The best night I ever had on Omegle [MF]

I don’t usually go on Omegle/Chatroulette or any of those sites, but I was bored on a Friday night and was kind of curious, so I went for it. The stories are true, there’s a sea of dicks, but I figured eventually I’d find a girl who wanted to chat, or I’d get bored and do something else. I came across a couple of girls and even a couple, but they all nexted me. I was pretty close to giving up, doing the “ok last one” 7 or 8 times, when I finally came across a girl who didn’t immediately next me. This wasn’t just any girl, though. I couldn’t believe my eyes, but there she was, staring back at me: my ex girlfriend.

A bit of backstory: we had a relatively vanilla sex life. She was a pretty timid nice girl, dressed pretty conservatively, didn’t like to show off or anything. Definitely not the type you would really ever expect to find on Omegle, especially not showing face. Also, we dated for a while, you would think this kind of stuff would come up.

But there she was. I remember exactly what she was wearing. A black semi-see-through top with the outline of her nipples visibly poking out, as if to say “no I’m not here just to chat”. There was also a dildo sitting clearly on her desk. Jesus, I didn’t even know she owned a dildo. I still hit myself for not screenshotting, but I was totally frozen. Deer in the headlights, processing wtf I was looking at. I was also harder than diamond. As surprised as I was to see her, I was also insanely turned on.

After about 45 seconds of just staring at each other, a wide grin formed on her face, and I snapped out of it. We didn’t say anything, we didn’t type to each other, she just lifted her shirt to show me her midriff, and I started stroking my off-screen dick. She started touching herself too, grabbing her boob with one hand and sliding the other down her stomach and off-camera. We slowly started escalating, as she pulled her top down to expose her beautiful boobs and I adjusted the camera to show the tip of my dick. She pulled her chair back and grabbed her dildo so I could see her spreading her legs and using it on herself. (Fuck, how the hell did I miss out on all this while we were together??) I backed up my chair too and showed her how hard I was, stroking silently as I watched her touching and fucking herself. She looked so good. I wanted it to last forever, so I slowed down so I wouldn’t cum. Her head pulled back in pleasure, then all of a sudden, she stopped.

She stood up, looked at the camera, threw her dildo on the floor put on a jacket and left the camera frame. I was very confused, until I realized what was going on.

I panicked slightly, but I was too turned on to care. I jumped in the shower real fast, unlocked my door, dimmed my lights and waited. Sure enough, within 10 minutes, she was in my room, removing her jacket, and showing me her still wet pussy.

“Did you drive without pants?”

“Shh.”

We kissed for what felt like forever, while she stroked me and I felt her up. She pulled her top back down so her boobs were showing, got into bed with me, and climbed on top, guiding me into her. Entering her was one of the best feelings ever, so I knew I wouldn’t last long. It didn’t seem like I needed to, because I’m pretty sure she came instantly. Her back arched and her tits on full display, I grabbed her and went as deep as I could. After a few minutes (ok fine, seconds) of that, my cock started to pulsate, and she could tell I was about to cum. She bent down and kissed me and went faster up and down my shaft, and wouldn’t let me pull out. I did not care. I came hard inside her, and she held me tight, letting out a moan and a soft “fuck” into my ear.

We stayed laying there for a bit, I think we fell asleep for a few minutes, then woke up and cleaned up. We talked a bit about wtf just happened, what she was doing on Omegle, how she goes on quite a bit, and how she never told me. We ended up going on Omegle together later, but maybe that’s a story for another time…

Source: reddit.com/r/gonewildstories/comments/awwq5g/the_best_night_i_ever_had_on_omegle_mf