How did I never write about this?
The request was simple: A woman wanted me to wear her panties. Why? Because her ex-boyfriend used to, silly! Be aware that the word "silly" was what she actually said to me -- as if I was a six-year-old asking a foolish question in kindergarten class.
I didn't oblige her request. It's not that I have anything against cross-dressing, or those who engage in it. I just didn't feel comfortable. Had the panties been washed? Had anyone else other than her worn them in the past? Was a pink g-string really necessary?
"Plenty of guys do it," she said. "Why not give it a try?"
I smiled politely. "Listen, I'm the last person to judge anyone's sexual activity, but this just isn't my deal."
"Really? Why is that?"
"Well, to tell you the truth..." I trailed off and thought of a viable excuse. "Because I only do this with my girlfriend."
That struck the client by surprise. She opened her mouth, then closed it, whatever words she planned on saying having obviously escaped her. She sat up in bed, adjusted the straps of her negligee. I could tell she was irritated, but I also knew I wasn't wearing her underwear.
"I'm sorry if that ruins the fantasy," I said. "My having a girlfriend and all that."
"No, it's fine. I always wondered about that -- whether escorts have relationships outside of work."
"I try. So, we can have sex any way you like it -- just no cross-dressing, I'm afraid."
What happened next wasn't completely out of left field, but slightly unexpected. Turns out the whole time her boyfriend had been wearing her panties, she'd wanted to try on some of his clothes: dress shirt, trousers, that kind of thing. After stripping nude, I handed her my clothes, then let her go to the bathroom and try everything on.
She returned wearing my dress shirt and no bra, along with my tie. That's it. The shirt opened to reveal her nude body, the tie swaying between her breasts. Is it wrong that I actually got off on this? I'm not quite sure. All I know is I talked myself out of having to wear a g-string, and still left the client happy.
If that isn't a valuable skill, I don't know what is.