Transsexual secretary
By
Heidi
I worked at a big advertising company in New York City. I was not married do to my crossdressing. My crossdressing was one of the most important things in my life. I would come home from work and get dresses in my skirts or dresses. I would cook, clean, have sex with guy and go out and have fun.
I stared to dress when I was an early teen. I would go into my mom’s or sister’s room and steal there clothes and put them on when they were gone. Started out wearing panties and bras, then after some time moved to wearing skirts and dresses. After some time at wearing there clothes I was hooked on crossdressing. At times I would even go to school wearing my sister’s panties. One time I even went to my Halloween dace with a girl I know. What a great night. I had on a short skirt, low cut top and a lot of make up to make me look like a hooker.
I was one of the big wigs in the company. I would have to go to the customer to sell them your advertising plans for there company. I would have to go all over the world. That would give me lots of time to dress when I was on the road. I would bring my clothes with me and dress in my room. If I went to a city I have been to before I would go out. I would find out were to go on the internet. I would to gay bars for a few drink and look around for nice gays to have fun with.
The first time having sex with a guy dressed was on a trip. This guy came to me at a bar and told me how good I looked and he wanted to take me home and have fun with me. I know I wanted to have sex as Heidi that night, so I went home with him. When I stepped though the door I turned around and wasted no time and quickly knelt in front of him and started unbuckling his belt and unbuttoning his jeans. I finally pulled his cock out and it was the first time I had a close and personal look at someone else’s cock. It was long, smooth, and not too thick. As if by instinct I opened my mouth, stuck my tongue out and started licking his cock like a lollipop. It was such a weird sensation and feel in my mouth.
I was so turned on knowing that I was finally doing what a girl does. I started really getting into it and started bobbing my head up and down his cock and slurping at it as if I was starving. I licked and sucked and jerked him and eventually I started to taste a familiar taste, it was his precum. I had tasted my own precum before and knew what it tasted like. Being so turned on and this guy being so cute and nice I was determined to have him be my first fuck.
In between mouthfuls I asked him if he wanted to fuck me. And he nodded yes with eagerness. I got up, danced over to my purse and grabbed a condom. I went back on my knees and rolled the condom on his cock.
After making sure the condom was on he lubed his cock with my mouth. He turned me around to put some lube around and inside of my virgin asshole with his fingers sliding in and out.