Like a virgin
My current little sweetie is incredibly shy, and nervous about doing anything too adventurous. I really do like her, so I’m being cautious. But she really is, I’m sure, a virgin. I think at some point it will be time for a particularly large dollop of KY, but I do like a neat, tight, tiny little hole to play with. I was unwise enough to mention this to Sargent Shameless the other day, and as a response he sent me the following.
I expect the Captain will write something at the end of this article. The fact that in this here blog I am just a Sargent does not mean I feel less authoritative than the Captain about all aspects of ladyboy warfare. So, today I would like to talk about ladyboys’ first sexual experiences and let’s face it: the fact that I, unlike the Captain, don’t live in Thailand means that when a ladyboy falls into my lap (at 18 years of age or older definitely) she probably has been passed around quite a bit among the natives, the expats and the sex tourists.
Yet, more than a few times I have been with ladyboys who said I was their first. What could they possibly have meant?
The first possibility is that they literally were virgins and I was the first man to anally penetrate them. This is highly unlikely and not many have tried such a lie on me. Becoming a ladyboy invariably involves some degree of gay experimentation in adolescence and boys being boys a sweet accommodating girlie ass does not likely go unporked through prep school. If the Thai prep school studs do not get it first, it is highly likely that their older countrymen who are cunning (and btw much more predatory than the expats) will buy, cajole, or force their way into an effeminate boy’s backdoor. In brief, by the time the girlie boys reach the ladyboy bars and seafront boardwalks, the chances of them being virgin are next to nil and, even if they are, it would by definition all be over after the first full-service customer.
Having said that, I may have on a couple of occasions been the first to break a sweet ladyboy’s rosebud. It is a fact that some ladyboys refuse anal sex under several pretexts. I myself have been told my cock is too big, it is against their Buddha, they have diarrhoea, or they were saving it for their true love. Most of the time these were excuses to avoid the pain or subservience of taking big farang cock up the poop chute. Being the creative type, on such occasions I satisfied my lust in different manners but I also managed to persuade a few of them to surrender their treasure. I knew most were lying about being virgins in the first place, but a few (who were not bar workers or streetwalkers) may have been.
With a greater degree of certainty, I can say that I have made it possible for several ladyboys to lose their virginity as tops. Again, some may have been pretending, but I believe a few never had a shot at topping anyone as nearly all Thai men and many farang consider it not macho to allow insertion and also ladyboys like to live up to their female illusions by being strictly passive. I remember a ladyboy who had worked in KC3 for a couple of years telling me she was a lady and would not be able to top anyone, but after I proved her wrong she saying with what sounded like genuine satisfaction how good and easy it was.
And even with greater certainty, I think that by “first” the ladyboys were saying that I was their first farang. In fact I am pretty sure this was the case as, on most such occasions, I had met them in non-tourist venues, and nothing in our interaction indicated they had been with tourists or expats before. I like to believe this was what they meant by being their “first.” But as regards getting to ladyboys first, the Captain with his decades on the prowl in Thailand is probably the leading authority on the subject. The final word is yours, Captain.
A ladyboy can be whatever you want her to be! They are after all living a life of illusion. I would hesitate to say that ALL ladyboys tell you what they think you want to hear, but it’s a fair bet that those working in a commercial setup will. There is also, as you rightly say, those who are afraid to do it because of the pain or the risk of physical damage, or who may be recuperating from a previous log entry, or simply have a dose of the runs; the latter, with Thailand’s spicy food, being a non-infrequent condition. 
But, Sarge, a little visual inspection, and possibly a cautious fingertip, will give you a pretty good idea whether or not your beloved of the moment is joshing you. The back door to paradise is surprisingly small. Despite what many people seem to think, it was not designed to take a big cock. A genuine ladyboy virgin will have a very tight little opening. It will look small and smooth, with minimal puckering, and the inserted fingertip (or, better, tongue) will detect the tight little ring of muscle that is the sphinchter. Once our ladyboy friend has acquired a taste for being rogered, the appearance of this gorgeous little hole changes. The puckering becomes more evident, the opening takes on an appearance akin to a tied balloon, and sometimes you begin to see tiny little bobbles (or worse) where the skin has been stretched or damaged. As for the ease of entry, with the more experienced girl and a spot of lubrication, it becomes nearly as easy as vaginal sex. I have seen countless ladyboy bottoms up really close and intimate, and I’m pretty confident I can spot a virgin (or near virgin). As to being a virgin at the other end of things, all I can say is that it only hurts the first time! And those who decline, usually for purely macho reasons, are missing out on one of life’s great experiences. Forget the conventional squeamishness. You are with a girl who has a cock. The rulebook goes out the window.
