Wife Helps Me Date As A Girl Pt. 01

My wife Joy was 50 years old and I was only in my late 30's. We had been married for 15 years when she came to me with a surprising request. We had just finished having sex, or should I say working to have sex, when she said;

"It's becoming difficult for us to enjoy the act of sex. I'm finding it uncomfortable. What would you say if we just stopped trying to have intercourse?"

"You know I've always loved you. I still do. Are you sure this is something you would want?" I answered.

"It's something that would make things much easier for me. I know it's a lot to ask, and I still love you very much, but this is something I think we should do." Said Joy.

My wife worked full time as a makeup artist at a Hollywood studio. Sometime her hours were long and on the hectic side depending on the shoot she was working on. I was a little let down by her request, but she was a wonderful partner in every other way so I agreed to her request.

What I had not told my wife when we married was that I enjoyed dressing up in pretty lingerie. I had a box of it hidden in the garage. Having regular intercourse with my wife had caused me to not think about my stash, but since sexual intercourse was not going to be possible going forward, I thought it was time to again visit my lingerie collection to help relieve my needs.

I was able to settle into my life in a comfortable way for the next few months and then I wanted to push things a little farther. I looked online and found a site for crossdressers. This site allowed one to post pictures and to meet people who were interested in getting together. I used some of my wife's make-up she had around the house and took photos of myself in full make-up and wearing a wig while in some of my pretty lingerie. The photos looked very attractive.

It did not take long at all for me to get messages on the web-site complimenting me on my photos. I was fairly surprised as I had taken the pictures without much thought. There was more than one man who was very nice a polite and wanted to know more about me.

I found the interest of males more exciting than I had anticipated. I began more than one email discussion with the men I found attractive. This type of communication went on for at least another five months.

One day, I walked into our home office and my wife was standing there in the middle of the room.

"My computer went on the blink and I had to use your desktop yesterday." She said.

"That's okay...Did you get done what you needed to do?" I asked.

"I did...But that wasn't the point. I saw your emails from what looks like male admirers. And I followed them to a crossdresser web-site it looks like you belong to." Said Joy.

There was no sense hiding this now, and I decided to take a bit of a defensive stand; "That's right...I need some sort of release if you and I are not going to fuck anymore." I said with authority.

"Relax...Don't be so defensive. I saw your photos on your profile and you have a really cute look. Do you like dressing up as a girl?" She asked.

"It's fun...and it's a release I find somewhat harmless." I replied.

"Would you like me to help you with your female look? I know how to do that I'm sure you're aware." Said my wife.

"Is it something you would want to do?" I asked.

"If you want me to, I'd be happy to help. We could take some good looking photos for your profile."

"What do you have in mind?" I asked.

"Whatever you want; what type of a female look do you like? Nightclub Slut or Girl Next Door?" Asked Joy.

"I like the Girl Next Door look." I said without hesitation.

"I can do that for you. But first, I want to hear you say you want me to dress you up like a girl. Say it out loud." Said my wife.

"Joy, I want you to dress me like a pretty girl, and I want you to teach me how to behave like a good girl." I said in a strong, loud voice.

"Okay then. Let's get started by measuring your chest size. I'll bring you home some silicone breast forms and get you some bras to wear. Do you like lace on your bra?" Asked Joy.

"Yes. As much satin and lace as you can find. My nipples are ultra-sensitive to the touch and I love the feeling of the satin and lace on them."

"The breast forms may cover that up, but we'll find a way to make you happy. Strip naked for me while I take some measurements." She replied.

I quickly did as she asked and she took my chest measurement.

"I think you would look very Girl-Next-Door with a 38C breast size. It will be large enough to give you a feminine shape but not too large to look fake." Said my wife.

"Whatever you think, I will follow." I answered.

"And what about body hair? You have never been very hairy, but to fully assume the role of a girl, I think I want to shave off all your body hair. Underarms, chest, legs, and your pubic area. You will really love the feeling you will have wearing your pretty lingerie when your body is totally smooth."

"That sounds perfect. Will you help me shave so I know it is done correctly?" I asked.

