A Crossdresser's First Time
"Are you glad that you will become the woman you've always dreamed of tonight?" Mistress asked me as she examined my makeup.
"I'm so excited!" I replied.
"Good. Don't worry about a thing, just close your eyes as you suck him and pretend that it's my dildo in your mouth. I'll hold your head, direct you, and push you so that his cock tickles your tonsils." She said with a smile as she added a bit more color to my lips.
"Do you think I'll be able to make him cum?" I asked.
"Of course dear, all that time with my strap-on in your mouth has turned you into a top notch cock-sucker. When he does cum, swallow what you can, but don't worry if you miss some, you can lick it all up afterwards." She answered.
"Thank you for doing this for me Mistress, I love being your sissy!" I said.
"You're welcome, and I have a little surprise for you. If you are a very good sissy tonight, if you make him explode in your mouth, if he and I are both perfectly pleased with your performance, well, then I just might take that hard old cage off your little sissy clit and let you cum while he drives his hard cock into your tight little hole." She replied.