Yay for Cross-dressers!

This week, I got paid to fuck a beautiful boy. A very beautiful boy. A boy who likes to wear lacy lingerie and who likes to be called by a girl’s name while my cock is deeply buried in his tight, delectable ass.

This beautiful boy pre-booked his appointment, which is always appreciated. I originally thought he was a different client, a regular, who likes to be dressed as a girl and fucked. The driver dropped me off at the motel in Burnaby. I went up to the room and knocked. I was dressed in a skin-tight black dress, thigh-high stockings, sexy boots, over a gorgeous black lace strappy teddy. I love my job. Honestly, sex workers get to wear the best clothes to work.

I was pleasantly surprised when a gorgeous, twentysomething boy answered the door. He looked Italian, with beautiful olive skin, dark brown eyes you could lose yourself in, a nice body and a cute smile. His reaction to me was even better. “Wow, you look beautiful! Come in! I LOVE what you’re wearing!”

I smiled and thanked him, and we chatted a bit. I like to make a few minutes of small talk to put a client at ease. Soon, we were discussing what he had in mind for our session.

He told me that he likes to be dressed as a girl, and referred to as a girl. He told me that his name was Mark, but for our purposes, he would like to be called Marsha. He wasn’t into pain, just being fucked and treated like a girl. He wanted to start by trading lap dances. The lack of musical options on the TV was a small impediment, but I did my best to lap dance for him. I have learned a long time ago that men are truly not that hard to please. You don’t have to have acrobatic dance moves when you’re dressed the way I was dressed that day. When I had stripped out of my dress and gyrated in his lap, rubbing his cock through his jeans, he told me he would like to give me a lap dance.

I pulled out the lacy lingerie I had packed for him. He put the black lace teddy on and layered the purple slip over top. He danced for me, and I very vocally appreciated his efforts. Soon, we were in bed. I was on top of him, kissing him and rubbing him through his lingerie.

He liked dirty talk whispered in his ear. He had a fantasy of being gang banged by a bunch of guys, and for me to be there controlling him, telling him what to do. “I take huge cocks in my ass,” he said.

“I bet you do,” I said. “You’re a dirty little cumslut, aren’t you?”

I lubed his ass slowly, pushing the lube in before inserting a finger. He loved it. Soon, I was opening his hole with two, then three fingers. When he was begging to be fucked, I excused myself for a moment to wash the lube off my hands and rig myself up with the strap-on. I picked the big, pink dildo and walked back to the bed. “This big enough for you?” I asked, raising an eyebrow.

He looked excited and nervous. “Um, it’s big,” he said.

“I’ll go easy,” I said, thinking that perhaps he had only taken big cocks in his fantasy life. “Suck it,” I said, putting it in his face. He took in only the first quarter, but I was still careful to praise his cock-pleasing skills. I of all people know that gag reflexes happen, although they can be largely unlearned with time.

I started out on top, fucking him slowly, following his lead. Soon, he was wrapping his legs around me and pulling me in deeper. I whispered in his ear how I was going to fuck him and I was going to let a bunch of my friends fuck him, pass him around and use him like a sex toy. We fucked doggy style for a while, and I trailed kisses down his back, whispering in his ear how good it felt to fuck him, how great he was at pleasing cock.

He enjoyed getting on top and bouncing on my cock. My pubic bone is still a little sore from the rubbing of the strap-on, but I don’t mind.

The session ended with him jerking off and me feeding him his cum and describing ten guys ejaculating in his mouth.

After the session, he told me that he had never done anything like that before, and that being with me had been a great experience. He was looking forward to exploring his kink further. I told him that I actually do have a fetish for male cross-dressers and that having him as a client was a treat for me too. He asked me if I could organize a gang-bang for him. I told him about my friends who are male escorts (and a married couple) and he found that idea incredibly sexy. I don’t know how much money this boy has, but somehow, I don’t think he’ll be able to afford the three of us. Still, I am really happy that I had the chance to help him explore his kink, and to teach him that there are women out there who are into what he’s into.

I hope this boy calls again. He said that he would. So here’s hoping.

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