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Wife's Crossdressing Fantasy

My journey from boy to man to woman
This is a work of fiction. Any resemblance to persons or incidents is coincidental.

My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making small talk... I guess to make me feel at ease.

We talked about many things. He told me I was cute and that if I dressed up I would look like a very beautiful girl. I didn't say anything about that, but I did think about it and it was exciting to think about it. Nothing else happened, but the seed was planted.

Most boys begin to develop masculine features at about age sixteen. I was not one of them. I was about to graduate high school and still I was slender, small and rather fragile looking. Because of that I always felt out of place and that is why the words of the dentist impacted me so strongly.

I couldn't stop thinking about what the dentist told me, so a few days later I took a pair of red panties and a red bra off my neighbor's clothes line. I put them on and the feeling was amazing. Looking at myself in the mirror I developed a sense of pride that I could look so good in the panties and bra. The dentist told me I could look like a beautiful girl if I dressed up and he was not lying. Somehow looking myself in the mirror made me feel really excited and good inside. That was my first time dressing up in girl's clothes and it changed my life forever.

I didn't dress up again until I was an adult. I thought I had outgrown such things and didn't think about it much. Then my wife went to South America to spend some time with her daughter. One evening on the phone she told me about a fantasy of hers where I was her slutty girlfriend and she was the man. When she said that I was so turned on and excited that I could hardly breathe. All the feelings I had enjoyed as a teenager dressing up rushed back and I knew I was about to confront my destiny.

I went out and bought a pair of red satin panties, and a red bra to match. I also bought red thigh high stockings and a red garter belt to hold them up. Over that I wore a schoolgirl miniskirt and a white blouse. To finish the look I had purchased a pair of rather large breast forms and a blond wig.

Just before she got home I dressed up in my clothes and applied some of my wife's makeup. I had been practicing the week before, so I would have just the right look when she walked in. When I looked in the mirror I can't adequately describe the feelings that coursed through my body. I was so excited. It was wonderful to me to look in a mirror and see a beautiful woman staring back.

I couldn't wait for her to come home and make me her woman. When she finally walked through the door and took one look at me she dropped her bags, held me in her arms and kissed me passionately on the lips. I was in heaven. She then told me to wait a minute and went into the bedroom. After a couple of minutes she came out wearing one of my suits and we started making out again.

I didn't know it, but she had purchased an eight inch strap-on and I could feel it pressing against me as she held me tight. She told me to turn around and she pulled my dress up to reveal my red satin covered ass, then started rubbing my cheeks. I was so horny from all this foreplay that I couldn't think of anything else but turning around and banging her right there. But then I felt her cock head touch my bare asshole. I hadn't realized it, but she had pushed my panties aside so that there would be easy access to my ass.

"I'm going to fuck you with my cock," she spat. And with that I felt her press forward. The tip pressing past my opening. I could feel that she had covered her cock with a lubrication and that helped her slide it in so easily. She had gotten inside me before I had a chance to protest, then commanded again, "Spread your cheeks for me, bitch," and with that I reached back and pulled my cheeks in either direction. "Oh, you want to be fucked like the little slut you are, don't you?"

I just waited silently. She was relishing this moment, so she asked again, "Don't you, whore?"

"Yes," I said softly.

"Yes, what?" she asked.

"Yes, I want you to fuck me," I obediently stated, very turned on by her dominant nature.

She pressed further in, aided by my spreading and slowly buried her eight inches all the way to the base. "That's a good little slut," she proudly said. She held herself there for a moment, enjoying the control she had over me. Then I felt her pull back out, put her hands on my hips, then glide back in to the hilt. She continued this for what seemed like an hour.

She had both hands grabbing the bunched up mini dress that was above my ass. All the while, I was so turned on that I could feel the pre-cum from my cock starting to flow into my panties. I couldn't believe it, but I was actually enjoying being her sexual toy.

She fucked me for several minutes, but it seemed like it only lasted a minute, or two. Then I felt her slowly pull her cock out and back away. I heard her walk to her bathroom, flush the toilet, then come back. When she came back she said, "stand up slut and fix yourself up."

I did as commanded and adjusted my dress back in place as I noticed she had gotten dressed again. I was now her bitch and I didn't want it any other way. I couldn't wait to feel her cock inside me again. Since that day I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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