American Ladyboy In The Philippines

     When I was 14 years old my father was stationed in the Philippines. Although my mom had custody of me, she agreed to let my dad take me to the Philippines because, as she put it, "It will be a great learning experience for Stevie." Well, she had no idea just how much her little boy was about to learn!
We lived off base, and my dad was gone a lot on TDY - that's temporary duty - because he was a flight mechanic. So I had a lot of time to myself. I became friends with our maid Cresencia and spent most of my free time with her. My dad had a lot of girlfriends, and some of them left clothes at our house. One day I was bored and horny, so I tried on some panties and high heels. Then I applied some red lipstick. Mmmm, that always made me feel sooo sexy! I had been doing this since I was twelve - with my mom's things. I heard a noise behind me and turned around to see Cresencia in the doorway. Instead of getting mad at me she smiled and told me I made a pretty woman. I think she had an idea all along that I was kind of a sissy anyway. A few days later Cresencia introduced me to her cousin - Melinda - a beautician who did the make up for a lot of the bar girls who worked the clubs in Angeles City. But what interested me was the fact that she also did make up for the ladyboys too. Cresencia had told Melinda about me, so Melinda asked if she could make me up. I was thrilled. She asked me if I would like to accompany her to some of the ladyboy clubs and assist her with the makeup. That's where I met Roger.
Roger was the manager of Billie's, a ladyboy club. He was straight and really good looking - about 42 - but looked younger. He told me that I was gorgeous and that I could make a lot of money in the club. The next night I started my first shift as a night club hostess. Unlike in the U.S., the age of consent in the Philippines is much younger, so I was totally legal to work. The uniform in the club was high heels and string bikinis. When I first stepped out into the floor I was so self conscious, but the way men were looking at me soon made me feel sexy. Because I was pale skinned and very blond, I had a lot of african-american customers. Roger told me all I had to do was mingle with them, dance with them, and get them to buy me "Ladie's Drinks". I knew that the "girls" made their money by having sex with the customers, but Roger didn't push me to do that; I had told him that I had never had sex - never even kissed a guy yet. But this really cute black guy was really persistant. He started kissing me on the dance floor and feeling up my legs and ***. Kissing him got me really horny and I got hard. He kept whispering in my ear that he wanted - needed - a blow job and that he would give me 50 bucks, which is a lot more money than the filipinos got. So I told him to pay the floor manager for the booth, and to give me the 50. We went into the booth and he took his clothes off. He was SO sexy looking - all muscles and tattoos! I ******** out of my bikini, leaving just the high heels on, and squatted at his feet. His **** was the biggest thing I had ever seen - at least 10 inches and hard as a rock. I had never sucked anyone's **** before, but I had seen **** videos where girls were doing it. So I began tonguing and kissing around the head, finally engulfing it in my mouth. He shouted out and grabbed my hair and I felt my mouth flooding with warm *****. I was so surprised I didn't know what to do and I swallowed it all. He was so happy that he handed me another 20 before he left. He went back out to sit with his buddies, and when I got back out on the floor I had several of them approach me, all wanting the same thing. I made so much money that night! Roger was very proud of me.
That's how I became known as the American Ladyboy, and it was the beginning of almost 3 years as a ladyboy. I was very disappointed when my dad's tour was up and we had to leave the Philippines. They were so much more liberal in their views about homosexuality, prostitution, and everything.
finessebardot finessebardot
36-40, T
3 Responses Oct 1, 2011

They are much more accepting. I see lots of ladyboys there and nobody bothers them. And i dress very fem when I am there and it is very rare anyone says anything bad.

Yes, they are so much more accepting! I lived as a woman for 3 years, wearing short dresses, high heels, hair styled, make up - and I went shopping, dining - everything! No one cared - even if they found out that I was biologically a boy!

Even some stores there have the male staff wear skirts....

Loved your story honey, Wish it was me !!!

great story

Thanks sweetie, for liking my story. Kisses!

Hi, i am interested to apply at the bar where you used to work.. May i have the name of the bar or is it still operating?

Hi Eva! I worked at a club called "Mariposa", off of Field's Ave. on A. Santos St. It was 20 years ago, so I don't know if it's still operating. Good luck on your job search.