Devin’s Ladyboy Dating 1

Admin note: Devin originally wrote this in early April, 2012.

It’s been a good first week back here in Bangkok. I have finally gotten my sleep schedule adjusted so I can live like a normal person again. I’ve had some interesting ladyboy encounters that I would like to share with you. Perhaps I will make this a regular weekly ladyboy dating report.

The first night was a little tricky with the scheduling, but I managed to meet 2 new girls. The first ladyboy (I will call her V) had just made contact with me that very day on a dating site. Her profile was written in a way that made me believe she was a well educated girl that had traveled extensively. It also gave the impression that she would be a fun date and easy to talk to. We decided to meet along Sukhumvit Soi 11 and find a good place to eat.

I have had plenty of experience scheduling multiple dates on the same night so I was trying to set something up with the another ladyboy (I will call her M) that would allow me a little extra time in case things ran late with the first girl. It wasn’t too difficult though as M said she would be around the area of my hotel that evening and I could let her know when I was ready to meet.

I stepped into a little café near BedSupperClub at the arranged meeting time with V. I was about to call her when a girl looking similar to her photos walked by on her way to the washroom and gave me a glance. I was hoping it was her as she was pretty cute and had a nice shape. My hopes were confirmed when she answered my call and said she thought she may have just passed me by and would be right out to say hello. We greeted each other and decided to head across the street for a bit of Thai food at an outdoor restaurant.

It was a nice conversation and she told me about her schooling in Europe and her business in Bangkok. I was impressed with her maturity and really liked her smooth white skin. She was in her late 20’s, petite, medium height and certainly had not had breast surgery. We were going along just fine, but I was starting to get messages and calls from M by the time we were done eating. Lesson 1 – put your phone on vibrate and learn how to sneak a look at it without your date knowing what is going on. V suggested we go for drinks and I could tell that drinks would probably lead to something else, but I already had M waiting for me and I knew that same “something else” was almost a certainty with her.

I managed to convince V that I was really tired from my trip and we should go for drinks another time. She didn’t want to accept that at first, but I was actually pretty tired by that time and she could see it in my face. She offered to give me a ride back to my hotel and I begrudgingly accepted because I knew M would be waiting nearby. Some quick thinking led me to message M while V used the washroom and to tell her to wait by the MRT station for me so we could walk to my hotel together.

I should note that V having a car is not a normal situation. It is a clear indication that V is in a higher economic class than your average ladyboy and I was already convinced of that based on our dinner conversation. I personally don’t discriminate against ladyboys from lower economic classes, but it is something to be aware of.

I got a bit lucky on the ride back as V didn’t want to get lost. I said she should just turn around by the MRT station and head back in the same direction. I knew it would save me a bit of walking and I wasn’t worried that M would be waiting by that particular exit. I got a nice hug in the car and V mentioned that I wore her favorite cologne. I could tell she wanted to kiss me (which was confirmed by her text message later) and I knew it wouldn’t be long before I would see her again.

I’m watching V drive away as I’m answering the latest call from M. She had been calling for awhile so I hoped she wouldn’t be upset. She seemed fine and I noticed her walking across the road by the other exit. We met along the street and she looked pretty good. Like V, she was flat chested, but she was tall and slim and had a decent face. We said hello and headed straight to my hotel as we had agreed upon earlier.

I met M on MTL a week earlier and we had chatted for a bit. She knew I had just arrived back in Bangkok and had promised me a good massage to help me recover from all the travel. I took a quick shower before making my way to the bed where I got on my stomach with the towel still around me. It wasn’t long before I realized that M actually had some massage skills. A welcome surprise because I really needed a good massage at that point.

As expected, the towel soon came off and the baby oil started being rubbed around special areas. As you can imagine (and I will let you imagine) things progressed beyond the massage and we had quite a good time. M was larger than average and very strong, as you would expect from a 22 year old not taking hormones. She was also perfectly happy being both a top and a bottom.

M spent the night and in the morning we repeated the prior evenings performance before she graciously departed and headed home. It was a very satisfying first encounter and I knew it wouldn’t be long until we would be enjoying each others company again. I have to admit, it was a hell of a first night back in Bangkok.

