This story dates back to a few years ago. I 31M had been peaking in what many would call a hoe phase, being a fuck boy or whatever other term you would like to use. I had gotten out of a year plus long relationship that ended when we realized it just wasn’t a long term fit and I decided to explore the open market.
I did exactly what I’m assuming most men do (correct me if I’m wrong) and did two things right away:
1. reached out to a former ‘sure thing’
2. Fired up the dating apps
Although I had great success with number 2 this story is about item 1, Holly.
Holly and I had hooked up a bunch prior to my relationship and although she willingly and repeatedly reached out to me while she was coupled up I didn’t stray from my partner. Once my relationship ended, and she heard I was back on the market, she reached out the next day and two days later was back in my bed. Holly would best be described as the poster girl for r/petitegonewild with a slim frame, toned stomach and proportional breasts and bottom. She had long, dark brown hair and a mischievous smile. The sex, as always, was great. We picked up where we left off over a year before with her squirting time and time again into my hand and screaming out for daddy to fill her with cum and get her pregnant. This girl really did something to me.
We kept this fling going when she could sneak away from her boyfriend. There was no confusing that this is what we were and what we would be, a sweaty pile of intertwined nudity. As we continued this game I fiddled around on the dating apps, finding a few promising dates and one consistent fwb. This friend with benefits knew about Holly and visa versa and it seemed to bring the best and filthiest out of each of them. Trying to tire me out or drain me of all bodily fluid so that I wouldn’t have enough energy for the other. This was my sexual peak. I had reached the orgasmic pinnacle of my life and there was no mistaking it but I felt… empty. My dating app tendencies switched to looking for a partner that I would spend time with OUTSIDE of the bedroom. I found one, but it took weeks for our schedules to align before we could meet up for a drink and bite to eat.
The day before my real date came and I knew that my time as a single man would likely come to an end so I did what only made sense at the time. I texted Holly “come over”. She was at my house that night and up to her usual antics. Her carefree sexuality hidden behind her mischievous eyes. We started fooling around in the living room when an idea came to me; this may be our last time together and it needs to be documented. I pulled out a large, high quality camera I had and she nodded her approval as she began so lick up and down my shaft. The pictures are almost comical. This tiny girl with her hand trying to fit around my shaft, her mouth just barely closing over the head of my cock looking completely stuffed. Her hunger oozes through her eyes in the pictures, even now. They’re engrained in my brain as she looked up at me from her knees, licking, lapping and sucking with enthusiasm. She looked possessed as we reviewed the pictures later. Like a demon trying to suck your soul out through your dick. It sounds ridiculous as I write it.
We ended our session with her pert ass sticking up at me in doggy snapping a few pictures with just the tip inside of her. Her grip on me so clearly evident. I put the camera down and laid into her like it would be my last fuck. My left thumb plunging into her ass and my right hand leaving it’s outline perfectly on her right ass cheek. I buried myself all the way as I creampied her knowing that she’d be carrying that load back to her boyfriends apartment. It was the last one I’d give her.
Holly and I haven’t seen each other since that day. The next day I met with the girl from the dating app and it was everything I hoped it would be, and still is.
Source: reddit.com/r/gonewildstories/comments/xa06yi/one_last_hurrah_mf