Devin’s Ladyboy Dating 8

I was hoping that my poor performance in the final encounter I wrote about last week was just a fluke. Unfortunately, those hopes were quickly dashed this week. I decided to meet a new ladyboy who looked very sexy in her photos, but the real thing turned out to be much less impressive.

I had only been chatting with JN for a short time and our conversations didn’t go all that well. I wanted to meet somewhere easy to have a talk and she thought I should take her to a movie. It’s a fairly common thing to happen actually. There are many girls out there who are just looking for guys to take them for dinner or a movie or both. I suppose it’s a similar thing to what I do, but at least I keep an open mind to the possibility of a relationship and I try to make it mutually beneficial.

Given our prior talk, I was surprised when JN messaged me in the morning and asked if I would come over to have some fun. I looked at her cute, white skinned, large breasted photos again and couldn’t say no. I got the directions and soon headed out the door.

When I arrived outside the building I sent an instant message and looked to see a girl walking towards me. She was smiling at me like she knew who I was, but I had no clue about her. It took me a second to realize that this was JN and then another to try and hide my disappointment. This was a short, plain looking, dark skinned ladyboy with not much of a figure. I guess I didn’t want to make it a wasted trip so I just went along with it and we were soon upstairs.

We sat down on the floor since it was a small room with no bed. I faced away from JN and occupied myself with television watching. I started to wonder if I had been tricked into meeting someone that wasn’t who they said they were. Either with fake photos or perhaps the real JN had given her phone to a horny friend and told her to ask me over. I had no desire to start anything, but JN soon began to massage me and take off my clothes. I really wasn’t into it and I think she could tell. I got up to take a shower and told JN to prepare whatever she needed to make this whole thing happen.

I showered off and made a decision to let the situation play itself out. When I came out of the bathroom I could see that JN did have implants, but they certainly didn’t look as nice as the ones in the photos. I had no trouble getting her excited and I wish I could say the same for myself. Obviously, I had chosen the wrong person to help me forget about my last poor performance. We played around until I got JN to finish and then I left as soon as I could.

I wasn’t that upset about my lack of excitement with JN. The whole scenario was not even remotely erotic. Still, I was anxious to meet the next ladyboy and put this string of less than successful encounters to an end. I decided to have the ladyboy named H come over and see me again. It had been a long time since we last met during Songkran weekend.

I picked her up from the BTS station again and we came straight back to my room. I had told her that I needed to go meet with friends that night and so she promised to make things quick. She wasted no time in getting my shorts off and I was soon reclining on the bed and enjoying her oral skills. I was doing my best to relax and clear my head of any negative thoughts. H was good, but she still needed extra time to get me going. I was starting to get worried.

I figured I better try something else and so I helped H get undressed and made her get on all fours while I moved behind her. I knew the site of that nice little butt would have to excite
me. Thank goodness I was right. I played with H and admired the view for quite some time. Her size was actually a lot bigger than I remembered. Eventually I couldn’t resist the temptation and took my place on top of H. Usually I would make sure not to finish first, but in this case I was more concerned with myself. I took care of business and H seemed satisfied. I promised to make up for my selfishness the next time and she is looking forward to that.

The next ladyboy I met was V, the very first girl I wrote about here on Dating-Ladyboys. We had been staying in touch since the last time we saw one another and we finally found a night to get together. I was hoping she still had her lovely white skin and cute backside. I picked her up out front and she looked ok. I remembered her being a bit better looking and assumed it was due to a lack of makeup this time around.

We came upstairs and V jumped in the shower. She came out wearing just her shirt and I could see those cute buns poking out from underneath it. I told her to lie down on the bed and I would give her a massage. I started to rub her down and quickly got her completely nude and myself as well. She did still have that cute butt and nice skin. I added some baby oil on her back and worked my way up and down her body.

Perhaps you can recall from my previous article that V is post-op. I spent some time observing the area in question and I was not very impressed. It certainly wasn’t the prettiest one I have seen and I already knew that it was not very deep. I played with her a bit and she did seem to get wet. I wasn’t quite sure where to go next and then V took her turn and started on me.

She gave a decent oral performance until I was more than ready to take the next step. I got behind V and admired how sexy she was from back there. I really wanted to try the other entry point because it looked perfectly tight and tempting, but I knew from previous experience that she didn’t go for that. I began to penetrate her and I was really surprised at just how shallow the surgery made her. I guess I must not have been able to see that easily the first time. I’m not underestimating when I say the depth was about 2 inches or 4.5 cm.

I was able to finish by a process of removing and inserting which was rather amusing to watch. It wasn’t clear if V enjoyed it or not, but she stayed the night and had her way with me in the morning. I’m not sure that I will be seeing V again even though she has been texting me a request every day since.

It was nice to get back into the groove this week. I’m hoping to make it down to Pattaya soon to meet a few ladyboys I have been in contact with there. Perhaps it will make for some interesting stories in my next article. Until then, feel free to add your comments below.