"Of course baby. Let's get you into a warm bath while I make a list of things I'll need and when you get out of the bath, I'll shave you down completely." Said Joy.

The hot bath got all my body hair ready for shaving. When I dried off Joy had me lay down on a large towel on the bed and she applied a large amount of shaving gel to my body. With a woman's razor, my legs, underarms, and chest were fully shaved in no time.

"Now let's shave you clean between your legs. How are you feeling where I have already shaved?" Asked Joy.

"I feel very smooth and very feminine." I answered.

"Perfect. Now let's get rid of that clump between your legs." Said Joy.

She was very delicate and deliberate in shaving my pubic area, and in about ten minutes, every hair between my legs was gone.

"You know something...Your little penis looks a lot smaller when the hair is removed. That should make it much easier for you wearing your panties. I noticed you did not get hard when I was shaving you; was that on purpose?" Asked Joy.

"I really focused on my feminine thoughts and on being the best girl I could be. When I did that, all male sexual stimulation shut down. I think I'm really a natural at being a girl." I said with a smile.

"I think you are too. And when I get home tomorrow I'll have all sorts of things with me that I'm sure you will love. Would you like to wear a nylon and lace nightgown to bed tonight? With panties on underneath of course." Asked Joy.

"I would love to. I'm anxious to feel the nylon and lace against my smooth, soft skin." I answered quickly.

I had trouble sleeping that night as the panties and nightgown I was wearing felt so wonderful. Most of the next day, I spent wearing just my panties, a training bra, and a full slip around the house. When my wife got home from work she had several items ready for me to wear and she was ready to give me a full make-up session to see how pretty she could make me look. The results were shocking.

"I've talked to a few of my co-workers about what to do and they are telling me to have you fully dress as a girl except for your wig before I do your make-up. That way, the look will be something much easier for you to accept." Said my wife.

"You told your co-workers about me?" I said quickly.

"Not about you specifically; I just said I had to do so work on the side and I asked for their direction." Answered Joy.

It took about an hour for my wife to put on my make-up. Eyelashes, painted fingernails and toenails, lipstick in a very pretty shade of pink. When she was done we put a shoulder length wig in place and I looked in the mirror to see the most beautiful "Girl-Next-Door" I had ever seen.

"My God...You are beautiful!" Said my wife.

"You did a tremendous job. There are no visible signs of me ever being a male!" I said with a huge smile.

"Let me take several photos of you from all angles. And let's take some sexy ones with you just wearing your lingerie." Said my wife breathlessly.

I let her take at least 100 photos in all types of poses, from fully clothed in a pretty dress all the way down to wearing only my bra and panties. Every photo showed me to be a complete female without any trace of anything male about me.

"We should post these photos of you on your crossdresser profile, and add the invitation that you are interested in finding a male to date. It would be interesting to see how many would reach out to you." Said Joy.

"I would find that interesting too! Good idea. Would you be okay with me going on a date with a man if you helped me prepare to be as feminine as I can be?" I asked.

"It sounds very sexy to me and I would love to help you prepare." Said Joy.

The two of us posted the new photos and then wrote on my profile that I was looking for a gentle, caring man to start a dating relationship. I was hoping some of the men I had been communicating with would express interest, and in less than three hours my wish was fulfilled.

One of the men I had been sharing emails with, and who lived in our same city, said he was very interested in taking me out on a date. He was married, but he said his wife was okay with him dating a girl like me. The phots he sent showed him to be very handsome. As a girl, I was very drawn to him.

"Is this guy, Bob, someone you would like to date?" Asked my wife.

"I would like to try. He is very handsome, and he seems like a kind and gentle person."

"Then I think you should tell him you want to go on a date with him." Said my wife Joy.

"And if he says yes, you'll help me dress and be the most feminine I can be?" I asked.

"Of course I will, and that will not be hard to do. You are so naturally feminine I can't believe you have a penis between your legs." Said my wife.

