First Time With A Ladyboy
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First Time With A Ladyboy
My First Time Sex With A Thai Ladyboy
Last updated: April 7th, 2020
| in Ladyboys
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At home everyone tells you to be careful with Thai girls especially those that are “too beautiful” to be true. Be careful with what? Well of course the main reason why I’m coming to Thailand (and most other guys I know) are not the beaches which are more beautiful in other countries like Australia or Brazil or the spicy food on the side of the road that I tried to avoid after my first week here. The main reason for any of my trips to Thailand is sex and plenty of it.
Until recently I was not even thinking about having sex with a Thai ladyboy, when out in the bars looking for a hook up I was always trying to figure out ways to spot the difference between Thai girl and ladyboy . Until recently? Well yes, I did it. And not even by accident. After thinking about it for quite a while I thought I write it all down and share it with you guys here. I’m sure a lot of people at least think about trying it out just like me but they don’t really know how to go about it and what to expect. Sure, the easiest way is to simply book an escort on ladyboysbangkok.com , but in my case I went for the nightlife option first.
Already at home I booked my hotel in Bangkok online: I decided to stay at the infamous Nana Hotel for a couple of nights before heading down to Pattaya. I have never seen a place like this. I’m not talking about the rooms which are pretty standard and actually a great deal. No what I mean is it almost makes you feel like in a short time hotel, you can basically sit in the lobby and watch foreigners walking in and out with the ladies every two or three minutes. The hotel is located on Sukhumvit Soi 4. Some call it “the city’s beer bar capital” but it’s most famous for being home of Nana Plaza, a three floor building packed with Go Go Bars – and literally right opposite the Nana Hotel.
So on my first evening back in town I went to Nana Plaza at around 8:30pm – just about the perfect time since most guys are sticking to the beer bars and the 80 Baht a beer happy hour. In the Go Go’s in Nana Plaza most of the staff is already there while the bars are just about to get filled up with the male customers means you have like the full range of girls to choose from.
I was walking around the complex and it wasn’t so easy to make up my choice as there are just so many bars and the girls were stunning hot and tempting simply everywhere. After ten minutes or so I just thought ok let’s try that one, went in and ordered a beer. However soon I knew that I wasn’t going to take anyone out from there, the girls were more average looking on a closer sight, not really enjoying dancing on stage and the one girl I liked and paid two tequila lady drinks went back dancing before sitting down next to a Japanese guy. I left that place after paying my bill of 500 Baht including some minor tip.
Somewhat disappointed but still in mood for getting laid I started looking at other Go Go Bars. In front of some place on the second floor a fairly slim and tall (around 1.75m) stunning blonde and busty chick started to hug me and whispering “Why are you so handsome” in my ears while uninhibitedly grabbing in between my legs. I was like oh my god and told her “Why are you so sexy” before putting my hands down on her… dick. Dick! She was a ladyboy! I ran into a ladyboy and would have never noticed it by just looking at her. Somewhat embarrassed I said ohh, thank you it’s ok see you naa.. and went off the scene.
While continuing my walk around Nana Plaza, a new thought started popping up on my mind again and again: Why not just trying out sex with a ladyboy? Might be a freaking awesome experience – she was super hot and I might regret it later if I didn’t do it. I think it was more or less spontaneous and intuitive that I was suddenly turning around and walking back to the spot I left five minutes ago.
My ladyboy was still standing in front of the bar together with some of her friends and my reappearance put a charming and sexy smile on her face. I asked her for her short time price expectation and after some negotiation we agreed on 1,000 Baht plus 700 Baht for the bar fine and 350 Baht for the rental of a short time room on the top floor of Nana Plaza. Altogether 2,050 Baht – not too bad I thought for this hot Go Go Ladyboy and I didn’t have to spend any more on lady drinks.
So I handed her the bar fine which she brought inside and after getting her handbag and putting on some more make up we walked hand in hand up the stairs to the top floor where the short time places are found. The atmosphere here was completely different to the bustling scene of the bars on the floors below, very quiet and there were absolutely no people around. I was really excited by then. We entered the place and found a woman sitting somewhat bored on her desk that I paid the 350 Baht for the room.
We moved on and into the room that wasn’t very spacious, but it was clean and had a nice Queen Size Bed with a couple of towels as well as a pack of two condoms on it. I closed the door and without wasting any more time I put my hands on her beautiful big and firm boobs while kissing her cheek. She started giggling while massaging my dick. We undressed each another and went to the small enclosed bathroom where we took a shower, rubbing on one another with lots of soap. This was also when I first saw her penis which was pretty small like the one of a 13 year old. Her balls hairy and more like that of an adult though.
