My First Ladyboy Date

So how does a guy end up deciding to date a ladyboy? And what is it like on that first date? I’m sure the answers to those questions are slightly different for all of us. The following account is how it happened for me.

My very first memory I have of a ladyboy is from a pornography website. Yes, not the proudest thing to admit. I’m not sure how I ended up on a site with that type of material because I certainly wasn’t searching for it at that point of my life. I can remember noticing a photo a slim, brown skinned figure lying on their side with a large piece of equipment poking back between the legs. I took a closer look and I immediately found myself very attracted.

I stared at the photo for quite awhile and tried to sort through my thoughts. The form of the body was exactly the shape I like and the extra part only seemed to make it more exciting for me. What the hell was going on? I decided it was just a strange moment of weakness and went back to surfing other websites.

As you can imagine, the image of that ladyboy stuck in my head. A few days later I decided to test myself and started to search online for photos of naked men and gay porn. To my relief I had absolutely no reaction whatsoever to this material. Perhaps I was right and the prior moment of attraction was just a fluke. It was time for life to return to normal, or so I thought.

I suppose it was about a week after that when I had the urge to see that photo again. It took awhile, but I finally managed to find my way back to the same website. And there she was, looking just as desirable as she did before. This time I decided to investigate a little further and what I discovered quickly changed my life.

I was fascinated by what I saw, so many sexy ladyboys. I clicked and clicked and my eyes opened wider and wider. Where was this feeling coming from and why had I not noticed it until I was 32 years old? I suppose there was no way to stop it now. I couldn’t possibly deny that I was attracted to this type of woman. The only question now was what to do about it.

I continued to feed my ladyboy desires with internet pornography for a few months, but I knew that eventually I would need to take the next step. I ended up finding a local dating website that had exactly what I was looking for. I created my profile and started contacting ladies that fit my preferences. I was strictly attracted to slim and feminine types.

It wasn’t long before I made a connection with a nice looking transgender woman. To be honest, I still can’t say if she was truly a ladyboy or just a crossdresser. At the time, I’m not sure I really knew the difference. After exchanging a few emails we decided to set a meeting. The time had finally come to put my new found attraction to the test.

I can remember being very excited and nervous as I waited at the agreed upon location outside of a coffee shop. I was busy scanning the area for anyone that might be her. The meeting time came and went and my hopes faded. This was back in the day when not everyone had a mobile phone so I had no way to instantly get in touch with her. I eventually headed home and considered that perhaps this whole thing wasn’t meant to be.

I sent a message online asking what had happened and she replied with a similar question. She thought we had somehow missed each other, but I still think she got cold feet. No matter what the cause, we agreed to meet again the next night and I made sure to describe the vehicle I would be in so she could come and find me. I didn’t want to look like a fool waiting around for her like I did the previous night.

I was just as excited the second time around as I waited in a parking lot near the coffee shop. I saw someone that fit the description and they began walking my way. Sure enough, it was her and we said our hellos. She looked cute, slim and feminine enough for my taste. We talked a bit and then went inside to get some hot chocolate. The café was busy and the seating was limited so we decided to head down to a local beach for a walk under the stars.

We continued to talk during the short drive and again as we walked along the water. It was a warm summer evening and the moon was shining above. The beach was quite large and had plenty of little hiding places where the lights didn’t reach. I was delighted when she asked me if I wanted to find a dark spot to get better acquainted. We searched around until we found a place that was secluded enough for us to feel safe.

I remember that I had no idea what to do and was hoping that she might be able to lead me through it. Before long she had managed to get both of our pants down and directed me to kneel in the sand. I don’t want to make this too graphic, but by some sort of magical yoga move she bent over at the waist and got busy on me with her mouth while positioning her equipment directly in front of my face. There I was for the first time ever staring at a nice little package as it dangled in front of my mouth. What the hell do I do now?

I kneeled there for awhile trying to figure out where to begin. My date was doing such a good job on the other end that, before I got beyond some simple touching on my end, I quickly finished. I guess I was distracted by what was in front of my face and had forgotten to control myself. An awkward moment passed before I got to my feet and put my pants on. There was still a slight worry about being caught so I suggested we head back to my vehicle.

While we were walking back I began to think about what I should do next. I was happy and completely satisfied with what happened, but I felt like there was something more I needed to do. When we were safely inside my vehicle I sat there for a moment and tried to put together the words. I honestly wanted to make my date happy, but I really didn’t know how. As I recall, there was a long silence and then I simply said thank you before starting the engine and driving her back to the coffee shop.

Although I never got the chance to see that girl again, I will always be grateful for the experience we shared that night. I’m sure it wasn’t the most satisfying date for her, but it was the beginning of a new life for me. There were some awkward moments which I can look back on and laugh about now. I suppose that’s to be expected whenever you’re doing something for the first time. I did ponder the meaning of it all for several days afterwards and I plan to write another article here to address that issue as well.

So that’s my account of my first ladyboy date. It certainly was a memorable one with the romantic walk along the beach, some nice conversation and then a bit of naughty behavior. I was just happy that I had finally taken the next step and acted on my new found attraction. How about your first ladyboy date? Please feel free to share your first ladyboy date stories with us as we would love to hear them.