Pretty in Pink Ch. 02

I could not believe my good fortune. Not only had Jessica accepted my crossdressing, she had changed her whole attitude toward my fetish. We talked about it afterwards and she told me she was continuing to research the topic. In the meantime she made me promise that we would have no more secrets between us. Over time, she got me to tell her the full extent of my fetish. This included me making myself up and going out on the town en femme.

I asked her what I could do for her to repay her loyalty and acceptance. She smiled and told me, "I guess I will need to think about that. It seems almost like a get out of jail card." We settled into a regular routine from that time on. We made love frequently the conventional way. However, we developed a code for my panty play. She would leave a pair of panties on the vanity top in the bath. One Friday evening when I got home from work, I found a pair of sexy peach colored panties in the master bathroom. She had written a note on the mirror. SEE ME BEFORE YOU DRESS IN THESE.

I dutifully went into the kitchen and asked her what the panties and note meant. Jessica told me to follow her back to the bathroom and she would explain. She lathered my balls and ass area with shaving cream and proceeded to shave my nether regions, moving my cock and balls as necessary. When she finished, she took out a depilatory cream and applied it all over my body except my face and hair. She told me to shave my face closely while I waited for the hair removal cream to work. Then she said to get in the shower after ten minutes. When I did, the hair on my body began falling down the drain. I was completely hairless below the neck.

I dried off and Jessica applied a highly perfumed powder to my entire body. She then slipped one of her sheer robes over my body and directed me to the vanity chair. She began to apply foundation to my face. I was a little surprised with this and asked what she was going to do. She said, "Dear, I have learned to accept that you have this fetish and you have shared all of your secrets with me. Now that I know what you like, I want to experience it with you. Besides, I know now how much it excites you and I realize that as long as we are open and honest, everything is okay."

She then proceeded to apply my makeup in a very professional manner. Her sculpting and combination of colors did wonders for my face. The heavy eye makeup made me look like not just a woman, but a slut. She giggled as she added the super long sexy eyelashes. When she placed a very expensive dark red wig over my head, I had become a woman.

"Now for the lingerie."

She pulled out a gorgeous wine colored garter belt, a wine colored thong, wine colored stockings, a matching bra, 38D and a pair of black stilettos. She told me to get busy dressing. "I know you know how to put all of this on." She wadded up several pairs of pantyhose to stuff my bra. "This will have to do until you get your new breastforms." Finally, she pulled out a very sheer, very black duster that tied just below my breasts and flowed to the floor.

Jessica stepped back and looked at her handy work. "My god", she said, "Look what a hot bitch I created." "God you look better than I do."

She had me walk around and model before her while she complimented me at every turn. As she fawned over me, I became more confident in my walk and my turns. I swung my arms as she instructed and strutted like a runway model. She whistled every so often and told me how hot I looked.

Jessica then said, "Okay, girlfriend, why don't you go pour us some wine while "Momma" gets her ass ready. I'll be damned if I am going to let this new hot bitch upstage me."

Jessica came out of the bedroom dressed up in a black teddy, red stilettos and equally slutty makeup. Her hair was freshly rolled and sprayed with lacquer. She wore bright red lipstick with a little outliner for a more dramatic look. She came out and hugged me, pressing her ample breasts into my stuffed bra. She took her wine and we retired to the couch. I looked her over and said, "You look hot."

She replied, "No, lover, we look hot."

"Why don't you tell me how this makes you feel?"

I searched for words. I told her that I felt loved and accepted. I loved her so much for her thoughtful respect she was giving me. I was so turned on sexually at her creating my new feminine persona. My cock was as hard as a rock wanting to make love to her.

Jessica told me that the act of her making me up and adding all the frilly touches that I could not envision myself made her very excited. It was like a challenge to make me look exactly like a woman. She knew that it was exciting to me, but she had not figured to gain so much satisfaction out of this.

I sighed and asked, "What do we do now?"

She answered, "Well, why don't we take our wine to the bedroom and see what comes up?"

