I decided to call in sick the next day. I was exhausted from a night of love making with Sandy. My ass was also a little sore, so I did not fancy sitting down in an office all day. We had also talked for hours. We knew each others every intimate secret before long. Sandy had not had many lovers, and I was her first since she had a couple of operations to become more feminine. She did not want to get rid of her cock though. How she was now was she wanted to be.
After a short sleep we slipped into her bath together, fondling each other all over. Then Sandy came to the conclusion that I needed to free myself of all my body hair. She set about shaving me from my chest down. I had never felt like this before – so smooth and fresh. It was sexy. I could not believe the way my cock looked with all the hair from balls gone. When Sandy sucked on my balls I nearly came right away. But she told me to save it for tonight.
We stayed in most of the day, but as the evening approached and we had finished a bottle of wine, Sandy said it was time to get ready to go out. “But I don’t have anything to wear, I’ll have to go home for a while.” I said.
“Don’t worry, you are going to wear something out of my closet tonight.” Replied Sandy.
I thought she was kidding when she presented me with a shiny blue dress. She had me dressed in sexy underwear and wearing a blonde a wig. I was starting to look like a woman and not a bad looking one at that. What was I doing. It must have been all the alcohol, because I did not put up much of a fight. We headed out, dressed as two women.
Sandy led me into a bar she said she frequented from time to time. She told me it was a place for guys to dress as women and be themselves. But then she gave me a challenge. “You know what would be really sexy, is to watch you go up to a guy who comes in here looking for someone just like us, and to suck his cock right here.”
I looked at Sandy thinking she was joking. “No way and certainly not here in front of everyone.” Sandy’s reply was “why not” and she pointed to 3 other couples clearly sucking each other off in various parts of the bar. “wow” is all I could say. Sandy then pointed to a guy standing at the bar who was clearly looking our way. “Go, and make sure you use a feminine voice – remember your name is Kylie.”
“Hi, I’m Kylie.” I said
“The name is Bruce. So pretty thing, you look beautiful and innocent tonight.”
I blushed as he guided my hands to the outline of his cock. If I thought about what I was doing I would have run. I should have run to be honest. But I wanted to please Sandy. I could see her watching closely as I undid Bruce’s fly and pulled his cock out. It was at least 8 inches long and quite thick and uncut. I knelt down and took him in deep. He held my head down and forced me to engulf it all. I was sucking hard as he thrust into my mouth. A crowd had gathered around to watch as Bruce fucked my face. In no time his cock was pulsing and cum was shooting out down my throat. He held me there making sure I took every last drop.