Spontaneous sharing of [M]y then [F]wb with ]M]y neighbor

My first post here. To give some background, this happened years ago. I had just gotten out of a very toxic relationship and was “going wild” so to speak. I was also working as a part time bouncer at a strip club and occasionally as a driver for an escort agency.

I met “Mary” at a New Year’s party, shortly before my relationship ended. She was about the same age (early 20s) and was fairly inexperienced only having had sex for the first time a few months prior. She had a boyfriend but hadn’t sealed the deal with him and broke up with him to fuck me a few weeks after I met her. She wasn’t what you’d call hot, but she was attractive, long wavy blonde hair, a nice figure and some small curves. She was also very enthusiastic about pleasuring me too.

My neighbors at the time were a group of guys who had moved here from out of state and had been high school friends. I lived in a college town then, so it wasn’t unusual to have new neighbors every year. They had frequent parties, and were fun to hang out with. Their 4th roommate was a local guy named Deon. He was older than all of us, and seemed kind of awkward around trying to pick girls up. He was kind of a skeezy guy but nobody really disliked him.

At one of the usual weekend parties I showed up with Mary, she wasn’t a big drinker really, but came along anyway. During the party, one of the roommate’s girlfriend’s friends had left, but had texted me to come over to her house that night. Being in my “gone wild” life, I decided to. Problem was I had Mary with me. As the party was dying down, I made an excuse to leave and told Deon privately that if he wanted to try with Mary he could, but if she didn’t go for it then it was on him. I left them alone and came back hours later.

The way the house was laid out was unusual. There was a massive living room that had sort of an alcove with a couch in it, but unless you walked directly past it you couldn’t see anything. There was a main couch that I found Deon and Mary on, and nobody had done anything. All he had done was succeeded in getting her slightly high. I shrugged at him to kind of say “I did my best, sorry” and I started to walk towards the door with Mary. But being in my state and how she was feeling, we made it to the couch in the alcove and started getting naked until I had her riding me. I had only used condoms with her once, the first time, and after I made sure she was on the pill I started finishing inside her.

After about 15 minutes, Deon had gotten up to use the bathroom and saw what was going on. Mary’s back was to him, and he gave me a look kind of asking if he can try to get something, and I shrugged at him kind of like “You can try”. So he comes over and started to fondle Mary from behind. She was startled and looked at me through her pleasure face as if to ask me if this was OK and I grabbed her ass as if to reassure her. By now Deon had pulled his dick out and she was slowly sucking him while riding me even more furiously. She couldn’t vocalize it, but she was so surprised and it made her tighten up and squirt a little.

I leaned back on the couch with her on top and maneuvered her ass towards Deon who taking the cue, plunged his dick into her ass. This was the first time she’d been DP’d and she gasped at the feeling. After a few minutes, Deon asked to switch positions, and now she was riding him and I went to shove it into her ass. We had never done anal, she thought it hurt too much when we tried, but in the heat of the moment it happened. She was surprised, but fortunately Deon had primed her ass, so it wasn’t as hard to get it in this time.

A few minutes later and we switched positions again, this time with her bent over the end of the couch sucking Deon while I fucked her from behind. By now I was ready to pop and without warning her I came inside her, which distracted her from sucking Deon. As that happened, Deon had put a condom on and had put her on her back, legs up over his shoulders and was pounding her furiously until he came.

She got up and went to the bathroom to wash up with me and we came back out to find Deon fully dressed on the main couch watching TV like nothing had happened. We said our goodbyes and I drove her home. When we got to her apartment, she very sweetly told me how much fun she had, but asked nicely if we could keep sex just between us from then on. I agreed to do that and she went to her apartment and I drove home.

Source: reddit.com/r/gonewildstories/comments/qbaadn/spontaneous_sharing_of_my_then_fwb_with_my