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