The first time I [f]ucked [m]y roommate's girlfriend (long) | 2016

Summary: I fucked my roommate's long time girlfriend almost every day (excluding weekends) for about 8 months of the year we all lived together.

A little backstory, and this is a true story. We'll call myself Luke in this recollection.

I lived with my friend, let's call him Matt, for about a year after we both graduated college. We lived across from each other in the same (co-ed, which lead to some other stories I'll post later if this is well received) dorm for the first two years of college and became pretty good friends. We hung out all the time, ate meals at the dining hall, played ultimate frisbee, video games, drank, and all of that fun stuff college guys do. lu After those first two years, I moved into an apartment with some other friends (which brings to memory some other good stories I'll post later). We lost touch a little bit. I still hung out with him here and there, went downtown to drink with him and his girlfriend, but we weren't nearly as close as we were in the dorms.

He had started dating this girl, we'll call her Mary, the summer before college. The first time I saw her was when I was moving into the dorms with my dad. She was the first REAL beautiful college girl I'd ever seen. Even my dad remarked, "wow, did you see her? I think you'll have fun here".

Mary was indeed beautiful. Your typical blonde, girl-next-door-ish southern belle (we went to an SEC school), but a step up from the rest. When I first saw her, she was wearing a red top with a cami underneath and jeans. The cami and what I suspect was a nice push up braw worked well to push her on the larger end for her frame but seemingly perky breasts together showing a nice bit of cleavage. The rest of her body was framed perfectly by her tight, well fitting jeans. I'm a total ass man, and her ass was (and still is) wonderful. It was the round, tight lifted ass of an athletic girl who took care of her body (later learned she played soccer and several other sports, but not too hardcore so be jacked or anything, just well toned and gorgeous). She had curly blonde hair (sometimes she wore it straight), blue eyes, well proportioned lips for her face, a well defined feminine jaw line and gorgeous collar bones. She was about 5'6", again, slim and athletic, probably no more than 120lbs. I'd probably give her an 8.5 or 9 out of 10. Not quite SI Swimsuit or Victorias secret model but pretty damn close. I'm sure if anybody would have looked at the time they could've seen me drooling.

Anyway, I continued moving into my dorm and looked across the hall to see her with my neighbor. I thought "damn, she's taken. Oh well, there will be more". About that time, Matt walked over and introduced himself, and his girlfriend Mary.

Jumping around here and there in the six years or so since I hung out a lot with both of them. She was that friend's girlfriend you always wanted to fuck but knew you never would, so you pursued other things.

That didn't keep me from sneaking peeks up her skirt when I got the chance, or checking her out when she wore skimpy clothes around us. I also took note when when we'd causally talk about sex and masturbation. She loved both and would talk about it freely. It made Matt a little uncomfortable but whatever. I'd also comment on noises I heard from her room when I saw her, and she and Matt would give me a high five. They would also return the favor when I brought a girl home.

Here and there I would swear she caught me looking and showed a little more. One time, I was in the hall in my boxers walking back from the bathroom late at night, as per usual. She walked out of Matt's room looking frazzled and flushed in a towel, like they just had sex. She smelled like sex, too, and I caught her checking me out as I looked at her in that towel, dreaming (I LOVE girls in towels). I said to her "you look like you had fun", and went to give her a high five. I've always wondered if this was on purpose or not, but without thinking she reached up to five me back and her towel dropped. She froze there for a split second and I got a nice look at her body. It was almost perfect. Her tits were perky, she was shaved and had "dat gap" and an amazing looking pussy. I got hard instantly. She had to notice, because after she quickly grabbed her towel, blushing I stopped her to apologize profusely. She said "It's ok it's ok. Just forget what you saw and we'll pretend that didn't happen", smiling reassuringly.

I immediately went back to my room and fapped.

Anyway, fast forward five years later.

Matt is working for a big time bank in the big city a couple hours from our college. He knew I was looking to move down there to find work, and having just bought his own condo he asked if I wanted to live with him for a while for cheap rent. He wanted a roommate. I accepted.

It was a really sweet deal. The condo was super nice with great amenities. It also was home to a lot of young business men and women, meaning lots of hot girls around to hit on if I worked up the courage. Plus, Matt worked from 7am-10pm most nights at his crazy bank job. We didn't see each other much but would hang out when he was free or when he'd come home late. I really couldn't have done any better situationally.

Mary was pretty much always around. I mean, she 95% lived there. At that point they had been dating for six years. Schedule wise, she worked in the mornings and would usually come back at about 330-4pm, but she was almost always there when she got off work, hanging out and doing whatever until Matt came home.

