I ALWAYS WANTED TO be a man. I wanted to smell like a man. Taste like a man. Fuck like a man. This might seem like a really weird thing to say coming from a man, but I was not always a man. I’ve always felt like one, just born in a body that said something different than what I wanted it to.
Many years ago I had the opportunity to change my gender. Back in the day, we called it a “sex change,” but today it’s called “transformation” or “transitioning.” After many years of self-hatred and abuse to my body, including suicide attempts, I started taking testosterone in my late 20s. When I finally realized that I could change my gender through the use of testosterone, I was all over it.
I remember the first injection from my doctor vividly. I was his very first transsexual male patient — which put me into a whole new world. I know that I was imagining more than was actually physically happening after that first shot, but that didn’t matter to me. All that mattered was that I knew my life as a man was about to start.
Month after month I started to notice little changes. My voice began to sound like a 16-year-old boy; it was squeaky, like going through puberty again. I started growing hair in places that I had never had before. Even my face started to change with my jaw line and nose. Most of all, I started losing my hair on my head. At first, that was hard, but once I just realized how masculine that made me look, I went with it and just shaved it off.
Along with muscles, facial hair was (and still is) one of the things I always longed for. The testosterone gave me that. I worked very hard on my body at the gym and started developing a new male figure. Where there once were skinny arms and legs now grew new muscles. I was shaped like a man. Surgery came about two years into the testosterone. I opted to get my chest surgery first, choosing a brand new surgery that worked very well for me and left no scars. It enabled me to build my chest at the gym so that it totally developed into a male chest.
At the time, the hardest decision for me was not getting “bottom surgery,” the operation that transforms your biological vagina into a semi-functional penis. Deciding that the “cock” was not for me, I chose to stay with what I was born with. I became a man with a pussy. It was a hard and sensitive thing for me to get my head around, but with time I became proud of my self-made body.
Besides, the hormones were enough of an adjustment.
You see, taking testosterone into a body that physically didn’t produce it made me feel sexually charged in a way I’d never felt before, like being a teenage boy for the first time. All I could think about was sex with women — but then suddenly guys were on my mind, too. The testosterone was so powerful that it began directing my sexual fantasies toward men. It was shocking at first, but as I became more comfortable in my body, I knew I could not fight this urge for cock.
With this, I entered the world of gay male sex.
One day, I finally got the nerve to go to a leather bar in my town to explore my sexuality more. When I arrived at the local leather bar, I immediately felt like a whole new world opened up. Wow, I thought, I am home. Looking back I think this was one of those moments that helped define myself as a man: the raw masculine energy in the leather bar, having sex without a care in the world. I had never experienced such a thing in my life.
But that was just the beginning.
I walked in and noticed that all the guys were watching me with that hungry look. I felt totally out of my comfort zone — scared yet at the same time so horny for what I was hoping would happen. I had experience with the leather scene — but not as a man, only as a butch girl.
I made my way up to the bar and ordered a club soda. I stopped drinking years ago, but I was so nervous that I wished I could order just one. Lots of guys were just standing around — some kissing each other and some staring at me or the other guys in the bar. I noticed guys rubbing each other’s cocks through their jeans or tight leather pants, but what I really picked up on were the guys going to and from a room near the back. Of course, I knew what was going on in there and really wanted to head over but couldn’t get myself to move in that direction.
Suddenly, I heard a guy behind me say, “Hey buddy, haven’t seen you in here before.” I turned to see a dude with the most amazing mustache smiling at me. I thought, “Now what do I do?” I said back, “Hey, buddy.” That was all I needed to do. As soon as we started talking, I could feel the sex.
We talked about the little things like where we’re both from, what you say to waste time before you get to the real talk. Eventually he asked me: “What are you into?”
“Cigars, piss and boots,” I responded — because that really was the first thing that came to my mind. Before I knew it, we were outside on the patio starting to smoke a big fatty. I couldn’t believe this was happening — this hot dude in tight Levis with knee high boots and no shirt, smoking a cigar with me. So then he asked me if he could “worship my boots.”
“Really?” I asked, already knowing my answer. “Of course, you fucking can.”
