An Unexpected Experience of a Different Variety (Ladyboy)

[Chopsumbong]

Recently had gotten back from my holiday at Bangkok. Partying at Sukhumvit road was amazing. However the thing that caught my eye the most was the ladyboys. I came across some of the most beautiful “women” I had ever seen. I was told ladyboys were accepted in Thai culture and there was no stigma attached to the alternative sexuality here. It got me thinking of what it would be like spending intimate time with these ladies, but I had also read about stories where tourists would get robbed by ladyboys in Thailand and thus decided to skip but the thought of these women never quite left me.

When back at Singapore and one day scrolling through a dating chat app I came across a beautiful Thai specimen similar to what I saw on my trip. I immediately got talking to her and found out she was indeed a pre op ladyboy visiting Singapore. Jane was about 25 years old, had a beautiful face with makeup, a sweet smile, Long legs and a large set of fake breasts. She was polite and funny throughout our chat and was asking me to visit her room and give her a go. She talked me through my hesitations and patiently answered my queries. She made a point saying it wasn’t gay just sex. Anyways it was a Saturday night and I had nothing planned so I gave in and decided to pay her a visit, worst case if I felt weird I could just leave.

I made my way to her hotel in River Valley and waited at the lobby for her to take me up. As she arrived I was astounded, she looked amazing wearing a tight short dress with high heels and her large breasts on display. She gave me a light kiss and a hug and asked me to follow her to the lift. Once in the room Jane and I had a smoke on the balcony. Her voice was somewhat deep but she controlled it well and most part sounded like a woman. After the smoke we went back to the room and decided to start. I was nervous but her friendliness and how hot she looked calmed me down.

Jane and I engaged in a Long passionate kiss, she knew what she was doing and was a good kisser. She then stripped off her dress and stood before me in just her g string before removing my pants and slowly stroking my cock. She mentioned I had an impressive cock and soon she bent down and took my cock into her mouth and began giving me an amazing oral, it was probably the best oral I had ever received. Jane would suck my balls before returning to my cock. I was hard as a rock and full horny when Jane asked me to hop on the bed as she stood up and removed her underwear. I had now seen her cock. It was not yet hard and had light trimmings of pubic hair around it. Her balls were quite small. I was more curious than taken back at that point. Here was an attractive girl with large fake breasts and also with a cock. Jane joined me on the bed and began kissing me while slowly tugging my cock, I began to slowly grope her large breasts before she moved my hand down to her cock. For the first time I had held another cock. Jane grinned and said “you like that Darling?” I was well too horny to be thinking straight and soon we were both giving each other a handjob whilst kissing. Jane’s cock had now grown and she had a reasonable size cock about 5 inches. Both of us were enjoying wanking of each other. Jane then asked me to fuck her as she reached for a bottle of lube for her asshole. I rubbed the lube on her asshole before she got into the doggy position. I slowly pushed my hard cock into her asshole slowly which made her let out a seductive moan, soon my hard cock was deep in her asshole, I was fucking her asshole raw without a condom and it was so so tight and amazing. I was pumping away careful not to cum. As I fucked her in doggy I would also tug on her cock which added to her pleasure. Jane was enjoying my Long cock in her asshole as she took charge and asked to change to different positions. We switched from her riding me to reverse cowgirl. Jane got up and walked seductively to the table. She looked amazing in her high heels and long legs. I went toward her and bend her town and began smashing her asshole making her wail in pleasure. Soon I was about to blow and just shot my cum deep into her asshole. It was the best orgasm I have ever had. I pulled out of Jane and there was some cum dripping out of her asshole. Jane smiled and asked if I enjoyed it. I noticed she was still hard and asked her if it was possible for her to ejaculate as well (I wasn’t even sure if it was able to shoot out cum) but Jane said “ yes darling can make me shoot?” I was still horny and asked her to get on the bed as I with a dripping cock went to join her. I began kissing her and started tugging her cock and picked up speed till she too cummed with some cum landing on my stomach. Jane then got up and started sucking my cock and cleaning off the excess cum.

We both showered as I decided to stay the night over with Jane. We fucked another time that night and before I left the following morning, Jane gave me another amazing blowjob till I cummed into her inviting mouth and which she swallowed.

Jane and I kept in contact and I’m hoping she’ll return to SG again. Never thought I’d fuck a ladyboy but it was an amazing experience.






Pictures of Jane.

[bigboi21]

bro what dating app u use

[LiverBird8]

She's on Michat now.. can see her profile there.. lol

[henry_ang10]

sorry TS, after reading your story, I feel like vomiting

u have just engaged in quasi-gay sex i think..

[des4fuck]

Bro she is back in sg found "her" in michat , u want to rtf? hahah

[Chopsumbong]

Originally Posted by henry_ang10

sorry TS, after reading your story, I feel like vomiting

u have just engaged in quasi-gay sex i think..

Just means you’re a closet faggot if you’re repulsed by it.

[peregrene]

Originally Posted by henry_ang10

sorry TS, after reading your story, I feel like vomiting

u have just engaged in quasi-gay sex i think..

Some like it and some do not.

