When [M] living with a [F]emale roommate turns into an affair

*****Warning.. Long.. bit of backstory, skip to the asterisks for the fun stuff****

I have read a lot of the stories on here, and enjoy most of them. The roommate ones always take me back and have me thinking about, ….We’ll call her Bri. This story dates back to several years ago back when I was a junior in college.

I was a shy guy in college, and pretty terrible at hitting on women. I grew up with brothers, so conversations with lady folks wasn’t exactly my forte. Usually the only female friends I had were girlfriends or acquaintances of my guy friends. These were also the only women I was able to completely be myself around, and that was an entirely different person from the guy that was first meeting a woman. It’s not that I’m unattractive. I was just a late bloomer, and getting over the insecurities that come with that, take a bit. Over time, I’d finally get comfortable and start coming out my shell, and I often found these girls becoming attracted to me. Me being a horny 19-20 year old shit head, I sometimes took advantage of those situations. What can I say… It was hard not to be a terrible person back then, and I often found myself reciprocating the attraction. One such girl was the aforementioned Bri. Bri and I met through a buddy of mine freshman year of college. My buddy was much better at first impressions, and had made close friends with some stoner girls on his dorm room floor. 3 cuties. I being the shy kid probably said all of about 3 words to them the first several times meeting them. We’d get high together and I’d sit on the couch giggling. Those initial days turned into months as I slowly came out of my shell. Those months turned to years, and I still keep in relatively close contact with all of them 20 years later.

Bri always had a boyfriend. Unfortunate, but I wouldn’t have been able to make a move anyway, so it didn’t really matter initially. Bri was sexy. Super sexy. And she carried herself with the confidence of a sexy woman. She had almost platinum blonde hair with a cute little bob cut. She had a super tight body with the most incredible ass. God I loved that ass. I’m an ass man, so of course that’s what I became infatuated with. She loved to wear tight pants, and I loved to stare at it. She was also incredibly smart and flat out super cool. And the sexy smile… She could make me blush just by smiling at me. No chance, so it didn’t matter… or so I thought. There was the time we were downtown after some bar hopping when I was being a little more outgoing (and I could be pretty adorable), when she dropped the line that spun me a bit. “God, ftfw2010, you’re so cute and funny! Where were you when I was single?”….. pbbbfffftttt. Didn’t matter.. She had a boyfriend.

Bri didn’t hang out with the group of friends as much as some of the other girls because she mostly spent that time with her boyfriend. Then came the separation. Maybe I finally had a shot? By then, I’d kind of started an FWB relationship with one of the other girls from the initial group, and so timing wasn’t great. Bri was single for about a week (it seemed) before she started dating my buddy Tim. Fuck. Oh well, wasn’t meant to be. But that also meant she was around quite a bit more, and we developed a solid friendship. A couple months later, my buddies and I were looking for a house to live in, and she needed to place to live as well. Next thing I know, she’s my roommate…

This was a gift and a curse. That body looked a lot better in minimal clothes, and she started to get pretty comfortable around the boys. Then the grab ass started… It really stemmed from an acid trip where my buddy George, her, and I all laid out in the middle of a park, laughing hysterically with bodies intertwined. Acid loosens the inhibitions, and I told her how much I admired her perfect ass. She told me I could give it a solid squeeze, and I melted. I’m not sure how exactly it happened, but I think there was some sort of bet where the final outcome was that she agreed I could grab her ass whenever I wanted to… Fuzzy memory, so not exactly sure. At any rate, Bri started spending quite a bit more time at home, and a lot less time with her boyfriend/my buddy. And she started getting comfortable walking around in just her underwear. Then came that first night.

