My Thai Ladyboy

There is a saying that 'when one door closes, another opens.' That was certainly true for me. My relationship with Jen (see my previous story: My First Ladyboy) continued for some time, but we rarely managed to see each other. I was mostly working in Africa and just couldn't get over to the Philippines very often. Eventually we drifted apart. Yet I was truly grateful to Jen for introducing me to a whole new world.

Eventually I started a new job that had me travelling to Thailand regularly. I was certainly happy about that, both because I was keen to explore a new place and because of the amazing trans ladyboys they have there. After my work was done during the day, I would explore the local cultural offerings and definitely stopped in a few ladyboy bars to enjoy the shows. Despite the temptation, I never bar fined any though as it wasn't my thing. I have nothing against working girls but always wanted more of a connection with anyone I was going to take to bed. Call me romantic...

I met Suri through another dating site and during one of my trips to Bangkok we made a date to go for dinner. I chose a very fancy and uncrowded Indian restaurant and arrived first. It was one of those warm Bangkok evenings and the place was all bamboo, low lighting and tropical greenery. Sipping a cold beer, I awaited my date.

Suri ended up being about a half an hour late, mostly due to traffic; which for anyone who has ever been to Bangkok knows can be pretty terrible, especially in the evening. She walked into the far end of the restaurant and I recognized her immediately. Stunningly beautiful, with long, dark hair and an olive complexion, she strode gracefully towards me. Slim, with long legs that went on forever, a very nice pair of breasts...implants obviously but quite natural looking, and narrow hips that made me want to ask her to spin around for me immediately so I could gaze on what was I am sure, and amazing ass. She wore tight jeans and a white crop top that showed off her flat, smooth abdomen. I was definitely a lucky man and every eye in the place was on her. I stood and got a warm kiss and hug before we sat down for dinner.

It was great to meet her and while her English wasn't perfect, it was better than most Thai's. We talked about our lives and our experiences dating. Like most trans girls I speak with, they often wonder why a very straight, alpha male is so interested in them. Suri seemed very comfortable and laid back. We both felt relaxed and I could tell immediately there was chemistry here.

After dinner, we walked out to the street and called a taxi. While we waited, Suri put her arm through mine and stayed glued to my side. We just chatted about nothing and as the taxi pulled up she swung around, wrapped her arms around my neck and planted a deep, warm kiss on my lips. She ground her hips hard into mine, seeming to search for an erect cock and within seconds she found it, as I had an instant hard on. She leaned back a bit and gave me a wicked smile. I think she was quite proud of how turned she was making me.

We got in the taxi and headed towards my hotel. I had made it clear I didn't expect anything on our first date and fully intended to get out at my hotel, pay the driver and have it take her home. Despite a desperate urge to get her in my bed, I was doing my best to be a gentleman. Suri had other ideas though...maybe because I was being a gentleman and not pawing her or being crude. At the hotel she climbed out with me and walked, arm possessively through mine, across the lobby to the elevators.

Soon we were in my room, which was a small suite with lots of space. We dropped down on a sofa at the base of the bed and chatted a bit. I told her again I didn't expect anything and she just smiled and climbed onto my lap. My arms went around her and I soon discovered how much she liked kissing. Our tongues intertwined and she held on to me tightly and my hands began to wander over her slim, lithe frame.

After a while she crawled off my lap and grabbed my rock-hard cock in my jeans.

"It's big?" she asked, eyes on my bulge.

"Find out," I replied teasingly.

Suri worked quickly to open my jeans and pull my erect member free from the confines of my pants. Her eyes lit up as she wrapped her hands around my cock. I couldn't help smiling. She slid her fingers gently over the tip, damp with precum and along the shaft admiring her prize.

Taking charge, I stood up and pulled her to me for another long kiss before pulling off her little crop top revealing a lacy bra. Soon her jeans were off and she knelt in front of me to pull mine down, along with my underwear. Soon I was naked and she wrapped her hands around my cock once more and began giving me a slow, loving blowjob. I watched her little head bob back and forth as she worked her lips over the head while cupping and gently massaging my balls.

After a few minutes, I pulled her up and lifted her up to carry her to the bed. Laying her down I took in her beautiful light brown skin, big, dark eyes and shiny black hair spread across the pillow. She was femininity and beauty defined. Damn, I am a lucky man!

Unlike my previous experience with Jen, Suri was not all shy about her little girl cock, which was also rock hard and peeking out of her little panties. She saw me looking and lowered a hand to gently stroke it through the thin material. I knew I shouldn't, but seeing her do that made my erection almost painfully hard and I could feel lust driving out any other thoughts in my head. I watched transfixed as she stroked herself and began moaning just a little as I stared.

