Cross dressing is an activity that has been going on for thousands of years. From the ancient Greeks to modern-day fetishists, cross dressing has a variety of purposes and a history of it can be found in folklore, literature, theater and music.

Cross dressing for disguise purposes has been extremely prolific in history, in addition to wearing the other sex's clothing for comfort (such as Calamity Jane donning men's pants in the Wild West). It doesn't matter which reasons compel your clients to desire a cross dressing experience. What matters most is your willingness to provide a shame-free zone and the opportunity for him to fulfill his fantasy.

However, many escorts with no experience in the cross-dressing world don't really know what to expect when they offer such services. Here are the 13 things you should know:

1. Cross dressers are often heterosexual. Even though the media stereotypes cross dressing males as gay drag queens, that depiction is not always an accurate one. Of course, some cross dressing men are homosexual and prefer the company of other males, sexually. However, just like the media paints an untrue picture of escorts, cross dressers get bad press, too. Cross dressing clients simply want to experience what it is like to wear softer, silkier fabrics that cling to their bodies in ways that differ from their traditional clothing. Their desire to dress in pretty colors or frilly designs does not automatically make them gay, just as a man's preferences for rugged attire doesn't mean that he's straight.
2. Cross-dressing clients like sex, too. When a client contacts you and inquires about cross-dressing services, he also expects an intimate component to accompany other aspects of the encounter. An appointment where you offer a client the opportunity to wear female clothing will eventually evolve into an encounter much like any other you experience with clients. After his initial seduction is coordinated through the use of women's garments, your client will likely be aroused and hoping for some sexual contact. Most escorts who offer such services to clients indicate that the encounters are nearly identical to non-cross-dressing ones, except that the clients wear women's attire or undergarments during the experience. Do not anticipate that the entire encounter will be a dress-up party; it will not be limited to wearing women's clothing.
3. It's a good idea to provide lingerie and clothing as part of your cross-dressing services. While some clients may come prepared with a whole collection of goodies they've collected over the years, others won't have a single item available to them for the experience. Most men don't have places to hide their sexy, frilly items, so they don't have any. Others have been caught by loved ones and purged their collections, along with making promises to never indulge in the activity, again. So, for these clients to experience the thrill, they need for an escort to provide them with proper attire. Pick up garage sale or thrift items in extra-large or plus sizes. Look for soft, silky fabrics and draping fits. The more feminine the style, the better. Select lingerie with quite a bit of stretch to it. You may be able to incorporate some of your cast-off pieces, too.
4. Comfort your clients through acceptance. Many clients have faced ridicule from family members or loved ones who have discovered their secret passions. They've been given ultimatums to abandon their fantasies or lose their partners. And some clients will have great shame over their desires. They, personally, feel that their need to dress up in women's clothing is not masculine, which strongly affects their self esteem and body image. As an escort who offers these kinds of services, it's your job to reassure your client that he is sexy. And don't tell him he's hot, in spite of his desire to dress up in women's clothing. Tell him he looks good in the red bra and thong set he's put on for you. Reassure him that his fantasy makes him even sexier, because he is so comfortable with all sides of his personality and desires. Even though it may be difficult to be turned on by a man wearing silkier undies than you, it's important for you to make him feel like he's really attractive.
5. Consider encouraging your client to book enough time to fully accommodate his desires. If a client expects to take some time to properly prepare by dressing, fixing a wig and putting on makeup, the usual hour encounter may not be long enough to get it all done, in addition to enjoying some "together time". Without sounding like you're simply trying to get more money from him, describe to him how he may end up short on time to do everything he wants. After you've explained how you expect the encounter to go, allow him to comment and ask questions. After your discussion, he may be completely on board to increase the encounter by 30 minutes to an hour. Additionally, not only will the encounter take longer to complete, but booking it may be a lengthier process, too. Especially if he's a new client or new to cross dressing services, he may ask lots of questions over the course of several threads of communication. Although it's easy to become impatient with an overly chatty client, keep in mind that he may be very nervous and excited (both!) about the experience and wants to make sure he fully understands how it will go.
6. Your client may take on another persona during the encounter. Your clients may demonstrate different personalities, but not like Sybil, the multi-personalitied young woman featured in both film and literature. Much like how you alternate between your escort personality and your "real" persona, your clients may blossom into someone entirely different when they are dressed in women's attire and other accouterments. They may even take on another name (just like you do). John might become "Joan", Joe would identify with "Jo". Their voices, gestures, methods of walking and movement and attitudes may adjust when they are dressed in items other than their traditional manly duds. Don't be intimidated or assume that your client has an identity disorder. He is just acting out his fantasy of being someone different, much like you put on a different character when you step out as an escort.
