Tell me your first experience

[bernipes]

Hi everybody,

Wanted to find a thread where people tell their fist experience with a ladyboy, but can't find anything about in the forum.

So decided to open my own thread about it.

Would somebody tell me how was that first moment? The good parts, maybe something went wrong?

If there is already a thread, my bad, just tell where is it so i can check.

Thanks

[billyworld]

I'm game
My 1st visit to BKK was in 2011...I rented a small apartment in Lad Prao that I found on Air-B&B...I arrived with a 60 Visa and planned on doing 2 border runs to allow a 4 month stay
I had just taken an early retirement from UPS Tampa at 57 years old...I was divorced,no kids,no job...fuckin' free as a bird
I had been fortunate enough to have visited over 30 countries at this point in my life but had never been anywhere in Asia.
I don't consider myself gay because I'm just not attracted to men...but...
I was married to a flight attendant for 9 years and there is a large gay community in the airline industry...we had quite a few flaming gay friends and I always enjoyed hanging out with that group...they knew how to party hard
There was one particular guy that was especially effeminate that wanted to transition but was afraid he would lose his job...
I WAS attracted to him in a big way...but we never did anything.
So when I arrived in beautiful BKK and knew of the ladyboy community I decided to "swing for the fences!"
My first activity on Thai Friendly was very encouraging...I made 2-3 contacts my first day that were willing to come over for 2-3 hours of naked games
My first "victim" was a VERY petite LB named Green...she was 19 and stood all of 4 foot 11 (I'm 6 foot 5!!!)...she also had new braces on her teeth...cute does not even begin to describe her!
Her English was pretty decent and we talked about ourselves for 20-30 minutes and shared a cold Chang...she only took a few sips as she was not really old enough to drink yet
She noticed my camera gear and asked me to take a few snaps of her for her TF page...
so she played fashion model for me for about 1/2 hour...slowly unbuttoning her white blouse and slipping her butterfly panties down but leaving her pleated skirt on...soooooooooo fucking hot...this girl understood sex in a way that I had rarely experienced in the Western world...I knew at that moment that I was going to LOVE Thailand...LOL!
Her body fit her perfectly...literally no boobs but gorgeous dark inch long nipples,a tight little butt that fit in the palm of my hand and a super cute patch of trimmed pubic hair framed her lovely uncut cock...WOW!!!
She left her "girly" Mary Jane flats on while I led her to the bed which just made her even sexier...I was harder than I'v ever been I think...
I wanted to please this little gem so while we were kissing I was softly playing with her cock and balls...she was def on the small side but I didn't care...she was just plain beautiful and I was sure I was in love with this 19 year old Ladyboy!
I fingered her tiny ass while I sucked her cock and about 7-8 minutes later she came in my mouth...I was surprised and a bit flattered I guess because I had never sucked cock before and I suddenly fancied myself a fucking genius at it...LOL
I was still hard as a rock and I literally pulled her on top of me...she sat on my thighs and played with my cock for a few minutes and I asked if she wanted me to fuck her...
she said "yes please"...so we slathered my boner with lube and while she was sitting on my lap,she reached behind her and started slipping me into her "pussy"...no condom was stupid but we were just so hot for each other the subject never came up
I finally was into her balls deep and it felt like heaven on earth...I grabbed her by each side of her tiny waist and just started sliding her up and down...very slowly to make this moment last...
She played with my nipples while she was riding me and would occasionally lean forward for some long wet kisses...this girl was turning out to be one of the best fucks of my life!!!
I picked up the pace of our fuck slowly but surely and a few minutes later she was riding me like a rodeo bronc...I started spanking her little butt and she seemed to dig that...
but it sent me over the edge and I came buckets in that sweet back door of hers...OMG guys...I was hooked on LB's from that moment on!!!
We kissed for a few minutes and tried to cool each other down...then she wanted to take a shower together and I could have kept smearing those soapy bubbles on her tight body forever...
But she said she couldn't stay for another fuck because she had to catch a bus to Roi Et to visit her family for Songkran...
I gave her $100 and made her promise to message me when she returned to BKK but...
I never heard from her again
I think about her sometimes...she was my 1st and I will always remember that one with a giant smile on my face
green2_pp copy.jpg
green1_pp copy copy.jpg

[bernipes]

Wow, what story ...

Thanks a lot to share it ! i didn't know what to expect by posting that thread and if someone will even or not answer to it .. with your post you just did more than i expected

Yeah, the condom part was not the best moment of the story... but looks finally ok if i understand well
Anyway, nice to see that you first experience was so great.

