This happened four years after my introduction to gay sex as I wrote about in "Seduced with my First m2m Kiss." I had always thought of myself as a straight man with a kink for crossdressing and crossdressers, but I was sure that was the end of the road on my walk on the wild side. Then an older man surprised me with a kiss and I surprised myself by kissing him right back.
We had two incredibly sexy and rewarding meetings where he introduced me to the pleasures of man to man sex and passion. His kiss released my hidden gay side and I quickly learned that my natural gay role was being a cock sucking bottom. Unfortunately for both him and me, my first gay relationship ended after those two life changing meetings. It ended because he wouldn't agree to have safe anal sex and would not allow me to dress up for him or even wear panties. I met a couple of men after that but never quite captured the rush and passion that I felt with my first male lover and I returned to my pursuit of t-girls and females.
One night I was at a bar with a live band and noticed a woman on the dance floor who stood out from the crowd with her beauty, style, sex appeal and dance moves. She noticed me noticing her while she was dancing and gave me a sexy smile behind her dance partner's back. She might have been smiling at someone behind me but it made my bulge grow regardless. The song ended and the band took a break and as she strutted her hot stuff on the way to the Ladies room she touched my forearm and smiled at me as she passed.
A regular at the bar saw that interaction and made the comment that "she was not born a female." I guess one man's red flag is another man's green light. By the end of the night I was the lucky man who was her dance partner. Some people have gaydar, I think I must have t-girl radar.
We ended up back at her place and neither of us had yet brought up her gender bending identity. We had slow danced at the bar and my erection was the only one pressed between us, I figured her shecock was safely tucked away for later. I was fantasizing about how whe would reveal it to me, would it be like in a porn movie where she surprises me with it by sticking it in my mouth, I sure hoped so. She gave me a quick tour of her place and showed me a picture of her wearing a crown and a sash from a beauty pageant. I asked her what pagent the picture was from and she told me it was a Ladyboy pagent somewhere in Asia. If she was looking for me to flinch she would have had to look at my crotch.
I feigned being surprised but not shocked, I tried to hide my happiness that the warning I received, but did not heed, was true. I had always wondered how one should react to the news that your soon to be sex partner is trans. Saying "I thought so" may be true but sounds cruel. Saying "I hoped so" may also be true but doesn't sound right. I just told her that I thought she was the prettiest and sexiest woman at the bar and that I had been with girls like her before. She said "I doubt you have been with one like me" and I told her she was correct, I had never been with a girl so beautiful and sexy. That's when she told me that she was a post-op transsexual. Well I must admit that I was more than a little disappointed that I wouldn't get to suck her shecock or have her fuck me, but I got over that since I was with a beautiful and sexy woman and she could suck my cock and I could fuck her and lick her pussy.
Besides having a cock, I always enjoyed being with t-girls for their passion, lust, beauty, femininity, and desire to suck cock. I always felt that making out and having sex with a t-girl was more passionate and lustful than with a cisgender female. And this girl did not disappoint, she was a gold star cock sucker and an incredible kisser. She liked getting fucked in her pussy but loved getting fucked in her ass. Her cock might be in a jar somewhere in Thailand but her prostate was still intact inside her cute bottom and she loved having it massaged by my cock.
She may not have had her real cock to fuck me with but she did have a collection of different sized strapons to put in her harness. She asked me which size I preferred and told her to pick the one that best matched her cock. I was surprised when she selected the 7" cock and locked it into her harness. She definitely knew how to wield her fake cock as she fucked me just as good or not better than any previous t-girl or my one male lover had. She was a fantastic lover and we continued our affair for a few months before she moved away.
All those nights of passionate kisses, getting my ass fucked and my cock sucked, but not sucking cock myself, stirred my desires to suck cock again. I thought about trying to meet a pre-op TS but decided I would give men one more try. Was my brief fling with men a few years ago an anomaly or was it still inside me to enjoy being with a man and servicing him and his cock. I wanted to find out, the hard way.
I met my first male lover on a chatline four years earlier, but this time I went onto a website for gay men to find my next lover. From the few men I had met, I had come up with a profile of the man I wanted to meet; 10-15 years younger or older, clean shaven face, a Top but not a Dom Top, and a man who is more of a beta male in everyday life but would be my Alpha male behind closed doors.