She was still as hot as ever, but I aside from casually checking her out I didn't think anything of it and we just hung out like normal when we were both home alone together. She was always a little bit flirty with me, though, and sometimes I'd catch her walking around in the condo in her underwear or a towel, or just a t shirt in panties here and there, but it was rare. She would also, rarely, see me the same way here and there. I caught a second glimpse of her naked one night when I was in the kitchen at about 3am making a snack. She had apparently gotten up in the middle of the night to grab a glass of water and just went naked assuming I was asleep. "Fuck! I thought you were asleep!" she said. She covered herself with her hands and quickly slipped back into the hall, but not after I'd gotten a nice look in before she noticed me.

Usually I'd wake up between 1130 or 1pm, lounge around in my boxers on the internet, fap, work out, shower, eat a late lunch and then hang out until Mary got home. Then we'd either watch TV and talk about her job, or we'd both just do our own thing. That was the schedule or routine for about three months, until the day she came home early.

Because I was so confident in them not being home, I would browse GW, watch porn videos and fap in my room with the door open (it somehow made it hotter for me). It was kind of stupid, because they could come home for whatever reason, but I thought I would hear them come in and be able to hide it before they saw me.

One day, though, I didn't hear Mary come in. I'll assume she heard the porn I was watching and then came to my room to check if that's really what I was doing. My back was, stupidly, to the door, and I wasn't aware of her being home until she leaned over me and said "I always wondered what porn you were into. Nice cock by the way", laughing at catching me.

I was shocked and scrambled to cover myself and close the porn. I was bright red and trying to come up with some kind of explanation, but all I could say was "well, you caught me... I'm so sorry, don't tell Matt!"

"Don't worry about it," she said, "just thought I'd scare the shit out of you. I always knew guys masturbated like crazy when they were home alone. Girls do too, you know, I do it on the couch after you leave for work, usually."

She laughed about it once again as she sauntered out of the room. "Close the door next time!" she said, smiling at me while I sat there, dumbfounded with my boxers covering my junk. As she closed the door she said "plus, you've seen me naked twice now, I figured it was my turn."

After that, she got a little more flirty with me, and playful. She'd always joke about me having a good time fapping that day when Matt wasn't home, stuff like that. Then I think she decided she wanted to torture me a little. One day she came home later than usual. I remarked on it and she said she'd gone shopping. "Want to see what I bought? I got a new outfit," she said.

"Sure," I said, not thinking anything of it. She went into her room for a few minutes and came back out wearing the sexiest set of black and white lingerie with black garters. My jaw dropped as she posed there for a second. I immediately got hard. She noticed and said "I'm glad you like it, I think Matt will love it, but it's good to know I look good!" She laughed and went back in her room to change. I fapped my brains out. The next day I snuck into their room and fished the underwear out of the bathroom. Size small panties, and a 32D bra. Nice. I am ashamed to admit that I rubbed my cock on the panties and left a little precum.

Later in the week she started wearing less and less around the house when it was just her and I. It slowly devolved to her just wearing a t shirt or tank top and panties around the apartment. It. Drove. Me. Nuts. I tried to act like everything was normal when it was just us, and I didn't want to complain to Matt. It would cause problems between them, for one, and for two, I was REALLY enjoying the views I got.

She would tease me with glimpses of her ass, picking things up, leaning over me so I could catch a peek at her tits. She would be more touchy, sit closer to me, etc. She was really driving me crazy and acting like nothing was abnormal. She was just chilling, but I knew it was all on purpose.

I started to spend more time in my room, but of course I would fap to what I just saw a lot of the time. I wanted to avoid her, though, because I didn't want to betray Matt. I can't emphasize how much she was driving me crazy. I was thinking about moving out just to get out of the situation, but then things came to a head in a wonderful (yet awful) way.

I was hanging in my room like usual in the afternoons, but it was about 530 and I was getting really hungry for dinner. I decided I'd brave seeing Mary's hot fucking body torturing me to get some food. I walked outside and there she was, buck naked on the couch masturbating to some porn on her laptop like there was no tomorrow.

She saw me, smiled. I knew something was up. "Hey Luke," she said. She wasn't doing anything to cover herself up. She just laid there, looking at me. I froze, and my cock was filling with blood a mile a minute. After about five seconds, but what felt like an eternity, she got up and walked over to me, pushing me up against the kitchen counter.

"So I was thinking," she said, "I know you like to masturbate. I LOVE to masturbate. Every day. Sometimes I even think about you and that nice cock of yours."

I gulped.

"Since we both like to masturbate so much, I figured we'd do it with each other. We can just use each other as toys. I know you're hard. How about right now, what do you think?"

