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.
My fantasy was to be a man's cockslut and cumslut for five service calls. I figured that would get my desire to suck a man's cock out of my system and I could get back to my life of chasing females and t-girls. That was my plan anyway. I went online and found a bevy of men who wanted their cock sucked, but very few appealed to me. I didn't understand a few of the men who said they wanted me to suck them off but didn't want to kiss and cuddle at all because that's "gay." Like having your cock in a man's mouth is the epitome of being straight?
Then I came across a good-looking Asian man, 12 years younger than me, cleanshaven face, and he was a Top. He lived alone and therefore could host, and he was less than 10 miles away. The clincher was that he reminded me of one of the male actors in some of the t-girl porn movies I had watched. I would watch those movies and wish I were the male porn star having sex with the hot t-girls, but when he was in the movie I found myself a few times wishing I were the one sucking his cock and drinking his cum, but as a male.
I sent him a message saying I liked his profile and thought we might be a good match. I was excited when I got a message back from him a few minutes later saying he also liked my profile and thought we could be a good match. I told him that I had a fantasy to be a man's cockslut and cumslut, but I did not tell him that in my fantasy it was for only five times. He asked me what experience I had sucking cock and I told him that I had only been with three other men a couple of times each but had been with twenty or so t-girls.
He quickly agreed to help me with my fantasy and asked if I could be at his place in one hour. He caught me by surprise with his near-term invitation as I was thinking within the next week, not within the next hour. I had an invitation to come suck the cock of the man who I had chosen over the rest, and all I had to do was be ten miles away in one hour. Sounded perfect to me. His sudden invitation didn't give me a chance to chicken out, and there was no way I was going to flake on him and disappoint him. I liked how he was gentle and kind, but firm and demanding at the same time.
I grabbed my barbell and did a few quick sets and some pushups to try to make a good impression for my Top man. I then showered, shaved, put on my cockring and black thong, tightest jeans and t-shirt, and stuffed my leather collar with an O-ring in my pocket. If I was going to be his cockslut and cumslut, I was going to dress the part.
I headed to his house to give him head and as I stood at his front door I could see him at his computer with his back to me. I knocked at the door and watched as he stood up and came to answer my knock. By the time he opened the front door I already knew that I had chosen the right man to fulfill my fantasy. He invited me in and immediately led me to his bedroom. He was an Engineer and dressed and looked the part, I thought he looked hot and sexy.