The Realities of Sex Work

In various crossdresser forums on various websites, I often see many crossdressers express their desire/fantasy of being an escort/sex worker/prostitute/whore. It makes sense. What way to feel more like a woman than to be paid to act like a woman in the bedroom? The idea has been romanticized since 1990’s Pretty Woman. That is what we as crossdressers want to be, after all, PRETTY. We want flawless makeup, tight little bodies, and designer clothes that cost a month’s wages. We want to stroll through the streets and hotel lobbies, confident and secure, ready to please and pleasure, walking away with a wad of cash.

That is not quite how it works in the real world, regardless of gender identification. I have done sex work off and on for years, and actually got into it by accident. In this entry, I’ll go through the dos, don’ts, costs, and all the others regarding sex work as a crossdresser.

Starting Out

To begin, there are some things you will need to do. First, figure out which website you are going to post your ads from and go through their verification process. Do this in “male mode”. You will need to provide a facial shot and a copy of your driver’s license. Use your “girly email” as a contact for this.

Next, you need a phone number. I don’t use my normal cell number. I use Google Voice. This is free, and it allows telephone calls and text messages.

Lastly, you will need a place to work. I do not work out of my home for various reasons. I will work out of a motel or a hotel. Check into wherever you work in “guy mode”.

Advertising Yourself

The old saying is “It pays to advertise”. You, as a sex worker, are a product, a commodity. You need men to WANT YOU. You need to come across as something a little more than all the other girls. On the site I work off of, the girls are all trans as opposed to crossdressers, so I have some very tough competition.

The best way to overcome this is to have professional photographs taken of you. When I had mine done, I went and got my makeup professionally done. I wore an elegant black dress and looked rather classy. I had body shots and some mid-shots taken. The professional eye makeup really comes across strong. These look so much better than cell phone selfies taken in dirty motel mirrors with bad lighting. If you want to be somebody’s fantasy. LOOK like their fantasy.

Your Ad and Pricing

After you have your photos (mine took a week or so to get back), you are ready to post your ad. Be creative, be sexy, play it all up! Imagine you are a phone sex operator and just let the words flow! Be sure to mention any specific acts you will or will not perform. Mention that you have a safe, clean, and discrete in-call location. Are you willing to travel for outcalls? If so, tell how far you are willing to go and any travel charges/deposits that are involved.

Always state that you are accepting donations. Charging for services is illegal, so you are accepting donations for time only. I accept cash, Cashapp, or Zelle and I make that clear. The timeframes you are working with are quick visit (qv) which is less than a half hour, half hour (hh, hhr), and hour (Hr). The reality of men in this aspect is 1) they are bargain hunters, 2) they will cum quickly. If you are creative on your pricing, you can get yourself a few extra dollars. The half-hour package is where you are going to make your money. I’ll price a qv for 100 and a hhr for 150, and an hour for 200. Clients will think they are getting more for their money by going with a hhr instead of a qv when in reality they will be in and out within 15 minutes regardless. Congrats girl, you just got an extra 50 bucks! If you are texting with a client and they are not sure how long of a visit they want, get real sexy and tell them all the things you want to do to them. Be long and descriptive. 9 out of 10 times, they will take the higher priced package. As a general rule, I am always open to negotiation, within reason. Will I do a full hour for 80 dollars? Not on your life. I will, however (depending on business), do a half hour for 80 dollars knowing he will be out the door in less time than that.

What To Bring

First off, make sure you give yourself an enema before you start off your evening. I don’t think I need to go into detail as to this. After that, make sure you have your butt plug in. If it is going to be a busy night, you will thank me later.

I make sure I have condoms and lube in a nightstand drawer AND in my purse. It pays to have them in each in case you forget as you head out the door. Another thing I have is lube injectors. These can be purchased online or at adult toy stores. I make sure I am lubed up prior to meeting a client. It is less messy and makes the experience more natural.

As for clothes, I make sure I bring an evening dress, a miniskirt and a top, high heels, a variety of stockings and pantyhose, and ballet flats. Sometimes a client may have an outfit request. If so, I am ready. Ballet flats will be a savior. I have had too many times where I had to park in the far end of a parking lot or a half block away from someone and walk across a terrain that no human was meant to cross. Now try that in 4-inch heels. No? Try to explain how you broke your ankle.

Other things I will have in my purse besides condoms and lube are my driver’s license, debit card, 20-40 dollars cash, lipstick, and sunglasses. The license and bank card are in a pocket all by themselves, the cash is in another pocket, and everything else is in the main part.

Other Odds and Ends

I have found that most of my clients are either bi-curious or first timers. The reason for this varies, but that has been my experience. I’ve learned over the years how to talk with and deal with “virgins” and it has helped me immensely.

As a crossdresser, I cannot charge as much as a trans sex worker, but that does not mean I have to price myself as bargain barrel. Never accept a lowball amount. If somebody tells you they can find something better for 40 dollars, power to them, let them go and find it.

Always be clear with your limits. I have some things that I will flat out refuse to do. I also like to do things that some girls will not do. Foot fetish seems to be something that quite a few people ask for. I have no problem with that! I am not naturally domme, but I will adjust to the role to make the experience enjoyable.

Safety, safety, safety! If I have a client, I always make sure somebody knows. I will text in and text out. This is especially important for outcalls. Do not EVER go someplace without letting somebody know where you are going and the contact number the client provided you.

I have noticed that there are busy times and dead zones. Mid-afternoon, the after-work hour, and 3:00am tend to be the busy hours. Be ready to go. Keep in mind what your break-even amount is. By the time I rent a room, get my makeup done (if I don’t do it myself), and purchase whatever supplies I may need, I’m looking at spending anywhere between 100-250 dollars. Calls will vary from zero to ten per day. On average, I’ll hit above my break-even amount with 3 calls.

It is important to remember that as a crossdresser, we are a niche market. I know that I will never be able to support myself on sex work alone, and I am fine with that. There is an ebb and flow in the desire for a girl like me. I am not everyone’s cup of tea. If I am their cup, I make damn sure they enjoy the flavor.

Tags: crossdressing, featured, sex work

Category: crossdressing