I emailed Bob that I would be interested in a date with him. I told him I would like to enjoy a romantic dinner with him and he agreed. Our date was set for the next week. My wife came home with three or four dresses she thought I would like that would flatter my shape. She also put forth the idea that I should think about using surgical glue to attach my breast forms to my body. She said it would allow me to practice my posture with two round breasts on my chest. I agreed to let her position them on me. I stripped naked and lay on the bed as she got ready to attach them. My wife was always fully clothed when she feminized me as I was fully naked.

"When I glue these in place, they will cover your natural nipples. Didn't you tell me your nipples were extremely sexually sensitive?" Asked my wife.

"They are. My nipples get hard and erect when I am turned on and my little penis stays limp." I replied.

As my wife was standing next to the bed looking at me lying there nude she asked;

"Can I lick and kiss your nipples before I cover them up? I'd like to see them get hard, and see your little penis stay soft."

"Go ahead. I'll have a fully female response to your actions. Since you and I have stopped fucking, the only way I can stimulate myself sexually is as a girl." I replied.

My wife leaned down and licked and gently sucked on my nipples and they immediately grew large and round as I let out a little gasp. My tiny penis, not only stayed limp, it actually pulled back inside my body. When she was done, my wife looked me over and said;

"You're right. All of your sexual responses are female! You are so pretty."

"I know you married a husband Joy, but I really love being a girl." I said softly.

"That's okay honey. I'm enjoying turning you into a girl." Said Joy.

The evening of my date arrived and my wife had come home early to help me prepare. I wore beautiful stockings attached to a satin and lace garter belt. My bra and panties were full of lace, and I was allowed to wear a half-slip and camisole under my dress. My hair and make-up looked perfect, and I was a complete female waiting for the doorbell.

When my date arrived, my wife introduced herself and then introduced me. I was instantly taken with how handsome Bob looked and I was thrilled to be going out on this date.

"You two have fun, but get her home before midnight if you can." Said my wife.

"I'll do whatever she wants." Answered Bob.

Bob was a complete gentleman on our date. He opened the car door for me, ordered dinner for me, and we had a totally enjoyable time talking and getting to know one another. I was impressed he had four kids with his wife as it meant he was very sexually active with her. I was also impressed how I did not have any type of a male sexual response when I was with him. My only sexual responses I felt were female in nature. My tiny penis pulled way back inside my body and when I excused myself to go to the bathroom, it was a necessity that I sit down to pee.

After dinner he took me to a favorite bar of his and we sat together in a romantic booth and shared after dinner drinks. As we were sitting next to one another, with the table at the booth having a long tablecloth, I felt his hand on my leg which I let him do, and then a few minutes later he began to slide his hand up my stockings and under the hem of my dress. I politely stopped him from doing this and asked him to take things more slowly. To my surprise, he agreed, and said he could not wait for a second date with me.

"Would it be okay with you if we just kissed tonight and saved our intimate sexual contact for our second date?" I asked.

"I am so turned on by you, you cannot imagine. But the thrill of waiting and the anticipation is something I think would add to our second date." Answered Bob.

"I'm so happy to hear you say that, and I too will be anxious for our second date." I answered as I leaned into him and we shared gentle tongue kiss.

When my tongue met his I experienced a feeling deep inside my body that had never happened to me before. I felt a burning warmth welling up inside me. But to my great relief, no sign at all of an erection, or even a plumpness in my penis. Bob drove me home and we again shared a tongue kiss in the car before I got out. We agreed on a second date just six days away. I did not tell him, but I could hardly wait for those six days to pass. It was just before midnight when I opened the door to the house. My wife was waiting just inside the door and wanted to know every detail of my date.

"Did you have a good time? Was he a gentleman with you? Did he try to have sex with you?" My wife asked quickly.

"Slow down...Why don't you follow me into our bedroom and I'll tell you all about it as I undress for bed." Was my answer.

"I want to know every detail." Said Joy.

My wife was wearing a pair of cotton pajamas. There was nothing sexy about them. She put one leg under her and sat on the bed. I backed up to her and she helped me un zip my dress. I stepped out of my dress and went into the walk-in closet and hung it up while I was wearing my pretty half-slip and camisole. I came back into the bedroom as my wife was staring at me.