It is not something I would do, to be honest but really...to each their own

[Joesports]

Raw is WAR bro, be careful man

[aurahiongka]

Originally Posted by Chopsumbong

Recently had gotten back from my holiday at Bangkok. Partying at Sukhumvit road was amazing. However the thing that caught my eye the most was the ladyboys. I came across some of the most beautiful “women” I had ever seen. I was told ladyboys were accepted in Thai culture and there was no stigma attached to the alternative sexuality here. It got me thinking of what it would be like spending intimate time with these ladies, but I had also read about stories where tourists would get robbed by ladyboys in Thailand and thus decided to skip but the thought of these women never quite left me.

When back at Singapore and one day scrolling through a dating chat app I came across a beautiful Thai specimen similar to what I saw on my trip. I immediately got talking to her and found out she was indeed a pre op ladyboy visiting Singapore. Jane was about 25 years old, had a beautiful face with makeup, a sweet smile, Long legs and a large set of fake breasts. She was polite and funny throughout our chat and was asking me to visit her room and give her a go. She talked me through my hesitations and patiently answered my queries. She made a point saying it wasn’t gay just sex. Anyways it was a Saturday night and I had nothing planned so I gave in and decided to pay her a visit, worst case if I felt weird I could just leave.

I made my way to her hotel in River Valley and waited at the lobby for her to take me up. As she arrived I was astounded, she looked amazing wearing a tight short dress with high heels and her large breasts on display. She gave me a light kiss and a hug and asked me to follow her to the lift. Once in the room Jane and I had a smoke on the balcony. Her voice was somewhat deep but she controlled it well and most part sounded like a woman. After the smoke we went back to the room and decided to start. I was nervous but her friendliness and how hot she looked calmed me down.

Jane and I engaged in a Long passionate kiss, she knew what she was doing and was a good kisser. She then stripped off her dress and stood before me in just her g string before removing my pants and slowly stroking my cock. She mentioned I had an impressive cock and soon she bent down and took my cock into her mouth and began giving me an amazing oral, it was probably the best oral I had ever received. Jane would suck my balls before returning to my cock. I was hard as a rock and full horny when Jane asked me to hop on the bed as she stood up and removed her underwear. I had now seen her cock. It was not yet hard and had light trimmings of pubic hair around it. Her balls were quite small. I was more curious than taken back at that point. Here was an attractive girl with large fake breasts and also with a cock. Jane joined me on the bed and began kissing me while slowly tugging my cock, I began to slowly grope her large breasts before she moved my hand down to her cock. For the first time I had held another cock. Jane grinned and said “you like that Darling?” I was well too horny to be thinking straight and soon we were both giving each other a handjob whilst kissing. Jane’s cock had now grown and she had a reasonable size cock about 5 inches. Both of us were enjoying wanking of each other. Jane then asked me to fuck her as she reached for a bottle of lube for her asshole. I rubbed the lube on her asshole before she got into the doggy position. I slowly pushed my hard cock into her asshole slowly which made her let out a seductive moan, soon my hard cock was deep in her asshole, I was fucking her asshole raw without a condom and it was so so tight and amazing. I was pumping away careful not to cum. As I fucked her in doggy I would also tug on her cock which added to her pleasure. Jane was enjoying my Long cock in her asshole as she took charge and asked to change to different positions. We switched from her riding me to reverse cowgirl. Jane got up and walked seductively to the table. She looked amazing in her high heels and long legs. I went toward her and bend her town and began smashing her asshole making her wail in pleasure. Soon I was about to blow and just shot my cum deep into her asshole. It was the best orgasm I have ever had. I pulled out of Jane and there was some cum dripping out of her asshole. Jane smiled and asked if I enjoyed it. I noticed she was still hard and asked her if it was possible for her to ejaculate as well (I wasn’t even sure if it was able to shoot out cum) but Jane said “ yes darling can make me shoot?” I was still horny and asked her to get on the bed as I with a dripping cock went to join her. I began kissing her and started tugging her cock and picked up speed till she too cummed with some cum landing on my stomach. Jane then got up and started sucking my cock and cleaning off the excess cum.

We both showered as I decided to stay the night over with Jane. We fucked another time that night and before I left the following morning, Jane gave me another amazing blowjob till I cummed into her inviting mouth and which she swallowed.

Jane and I kept in contact and I’m hoping she’ll return to SG again. Never thought I’d fuck a ladyboy but it was an amazing experience.






Pictures of Jane.

she stay in singapore i know her

[henry_ang10]

Originally Posted by peregrene

Some like it and some do not.

It is not something I would do, to be honest but really...to each their own

haha.. not for me.. is almost gay-sex already...

Some ppl got holes can fuck liao.. thumbs up for them

[hayhay]

This lady is In Singapore, how much u paying her? Steady lah brother

[Haha5555]

Salute your bravery for going raw

[PaPaSm00th]

You sure very brave. Just wondering if anyone come across any ladyboy which have gone for operation.

[Steventan]

TS, thanks for sharing your adventures.

[blackknight24]

Originally Posted by hayhay

This lady is In Singapore, how much u paying her? Steady lah brother

Ah gua also reject u ? Better go mati sua