She reached her hand to me and I took it. She immediately dropped my hand and proceeded to show me how a woman would respond to the extended hand of a lover. She critiqued my walk to the bedroom and had me do it over again. Walking in the heels was awkward, even though I had practice, but Jessica instructed me how to pivot a little to allow my hips to rotate. She said that we could look at some shapewear together and get some ordered if we were going on a lesbian date together. I was shocked at this and told her so. She said, "Oh, really, honey, I spent all this time getting you ready for this and you are not going to spoil it for me. You are going to practice until you walk right and talk right."

"But tonight, dear girlfriend, you are going to make love to me with your mouth and then your girl cock until I have cum all I want."

In bed she removed her panties and lay back on the bed. She beckoned me with her fingers and pointed to her shaved pussy.

"Suck my pussy, bitch."

I moved gently to her crotch and flicked her clit with my tongue. My lipstick smeared all over her pussy as I engulfed her with my painted lips. I gently spread the petals of her vagina and inserted my tongue into her nectar pot. She was coming and secreting. I poured my saliva into her pussy and sucked her girl cum out into my mouth. Over and over, I licked and sucked her, bringing her to a series of shuddering orgasms. She moaned and bucked her hips. With a little squeal, she convulsed one last time and then went limp. I laid my head on her wet pussy and felt her heart beating through her insides. We lay that way until she stirred and told me to move up in the bed.

She removed my thong. My little cock was hard and she invited me into her pussy. "Come here girlie, put your girl pussy into mine and fuck me."

"Stick that pussy into me as deep as you can and shoot you lady cum into me."

I actually envisioned having a dripping pussy and bumping my cunt into hers. I moved side to side grinding my boy pussy against hers. I was trying to be a good lesbian lover to my gorgeous wife. We were dressed almost alike and looked almost alike. I wanted to share my new pussy with her. She looked into my eyes and said, "sucking my pussy has ruined your lipstick, honey, now bump my cunt with your girl pussy."

She kept saying what I was feeling. I began fucking her with my girl cock until we both came in a vigorous climax. She then guided my girl face to her cummy pussy and fed me my girl protein drink. I ate all my cum from her and sucked her to yet another shuddering orgasm.

After we rested she said, "Wow, I might have lost a good husband and found a better wife."

Now we were on the same page. Not only had I gotten out of my mess, but we were moving into an area of our marriage that had been impossible with all of my secrets. It was like a weight removed from my shoulders. Over time, dressing up while I was out of town became much less exciting. I became more focused on my work and my accounts. I was now wearing feminine lingerie exclusively and I kept my whole body hairless. Instead of dressing up and driving aimlessly around a city, I learned to relax more at my hotel. I lounged in baby dolls, corsets and gowns when I was off. I could now paint my toenails and shape them in a more feminine way. I paid careful attention to my feet. I used all the feminine foot care products that I could find to make them soft and pretty.

Jessica suggested that I permanently remove my body hair by laser treatments. Even if I grew tired of crossdressing, the hair removal would be okay. Some guys have little or no hair on their legs due to a variety of reasons, so it would not be a clear signal of anything. We invested in a home laser to see if we could save some money. It was expensive, but the salon treatments are exorbitantly expensive. With repeated treatments my fine hair started falling out and not coming back. I grew the hair on my head long. I could style it when I dressed and still comb it when I was working. We used mostly wigs when I dressed fully.

When I was at home or in the home office, we almost always dressed for sex. Sometimes when we were busy but still wanted to make love, I just wore panties or an assortment of other lingerie. Those times we did not even do makeup.

We continued dressing up to make love quite frequently. The signal for this would be for her to leave out my complete wardrobe, makeup, fake lashes and press on nails. When I saw all of these things I knew I was going to be a lesbian that evening. Often I would dress on Friday night and stay en femme all weekend. We were close to going out driving, but not ready to go out to restaurants. Jessica kept on grooming me tightening up my walk and mannerisms. We had such a great time doing this. It was our real recreation during this training time,

One Friday at noon, Jessica called me and asked if I wanted to go out of town for the night. I was fine with that. We sometimes drove to some neighboring cities just to do something different. I did not quite put everything together until I got home. Jessica told me that we were already packed. All I had to do was get ready myself. Upon entering our bedroom, I saw a complete set of clothing including lingerie, short skirt, thin blouse and five inch high heels. A blonde wig was on the bed. I already had made sure my whole body except for my head was clean as porcelain. All I had to do was shower.