I gulped again as she started reaching for my cock, my resolve waning, "What about Matt?"

"Oh, don't worry. He won't be home and I don't consider this cheating," she said to me smiling as she pulled down my pants, "He doesn't care if I watch porn and play with toys, so I'll watch porn and play with a toy... you. Plus, we only have sex these days on weekends. If I don't cum every day I'd go insane!"

I didn't say anything. I just let out a soft moan as she lowered herself on her knees and licked the pre-cum off of my tip. "You taste good. We're both super horny. I'm dying during the day. How about we play with each other?" She said.

"Okay," I said, already smitten, powerless against her. She started sucking my cock slowly, stroking it with her hand and taking breaks to like it and look up to me. I can't say it was the best blowjob I've ever had, but with the situation, how turned on I was, and the skill she had it was pretty damn up there.

She sucked me off for about five minutes, well that's what it felt like but who knows, until I said "Shit Mary," I moaned as she took me back in her mouth, swirling her tongue around my cock, "if you don't stop I'm going to cum!"

"Ok then, time for you to eat me out!" She said enthusiastically as she hopped up on the kitchen's island counter. I started rubbing her pussy with my thumb first. It was soaked, dripping on her thighs and thick enough to have that slight whiteness to it. I rubbed her clit as she put her head back and moaned. "Use your mouth!" she commanded. I bent down and started eating her out on the counter. I myself was throbbing. I'm not big into how pussies taste, but hers taste how I like them to taste. Slightly sweet, salty and a little pungent. Not pungent in a bad way, other than that I can't really taste anything in pussies usually. She had a VERY pretty pussy. Her labia majora weren't huge, just big enough, the minora was tall enough so that it was barely visible, just a line between her majora, and she had a nice small clit. Altogether her pussy was tiny, clean, meaty in just the right ways and super super awesome.

I was in heaven and couldn't believe what was happening. I had just gotten my cock sucked by a girl I've thought about fucking for years, but never realistically. The thought of fucking my friend's girlfriend really turned me on, too. I'd always wanted to fuck my friend's girlfriends. I mean, I loved fucking mine too. But something about it was just hot. Now I was eating her out. Heaven.

I ferociously licked her clit while I looked up at her body from between her legs. The BEST part of eating a girl out is when you make her back arch and her perky nipples stick up in the air. It's my favorite view. I'd had a bit of practice eating girls out, so I'd say I'm pretty decent at it, and Mary was going crazy. "I want you to make me cum!" as she moaned with short breath. She had a nice soft high pitched moan. I loved it. Since she asked for more I slipped my middle finger into her. She mouned a little louder and squirmed. Her pussy was so tight I could feel it around my middle finger, squeezing me, grabbing me. It made me want to fuck her so badly, to feel her squeezing my cock with her pussy, but I had to make her cum orally first, so I kept working harder. Slowly finger fucking her with the "come hither" motion while I licked her clit.

After another minute or so she said "fuck I'm going to cum!!" I felt her pussy grip my finger tightly as her legs squeezed together, kicking my head out as she bucked her pelvis. Her legs were shaking, but I kept my finger in her, making her body buck uncontrollably. I didn't even ask before I stood up, pulled her legs apart and plunged my cock into her. It was so wet it just slid right in. Normally I ask girls before I do this when having sex, just to be courteous (I had a girl tell me to stop once after making her cum with my mouth, she wasn't ready to be penetrated yet, so I was always cautious), but I could tell she wanted it bad.

I fucked her slowly but deeply. Feeling all of her pussy grip my cock as I slid in and out of her. "God you have a nice cock," she moaned as I started fucking her a little harder and faster. For reference, my cock is reasonably sized for a guy who's my height (6'6"). A solid six inches long, but nice and girthy. I have a bigger build, like an NFL player, broad shoulders and the like, so the girth is proportional. I think that's why girls love it in my experience. Not too long, but nice and thick. It reaches all the right places. The way I was fucking her now her tits were slightly bouncing as she lay on her back. She was looking up at me, smiling and moaning as I looked over her beautifully toned body in semi-disbelief. I'd fucked girls this hot before, sure, but they weren't her. I'd wanted to fuck her for so long now, so it was different.

I started to fuck her harder and harder, moving her legs around to different positions and my favorite, holding them together and watching my cock slide in and out of her little pussy. She moaned and was loving it. I wanted to cum all over her right there on the counter, but then she leaned up and said "lets go to your room. I want you to fuck me from behind."

