Years ago I attended a dinner engagement in DC for work, where I met a striking lady, with whom I became entranced. We chatted the night away, and found we had a lot in common; it seemed as if we enjoyed each other’s company a lot.

After dinner we went our separate ways, my workmates and I were on the way back to our hotel with an ex-workmate who now lived just outside the district to catch up and party on. He was quite happy to tell me and our buddies, that she wasn’t really a lady, but a guy who lives as a woman. I was amazed since I had no idea, and became the center of the alcohol-fueled roasting that continued till the night ended and we all retired to our rooms for the night.

My head was reeling, both from the booze, but also from what transpired that night, and it sparked something else in me. I’ve always been aroused by anal, although my experience was limited to an older lady when I was younger, but that’s altogether another story. I’d always fantasized about both fucking a women’s ass as well as having my ass played with during sex, but I was never attracted to any of my gay friends growing up. However that night I had the most wonderful dream and the first wet dream since my teenage years.

After that, I checked out some transgendered porn, but convinced myself it was a combination of the booze along with my lack of sex for quite some time, in conjunction with my fantasies about anal that fueled that fantasy. I tried to put it out of my mind, yet occasionally my fantasies would wander that way at times, and I would find myself again watching transgendered porn. Then one day while in a local mall restroom I turned from the urinal to see an attractive woman washing her hands at the sink. I took the sink beside her and as I started to wash my hands, trying to act suave.

I said, “I think one of us is in the wrong restroom.”

To which she replied in a deep voice, “No honey, I’m in the right one,” and dried her hands, then sashayed out, those sweet cheeks swinging hard.

Dopey me, I stood there as she dried her hands and left, my jaw on the sink, and the biggest hard-on in my pants, unable to say a word.

I had another sexy dream that night about having a blind date. A dinner date where the conversation started about interesting things in our past while evolving to what we liked, including in the bedroom. The date ended with her inviting me to her apartment where she revealed she possessed more than a genetic woman.

I woke up in the gooey results of my wet dream, somewhat amazed at how much there was, and just thinking about it would give me an erection. It became the subject of my fantasies when I would let ‘Rosie’ release my frustration. I kept envisioning those sweet cheeks in that tight skirt but in my fantasy, I’d take her in a stall and have my way with her.

I considered going to a bar not far away that is supposedly is frequented by transgendered women, but a co-worker I’d shared my interest in special ladies with warned me that if found out it could cause problems with work and I’m too close to retiring to give them an excuse.

However I couldn’t get it off my mind, so I joined a few sites to chat with special ladies, but more often than not wound up putting my foot in my mouth. I learned there is a spectrum of what transgendered woman means, and that most transgendered women weren’t what you’d call versatile, as well as that transgendered porn isn’t representative of reality.

I still enjoy a rousing chat now and again and even bought a toy to play with, a ring with an anal vibrator attached. I made the mistake of wearing it while mowing the lawn one afternoon, but that’s another story.

I’ll be retiring in a few years, maybe I’ll make it to that bar and then just maybe my fantasies will come true. I’ve never been what you’d call good with the ladies, hopefully that won’t be the issue then.