Tell me your first experience

[Rockheart]

Well my first trans experience was in New Orleans way back in the day. I went on a business trip to Atlanta then took a couple weeks off and took the Amtrak to New Orleans. I had never been with a tgirl but I knew this was the place to do it. So i went to a club on Bourbon Street called Papa Joes, it was a trans cabaret show and bar.
This bar was very popular at the time as there was few trans bars anywhere. It had many well known tgirls working there over the years such as Megan Chavalier.

I went in and it was pretty seedy but i got a chair and watched the show which was usually just one tranny dancing. A marginally attractive tgirl sat beside me and asked for a drink, so I bought her one. After some discussion we went for a private dance. We went back to a semi private room and she proceeded to do a strip dance for me.
Not long after she pulled out her big cock, I was on her sucking it. She said that wasn't allowed but she never stopped me. It loooked like a few people in the audience could see what was going on too! After a while of this I ended up cumming on the floor. So I went to clean up. After another drink we went back to my hotel room for a while. She attempted to fuck me but she was way too big. She wasn't very nice so she didn't end up staying long.

The next night I went back to Papa Joes and ended up taking home a cute black tgirl. We hit it off and I spent a few nights with her.
Here are a few pics of my second tgirl ever.

shos2.jpg
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[Rockheart]

My first Thai Ladyboy experience was in 2007 in Bangkok. It had been a number of years since my first experience in New Orleans and since I had been dabbling in tgirl photography, I had been with a number of asian ladyboys in Canada as a result. However the Thailand ladyboy experience is totally different. The few ladyboys in Canada at that time were few and far between, Thailand was totally different.

I went with a bunch of guys I worked on a website with. They were all very experienced in Thailand so they led the way.
The first day in Thailand we toured the temples and ruins north of Bangkok and it was over 40 degrees Celsius.
I was jet lagged already but the day tour did not help that much.

After i went to my room at the Dynasty Grande to freshen up and we all were to meet for dinner at the Marriott hotel. So at the Marriott we had their amazing buffet and drank lots of wine. After they took me over to Guess Bar which was new at that time. It was still at it's first location on Soi 1. I barely remember how we got there and couldn't even remember where it was until I looked back on this forum.

So we got inside and I sat at the bar and got a drink. There was about a dozen hot ladyboys there and it was nothing like I had seen before.
Eventually the other guys got the ladyboys to drag me over to the couch as I was quite shy about the whole thing. Soon i was on the sectional couch buried in ladyboys grabbing at me. My hands were roaming and feeling all sorts of great things. As the smoke cleared, I was making out with one, so we had a match. Soon we decided to go upstairs for a short time, which was also a first time. It was a little embarrassing with all the guys cheering me on as I went upstairs.

Once in the room we got down to business. She was a hot ladyboy with a really nice lookng cock and some juicy tits, but I have no idea who it was.
We sucked and then I fucked her in various positions until she was riding on top of me. With the jet lag and busy day, I was soon falling asleep.
There is worse ways to fall asleep than having a ladyboy riding your cock but it was a little annoying for her.
I only dozed off for a moment but woke up when she stopped and asked me if I wanted to get fucked. I looked at her large cock and said no, it just looked too big.
We then both managed to cum, then showered and went back downstairs, again to jeers and comments from my friends.

After that they took me to Obsessions in Nana where the other guys disappeared and left me and another new guy at the mercy of this bar.
After hours of drinking and having fun with ladyboys I finally left with 2 ladyboys that came to my room.

I found some old pictures on this forum showing the old Guess Bar location and ladyboys. It is probably one of the ladyboys in the picture but I don't know which one.
Also attached is the two ladyboys I took from Obsessions on my first night in Thailand.

[bernipes]

Thanks Rockheart for sharing your exeprience. Sepcial thanks for the pictures as usual
You life looks like a comic with all illustrations included

[Escierto]

I had never given transgender women a thought until about ten years ago. I had been chatting with a Filipina on a defunct web site that allowed people to chat and watch each other’s cams. Over a few months I got to know this woman until she confessed that she was a ladyboy. I didn’t believe her so she showed me. She thought that I would be mad at her and reject her but in fact, I was mesmerized. Yes, I wanted her. All of her.

I never met her in person unfortunately but I helped her get a sari sari store running and she was able to make a better life for herself.

It was many years before I finally met a transgender woman in person, a Filipina from Mindanao that I arranged to meet in Hong Kong. We spent a week together and although our relationship did not work out, I loved being her bottom. She had never been top before so she enjoyed topping me 19 times that week. Good thing that she did not have a big one!

This past December I spent three weeks with another Filipina transgender woman and it was wonderful. We had been chatting for months prior to this and I was never really sure about our relationship. Neither was she but after we met in person and spent some time together, we knew that we were committed to one another.

[Rockheart]

Nice story Escierto.
Those Filipina ladyboys can be very enticing.

[bernipes]

I had never given transgender women a thought until about ten years ago. I had been chatting with a Filipina on a defunct web site that allowed people to chat and watch each other’s cams. Over a few months I got to know this woman until she confessed that she was a ladyboy. I didn’t believe her so she showed me. She thought that I would be mad at her and reject her but in fact, I was mesmerized. Yes, I wanted her. All of her.

I never met her in person unfortunately but I helped her get a sari sari store running and she was able to make a better life for herself.