Jessica was waiting with a robe and slippers when I dried off. She dusted me with bath powder and spritzed me with enough perfume that I could be smelled for half a block. She sat me down at the mirror and did my makeup. I looked great but not real slutty. I put on the bra, breastforms, gaff panties, short skirt and thin blouse. We had already done my chest to add cleavage above the breastforms. I had a nice look of a hot woman. She helped me with the garter belt and hose, then carefully placed the blond wig on me and adjusted the hair just so.

Jessica told me that we were taking my Camaro instead of her sport SUV. She would drive while I sat in the passenger seat. We had a two hour drive to our destination. When we reached the freeway, she invited me to slide my seat back a little so I could stretch my legs out. Once we got on the open road, we attracted plenty of attention. Jessica was dressed very similar to me except that she wore a tight low cut top with a balconette bra that thrust her already magnificent breasts up even more. She was stunning. We looked like two hot girls out looking for some cock.

The truckers especially had a great look at our legs. After about twenty minutes, Jessica told me to open a couple of buttons on my blouse so that some of my manufactured girl boobs could show a little. Jessica had contoured my created cleavage with makeup so that a little looked like a lot. I was amazed when she had started creating my boobs using all the tricks. She told me that calling me by my male name in public was not going to work, so she changed Brian to Brianna. She assured me we were going to be safe and conservative, but that we were going out in public. Then she said, "Brianna, how about showing a little of those garter belt straps to our many admirers."

I slowly hiked my short skirt a little higher so the tops of my stockings and the garter snaps would be visible. Jessica had always bragged on my legs since we had been dressing up. She said that mine looked almost as good as her very sexy legs. She told me that driving like this was perfect because we were far enough away that I would have no fear of people looking too close. Beside, she assured me that I was a crossdressers dream. PASSABLE. I thanked her for her confidence, but still had some nervous doubts.

She said, "Well, Brianna, you are not exactly muscle bound. You are shorter than me. You have long flexible muscles in good condition. Your cock is all gaffed in. Your makeup is simply gorgeous. Your hair matches the makeup and foundation. What more could you ask? And by the way you are with a super hot wife, excuse me, "friend", who attracts plenty of attention, anyway."

We pulled over to a rest stop about an hour out of town. Jessica said, "Brianna, honey, we need to go to the restroom." I was too nervous to pee, but Jessica told me to go in, sit down and squeeze a few drops. We took our time walking to the ladies room. She told me that if we encountered any women on the way, to make sure that I smiled and looked them straight in the eye. She said, "People can read your body language. Don't look like you have anything to hide and no one will be the least suspicious. If you avert your eyes, they will have a chance to look for anything out of place."

We did indeed encounter several women on the way there and back. Most looked like tired travelers and we looked like two hot chicks out on the make, but we did not look like a crossdresser and his wife sneaking into the ladies room. We took adjoining stalls and I heard Jessica peeing. I squeezed out a small stream, then took some toilet tissue and drained my soft little cock so I would not mess up my tight gaff panties. We stopped to wash our hands and then took some lipgloss out of our purses and touched up our lips. Then we were out and back to the car.

I was dizzy with excitement when I got back into the confined comfort of my car. We continued on teasing anyone who cared to look into my low riding sports car. By the time we reached our hotel, we were both showing our panties as well as garter belts. Jessica was showing plenty of cleavage while I was showing my manufactured push up cleavage.

Jessica had guaranteed our suite with a credit card, but she wanted me to come into the lobby also. She had prepared me on the drive over on being seen but not necessarily noticed. Of course, the way we were dressed called enough attention to us. As Jessica checked us in, I browsed the local advertising folders. At least I was trying to give that impression. We did not notice any raised eyebrows for the desk clerk. We went back outside to pick up our bags and then came back inside. We went to the elevator and rode to our fourth floor room. I was wondering what was in my suitcase.