- Captain Outrageous
Posted: September 6th, 2011 under Uncategorized.
Tags: The ladyboy experience
Comments
Comment from PeterB
Time September 8, 2011 at 4:07 pm
Need to make sure they take a good enema before you stick anything up there. Nothing worse than pulling out and seeing the end of your dick has changed color. Even if you wear a condom. I had a real bad one when I was in Bangkok in April, and I was fucking a ladyboy in the ass and I triggered a dose of diarrhea. I was wearing a condom at the time but even so I felt like throwing up.
Comment from Wandering Wonderer
Time September 13, 2011 at 2:25 pm
I cannot do it with a ladyboy if i see she has a dose of piles. i had the sweetest little thing in my hotel room when i was in phuket during the summer and she had this small extrusion sticking out of her ass, and my dick went limp. couldn’t get it up again. that was a waste of money. my experience with lbs has been limited so far. i did have a smilar experience a while back, but not such a bad one. i suppose its an occipational hazard. but i wonder how many of them suffer in this way? i feel sorry for them, getting piles at such a young age.
Comment from Mike
Time September 14, 2011 at 10:12 am
Nothing like a good tight arsehole to get into! Beats a pussy any day. Need plenty of jell though. Funny thing is that even the smell of KY can get me going thse days. I was in my local pharmacy (in Perth) buying some medicine for a cold when I got a strong whiff of KY and straight away got a stand on because it reminded me of being with katoys in Bangkok.
Comment from Rigid 1
Time September 15, 2011 at 8:47 am
I dont mind admitting that I have been fucked many many times! As long as nobody knows my name! I didnt know what to expect the first time we all wonder what it would be like but nothing can prepare you. my first lb had a very stiff cock quite big but not a monster. i had that night taken her from a bar at nana and we were in the majestic hotel. she asked me if i wanted her to fuck me and i thought right its now or not. so she put some k-y on her cock and pushed it up me. she wore a condom. it felt really painful. not at first but as she got further up. but she was gentle really and she only had to thrust for a minute or two and then she pulled her cock out took off the rubber and cum over my ass. Her cum felt nice and hot and she rubbed it in.
Next morning was a little bit sore but not much so I took her for two more nights and we did the same. When I got back home to Brisbane I couldnt get her out of my mind and I couldnt wait to be fucked again. I thought of getting into the gay circuit just so I could have that again but I chickened out when I went to a gay place I just couldnt face it.
Then after about four months I got the chance of a 1-year contract in Hong Kong, and now I get to Bangkok every month for a long weekend. I go to Cassanova in Nana and sometimes a freelance on Sukhomvit. If I don’t know the lb I ask if they have a big cock and can they fuck me. Funny I dont feel shy about asking that! I have had two really big ones but mostly average size I suppose. But I learned to take it right up as far as it can go and it doesnt hurt anymore just feels as if Im going to burst! I lay on stomach or on back. First couple of times on stoamch as I was shy about looking at her but then I found laying on my back with a pillow underneath I could watch her face as she cum and that I found really something! Also like them now to take off the condom just before she cums and cum over my face.
Captain you said lbs are addictive! You are right! Sometimes I am in Hong Kong and trying to work but all I can do is look forward to my next trip and my next fix! Hoping to take another 1-year contract in Hk.
Comment from Sparky
Time September 16, 2011 at 12:33 am
That addresses sevreal of my concerns actually.
Comment from jerry can
Time October 7, 2011 at 10:21 am
First time I ever got fucked was a few years back, about eight years I guess. I took a ladyboy from one of the King bars on Patpong. Not a LB bar, a girl go-go bar, and they had a couple of LBs in the background. Anyway, the one I took was not very tall but she was wiry. And when we got in the short-time hotel she took off her clothes and her cock was also wiry! A lovely curving one, very strong. We went in the shower together, and I turned my back on her and she put her cock up me. It all seemed so natural. It didn’t go up very far, but she was fucking me and I was pulling at my cock. She pulled out and I turned round and watched her as she shot all over the shower floor. The sight of that made me cum too.
