Made to Be a Transvestite

The names in this true story have been changed.

*****

Steve and I have been friends since our freshman year of high school. We played basketball and tennis together, were part of the same social circle, and after high school became best friends. He was part of my first (failed) wedding and I was for him. Life changed in many ways but through my 28th birthday, but not Steve.

Steve and started playing in weekend golf tournaments throughout the state during the spring and summer. They would be held all over, from the mountains to the beach, and it was nice to get away from Friday to Sunday and have a relaxing time twice a month. Neither Steve or are married or have kids, and the benefits of being young executive types means we can take off for and early weekend pretty much whenever.

The only real problem about these trips was Steve's obnoxious on again off again girlfriend Melissa. She was an amazon of a woman, about my size and about as fit and built. She would be with him one week, gone the next. The worst thing is that being with her amped up his alpha male attitude, and since I've always been a little more quiet and reserved he started to pick at and tease what he called my soft nature.

So the weekend of the next tournament arrived, and since Melissa was supposed to go I planned to meet them at the beach motel around four o'clock for check in. I was packing up to leave when Steve called. He told me he was on the way down. He also mentioned that Melissa wasn't coming (yes!) and for me to pack light as he had some clothes packed up that I could wear. I was happy to not have to deal with that obnoxious woman and headed on my way.

Steve texted me while I was on the way there and told me he got us a deluxe room instead of us each getting a small one. I figured it's fine and I picked up a key when I arrived. I did think anything of it until I got to the room. Once I opened the door I knew something was up.

There was a desk, a TV stand, microwave and one king size bed in the room. Steve came to greet me at the door and told me to have a seat on the bed. For some reason I quietly did just that. He took the small bag I had and told me he would be right back as he went into the hanging closet area, pulling out two dresses.

I was very confused at this point, but Steve wasted no time in explaining. He told me over the past few months with Melissa he was missing something. She didn't have the shared interests that we both had, and she was too butch for him. She also did not enjoy anal sex, which Steve always bragged was a big thing for him. He told me that he had been thinking about how to come up with a way to get the best of both worlds, a girlfriend and a friend, common interests and some feminine behavior, and he decided on me.

I was confused (and a little excited/flattered) by this. Steve is a masculine, attractive, and very successful man who could pick up any woman he wants. He had never mentioned a gay thought in his life but without another word he took me by the hand and undressed me fully. He told me to go use what was on the bathroom sink and then shower. My head now swimming I went in and without though gave myself an enema and then took a shower, using the fragrant body wash he set out. I came out after drying off and there were red lace things on the bed while Steve sat naked in the room's desk chair drinking a beer with a small black bag on the desk. He said that things could move to the next level if I knew what to do.

I put on the thong and made my way over to him, quietly kneeling before his large package. He pulled my head up by my chin and told me if I continued he would be in complete control of me, and what he wanted would go. I didn't hesitate for a moment to take his manhood into my mouth. I had never been with a man but I put everything into pleasing Steve. For his part he removed several small to medium dildos from his bag along with lube and started to stretch my ass out.

As I tried to deepthroat Steve's large dick he began to clench up. He seemed to smile at my efforts. He looked at me and said don't worry about swallowing, I always cum twice. I was wondering if I could handle taking his load. I didn't have to wonder long as a moment later he pumped what seemed like a cup full of his cum into my mouth and down my throat. It was hot and surprisingly satisfying. He smiled down and said onto the main event as he lead me to the bed.