I don't know if you saw it, but i never tried with a LB and i'm here in that forum to basically know more about them. So you can imagine that thread is important for me.
In that way, do you have some tips about wrong or good things to take care for a 1st experience?

Could be great if somebody else want to tell his 1st experience also,

Thanks again to you billyworld

[billyworld]

Hey Bern,
Glad I could help...and I really encourage you to explore your interests...
Regrets are typically a list of things we DIDN"T do...rarely things that we DID do!

Maybe I was lucky my 1st time but I will tell you this:
Thai Friendly is a VERY good place to start your search...there are no nude fotos allowed on the profile pages so you really can't "inspect the merchandise" but,
If you find a LB that seems really interested in being with you she can send a nude in the private message area...usually upon request.
Personally I have had VERY good luck on TF...even made a couple of lifelong friends
Be prepared for some "no-shows" and flakes but in my experience it doesn't happen too,too much!

Another alternative is of course the club scene...you can sit and talk to a variety of LB's before making any decisions...but that CAN get expensive...and the bar girls can get pushy by some accounts...bar fines at Nana /Cowboy were running 700B last year...that does NOT include $$ for sex tho...which you should negotiate before you pay the bar fine...if you take em' to your hotel room you'll save a little bit...but typically at Nana they want you to rent a room upstairs for an hour or 2...more out of pocket expense
Be prepared to spend $200 USD or more if you "cruise" Nana for 2-3 hours buying LB drinks and tipping the Mamasan.

No matter which avenue you chose to meet LB's...just do it!

Life is not a journey to the grave with the intention of arriving safely in a pretty and well-preserved body,but rather to skid in broadside,thoroughly used up,totally worn out,and loudly proclaiming:"WOW,what a ride!"

[Rattmaster]

My first experience happened during Songkran 2010. It happened while I was drunk and walking around like a zombie. My memory about the experience is pretty foggy, but I'll do my best to explain in detail.

It was in Hua Hin, the bar street called soi Bintabaht. I had been at the bars all day drinking with a friend, getting wet and enjoying the Songkran festivities. We started around late afternoon, and partied until well into the early morning.

From what I can remember, somewhere along the line I got separated from my friend as we both drank ourselves silly. It must have been after 2am, maybe later. All the bar girls moved over to the late night clubbing area and started afterhours freelancing. Soi Bintabaht had one ladyboy bar, which I had never been too, because my interest in ladyboys was little at this point in my life. I mean I had stumbled upon some ladyboy porn and didn't mind it, I did find some ladyboys attractive. So the idea of ladyboys was in the back of my head. But I never thought to myself then that I'd fuck with ladyboys. But a seed was planted, you could say.

Anyway, I remember walking around a dark nearly empty soi Bintabaht after some clubbing. This must have been 4am by this point. I eventually walked passed by that one ladyboy bar as they were closing shop. i was just walking by, no intention of interacting with them. Just trying to walk off my drunkenness. As I passed the shop, I was intercepted by the ladyboys, who were hanging outside as they were pulling down the front shutters. One grabbed my arm, squeezed by cock, and did everything in her power to seduce me....it worked. I was drunk, tired, and couldn't give a damn in the world. At that point I was easily persuaded for anything. My mind was in space already, and everything that felt wrong felt so right.

I think less then 5 minutes of mingling, I ended up on the back of a ladyboys motorbike. She drove us to a nearly short-time hotel, where she already had the room booked and ready to go. She stripped off her cloths (without revealing her cock), and we started to kissing in bed. As we were lying there kissing, I was rubbing her ass. I then reached a bit further back and touched the tip of her cock from behind. She had her legs crossed to hide it, still assuming I didn't know she was a ladyboy.

Oh I knew...I knew this was my first time trying out a ladyboy and was down for it. I throw all moral out the door, reached in and pulled her cock out to play with. As soon as did that, she look embarrassed, as if I discovered her secret, that she'd be caught. I played a long, and pretended to be shocked. She tried to apologize, but I just said "no no, it's ok". After that, things became more comfortable and I proceeded to suck her cock until she blew her load into my mouth...I swallowed. We made eye contact, and she had this surprised, and impressed look on her face. I had never done that before, but if felt natural. Unfortunately, I wasn't keeping track of time at all, so all this must have taken a hour already. As I got ready to tear her a new asshole and slip my cock into her ass, there was a knock on the door, our time had runt out. We had to collect our things a leave. I didn't get the chance to fuck her. So it was kind of an incomplete experience, but still decent for a first time. Luckily I don't think I had to pay for anything either. In hindsight, I think I should have ignored the knock on the door and at least fucked her ass for 5 minutes. Oh well.