We came out the shower and dried off and laid down for a bit, then her cock got hard again. This time she took a tube of KY from her bag and put a great dollop on her dick, and then with me face down she fucked me again. She got up further that time. It didn’t really hurt, only when she tried to go too far up. Then she pulled out and I rolled over in time to swallow her cum.
Next night I went back and took her again, and this time I tried kneeling over her while she lay on her back and put her cock up me. That was nice too, but I really liked it when I was underneath and she was in control, because I liked her feel her moving in and out.
For anatomical reasons no doubt, a cock can only go so far up without being painful. I have done it with many ladyboys since and although I like sucking cock too, it is being fucked which really does it for me. As Capt O says, once you have tried ladyboys, girls aren’t enough!
Comment from Bob
Time November 6, 2013 at 12:10 pm
The oppitomy of HENTAI
Comment from Nina
Time November 7, 2013 at 3:20 am
I have never been in Thailand, but I do admire the lady boys there for their dedication to their appearance and for their courage out in the field.
I am a lady boy myself (from Ecuador) and I live in Los Angeles and I go out and party with other T girls here. I have seen some Asian lady boys here in LA , cute and sexy too. I am petite, so we get along pretty well and we go out together sometimes and a few times I have ended in bed with some of them. They are a firecracker in bed and lots of fun! most of the ones I know have a small ricky but it does get hard for sharing. I am about 8″ and some of my lady boy friends will not let me go in their ginas because of my size, but they will suck me and pock me all nigh long! My close friens gigi has a 4″ ricky…I meet her in a parking lot in little Thailand here in LA…it was about 11 pm at night and she was just wondering around…while I was seating in my car making a phone call…as she passed close to my car I open my window and say hi to her, then she smiled a bit shy thinking that I was a girl….so I opened my door and pull my black dress up to show her the bulk in my pink panties. she was like ten feet away from my car but in about one second she was by my door asking me to show her my hard ricky! with a funny smile in her face she reached over the window and softly grabbed my tool caressing it…I could not believe that her hand was so warm despite the fact that she has been outside on the parking lot who knows for how long! I invite her to go around and get inside the car. I drove up the hill behind the small shopping mall where I found her so we could have some privacy. by the time I parked the car in the dark she already had my ricky in her mouth! I rolled up her skimpy silver dress and pulled it out of her…she had a small light blue34 bra covering a beautiful set of tits with perky dark nipples… I was sucking her nipples and she was stocking my Winnie…I reached for her candy bar…about 4 inches of hard and creamy heat. I bent down to suck it and stoke it taking my time while she was moaning and holding tight to my ricky…I reached her little hole with my finger wet in her juice to feel her …she was anxious and hot just like I was…but the location was not safe for car sex…I had already went a bit to far by taking her dress off and sucking her tits there by the side of the road…and I was about 45 miles from home. I proposed that we go to a hotel bit she was a bit scared to go anywhere and she lived with mommy there in little Thailand. She sunk her face in my ricky sucking and stroking me whispering that I come. I just could not hold it anymore, I come in her mouth with a warm rush that shook my entire body! I felt so relived and calm, while I was reaching for her as soon as she was getting up looking for something to wipe her cum filled face with. I give her a cleanex and went between her legs. I raised her legs to be resting in the dash board while I was sucking her and gentry stroking her little gina hole with my finger in and out.. I could her crying like a little girl as she could not stay still moving her little ass up and down! Then I felt the heat of her cum fill up my mouth ! I could not hold all the cum that was flooding my mouth ! I had to pull out from her to breath while I was still holding her squirting winner in my hand ! My mouth was full, my hand was full and she still was squirting all over the place! and she was moaning and screaming al this time! when I looked up to see her she was in a bath of tears and smiling at the same time! I her broken English she told me that she head no sex since she come back from Thailand about a year ago! We put ourselves together and I drove back to the parking lot where we first meet…it was like 1 AM…I ask her if I will see her again..and give her my phone number…she never called as of today and I have look for her around Little Thailand by east Hollywood. I do pull out her panties from my drawer and smell her perfume as a beautiful memory of that incredible night.. yes I kept her panties ! ha ha ha .
Comment from Nina
Time November 7, 2013 at 3:27 am
And I must say, this is a beautiful Site, delicate and classy.
The captain has great taste!
Comment from Soapy Joe
Time September 8, 2011 at 2:50 pm
I went with a lb from kc3 last year. we went to a short-timer in patpong near the bar. We went in the shower togethr and I put my cock up her arse, which was covered in soap. The soap got in the end of my dick and it really stung. Wont do that again.