Author: CreativelySexual

[M]y first, and then second, FFFM foursome

Sorry it’s been awhile since my last post. The world has had me down, but I’m doing okay, all things considered. I thought I would cheer myself up by sharing a story from my past, and hopefully cheer you up in the process.

This story is from several years back. It’s a long one.

Imagine, if you will, a time before Covid-19. I was seeing a regular FWB who was just as kinky and adventurous as I am. I don’t want to give away any identifying info, so no names and some omissions. Let’s just call this girl “Tattoos”, because she had a few. She is a very lean/fit “burner” type chick (who had actually been to Burning Man). Small tits with lovely puffy nipples.

We attended an event in the city we live in. It was basically a mixer for kinky and/or poly type folks. People dress in costume, it happens at a bar with lots of couches and dark corners, and everyone mingles to meet other kinky people. There’s no sex on site, but there is plenty of making out. Everyone has to come with another person (partner or friend), and the atmosphere is well monitored to keep everything safe, respectful, and fun. Read more »

The time I [M] had sex in a random stairwell

Another flashback from several years back:

There was a woman I met through a meet-up event for poly-people. We ended up hooking up a few times, and had really intense sexual chemistry.

There was one night we met up for drinks on a week night. The intention was that we could go back to her apartment after for a quickie, but at the last minute, her boyfriend (who she lived with) let her know that his plans had fallen through. So she no longer hand an empty apartment, and I lived in another borough of NYC. We agreed to still meet up and “just have drinks”.

Well, drinks escalated to making out in the bar and lots of hands-under-clothes-fondling. It was not a busy bar, and at some point we could tell that we were being very obvious and everyone was watching us. So that ruled out our hopes of sneaking off to the bathroom together. It was late fall, so it was barely above freezing, but we decided to go for a walk with the hopes of finding a dark corner to continue making out. Read more »

I [M] give memorable hand jobs

Quarantine has me remembering some past exploits, and I felt like sharing one fun memory…

Years ago (probably 6 or 7), my girlfriend at the time and I would occasionally play with other people. There was an older couple we met up with (we were early 30’s and they were probably mid 40’s). We had a lovely evening and ended up back at their place naked and making out. We ended up rolling around for a while and being generally playful. Didn’t quite progress to sex, but managed to hit most of the other bases: trading massages, swapping oral, etc. There was a memorable moment where I gave the other guy a blowjob/hand job that had the two women enthusiastically cheering me on, and when the guy came he was writhing and moaning like crazy.

We only ended up seeing the couple the one time. Flash forward several years: I had moved to a different neighborhood in the same city, and I would sometimes see the woman out and about. Never in a situation where I could say hi (usually she would be across the street, or with other people). Until one day, when I ended up waiting in line at a deli counter and realized the woman in front of me was the woman! She looked at me and seemed to maybe have the faintest of “do I know you from somewhere?” looks. I awkwardly said hi and mentioned that my ex-girlfriend and I had gone on a date with her and her husband. Read more »

When I [m] had a bisexual threesome (mmf) and fucked a woman bareback

I’ve got another true story for you. This one is a year or two after my last story about having threesomes with an older couple.

At this point I’d done a bit more exploring and was seeking out ways to tiptoe more into bisexual experiences. As an attractive, mid-twenties (at the time) guy in NYC, it wasn’t that hard. Dating apps were just becoming a thing (but Tinder wasn’t on the scene yet). I connected with a college age couple a few years younger than me, and they invited me over for dinner. It was super cute. They lived in a building in Brooklyn that was an old warehouse converted into nice apartments with tall ceilings and an industrial decor.

The couple was super sexy. The woman was tiny… more of a pixie. Short, thin, and incredibly cute. She was a dancer, so she was fit and flexible. She had small breasts with proportionally large nipples/areolas. The guy was very handsome. He had long hair, a stubbly bear, and a thin/fit body. Read more »

I [m] was a unicorn for an older married couple [m/f]

I posted this in r/sluttyconfessions but wanted to share with this community too. Hope you enjoy.

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This is from about a decade ago (give or take a couple years). I had just gotten out of a long term, super-vanilla relationship that lasted through the years when most people are dating around and having fun. I was coming to terms with my repressed kinky side and wanted to explore, but I had no idea what my comfort level was, or how to go about exploring. I barely knew how to talk to people in bars, let alone discuss kink.

Thank god for Craigslist. This was before many of the dating sites were any good, and Craigslist was the place to go for the more adventurous options. I posted ads in a few different sections with a few different scenarios (more stories for later), but the first ad that I had any success with was an ad looking for a couple. It was a pretty generic ad, and I had no idea what kind of response I would get. I mostly just put out there that I was curious to explore and would love to help focus on the woman. Read more »