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Confused 20 Year Old First Timer

  • Written by 20 YOFT
  • August 31st, 2005
  • 7 min read


I was 20 years old and it was to be my first trip overseas. I was going to the UK on a working holiday. The travel agent told me I had to stop off somewhere on my way to London. He gave me a choice. Dubai or Bangkok. Dubai sounded interesting but it was too expensive. Bangkok? Where’s that?

Thailand? Ok, cool, whatever. We decided to stay for a week, 2 nights in Bangkok and 5 nights in Phuket wherever the hell that was.

It's funny when I look back at it, I had no idea what I was in for. I expected it to be a country full of all boring Asians that all look the same. I couldn’t even imagine it. I was only excited about London and all the party stories I've heard about the place.

So off we went to “Thailand”. God dam it nobody warned me. I was only a kid. And it was my first time away from home. It was one hell of a week I tell you. I just didn’t understand this place. One week you just don’t get it. And the women…what the? They were incredible, so damn charming.

Then it was over and we went to England. Don’t get me wrong I had a great time there for the next 8 months but I kept thinking about Thailand. What a weird ass place but how exciting! I wanted more. I was curious. And young.

I went back the following year. I was 21. I remember saying to my mate before we left, I am not sleeping with a prostitute, I am not sharing girls, I am not watching any of you have sex.

Funny the very first night we got there we did all of the above. And never in my wildest dreams would I ever have thought that I would sleep with a “ladyboy”. If you told me that 6 months before I would’ve laughed in your face. Yuk. As if. But I think the longer you stay in Thailand the more your inhibitions go. At least on your first time. I went up to Chiang mai to train Thai boxing for a while. I stayed for 3 months.

The first 3 weeks I didn’t do much, didn’t have any girls. I just thought they were all flirts. I didn’t understand them. One day I asked the waitress out to eat. She happily complied. Then we had sex all night. I couldn’t believe it.

The next day I asked the hairdresser out. She was thrilled to go out with me. Same thing happened. Within 2 weeks I had around 10 regular girls I was sleeping with. For a 21y/o this was heaven. And I just had the stamina to keep up.

Then one day I felt sick.

I felt empty. What the fuck am I doing I was wondering. I felt like a man whore. I never knew I could feel this way. I left Chiang Mai and headed to Bangkok.

There I met a guy who had been living in Thailand for 2 years, he was broke because his Patpong wife had gambled with the police and she owed money, so he spent his life saving bailing her out and now he didn’t even have money to eat. I helped him out and we became good friends. We went out one night and I was telling him how I'm sick of sex, sick of girls, it’s not all its cracked up to be. At the same time I thought gees these ladyboys are ok. They look like women with a twist. It was kind of sexy for me at the time. We went to a club, Gulliver’s on Khao Sarn. I had a few drinks so I got horny, there was a sexy lady eyeing me out. My mate says “that’s a ladyboy!” I was like no way! “Go for it!” That’s all I needed.

Within 5 mins I had a ladyboy sitting on my lap in front of all the backpackers in the club. I felt awkward. Embarrassed. This ain't me!! But I had to do it. She/he wanted to eat. So we sat on Khao Sarn having dinner on the chairs outside a café. Let me tell you I have never done anything like this before so I felt a little embarrassed when Danish backpackers would walk past and stare and especially girls! Ah! Anyway we went home and I did the deed.

I was too busy thinking “what the fuck am I doing” to enjoy the experience. Then I went to sleep. I had nightmares that night, I remember them clearly, 3 separate nightmares. Very disgusting nightmares. Shameful. Too weird to explain but they were sexually orientated. I woke up in the morning, looked at him/her, cringed, felt guilty and escaped outta there. I never thought I would do it again.

I went back to Chiang Mai for one last week.

I was taking a friend out and we started at a bar. We were drinking and this cute girl comes and sits with me, she just finished work. She is ok. We flirt and she says she will go change out of her work uniform and come back in 20 mins.

30 mins goes past and I'm thinking she ain't coming back. Besides there is this hottie eyeing me out at the bar across from me. So I went and sat with her. We start flirting and the original one came back. Gees I felt bad but I couldn’t do anything so I stayed with the one I had.

My friend found one girl he liked and we continued to drink at the bar. After a couple we both wanted to end the night early and take our girls to the room, but my one insisted I wait till 2am till her friend finishes. That was about 2 hours away. I was spewing but couldn’t do anything and she kept reassuring me “slowly but surely” while squeezing me. I couldn’t wait! I drank and drank and waited and waited and even begged at one stage lets go but I had to wait. FINALLY 2am came and she said ok lets go. I reached for my motorbike keys in my pocket and they were gone. Where I don’t know. I rushed to the toilet, they weren't there, I looked around the bar, nothing. Everybody left the bar and it was empty. I went to the toilet again and when I came back my girl was gone. Where did she go? Ill just wait. I was real pissed off. No key, no hotel. Where will I shag? I was drinking by myself at the bar waiting for my girl. Then I saw her driving off with another farang. Great. I am drunk, horny, I just got worked up for great sex and now I'm not even getting that, I can't even go home. I got no keys for the hotel or bike and my mates gone off the bastard with some girl. What am I to do now? So I stumbled out of the bar and walked… And walked. Then I found myself somewhere dark. I knew it was a ladyboy but she came up to me, I said no money no hotel, she said come to her place. I was desperate.

What happened next would probably have to be the most disturbing event that has happened to me to date. We had sex, but it definitely was a man this time. She had the operation and all, but this time I really felt the difference. I still went on with it but it wasn’t good. The voice…..the legs…..the back…..it was all man. Oh I was so yuk when I remember. I woke in the morning to find Barbie dolls everywhere in the room, porno pictures of cum all over the walls and a big large frame picture of her looking at me smiling with lipstick. I was repulsed that I got intimate with that last night. And I was sober. I got up, grabbed my wallet, pulled my pants up and sprinted out the door before she even woke up. I kept running and running and I was sweating from the heat. I got the main road and hailed a songtaew. I went home. From then I knew that I don’t like it. I just wanted to forget about it.

Looking back on it I can’t believe I did that.

Stickman's thoughts:

If true, this confirms what I have always said about coming to Thailand too young never being a good thing.