I had moved to Florida and built a house just as the market crashed in 2008. I lost a beautiful house, a slutty wife, and every dime I had all in about 6 months. I suppose I had always had a suppressed gay thing going on and was at a point where I thought, what the heck, at least I will test the water. I didn’t have much else going for me but freedom right then. I figured at 50 I better experiment while I still had a little tread left. I also figured Florida might be happy hunting grounds with all the older horny guys that had wives no longer interested in sex.

I started cruising Craigslist thinking it would be easy to find the perfect match. Boy, was I wrong. 98% of the ads were either spooky or laughable, usually both. STDs did not appear to be of much concern to anybody either. The very few I did write sent back such ignorant, crude, and barely literate replies that it was kind of shocking and depressing at the same time. I decided to wait for that perfect pitch no matter what. I was working long hours too, so I did not have time to waste as it was. I had a very specific fantasy in that I wanted to be the ‘girlfriend’ of some older man who was missing sex. However anal was off the table and I was only interested in kissing, mutual masturbation, oral, crossdressing, and whatever else came up naturally. I wanted to make love, not just perform hardcore gay sex. Yet, I was not looking for a gay relationship outside of the bedroom, just meeting for casual sex occasionally. I also knew I wanted a ‘boyfriend’ who was taller than me and well hung, as I was hung like a light switch and felt it would make me feel more ‘Girly’. I think my Craigslist personal was failing because what I was seeking was so unusual. I was about ready to throw in the towel.

Then one reply caught my eye. A 63-year-old man, married with an ill wife, had never had gay sex before, and figured at his age getting a woman would be pretty hard. He was looking for a man to act like a woman in the bedroom. He wasn’t interested in any anal, only making out, kissing and oral. He had a condo down here and his wife was up North. He was down here for season for a break from caring for her. His kids demanded it. He was clearly nervous about answering a personal. He had also gotten some scary and wacky responses and was about to give up, until I answered his inquiry.

We clicked right off the bat. John could write and express himself beautifully. We started out slow and it slowly got more erotic as we continued to write. We exchanged photos and they also got more xxx as we progressed. I started to send John little video clips of what I would like to happen between us. Ironically, they were all heterosexual video clips, as gay porn did not turn me on at all. It was all pretty vanilla really, just kissing, fondling and oral mainly, and very slow and gentle for the most part. We were both nervous about meeting, but it was building up to it for sure. Turned out that was the best approach in retrospect and John was not really into gay porn either. We both knew exactly what to expect and what our roles would be. One day I just wrote him an email and said I think the time had come to consummate our relationship. We set it up for 4 days away, as that was my first day off.

I decided not to masturbate for those four days so I would make sure I was horny, considering I was still jacking off at least once a day for years. I got up and took the best shower of my life and trimmed up a little. I decided to wear just these red swim trunks I had and a tee. These trunks made my legs look nice and tan and they had the built-in web underwear. I figured I wanted to make taking my clothes off as easy as possible. A tin of Altoids for some fresh kissing in my pocket and I was on my way to John’s condo. One part of me was nervous, yet one part was pretty relaxed because we had written so much, exchanged photos and really got to know each other. I had to drive through a security gate and finally found his place in this huge complex. I parked and went up to the door and knocked.

We had already decided before hand to kiss each other as soon as we met as to break the ice right off the bat, kind of like jumping in a cold swimming pool all at once. He opened the door and looked exactly as I had pictured him from all the photos. John was 6’3”, handsome, and in good shape, and big enough to make me feel petite! As soon as the door was closed, John embraced me and laid one right on my mouth. That was all it took. I opened my mouth, and we kissed deeply, and I let out a little moan. That excited him more. I could already feel his hands on my butt and some hardness between his legs as he pressed against me. It was all quite amazing and quick. John led me to the couch, and we really went to it.