[M]eeting a sexy cougar leads to a [F]irst date: anal and office sex

I had been in a bit of a dry spell for a month or so and couldn’t seem to break through the slump. All of my go-to apps and sites just weren’t happening. Scrolling through one site I saw a new profile; nothing that stood out, just a close up picture of her eye and a mention of her age – late 40s. Her bio stated she was bored and married – her libido was through the roof and her husband didn’t have the kink or drive to satisfy her. I figured I’d shoot my shot and hope for the best. I took a few minutes to write out a thoughtful response and sent it off. A helpful hint to any men reading: putting even half a bit of effort into replying to posts or messages on dating sites results in an exponential increase in positive responses. You don’t have to be Mr. Sauve, but introducing yourself, responding directly to specific things in their bios, and writing out 3-4 sentences goes a long way towards starting things off on the right foot.

[M]y first MTF trans hookup that opened Pandora’s box.

After creeping for a long time I’ve decided to start sharing some of my sexual escapades. For my first few posts I’ve decided to reminisce on my early experiences with MtF trans women.

For as long as I can remember, I’ve had a kink for trans women. Something about a beautiful woman with a good cock has always interested me. This interest never took on more than the occasional porn search or jerk off session when feeling extra horny and the regular stuff wasn’t doing it.

Fast forward a few years in my early 30’s, I found out I was moving to Hawaii and I was being warned that Hawaii had a very large transgendered population. After arrivingI jumped on dating sites, message boards, kik etc. and noticed a larger open population of trans women oin most of the apps and dating sites. Before long, my horninesss and curiosity got the better of me and my porn searches became reality;I specifically started chatting with and searching for trans women. After a few weeks of chatting, trading random pics, and trying to make a connection I got a promising direct message; she saw that I had mentioned I was new in town and was looking to meet up, but had never been with a trans woman before. We talked about what I wanted to explore what I was open and comfortable with. Things progressed and we eventually traded pictures. Holy shit she was smoking hot. Thin, Hawaiian, tan with a perfect round ass and perky tits. I couldn’t believe it, I hit the jackpot. Our chats quickly turned dirty,e flirted and exchanged videos and pictures over the next few weeks.