[Candyboy222]

Originally Posted by tim4lb

I will never forget the first time I had this happen.

Forgive my digression for some background history. I had only dated girls for the longest time and then finally experimented with a few transvestites and transexuals in Canada while mostly dating girls. After I moved to Asia, this continued as I had a series of monogamous relationships with genetic girls. Despite this, I had always found ladyboys sexy and intriguing. Eventually I started coming to Thailand for holidays and I began to almost exclusively date ladyboys. I had many wonderful relationships and encounters, but I never allowed a ladyboy to top me. I knew though that I really wanted to and eventually would.

I spent a week in Pattaya and met some lovely ladyboys - we had a great time. I needed a break and left for a week of relaxing on Koh Samet - a beautiful island nearby. I was walking down the beach the 2nd day there and saw a beautiful femboy bartender. I stopped for a couple of beers and flirted. Finally she told me she was a ladyman. I replied that I knew and that that was what I was looking for. We had a few drinks together after her shift and then returned to my room.

We kissed and caressed one another for quite some time and then proceeded to exchange oral including 69. We were both very hot by this time and she laid back, opened her legs and beckoned me to her. I entered her ... it was heavenly and tight. But I must have been nervous and more than a little drunk because I soon went soft. We tried a few more times but I couldn't maintain an erection, and she got a little angry and rolled over to sleep. I hugged her tight and instantly became hard.

She quickly surprised me by rolling on top of me, pushing my legs apart, and stroking her very hard cock as she moved to my ass. She lifted my legs onto her shoulders and pushed inside of me. I howled in pain and writhed to get her throbbing cock out of me. She spit into her hand, rubbed it onto her member and roughly pushed back inside my virgin ass. She went slow at first ... it was agonizing and yet I was loving every second of it. She finally got all of her very hard cock inside and then started to fuck me hard and fast. I felt like I was being ripped in two, but as I mentioned, it was so hot. Thankfully she didn't last long - I couldn't take much more - and she moaned as she unleashed a huge, thick load deep inside my ass. It felt really good and a little odd at the same time. Her hot cum leaked out of me for quite some time. The overall experience was probably the best I had ever had to that point.

We repeated the encounter each of the next few nights except she was in complete control. She would lie back and order me to pleasure her orally. Each night I would rim and suck her until she got too horny to take it and would ravish my ass. It still was excruciating, but I also felt magical. The encounter would end will her unloading her sweet cum deep in my ass, wiping off her cock and saying good-night

I went back to Samet looking for her, but she has moved on somewhere. Good luck to her and thanks for initiating me.

I have since been much more careful about using protection except my current long-term girlfriend who regularly creams my ass.

Wow! what a hot, hot experience I'm glad to read so many of you guys have found enjoyment in getting fucked by a ladyboy:D.