Roommate Obsession

This is a fantasy story with some elements of truth, a story of my fantasies about somebody I knew.


In my undergraduate years a group of friends who I got to know freshmen year all decided to split an apartment near school. Well, it was more of a house than an apartment. I lived with 3 other guys and 4 girls. At the time I was an overambitious young man who ended up with fantasies and desires for all four of my female roommates. One of them I fantasized about more than any other, and her name was Carrie.

I can't really tell why I focused so much on her for my fantasies. She was average looking, blonde with blue eyes. I think she was of part Scottish and Polish descent, pale as can be. She had a "sturdy" build. I don't mean that she was fat. She was short but somewhat muscular. Got a little bit of a roll if she was leaning but her proportions were completely normal. Most days she wore jeans or khakis, never tight fitting leggings or tanktops. A lot of the fat that she did have ended up in her chest, but that's not the part I liked. Even more of it ended up where she sits; her ass was tight fitting, round and wide.

Maybe part of the reason I fantasized about her so much was because she was so obviously out of my reach. We were good friends, but it was blatantly obvious that an actual relationship between us was absolutely impossible. Personal views, political views, personality clashes. We liked each other as friends but nothing beyond that.


Very quickly into the summer before classes started I learned how easy it was to be a creep when you're living with other girls, but still get away with it. The first one to move in after me was another of the female roommates. It didn't take long to realize that there were ways to peek into the bathroom while someone is using the shower, or that the locks on the doors didn't work very well. Maybe I'll write about those experiences some other time, because that goes to some interesting places as well. Before that though, Carrie moved in about a week before classes began.

The weather was humid and hot all week. All month really, and we didn't have air conditioning. It sucked. Carrie would wear loose gym shorts [she was too "conservative" for tight fitting attire] and her legs were extremely hard to ignore. She was a morning bather, and on one particular morning I felt and irresistible urge to act on some of my fantasies before I jerked off and the urge went away. The best way to get a view into the shower was to angle a CD or DVD at the base of the bathroom door. This obviously wasn't very good, but as she was facing the shower away from the door I got to get a good look at her bare ass. It was like a sculpted masterpiece. It was pale because... well... she never tanned there. Her buttcrack was short compared to how wide her cheeks were, which explained why she could always bend over and not show any plumber's crack. I only got to see this for a few moments before she stepped into the shower and I heard another roommate enter the hallway.

This satisfied my fantasies for her well into the semester, until I noticed she was becoming increasingly exhausted from the work load, she was drinking more and was sleeping in later into the day on weekends, even missing church. Mind you, she never got piss drunk or passed out [again, too "conservative"], but my mind started to wander.

I used to have a near insatiable somnophilia fetish ever since I was in middle school and my older sister had sleepovers. It was extremely rare that I had the courage to act on this though [a story for another time]. Well, I was thinking this may be another one of those times. One morning I set my alarm for 8:00am on a Sunday. I packed a pair of scissors and a camera into my pockets and as quietly as I could, I sneaked over to her room and shimmied her door open. The nice thing about doing this at Seven was that I could just use natural sunlight to see.

Carrie was sleeping on her stomach with the blankets off of her. Too hot to bother with fucking blankets. She was wearing a white teeshirt and bright blue nylon shorts. To test if she was awake, I hissed her name. Then I crept closer to her and poked her shoulder, and then gently rocked her. If she was awake I could try using the excuse of "hey, don't you have to get up for church?". It was far from the perfect excuse, since I normally sleep in on Sundays, she was Escort one of the only ones who could be described as "religious" at all, and even if I were honest that doesn't justify my creeping into her room. Still, not as bad as my true intentions.

When I confirmed that she was really asleep, I glided my palm over her buttocks and smoothly caressed them. By now my hands were soaking with sweat, my heart felt like it was pounding like a machine gun, and I had to take a shit. I didn't think I could actually get her shorts off without waking her up, so I pinched the fabric over her asscrack and, with the scissors, snipped off a tiny piece. The cut wasn't anywhere near big enough to actually see in to, and she was wearing underwear.

Well, that's kind of boring. I had a decision to make, cut more and get through the underwear, but also hugely increase the risk that she would notice later? Aw fuck it, I wasn't thinking straight. I ended up cutting a good inch of her shorts, and I could clearly see her bright neon green underwear in the hole. Now I was going nuts. I poked her asscrack through her underwear and wriggled my finger around a bit. Then I cut a nice hole in her panties about the same size, so I could see her bare crack.

