Yahoo Personals was my go-to for online hookups when I first discovered online 'dating'. It wasn't so much dating, at least for me, but just a lot of anonymous sex. Mostly just random blowjobs in someone's front seat, but occasionally it took me to a stranger's house for an evening of fun or a naked lunch hour. When Jim responded to my ad, I was intrigued almost immediately. An older man, mostly retired from teaching in a...

A few months back my wife and I traveled to the next state to pick up a small refrigerator. We'd been collecting appliances to complete the remodel of our kitchen and had found one just the right size on eBay, and at a wonderful price. The problem was picking it up. I had recently sold my truck and our car didn't have a trailer hitch, so we decided to rent a cargo van. It was kind of expensive but we figured we'd offset t...

The City Fathers, in all their puritan wisdom, had been trying to get Downtown Book, the adult bookstore located right on Broadway in the heart of downtown Rochester, to close almost since it opened. Finally, it appeared it was going to happen. This had been my go-to place whenever I craved some man sex and I was more than just a little dismayed. After discovering how easy it was to use the video booths to find cocks to s...

At the end of high school I bought a 1957 Chevy 210 station wagon, the first car I actually owned. As I got more and more interested in cars I found I had more and more questions. This thirst for knowledge eventually led me to Dick’s Garage, a small neighborhood gas station and repair shop with a very fast Chevelle parked along side it that Dick bracket raced on weekends. I started hanging out there, talking about cars an...

After the first few weeks and making some interesting connections, my work schedule took precedence over my sexual adventures. With almost no time for clandestine meetings, I suspended my ad in the personals. Work went into overdrive so even a long lunch for a quickie blowjob wasn’t feasible. The lie of working late that I’d told my wife was now the truth. Instead of sucking the cocks of strangers in their cars I was at m...

The personal ads had become my very best friend in my quest to supplement my flagging marital sex life. After my first couple of experiences I got a little bolder and started looking for something with a little different flavor. Perhaps there was someone just as taken with women’s clothes and lingerie. After editing my ad slightly I found a young man who sounded like he might be fun. We decided to meet and talk at one of...

To say my second marriage was a sexual desert would be putting it kindly. Oh sure, at first it was pretty hot but by the time our son was born there was really no reason (in her mind) to continue this ‘unpleasant duty’. It didn’t help that I had other needs. I still yearned for the femininity of being Samantha and the taste and feel of hot cum and hard cocks. For a long time I got by with dressing up in private and mastur...

When I would tell my friends I was going to go visit my uncle they all thought of me spending a boring week with a guy twice my age. That was not the case. My uncle Ken was more like a cousin, or even a brother. He was only a year older than me and the same age as my sister. Visiting my uncle wasn’t a bore, it was cool. We didn’t see each other often, usually only one weekend or so per month and a week during summer vacat...

As most parents will tell you, kids complicate things. This is probably true on a lot of levels but especially when it comes to sex and especially when the kids are teenagers. Whether that’s being modest enough not to embarrass them, being quiet enough when you’re orgasming or just having to wear something around the house it can be a real pain. And as every parent also knows, when the opportunity for some ‘alone time’ pr...

Ever since Rhea found out I was bisexual and heard some of the stories about my past encounters, she had a fantasy. She wanted to watch. If I went off to visit my gay lover, Jim, she would tell me how much she wished she could be there watching. Even though she loved it when, upon my return, I would tell her all the details of my latest tête-à-tête, there was still something lacking. (She’s a very visual woman.) I asked J...

Ever since the first time I felt the smooth skin and stiff heat of a man’s erection in my mouth I was hooked. When I experienced the taste and scent and throbbing of a cock exploding in my mouth and the pungently salty flavor of cum that first time I knew I would love to suck men’s cocks. I was reluctant the first time and very tentatively took him into my mouth but that all disappeared very quickly. The skin was so smoot...

I‘d met David through my (now ex) wife. He lived in the Twin Cities with his partner Dennis. His being gay made it very easy for me to talk openly about being Samantha. He hosted a drag show on Saturday nights at a small gay bar so he’d invited me to come along, meet the ‘girls’ and see the show. I could stay the night so I could go dressed and have a fun ‘girl’s night out’ while he MC’d the show. I got dressed at David’s...

The drive home from the Cities was always long. After work I had stopped at Kim’s to change and emerged as Samantha. I drove to the meeting and then went out for a drink (or maybe two) with some of the other ‘girls’. By the time I was halfway home, my eyes just wouldn't stay open any longer. I decided to pull over in a secluded wayside rest area. If I could just catch a little catnap, I knew I could drive the rest of the...

After high school I got a job at an older hotel in downtown Rochester. Built in 1920, it had once been a pretty posh place with a penthouse, restaurant and lavish lobby furnished in reds and golds and warm oak trim. By the ‘70s it was mostly patients for the Mayo Clinic. As such, working third shift was pretty easy. At 11:00 p.m. the bellhop left and pretty much everyone was in bed so I had the place to myself ‘til mornin...

The party at Trevor’s had been a new experience in so many ways, including the money he gave me afterward. I would have done that and more for nothing just for the opportunity to have that much sex, that many times, in so many ways. Of course, the envelope full of cash didn’t hurt my feelings either! Trevor was on chat the very next day. His genuine concern for me was something totally new and I liked it. We chatted and t...