Your First Time

[soju]

Used to travel with a mate and we would monger in Cambodia and Thailand but only took girls. My buddy made it well known that he didn't like ladyboys so I kept my curiosity to myself. Back in 2011 I took an extra week of holidays and when my mate went home I headed straight to Pattaya. I booked a room at the Queen Vic on Soi 6 with the intention of heading to the Horny Bar (now sadly long gone) and Pooks. After mandatory SSS I made my way to the Horny Bar and saw Ae and May out front but I lost my nerve and walked past it to Beach Road.

Couldn't believe it but I was really nervous... actually surprised myself I was so nervous. I had been with many hookers but in this situation I was a total newbie. Decided to walk back again but the Horny Bar was too busy so I kept on walking past. Dropped into a girlie bar for a drink but really wanted to try a lb. So I left and made my way down to Soi 7 as I had heard good things about Anaconda Bar. It was actually tucked away a little off of Soi 7 but I did the same thing and walked past it. Still nervous as shit even my damn hands were sweating. Was pissed off at myself so I said fuck it and went back. Sat down at a table and invited a girl who went by the name Ying over for a drink. She sat down slipped me the tongue and my nervousness vanished.

Took Ying back to my room that night. Back in 2011 you had to climb the fire escape to enter the Queen Vic after 11pm. They even had a security guard who sat up there on a chair and took the girls' IDs 555. Anyway, Ying turned out to be fantastic. She licked me everywhere and when I thought she would stop she kept on. Two or three times I remember thinking surly she would stop now but she didn't. I was lucky, my first time turned out to be a wonderful experience.

Anyone else? How was your first time?

BTW later that week a went to Horny Bar and took Ae and later May... good times.

[Rockheart]

I guess i will describe 2 first times, in the USA and then my first Ladyboys in Thailand.

Way back at the beginning of the internet i was interested in shemales but had never met any before.
I was a member of the few website there was at the time and shemaleyum.com was one of the first.
Anyway i was on a business trip to Atlanta and decided to take a week off after and visit New Orleans with the thought of trying my first TS.
The first full day in New Orleans I went to a Saints game which was my first NFL match. Then later that night i headed down to Bourbon st.
On Bourbon st. there was 2 places i was interested in. First was Papa Joe's which was a shemale strip club which no longer exists.
It was quite the attraction and was full of curious tourists.Meghan Chavalier and some other well known tgirls worked there dancing.

The other place was a gay bar called OZ.

https://www.ozneworleans.com/

A shemale named Stephanie Williams did shows there and she happened to have one of the few TS sites out there.
So i was hoping i could maybe meet her and/or some of her friends that were on that website.

http://www.gayamerica.com/stephaniewilliams/

Anyways I ended up at Papa Joe's that first night and started watching the show. There was several girls and most had implants and were not crossdressers at all. So this place was legit. Shortly Tracy came to sit with me and she would be my first. She was not the greatest looker but I wasn't too picky at that moment. She talked me into a private dance, so we went into the back into semi private area for my dance. Tracy started to gyrate and soon she was pulling a huge cock out of her panties.
Eventually I ended up sucking it and pulled out my own dick and at one point i looked up and noticed that a couple in the audience could see everything we were doing.
I kept going and eventually dropped one on the floor. After cleaning up in the back i went back the show and after than Tracy ended up coming back to my hotel.After some more oral she was ready to fuck me. I asked if i could fuck her instead but she said she was top only. She tried unsuccessfully to stick it in me but there was no way.
So she left and it wasn't the greatest experience ever but it was the first.
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A couple night later i ended up going back to Papa Joe's and met a really nice black girl named Shosona who was dancing when I got there.
She was really friendly and very cute so I ended up taking her back to my room. She was very horny and had a long cock.
We did some oral then i fucked her for around 2 hours or so, then I gave her some money and she left. About an hour later there was a knock at the door. Shoshona had come back with some Popeye's and wanted to spend the night. I had no problem with that.
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Now for my first time in Thailand was about 8 years later. In the meantime i had started producing porn for ShemaleYum.com in Canada and the USA.
So the opportunity came for a company trip to Thailand and most of the photographers and employees were there for fun and a little business.
So the first day in Thailand we went on the tour of Ayutthaya for the afternoon, then went to the Marriott near Nana for their amazing buffet.
After that they took us over to the original Guess bar on Soi 1 and we were just about the only ones there but there was about 10 of us.
Soon i was coaxed into sitting with some of the ladies and one ended up taking me for my first short time experience. I was amazed by the short time rooms as I had never seen anything quite like it, other than a sex hotel in Brazil. I had an ok time with some ladyboy but my jetlag was starting to kick in and i had gotten very sleepy.

After that they took us over to Nana Plaza and we started out in Casanova bar and i was sitting there talking to Buddy Wood who was new to the company.
Then we looked around and noticed all the other guys had disappeared. We weren't sure where they went so we went and looked in practically every bar in Nana to find them.
After not having any luck we decided to try out Obsessions bar. It turned out our friends had abandoned us in Nana so we could experience the full wrath of the ladyboy bars.
Now that the drinks were kicking in I was getting energized. Obsessions was a classic first timer experience. The guy that is the boss there was awesome and he was hilarious. He gave us the full treatment and got many drinks out of us for him and the staff. I suddenly had two ladyboys come sit on either side of me who turned out to be Odette and May. Buddy had one blonde ladyboy come to sit with him. The night was crazy and we drank in there for hours partying like rockstars buying ourselves countless drinks and buying drinks for pretty much everyone else too, meanwhile I was making out with and groping these two beauties. Eventually last call arrived and they said they would bring the bill and i had a little bit of a panic as I was worried how huge the bill was. They brought the bill and amazingly it was only about $100. A similar outing in Canada may have cost $600 or more so that was my first taste of how truly cheap Thailand was but not so much anymore. I had previously paid the bar fine for my two ladyboys and we headed back to my room at the Dynasty Grande. I had a great threesome with the two of the for about 3 hours, fucking them both a couple times. It was quite the wild night compared to back home, Bangkok delivered as promised.

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After that we went to Pattaya and i ended up spending the rest of the trip with Anne.
We got some old fashioned Thai pics at the mall and also a pic of her holding my cock.
A great first trip to Thailand, it really was a new first time...

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[soju]

That was a good read. Thanks for posting.
I can see why you spent some time with Anne, she is/was a real looker.

[soju]

BUMP!

Only Crag shared his experiences.

Come on you lazy buggers and man up...your first time with the third sex. The good, the bad, and the ugly.

[outlander5]

My first time was 3 yrs ago with a freelancer on soi bukhao named Nookei, talked on tf months before coming was nervous as shit but when we met i was surprised in the passion she showed from the first kiss ,we fucked right off the hop my first time receiving definitely wasn't easy as she was a little bigger in person but we had all night so we went out for dinner then stopped for quite a few drinks at the climax bar before heading back to my hotel!! The anticipation walking back was electric we made out everywhere nobody could see us it was like she wanted it as bad as me and man when we hit the room we had a solid 1/2 hr of foreplay before having a shower now as i was showering i noticed she saw my viagra and bam she eats a whole 100 mg pill shit if i ate half that my heart would explode and that would be my baptism by fire so while i fucked her nicely my recollection was her cock never softened all night by morning i was a ragged anne fuck doll, hate to think how many times but walking wasn't easy the next day!! I had know idea how much to pay her the next morning so i left 5000 baht on the table and said take what you want , she took 1500 gave me a kiss and said ill call you later get some sleep we'll meet some friends tonight!!
Now I know I made many rookie mistakes that night but never once did she take advantage of me or the situation !!