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A Crossdresser 's First Time

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I have always liked dressing in woman's clothes since being a child. I often would dress up when my parents would leave the house and I would parade around as a woman would. Now that I am 33 years old and married, I must wait until my wife leaves to dress up as she would not understand.

I often like to dress in the clothing that I like fucking my woman in and just being in those clothes turns me on. I would spend nights fucking myself with large dildos thinking about what it would be like to have the real thing and being able to lie there as a man servicing my body bringing himself to sexual pleasure.

One night I found you can post an ad on craigslist and hook up with other people. I put out an ad and got a few responses, but I did not answer. A few nights later I browsed craigslist and found some photographs of cocks that I would love to have sex with.

My wife was talking about leaving for a couple of days and I started thinking. I decided that I was going to do this but it had to be with the perfect person so my fantasy would be fulfilled. I placed the ad of me being a 6'4 215 lbs. m/w/m that is a C/D and was looking to be turned into and treated like a woman. I wanted a male under forty who is clean-shaven and has little to no body hair. I had to place the ad again days later with a photograph as I got no response.

For the next few days, I frantically checked my email and there it was.

There was an email from a guy along with a photograph of his shaved cock that needed to be fucked. My heart jumped with excitement knowing that I was going to be the one to relieve his sperm pressure!

We emailed back and forth with him sending me a photograph of his face and a handsome guy he certainly was!

It was decided that this could work for us, and he was willing to rent a motel room for our adventure as neither of us were not comfortable at each other's houses. We met for ten minutes at a bar where he gave me his room key and told me to get comfortable and ready.

I arrived at the motel, and I put my wig on with the hair up in pigtails as I bathed. I finished my bath making sure to shave nice and close. I wrapped the towel around me and walked out into my room to where my clothing and makeup were set up like any other woman would do.

I felt so different, almost feeling like a woman even though I have never been fucked by a man yet. I put my white satin panties on enjoying how they glided over my freshly shaved body. I put my bra and pulled it up onto my chest. I then put on my black and white plaid skirt feeling on it slid so smoothly over my soft legs. I followed that by putting on my shirt and then I went and sat on the floor. I pulled on my anklet socks that have the lace around the edge making me feel like a little slutty babysitter.

Standing back up I took care in putting my makeup on right. I must look perfect for tonight. I stopped and gazed at myself in the mirror. I then looked down at my skirt and socks realizing that he will be between these legs making me into a woman tonight. My heart was racing so wildly it made me very horny. I then noticed that I began to look very much like a woman as I was putting on the makeup. Once I was done with that, I put on my bracelets like I see so many girls wearing. I also put on my leather choker that has "Slut" on it. That is what I will be when tonight is over, a slut.

I put on my black patent leather Mary Janes placing the strap over the top of my foot and putting it through to the clasp. It made me think about how I am now tied into what I am about to do. I looked down admiring how soft my legs were and how I love seeing the white sock showing through the accessible area of the Mary Janes. I slid myself up on the bed before lying down. This is where it will all really happen as I pictured him on top of me getting ready to fuck me for the first time.

I sat up as the phone rang indicating that he is walking into the building. I begin to shake as I head for the door. I look at myself in the mirror looking at a girl getting ready to become a woman. I hear the knock on the door, and I slowly move toward it. Looking at myself in the mirror one last time as I walk by realizing I do not have to answer, but my desire for the experience overtakes me as I take a deep breath and open the door.

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