Devin’s Ladyboy Dating 4

Admin note: Devin originally wrote this in mid May, 2012.

I’m back in Thailand now after a few weeks of travel. I was actually planning to spend more time away from the Bangkok heat, but I was getting bored without any ladyboys to keep me company. I suppose that statement sounds awfully similar to what I wrote in my “All About Devin” article.

I had been chatting with a few new girls before I left town and also kept in touch with them as I was traveling. I was the most anxious to meet a tall, slim, white skinned ladyboy I will call CT. I had a little trouble scheduling a meeting once I got back due to the fact that I have been spending a lot of time dating with a very cute Thai lady. I managed to keep one evening open and invited CT over to my place.

I was really excited to meet CT as we had shared webcams a few times and she was quite attractive. She made her way over to my part of town and was waiting across the street from my building when I walked out the front door. I waved to her and she came strolling across to give me a nice little hug. I could feel that she had a very slim waste and her medically enhanced chest was looking very sexy. She was quite tall and her face was very smooth and pretty. We headed up to my room to get further acquainted.

We sat down on my couch and talked a bit about her work and my travels. CT mentioned that she liked my height and wanted to see how tall she was next to me without her high heels on. We both stood up and she moved close to me in order to get a good comparison. I seized the opportunity and put my hands on her hips while pulling her closer. CT was a bit shy at first, but she soon warmed up and proved to be a great kisser. She slipped her hands inside my shirt and was enjoying the feel of my body which led me to suggest that a full body massage might be even better.

I had asked CT about her massage skills previously and she said she would be happy to try her best to soothe my travel weary neck and shoulders. I had the baby oil all ready to go and CT was in full agreement that I should remove all clothes before she started. It was actually a very poor rubdown, but it quickly turned into much more than just a massage when she using her tongue instead of her hands.

CT got undressed and I took a minute to admire her body. She looked even better naked and had a very feminine shape. We must have kissed and touched each other for 5 minutes before I decided it was time to take things further. CT preferred to be on bottom so I took control and we ended up finishing together. We both had a fantastic time that night and I knew I would be seeing CT again very soon.

Ladyboy M was the next girl I met. As you may recall, I had seen M a few times in the weeks before I went on my trip. I had gotten a little bored with her back then, but I really wanted one of her thorough massages again. She was happy to come over and I enjoyed her hands on me and all that followed.

A return engagement with CT was next. She had been asking me to get together again, but I was reluctant to do so because she was asking me to reimburse her for taxi fare. While I have no issue with paying for a girls transportation, I do have a problem when they ask for an amount that I know is way too much. I just don’t want it to become a money making activity for anyone. We eventually agreed on a fair amount and had another wonderful time together.

My most recent meeting was with a new ladyboy I will call BS, an appropriate name given what transpired. I had messaged with BS a few times online and her answers were always very short. I figured her English skills were not very good and it could be difficult to communicate with her. She was also very young and might not have much dating experience. I probably should have waited longer to meet her, but she messaged me on a night that I was going to be home alone and so I decided I would give it a shot.

She arrived at my place and looked good. Maybe not as good as her pics, but she still had a decent figure and face. Her understanding of English was much better than I expected and after a brief talk we decided to head up to my room.
I spent about 10 minutes asking BS about her life here in Bangkok. I was satisfied with her answers that she was just a young, single ladyboy working in a salon that wanted to have some fun. I proceeded to get the fun times started and BS went along for the ride. She seemed shy and not quite sure of herself, which resulted in a less than great experience for both of us. I knew there wouldn’t be another meeting with this young ladyboy, but I tried to appear satisfied.

BS soon got dressed and was preparing to leave while I was retrieving the proper amount of money of money to give her for the taxi. I had no sooner taken the money out when BS walked up to me with her hand out and simply said “five thousand.” I was a bit shocked at that point and I don’t even remember what my first reply was. I had 200 baht in my hand that I was going to give her and I was already kicking myself for not learning more about BS before I met her. Not that this same situation couldn’t have happened anyway, but it might have been prevented had I taken the time to question her more.

I eventually got BS to back away and listen to me. I tried to explain that this wasn’t about business and I was happy to give her money for the cab but nothing more. Suddenly, as so often happens here in Thailand, her comprehension of the English language became very poor. She had no idea what I was talking about and could now only pronounce the two English words “five” and “thousand.” I’m trying to make this comical now, but at the time I was just trying to diffuse the situation as best I could.

After a few minutes of calmly talking the subject over, BS reluctantly made her way out of my room with 200 baht in hand and I was able to laugh about my poor judgment. Apparently I needed to learn this lesson more than once and hopefully this will be the last time.

It’s good to be back in Thailand again. I hope to travel around the country soon and meet some new girls outside of Bangkok. Until next time, please feel free to comment below.