It was only a tiny amount of crack, but up close it was so much more amazing. My hands were shaking like I had just snorted coke. With my right thumb and index finger, I spread her crack open. My aim with the scissors was just a little high, but I could still easily see the wrinkled puckered skin of her anus and a few pale, wispy hairs. Her asshole wasn't really brown like I expected, more like just a slightly off shade of her normal skin. My heart had basically stopped at this point. My left hand clumsily fumbled for the camera, and I ended up dropping it at least twice. I took at least 5 pictures and then a video of my spreading her crack open and close for a good minute. Satisfied, I gently stroked her asshole with one of my fingers.

I heard her moan and begin to roll over. I absolutely panicked, grabbed my camera and ducked under her bed. She unconsciously re-positioned herself and apparently never woke up, but I ended up huddled under her bed for too long to be sure. I began worry when I realized that my other roommates might wake up soon and there was no subtle way to get out of her room without being noticed once they were out and about. I crawled out from under her bed, crept out of her room, closed the door, back into my room, and jerked off furiously.

I'm sure Carrie noticed the hole in her shorts and her panties, as she never wore them again. Then again, she never said anything about it either. I don't know if she ever suspected me, one of the other roommates, or if she just thought the fabric ripped somehow. As is natural with all college apartment situations though, some elements of friction began to emerge as time went on. Just little stupid things like the toilet seat being up, dishes not being done, etc. Nobody ever broke out into a fight, and everybody was still friends by every measure, but the "honeymoon" had definitely ended.

One of my male roommates ended up making friends with some... shady people. I'm not one to talk as I violated a sleeping girl's butthole, but to Carrie and a few other people it was more than a little annoying when he brought these friends back to hang out. At least a few of them were pretty clearly into drugs, though I doubted it was anything beyond just weed and that didn't bother me at all. One night when we were all hanging out Carrie walked past me and one of these friends apparently noticed me staring at her backside as she wandered off. When I got up to take a piss, he cornered me in the bathroom and made... a proposal to me. As it turns out he was actually a dealer, and had... "a great variety of merchandise" available, including roofies, ketamine, and ambien. He made me two offers, buy something from him for... what seemed like a shitzillion dollars to me. Or, take pictures and videos of me violating each of my female roommates.

To my perverted mind the latter option sounded unbelievably arousing... but what tiny splinter of my rational mind fought against it. Videos of me violating a roommate could easily end up being used as blackmail against me when I intentionally hand it over to someone else. I made a counter-proposal, just buy a more "affordable" 1-time Escort Bayan dose as a sample, and if it worked well we'd talk again and negotiate something. Well... my negotiating skills aren't great and he ended up with more of my money than I would have liked, but I made the deal.

It would be another week before I got my hands on my purchase. During that week I was carefully planning out scenarios and a wishlist of things I'd want to do. When I got my hands on the stuff though... those plans were mostly abandoned and I ended up trying to jump on the soonest opportunity to act. Whenever I'd try though, I'd immediately get cold feet and back off. No time seemed right, and I was being held back of sudden moments of morality when I realized that this was fucked up. Well, that changed a few days later when one evening she chewed my ass out over something about the coffee machine not being clean.

That got me pissed. Not in any rational way, it was just a stupid non-issue, but it still made me pissed. Emotions everywhere were starting to get frayed as exams grew closer and the weather got progressively shittier. When it got late at night and my other roommates were mostly asleep or getting ready for bed, I knocked and entered her room. We had a brief, cordial conversation about nothing, it was pretty clear that neither one of us wanted to talk about the argument earlier. Eventually she turned away and continued her homework or studying or whatever. On her desk was a cup of hot cocoa. As subtle as I could, I slipped the venomous concoction into her drink and mixed it under the guise of my picked up her mug and smelling it.

I waited until one in the morning to see if anything had happened. Mind you that I also had classes early in the morning and I was really setting myself up for an extremely shitty day in classes, but I could hardly have cared less at the time. Once again, I wandered to her room, this time with the camera and some lotion. I didn't need scissors. She didn't even attempt to use the useless lock this time, she might have passed out before even trying.

I closed the door behind me. She wasn't laying on the bed, instead she was still fully clothed, slumped over her desk. She was wearing jeans and a dark green long sleeved sweater. The drugs had obviously worked. I crawled over to her, hissed her name, poked her, shook her, the works. Nothing. She was completely out. Practically in a trance, I turned the bedroom lights on, hoisted her up and face up onto her bed. I couldn't decide what to do first. I gently slapped her face to confirm that she was fully out. Then, out of nowhere, I ended up slapping her across the face extremely hard. I don't know what came over me, maybe some residual anger from before. The slap turned her head sidewise and I heard a low, painful moan escape her lips. For a brief moment I was sorry and regretful, but that was immediately replaced by fear that the loud slap might have woken the roommates.

