Connie was finally ready to go out and meet the boys. My Sissyboy looked like the dirty whore she has always dreamed she could be. We have spent weeks getting her look together. We found some sexy panties that she can tuck her little surprise into. I wanted us to look hot together so we found matching little black cocktail dresses. I wore some hot black strappy heels. Connie went with a sexy red pair. We wore our push-up bras and wore deep red lipstick. I had taught Connie how to suck a cock with cucumbers. I taught her how to put it deep into her throat, and how to swallow a load.

When I first met my favorite Sissyboy, he was still Conrad. He secretly told me how he was attracted to men, as well as women. One drunk night, he confessed to everything he fantasized about. He sometimes wanted to be a girl. That night we spent hours going through my closet, trying on my sexy clothes. He was already wearing some sexy red lacey panties. He was on his way.

His transformation was fun and amazing to me. “Sam- make me a dirty whore!” he begged me. We laughed and put on slutty makeup together.

Finally, the day had come when Connie was ready to suck her first cock. We caught a cab and headed for a dive bar in the village. A big black dude was the first to approach us. We had settled at the bar drinking Cosmos when he walked over to us. The dude bought us another round. Connie looked nervous. I figured I would break the ice. “Connie here is so eager to suck her first cock. Can she suck yours, baby?” I asked. Connie looked shocked and a little nervous. This guy was big and almost definitely straight.  He looked her over and said, “Yeah let’s go into the alley”

I smiled as he took Connie by the hand and took her to the alley. Connie came back about 20 minutes later. her blond wig was messed up and her lipstick was smeared. She was smiling. Her first Cock Sucking experience was a good one! Connie is now a professional cocksucking slutty sissyboy and I love her!

 

 Phone Sex Kingdom Nicole Burke