******* George, Bri and I shared a night at home where we all got pretty drunk. Bri was still dating Tim at the time, but her and I started getting really close. We spent a good portion of the night in her room laughing and telling stories, before George finally called it a night a went to bed. She had spent most of the night wearing only a pair of black cotton panties, and a tank top. After George left, I told she looked fantastic in her little getup, and I was into it. That’s when the look in her eye changed, and the sexiness took over. God damn. We jumped in her bed and started petting each other pretty heavily, then she laid me on my back and straddled me. I’m hard as a rock, and the next thing I know my dick is out, and I’m rubbing against the thin layer of panties covering that beautiful ass. She goes in for the kiss, and we make out for a bit. I think I had just watched “Leaving Las Vegas” where one of the rules was “no kissing” so as not to catch feelings. Being that she was dating my friend, I moronically thought the “no kissing” rule should apply here. I said it, she seems a little taken aback, but ultimately was cool with it. There was more grinding of my dick on her ass, and heavy breathing and neck kisses…. Then all of the sudden her panties came down just enough, and my cock slipped into the most amazingly blissful pussy I’ve felt to this day. The sexiest moan and exhale came out of her mouth, and instantly I felt like I was going to explode. I had a quick semi-freak out, Pushed her up just enough to pull my cock out of her before exploding into my hand…. Now… it was dark, and I was embarrassed as fuck, so I tried to play it off like we shouldn’t be doing this.. To this day, she has no idea that it was actually because I had just blown my load into my hand. I casually wiped my cum on the sheets between the headboard and the mattress to get rid of the evidence, and went back to snuggling close to her, still trying to play it off like I was incredibly horny (which I was) and just didn’t think we should go any further than some rubbing and groping. The groping only policy didn’t last long, and soon I was at full attention again. This is when I decided “fuck it” and the no kissing thing went out the window. Now we’re all over each other and it’s glorious. Years of pent up sexual energy went into the make-out session, and now I’m on top of her.. and now my cock is rock hard again.. and now I’m rubbing it against the entrance of her pussy… She grabs me hips, pulls me into her, and pushes up into me… Ecstasy… Emotional and physical bliss…. Then the emotional aspect took a back seat to the carnal instinct of two sexually charged 20 year olds. I began pumping into her with unabated inexperienced enthusiasm. We sucked on each others faces and clawed at each others skin. Within minutes I can feel her begin to spasm beneath me. She moans and whispers into my ear that she’s cumming. Suddenly her wetness multiplies and I slow down to gentle strokes as she recovers.

“Switch it up?”… “Fuck yeah!”

I pull out and roll off of her on to the bed, and she climbs on top and starts to straddle me again before pausing. She gives me a little giggle then moves her mouth down to my cock and starts sucking. For any ladies out there reading, this is one of the hottest things on the planet. After about 20-30 seconds of some intense suction, she crawls back up and kisses me, as she slides my cock back into her pussy… Now I’ve had my fair of experiences with women, but none have come even remotely close to matching Bri’s enthusiasm. The audible lust coming from her as slid all the way down on my cock was music to my ears. She looked so incredibly sexy in the minimal light reflecting into the room through the window. And boy did she like to ride. She pounded me! She grinded, she bounced, she went slow, she went fast. She really got after it. Before long I pulled her in close and started my own assault from below, pumping my cock furiously back up into her sopping warmth and tighness. God fucking dammit it was good! The moans got louder and soon she was cumming all over my cock once again. Fucking christ this woman is amazing.

I let her recover slightly before I started my assault on her pussy once again from underneath. The sexiest little moan once again escaping her lips as she tried to keep relatively quiet.

“I’m on the pill, I want you to cum inside me.”

Prior to this experience, I had never cum inside of a girl bareback. With a condom sure, but we all know it’s not the same. Those words from her started the tingles, and my orgasm started to build.

“Fuck me, yes, fuck me!” “God yes, cum in me!”

It felt like a good 30-45 seconds of build up. Every part of my body was tingling, before the tingles worked their way to my testicles, and exploded out of my cock. This was by far the most powerful orgasm I had ever experienced, and she wasn’t about to let me simply twitch through it in a now convulsive state. She slammed her pussy down on me time and time again as I unloaded jet after jet of semen into her perfect pussy. Holy balls was it intense.

Finally, she relented.

Our bodies collapsed into each other and the giggles started. We were both spent at this point. She must have laid on top of me for a good 5 minutes as we both glowed in after sex delight.

“We should do this again,” is all she said as she climbed off of me and grabbed a towel. Even watching her catch my cum dripping out of her pussy was sexy as shit. She cleaned her self up, then attended to me as I lay, still recovering on the bed. After cleanup, she crawled back into bed with me and wedged her body into little spoon formation. She set her alarm for nice and early, so I could escape undetected back to my room in the wee hours of the morning.

My life got a little better that night.

Thanks for reading.

Source: reddit.com/r/gonewildstories/comments/i60wu7/when_m_living_with_a_female_roommate_turns_into