[M]y third time fucking a married woman. While her husband slept in the next room.

When in my twenties all my friends were getting married and I wasn’t having any luck with love. I got cynical about relationships and stopped respecting them. I fucked a college friend’s wife–more than once (https://www.reddit.com/r/gonewildstories/comments/bfdcac/m_fucked_my_married_college_friend_while_her). I fucked a woman I met online who was engaged and looking to get in one last fling (https://www.reddit.com/r/SluttyConfessions/comments/bcdkm8/i_fucked_his_fiancé_then_i_kept_doing_it/.

Desi was the third woman in a relationship that I fucked. I met her on the kind of crappy free hookup site that existed in a world before tinder. She was kind of a train wreck. She was younger than me, had been a stripper at one point, had a kid with one guy, and was married to another guy. They were getting divorced, but both of them were so broke that they couldn’t get their own place, so they still lived together in different rooms of the same apartment. He had the bedroom. She slept in the living room.

But she was attractive. And really funny in an irreverent way that I appreciated. And we clicked talking about indie and classic rock bands. And I was still relatively new to the area and lonely. All of that is rationalizing, I know. But I’m ok with that.

[MF] So I started screwing a married woman I met on tinder…

Bri is a “hot wife.” At least she wants to be. That’s the goal.

But the reality is that Bri is a beautiful, Latina trophy wife in her early thirties with a couple of kids and an older husband who can’t or won’t give her what she needs in bed. His idea of being “dominant” in bed is the missionary position. His idea of dirty talk is using the word “fuck” instead of asking to have sex.

And so she cheated on him. The first time several years ago when she still worked. It was an ongoing affair with her boss. And she got caught. They worked it out. And she didn’t cheat again. At least not until recently.

She stopped working a while back. Her days are filled with shuttling the kids around, working out with a personal trainer, and tennis at the country club with the other wives. She goes to the spa regularly and has a masseuse. And that’s who she cheated with a few months back. But it didn’t amount to much. Some inappropriate touching. Some dirty talk. She arranged to meet him at a hotel and backed out at the last minute. Then she confessed to her husband.

[M] Fucked my married college [F]riend while her husband slept

The second time I fucked someone’s woman was completely spontaneous. For ten years I’d been the type of guy who only pursued relationships and didn’t have flings. In my mid-twenties, after another relationship didn’t work out, I relocated for a job opportunity and ended up starting a fling with a woman online who was looking to cheat because her man was too vanilla to keep her faithful. I threw myself into being bad.

Around the same time I went back to the city where I’d attended college for a friend’s wedding. Obviously I couldn’t take a date since the woman I was fucking was sneaking around on her man.

I had been pretty good friends with the groom in college. I wasn’t close at all with the best man, Dave, but I’d been drinking buddies with his wife, Rachel, in school. I’d never hooked up with her or even really tried. I was always with someone else. But I knew a lot of people who had. By nineties standards, she was definitely a proud slut. Me and another friend ended up staying with Dave and Rachel because they had a big house with a couple of guestrooms.

Had [M]y way with a virgin sissy in a Dallas hotel room

Playing with people on Reddit is damn near impossible. If you find someone near you or just willing to play virtually there is a higher than they flake out than on any other platform. Fetlife or Tinder are much easier. But there are less people on Fetlife and less kinksters on Tinder. So I end up here.

Lena was posting pics when she first caught my eye. This wasn’t the normal guy in panties stuff. These were full blown photo sets from the lips down. Skirts. Blouses. Dressed. Heels Stockings. Lingerie sets with matching garter belts. It showed dedication. I noticed we were in the same city. And so I messaged and we started chatting.

Some elements of her story were typical. She liked to dress up. She was curious about men, but had never been with one in any capacity aside from a little oral exploration, but that was way back in college before she started dressing up.

I was more fascinated by the atypical things about Lena. That she’d first started crossdressing when a girlfriend has requested it. That the woman had taught her how to dress and do makeup. That she’d been fucked with a strap on regularly.

[MT] The Asian Crossdresser Who Kept Posting on Craig’s List

I’d seen May around on the normal websites for pervs. She was easy enough to spot. Asian. Mid-twenties. Long black hair. Almost always featuring pics in a royal blue corset, stockings, and black heels. Sometimes there were videos. Usually playing with toys are doing a sexy little dance. She never showed her cock or her face. There was never a partner.

The blurbs were typically the same. Along the lines of living with a girlfriend and could only dress up on certain days. May liked pic requests and had links to an Amazon wish list filled with cheap stripper lingerie. Occassionally it looked like someone would buy something and she’d model it in a little video of photos online.

It was probably a year after I’d first noticed her when May started asking for more. There were posts made seeking a sugar daddy. A strangely specific offer to model for a Lexus Certified Mechanic. Maybe she had car repairs she couldn’t afford. Or just didn’t want to pay for.

That’s the first time I sent a message. I told May that I was a very experienced, dominant man and we could have a lot of fun together. I got a couple of responses and a request for pics. May seemed interested. And then she disappeared.

[M4T] Making him dress up in his wife’s clothes..

I’m not the first person you’ve met online.
But in the past it’s always been a let down. Some married guy shows up acting shy and and anxious. Or a big talker with rock hard abs and a huge dick can’t keep up or last as long as he says.

You’re skeptical.

But, deep down, you have a feeling things will be different.

You knew it from the minute you read my ad–direct, to the point, firm. I wasn’t looking to play games. I wanted a sissy to dominate.

I told you exactly what I wanted in the first email. I listed my demands and wouldn’t compromise. I was firm. Commanding. The type of guy you knew could take charge.

I show up at your house and park out front. You just talked to your wife and know she’s a thousand miles away. There’s no chance she’ll interrupt us.

Still, you’re apprehensive.

What if the neighbors see me?

What if someone drives by as you open the door?

But I’ve told you exactly what I want. Any disobedience and I leave.

So when the doorbell rings you step out to greet me.