After finishing our shower and drying each other off we went over to the bed. We started touching each other. Once again I had to start with her amazing boobs but soon I felt doing something completely new, weird and exciting at the same time: I went down with my hand and started masturbating her penis. It didn’t take long for it to stand up and become tight and my ladyboy started moaning, firmly grabbing my shoulder. I got horny by that and got a boner as well.
After a while I was just about to go on to the next part when she put her hand on mine saying “Don’t stop baby I’m coming”. I sped up my movements and so she moaned even louder and shortly after she shot out her load. She hopped out of the bed and went to the bathroom to clean herself again.
Now it was my turn. I lay down on my back and my ladyboy started sucking my dick. It felt amazing. She did it without using her hands. It felt so good I had to ask her for small breaks to avoid coming too quickly. After a while I felt like now it was time for nice sex and I told her that I wanted to bang her.
She put on the condom on my dick, applied some baby oil that she had in her handbag and started to passionately riding on me while I put both of my hands on her big and firm ass. Her small cock was clapping on my belly. She didn’t stop and since her anus was quite tight it didn’t take long until I couldn’t hold it back anymore. Now it was me moaning loudly while cumming inside her.
I stayed in her for a short while and looked at her beautiful body, before we both went to the bathroom again for another shower. We dried each other off, got dressed and I handed my ladyboy her love reward of 1,000 Baht. We walked back to the go go bar where I gave her another kiss on her cheek before I left. I was so glad I had the guts to try sex with a Thai ladyboy – and I immediately knew it shouldn’t be a once in a lifetime experience.
After arriving in Pattaya a couple of days later I felt like doing it again. But instead of spending another 2,000 Baht for buying a ladyboy in a bar I tried a different way that many of my friends recommended me. I signed up for that Online Dating Site and wrote a message to some random attractive ladyboy in town. Since she was online at the same time it didn’t take two minutes until I received her reply and after some standard small talk I asked her if she wants to meet for some dinner. She said she was too lazy now to go outside and if I wanted to watch a movie at her place instead. Two hours later I had sex with my second ladyboy in Thailand.
It’s really that easy and I did it not just in Pattaya but also when I returned to Bangkok, the site has ladyboys looking to have some fun with foreigners simply everywhere. Are they asking for money? Yes some do, but it’s never more than 1,000 Baht. Some just say “up to you” and I give them 500. Don’t get me wrong, I still like Thai girls for girlfriends, but once in a while it’s just super exciting and fun to have sex with a Thai ladyboy, especially what I found most Thai girls have sex primarily to please the guys whereas the ladyboys seem to really enjoy it.
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My First Time Sex With A Indonesian Ladyboy
Last updated: July 8th, 2022
| in Asia | Indonesia | Ladyboys
© 2022 Girls Heavens. All rights reserved.
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When I look back at what happened during the past 3 weeks, I still can barely believe it. I just got home from my first trip to Bali, and I’d like to share this story with you guys. I’m 47 years old, decent looking, divorced. It wasn’t my first time in Asia – I had already been to Thailand twice, but never even considered the possibility to do what I did there in Bali. Or maybe it was just the missing opportunity? Possibly.
So here it goes. I had arrived at my hotel in a relatively quiet back street of Jalan Legian in Kuta, which is, in case you don’t know it, the prime nightlife strip of the island.
The first couple of days and nights went by pretty normal , I took it easy during the daytime by relaxing at the beach and strolling through the Beach Walk Shopping Center and also in the nighttime I didn’t do anything much exciting, I just had a few drinks in the bars, did some people watching and went on a few walks to check out the red light action.
Strangely, there wasn’t much of a girly bar scene – nothing compared to Nana, Pattaya or Phuket in Thailand. I didn’t see any hostess bars at all (I only found them after reading the guide on GH actually) and the only hookers I spotted were freelancers on the streets (“massage, mister!”) and the ladies in the night clubs, especially Sky Garden.
I didn’t do anything with them though as they had horrendous price expectations – no one was willing to go for short time for less than 1 million! Ridiculous.
So my frustration was quite big on my fifth night in Bali , when I was on my usual exploration walk around the area. And then it happened: In one of the side streets of Jalan Legian I saw about five hot chicks standing in front of their shop, which turned out to be a massage salon. Oh, just another place where they try to scam you with their “sexy massage” offers, I thought to myself.
