My First Encounter With A Lady Boy

Sun, 11/04/2012 - 13:18 -- Guest

I went to Thailand a few years back. I already have friends there who have been living there for a couple of years. Knowing them for a long time, I knew they would be there to give me a good time as it was my first time to go there. As we were celebrating one of my friends' birthdays, we knew that we should truly make the night memorable. After all, it is not everyday that we get to see each other.

The first step was to drink a lot. That was not a hard thing to do. We had beer bottles, vodka, tequila and almost all kinds of different drinks available to us for that night. We were staying in one hotel room that was often used for bachelor parties. It was big enough for all of us. There were even beds that we can sleep on or use if in case we want to bring in some ladies. Suddenly, there was a knock on the door. I volunteered to open it as I was the one nearest the door. As I opened the door, I saw a group of ladies eyeing me with interest. I immediately let them in as I looked at all of them with lust filled in my eyes. Looks like I will be bedding an exotic beauty this night.

I followed the ladies to where my friends were. They obviously knew them all. I wasn't asked to pick one girl, I was already given one. We all continued to drink, talk and even sing some karaoke. As time went by, I become more lusty. I couldn't keep my hands to myself. She just smelled so nice and her curvy figure was enough to make me want more. As she gave me a playful squeeze, I realized that was a signal that she wants something to happen tonight as well. We disappeared into one room and she asked me to only do her doggy style and from the back. I have never had anal sex before but I obviously wanted to do it. She allowed me to keep on kissing her and she even allowed me to continue fondling her breasts. I even convinced her to let me suck her nipples and lick them. I was so aroused that I nearly ripped her clothes off. Good thing she restrained me. She bent down in front of me as I immediately put the condom on my penis before I excitedly placed it inside of her.

She was so tight. I held on to her slender hips and slapped her behind as I came hard while she moaned. I was so drunk that night that I did not notice something wrong with what we were doing. I slept soundly that night. The next day, I was the butt of all jokes. I did not understand why. I only got why they were laughing at me as they told me the truth about the woman that I bedded the other night. She was not a she but rather a he. He was a transvestite and they were common in Thailand. I couldn't believe that I made love to a lady boy and enjoyed it. I was so embarrassed. I have nothing against gay people. I was just too straight to think about what happened. I only wanted to relieve myself without thinking about anything else. That experience taught me to become more cautious. I even told my friends to never speak of that night to anyone. Even up to this day, that remains a secret that only us know. It was a secret that we will never forget.