Never knew I was bi or had cravings for a man’s cock until I hit puberty. But my first gay experience didn’t happen until I was in the service at 18.
Before the internet, you could cruise interested people unless you went to an adult bookstore and bought a swingers style ad book. I used to get the hopes to find a hot girl to fuck. Instead, I found myself cruising for TS girls. Figured, since I had this fascination with sucking a dick and getting fucked, I’d also get a pretty girl with titties too!
I found a beautiful TS girl and called her from a pay phone. We talked a bit and she invited me over to her apartment. Once there, the place was dark and hard to make out shapes in the place. She guided me back to her room. We chatted a bit more before she asked what I wanted to do. I told her I never had done this before and I wanted to suck her and get fucked.
She told me to take my clothes off and as I did, she sat on her bed and pulled her panties down and off and unbuttoned several buttons on an over shirt she wore with no bra. Her room had the most light, but was very soft. I could make her out much better in there and my heart heated fast and hard watching this beauty, tease me with her body.
I was completely erect when I pulled my underwear down and already dripping precum. She teased me about being hard saying you are an eager man aren’t you. I would say she was in her early 20s sonwe we’re close in age. I could see just enough of her cleavage and tits to imagine what she’d look like naked. Her long cock, layer on the bed, shaved smooth except for a close landing strip above her dick. It was a spectacular sight and I knew then, that I was bi! I was just as horny and excited for her as I was for any girl that I would get in her room to fuck.
She spread her legs and told me to lay in between her legs so I could face her cock to suck. I remember once her dick was near my face, I could smell the sweetness of perfume and her feminine smell that drove me insane. I grabbed her dick, began to suck on it and almost blew my load the moment it touched my lips. She complimented my technique saying you’ve sucked dick before. Thus isn’t your first time. I told her in fact it was. I had watched lots of porn of cocksucking. I had practiced what I’ve seen on bananas, cucumbers and even a few dildos but never a real cock.
She said, well you do it well honey and pushed my head back into her now hardening dick. After a good 10 minutes of slurping, ball sucking and gagging she asked me if I was ready to get fucked. I told her yes and she had me lie face down on the bed flat and spread my legs.
She told me it was going to hurt but she’d be as gentle as she could. She began to lune my ass and stuck a finger or two in me as well. When positioned herself above me and I could feel her hard dick pressed against my hole, I didn’t know what to expect, but I knew there was no turning back. I remember it hurting like hell at first as she pushed through my tight virgin ass. She pushed my head into her pillow and said scream into it. The pain was also mixed with tremendous pleasure too and soon, once I listened to her and relaxed, the pleasure became all I could feel once I loosened up to swallow her cock in my ass. She began pumping me harder and deeper shortly thereafter. I think she was convinced it was my first time. Because she later told me, I was so tight I had to be a virgin to getting fucked. She never had a virgin ass before and she came very quickly.
After we finished. She apologized for cumming so fast. She’d never thought I was sooo tight and it felt good to her. Though I had paid her for my first experience. She said she owed me a free one where she promised to fuck me longer. I later on went back over where I had a few more cocks I’d sucked under my belt to show her how much better I’d become. But I hadn’t had a dick since her. She enjoyed the head I gave her, and when it came to her fucking me again, she took her time. I was still so tight that she’d stop fucking me so that she wouldn’t cum. As she fucked me, she would reach around and stroke my dick while I was on all fours. She told me to flip on my back and lift my legs as she fucked me face to face with my legs on her shoulders, near my head. By then she was pounding me deep. This also was the first time I kissed a TS or any body other than a girl. It was sooo passionate. I believe she was just as attracted to me as I was to her. Before she began cumming, she pulled away from me and kept fucking me while jerking my cock. She told me to cum for her before she did. I began grinding my hips upward to meet her thrusts and started to moan that I was cumming. She stroked me faster and I began to squirt cum everywhere as she jerked me. My face and chest were covered with my cum and as I was cumming, she began to cum too. She was wearing a condom so I never felt her cum in my ass. We finished and she pulled out of me and came back with a wet towel for me to clean off. I told her how great it felt and how much fun I had. She indicated too that she really enjoyed it, but it was the last time she could see me. I asked why and she told me because, she really enjoyed sex with me because I was so new to it and such a nice guy. She told me I was the type of guy she’d look for in a real relationship that she said she was afraid she would begin to like me too much, and it would be weird to 1 pay to see her and 2 that she didn’t want to stop getting paid to have sex.
I kind of giggled and thanked her for the compliment. But told her I found her very attractive too and didn’t mind paying her to have sex. I teased her about throwing me a freebie every now and again and she laughed saying, it would be too easy to fuck you for free honey! So as I finished getting dressed. She came out of the bathroom with just a T-shirt on. She had her panties in her hand. She walked up to me, gave me a tremendously passionate long kiss and told me to keep her panties as a memoir of the women who popped my cherry! I remember the last time I looked at her seeing her cock peeking out from under her shirt and the faintness of her tits through the thin sheer shirt before she shut the door. Man what an experience!