So there ya go, that was my first experience

[bernipes]

Hey Bern,
Glad I could help...and I really encourage you to explore your interests...
Regrets are typically a list of things we DIDN"T do...rarely things that we DID do!

Maybe I was lucky my 1st time but I will tell you this:
Thai Friendly is a VERY good place to start your search...there are no nude fotos allowed on the profile pages so you really can't "inspect the merchandise" but,
If you find a LB that seems really interested in being with you she can send a nude in the private message area...usually upon request.
Personally I have had VERY good luck on TF...even made a couple of lifelong friends
Be prepared for some "no-shows" and flakes but in my experience it doesn't happen too,too much!

Another alternative is of course the club scene...you can sit and talk to a variety of LB's before making any decisions...but that CAN get expensive...and the bar girls can get pushy by some accounts...bar fines at Nana /Cowboy were running 700B last year...that does NOT include $$ for sex tho...which you should negotiate before you pay the bar fine...if you take em' to your hotel room you'll save a little bit...but typically at Nana they want you to rent a room upstairs for an hour or 2...more out of pocket expense
Be prepared to spend $200 USD or more if you "cruise" Nana for 2-3 hours buying LB drinks and tipping the Mamasan.

No matter which avenue you chose to meet LB's...just do it!

Life is not a journey to the grave with the intention of arriving safely in a pretty and well-preserved body,but rather to skid in broadside,thoroughly used up,totally worn out,and loudly proclaiming:"WOW,what a ride!"

Thanks a lot for the advices. Yes the next step is naturally signup in a dating website. To be honest for the moment i'm fine when i'm with you guys here. But yes i will probably soon i can imagine.

Thanks again billyworld

[bernipes]

My first experience happened during Songkran 2010. It happened while I was drunk and walking around like a zombie. My memory about the experience is pretty foggy, but I'll do my best to explain in detail.

It was in Hua Hin, the bar street called soi Bintabaht. I had been at the bars all day drinking with a friend, getting wet and enjoying the Songkran festivities. We started around late afternoon, and partied until well into the early morning.

From what I can remember, somewhere along the line I got separated from my friend as we both drank ourselves silly. It must have been after 2am, maybe later. All the bar girls moved over to the late night clubbing area and started afterhours freelancing. Soi Bintabaht had one ladyboy bar, which I had never been too, because my interest in ladyboys was little at this point in my life. I mean I had stumbled upon some ladyboy porn and didn't mind it, I did find some ladyboys attractive. So the idea of ladyboys was in the back of my head. But I never thought to myself then that I'd fuck with ladyboys. But a seed was planted, you could say.

Anyway, I remember walking around a dark nearly empty soi Bintabaht after some clubbing. This must have been 4am by this point. I eventually walked passed by that one ladyboy bar as they were closing shop. i was just walking by, no intention of interacting with them. Just trying to walk off my drunkenness. As I passed the shop, I was intercepted by the ladyboys, who were hanging outside as they were pulling down the front shutters. One grabbed my arm, squeezed by cock, and did everything in her power to seduce me....it worked. I was drunk, tired, and couldn't give a damn in the world. At that point I was easily persuaded for anything. My mind was in space already, and everything that felt wrong felt so right.

I think less then 5 minutes of mingling, I ended up on the back of a ladyboys motorbike. She drove us to a nearly short-time hotel, where she already had the room booked and ready to go. She stripped off her cloths (without revealing her cock), and we started to kissing in bed. As we were lying there kissing, I was rubbing her ass. I then reached a bit further back and touched the tip of her cock from behind. She had her legs crossed to hide it, still assuming I didn't know she was a ladyboy.

Oh I knew...I knew this was my first time trying out a ladyboy and was down for it. I throw all moral out the door, reached in and pulled her cock out to play with. As soon as did that, she look embarrassed, as if I discovered her secret, that she'd be caught. I played a long, and pretended to be shocked. She tried to apologize, but I just said "no no, it's ok". After that, things became more comfortable and I proceeded to suck her cock until she blew her load into my mouth...I swallowed. We made eye contact, and she had this surprised, and impressed look on her face. I had never done that before, but if felt natural. Unfortunately, I wasn't keeping track of time at all, so all this must have taken a hour already. As I got ready to tear her a new asshole and slip my cock into her ass, there was a knock on the door, our time had runt out. We had to collect our things a leave. I didn't get the chance to fuck her. So it was kind of an incomplete experience, but still decent for a first time. Luckily I don't think I had to pay for anything either. In hindsight, I think I should have ignored the knock on the door and at least fucked her ass for 5 minutes. Oh well.

