What can an escort do for a cross-dressing man?

Escorting is a competitive business with many escorts firmly ensconced in the “service provider” sector. Looking at the escort advertising sites you see hundreds of pretty girls working very hard to provide escort services to a pool of potential clients. Finding escort clients and holding the line on escort rates is challenging especially when more and more girls are coming into the market.

by Hannah Jay

“Veronica” is a Women’s Studies graduate from a metropolitan suburb of mid-sized American city.

“I’d always been intrigued with the idea of escorting and I went on my first dates when I was in college. I pretty much put an ad up for outcall services as a dare to myself. I’d been studying what progressives like to call “sex work” for my graduating thesis and I thought it would be more authentic if I at least tried escorting.”

“I have to say my first couple of escorting dates were really awkward. I was more worried I had been set up on a police sting or that the clients would be creeps than I was about actually doing the job. But it all got a lot easier when my third client took me out for dinner a couple of days after our first date and suggested that I might not be suited to the straight “service provider” role.”

“That client, as it happened, was very interested in trying cross-dressing. I’d heard of cross-dressing, of course – you don’t do Women’s studies without hearing a lot about gender identity. But, honestly, I thought it was a sort of gay thing. Drag Queens and all that.”

“Was I ever wrong. It turns out that the vast majority of male cross-dressers and cross-dresser wannabes are straight and many of them married. Their cross-dressing is pretty much a kink like any other kink.”

Veronica’s third client suggested that they try a cross-dressing date and that she spend a bit of time researching.

“I am a great researcher.” said Veronica. “I got on the web and I was just amazed. There is a whole world in cross-dressing. Companies make oversized ladies shoes and breast forms and butt lifting girdles, all in sizes large enough to fit men. There are forums and websites and there are even cruises where cross-dressing men and their wives socialize. And there are plenty of escorts who do cross-dressing dates.”

“What was really interesting, and what looked like a great escorting opportunity, is that men who like to cross-dress also like female supervision. At some point, this type of men want a girl to tell them what to do, what to wear, and how to do their makeup.”

“And, yes, it is partially sexual. At least it is for some men who are aroused when they are en femme.” said Veronica laughing.

“Now, escorts make their fees by providing companionship and, from time to time, that companionship can lead to consenting adults doing what adults do. But the key services an escort provides is confidentiality, anonymity and discretion. An escort’s real gift, in many cases, is giving a client a safe space to engage with the side of his personality which, for whatever reason, he does not feel comfortable with sharing with the other people in his life.”

“My third client was married and, after three years of marriage, worked up the courage to tell his wife that he sometimes liked to wear panties or a bit of lipstick. It had nearly cost him his marriage. He told me that while she was the furthest thing from a prude, his confession hit a giant panic button. Her first reaction was, like mine, “You’re gay.” which he certainly wasn’t. Her second was to forgive him and explain that she just couldn’t have anything to do with this side of him because she didn’t know who he was. They’re still married, by the way.”

“This reaction turns out to be pretty common amongst cross-dressers’ wives and girlfriends. As my Women’s Studies profs liked to point out, we live in a gendered society and crossing gender lines, even superficially, makes many people very, very uncomfortable. And, of course, it is the reason why I’ve managed to build up a really thriving business as a cross-dressing-positive escort.”

We asked about Veronica’s first cross-dressing date. “Well, I had had the advantage of a long talk with my client – for which he paid me very generously. I think he was relieved just to be able to talk to someone who was open to his needs. He told me he liked the feel of satin and really enjoyed the look of lace. He was not terribly tall and in pretty good shape. I have to admit I could not quite see this successful business guy as a gal but I thought I’d give it a try.”

“We set the date for three days later and I thought it would be best if we met at my apartment. It was a pretty place in an older building in a good neighbourhood which had a rather nice separate entrance. In fact, the rent was one of the reasons I had decided to try escorting.”

“I took an afternoon off classes and hit the thrift stores. I wasn’t sure about sizes but my research told me how you could convert men’s shoe sizes to women’s and I had asked his. I had his waist measurement as well as his chest. I really did not know what I was looking for but he had given me $200 to buy “pretty things” and it is amazing how much lingerie, make-up, false eye lashes, shoes, skirts and blouses and even a really nice, real human hair wig you can buy if you go to a few thrifts. I even found some press on nails and a little bit of inexpensive costume jewelry. I’d cleaned up the apartment and had a little smoked salmon and some cheese ready.”

“The escort date itself was a bit odd for me and, my client assured me, Heaven for him. I made sure I was dressed in a very feminine way. Hose, heels and a floral dress I had worn to a friends wedding. I felt a bit of a gender traitor but, well, it’s business. He arrived right on time with flowers and a very nice bottle of champagne. We had a glass and then I told him he needed to have a bath before he tried on a few outfits. I had some scented bubble bath and a few candles lighted in my not particularly large wash room. I put out one of my nicest fluffy white towels. But the key thing was I had a pretty Turkish cotton robe on a hanger. I told him to enjoy his bath and looking over at the robe said, “And when you’re done there is your robe. And here are your panties.”

“Cross dressers I discovered have a range of desires.” explained Veronica, “Some just like the feel of female clothing, others like the implied humiliation of being “forced” to dress like a woman, still others want to see how close they can come to “passing” as a girl. My first cross dressing escort client confessed that he did feel a bit ashamed at wanting to wear women’s clothes but that he wanted to see what he might look like as a girl.”