But as I came closer, it turned out that it wasn’t just another typical massage salon with average looking women – those masseuses were hot, incredibly hot. One of them walked close up to me and offered me a body massage for “only eighty thousand” with a confident smile. I looked at her body and almost couldn’t believe it: Big tits, white skin, firm butt, dark eyes, juicy lips, long black hair – and she was petite, about 1.50m.
My dick thought the same and got hard the moment she looked at me (well, probably even before that). And it didn’t even matter to me that she was obviously a ladyboy (I did the finger trick to confirm my assumption).
I almost reflexively turned down her massage offer as I had done so many times before, but then I stood still and thought for a moment. I hadn’t touched any of my daily “entertainment budget” so far due to the lack of reasonable offers. Now I had this incredibly sexy chick in front of me, so why not just give it a try? It was probably just a massage with hand job happy ending anyway, so why not try it out once. You never try, you never know.
So I looked at her, smiled and said: “Okay”.
We walked up the stairs and into a big room with about six massage beds, each divided with a curtain. There was one other customer (I could hear him excitedly chatting with his masseuse, obviously also a ladyboy judging from her voice), and she led me to the bed next to them. She told me to “take off everything” with another damn erotic smile and went out to get her equipment.
Just as I had taken off all my clothes and was about to grab the towel she suddenly came back in, holding a small basket with oil and tissues, and looked at my naked body and dick, that got even harder in that moment. She put the basket on the bed, walked right up to me, touched my stomach with her hands, while circulating and moving slowly down. She breathed in my ear and whispered “hand job okay?”.
We had a small discussion on the price, she asked for 700k first, but I got it down to 400k (including the price for the “massage” that never actually happened), and then she put plenty of oil on my dick and rubbed it up and down – while standing right there. It felt so good, she was moaning and not shy at all considering our neighbors. I could barely hold it for three minutes, and shot off my load with my one hand on her perfect ass, the other on the massage bed and my eyes alternating between her big boobs and her passionate face.
That night I could barely sleep – I constantly thought of that experience in the massage salon. It was one of the best hand jobs I ever got, and imagined how it would be if we actually had sex.
I went back to her salon the next day, and when she saw me, her smile was even bigger. Funnily, we didn’t even say anything other than “hi” before walking straight inside – we both knew what would happen. And she didn’t even try to negotiate a price when I pulled down her black dress to uncover her big tits. I sucked them like a small baby, while she had her hand on my pants, and shortly after she pulled them down as well.
I took off her dress and could already see the dick inside her panty – but I didn’t even bother. Well, I actually got even more excited, I just wanted to try it out. I took it off and slowly rubbed it up and down. She moaned even louder than the day before, and I found it erotic, exotic and fun. She shot off her load after about five minutes.
And then it was my turn and time for the sex. I took out a condom from my bag in the pants (I usually prefer to use my own due to size and safety issues) pulled it over my penis and started banging her doggy-style. My hands on her wonderful ass first, and then leaning forward to grab her bouncing melons. And you know what, even though I had pictured all sorts of different positions I wanted to try with her – I couldn’t hold it for very long, she was just so hot.
I gave her the same amount like the day before (400k) which she was happy with, we kissed us and I left.
And again, I couldn’t stop thinking about that sexual experience with that cute ladyboy – I wanted to repeat it. But instead of going back to that same salon and paying more cash, I tried out the dating site route .
From what I had read on most “guys websites” like this one, My Ladyboy Date is the biggest site in Indonesia to meet up with shemales who don’t ask for money (= no hookers). So I signed up on there and browsed through the members – there were lots of pretty hot chicks on that site, I contacted a few, and it didn’t take long until I was in a conversation with someone originally from Sumatra who worked in a restaurant up in Seminyak.
We arranged a dinner near my hotel in Kuta, which went well, very well actually, we had a nice talk, and the chemistry was great from the beginning. She had a nice sense of humor, seemed to be genuinely interested in me, and well, she was well equipped under her white shirt as well, that was obvious.
I invited her to my hotel after dinner, to “hang out” for a while and to watch a movie (the standard tactic) and she agreed. One hour later I had my second sex with an Indonesian ladyboy, and the third orgasm in 3 days. I’m actually still in contact with her, and already planning my next trip to Bali later this year.
Now please don’t think I’m gay because I had sex with these ladyboys. That trip to Bali has just opened my eyes – ladyboys are the third gender , and they cannot only be really attractive and sexy, but also fun to spend time with. Well yeah, I guess they do “know what a guy thinks and likes”.
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