Author: SayPleaseMiss

My 38 [F] friend 40 [M] on the highway patrol or, “the sundress and the baton”

My 38 [F] friend 40 [M] on the highway patrol or, “the sundress and the baton”

I had known Dominic for a long time. We had actually gone to school together, though he had been two years ahead of me. We shared friends, similar social circles. We’d been about as close as platonic teenagers could be in those days.

I remember not particularly liking any of his girlfriends, and he hadn’t been overly fond of anyone I dated, either. Still, nothing passed between us apart from one very fiery and wholly unexpected kiss the night of his graduation. I think we were both surprised by how we felt ourselves responding to each other, and before we could take things further, we were interrupted by the rest of the party pulling us in opposite directions. In a few weeks, he’d be off to university out of state, and life continued.

I always wondered what had happened in that kiss, and where it could’ve led if we hadn’t been interrupted. Read more »

The Kindergarten Teacher’s son [M] 44 or, The Biggest Cock I’ve [F] 37 Ever Seen

Some things are off limits. Some things are not to be touched. So when you find yourself with your head back, screaming, so full with a cock that you couldn’t believe would fit inside you, it’s not like your “life flashes before your eyes”, but you certainly do wonder how the hell a sequence of events brought you here.

I don’t like blond guys. So plain, so boring. Predictable. Burn in the slightest blink of daylight. Mayonnaise as a substitute for personality. At least, that’s how l felt the winter I turned 18. I was extremely judgmental. I would pay for it later.

I didn’t meet Bryn right away. I first met his mother.

Backing up, his mother, “Mrs. K”, was a kindergarten teacher, and she was really great at her job. She hadn’t been my kindergarten teacher, (thank goodness). She didn’t even teach at my old school. I met her through volunteering, and twice a week I would help out in her class, helping adorable little kindergarteners with their letters, and gluing cotton balls to milk cartons to make little “sheep” during “arts and crafts”…far too wholesome for where this story goes. Read more »

Once upon a time, there was a colleague I, 37 [F], didn’t get along with, but then he 40 [M] locked the door…

Once upon a time, there was a colleague I, 37 [F], didn’t get along with, but then he 40 [M] locked the door…

I was 25 at the time, hungry, getting established after university. I’d decided I was going to stay “heads down”, focus on work, and was steadily rising through the ranks.

Mark was introduced during a team meeting. He was probably one of the better dressed in our office. He was confident, amusing, a bit laissez-faire, but you could tell how he spoke, that he was intelligent, sharp. Not much escaped his notice.

Honestly though, I didn’t think much of him from that meeting one way or the other. (My mind wandered…he had a great body…what was he like in bed, I wonder…oops!) I took a deep breath after the meeting, shook those thoughts away, and just hoped he turned out to be competent, and that we’d work well together.

As time went by, I saw and heard more of him. Some of our projects ran in parallel, so I got to see him work.

He was engaging, and could pull enthusiasm out of people.

He knew what he was doing. Read more »

I 37 [F] was invited to be a couple’s third. 35 [F] 44 [M]

I spent some time in London for work (in the before covid times), and tried to get out and explore whenever I could. London is an amazing global city, you can experience nearly everything there.

Nora (35 F) and her husband Joe (44 M) had recently married, but had been seeing each other for nearly ten years. Nora had laughed when she told me getting married had been a “formality” more than anything, they said they’d already experienced most of what being a couple could entail. Mostly.

I knew Nora from our time together at university, she had been my roommate once upon a time, until she moved off campus. We’d kept in touch over the years, and when I realized my trip to the London office would mean we could see each other again, I was so happy. Nora and I had been very close as roommates, and I was looking forward to rekindling the friendship. Read more »

I 37 [F] provided unplanned entertainment for a bachelor party 40 [MMMMMMF] at a BDSM club

In most major cities around the world there is a club. There is a bouncer at the door, a line out front. ID check, cover charge, stamp on the inside left wrist. Most clubs are like that, and some even have a red velvet rope out front. Not here. Thick black velvet ropes stand guard by the door at this club, large gentlemen in tuxedos or black leather are the only ones who may touch these ropes. Invitation only.

This club specializes in bondage, the BDSM lifestyle, exhibitionism, all the naughty things your heart desires, but were perhaps too shy, too afraid. But aren’t you curious?

Many were here to dance. Most were here to view the open dungeon, blissfully aroused humans strapped with sloppy smiles to St. Andrew’s crosses or wooden horses, all manner of delights on display. Be open, be respectful, be free, you either have consent or you don’t, no cameras or phones allowed. Read more »

I 37 [F] slept with my boyfriend’s 38 [M] dad 58 [M]

I should say that all this started when I turned 18. I was very sexually conscious, horny ALL the time, and experiencing sex for the first time legally and uninhibited. After a few okay encounters (still a few good ones of note) with men my own age, I found myself gravitating towards older guys. It started with men in their 20s, then 30s, etc. Dads were constantly checking me out, and I couldn’t lie, I liked it.

One such experience was a mind-blowing experience for me, and also remains a favorite. He was this incredibly “hot dad”. Big arms, hands, incredibly strong and completely wicked. His hair was still lush and full, and he had these small white streaks at his temples, it was such a turn on. His wife had passed away many years prior, and while he had been without sex for awhile, I was just getting started. A perfect storm. Read more »

I 37 [F] slept with my boss’ 22 [M] son

This happened a few years back…I slept with my then-boss’ son. I wouldn’t actually say “slept with”, more accurately, it was some of the most dirty and passionate fucking I think I’ve ever experienced. Top marks.

At the time, I was in my late 20s/early 30s (I’m 37 now), and I worked for one of those companies where everyone not only knows everyone, but you are social outside of work, too. It was normal for us to go to an event, or casual meal, or late night beers around the fire pit at the boss’ house.

I was often at these events, and when I first started at the company, I knew my boss had some kids, but we didn’t really see them except in passing (some high school and college-age), though it was “known” that he wanted his son to join the family business. During an off-site, my boss wanted me to connect with one of our partners for an event we were putting on at a hotel, and oh my goodness. This guy was incredibly tall, fit, confident, well-dressed, sexy, and did he have a killer voice! He was so attractive that my normal professional and polite indifference went right out the window. Read more »