Made to be a Transvestite Pt. 01

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He wants me to be his replacement girlfriend for the weekend.
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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.

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AnonymousAnonymousabout 6 years ago
good story

the first time I went in to a bar was a few years ago when I walk in I saw men kiss men so I just walk up and older a pop the bar man said just pop I said yes sir then he hand me the drink when he did my hand touch his he said nice soft hands I thank him we got talking I keep looking at the others he told me you know your in a gay bar I told him no sir I ask him you want me to leave he said it up to you I told him I will stray he ask what I do for work I told just about anything how would you like to help me for the rest of to night I said yes I will pay you some money it be about five hours work I what do he want done there dishes to be wash for now and later help clean up when I close I said fine show me were the dishes are I walk back with him to the room I start to wash he came back and wrap a apron on me as he did he slap my ass I did not move he tie it up and said you have a nice ass then he padded it some more yes very nice I said I glad you like it sir here come the other boss he look at us and said why this man not in unfrom he told him he just started no well go put one on him the man told me to come with him we went to a room were there were outfits I remove my clothes I was now down to my underwear I ask him if he want me out of them he said yes I remove them as I bend to pick up my clothes he came behind me he put his hand my ass I did not move I told you want me to get dress now then I felt his finger go in my ass hole it hurt a bit soon he work it in and out he keep it up for awhile I just said yes then he pull out and shove his big hard cock in I cry out yes he told me I had that man come in there to yell at me to take you back here for this I told I was hoping you would I always want to be some one bitch he keep on banging me and after that he told me you are mine bitch now and I will dress you as one well I was dress in sissy girly clothes once I was dress a man came in he look at me and said what a lovey girly bitch boy you have boss the told him come in and see her she love to suck cock I knew what to do I just pull out his hard cock and suck that my girl you make a good bitch

justagirlatheartjustagirlatheartalmost 7 years ago
I liked it

It's a good start for part 1

DeborahAnneDeborahAnneabout 7 years ago
I think this is a good start

But I want more of this, so please continue on and let us know how it is going. I for one would love to be in that position, but I am a bit old to be a girl friend to a young man, lol more like his mother. But I love to suck cock, and to offer my cute little butt for use would be heaven for sure. da.cd@frontier.com

ChatNoir36ChatNoir36about 7 years ago
Anonymity affords such cowardice.

MECHMAN17, your tale rocks. What the three anonymous critics & Jimmcdonald609 (who thankfully seems to be possession of a healthy set of cojones) appear to have missed is that Literotica caters to those seeking FANTASY. MECHMAN17 you clearly have talent; with time & practice you will develop the finesse required to quieten the cowardly & impatient. Don't lose heart! I wanna hear the next part to your story so get to it!

AnonymousAnonymousabout 7 years ago
Yeah, No!

This story was so unbelievable (not counting the typos) as to be almost laughable. They should put the comments before the story so as to save people wasting their time reading it.

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