CROSSDRESSER FIRST TIME

CROSSDRESSER FIRST TIME

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.

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 you’re 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 unbuttoned 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 am 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 am 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 wonderful 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 on the bed.

"Andrea, what are you good for?"

I replied, "to be your little slut."

"By doing what?"

"Letting you fuck me."

He tells me to spread my legs as he sat back telling me to finger my pussy. I lubricate my fingers and I slide my panties aside. I begin to stick my finger inside of me and begin pumping my finger in and out of me. He kept telling me to add fingers until I had four inside of me.

He reaches up and pushes two of his fingers inside of me with mine. I arch my back so I can manage all six fingers and deal with the discomfort I feel at first.

He then tells me to lube his dick, so I put lots of lube on his thick hard shaft. I then bring my legs together as he tries to get in between them as I am nervous looking at his cock bouncing in front of him realizing he wants to put it inside of my pussy. He begins to stroke my shaved legs and runs his hands over my panties as he pushes his hands between my thighs.

"It's time Andrea for you to become a woman. I am going to fuck your little pussy. Spread your legs for me."

I slide my legs apart as he moves his cock closer to my pussy. I think to myself, I cannot believe this is it. He is going to fuck me with his cock like I have done to my wife so many times. He had the same look that he was going to abuse my pussy like I also have done to girls I have fucked in the past.

"Andrea, tell me that you want me to fuck you" as he slides my panties over and sticks his fingers inside of me.

"I want you inside of me."

He pulls his fingers out and he now has his cock slightly pressed against my opening.

"Here's what you wanted Andrea, my fucking dick inside of you."

He begins to push his dick inside of me as I let out a groan as my pussy resists him forcing himself into my ass. I begin to sweat as my body was trying to deal with him trying to get it inside of me.

He only gets it in about halfway, so he pulls out and pushes back several more times. I cannot believe how warm his member is an oddly soft despite how hard it is. I now realize that his balls are against my ass cheeks. He moans keeping it buried deep in my pussy.

He then says, "all you have to do is make me cum now Andrea."

I put my leg up on his shoulder as he begins to fuck me slowly but with solid thrusts. I whimper as I feel every vein and muscle in his fat cock as it pushes against my pussy walls. I grunt a little as my back arches to manage his full length.

"Come on Andrea, you have to moan like a woman to be a woman."

All I could do was grunt and nod doing my best to be a little louder. I wanted him to hurry and finish as I had only fuck myself with a dildo for five minutes which was enough. He did not pick up his pace but kept slowly fucking my body moaning with each solid push into me.

After a few minutes I tell him I need more lube. I fill my hand with lubricant and rub it on his cock as he kept fucking me. I could feel my little pussy stretching with each thrust as he fucked me from every angle.

I began to really enjoy feeling his sweaty body against mine as he continued to have sex with my body. I laid there enjoying just being there as he got to use my body like I have done to my wife.

I tell him I need more lube again so he pulls out so I can lube his cock by sliding my hands up and down the length of his cock. He tells me to walk over and put my hands on the wall. My pussy is dripping from the lube, and it is running down my thighs.

"Fuck me, Mister."

He says, "Oh, I will."

He walks up behind me pulling my hips backward and right onto his now even larger cock now swelling with his sperm. He begins to fuck me and pushing hard enough at times to make me go up on my toes.

The feeling of that dick deep inside me was making me feel like I was going to cum. I cannot help but moan as I think to myself as I look down at my lacy socks and Mary Janes that I am really fucking like a woman.

I reach back and let his cock slide through my hand as he is fucking me like a girl.

He moans "I love fucking you Andrea, your pussy is so nice." His cock starts to firm up as he slides deep inside of me as it is pushing against my walls as he moans louder.

I tell him not to cum inside of me despite having a condom on.

Without a word, he stops deep inside of me as far as his cock will reach. I get pushed up against the wall as I feel his cock start spilling his cum into the condom deep inside of me. I can feel the burning warmth of his fluids against my insides.

He pulls out of me with his cock now half erect and pulls the condom off throwing it in the trash. "You're a woman now Andrea."

He quickly puts on his clothes and walks out the door leaving me wanting more and making me feel like a used slut discarded despite I gave him my body to satisfy his sexual needs.