My first ladyboy experience was in 1996 in Bangkok. Me and a friend were on temporary duty there for an exercise.
I'd been stationed in Korea but I'd never seen anything like Bangkok. The sights and sounds of that city are amazing. Best of all for a young military guy was the night life. Patpong, Nana, Soi Cowboy...I'd never seen anything like it. So many go go bars with so many women. Hundreds of girls that wanted to go with us every night. It was amazing and for the first time I realized how backwards and closed minded my own country was. Why couldn't everywhere on the planet be like this?
We were on a 2 day binge already the night I'm about to tell you about. A binge of booze and pussy. I'm not sure how many girls I'd been with already but I'm guessing four. All were working girls but that is what we wanted anyway. Two young guys overseas in a town with no limits. We were alive!
Back then there were no ladyboy bars that I can recall in the red light areas of Bangkok. If there were any, we didn't see them. I'd heard there were some transvestites that prowled on drunken foreigners and I told myself if I ever saw one I'd run the other way. This was before the internet and I'd never seen a transvestite in person or in pictures and didn't yet know what a ladyboy was. I was green and naive.
We had one night left in Bangkok and hadn't yet hit Nana Plaza hard so that was our target for the night. Three floors of bars, about 30 of them if I recall correctly; probably about 2,000 women to choose from. Maybe more as that time was more lively than it is today.
We found ourselves in a smokey dark bar on the bottom floor. I don't recall the name. I only know we went in there because my wingman liked the door girl and wanted to chat her up. He was busy with her and I was just relaxing while he worked his magic. He didn't waste time and was soon back in the short time room with the door girl. The only thing I remember about her is she had purple hair. It was probably a wig.
After he took his girl for a short time, I was left at the table by myself. It wasn't long before a girl came up and asked if she could sit with me. This lady was stunning with a gorgeous body, long hair, cocoa brown skin and almond shaped eyes. She had the shortest mini-skirt I'd ever seen and fantastic tits that were falling out of her halter. I invited her to sit.
She wasn't a dancer in the bar, she was a guest relations officer which is a fancy term for working girl. Just what I was looking for. I bought her a ladies drink and we started talking the normal chit chat stuff. Much to my surprise, she was actually pretty funny, spoke good English and enjoyable to talk with.
Some more drinks for both of us and soon she had her hands on my crotch. I was fondling her smooth legs. Soon she got up and excused herself to the bathroom. This was when the waitress came up to me and said "That not lady". I wasn't really sure what she meant. The waitress wasn't getting her point across so a guy sitting nearby, I think an Aussie, helped to translate. He told me the girl I was sitting with wasn't a girl but a bloke with a cock.
I was stunned & couldn't believe it. She was not my impression of what a transvestite was. I guess I figured they were guys in a dress with a 5 o'clock shadow.
When she returned, I asked her directly if she was a guy. Not my most sensitive moment. Much to my surprise, she said she was a ladyboy not a guy. This was the first time I'd ever heard the term. She asked if I wanted her to leave. It would have been easy to say yes but I was still stunned and now curious about this mysterious creature I'd stumbled upon. I told her to stay and ordered us more drinks. This got me a hug and hands back on my crotch. I was too embarrassed for this so I kind of pushed her off me. I said she could stay but I wasn't interested in that. But she had a ladies drink so she stayed. My life would have been very different had she left then.
I was shy others would see me sitting with a ladyboy but it was very dark in there so I thought I'd be ok. Liquid courage helped too. To settle my nerves I had a couple tequila shots. Finally I began to relax again. My friend finally came back to the table saying his short time turned into a long time and he was tired, drunk, broke and heading back to the hotel for sleep. He asked if I was staying and my new friend said "Yes he is. Don't worry he's in good hands".
Very cool I thought. My wingman gave me a high five and said goodnight. I was now on my own in Bangkok half drunk with a gorgeous ladyboy for the first time in my life.
With my friend gone, I was able to relax more. Social pressure back then especially in the military was overwhelming. Had he known she was a ladyboy I probably would have left with him, but he didn't know. Soon I let my guard down a bit and she was back to rubbing my crotch. I realized my cock was getting hard in the bar. I reached up under her dress and felt her hard cock in her panties. Now my heart was pounding a mile a minute. For the first time in my life I was stroking a cock other than my own.
