Fulfilling fantasies with a fellow Redditor [MF]

*This is a true story. Names have been changed to protect the guilty. Sorry about the length. That’s what he said.*

It all started last fall, but I had been thinking about it for awhile. I have had a pretty wild youth…had some crazy experiences, and some real fun times. My first wife and I had an open relationship, often sharing partners, so even in marriage I was, to put it politely, a bit promiscuous.

That relationship, though, fell through eventually and inevitably. More wild times we’re had as a born-again bachelor.

Then I met Anna. Anna was nearly the embodiment of the perfect woman—smart as a whip, strong-willed, hilarious, and the kindest person I’ve ever known. I fell hard. I’m still falling. She became my best friend. Then girlfriend. Then, four years ago, I married her.

Approaching my late 30s, I convinced myself that I had gotten my wild ways out of my system. That I was ready to put all that behind me and settle down.

What I fool I was, to think I’d be able to.

The time I [M] hooked up with a hot wife [F] while her husband watched

*This is absolutely a true story, but names have been changed to protect the slutty. *

This happened about ten years ago. My cousin, who was more like my sister growing up, was having the fairytale wedding of her dreams in Walt Disney World in Florida. Because it was a destination wedding, and because Disney is so pricey, it was a small affair, as far as most weddings go. Just close family and friends.

Me, being the giant kid that am (even though I was in my late-twenties at the time), decided to take advantage of the location and fly down a week early to live it up in the parks before the wedding itself.

It was supposed to be a surprise for my girlfriend at the time, but two weeks before we were set to go, we had a little disagreement. I preferred she not secretly be sleeping with her ex when she said she was working late. She disagreed.

I cared more about the lying than the cheating, to be honest, but either way, two weeks later I found myself alone on a bus full of families from the Orlando airport to a moderate-priced Disney hotel.
The only people on the bus without screaming, rambunctious kids was myself and the couple sitting across the aisle from me.

My [M] and my gf [F] have fun with others [MF] in a hot tub

I have quite a few wild stories, but I figured I’d start with this one. This is 100 percent true, though names have been changed, obvi. Sorry it’s long, but it is what it is.

This happened about 15 years ago, the summer after college graduation. My best friend, Kevin, was house-sitting for his aunt and uncle for the weekend. It was a beautiful house in the suburbs…they were older and had no kids, and plenty of money to spend on an in ground pool, hot tub, full bar, and even an arcade room.

They were very adamant to Kevin about not having any raging parties, but said having a few friends over would be fine as long as it didn’t get too crazy. We weren’t big on the party scene anyway, so that wasn’t a hard rule to adhere to. So that Saturday, Kevin invites me over to cook out on the grill, use the pool, have a few beers, smoke a little…a real laid-back, relaxing weekend.

It was just Kevin, myself, Kevin’s girlfriend Liz, and a girl that was seeing, Cassie.