My First Ladyboy

Lea stood up and took off her pantyhose and her panties, and there it was. I was with a fucking ladyboy!

A member named Kelly posted this story at out forum, and i must admit that reading it was a big turn on! Thanks for taking your time to set it out in writing Kelly, and kudos to you 😉

I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers..

This particular Friday we were in the usual place chatting and having a nice relaxing time……when she walked in….taller than most Thai girls….but stunningly beautiful….long jet black silky hair.. halfway down her back, big eyes..small mouth..full lips….wow what a beauty…. I was watching her walking in ..when she looked over at me..and smiled.

I thought .”Kelly…don’t let this one escape”……so I followed her to the bar…and asked her if I could buy her a drink…

Her name was “Lea” ….over a couple of drinks she told me she was from a small town north of Bangkok.
We stayed in the bar, and drank a lot more beers….. I was getting a little too wobbly from all the alcohol and no food …. I suggested that we should grab a bite to eat….she agreed .. we found a small local cafe..and ordered some food.
Lea was lovely….her English was good..and we had a good conversation going …she was relaxing…and laughing at my jokes.
We finished the food..and headed back to my hotel…..

Lea was a sexy lover……she liked to kiss….tongue on mouth …lots of passion. I thought wow ..where have you been all my life…..I immediately got a huge hard on with her.
I was slowly undressing her……she had big tits….but I they were silicone…. this is normal for a lot of Asian girls…they have normally small or almost no tits, lot of them get boob jobs.
Lea had undressed me down to my shorts……and she was in her panties and pantyhose..
I thought I noticed a bulge in her panties….but between the beer and the dim light in the bed room….I dismissed it as shadows.
Lea….pushed me down on the bed…peeled off my shorts…and gave me a blow job…..and wow that girl knew how to use her tongue….I was struggling trying not to cum..my dick was rock hard.

Then she stood up at the end of the bed..and took off her pantyhose and her panties…….and there it was….I was with a fucking ladyboy…Geeze!!!

Her dick was hard..and standing up straight. I was stuttering ..saying “Lea…I though you were a girl” ……she smiled..and said…”Don’t worry…. .I wont bite you”
I had always thought that my reaction would be complete revulsion…….however to my surprise …I was still turned on……and….my dick was hard as rock…..she came over and kneeled over me on the bed..and started to stroke her dick…then she started to stroke mine….My initial shock..started to subside…and I relaxed a little more..I was starting to enjoy this new sensation……..she was slow and gentle.

Lea put on a condom on my dick with her mouth……….then she lubricated it …and finally eased my dick into her ass……god she was tight……..but I could feel her relaxing..and starting to glide up and down….I fucked her for hours….finally she sat over my tummy and masturbated until she came ..in huge spurts all over my chest….. Then she gave me a blow job until I came on her tits…….wow ….it was the best sex …………Wow.. what a lover…

I stayed with Lea for weeks..we had a great time..and lots of wild sex…She had to return to her family, I said a reluctant goodbye to her…she was crying as she boarded the bus, said she was falling in love with me……. She was my first Ladyboy….and I will never forget her.

I have had several ladyboy girlfriends over the past years….Once you experience sex with a ladyboy….going back to a girl is very boring in comparison..
As the song goes….”Take a walk on the wild side”….However a word of caution..once you start down that road…..going back to being straight..is kinds difficult.

I now travel to Bangkok and Manila as often as I can, to meet more beautiful Ladyboys.

Kelly.

16 thoughts on “My First Ladyboy”

  1. …and here it is. I went back to Casanova some months later, hoping to see the well endowed one. She was dancing on stage – we made eye contact, she hopped down straightaway and we kissed, while our cocks gently rubbed into each others! Her name was Yoko. We did the deal and headed back to the hotel not wasting any time. She bounded into the room and in no time she was on the bed, panties down and me sucking her gorgeous dark pointy cock upright. I had no idea where this encounter was going to go, but when she asked me if she could fuck my ass – well – a gentleman can hardly refuse. She pushed me face down on the bed and lubed my ass and got to work with two fingers to get me loosened up. She tried to enter me – it didn’t work well plus I wanted to see everything – so I rolled ono my back, raised my legs, presented my virgin asshole and soon I felt a first ever cock probing my bud. She slipped in, taking plenty of time to let my ass adjust, and soon got into an amazing rhythym and fucked me solid. We then swapped over – and for the first time in my life I could see my cock sliding into an asshole – every dream coming true. I couldn’t help myself and came quite soon. The whole thing was like something out of the most amazing dream – gorgeous woman with a great smile, awesome tits, willing ass and a hard cock – what’s not to like about that!!!

  2. Damn, I get so horny seeing them, I put on pantyhose myself and mmmmmmm what an imagination. I can’t wait to meet another person who enjoys sexy lingerie and hose. especially one with breasts.

  3. I’ve been going back to Bangkok for 6 years now, the first year I only fucked girls but on the last night got a bit drunk and took a lady-boy back to my room, I’d never been with a guy before let alone a transsexual but it was the most enjoyable sex I’d ever had, the blow-job was perfection and my first anal sex? well I thought I’d never stop cumming, she laughed when I’d finished “your first time with a lady-boy” next year it was lady-boys every day, at least 2, sometimes 3, the sex was and still is SUPERB! always go for the pre-op girls cos the anal sex is out of this world, I can best describe it as like going into “liquid velvet” you will cum like your’ve never cum before, BUT, always wear a condom, AND, never pay more than 2000baht.

  4. Last time I was in manila I took 2 superb beauty ladyboys in my room and they fucked me at the same time.One was lying on his back and me sitting on her big 7 1/2 inches cock facing her and the other took me from behind with his big 8 inches cock.At first it was painful then after my arse was relaxed it was perfect.I had 2 big cock all the way inside me and I was in Heaven.

  5. i just got back from england seeing a friend.he took me to a club were xdressers ,tvs trans and lady boys go. my friend is none of the above,but likes to have fun .i met his friend who has never been with a lady boy.i was dressed nice,white courset,sheer seamed stockings,white thong,white 6in heels gray short tightdress low cut to show off my 38 c breasts.it was not long before i could see him looking at me.we danced a few slow ones and i could feel his cock grtting hard.i asked him if he wanted me to do something for him.he said ok and we went into the back room.i took off my dress and his pants and shirt and started to suck his big black cock.iended up bent over and his cock up my ass.my friend come in and put his cock in my mouth.they took turns fucking and getting bjs.i also fucked both of them and made them suck me off

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