One of the most fun, popular yet secretive fancies that I've encountered in my time as an escort has been playing with crossdressing men. Names have been altered to protect anonymity of clients.
Let’s take the example of Michael who first came to meet with me about six years ago. He told me that he’d tried to suppress his urges to wear women’s lingerie for most of his adult life. His wife of 20 years had grown increasingly distant and eventually they had separated. Free from needing to be secretive he was hoping to express his desires to an understanding an open minded woman.
Previously when he was married, he had limited opportunities to explore his cross-dressing fetish. If his wife was away for a day he would plan and look forward to dressing in her clothes. Now that he had the freedom to explore without worrying about hiding it from his now ex-wife, he felt an emptiness, as though the secrecy was necessary to enjoying the dressing up sessions.
He felt that part of his excitement came from the adrenaline from thinking about what if his wife would have walked in on him dressed in women’s clothes and wearing makeup. It turns out that when he was an adolescent, his mother had uncovered his secret and would shame him at family gatherings, laughing and saying, “You love wearing silky stockings don’t you?” and “Mummy’s little sissy boy”. Now the thought of humiliation and sissification were two things that drove Michael’s erotic urges. Without fearing his wife’s shaming, he didn’t get turned on.
So this is where I am able to provide a service and he now gets more turned on than ever. First he comes to visit with a nice big bag of clothes and high heels he’d like to wear. We both play fun dress ups in lingerie and dresses. I do his make-up and he looks stunning in his long blond wig. He gets a thrill out of transforming into the radiant, confident and sexy “Misha” and to make it even more enjoyable and memorable I take photos of him all dressed pretty which then he can admire and share.
The part I like is when he’s reviewing the pics and he truly looks like a slutty girl. I say things in his ear such as, “Look at that pervert, dressed like a slut trying to get some attention from the tradies down the road.” He squirms and tells me he feels deliciously naughty. I love teasing him as I get off on the perversity of it all.
I also love to threaten that when he’s a really good sissy I’ll take him out shopping to
Victoria's Secrets in person. He blushes and gets hard when i do this.
The thing about seeing a professional escort is that there is not much we haven’t heard or seen and we never judge, our bank balance depends on it!