Devin’s Ladyboy Dating 9

The first ladyboy I met this week was TM, a nicely shaped girl that likes playing the aggressor. It had been a few weeks since I made my original visit to her place and I was looking forward to another pleasing encounter with her.

I made my way over there in the afternoon and TM greeted me at the door with a smile. She was looking sexy in a tight pair of shorts and a tank top. She wasted no time in getting me into bed and we both took turns stripping off clothes. Just as she had done on the previous meeting, TM asked if she could go first. I agreed and was soon at her mercy. We were both enjoying ourselves so much that we ended up finishing before it was my turn. I will have to remember to go first the next time I see TM and hopefully that will be soon.

I have been trying to schedule a meeting with a new ladyboy for the past month and I thought we finally had things set this week. I arranged to meet DC around her area after she finished work, but my calls went unanswered as the meeting time came and went. I would have been more upset if it wasn’t for the fact that my young ladyboy friend JT had been texting me and asking if she could come over. I decided it was best to head home to wait for JT and postpone the meeting with DC until later.

I have written about JT a couple of times before. She is a very attractive young ladyboy with a wonderful pair of lips. She arrived at my place a little tipsy and I was happy for that since it made her much less shy than she normally is. JT got me down on the bed and began kissing me as soon as we got inside my room. That lasted for about 30 minutes until I was finally able to flip her over and take control. I do enjoy her kissing, but after just the first few minutes I was more than ready to take things further.

I knew that JT was strictly a bottom and is also a bit shy about being touched in certain places. This night was a bit different though thanks to the alcohol in her system. She was much more open to what I was doing and it made for a great experience. JT seemed to enjoy it, but she didn’t finish. I knew that meant she would be going after me again in the morning.

You may recall that JT always spends the night and has a habit of sleeping away half of the next day. It’s not the best situation for me to deal with, but for some reason I accept it. This time she stayed in bed for about 12 hours. I was busy getting work done when she finally decided it was time to get up. After a short trip to the bathroom, she was pulling me into bed again for a repeat performance. I guess it’s rather easy to see why JT gets to stay overnight at my place.

A few weeks ago I mentioned that my meeting with an old ladyboy friend was delayed by a rainstorm. Thankfully the rain held off this week and I was able to make the short trip over to see MM. I always go to her place and have probably been there close to ten times now. Our encounters usually follow the same pattern and this time was no different.

MM is a bit different than most of the other ladyboys I know. She belongs to a very wealthy family and spends a lot of time traveling around the world. She has also been able to pay for the best surgeons to work on her transformation. She is quite attractive and has a very feminine shape. Her face, voice and body are all very passable. She is post-op and has had more than one surgery on that area. I can say from experience that the latest operation has made her feel very natural down there.

I was happy to see MM again when she greeted me at the door. As always, we sat down on couch and she brought me some cold water to drink while we discussed what was going on in our lives. After a few minutes of chatting MM begins to kiss me and touch me and eventually places her plump lips on the more sensitive parts of my body. This is quickly followed by an invitation to join her in the bedroom.

We are soon in bed and MM will continue pleasing me orally while I admire her wonderful shape. The mood is always slightly affected when MM takes a short break to apply lubricant on herself, but I’m always ready for her when she emerges from the bathroom. She then positions herself on top of me and grinds out the motions that work best for her. I just lie back and enjoy the ride until MM finishes. She will then lie down on her stomach and let me go at her from behind until I’m done. It’s always a very pleasing time for the both of us.

I never made it to Pattaya this week, but I hope to get there soon. I will be traveling out of Bangkok for a short time and plan to meet some new ladyboys along the way. I will let you know all about it in my next article. Until then, please tell me what you think in the comments section below.

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4 Responses

  1. wwvs says:

    hey devin, i was just wondering if you could maybe tell us how you get to date all these beautiful ladyboys. i enjoy reading about your dates each week, but what i really want to know is how you do it. you must have plenty of tips you can give us.

    • Devin says:

      Thanks for the comment wwvs. And yes, you’re right. I have been thinking about making my ladyboy dating articles less about the actual dates and more about the advice I can share. I will try to do more of that in my future writing.

  2. mojarrad1989 says:

    Please write more