"So did you have sex?" She asked.

"No, I just let him kiss me in an intimate way." I answered.

"Did you let him fondle you?" She asked quickly.

"He tried to put his hand up under my dress, but I politely told him no." I answered.

I lifted my half-slip up to my waist which exposed the hooks of my garter belt holding up my stockings. I gently unhooked the garter belt from the stockings and rolled them off my completely hairless legs. I followed this by unhooking my garter belt and letting it fall to the floor.

"So are you going to have another date with him?" Asked my wife.

"Yes. We're going to go out next Saturday." Was my answer.

"That's perfect. I'll make sure you are looking your best." Answered Joy.

I lowered the straps of my camisole and let it fall to the floor as I stepped out of it. Then I lowered my half-slip to the floor and stepped out of it too. I picked up both items and folded them neatly. All this was done under the watchful stare of my wife.

I reached behind my back to unhook my bra and as I did this a wave of modesty came over me. I had been fully nude in front of my wife many times and she had shaved my body hairless more than once, but for some reason I felt like I wanted to hide my nakedness from her. As I let my bra straps down I put my hands over my breasts to hide the nipples. I did this even though I had surgically glued on silicone breasts. I was fully naked except for my full cut nylon and lace panties. I stood silently for a couple of seconds and then, holding my hands over my breasts, and having no sign at all of a penis in my panties I said to my wife;

"Don't take this the wrong way, but would it be a problem for you if I began sleeping in the guest bedroom?"

"All the time? Or just for tonight?" Asked my wife.

"I think I need to do it all the time. Since we're not going to fuck anymore, I can move all my lingerie into that room and my dresses into the closet. I would like to remember my date tonight when I get into bed, and knowing you were in the bed next to me just doesn't seem right." I said looking down.

"Sure honey. I want you to do what you think is right." Said my wife.

I put on my long nylon and lace pink nightgown leaving my panties on and my wig and my breast forms. I was looking every inch a pretty girl and my wife was in cotton pajamas. It was quite a contrast.

"I took a big step tonight and I discovered I really enjoy being a girl on the arm of a caring man. I want to remain dressed as a girl 24/7 from now on and I would like it if you only saw me naked when you helped me keep my body fully shaved." I told my wife.

"We can do that honey." Answered Joy.

"I'm going to bed now...Good night." I said as I turned to my wife.

She leaned in and kissed me on the cheek and at the same time I felt her cup my breast form through my nightgown. I didn't think anything of it at the time, but I would soon learn why she had done this.

I turned out the light and slipped into bed and spent several minutes recalling the wonderful date I had experience that evening and looked for with excited anticipation to being a full-time girl and having a loving relationship with my new boyfriend.

On our second date my wife helped me look my girly best and when Bob picked me up I told my wife not to wait up. Bob took me to the romantic bar first and we sat in the same booth and shared a couple of drinks before he again slid his hand up under my dress. This time, I did not stop him.

"I've made a reservation at a beautiful hotel suite. Will you join me there?" Asked Bob.

"I would love to." I answered immediately.

Our room was a very romantic bungalow room with its own fireplace, that Bob had made sure was on when we came through the door. There was a very nice living room with sofa in front of the fire. A bottle of champagne was chilling in the kitchenette. Bob poured us a couple of drinks and we began a long and intimate tongue kissing session. I was about to make love to a man for the very first time in my life and it felt like the most natural thing in the world for me to do.

As we were tongue kissing, Bob ran his hand up under my dress and brushed the front of my panties. I immediately responded by putting my hand between his legs over his pants and felt his manly sized penis growing bigger and harder as I stroked it through his pants.

"Oh baby, I am so turned on by you. I love it that the front of your panties is perfectly flat. You are such a pretty girl." Said Bob.

"I've never done this before Bob, but I can't wait to make love to you." I moaned.

"Have you been a good girl since our last date? Have you only been wearing your girl clothes?" Asked Bob.

"I have only worn panties and bras and slips and dresses since our first date. I knew you would want that." I answered.

"And you haven't been fucking your wife have you?" He asked.