The second night was pretty damn good too. As I predicted, V was very much determined to see me as soon as I had the time. I spent the day getting organized and settled into a new apartment and then messaged V to let her know that I could meet up for a late dinner. She suggested we meet near my apartment and we could walk to a place from there. That sounded perfect to me and I had a pretty good idea she would be happily visiting my room after dinner.

We ended up at a quiet café just around the corner from my place. The conversation was nice and she talked about the long hours she had been putting in at work. I mentioned that she should go for a massage to help her get rid of the stress she was feeling. She agreed and then suggested that maybe I could work some magic on her neck and shoulders. I thought it was a great suggestion, especially since I still had a nearly full bottle of baby oil in my room!

We made our way back to my room and V wasn’t shy about taking her top down so I could get my hands on her tight shoulders. I worked my fingers around her back and she was loving my technique. I was enjoying myself too as I rubbed the oil into her smooth white skin. After 10 minutes or so she volunteered to return the favor and of course I accepted the offer.

I stripped down to my underwear and she proceeded to give me a nice rubdown. I told her to remove the undies if they were getting in the way and she quickly got me naked. V gave a decent massage, but not nearly as good as the one M had given me the night before.

After she finished making her way down my body, I thanked her and told her it wasn’t fair that she got to see my naked body while I hadn’t yet seen hers. V didn’t protest and so I helped her take down her skirt and panties. Surprise! V was post-op! Inside my head I was feeling a bit of shock, but I didn’t let it show. It was quite unexpected since she had never mentioned it and I had never asked. Usually a girl who has had surgery will put that in her profile or at least refer to it in some conversation.

I have been with post-op girls before and it certainly was not a turn off for me at the time. We continued to explore each others body and I ended our evening together being very satisfied. One issue with V, and this is fairly common in my experience, was that her surgery left her with very little depth inside. It felt ok, but there just wasn’t much room for penetration.

Another common issue with V and other post-op girls is that they are no longer interested in having anal sex. This fact was confirmed in some messages we exchanged the next day after V requested an additional massage session. She is a nice girl and I might get with her again one day, but for now I have other ladyboys that I would rather be spending time with.

The next night I met a girl (I will call her X) that I had been chatting online with for a couple of months. I was really excited to meet X after getting to know her a bit and staring at her very attractive photos for weeks. She made it quite clear that she was a no-nonsense woman that was educated, well-traveled and had a great job. Her photos made her look like a supermodel with an amazing shape and I couldn’t wait to see that body in person.

We decided to meet at a coffee shop in my area and then find a place for dinner. X ended up being about 30 minutes late, but was looking good in a very nice dress when she finally arrived. The only problem was that my expectations were really high and her appearance was not nearly as good as the pics I had been staring at for so long. Her smile was perfect in the photos, but her teeth were actually not that great. She certainly did have large breasts, but her figure wasn’t as ladylike as I had hoped for. So much for the perfect image I had in my head all those weeks.

We made a quick exit and sat down at a nearby Thai restaurant. X was very well-spoken and we discussed her work and travels around the world. It became obvious that she was part of the hi-so crowd (the more wealthy Thai people living the good life) and didn’t hang around the same places that I do. She spoke of the difficulty she has meeting decent guys and the fact that she has never befriended another ladyboy. I think she wanted me to be impressed with her independence, but every time she opened her mouth all I saw was her less than perfect teeth.

We talked a long time and X suggested we find a nice place to get some dessert and a drink. For some strange reason we had trouble finding a café that was open past 10 pm. We walked all over and finally located a place where we ended up sharing some cake and more conversation. It wasn’t long before I was ready to head home and I was surprised when X said she would walk back with me. I wasn’t sure what to think, but I figured I would just go with it and see what happens.

Keeping in mind that X considers herself part of a higher class of people, I was curious to see what she would say about the complex I stay in. It’s actually a decent apartment and not all that cheap, but I figured it might not be up to her standards. As we approached my building I pointed and sort of sarcastically said that that’s where I live. I could tell by her reaction that she assumed I was joking and then she made followed with a comment about the place being less than impressive. I can’t say I was shocked by her reaction and I played it off as a joke. Luckily for me there is a nicer place just a few doors down and I used that as my fallback.

