First Time with Lady Boy

[zanemay]

Last night, walking back to my condo con dio (alone) (or "with God" in Spanish I saw a figure in the distance on the lonely street. From the slender hips and her place in the shadows, I assumed this was a ladyboy. One of hundreds in Pattaya. With the barest notice, I patted my pockets to make sure my money was secure, and then thought about what snack I might pick up at the street market on my way. I forgot all about him/her/whatever.

"Hello. Where you go?" said a very feminine voice as I passed. I looked over to see a lovely Chinese face framed in a perfect Dutch cut. This was a girl.

"To my hotel. When I saw you far away, I thought you were a ladyboy."

"No ladyboy. Lady," she said.

I was impressed by this beauty. She spoke a little English and had a very nice manner. But as she held my hand, I wasn't convinced about the gender. Her hands were a bit big for a lady. I stared at her neck looking for an Adam's Apple. I thought I saw a hint of one.

"Are you a ladyboy? It's okay."

"Yes. Ladyboy. I think you not like ladyboy."

"Not a problem for me," I said. I had been interested in taking a ladyboy for awhile. Most of them are such Amazon gargoyles or just boys in dresses. They have no appeal to me. But on my last trip I would talk to a nice little she/he on Beach Road. She kept trying to get me to take her, and she seemed pretty nice, and more feminine than most. Anyway, I hadn't been quite ready for the experience. Now, because I love a great blow job, and because I one cannot maintain a prejudice over a long period of time towards this oh-so-common phenomenon, I had been wanting to see what one could do for me. "Only a man knows what a man wants," they say.

And this he/she was in a whole different league than others I have come across.

"I worked in Holland," she said. "Behind door." She meant she had gone to Amsterdam and had been on display in the famous red light district. That is big time for a Thai prostitute. She was something special. We talked for a few more minutes and I really enjoyed her. Her English was decent and she was very sweet.

Trying to pay her a compliment I said, "You seem like a lady to me. One hundred percent." I was surprised by the negative reaction, "No lady! Ladyman!" She did not want to be identified as a woman?

"Okay," I said, "you can come with me."

As we walked along, it was a little strange. She didn't try to hold hands with me like any other lady of the night. There was a slight undertone of discomfort on her part. I got the impression that she had had so many problems with men who wanted a real woman and gave her a problem once they understood that they didn't have one. In Thailand "big problem" translates into "did not pay." And of course they always have to worry about homophobics beating them up.

Back at the hotel, we sat on the couch and talked. She had a very sweet disposition and started to get a little affectionate. But now, unlike any other Thai lady, no kissing. I also began to notice another little anomaly - she was kind of hyperactive. She talked a little too fast, repeatedly apologized for inconsequential things and was just a little nervous. Paranoia? Drugs? Still, she was a beautiful little Thai Chinese girl with good manners and a sweet disposition and I was enjoying her.

The time came for her to shower and wrap up in the famous towel - the most reliable of all Thai customs. I was most extremely curious to see this one naked and when the towel dropped away I was very pleased with what I saw. She had told me she had been fixed and I saw now that they had done great work. At least superficially the pussy looked real, the tits were perfect and the whole package was fine as hell.

But I had a problem - I can't stand those damn silicone implants. I've had the experience before. They are too round and far too hard and with ladyboys they are really strange. They never had the experience of a young girl anxiously anticipating her development and looking at herself in the mirror every day to see how it was going. Instead of lovingly nurturing their breasts, ladyboys enter into contracts with doctors who painfully plant these foreign objects on them. Their tits are just possessions like expensive shoes. They show them on the street and invite you to touch them to prove they are more than stuffed bras. It's a travesty of things sweet and feminine.

But anyway, I was primed for the best blow job of my life. Of course I was skeptical that there could be a performance better than my expert girlfriends, but I wanted to see. Maybe there are tricks born of empathy and passion that would transport me to new realms! Okay ladyboy, do it!

Nothing! First, "You have condom?" Oh please! Words from hell when uttered by someone about to give you head. I tell her she doesn't have to do anything she doesn't want to and I will pay her anyway but I cannot finish with condom. After hemming and hawing she says, "No. I want make you happy." Okay, good, that's what we're here for!

With no kissing or preliminary affection, she starts out with a hand job. A rough, rough hand job. "Bao-bao (easy, easy)" I say, and she tones it down but it is still too fast and rough. I reach for the baby oil by the bed to apply just a little. My hyperactive friend grabs it away and slathers on five times too much. Meanwhile I am looking at those silicone rocks. This is not exciting.

After a bit she commences to suck, but sucking like someone who would rather be doing this with a condom. Tentative. Wary of drips. She is no better when she licks the balls. I've been through this before and I am shocked that I know what it is - just another bad blowjob. You pays your money and you takes your chances with ladies. But with ladyboys too?!

"Okay. Stop, stop kap. I cannot finish."

"Why!?" She was a little wounded, probably thinking that I am turned off by ladyboy.

"Nuai (tired), kap."

She is a sweetheart and I am sorry to disappoint her, but I think the situation suffered more from her excess professionalism than anything else. She had been a prostitute in the West and acted too much like one. She wasn't the same as her naive counterparts. She was nice but not loving. She was not interested in the future or being a girlfriend.

