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****.