I have always like 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 like a woman would. Now that I'm 33 years old and married, I have to wait until my wife leaves to dress up as she wouldn't understand.
I often like to dress with 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 dildo's thinking what it would be like to have the real thing and being able to lie there as a man service 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 several responses but I didn't answer. Several 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 got to 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 40 who is clean shaven and little to no body hair. I had to place the ad again a few days later with a photograph as I got no responses.
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 comfortable at each other's houses. We met for a few 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 make up was 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 make up on just right. I have to 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 though the open 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 don't have to answer, but my desire for the experience over takes me as I take a deep breath and open the door.
He walks in and stops just inside the door as I close it and lock it. I turn and say "hi" with everything that I got. As I walk toward the bed he grabs me around the waist pulling me tight against him as his hand slides up my smooth outer thigh and right under my skirt. I feel his fingers trying to slide under my underwear as he seeks my pussy to stick his fingers inside of me.
He whispers in my ear, "are you ready Andrea?"
I replied, "I think so." As I reach back sliding my hand down his cock which is pressing to be let out of his pants and into mine.
He lets me go and he sits down on the bed. "Walk around for me so I can get a look at you Andrea."
I do my best and turn around in front of him walking to the other end of the room and back. He tells me I look beautiful as he lies back on the bed. "Straddle me and act like your fucking me so I can see if you are ready to become a woman."
I slowly go over and straddle his obviously hard cock. My skirt is just above my knees and I pretend to fuck him slowly by rubbing my white panties across his thick dick.
He smiles at me and says "not bad, for a girl, but get on your feet and pretend to pump it in and out of your pussy baby."
He then tells me to stand up and he tells me to move over to the wall. I do as I am told and he moves closer into my personal space. I feel his deep heavy breath against the side of my face as he whispers into my ear "What is your purpose Andrea?"
I tell him as I look down, "to satisfy you sexually with my body."
He smiles and says "how would you do that Andrea?"
"By letting you fuck my face and pussy until I make you cum."
He then lightly pushes down on the top of my shoulders until I end up on my knees. I unbutton and unzip his pants. I then pull them down to see his swollen cock ready to get serviced. I put the condom on his cock which is now sticking in my face. My heart is pounding so hard and I'm shaking so badly I was surprised that I could put the condom on.
"Get off your knees, and squat. Put your hands above your head." I do as I am told and he grabs both my wrists with one hand as he takes a hold of his cock and slides it up and down each cheek. I'm beginning to get nervous as he traces my lips with his cock as I realize that I am obligated and I am not sure I want to continue. He then pushes his dick slightly against my lips trying to part my lips as I refuse to open my mouth.
"Andrea, slide your heels back to the wall like a good girl. Now, we will begin the process of making you into a woman, first I have to fuck your face so open your mouth nice and wide."
I open my mouth as he moans as his dick begins to slowly slide in and out of my mouth. I am off balance as he now has a wrist in each hand; the wall keeps me from backing my head away as he keeps sliding his cock in and out of my mouth with smooth, even strokes.
"Andrea, you're doing a nice job, a little faster now." He begins to pick up the pace with his cock sliding between my lips. I sucked him for about five minutes when he told me to get on my knees and grab my heels.
He then slides his cock back into my mouth as he places his hand on the back of my head. He works my mouth for a few more minutes while moving it in and out of my mouth very slowly before pulling his cock out. He then grabs my wrist and pulls me over to the bed. He then tells me to lie down onto the bed.