X seemed satisfied with this nicer place I was now falsely referring to. Awkward moments passed as we stood there across the street admiring my new apartment building. I tried to make small talk, but I could tell that X was expecting an invitation to see my room. I was stuck! I would have loved to have gotten her alone in my room, but how could I go back to the other building now. I had to play it off and pretend like I wasn’t interested in getting her upstairs. Thankfully she didn’t press it further and I was soon waving down a taxi for her. We parted with a kiss and that’s probably all I will get until I figure out a way to rent a room down the street for a night.

The next evening was reserved for A, a ladyboy I have spent time with before. A is in her mid 20’s with a cute face, but she is a bit on the chubby side. She used to stop by my place in the evenings after her work and would give me a massage that always ended happily. A keeps in touch with me online and she was anxious to see me again. She came right to my room and I was soon face down on the bed ready for my rubdown. It wasn’t long before I noticed how inadequate her massage was compared to the one I got from M. It must have only been a few minutes before she totally abandoned the massage and was moving on to other things.

I know I shouldn’t complain about a girl wanting to get right to it, but I was kind of looking forward to a nice, relaxing, sensuous massage. Instead of that I got a few rubs and then some uncomfortable probing. I was totally turned-off by it and A didn’t know what to make of it. We played around for awhile, but I was tuned out and eventually A had to satisfy herself in the shower. I don’t think I will be seeing A again anytime soon.

The following day I was feeling like I needed to make up for the prior nights performance and so I invited M to come over and lay her magic hands on me. There really isn’t much different to report from my first meeting with M. She gave me a nice massage and then we had some fun afterwards. I’m fortunate to have someone like M to call on.

I was actually looking forward to spending that evening alone, but somehow I ended up meeting a new girl I will call AK. I was just checking the girls on MTL in the evening when I got a message from AK, a cute young ladyboy in her early 20’s. We exchanged a few details and discovered she was staying at a friends house just around the corner from my place. We shared webcams and she said the she wanted to come over to my room. As always, I had to make sure that she was looking to have fun and not to make some money. I wasn’t convinced by her answers and so I didn’t go down to the local 7/11 when she said she would be there.

I figured that was the end of that and a little while later I left my room and headed out for a walk. I exited my street and started up the main road when a girl passed by that looked awfully similar to AK. I actually thought it was a cute young lady at first glance and was going to be very impressed if that was really AK. I thought for a second and then remembered that she had given me her number. I quickly called it and watched to see what happened. Sure enough, that cute young girl stopped, reached into her purse and answered my call.

She had no idea where I was calling from so I decided to have a little fun with her. I told her to walk down my street and I would be waiting for her by the 7/11. We kept chatting as she walked and I followed behind to get a better look at her cute little butt. She finally caught on to my spy game and stopped to wait for me. We said our hellos and then headed up to my room.

AK didn’t waste any time once we got inside. She started grabbing me and stripping me down before I even got to the bed. She had an attractive face and a very sexy little body. She was flat chested, but her tight little behind more than made up for that. AK let me know that she was a bottom girl and that was perfectly fine. I think I ended up enjoying myself way more than she did which was odd since she was so eager to get things started.

AK got her things together quickly and I was ready to show here the door when she asked something I was hoping she wouldn’t. I think she phrased it as money for food. Usually it’s money for taxi, but she could hardly do that considering the fact that she was staying just around the corner. Normally I give a girl a fair amount of money for transportation when they make the effort to come to my place and I know they aren’t trying to make a business out of it. For some reason I just didn’t like how AK went about it, but I can’t say I was surprised. I resisted on principle and she put up a small protest that we settled by agreeing to go for dinner next time she was in my area.

It certainly was a very busy first week back in Bangkok. I managed to meet four new ladyboys and one former partner. It’s normally not this crazy and I’ll be happy when I get some free nights to spend out on the town. It’s actually half way through week two for me here in Bangkok as I finish this report and I will be meeting with the first ladyboy since AK tonight. Hopefully I will have plenty more good dating stories for you in my next report. Until then, feel free to add your comments below.