[MF] How my married office co-worker (41) and I (24) fell into a hot summer fling (very real & detailed)

****** denotes when the action starts

Before I was a bull, before I even knew what a bull was, what cuckolding or hotwifing was, back when I was naive about married women, I had a fling with a married wife (though I’m pretty sure this was her one and only time stepping out). Although I now avoid that kind of set-up, this was a pretty interesting one…

Years ago I accepted a pretty good position at a company you’ve definitely heard of that has around 11,000 employees–although in the headquarters there are less of us, maybe 300-400. We also had traveling representatives for the company who don’t work primarily at the headquarters but do have a role that requires them to spend about a week each month in our office. I’d been with the company for a month and a half when we had a four-day out-of-town conference/presentation in Chicago that about 15 of us from the office attended and about 5 of the traveling reps, none of which I’d ever met before.

I 27[M] have sex with a wife 49[F] while her hubby watches (some humiliation) Pt 2

Following up on my post “I 27[M] have sex with a wife 49[F] while her hubby watches, Pt 1 (long)”, this all happened 5 years ago—the first time at their house with some mild hubby humiliation. The second time was a bit wilder, and while the hubby humiliation wasn’t extreme the mental, subtle play might not be for everyone—just a heads up.

Because they are normal married parents, it took a while for us to meet up again after the first night—life just got in the way, and there wasn’t an opportunity for them to get the house alone. Thus, they decided to get a hotel room on a weeknight “so she could get what she needed”. It was kind of a last second booking, so it wasn’t the nicest hotel (I’ve been surprised by couples booking the Fairmont or getting a suite at the Grand Hyatt) but was totally fine—a Hampton Inn type.

My weekday hotel room sex with a mature kindergarten teacher [MF]

One thing about hooking up with an older woman is that it’s pretty clear this will not evolve into a relationship. Also, it’s just a little kinky–being with someone you theoretically shouldn’t–and I like that, especially because I’m pretty buttoned up in real life.

I was a tall, gawky kid growing up, with glasses and an overbite. Then wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy; preppy with some scruff, 6’1”, brown hair, blue eyes, fit.

I 27[M] have sex with a wife 49[F] while her hubby watches, Pt 1 (long)

No one—not my siblings, not my friends, not the people who live in my building—know this about me: I’ve been having sex with wives/moms for 7 years, with their husband’s permission (and often he watches).

I know it sounds strange and kinky (because it is), but I’m a totally normal, hard-working career focused guy living in a major city. I’ve had a fun life of ballgames, hikes, nights out, weekends away and group dinners with friends (except for the whole COVID thing). I was raised with strong morals and have a great relationship with my parents and my siblings and their families. I grew up a nerd and didn’t really become attractive until college so I’m not a chest-beating, braggy kind of guy—I know what it’s like to not be the center of attention. However, now I’m what would be considered traditionally handsome (6’1″, brown hair, blue eyes, fit, fairly athletic). I don’t go to key parties or sex clubs, I don’t identify as being a swinger or in any kind of lifestyle. I date girls my age, but when I’m single I just…enjoy fucking soccer-mom-and-PTA-wives-next-door in their mid-40s to late 50s (though sometimes a little younger or older), often while their husband watches, sometimes on weekday mornings on their dining room table or over the side of their couch. I can’t believe these things happen either.

[MF] The college boy and the mature mom Pt. 2

Thanks for all the positive notes on my first post–really glad everyone liked it. I’ll definitely get to the PMs soon.

Don’t think I’ve described myself much—I’m 6’1”, brown hair, blue eyes, fit but not ripped. Described often as handsome and cute. All American look.

Again, Kim was in her late 40’s, curvy but not fat, maybe 5″4″ with a cute, youthful face (smooth skin, no wrinkles) and gray and white hair, cut kind of in a fashionable bob haircut. I should define fashionable bob, because it’s basically the hair style that it seems women over 45 have–where it’s kind of longer in the front framing her face and then gets shorter toward the back (I find it the perfect mix of cute/professional/sexy). Medium skin color, kind of reddish like she had a tan that was fading but still had the freckles. She had wide hips and a large, very nice ass that still had some perk to it (though larger than what I was used to), and–by my estimate–double d breasts with fairly large areolas and eraser-like nipples.

[MF] The college boy and the mature mom (very long)

[Repost from my previous account. I’m going to put up a few of my previous posts to give context to some recent experiences.]

Should probably start with a little explanation. As I was growing up I was tall and gawky with glasses and an overbite. Then I was an athlete throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but still understand the perception of not being considered attractive.

This isn’t the first experience I had or necessarily the hottest (though I think it’s pretty hot), but the easiest to write–my first experience with an older woman, which really got me into enjoying older women. I really am into the build-up and noticing details and emotions and hope you are too.

I was a junior in college, fall semester, still living on campus. On Tuesdays my best friend and I had a large open swath of time just after 11am, so we’d usually do something together–go shoot ball, grab lunch, go to a bookstore, lift, etc. For some reason on this cloudy, early October blah Tuesday we decided to go off campus and treat ourselves to that fine restaurant chain known as Chilis. We’re seated at a table next to three women in their late 40’s, early 50’s. My friend and I order our drinks and start looking through the menu.