. I reached out and touched the dark hair between her legs. She froze looking at me but did not say a word and i began to touch snd investigate more. She continues to fondle her breasts and even reached down and spread herself wide open. See that she asked me? That is what a real man wants not always jerking himself like a little boy. She even instructed me as i touched her. I assisted in her climax for the first time. After she even said it was a shame i did not have a real man’s body. She even tolerated me touching myself and squirtng on her belly and between her legs. This time she was gentle verbally. Asked me to get a towel and clean her up. The next time i did not act fearful. I got just as close and touched like i wanted. My world changed when she reached for me and pulled me onto her and had me rub against her. But she also mocked.me for how fast it happened and for not even being big enough or last long enough to get it inside. I was so hurt and angry. That night she woke when i climbed on her bed while she slept. I still remember how i hated her words. Look at you trying to be a man and take what you want. Just do what you are going to do with that dirty little thing and let me sleep. Not a word as i lay on her fumblimg for entry until she reached down and guided me into her. I was only just big eniugh to enter and get past the ring of muscle. It was unreal amd draining as i quickly climaxed inside her wet heat. Wben she told me to leave and go back to bed i knew i would be back. I was never allowed to stay the night in her bed but most nights i would walk in and she would just open her legs and tell me to do what i needed to do. I cannot imagine how many times this happened day after day. Silent resentful s** with grudging consent. All during high school. Frequently on the way to and from work when i got a job and moved out. Holidays. I would go over and she would be in the kitchen cooking and not even miss a beat. She would be wearing a dress and i would enter and stand behind her g**** her breasts and grind my hips against her and she would put her elbows on the counter, and i would grind against her spurting between her cheeks or thighs since even as an adult i am too small to enter from behind at all. Always told just do what you are going to do. All of it silent even as i cleaned her of my pathetic sin with a towel. Evem now when i pleasure myself i still see her looking at me with contempt, hear her telling me to just do what i need to do with that dirty little thing. I got therapy and finally broke free of my s***** addiction to her. But she is still the only one that i have had s** with and i am in my 40s now. I pay an e***** to hold me and be momny as i touch myself and she calls me her pathetic dirty little sicko and j*******.