Not able to wait any longer, I lay down beside her and pulled her to me. We kissed again as I slowly worked her panties down her long legs. We broke our kiss only long enough for her to pull them the last way off her feet and then remove her bra, revealing two beautiful, small breasts. I pushed her back and began lavishing kisses on her breasts and nibbling at the small nipples. She stroked the back of my head as I did and gasped when I nipped a little bit at one of the sensitive nubs. Her other hand continued to stroke her cock, and without thinking my hand joined hers. She let me take hold of it and then guided my hand in a gentle motion jerking her off. I could feel precum leaking over my fingers and found it hugely erotic.

Not wanting to wait any longer and desperate to take this amazingly sexy woman, I climbed up in front of her and spread her legs. Suri knew what I wanted and reached for a small satchet of lube she had in her purse on the nightstand. Tearing it open she squeezed some of the lube onto her fingers and the rest onto my cock as I knelt between her outspread legs. Working it over the length, she the reached down to rub some on her little rosebud. Nodding when she was ready, I took hold of my cock and slid down enough to line up on her special little spot.

It took a bit of prodding but we both wanted it so badly that with a determined 'pop' I slid past her outer ring. She gasped a little as it went in and bit her lip in concentration. I stayed very still as she tried to adjust to the large intrusion into her special place. Her hand slid down to her own cock, still engorged, and began to stroke it again as she slowly relaxed. Taking it slowly, I began small movements in and out across her sphincter and could feel the amazing tightness with each thrust.

I have been lucky enough to have had quite a few partners who were into anal sex. My ex-wife and I did that more than anything else and since my divorce I have had a couple of great lovers who shared my preferred kink. But there is just something different about being in a ladyboy's ass. Maybe it is tighter somehow. Maybe sliding past the prostrate gives a different sensation...but whatever it is it just feels different. Perhaps it is just that this is, in a way, another taboo that gives it an extra flavour of excitement. Whatever the magic is though, it definitely works on me. Watching Suri below me as she began taking more and more of my cock was the sexiest thing I could imagine.

Suri was not making much noise...her eyes were tightly closed, and she made little whimpering sounds with each inward stroke. Her hand continued to pump her cock and her heels were digging into the backs of my thighs, pulling me in even closer. After a few minutes, she was taking my whole cock inside that wonderful, tight, amazing ass. The world could have been ending around me at that moment and I wouldn't have noticed.

Reaching forward I pulled her up with me and rolled back into a sitting position. She wrapped her arms around my neck and held on as she found herself sitting in my lap, my cock buried as far as it could go in her ass. She paused to adjust to the new feeling and then kissed me passionately, starting to bounce up and down on me. Her little cock was now sliding up and down against by stomach which I found a unique feeling and quite a turn on.

Suri continued to ride me in that position until I eventually lifted her up and placed her gently down on her tummy...my favourite position. Pinning her legs between mine I lined back up on that gorgeous ass with its relaxed, peeping hole and plunged back in. Now, the dominant in me took over and I pounded Suri's little backside. Her whimpers turned to grunts as her hips were driven into the bed with each thrust. In only a few minutes I felt the wave coming and with one final deep lunge began to spasm as I came as deep inside her as I could reach.

Panting, but holding on to her hips, I pulled her onto our sides. Her back was still to me and my cock still buried in her ass. Reaching around, I grabbed her cock and began pumping. Suri's hand closed over mine guiding my strokes while she turned her lips to meet mine. Her grunts came faster and faster until at last her little girl cock began jetting a hot stream of cum onto the mattress. Shuddering, she collapsed down onto the bed.

We stayed that way a while, with my cock buried inside her and my hand lazily massaging her softened cock and tiny balls. I looked at her as she lay there panting and slowly coming down from her sexual high. We fell asleep that way and for my part I was truly satisfied.

Later that night, Suri pulled away from me and trotted to the bathroom. Coming back a few minutes later, she snuggled right back into the same position with her ass pressed up against my now soft member. I thought she was going back to sleep but she began gently massaging my cock with her ass and in no time at all I was rock hard once more. Reaching behind her, she grasped my cock and lined it up with her little hole. I looked quickly around for another satchet of lube, but Suri wasn't paying any attention. She forced her ass back against me until I slide past her sphincter and into her ass once more. For the next ten minutes or so, she just gently fucked herself on my cock. I stayed still and just ran my hands over her smooth skin, cupped and massaged her small breasts and just enjoyed the sensations of being back inside my beauty. Her hands began to pump her cock again and within a short few minutes she came once more. Murmuring satisfaction she relaxed to go back to sleep, but I was having none of that. Grabbing her hips, I began to thrust gently into her and in no time pumped a second load of cum into that perfect little place.

Suri and I continued to see each other for another year or so, but eventually she let me know that she was going to start seeing a European guy who was living in Bangkok, rather than waiting months between my visits. I had no hold on her and wished her well. I still miss Suri and our times together. Not just the sex, as we had lots of other good times. But the sex was definitely something to remember always.