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.

Repost: Getting my brains fucked out, because I hooked up with my GF’s sister [MF]

I posted this a while back, but had to delete it for reasons. I am just reposting this now as requested by some.

After I had finished school I started to work in a nearby town. Working there I fell in with a new group of people. We liked to party whenever the opportunity arose. It was a pretty wild time. I had a few regular FWBs among whom was Liz. We didn’t know each other that well outside from occasionally getting drunk together and fucking like rabbits.

During a party I met Amy, her younger sister and my now girlfriend. I didn’t know at the time though that Amy and Liz were sisters. I really liked Amy so I didn’t tell her about me and her sister. And when Liz got wind of us dating, she didn’t say anything either.

Fast forward sometime we were on a road trip with Liz and a friend of hers. During a night out and after copious amounts of alcohol, the fact that I had banged Amy’s sister got out. Liz made a drunken comment about this being like the good old days, when we got blackout drunk minus the fact that now I would bang Amy into oblivion instead of Liz.

A morning shower with my sister

I pulled my pillow over my head hoping for a few more minutes of precious sleep as my sisters alarm blared from across the hall. The all to familiar sound announced to the entire house that it was 5:30AM. I heard the soft sounds of shuffling as she struggled in the dark to silence her ringer. Finally, after an agonizingly long amount of time, she managed to snooze it before plopping it back down on her nightstand and continuing her slumber like nothing had even happened.

Dawn hadn’t yet begun to show through my curtains but I know that as soon the suns unforgiving rays peeped through, it would be the end to whatever hope of sleep I had left. I had just started to doze off when her alarm pierced the silence yet again jerking me fully awake. She silenced it and and once again I heard no sounds that implied she had any intention of getting up. I was now fully awake and my bedside alarm clock read 5:45. I wasn’t supposed to be up for another fifteen minutes but here I was staring into the darkness and listening to the muffled sounds my parents morning routine.

Not Just Another [F]riday [M]orning

This needs to be prefaced with the fact that my girlfriend and I have been talking more lately and opening up about stuff that we want. This has been making me feel more comfortable with myself otherwise I don’t think this would have played out like it did and which makes this such an interesting experience to me.

I was horny all night at work. Like getting so hard I couldn’t stand up from under my desk for a good few minutes horny. I needed to get some. And for some reason, I didn’t just need to get some. I needed to Fuck with a capital F.

So I’m driving home, thinking of all the things I wanted to do to her and psyching myself up because I know I have a Dom side in me but I’d never really fully unleashed it with her. I was also preparing for disappointment because she wasn’t feeling great the day before. She had said she felt better before bed and was probably going to work unless she felt bad again in the morning and she’s always gone before I get home. So imagine how hard I get when I see her car was still there as I pulled in.

Going down on [m]y girl[f]riend in her college dorm shower.

My first time taking a shower with a woman was in college, with Melanie. It was during the summer break, but students could pay room and board and live in the dorms if they were taking classes during the summer (Melanie) or working in the area (me). On this night, it was very late because it was a Friday so we’d stayed up watching movies and drinking. She was drunk, and she was the one to suggest that we take a shower together. I was drunk, and I immediately said yes, even though we were in a shared dorm. She checked to see that no one was in the girls’ bathroom and we ran in there and got into the shower without being seen.

I remember watching the water soak her shoulder-length, dark hair and flow over her C-cup breasts. We took turns washing ourselves and each other for a bit, with plenty of breaks for kissing and touching.

At some point she asked, “Have you ever taken a shower like this before?”

“In a women’s dorm bathroom? No.”

“No, silly! You know what I mean. *With* a woman.”

“No. This is my first time.”

[MF] Being used in revenge

I was recently answering an AskReddit thread about something an SO did that was borderline hot/turnoff. For me it was a girlfriend that would sometimes like to call her exes during sex. It was weird, but it was during these calls that she amped up the kink.

Long story short, this girl was a rebound for me and it ended after a few months because she was bat shit crazy (a red head, go figure).

After we broke up I got a few calls from her where now I was the ex getting called. The first one was hot, and I jerked off while she described how he was fucking her from behind. The second time was a little weird, and I stopped answering calls from her after a certain time.