So there ya go, that was my first experience

Thanks a lot Rattmaster for sharing
Nice first experience also, even if it was not 100% done!
Really liked the "I played a long, and pretended to be shocked" part

After that experience i can imagine you simply continued other experiences in that way totally naturally.

[Rattmaster]

Thanks a lot Rattmaster for sharing
Nice first experience also, even if it was not 100% done!
Really liked the "I played a long, and pretended to be shocked" part

After that experience i can imagine you simply continued other experiences in that way totally naturally.

I have always been the type of person, where if I'm put in a certain situation. I try to do it as naturally as possible.

When I was in college, I'd go to parties, and there would be some drugs. I had never done them before, and never intended too. I grew up a pretty good boy, and stayed away from risky business. But when people asked if I wanted to smoke a joint, and snort cocaine. I didn't want to be the lame guy. I wanted people to think I was cool like them. I didn't want to show that I was afraid of anything.

So this applies to ladyboys as well. Yes, it was my first time with a ladyboys, but I did my best to perform with her as if I had done it before. Really, I just treated her like a normal woman, but instead there was the added bonus of sucking her cock. I didn't really know how to suck cock, but we all watch porn don't we? So I've seen blowjobs thousands of times. I simply copied the techniques I've seen woman do in porn. And once you get going with it, you start to get the rhythm, and really get into it. Since that first experience. All my future sessions with ladyboys kept getting easier and more comfortable.

It's fun. The times that I pretend to not know they're a ladyboy. I like to see their reaction and expression when I act surprised they have a cock. But I don't keep up the act for too long. I mean once I get a glimpse of their cocks, its hard to hold back the urge to dive in and play with it.

[bernipes]

I didn't really know how to suck cock

I think we have an advantage as a men. We know what's good or not. even if i can imagine it's not that easy when you are in the situation for the first time

It's fun. The times that I pretend to not know they're a ladyboy. I like to see their reaction and expression when I act surprised they have a cock. But I don't keep up the act for too long.

Yeah it's really funny to read so i can imagine in real. Doing it too long can be uncomfortable for her i can imagine.

[bernipes]

BTW, did you have a bad experience to tell also? Maybe a situation to avoid?

[Frozen]

One more lucky and happy first timer
I first had the courage to pick an LB. 10 year ago, in 2010.

Her name is Katt, a Thai LB living and working in Denmark at that time, some wonderful memories.
What sent me off was a mix of curiosity, beauty and lust.

She was the only person available at the local brothel, the rest is history.
She talked me into be bottom for a start with lots of licking, kissing and finally gentle penetration, what a wonderfully feeling, later both top and bottom.

Perfect teacher both in bed and in kitchen, yes she did cook for me too, some of my favorite Thai dishes and I won’t bother you with the oil massage details where fingers occasionally tend to slip in a hole playing each other body’s.

On one occasion she was standing at the bed massaging my back just in front of my face.
That was my first blowjob, and yes I did swallow.
Our chemistry matched perfectly together, oh those fond memories.

It could be fun to meet her again, she is a lovely girl, guess she is back in Thailand, and she must be about 35 now.
She was my 1^st. LB. and still my no.1 favorit.
Was a regular at her shop for almost 2 years.

Nowadays I just want LB, no more GG for me too much drama.

They must be petite and feminine, thou when the moods strike; I go hunting for a Latino shemale from time to time, a lot of them here in northern Europe.
Guess I will try an Amazonian or 2 next time in BKK, but likes the most those small frame feminine Asian LB.

Curiosity, excitement and pure lust are what keep me going, and I was very lucky with my first time.
Best advice I can give, talk, kiss, play and repeat to establish some form of connection, you will be rewarded.

Thank you for this forum.

katt06.jpg

[Rattmaster]

I think we have an advantage as a men. We know what's good or not. even if i can imagine it's not that easy when you are in the situation for the first time


Yeah it's really funny to read so i can imagine in real. Doing it too long can be uncomfortable for her i can imagine.

Oh for sure, we know what we what right? I suck a dick the way I feel my cock deserves to be sucked. I mean when I say I didn't know how to suck, it's not as if I put her cock in my eye ball o r anything, like that ex pilot in the movie Airplane. Although...I actually do enjoy poking myself in the eye with their cocks...lol. I don't why, but I get off on that. I also like slapping myself in the face a bit just for kicks and giggles.