I pulled out of her as she popped up off the counter and skipped into my room. Literally skipped. She was enjoying herself! I walked in my room to see her on her knees on the edge of my bed, ass up in the air. It was better than I had ever imagined. Super hot. I wanted it, I had to have it, so I walked up to her and started licking her pussy again for a minute. She moaned, then I stood up and slowly slid into her. She had gotten SUPER tight from this position. It was almost unbearable.

"I want you to fuck me hard like this, it'll make me come again!" She said. I went to pound town just railing her pussy like that. It was making a loud slapping sound because she was so wet. Her juices were everywhere. "Holy shit holy shit, I'm gonna cum again," she said as I pounded her like an animal. Squeezing her ass tightly and watching her tits bounce in the mirror on my dresser. After she came I pushed her down on the bed on her stomach and climbed over her. I loved that view with her on her stomach with her legs together, her little gap showing and her throbbing, pink, wet pussy between her legs. I admired it for a second, and then plunged into her. This was my all time favorite position. I loved that view, and I was going to fuck her until I came like this.

I fucked her hard like that, watching my cock slide in and out of her sweet little pussy, admiring and squeezing that tight little ass. "Fuck you're amazing, I'm going to cum soon," I said.

"Good!", she said "I want you to cum in my mouth!"

I couldn't believe it. The thought of that drove me over the edge and I felt my nuts well up. "Fuck I'm gonna cum!" I said as I slipped out her. In one motion I slid up to her face as she flipped over under me. My cock plunged into her mouth and she sucked me absolutely dry for about 30 seconds. I thought I was going to explode. My cock was on fire. I'd never had a girl suck me dry like that. It was the most intense orgasm I'd ever had. I stayed on top of her marveling at the sight of her face looking up at me with my cock in her mouth. I reached back to play with her pussy but she stopped me. "God no it's so sensitive," she said.

I got off of her and rolled on my back. "Damn, that was unexpected," I said.

"Yeah that was fun! We should masturbate together again tomorrow! I'm going to go take a shower now," she said as she hopped up and walked out of my room. Legs a little shaky. She smiled and I smiled back, watching her perfect ass walk away from me. She turned around and said, "oh, and this mutual masturbation thing better stay our secret. You're my favorite new toy, so don't tell Matt."

I couldn't believe what just happened. I laid there, sweating and in shock. My cock covered in her juices and going flaccid. I just laid there for about ten minutes. Later, I looked at the time and realized I needed to start getting ready for work. I got up, went to my shower and started to get washed up as I thought about what had just happened. I got hard again. Damn I wonder if she meant what she said about tomorrow, I thought. I also thought about Matt for a moment. He would never know, for sure, unless she told him. I was sure as hell not going to tell him.

She did mean what she said about the next day. And the day after that. Basically, five days a week we had sex every afternoon. Some days we'd watch porn together naked and then fuck. We'd do what they did on the porn, mimicking the scenes. Some days she would walk in the door, lock it, take her clothes off and start sucking me off. I never had to initiate it, she always did. We stopped wearing clothes around the house together after a while, and would just fuck like animals. Sometimes multiple times. The BEST were the days she had says off. I'll write about those later if you want. They always started off very nicely.

We fucked every day for almost four months. Then the novelty kind of wore off and we'd fuck probably two to three times a week. Sometimes things would ramp back up, and sometimes I wouldn't feel like fucking her and would say no. I guess kind of like when you're in a relationship and well, the novelty of sex all the time wears off. We still went at it pretty hot and heavy the whole 8 months after we started that I lived there. I felt a little bad for Matt, but somehow it just seemed to make their relationship was better. She was happy, and so in love with him when they were together. She loved him when they weren't, obviously, but I thought "wow, maybe she does think of me as just a sex toy in that aspect". That was fine with me, because I wasn't romantically interested in her. I just wanted to fuck her, and that's what I got. She always referred to it as masturbating, too.

I was pretty sad after I moved out. I missed my almost daily romps with her. They were so much fun. For a while after I moved out I would still come over and fuck her when she texted me. We stayed fuck buddies for a while. I broke it off when I started dating my current girlfriend seriously. The day we had talked about the relationship being exclusive. Mary understood even though she didn't think what we were doing was cheating, but she told me that whenever I wanted to masturbate with her again to let her know, and that she had really enjoyed playing with me. Sometimes here and there she'll even text me and try to sext with me a little bit to try to get me to play again. It's really tough not to say yes when she sends me pictures.

So that's about what I got on this one, unless you all want stories of her days off and such, which were pretty ridiculous. She's pretty crazy, but I hope her relationship with Matt still works out. We're all still friends, too.

If you have any questions feel free to ask. I'll answer as best I can. Thanks for reading! Also, sorry for any grammar mistakes. I didn't feel like proofreading and I haven't written something this long in forever.