Author: thisismypdxthrowaway

I [M] [F]ucked My Roommate’s Tinder Date

Not my finest hour—please don’t judge…

When I moved from the West Coast back east a few years ago, I rented the upstairs area in a house to save money and buy some time to figure out where I wanted to live. My roommate was a single guy in his late 30’s, and tended to date younger. He was tall, good-looking, and successful, so he was always out with this or that girl, many of them ending up back at the house.

One evening I was still up and in the living room watching TV, about to go to bed, when he came home with his latest catch. She was in her late 20’s, brunette, really pretty face and great, petite, fit body. They had clearly had a bit to drink, and he opened a bottle of wine for them and poured me a glass as well, so I stayed up a few extra minutes and chatted with them before heading upstairs to give them their privacy. Read more »

I [M] [f]ucked my SIL at my in-laws’ house

My wife (at the time) and I attended an event for a close friend of her family, and most of the family was there—her parents, 2 brothers, 2 sisters, and all of their spouses. The event was at a big open hall, and there were probably 100 people there.

I had met this particular SIL several times (she was my BIL’s wife) but didn’t know her well. We got along just fine, and no tension good or bad existed between us. In other words, a pretty normal unremarkable relationship between in-laws. Until that event.

On a few occasions, we found ourselves standing next to each other, just the two of us, kind of watching the goings-on. My ex’s family is rather…dynamic…and we were “outsiders” being that we had both married into it. We mostly made comments to each other, chuckling about this or that crazy sister. But there were a few moments in the silence between where there was the presence of….something. A connection, definitely, being married into this crazy family. Read more »

I [M] secretly fucked a married woman [F] at a Jamaica resort

This is a true story that took place about 15 years ago. I was at an all-inclusive resort in Jamaica (not Hedo) for a much-needed week of rest, relaxation, and enjoying the beach and ocean. As part of the all-inclusive package, there’s an “excursion” day, which is essentially a sight-seeing drive around the part of the island where this resort is, including stops to buy chatchke’s from the locals. On the van, I sat across from a couple that looked a little younger than me (40), and struck up a conversation with them–totally innocent and innocuous.

They served drinks at a couple of the stops we made, so by the time we got back to the resort, we were feeling pretty good. We all (the whole van) had dinner as a group when we got back, and after dinner they said they were headed to the resort’s hot tub and asked if I wanted to hang out and keep drinking. Of course I said yes. Read more »

I [M] fucked my friend’s mom [F50’s] the day I met her

This goes back a number of years to just after college, when I was 23. One of my friends from college moved back to LA after we graduated (I was in SF), and the following Memorial Day he invited me to spend the long weekend with him and his (divorced) mom and sister in Palm Springs, where his mom lived. Memorial Day in Palm Springs is one giant party so I totally agreed. Let’s call him Mike, and his mom Brenda.

I flew to LA and met Mike, and we drove out to Palm Springs to his mom’s house. When we got there, his sister and her friend were already there. I’d never met Brenda before–she was petite, about 5’nothing and in great shape, short blond hair and a tight little ass. The plan was for all of us (except Brenda) to go out partying in Palm Springs. The dagger in that plan came in the form of some really potent weed that Brenda had for us all when we got there. We spent the afternoon smoking and chatting, with me reclining on the sofa and Brenda sitting on the opposite side under my feet. Nothing overtly sexual going on…just a little incidental contact with my feet. Read more »