As for acting with the LBs. I just think it's funny. I mean, I'm in a ladyboy bar, the sign outside even says "ladyboys" on it. So after I bf them and take them to my room, they really think I don't already know? Most of these LBs, are exactly the ones that fooling anybody...lol. When I sense that they are doing that, I just like to push it a bit further. It's just fun to mess with people some times...lol

[Rattmaster]

One more lucky and happy first timer
I first had the courage to pick an LB. 10 year ago, in 2010.

Her name is Katt, a Thai LB living and working in Denmark at that time, some wonderful memories.
What sent me off was a mix of curiosity, beauty and lust.

She was the only person available at the local brothel, the rest is history.
She talked me into be bottom for a start with lots of licking, kissing and finally gentle penetration, what a wonderfully feeling, later both top and bottom.

Perfect teacher both in bed and in kitchen, yes she did cook for me too, some of my favorite Thai dishes and I won’t bother you with the oil massage details where fingers occasionally tend to slip in a hole playing each other body’s.

On one occasion she was standing at the bed massaging my back just in front of my face.
That was my first blowjob, and yes I did swallow.
Our chemistry matched perfectly together, oh those fond memories.

It could be fun to meet her again, she is a lovely girl, guess she is back in Thailand, and she must be about 35 now.
She was my 1^st. LB. and still my no.1 favorit.
Was a regular at her shop for almost 2 years.

Nowadays I just want LB, no more GG for me too much drama.

They must be petite and feminine, thou when the moods strike; I go hunting for a Latino shemale from time to time, a lot of them here in northern Europe.
Guess I will try an Amazonian or 2 next time in BKK, but likes the most those small frame feminine Asian LB.

Curiosity, excitement and pure lust are what keep me going, and I was very lucky with my first time.
Best advice I can give, talk, kiss, play and repeat to establish some form of connection, you will be rewarded.

Thank you for this forum.

katt06.jpg

Hi there, wonderful story. Your lady is beautiful, I'm surprised you didn't put a ring on her finger.

You definitely had a great first experience, very easy and relaxing. Much better than my first time...lol.

[Rgargizzzle]

My first experience seeing a ladyboy was in an adult magazine in France in the early 80s. We were travelling for a family vacation i was looking at the nudie mags at a magazine store and there was a few pages devoted to a ladyboy with a small uncut cock. It really made me horny I will always remember it.
My 1sr real experience was in the USA NW coast. I saw an escort from Hawaii who was totally feminine except for her small uncut cock. I don't remember too much except it was a hot experience. I remember playing with her little cock and it got super stiff but no bigger than 4 inches. I just stroked hers while I came in her mouth. I was surprised that she swallowed it and smiled.

[bernipes]

One more lucky and happy first timer
I first had the courage to pick an LB. 10 year ago, in 2010.

Her name is Katt, a Thai LB living and working in Denmark at that time, some wonderful memories.
What sent me off was a mix of curiosity, beauty and lust.

She was the only person available at the local brothel, the rest is history.
She talked me into be bottom for a start with lots of licking, kissing and finally gentle penetration, what a wonderfully feeling, later both top and bottom.

Perfect teacher both in bed and in kitchen, yes she did cook for me too, some of my favorite Thai dishes and I won’t bother you with the oil massage details where fingers occasionally tend to slip in a hole playing each other body’s.

On one occasion she was standing at the bed massaging my back just in front of my face.
That was my first blowjob, and yes I did swallow.
Our chemistry matched perfectly together, oh those fond memories.

It could be fun to meet her again, she is a lovely girl, guess she is back in Thailand, and she must be about 35 now.
She was my 1^st. LB. and still my no.1 favorit.
Was a regular at her shop for almost 2 years.

Nowadays I just want LB, no more GG for me too much drama.

They must be petite and feminine, thou when the moods strike; I go hunting for a Latino shemale from time to time, a lot of them here in northern Europe.
Guess I will try an Amazonian or 2 next time in BKK, but likes the most those small frame feminine Asian LB.

Curiosity, excitement and pure lust are what keep me going, and I was very lucky with my first time.
Best advice I can give, talk, kiss, play and repeat to establish some form of connection, you will be rewarded.

Thank you for this forum.

katt06.jpg

Nice to read that you also had a great first experience
Thanks for sharing it, it's so nice to read theses testimonials

BTW, sorry for my ignorance, but what's a GG?!