first time and tricked with a ladyboy

[Cunningham]

First time writing about my stories, and I have many... but my first time I ever came across ladyboys I was 23 years old and travelling in Thailand .
I had Been in Bangkok on the typical backpackers trail, had seen the ping pong shows and seen ladyboys on the streets and clubs, but they didn't float my boat ... found them intimidating at that age and a bit too manly.
Much preferred to hook up with the tourists to be fair ..
That changed when I travelled to Koh Samui, I met 2 English girls and an American guy on the mini bus to our accommodation and we became friends for a while. I actually hooked up with the English girl on the first night and was with her the whole time they were there (5 days)
We did the usual things staying at Charlie's huts on the beach for only £1.50 per night hanging on the beach , getting cheap drink then heading into chaweng to the dancing at Green Mango...
An open air nightclub full of tourists and locals .
Anyway the English girls were worse for wear and decided to go back to the accommodation , whilst i stayed on with the American guy...
Not long after the American guy was hooking up with some tourist on the dance floor so I went to the bar and got a drink, but at the bar I had noticed this stunning Thai girl, you know that kind of feeling u get when it takes your breath away, and I just become transfixed on her beauty and nothing else matters... well that was me ... OMG ! She had long dark straight hair , she was wearing these black leggings( love leggings) that showed off her perfect arse..
anyways I moved back from the bar with my drink and leaned up against a pillar about 5 m away so I could get a clear view of this perfect file without getting caught ...now I had had a few drinks and I thought I was discreet, but obviously not, I couldn't take my eyes off here perfect bum and had dreams of what I would do with it... but even with booze in me I wasn't brave enough to try and speak with this beauty ...
Im guessing that I may have been a bit obvious in my gaze as I saw her friend who I could tell was a ladyboy giggling and looking over st me whilst whispering to me ... I felt I had been caught and was about to go as I now felt embarrassed..
When she came over next to me , didn't say anything, but just starting slowly dancing next to me whilst looking over to her friend and laughing ..I was both nervous, embarrassed and excited... something told me to leave, being shy, but I couldn't move my legs...the feeling of nervous less and excitement was driving me wild inside.
Next I knew she was slowly girating her little bum in those perfect leggings up against her groin, feck me , suddenly I was in heaven , and to this day I swear I have not had as big a hard on since... it felt like the skin on my cock was too tight... I was in heaven.... this went on for about 30 sec and she then pulled away and looked me in the eyes and said u no like?
I just nodded.. scared and excited... she then continued and at this time I worked up the courage to place my hands on her hips hoping she wouldn't leave ... she didn't , and man did she feel nice .. her soft cotton leggings felt amazing as inbrished my hands up and down her thighs, she continued and before long we were kissing .... I was in absolute heaven ...
She then said u come to mine now ? Yes I said... 500 baht she said... I was a bit shocked as I had never paid for anything before, but I was a lot more excited and I would have given her all my savings to be with her at that moment ..
So we got on her scooter and I was behind her like a horned up teenager bursting and caressing her whole body... after a few minutes she took me into small flat, just a bed and a small kitchen and a separate bathroom... I wasn't caring where I was , I couldn't think straight , I was so full of lust..
We got into the bed and she took my clothes off, and started giving me a blowjob , the type I had never had before first really slow just flicking her tongue against the head, I was in agony wanting more .... at that point she took off clothes and that is when I was in total shock.... she had a cock? What ? Fuck!! No .., shit !!
I remember saying to her , I'm not gay , and you can't be ? I was so confused ... but she said yes I ladyboy.. I though u knew ?
Aaah. No!! ???
She then said nothing to worry about , and started to lick my cock again , I bet all was saying no , but physically she could see I was still saying yes...
At this point I remember thinking I'll do it once and that will be it ...justifying it in my head ..
Anyway she got me in such a state and then placed a condom on and went on top of me , very slowly easing herself down... it felt amazing .... I had never felt anything so tight against my cock... she was only going slowly as I could see it was hurting her a bit , but it only took four or five slides up and down my cock for me to explode... it was out of this world, I felt like I was going for a minute...
As soon as it had finished , she got off and showed me the condom... I'm not sure I have ever come hat much before ...
My feeling of happiness immediately turned to guilt, and I quickly got up and left ...
I remember feeling so confused, I didn't know what was going on in my head... am I gay now? I went back to the hut and straight into bed with the English bird and gave her a seeing too , I was humping her, but could only think of this perfect ladyboy that had completely tricked me ...
After a few days he English girls left, but I stayed on, and I had one thing on my mind and I found my perfect lady it again and spent 5 more nights with her ... I was hooked ... at that time I never touched her cock, it wasn't for me ... and to be fair I can take it or leave it these days as well..
hat was how I got hooked ...I love ladyboys... I am happily married now with kids. It I still can't take myself away from the occasional meeting ...
their bodies are just amazing ...
I hope u enjoyed my first meeting ... plenty more to come ..

[blackshemalelove]

good job man...thanks for sharin....feel u 100% as mos of us do

[Cunningham]

Amazing story…
Your story was almost exactly the same as mines … I can’t. Believe it
Charlie’s hits was pumping a London girl, went to green mango, girls left, hot Thai girl rubbing up against me , back to hers 500, on scooter touching …
Small bed sit, ladyboy … first time guilt, but blew and left … then found her for the next 3 out of 5 nights …
Still tamper with true ladyboys today ..
Bodies from heaven