“I didn’t have the money to buy proper breast forms.” said Veronica, “But a girl can improvise and two condoms filled with warm water seemed to be just the thing. My client had a forty inch chest and I decided a C cup would be just the thing for a girl starting out. When he came out of the bathroom I told him to take his robe off and I put on his bra and then inserted the condoms. It was a full coverage bra and when he had put his robe back on the illusion of breast was surprisingly realistic. We sipped our champagne and then I took him over to my make-up table.”

“By this point I had pretty much put the fact he was an escort client out of my mind. Now I wanted to see how well I did making him look like a girl. He’d shaved very close and a little foundation and his skin was very smooth. Then I pressed on the long, red, nails. Eye shadow, a bit of mascara, a hint of contouring blush and lipstick and then he was ready for the wig I had bought. It was in a colour very close to his own hair colour and after a few slightly bungled attempts it looked great. I’ve learned that while many cross dressers want long curly hair, a bob or something shoulder length is best for a first cross dresser escort date.”

“Now we were ready to try on some outfits. I had a pair of fairly opaque tights – silly me, an escort should always use stockings – and I had him put those on, then a satin slip and then a fairly short black leather skirt and pretty, sheer blouse. Clip on earings. And then a pair of moderately high heel pumps – I didn’t know it then but learning to walk in heels is one of the most enjoyable activities for a cross dresser on an escort date; but don’t expect it to be fun in six inch platforms.”

“I kept the lights low. When an escort is doing a date with a cross dresser she needs to do whatever she can to give him the best, most realistic, experience of being a girl she can. Keeping the lights low means that the cross dressing escort client doesn’t obsess over the details which are not quite right.”

“When he was dressed we went out to the living room and enjoyed the smoked salmon and cheese and champagne. I taught him how to sip champagne without getting his lipstick on the glass. I had him walk a little on his heels and I corrected his rather immodest sitting posture. But mainly we chatted about what was working and what wasn’t with his outfit and his make up.”

“I think it took me longer to adjust to seeing this quite pretty girl sitting across from me than it took him to adjust to having breasts larger than my own. But when I did it was a lovely escort date. Activities between consenting adults did, in fact, ensue but, of course, in character, so no actual sex was possible. He was, however, a good and happy girl.”

“Plus, he was a girl who left a large tip, money for more clothes and makeup and a different wig and said he wanted to do this escort date weekly.”

We asked Veronica if all of her escorting work was with cross dressers. “Most of it. I’ve branched out into domina work as well as it can be an extension of what some cross dressers want. I put an ad in the “Fetish” section and I’ve been very selective about my clients.”

“The good news about cross dressing clients is that for most of them, a new piece of lingerie, the constriction of a girdle or even a corset, a new wig are all the more reason to come back for more sessions.” Veronica explained, “In the five years I have been doing escort work with cross dressers about ninety percent of my clients have wanted more than one session and many of my clients have been seeing me for years. My first client is still with me.”

“Finding an escort they can trust, an escort who is set up to cater to their particular kink, is something cross dressers can search for all their lives. When they find the right escort they will stay with her.”

We asked Veronica how her business has changed. “Well, as soon as I could I got a much nicer apartment. Basically it is a loft which had been used as a photography studio. It has a full make-up set up and a dressing room. Every girl a star. It’s live/work space and I have my private space up stairs. The dressing room is stacked with pretty clothes, lingerie, shoes, scarves and jewelry.”

“For a lot of my cross dressing escort clients sessions are about perfecting their feminine side: how to walk, sit, use make up, undress, fix their hair. It is very much the ultimate role play. My business has changed because I realize what I am really doing is giving my escort clients permission and direction. Mainly direction.”

“The domina side of the cross dressing client escorting business comes up when I have a client who is reluctant to accept his need to be feminized. A small minority of my clients come to me to be forced into women’s clothes. It is the only way they are really able to accept their secret desires.”

We also asked Veronica what she has learned as an escort specializing in cross dressing clients. “Well, not everyone, and no men are Size 2. I come at this from a very feminist perspective and one of the most significant things I have learned is just how “constructed” gender identity really is. When you are trying to teach a six foot two, two hundred and fifty pound man to walk in heels with a feminine gait, it is pretty apparent how gender norms have evolved and how difficult it is to cross gender barriers.”

“I’ve also learned a lot about how men see women. As an escort I rarely see a cross dresser who wants “A” cup breasts and comfortable underwear. The sort of woman my cross dressing clients want to be is ultra feminine, sort of a caricature of the idea of “female”. I actually make a point of, when I first meet a prospective cross dressing escort client, telling them that if they are looking for a degree of realism, a Jessica Rabbit body is not going to work.”

“At the same time, a lot of my escort clients accept that and are not at all interested in “realism”; they want cross dressing sessions where they luxuriate in curves and ringlets down to their padded butts. They know it isn’t realistic but they are buying my time as an escort to engage in their own fantasies. Which I think is fair enough.”

“But the one thing which I have really learned doing escort work with cross dressers is just how amazingly normal they almost always are. Husbands, fathers, Little League coaches: I can totally see why some rather wise wives treat the cross dressing thing as a harmless kink or even a hobby. By and large my cross dressing escort clients are nice guys and some of them are very pretty women indeed.”

“Plus, as a bonus, I’m the only woman in my year who has a job remotely connected to Women’s Studies.”