I asked her if she wanted to come to my hotel with me & she said yes so I told her to go change and I'd pay the bar fine and my bill. The waitress looked like she'd eaten a lemon. She didn't approve but I didn't care. We left the bar and were back in my room in no time. It was a frenzy. Clothes flew off in all directions. Suddenly she was standing before me naked; this beautiful goddess with the most feminine body, gorgeous tits and a 5 inch hard cock. She guided me to the bed and I kissed her neck, shoulders and breasts. She moved my head down lower and I found myself sucking dick for the first time in my life. I didn't know how to do it but I tried doing like I'd prefer it; lots of lips & tongue & no teeth. I sucked her for awhile but she didn't cum. We switched positions and she started sucking me. Oh my god, it was fantastic and the best blowjob I'd had up to that time. I knew I wouldn't last much longer so I rolled her over and said I wanted to fuck her. She complied and showed me what to do. Luckily she had lube because I didn't. I did have condoms though which I made sure we used.
She lubed us up and guided me into her. At this point I didn't have much control and I cummed within a minute of being in her. I think this the first time I ever yelled out loud while having sex. The waves of sensation were staggering. Not just physical sensations, but mental as well. She actually cleaned me up a bit and I noticed she was still hard. This was when she scared me half to death. She told me now she wanted to fuck me. I didn't know what to do. She could tell I was nervous and told me not to worry that she would do everything and be gentle. She lubed us both up again, put me on my back, spread my legs and slowly, gently slid her cock in my ass. It hurt but it was a good hurt. An exciting hurt. My heart was racing again and much to my surprise my own cock got hard again. As she fucked me she started jerking me off. I'd neglected to do this for her when I was on top.
As I got more and more excited, so did she. Her pace on my cock and my ass quickened. I couldn't believe it but I was cumming again!!! When she saw me shoot my load she let go of my cock and hooked my legs over her shoulders. Now she was banging me hard. My knees were pinned back and hitting the head board of the bed. It hurt more but I was also experiencing only what I can describe as a mind orgasm.
I couldn't take much more though as she was fucking me now like a wild animal. Finally she cummed in my ass. I could feel her cock throbbing as she unleashed her juice in me. She gave a yell this time when she exploded.
We tumbled into each others arms smiling and laughing. I no longer felt any shame. I felt like I'd discovered something I was always meant to experience. There was no other person in the world I wanted to share my bed with that night. Only her. I drifted off into a semi-drunken blissful slumber with her massaging my back.
I woke up the next day and felt like I'd experienced an epiphany. My eyes were open now to this whole new world. We had another morning session of fucking and sucking. Then we took a shower together. I asked if she'd stay with me my last night in Bangkok and she said she would. I gave her some money for the night before and to pay her bar fine for my last night. She left and said she'd be back later. After she left I felt like an idiot as I gave her money for this day when I could have just went to the bar that night and paid it directly myself. I began to think she wouldn't return. I ate a room service lunch, watched some TV and snoozed. I began to write off the extra money I gave her when my phone rang. It was the front desk saying a Ms. Thongsook was downstairs and they were asking if she could come up. She had returned...My Angel.
We spent the next 24 hours doing everything you can imagine. Fucking, sucking, jerking each other, taking baths together, I even held her cock when she took a piss one time. After a few rounds I had to ask her to please not fuck me anymore as I was just too sore. She complied again and just jerked off on my chest. Around dinner time my hungover friend showed up at my room. I had her throw on her dress which was quite conservative compared to what she wears in the bar. She looked like a bank teller. My friend came in, saw her and gave me another high five. I told him I was staying in with her and he said "Good choice". Again, she fooled him and he had no idea she was a ladyboy but this time I wouldn't have cared if he did know.
That's the story of how I met my first ladyboy Thongsook. We kept in touch for awhile and I went back to see her again about 4 months later but we eventually lost touch. This was before email and neither of us was very good at writing snail mail. She changed my life and I'll never forget her.
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