Fair Skin, Dirty Mind: x-post from r/sluttyconfessions

Given my age, a lot of my encounters started in chat: AOL in the 90s, Yahoo Chat after that until they shut it down. Craigslist came after that, and it didn’t take me long to discover that if I posted an interest in a scenario, a type or a particular fetish, there would be a pretty good chance of a taker. Who knew so many people had all these hidden desires?

Early August, 2017: I was 54. She was 40: Latina, but fair-skinned, with long dark hair and curves for days. That part about the fair skin is important; in the dead of summer, when everyone was tan as could be, I was — well, whatever the word was, I thought fair skin and red lips sounded good.

She had both, according to the pictures she sent. She was in from out of town, visiting relatives about 45 minutes away, and she was going a little stir crazy during the days. I suggested we do something about that. She asked what I had in mind. I suggested taking off a bit early from work, her picking me up, and the two of us going to a park I’d always wanted to fool around in.

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Quick encounter with a housesitter while her friends were asleep upstairs (xpost from r/sluttyconfessions)

April 2007, so I would have been 44 at the time. She was 22 or 23, I forget which.

I was out of town overnight for work, staying at a friend’s house. Friend and his wife were in bed around 1 a.m. I was bored, couldn’t sleep, so I was on Yahoo chat seeing if anyone was on and up for a meet the next day before I had to come home.

She messaged me and sent a picture: Cute, a bit chubby, short dark hair, glasses. She was looking to hook up too. Now here’s the fun part.

She was housesitting for some friends and they had decided to come home ahead of schedule. She was expecting them about 3 a.m. and she wanted me to come over before they got there. It was 1:30 by then, and I’d have to sneak out of my friends’ house and then sneak back in to make it work.

Challenge accepted. I messaged that I would be there in about ten minutes. “Ok,” she messaged — then, just a few seconds later: “Shit, they’re home already.”

“Damn,” I messaged back. “You going home now? Meet there?”

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Be my doll: Another x-post from r/sluttyconfessions

July 2017, so I’d have been 54 at the time. She was … 24, I think. Close to that, at least. Cute, curvy brunette with beautiful wide eyes and a sweet sexy smile.

I’d had the fantasy for some time of meeting a woman who was into the idea of being a real live sex doll — not just to please her partner, but because the idea turned *her* on. I suppose I’d go to Fetlife now for that sort of thing, or maybe even Reddit — but Craigslist it was, at the time.

The idea was simple: She would be mine to pose, to dress and undress, to use as I wanted. If I kissed her, she wasn’t to kiss me back. She was to be silent, unmoving unless I moved her.

She messaged me a day or so after I posted, telling me she had been curious about that scenario for a long time and asking if I wanted to come to her (about an hour away). She also let slip that she would also like to come over to my part of town and play in her car, if I was into car play at all.

If true stories are allowed here, here’s one of a series (xpost from r/sluttyconfessions)

February, 2001. Man, how time flies.

I was back in my hometown on a work assignment, and I was in my hotel room checking out Yahoo Chat to see if there was anyone around who might be a playmate. Bear in mind that my hometown is pretty small, and I still had family and a lot of people I knew there. More importantly, my wife still had family and friends there.

(Why didn’t I stay with family? Simple: The company was paying for the hotel and I needed to be able to work there and tie up the phone lines for my computer. Remember, this was before wi-fi.)

Given the circumstances, (a) the chances of finding someone were pretty small, and (b) the chances of finding someone who either didn’t know me or would be discreet were even smaller.

Even a small chance is a chance, though, and this one paid off.

I’d seen her before, and knew people in her family, but she didn’t really know me. I definitely remembered her, though. She worked at one of the discount stores in town, and I always tried to go through her line when she was working. And yeah, every time I went through her line I thought about fucking her. She was always really quiet, and I wondered if she had a wild side she didn’t show.

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