When it became clear that nobody was up, I forgot my sorrow and regret and pulled her sweater up. She was wearing a plain, tan bra over her respectably sized bust. I didn't have the patience to actually unclasp the bra, so I just ripped it off of her body. Her boobs jiggled downwards and outwards in a satisfying way. For a few minutes I gently caressed and pinched her nipples, then proceeding to licking and sucking them. I took a few photos of them because... why not? They were far from the main attraction though.

Her jeans were belted on tight, but getting them off was simple. This time she was wearing bright neon blue panties. I pulled those down to find a small-ish bush of dirty blond pubic hair. I didn't dwell here, it wasn't anything special to me [idk, maybe I should start questioning my sexual orientation]. I just took a few pictures and moved on.

The main attraction to me was, of course, her ass. I rolled her over onto her stomach and dragged her across the bed so her legs were dangling down the side. Seeing her ass like this was even more magical when it wasn't being mostly concealed by pajama shorts. I spread her wide, full asscheeks and got an eyeful of her pucker. It had been too long since I got this close to it. Without thinking I dove my face into her crack, licking her ass up and down and drilling my tongue into her shithole. I tasted like shit... as you'd expect, but my brain didn't register Bayan Escort that at all. I was absolutely euphoric. I pulled my face away and starting spanking her ass over and over again, almost as hard as I hit her face. Every time my palm smacked her ass, the fat on her cheeks and thigh would jiggle in a mesmerizing way. I stopped when I heard a low gurgle from her mouth, and her ass was turning pink.

I readied the camera in my left had and wet my right index finger with spit. Set to video record, I filmed my finger as it entered her, as her sphincter clenched around it, and how it kept relentlessly twisting and drilling until it was in as far as it could go. I finger fucked her ass for at least 2 minutes, and then I added a second finger, and then a third. The time had come for the main course, but I could feel that my cock was ready to burst practically the moment it made contact her skin. I wanted this to last longer than that. I dragged her sideways so that her head was almost off the bed and she was facing me. I dropped my pajama shorts and slid my cock into her mouth. I could feel her tongue unconsciously slithering around. It felt heavenly. I knew I couldn't last long, so I crammed my cock in all the way to the hilt and to the back of her throat. I could feel her gag, but after just a few thrusts my cock exploded and sent almost a full load down her throat.

I knew I needed some time to reset before I could go for round two, so for a little while I repositioned her back so she was again face down with her legs dangling off the bed. I satisfied myself with eating her ass and pussy out for a little while, and this time I actually did finger her pussy a little. She was still a virgin, so I didn't want to push that too much. Before long my cock was up and ready for round two.

With the camera at the ready again, I dripped some lotion onto her bunghole, and then onto my dick. As I filmed at first I gently pressed my head into her sphincter, and slowly worked my way in. Godly wouldn't even begin to describe the feeling. My cock isn't very big, but that means that I could pump it all the way in and out quickly. As time went on I picked up the pace, and soon I was pounding her as hard as my body could. All the mean while I heard painful grunts and groans escape her lips, though there was never any sign of her regaining consciousness. This lasted for at least ten minutes before my second wave of cum was unleashed into her bowels. Exhausted, I collapsed on top of her to regain my strength, I slid my cock out to find shit smeared on its head and along its length. Her anus was puffy and red, and there was a mixture of cum and lotion dribbling out.

Normally that would gross me out, but my euphoric, perverted mind decided to slide my dick across her face and into her mouth one last time, as she unconsciously got her own shit in her mouth.

At least a half hour passed by as I sat there zoned out, in a trance over what I had just accomplished... until fear and panic began crawling back and I realized that there was no way she wouldn't notice that her ass hurt in a few hours.

In one of the more clever schemes of my life, I raced into the bathroom and forced myself to shit. It was forced, not much came out, but enough. Then I ran back to her room, threw her sweater back on [unfortunately her bra was ruined], and slid her panties and jeans on halfway. I grabbed her by the shoulders and dragged her to the bathroom, where I sat her upright on the unflushed toilet with her pants down. I wiped the shit and cum off her face and out of her mouth as best I could, and then I pranced away off to my own room.

I didn't sleep at all that night. I was hoping she would just convince herself that she had, for whatever reason, passed out while taking a shit. Fear had completely overcome me, and I could just envision myself on the news and in a court room as the scumbag who anally raped his roommate, having to explain to my parents what happened, losing the respect of my friends, etc.

Well, morning came and a groggy, dazed Carrie came stumbling out of the bathroom. Both her and I looked like total shit, and felt like total shit the entire rest of the day during finals crunch time. She never complained about the feeling in her ass though, and as far as I know she never suspected what actually happened.

I completely got away with it. I got memories and video to immortalize my conquest of Carrie's keister, and there was still a negotiation to be made with that one friend of a friend who made this all possible...