She dressed her beautiful self (This is a girl!) and left to retrieve her motorbike. I gave her 500 baht and "Chok dee (good luck) to you!" "Chok dee, kaaa!"

Disappointed, my high expectations in shambles, I have had my fill of ladyboys for awhile. This one was so exceptional I'm not sure what I learned. Not all that glitters is gold? Certainly. But still...there is the nagging question, isn't there? Maybe they do know something special?

[Big Kev]

Interesting tale ZG.

Not sure I agree with you that working in Holland is "big-time for a Thai prostitute". The ones I've seen there are usually skanky older babes that would be second teir talent in most BKK or Pattaya venues. I've almost gotten the feeling that they couldn't attract much business back home and somehow made their way to Amsterdam where there are fewer fresh little cuties to compete with.

[Guest]

Let me be the second, in a long string of posts to come, to say, "Interesting tale, Zane."

Honestly, to me, it is not intuitive that ladyboys would be better in the sanuk category. The only upside that I would imagine of them relates to the fact that more than a few fall into the tall stunner category.

Given ladyboys' biological issues and also the societal issues they've confronted over a lifetime, ladyboys are even more likely than typical BGs to be bad, weird mental cases. I've talked with a few, and they pretty much all are creepy.

Your post is probably going to scare some dudes who dismissed their suspicions during past encounters with "real girls," upon confirming a nice snatch. Your post points out that even that can be deceiving.

[pattaya127]

When i hang out with a few thai friends in pattaya, there could be usually 1or 2 ladyboys with them. i never found them weird socially, thouh I agree the switch from he to she may carry some psychological scars. They just acted like women, that's all. if only a little more self-conscious about their body, especially hair seems a great concern. Not talking about sex, but i've always been open-minded about any kind of people, plus a definite interest in nightlife characters and fellini movies, people on the fringe so to speak, and somehow if you open up to the human side, you can forget the freak aspect. Incidentally, I just saw in SF, the thai movie "Iron Ladies", about gays and Katoeys playing volley-ball. I went with a friend,and we argued after the movie if the actress playing the Tiffany's katoey in the team was a post-he or a born-she. i said he, he said she. Anyone knows?

[Guest]

Sorry 127. Haven't seen the movie, but I'll keep an eye out for it. Interesting.

Maybe I'll also do some first hand research to settle the argument you're having with your bud.

Go Barry! Duck the Fodgers.

[Guest]

I had a ladyboy years ago in Pattaya. At the time I did not know (really) and was told after the dirty deed was finished. My experience was great. She had a to die for body I am talking 10 here guys no BS. She had lived with a German millionaire and she was 31yo and cultured. she even fussed over me at dinner by being very attentive. In bed she felt like a real woman. Her vagina was tight and she loved giving head. I still have a several photos and wonder at the beautiful face and body. A very memorable experience for a straight guy (hey! how was I to know and I do not care)and wish I could see her today.

[Big Kev]

To vtombrown -- I have no problem with SFG finishing ahead of Dodgers, but PLEASE lord, don't let Bonds hit over 70!! I have a case of black label bet on this and was feeling confident right up until couple of days ago. He seems to get them in bunches and I won't feel safe until season is over and his total is 70 or under!!

As to topic of this thread, I've never done a lady boy (that I know of) and just can't get excited about the possibility. Don't care how good looking or talented the creature might be. On this factor, I guess I'm really quite conservative, some form of homophobe or something.

[phoenix]

Pattaya127: >Incidentally, I just saw in SF, the thai movie "Iron Ladies", about gays and Katoeys playing volley-ball. I went with a friend,and we argued after the movie if the actress playing the Tiffany's katoey in the team was a post-he or a born-she. i said he, he said she. Anyone knows? <

I saw it about 4 or five months ago, too long to rememebr that detail. But i really enjoyed the movie, and it did give a nice sense of what soem of the issues are for them in LOS. I went with Tuk, and she kept screaming with laughter (she obviously understood all the jokes that weren;'t translated in the subtitles)

[pattaya127]

quote:

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Originally posted by Big Kev:

As to topic of this thread, I've never done a lady boy (that I know of) and just can't get excited about the possibility. Don't care how good looking or talented the creature might be. On this factor, I guess I'm really quite conservative, some form of homophobe or something.

---

I think the guys who have been unknowingly (but happily) with ladyboys can be counted in the 10 000s. We always think of katoeys as more like freaks, but there is a whole world out there of perfect women who used to be men. Actually, can someone confirm that the last Miss Thailand, or last year's, was a katoey, and the judges learnt of it after the election? The article i read said that one judge cried foul and another just TITed him, saying who cares what gender, she won clean and square. Maybe it was only a regional contest. I'd love to think it was the national one....

[Guest]

Can't quite remember about the contest, but I think it was a regional one, or an off-brand national one. I remember reading a quote in the Nation newspaper where a judge or sponsor was saying that the ladyboy had an "unfair advantage" in the beauty contest. Thought that was pretty funny and ironic.

Good luck Big Kev. But, I hope you've recently started setting aside a little money each week, so the Barry bet doesn't nail you too hard. Ouch. Did you say a CASE of Black Label? Wow, imagine how much BG sex that equates too? (Sorry, I shouldn't have even brought that up. )