I was in a great marriage. We got along, did fun things, and had a great sex life. My wife, Joann, or “Jo”, knew that I had cross-dressed when I was a teenager. I had told her how my sister, Maggie, had dressed me as a girl for a Halloween party when I was sixteen. I told Jo that she had done such a good job that almost everyone at the party thought I was a girl! One guy had even asked me why I hadn’t worn a costume.
I enjoyed it and asked Maggie if she minded doing it again. She thought it was fun, and told me with my height and build, I probably should have been a girl. After that, Maggie would dress me up and I would go shopping with her. It was confusing, but I liked it.
I told Jo I had stopped before we met. That wasn’t a lie. I thought it was just a crazy thing I did when I was younger. For some reason I wanted her to know, but I explained that I had put it behind me. Joann thought it was cute, and even said that I would probably make a pretty girl. I remember her saying, “We’re the same height and weight, and don’t take this wrong, but you have some very feminine features.”
Like what, I said. “You have great legs, you’re very thin and I’d kill for your eyelashes. You have very feminine hands and your Adam’s Apple doesn’t show at all. “If you grew your hair long, all you would need is tits.” We just laughed, but I always remembered those comments.
Even though we had been married for eight years, and I was now in my thirty-one, I found myself thinking about cross-dressing and how much I had enjoyed it as a teenager. I couldn’t get rid of the thoughts.
I decided to try it again. I figured it would be harmless. I had to find out why this desire was dominating my thoughts. I ordered things online and had them delivered to my office. In short order, I acquired a full female wardrobe.
I waited until Joann was gone on a Saturday and tried on my new things. It was surprisingly exciting and I loved the feelings it brought back. I started dressing every time Joann was out of the house for more than a few hours. This went on for a few months.
Nevertheless, I kept thinking the urge would just go away. But it actually began to become insatiable. I did a little research and found something called “Transformations by Jane.” It was a small business run by a woman out of her house. She advertised that she helped men “transform” into women.
I made an appointment on a Saturday when Joann was out of town for the day and night visiting a sick friend,
I drove to a house in a nice neighborhood. The woman who answered the door was a little older than me, attractive, and well-built. She introduced herself as Jane and invited me in. She told me not to be nervous, and that she had done this often and enjoyed meeting “girls” like me. She also told me that this was a process and her one requirement was that I do everything she told me to do. I agreed.
I informed her that I had brought lingerie, a skirt and blouse, and two-inch heels. I was interested in being fitted for a wig, having my makeup done, and doing anything else that she thought would help me be more feminine. Jane instructed me to go to a room down the hall and change.
I slipped on a bra, which I stuffed with a few pairs of my wife’s old pantyhose. I put on panties and a pair of thigh-high stockings. I put on a stretchy pencil skirt and a satin blouse. I put on the low-heel pumps. I took a deep breath and walked down the hall.
Jane looked at me. “That’s a nice feminine outfit. You are very thin with a slight build. You have far more feminine features than my average client. I think we can make you into a beautiful woman.”
I smiled. Jane told me to sit at a table she had ready. “We’ll start with makeup,” she said.
Jane carefully applied it. She made sure I understood every step. First, she applied concealer. She told me to always shave before doing my makeup. She did my eyes, applying shadow, eyeliner and mascara. With each step, Jane made suggestions as to appropriate colors and techniques. Finally, she did some blush and lipstick.
“I don’t want you to look in the mirror until we’ve picked out a wig,” she said. We talked about color and length. Then Jane brought out three medium-length, wavy wigs in different colors. One was a dark blond, another auburn, and the other brown. After trying each on, Jane thought of the auburn one because it came very close to matching my own hair. Jane showed me how to put it on and pin it in place.
“Now you can look in the mirror,” Jane smiled. She told me to stand up and turn around. There was a full-length mirror. I stared at the person in the mirror.
“Wow,” I exclaimed. I barely recognized myself. I was looking at a rather attractive woman.
“You do make a lovely woman,” Jane said. “Now let’s work on some other things,” Jane told me.
“Like what? I asked.
“I think we should talk about making your body more girlish,” Jane explained. “Given your height and build, I think you can easily pass as a woman. Would you like that?” She inquired.
“That’s my dream, Jane. Let’s do it,” I exclaimed. “So what do you suggest?”
First Jane asked what I used in my bra. I shyly told her it was my wife’s pantyhose. She giggled.
“Take off your blouse,” Jane ordered.
I unbuttoned my blouse and slipped it off, exposing the plain white bra I was wearing.
“That’s an ordinary bra. What size do you wear? Or perhaps I should say what size do you want to be?” Jane inquired.
I told her that the bra was a 36C, but that I was thinking I might like to be a D cup.
Jane got up and left the room. She came back with a bra and a small box. She told me to take off the bra and put on the one she had. The bra was much nicer. It had underwire cups and was very lacy. I slipped it on. Then she opened the box and took out two silicone breast forms. She slipped them into the bra.
“There. That’s better,” she said. “What do you think? She asked.
I admired myself in the mirror and felt them. They felt like real breasts. “I love them,” I exclaimed.
“Okay, we’ve done your makeup, your hair and your breasts. Let us continue.”
“What’s next?” I said excitedly.
“Now we will work on making the rest of your body more feminine.” Jane smiled.
Jane explained that what we needed to do was to narrow my waistline and widen my hips. She explained that we could do that with some shapewear.
Jane brought out some things. “This is a gaff, a waist cincher, and this is a special girdle with padded hips and butt.”
“Take off your skirt,” she ordered.
I stood up and pulled down my skirt. As I did, I realized I was very aroused. My erect cock protruded straight out of my panties.
“That’s not very feminine,” she giggled.
“I’m sorry Jane,” I blushed.
“No need to apologize. It happens with many of the girls I see. Although I must say yours is bigger than I’ve seen in a while. It’s quite nice.“ Jane smiled broadly.