He got on his knees and started licking my leather with such a passion that my pussy began to ache with sex. My little cock began to pulse and grow as he licked away. I saw the desire in his eyes. I saw his cock, which was bulging out of his tight jeans. I started getting more and more turned on — when all of a sudden I realized that this might go farther than just a boot-licking session. I had a choice I needed to make here. Should I tell him that I am a man with a pussy? Or should I just let it go and see what happens?
I am the type of guy who’s all about truth and honesty. I didn’t feel like it would be cool if I didn’t say anything, and it could have possibly turned into a bad situation if we got down and dirty and my pussy was a problem for him, which I was almost sure it could be.
So with all my might, I reached down and grabbed him by the hair, whispering in his ear. “Just to let you know: I have a pussy,” I told him. “I am a transsexual man.” He moved back from me and looked up, still on his knees and said, “I don’t understand.” Of course he didn’t. Trying not to ruin it, I said, “I was born female but had a sex change to a man and kept my pussy. If you’re still interested in playing that would be cool, but if not, I totally understand and we can just move on. No hard feelings, buddy.”
He looked at me and replied, “Well, this is totally new to me but you’re super hot and you feel like a man to me. I would love to still play — if that’s okay with you, sir.”
It was on. No looking back now. My first sex experience in a men’s only place was happening — now.
I pushed his head back down to my boots, where he began to lick. My crotch continued to grow and get wet. My boot wandered to his hard cock and started to rub it as he looked up at me with puppy-dog eyes. I forced his head into my hard pussy and he started sniffing and licking through my jeans. With the cigar in my mouth and this boy in my crotch, I felt like the manliest man on earth. I told him to come up to me. We started to kiss with such force that his mustache was burning my face. It felt so good.
The taste of cigars and sex was all over us. I started to rub his hairy chest with my hands looking for his nipples as he asked permission to do the same on me. We rubbed on each other like this for so long that I lost track of time. Eventually I looked up and saw guys watching us. This made me feel weird, as I was so not used to public sex. However, I shut my eyes and continued to play with this boy. The feeling of man-on-man sex was something I had been longing for during all my jack-off fantasies. Now it was really happening.
I so wanted to feel his cock in my mouth and his mouth on my pussy with that big thick mustache rubbing on my belly.
I could feel the heat coming off our bodies, as we continued to kiss and rub all over each other. I grabbed him by the neck and looked him in his eyes. “Open your mouth,” I commanded, flicking my cigar ash into his dark hole. He thanked me. I told him that we were going to another room. “Are you okay with that?” I asked. Even though I was still nervous, it was as if I knew what I was doing all along. I guided him by the neck to the back room where it was dark but light enough that I could see lots of other guys sucking each other off. The air was filled with their sounds.
I had no fucking idea what I was going to do. I just knew that I should go to this room and see what happens.
So I put him on his knees again and told him to start licking my boots. I unbuttoned my Levis slowly, so scared and so hard at the same time. My pussy was wet with excitement. I pushed him down just enough to let him meet my hard pussy before pushing his head toward it. I do this not too forcefully just because I am still convinced he’s going to freak out on me. However, he slowly moves towards me and starts to suck my hard little cock. “Oh, shit!” I yelped. “Shit.” I’ve never felt anything like this before. His moustache rubbed me, and his mouth sucked me so hard; with all this friction, he was about to make me cum all over his face.
I pushed him back and asked him if he was enjoying himself. He responded, “Please sir, may I continue?” I pushed him back in.
As I was experiencing this amazing feeling I opened my eyes and saw a couple guys come over to watch us. This just made it hotter for me. My nervousness turned into aggressiveness, and I started fucking his face while the other guys started to kiss me and play with my nipples. I wasn’t sure if they realized that he was sucking on my pussy or not, but no one seemed to give a shit. I didn’t give a shit. And then in that moment, I came.
I pushed him off of my pussy and pulled my Levis up. The other guys had their bulging, hard cocks in their hands stroking, all so fucking hot. I pushed my boy towards them and he started to suck one guy while I kissed and played with their nipples. I wanted to suck cock so bad, but I didn’t feel confident enough to go there just yet. So I didn’t.
I continued to play as the boy sucked them, and slowly I removed myself from the group and re-entered the front of the bar — in some kind of sex haze. I felt like I needed to leave before I was found out. I am not sure why, but I suddenly felt uncomfortable, leaving in a rush, never to see that guy again.
I still think of him. I wonder if he thinks of me.