Bob Returns To Crossdressing

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.

Jane went on, "You need to get rid of that. And it doesn't look like it's going away soon," she giggled. Take care of it so we can continue."

I realized she was telling me to masturbate. "I'll go in the bathroom," I volunteered.

Jane smiled. "That won't be necessary. I enjoy watching. Just do it here."

I smiled and took my stiff cock out of my panties. I started stroking it while Jane watched. I found it incredibly arousing that she was watching me.

She got up and went to the kitchen, quickly returning with some paper towels.

I stroked my cock while Jane watched. We chatted about female clothing styles while I stroked my throbbing cock. That in turn caused me to become increasingly aroused. It didn't take long before I was about to cum. "I'm going to cum Jane," I said.

Jane held out the paper towels. Within seconds, I started spurting cum into the towels. As I finished, Jane took a tissue and cleaned off my cock.

"That's a good girl. Let's get on with your feminization."

"First of all, these panties will give you the appearance of a vagina. It is called a gaff. Please put it on and tuck your penis and balls in."

I slipped on the tight panties and tried to tuck my cock and testicles between my legs as instructed. I was having trouble getting everything situated properly.

Jane asked if I minded if she helped. "Not at all," I responded.

Jane slid her hand into the gaff and carefully pushed my balls into the cavity below my penis. Then she reached behind me and grabbed my now flaccid penis and pulled it so that the head was almost tucked into my ass crack. Finally, she pulled the gaff up towards my waist.

"There you go. That's how you do it," Jane said.

I looked down and realized that my crotch was appropriately smooth. I smiled.

Jane then gave me the special girdle. She helped me put it on. The padding gave me much wider hips as well as a much fuller ass. It was quite tight and clearly thinned my waist. She handed me what she described as a high-waist, open-bottomed waist cincher. Jane placed it around my waist and fastened the many clasps. There were six garters dangling from the bottom of it.

Jane handed me a pair of lace top stockings and told me to take off the thigh highs and put them on.

I was feeling very feminine. I then slipped on the skirt and blouse I had brought. I sat and slipped on my pumps.

Jane smiled approvingly. "Now you're becoming a woman," she said.

I looked in the mirror. She was right. I looked like a woman.

"Well, what do you think? Jane asked.

"I love it," I responded.

We then spent some time talking about how to act like a woman. Jane instructed me on how to walk, how to sit, how to carry myself, and how to speak in a more feminine tone. This instruction continued for two hours. The more we talked, the more I knew this wasn't going away.

Jane smiled. "Now, for your next step. My husband will be here soon. He adores girls like you. He will be part of the feminization process. Just trust me"

I didn't know what to say. But I liked the idea of a man seeing me like this.

"I can't introduce you as Bob. You need a feminine name. Do you have one?"

"Well, no I don't," I stammered. But I do like the name Elizabeth. I think it's very feminine."

"I think you look like an Elizabeth," Jane responded.

"Okay. From now on you are Elizabeth."

This had turned out to be a wonderful experience. I didn't want it to end. Joann wouldn't be home until the next day, and I wanted to be like this for as long as I could.

Just then, the front door opened. In walked a very attractive gentleman.

"Hi Jim," said Jane.

"Hello honey," Jim responded. "Who's the pretty lady?"

"This is Elizabeth. Isn't she beautiful?"

"Lovely," responded Jim. "Nice to meet you, Elizabeth."

I was tingling inside. A nice-looking man addressed me by my new feminine name and said I was lovely.

I couldn't have felt better. We all had a glass of wine. Then Jane instructed me to sit next to Jim on the couch.

"This your next lesson. You need to learn how to be with a man," Jane said firmly. "Jim, take over."

My mind was spinning. I thought I was just going to dress up. But something about this seemed right,

Jim told me to move closer. He put his arm around me. "Elizabeth, you are really a beautiful woman. I want to see you again."

"Thank you, Jim," I said in my most feminine voice.

Jim pulled me to him and kissed me. Jane cut in. "Elizabeth, pretend you've just met and Jim has invited you back to his place. You like him. Just be the woman I know you are."

Jim kissed me again. This time, I kissed back. We started making out. Our mouths opened and my tongue met his.

"Good girl," Jane said. "Now think like a woman. What would a woman do?"

We kept kissing. I reached down and started rubbing Jim's crotch.

"Excellent," Jane said. "Keep going."

I was feeling like a woman. I pulled down Jim's zipper and undid his belt. I unbuttoned his pants.

I was thinking, "What am I doing?"

But Jane kept encouraging me. Jim pulled down his pants and his Jockeys. He had a big erect cock.

I instinctively took hold of it and started stroking it.

"Oh Elizabeth," Jim said as he kissed me again. He took my head and lightly pushed it towards his throbbing cock.

I briefly turned and glanced at Jane. She smiled and nodded.

I took him into my mouth. Jane excitedly said, "You're doing great, Elizabeth. You're a beautiful woman. Now finish your womanly duty."

For someone who had never had a cock in her mouth, I seemed to know what I was doing. My lips slid up and down his long shaft. After a few minutes, I felt him tense. He pushed his cock deep into my mouth. He groaned and released a torrent of warm juice into my mouth.

"Don't stop yet," Jane instructed.

I keep sucking until I knew Jim had no more to give. I lifted my head, letting his cock slip out of my mouth.

"Now swallow it," Jane said. "A woman should always swallow."

I did as told.

I sat up. Jim told me I did a great job. Jane said, "How do you feel, Elizabeth?"

I thought for a moment. "Very feminine, to be honest."

"That's wonderful. The lesson was successful."

I thanked both of them for the lessons. Jane asked if I needed to change. I asked if I passed well enough to drive home as I was. They both responded "Absolutely!"

Jim told me I was probably the most passable client Jane had ever had. I felt wonderful.

Jane gave me her bill, which was very reasonable. "And here's a couple of gifts."

Jane handed me a purse and told me to put my makeup on it, as well as my wallet.

"And here's something to wear home."It was a cute dark pink jacket."

Finally, Jim said, "If you want to practice giving head, come by anytime." We all giggled.

Jane added, "Yeah, and that's free." We all laughed.

I left feeling confident as a woman. I knew this was something I couldn't stop.

I knew I had to tell Joann. But how?