It was many years before I finally met a transgender woman in person, a Filipina from Mindanao that I arranged to meet in Hong Kong. We spent a week together and although our relationship did not work out, I loved being her bottom. She had never been top before so she enjoyed topping me 19 times that week. Good thing that she did not have a big one!

This past December I spent three weeks with another Filipina transgender woman and it was wonderful. We had been chatting for months prior to this and I was never really sure about our relationship. Neither was she but after we met in person and spent some time together, we knew that we were committed to one another.

Nice!

Thanks Escierto for sharing your story

[Ghostbxl]

I had never given transgender women a thought until about ten years ago. I had been chatting with a Filipina on a defunct web site that allowed people to chat and watch each other’s cams. Over a few months I got to know this woman until she confessed that she was a ladyboy. I didn’t believe her so she showed me. She thought that I would be mad at her and reject her but in fact, I was mesmerized. Yes, I wanted her. All of her.

I never met her in person unfortunately but I helped her get a sari sari store running and she was able to make a better life for herself.

It was many years before I finally met a transgender woman in person, a Filipina from Mindanao that I arranged to meet in Hong Kong. We spent a week together and although our relationship did not work out, I loved being her bottom. She had never been top before so she enjoyed topping me 19 times that week. Good thing that she did not have a big one!

This past December I spent three weeks with another Filipina transgender woman and it was wonderful. We had been chatting for months prior to this and I was never really sure about our relationship. Neither was she but after we met in person and spent some time together, we knew that we were committed to one another.

Filipina girls can be really Nice experiences

[Escierto]

Yes, I wish that I was back there having some more nice experiences with her. They will start allowing foreigners with long term visas back in the country on August 1 so that’s progress. I don’t think tourists will be allowed until the vaccine is available.

[bernipes]

Yes, I wish that I was back there having some more nice experiences with her. They will start allowing foreigners with long term visas back in the country on August 1 so that’s progress. I don’t think tourists will be allowed until the vaccine is available.

Yeah ... hope everything will be done soon. For all reasons... Especially Ho and the beautiful views also

[Chaddonald]

Just wanted to say thank you all for posting your first times. I myself have never been with LB so it's very interesting to read your stories. Thanks again! Will definitely be checking this thread more often.

[bernipes]

Chaddonald That's basically why i opened this thread

Never had any experience also, and with this COVID Shit it will not be tomorrow ...

But yeah you are right, Thanks again to everybody who posted the stories here

Hope we'll can post ours soon

[solomon]

I have always been attracted to feminine beauty. About 15 years ago that attraction started to include trans women as well. In 2008, I was living in New England and had to travel to Toronto for business several times between then and 2010. At the time, they had one of the first transgender clubs in North America in Goodhandy's. I went several times and had my first experience with a couple of girls from the Club. My first two experiences were with Nikki and Ashley. I saw Nikki several times after that first time. Very educated and smart girl. First time I saw her, she had just started hormones and has grown into a beautiful woman.

nikki.jpg ashley.jpg

As time went on, Providence had a really cool club known as the Dark Lady that had many transgender women in it. My first Ladyboy experience was with a beautiful girl named Lily that I met there. Beautiful Thai girl, but to her it was all about the business.

lili2.jpg

In the 2014 and 2015 timeframe, Providence also had a Transgender Strip Club known as the Satin Dolls. It was a a genetic girl club in the day and became a transgender club for the night shift. Met another beautiful ladyboy there, but she was from Taiwan.

GrandopeningSatihyn2.jpg V__4BD7.jpg

Since then I have enjoyed the company of over 25 beautiful transgender women in various stages of their transformation. Love transgender women, because they seem less crazy than their genetic girl sisters. Also because they do not take their beauty and femininity for granted. They always want to look perfect and beautiful.

[Rockheart]

Nice story. Ashley is still around.
Goodhandy's just closed for good due to the current situation.

[solomon]

Nice story. Ashley is still around.
Goodhandy's just closed for good due to the current situation.

The fate of all of these clubs is in jeopardy at this point.

[bernipes]

I have always been attracted to feminine beauty. About 15 years ago that attraction started to include trans women as well. In 2008, I was living in New England and had to travel to Toronto for business several times between then and 2010. At the time, they had one of the first transgender clubs in North America in Goodhandy's. I went several times and had my first experience with a couple of girls from the Club. My first two experiences were with Nikki and Ashley. I saw Nikki several times after that first time. Very educated and smart girl. First time I saw her, she had just started hormones and has grown into a beautiful woman.

nikki.jpg ashley.jpg

As time went on, Providence had a really cool club known as the Dark Lady that had many transgender women in it. My first Ladyboy experience was with a beautiful girl named Lily that I met there. Beautiful Thai girl, but to her it was all about the business.

lili2.jpg

In the 2014 and 2015 timeframe, Providence also had a Transgender Strip Club known as the Satin Dolls. It was a a genetic girl club in the day and became a transgender club for the night shift. Met another beautiful ladyboy there, but she was from Taiwan.

GrandopeningSatihyn2.jpg V__4BD7.jpg

Since then I have enjoyed the company of over 25 beautiful transgender women in various stages of their transformation. Love transgender women, because they seem less crazy than their genetic girl sisters. Also because they do not take their beauty and femininity for granted. They always want to look perfect and beautiful.

Thanks solomon for sharing your story !