This was a few years ago, during the holidays. I had posted looking for a local woman who would be interested in pegging me. It didn’t take long and I got a response. The person I was speaking to was very shy and sweet so I was excited to meet her but didn’t expect things to get sexual. We met for coffee and we really clicked, she was significantly younger than me, fresh out of college and was also very inexperienced and the sex her and her few partners had was pretty vanilla.
She was also drop dead gorgeous and didn’t realize it. I really enjoyed our conversation but honestly thought that was where it would end. I was even more surprised when we were naked in her room and making out. Things progressed rather quickly from there. At one point she was using hairbrushes in both holes. She demanded I cum on her glass top desk so she could lick it off.
After this went on all night we took the morning to rest a bit, hydrate and eat. Then round two began…the highlight of which was when she asked if I knew any bisexual women who might want to join us. It turns out I did and my date was so attractive our guest didn’t take much convincing. I was pretty well spent though so I spent most of the time with my dick in hand and watching. In fact after a couple hours I decided I needed to go home and left them to their own devices.
The Redditor and I would spend time together every once in awhile for the next few months and the sex stayed awesome. We spent a lot of time sending sexy pics and videos to each other and one point she asked me to leave pics open on my phone and my phone unlocked lying around for my roommate to find it. I could never bring myself to do it. At one point her and I had discussed having a MMF threesome. A couples days later she told me she had gone to Reddit and found a guy. After the three of us chatted for awhile he came over and we had another great night.
After the first couple of nights I had assumed the talk of being inexperienced was all a story. After I got to know her though it was pretty clear she was telling the truth. Despite knowing it was a bad idea I had started to develop feelings for her and let her know how I felt. Unfortunately they were not reciprocated, she thought I was attractive and over all fine enough but the reason for the sexcapades was now that she was out completely on her own she wanted to get some experience NSA with someone she had no future with romantically. She was very self conscious and wanted to be at optimal performance when she met Mr. Right. My heart was a little broken but it was a lot of fun. The female friend that came over and I occasionally still ruminate about how much fun we had.
Almost forgot, we always talked about buying a strap on so we could try pegging but never got around to it.
Source: reddit.com/r/gonewildstories/comments/kaxdf0/met_a_redditor_and_things_for_wildwe_did_pretty