Written by rorty88
31 Mar 2016
First Time With A Ladyboy
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This is what happened on my second trip to Thailand in 2013.
I landed in Bangkok at midday and got a taxi straight to Pattaya. Instead of staying in the city of Sin itself, I like to stay in Jomtien, a small seaside town about 10 minutes up the road from Pattaya. I had an apartment booked so I checked in and headed down to the local beer bars to take the edge off the jet lag. I sunk a couple of Heinekens and trotted back to my room with the sun still out, falling asleep instantly.
I woke up around 2am and despite trying to get back to sleep, I was wide awake. I walked out of my apartment complex and grabbed a baht bus into Pattaya. It costs 20 baht (40 pence) to get to Walking Street, which is fantastic value and they also run 24 hours a day). I couldn’t be bothered with the mayhem of a club, I just wanted somewhere to unwind before heading back to bed. I walked down Beach Road away from Walking Street and found a bar outside just off the seafront which was closing. There were two girls working there, both packing away and cleaning down. I asked if they were still serving and one of the girls grabbed me a Heineken as I pulled a stool off the bar and sat down. I sunk the first bottle in one hit, the journey from Jomtien had made me thirsty. She served me up another.
I was so tired and disorientated that I collapsed my head on the bar and almost went back to sleep. I rested for a few minutes before lifting my head up to see the bar girl looking at me. Without breaking the conversation down, she asked why I was tired, where I was from etc. The other bar girl left and the one who served me took the seat next to me. She reached her hand into my lap, rubbed on my dick and asked if she could come home with me. I mumbled agreement, too tired to argue really and the thought of going home alone and not being able to sleep wasn’t sitting pretty. We walked back to the edge of Walking Street and caught a baht bus back to Jomtien. I wasn’t really paying attention so we missed the stop close to my apartment.
We stayed on the bus and got off on the beach front, meaning we had to walk back up one of the Soi’s (Thai for street) to get to the apartment. It was about 4am at this point and the Soi was pitch black and deserted. There were a few stray dogs roaming but after a glance in our direction they went back to sleep. About halfway up the street the girl took me by the hand off the road and down a secluded alleyway. Being disorientated in a foreign country with a total stranger I assumed the worst and the fight or flight response kicked in with a huge adrenaline rush. She pushed me against the wall, pulled down my shorts and took my dick in her mouth. She sucked it like a pro, making me buckle at the knees. Not wanting to waste my load on a blowjob, I pulled her up, kissed her deep, did up my shorts and set off once more to my apartment, a little bit quicker this time!
After getting to my complex, we get in the lift up to my apartment on the fifth floor. At this point, the fairly innocent walk back to my room broke out into a full on make out session. We could not get our hands off each other in the lift and we pushed each other into my room. We took each other’s clothes off and with me standing their naked, she had just her knickers left on. She fell onto all fours and took me in her mouth but I was done being satisfied, now it was her turn. I flipped her over onto her back and pulled myself on top of her. Then I grabbed her panties and begun to pull them down. She grabbed my hands and said stop. I asked her why, I wasn’t sure if she didn’t want to all of a sudden. She whispered in my ear that she was a ladyboy. My brain didn’t even react. I just pulled her panties straight off and took her dick in my mouth. This was the first time I had ever even touched someone else’s penis, let alone sucked on one. It felt so smooth and foreign in my mouth. She pulled me up and faced me, asking if I was gay. I said I wasn’t, she was just a lady to me and she flipped into the 69 position. We were both going silly on each other until she reached over, pulled out a condom, stuck it on me and decided to ride me. Her hole felt so small and tight but it slipped in without much struggle. I fucked her fast and hard for what was only a few minutes at best before being ready to cum. As I got close I pushed her onto her back, sat on her chest, whipped off the condom and wanked until I splurged all over her face. As I rolled over exhausted she climbed onto me in the same positon and forced her dick into my mouth. She started wanking herself and it wasn’t long before her knees started to buckle and she came into my mouth. I swallowed her warm load whole and we both lied there next to each other.
After a few minutes she went to the toilet and next thing I heard the shower go. I walked into the bathroom and sure enough, she was lathering herself in the shower. I jumped in and forced her playfully up against the wall, pouring shower gel over her back and massaging her sexy little body. I pushed my body against hers as the hot water and soap foamed between us. I got hard again almost instantly and grabbed a condom from my bathing bag. I rolled it on, kissed her deeply, pushed her back against the wall and nudged my cock against her hole. I had it positioned so the head was just about to enter. I grabbed her hands, put them above her head and spread her against the bathroom and stuck it straight in. I fucked her against the wall until I was ready to blow again. I came inside her and we both cleaned each other before going back to the bedroom.
I asked if she would mind leaving and not spending the night. She agreed and took a taxi home. Never saw her again.