I thought it’d be fun to tell a bunch of real stories from past experiences. I’ve been trying to do nofap lately so this is kind of an outlet for me. Enjoy!
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If you haven’t already, please feel free to read [part 1](https://www.reddit.com/r/gonewildstories/comments/lnrk95/the_time_i_m_ended_turning_my_roommate_f_into_my/) and [part 2](https://www.reddit.com/r/gonewildstories/comments/loe0k7/the_time_i_m_ended_turning_my_roommate_f_into_my/) of this story.
The FWB relationship had gone on for about 9 months. Over this time, we had gotten close in terms of hanging out in addition to intimacy. At the peak, we were fucking multiple times in a day and since she was my roommate, it was really convenient and easy. At the same time, we had separate lives as we started expanding our respective friend circles. I had a feeling she wanted a proper relationship but I wasn’t necessarily interested even though we had developed a closeness. I started meeting and hanging out with more women and eventually, one of them interested me enough that I decided to call it quits with C.
It was a rough and emotional time. C had definitely developed deep feelings for me during this time, feelings that I couldn’t reciprocate, but I was clear about moving on. After I told her, we stopped having any intimacy for about a week. During this time, we would talk and it really wouldn’t get anywhere. Emotions were all over the place and I knew nothing good would come out of this but it was kind of a transition period. One night, a week later, she to my room and sat on my bed just talking to me. It was the first time in a week where it was like old times. She basically just said she was sad but she has accepted it and knows it was time to move on.
She left my room for a minute, only to come back wearing a dress and a pair of heels. It’s a pair that I liked. One of those black, 3-in closed toed heels that women would wear with a nice dress on a night out or with sexy business attire for the office. She knew it drove me crazy. “Let’s do it one last time. Kinda like a good bye,” she said as she sat back on the bed and wrapped her arms around my neck. I couldn’t say no to it. She pulled my face to hers and kissed me, as I brought my hands to her body. I could tell she wasn’t wearing anything underneath the dress. “Fuck me one last time,” she said, as we lay down, her on her back and me on top of her.
—– Sex begins here —–
She held herself up by her elbows, looked up at me with a “fuck me” expression, and spread her legs. Her muscular legs splayed out, welcoming me. Her black heels framed this sexy pose, like I had just taken her home from a club, threw her on a bed, to be immediately defiled. Her legs always looked amazing in heels. They made her muscular thighs and defined calves look so sexy and inviting to slip in between. I hiked up the dress to reveal a nicely shaved pussy. Her bare, meaty lips lay before me as I bent down to kiss them and take them in my mouth. I sucked her her lips and her clit for a few moments before I could no longer take it. She didn’t prefer to cum via oral anyway.
I slid forward and rubbed my engorged head on lips. She reached down to caress my thickness, tugging gently and lining it up with her hole. I hovered above her with both hands holding me up while she slowly rubbed my cockhead against her impossibly wet hole and lined it up. I didn’t have to guide it in myself. The hole was so wet that my head was going guide itself. With that, I pushed forward. There was little resistance as I plunged slowly into her wet warmth. As I started slowly thrusting in and out of her pussy, she got emotional. “I’m going to miss you so much,” she said, as I continued fucking her at a slow, steady pace. I pulled it all the way out then push it to the hilt, trying to feel her walls and savor the passion of the moment. “Your cock is so right for me. It fits me so well.”
Eventually, I picked up my pace. Her breathing quickened as she neared her orgasm. She alternated between opening her legs wide for me, as I fucked into her, and wrapping them around my back. I put my head down into the head and fucked down deep into her as she started gasping and moaning. I lifted my head and watched as her eyes started closed but her mouth opened and her face contorted. “Oh shit!” she exclaimed as she came from my cock pistoning in and out of her. She shuddered and her legs tightened and clamped me as she kept her mouth open in the ecstasy of her orgasm. Finally, it was over and she once again relaxed, opening her legs again to accept my continued thrusting.
I sat back, grabbed her bunched up dress and pulled it over her head. She was now fully naked and I sat back and enjoyed the view of her firm B-cup tits with ultra protruding nipples. I grabbed both her globes with my hands and massaged them roughly. Her long, hard nipples filtering between my fingers. I leaned down and sucked and nibbled on those nipples for a while as I continued to slowly thrust in and out of her wet pussy. Finally, I started getting close so I got down closer to her and started going in and out at a more rapid pace. This caused her to resume her heavy breathing and gasping.
I was thrusting hard and fast and started reaching my vinegar strokes. As I got close, my thrusting abruptly stopped and started as I approached my orgasm. She was used to this. I had mentioned in part 1 that she had initially not even let me orgasm inside her with a condom on. Over the months of daily fucking, she relaxed her rules and had grown used to feeling my last few strokes before I would bury my cock deep in her shaved pussy (which she had started shaving for me) and coating her insides with shots of my semen. She told me she loved the pulsating feeling of me painting her walls and filling her up.
This time, she sensed it and flinched, pushing herself backward. It was an emotional reaction, like the emotions of me cumming into her would be too much. Or maybe she felt I didn’t deserve to cum inside her one last time. She did this and it all happened in a second, but she said nothing. She only looked down at where my cock had been pistoning into pussy. I was in the throes of my animalistic approach to orgasm. Her flinch had been noticed by me but I was like a runaway freight train. My dick fell out for a second, mid thrusting, before I moved forward slightly and thrust it back into her now wet, well-fucked pussy. C closed her eyes as I buried my face into her shoulders for my last few strokes. Her legs, still wearing her heels, widened to welcome my climax.
I grunted as I hit my orgasm and, like many times before, I buried my dick to the hilt inside of her and drained my balls inside her pussy. She gasped as she felt the pulsating warmth of my cum flooding her insides and she wrapped her arms around my back. I kept my dick inside her as it pulsed gently, after I shot several ropes into her. I pulled out and some of our juices instantly slipped out. She was already impossibly wet and with the addition of my cum, a fair bit would drip out and stain my sheets. She smiled at me as I looked at her then her face went neutral, probably with sadness.
We eventually cleaned up and we hugged and talked a little bit more before she went back to her room. I dated the “new girl” for a little bit but that turned out to be a disaster. There were others later on, but C would come to be the closest thing I had to a proper girlfriend during those few years. We’ve lost touch for many years since and I always look back upon the experience with a mix of regret and sadness. However, I’ll never forget both the sexual experience and brief period of closeness that we had together.
Source: reddit.com/r/gonewildstories/comments/ltv5az/the_time_i_m_ended_turning_my_roommate_f_into_my
That’s the hottest breakup sex I’ve ever read. Bravo! Loved that you pumped her full of cum as a parting gift. The level of intimacy you two had was unreal
Why not try to find her and reach out? Worst case is your life goes on as it is now. Tell her you regret treating her the way you did when you were still emotionally immature.