7. Focus on touch when you're with a client who enjoys cross dressing. Many men are interested in cross-dressing experiences, because they enjoy the sensations they experience from the softer fabrics on their skin or genitals. Silk panties against their testicles or penises create erotic feelings for them. Some clients love to wear silk stockings and feel their legs stroked through them. A client may enjoy how it feels to kiss you when he wears lipstick or lip gloss, which is usually a taboo for men. The entire cross dressing experience can be even more enhanced by focusing on providing light touches, soft massages and caresses that slowly and slightly move the fabric against your client's skin. Think of how nice some of your favorite garments feel against your skin; use these thoughts to inspire you in ways to help your client find even more pleasure from the experience.
8. Discretion is key. Your client faces extreme risks if his colleagues, family members or loved ones discover his love for cross-dressing activities. Not only will he face the stigma of seeing an escort, but he will also suffer the harsh judgment and assumptions about his character and sexuality from being found out as a cross dresser or drag queen. And while you encourage him to act out his fantasies with you, you must also persuade him that his activities are not advised for his mainstream life. Unfortunately, his life could be irreversibly affected if others found out he liked to wear women's panties. So, while you reassure him that he's "normal", you must also find a way to discourage him from wearing his soft and silkies out in public. And be sure to help him wipe off all make-up and remove all jewelry before returning to the "real world" after an encounter with you. Helping him learn to separate his two worlds will make him successful and happier.
9. Don't laugh when your client comes out in full garb. While the sight of a man strutting around in a bikini (complete with body hair and visible penis hump) may be enough to make you giggle, stifle it for the good of your client. Escorts see a little bit of everything through their time with clients. It's certain you've observed it all. However, instead of injecting humor into the situation this time, attempt some flattery. Your client has opened himself up to you, showing his vulnerability. You must not knock him down with your laughter. However, do keep in mind that as you and he begin to fool around, it's perfectly acceptable to giggle and laugh. (Just not at him.) He may even giggle as he finds pleasure in the experience. And your client may even find it exciting to giggle like a couple of girls together, once he gets comfortable with the experience.
10. Make-up can help your client complete his look. However, most clients don't have a clue about how to put it on or what to do with it. It's a good idea to provide some cheap options for him. Collect some samples or buy a cheap collection that has a variety of colors and types of makeup included in it. Do not consider allowing your clients to use the makeup that you normally use. (It's too expensive for him to waste, and he may mess it up by mixing colors, ruining brushes, etc.) You may have to act as teacher to guide your client how to properly apply the makeup, too. He may understand how to apply foundation, but eye liner, shadow or mascara are a bit trickier. Some clients just want their escorts to apply the makeup so they can look their very bests. You've got to be willing to help out, when asked. However, while some clients are all about the makeup, others won't care a bit about it. Always ask ahead of time before you assume that your client will want to include this in his encounter.
11. Having a collection of wigs can help enhance the experience. Many of your clients will be interested in wearing a wig, at least for a short time. It's not important to have lots of wigs, just a few. Make sure they are somewhat combed out and prepared for use. Halloween season is a great time to stock up on wigs; most clients don't need expensive ones for their efforts. However, you may be able to pick up nicer wigs at garage sales from time to time. Be prepared to help your client style the wig, by brushing the hair or inserting a barrette, which gives him a stronger sense of being a woman through the cross-dressing experience.
12. Be a willing teacher about all things womanly. Think of your client as a tomboy younger sister who doesn't know how to be a lady. Because your client may want to appear more feminine than he knows how to be, he may ask for your input. You can casually coach him about how to walk in high heels, ways to sweeten his voice and ways of speaking that make him sound more ladylike. Provide excellent examples and demonstrate what you mean as you give him tips.
13. Have fun during the encounter. It's important to follow your client's lead to ensure that he gets what he wants out of the experience. But as you're doing that, don't forget to enjoy yourself. All encounters should be fun and entertaining. Don't get so uptight about providing unique services that you forget about having fun and enjoying yourself, too. Laugh, joke around and incorporate some silliness into the experience. Providing a light-hearted atmosphere for your client will help him more easily open up about his fantasies and fully enjoy his time with you.

Vintage cross-dressing image credit: http://www.flickr.com/photos/foxtongue/1374767/