Fast forward a few months later and she calls in the middle of a Saturday so I answered the call. She wanted to grab a beer and catch up. Against better judgment I agreed and we planned to meet later that afternoon.

Had sex with my Airbnb host [FM] (pic)

Description of me: I’m 28 years old with brown hair and green eyes. I’m 5’5” about 115 pounds. I have a nice butt and B cup boobs. I’ve always been told I’m “very cute.” I’ve gotten “sexy” and “pretty” more in the last couple of years it seems like.

I’ve been traveling quite a bit for work lately. I typically stay in hotels, but there was some sort of mix up this time. My company booked my hotel, but got the dates wrong. I showed up at the hotel in the afternoon and there was no room available for me and there were two major conventions in town, so there was basically nothing available at any hotel within a reasonable radius. I needed to find somewhere to stay for the next four nights. I went to plan b and booked a room at an Airbnb. The best I could find was a private room at this guy’s townhouse. The creep factor always crosses your mind, but he had a lot of good reviews and I didn’t have a lot of options. We communicated about when I would be able to come by to get a key and do a walk-through of the place. I was starving, so I stopped to eat first and then met him about an hour or so later.

The time I titty fucked my girlfriend and shot cum in her mouth. [MF]

This happened nearly 20 years ago when I was in college and was dating a girl I had met online who lived halfway across the county. Let’s call her Carol.

For some background on us, I’m about 5’10”, fit, 160 lbs, and about 7″ but not overly thick. She was petite, about 5’0″, with a sexy body, tight ass, and amazing, perky c-cups.

I lived on the campus of a large state university, but she lived at home with her parents. She would travel to visit me, or I would travel to visit her, at least once a month for a long weekend. When It was her parents’ rule that when I would stay with her, I would sleep on a pull out sofa in their very nice, finished basement, and she would sleep in her own bedroom. Of course, she would often stay in the basement with me until late at night while we “watched a movie” and would even sometimes fall asleep down there with me for the night (although her parents weren’t happy about it the next morning).

[FFM] The Landladies Daughter and My BF. (Threesome/CuckQuean/Sharing & Public Play – LONG POST) – PART ONE OF TWO

Hey Everyone, sorry it’s been so long. I’ve had a break from Reddit for quite a while, sadly I got harassed a bit on here and decided to stop posting for a while.

I’ve snuck back on a bit recently though and got the urge to start posting again about mine and my boyfriend’s ‘sexperiences’, especially those that explore my desire for him to have sex with other women, especially if I can join in too.

So, I’ve dug out something that me and my BF took notes on and had already partially written up, as I was planning on posting this before. This is the account of how we met Jeni and introduced her to our sex lives.

(WARNING: It’s Long)

This happened somewhere around Sept/Oct last year if I recall correctly.

Many of you who read our posts often would have guessed by now, I’ve eventually managed to ware the initial resistance to this that my BF had down, and he’s now much more comfortable with my whole Cuckquean kink. He’ll now tease me a bit more by flirting with other women suggestively when I’m there. He’s quite a good flirt anyway but I can be a bit surprised by other women, however, as I honestly expected more would be put off by a guy flirting with them when his Girlfriend is there also, (I obviously would love it if they started flirting with him, however).

College sexting tension with leads to a fun afternoon. 25[M] 32[F] (cheating)

This is sparked by this person trying to add me on LinkedIn. I have her blocked on every form of social media but I didn’t consider that one. At the time of this writing I’m in a strong stable relationship and I won’t do anything to jeopardize that, so when she attempts to contact me I just block her. But I’d be lying if I didn’t admit that I miss our time playing around.

This one is pretty mild in the scheme of things, but the chase turned me on so much that I prefer it over many lukewarm sexual encounters. This starts back in 2012 I decided to go back to college. I was 25 at the time and living in my parent’s basement. I was in a committed relationship with someone, thin redhead with long hair and freckles all over. She was pretty damn cute and we had some of the best sex I’ve ever had, but this story isn’t about her.

During the course of my education I was older than a fair number of the other students. I wasn’t there to socialize so I didn’t really interact with anyone beyond group projects. Eventually though I took an internship job at the same college and it was there I met another intern, we’ll call her Josie.