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Red Light District Guide

How to find LadyBoys, Shemales and Transvestites in the Red Light District


If you are interested in an experience with “a little something extra”, Amsterdam should certainly satisfy your curiosity: elsewhere in this guide, we have discussed how easy it is to experience different sorts of women in the Red Light District, varying in age, physical size and race. In the case of ladyboys, however, you may well be somewhat nervous about exploring this particular kink in human sexuality.

Luckily, few things could be easier than “window-shopping” and you can take as much time as you want, whether you need it to build up your courage or simply to work out which would most appeals to your sensibilities.

What is the difference between LadyBoys, She-males and Transvestites?

The terms “ladyboy” and “she-male” can be used pretty much interchangeably, although the ones from South America prefer to refer to themselves as she-males and the ones from South East Asia call themselves ladyboys. Both usually have feminine features including a fair amount of plastic surgery including, most obviously, substantial breasts.

Of course, if you can look past these eye-catching appendages, you will notice that they often also have very fit masculine physiques and this is very much part of the appeal for aficionados. Ladyboys and she-males pretty much always still have their penis – and, by that, I mean it is still attached, not sitting in a jar in their living room. You could call them “pre-op / pre-operative” but, in reality, only a small minority have any desire to take that final transformative step – most are very happy with their penis and aware that it is an important part of why their clients pay to spend time with them.

Post-op ladyboys and she-males, with artificially constructed vaginas, would usually just be called “women”. There are quite a few of them in the Red Light District, trading as women, which is their legal right, and very few people would ever guess their secret.

She-males and ladyboys usually live as females in every aspect of their lives. For the most part, their cultures are more accepting of men living entirely as women than a normal gay lifestyle. It is simplistic, but they find the idea of someone being “secretly” gay to be more intimidating. Many have theorised that, if raised in a more open culture, many she-males and ladyboys would, instead, choose to remain regular gay guys. In the case of Thailand, an added incentive to live as a ladyboy and, in particular, to get breast surgery before the age of 18 is that it allows you to avoid the otherwise compulsory military service.

A transvestite is usually a man who enjoys sometimes dressing as a woman but usually lives the rest of their life as a man. They can be straight, gay or into other transvestites. There are not many in the Red Light District, you would be more likely to find them in nightclubs and specialised bars, but you do occasionally see them in a window, usually in the same areas as the ladyboys and she-males, and usually at night which suggests that it is often a “hobby” experience for them, rather than a career move.

How to Spot Them

Some ladyboys and she-males are extremely convincing, especially to the untrained eye. The convention is that they should have a blue, rather than red, light in their windows and this is accepted as sufficient disclosure. It is not that they particularly want to con anyone but the feeling is that, if an innocent tourist wanders in, pays his money and then discovers a cock where he did not expect one, that is his blunder, the sex worker gets to keep the money. Obviously, this does causes arguments on occasion but, if the police get involved and they can see the blue light in the window, they will tell the bewildered client that it was his mistake.

Incidentally, the coloured lights are a informal convention, not a legal requirement, it is not unknown for ladyboys and she-males to work without them, particularly if they are given a room that does not usually cater to ladyboys. Some have the light but use various ruses to obscure them, sometimes with the curtain, but most prefer not to attract trouble and know that, very often, there are more customers interested in them than the “genetic females”.

Time of Day

You can find them Ladyboys and She-males in Amsterdam’s main red light district at pretty much any time of the day. The ones who work in the day tend to be more established and to have built up a substantial clientele of regulars, often office workers, who pop by during the working day – boardroom stress is a terrible thing.

There are substantially more she-males and ladyboys at night and they particularly tend to work right through the night, right up until 5 or 6AM. This is because male inhibitions tend to be much lower in the wee hours, and many men are a lot more likely to indulge this hidden part of their sexuality at that time, particularly after a few drinks.

What Will They Do?

Well, you are the customer, it is very much up to you. Although they adopt feminine features, it appears that for many men ladyboys and she-males are a way to explore their attraction to men without facing up to the possibility that they might be, just a little bit, gay. Some customers just want to receive oral sex and perform anal sex on them, as if they were women, but a far higher proportion of clients want to be the one to perform the oral sex and to be the ones getting fucked.

Some she-males and ladyboys will encourage the client to be direct about what they want, others will just let the client get there in his own time, with it sometimes taking several sessions before the client will timidly admit that he would prefer to be on the receiving end. These sex workers have heard pretty much everything so, really, be honest about what you want.

Regardless of the role-play, no ladyboy or she-male needs or want trouble, so, you really do have complete control over the situation. If you are uncomfortable with the direction in which things are going, speak up and say so. As long as you are paying for their time, you get to dictate the speed at which things move and the vast majority will be very happy to provide their service to you in any way which makes you happy.

This is a delicate topic to bring up but, if you would like another person to perform anal sex on you, it is only polite to ensure that you are extremely clean down there. Think logically and be sure, before you go window shopping, that you do not actually need to go to the toilet. It might even be an idea to get an enema – they are also very good for you.

Don’t Be an Idiot

Always treat transgender sex workers with respect. All of them have encountered hardship and prejudice in their lives, usually because their persecutors are so deeply in the closet that they can only express hate. They do not need another serving of bullshit from you. If you have unresolved issues about your sexuality, do everyone a favour and stick to online porn. Visiting a transgender sex worker certainly could answer a lot of questions for you, but you should do so in a spirit of openness, respect and fun.

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