Jessica asked me what I would like for dinner, even though it was still a little early. I was not really hungry. The excitement of being out dressed for my first time seemed to kill my appetite. We discussed this, with Jess finally deciding on Chinese buffet. She said we had to order less plus we would make repeated trips to the buffet. Since this was our only plans for this outing, she reasoned that I would get plenty of practice walking and practicing my gestures while taking small portions and returning frequently.

In the room, she pulled out a bottle of scotch and told me, "Brianna, sweetie, I think we need some ice. Will you be a dear and fill our bucket?"

I knew that was designed for me to get outside on my own. I took the ice bucket and opened the door. I walked leisurely down the hall to the end where the ice was located. I was wondering if I could make it there and back without encountering anyone. However, just as I passed the elevators, I heard the bell ding. The door opened and a thirty-something couple got off. I did not look, but heard them talking. They fell in about ten feet behind me. Now I was sweating bullets. I was sure that they would recognize that I was a man as soon as they saw me walking. I heard their conversation as they continued to count room numbers. I got the ice bucket filled and when I started walking back, they were still fumbling with the key card. As I neared them the woman told the husband to give her the card. I smiled and looked her in the eyes. She said, "He can never use these room cards." She smiled and winked at me as the man made a face and looked at me also.

That was totally invigorating. I seemed to have passed my first face to face encounter. When I got back to the room, I rapped gently on the door and Jessica quickly opened it.

"How did it go?"

"I met a couple getting off the elevator and they walked behind me to their room. Then I met them face to face on the way back and they did not register any surprise."

"Fantastic, sweetie, I knew you could pull this off."

She grabbed my head and gave me a big sloppy kiss. Our lips meshed smearing our lipstick. She reached around and pulled my ass to hers and we kissed some more. Jessica fixed us both a scotch to calm my nerves. I was getting more and more in my comfort zone. We hung out for a while and talked about my presentation when meeting people. Jessica suggested that we freshen up our makeup and then go out for dinner.

We had located a nice looking Chinese restaurant. When we arrived, I was feeling more confident, but still a little apprehensive. The hostess seated us and the waiter came and took our drink order. I was careful not to overdo my female voice and spoke calmly like Jessica had instructed. She suggested that I go to the buffet first while she watched. I walked demurely and took a plate, making sure to use my body language to spoon the food. Jessica came by me and whispered, "You are doing great, baby."

During the meal and repeated trips to the buffet, Jessica critiqued my movements. She was so positive and encouraging. I was learning to relax more and the mannerisms were becoming more natural. We talked and laughed as we picked at our food. Jess suggested that I go to the ladies room before we left and touch up my makeup again. She assured me that I still looked great, but that was a ritual that all well dressed ladies did. She told me that she was completely surprised with how much fun this was for her. She never dreamed that my little fetish, when shared with her, had become a fetish for her also.

Everything went far better than I had expected and by the time we returned to our hotel, I was feeling in the mood. Jessica was also. She suggested that we have a glass of wine, shower, redo our makeup, and get into our lingerie. I was feverish to see what she had packed for us. After my shower, I shaved again very closely and put a stocking cap on my head. Jessica came out of the shower and told me to use the dusting powder and perfume. She said that I could go ahead and start placing my foundation, eyelashes, mascara and such on while she did her makeup first and she would add the finishing touches to mine. I was getting better at applying the first layers of makeup now that we had done this several times.

She came back in the living area with a real "late evening" makeup job. It included extra eye liner, a little more color in the cheeks, very deep colored eye shadow and colored liner, and of course dark purple lipstick. She approached me and said, "Let's see, Brianna, how well you have started. Yes, very good, let me add some finishing touches and I think we will have two hot sluts ready for some lesbian action."

After adding the slut additions, I was hot as fire and ready for her. She went over and handed me a suspender pantyhose, black crotchless panties, a black demi-bra, A- cup with no padding. She added a pair of latex bust enhancers which gave me just the slightest rise in my man breasts. We followed with black stiletto heels and a dark brunette wig. She had me stand in the middle of the room and then place a black, very sheer gown over me. Stepping back, she exclaimed, "Very hot girlfriend, except for that hard little cock. I guess I can overlook that since you are a hot slut in every other respect."