tagTranssexuals & CrossdressersTransformation Ch. 02

Transformation Ch. 02


When we woke we had a light snack and then the process of getting me ready to go out to dinner began. First we shared a warm bath complete with bath oils. Lovingly we washed each other, caressing the dirt away. Finally when the water cooled we dried and powdered each other, Cat showing me by example how to do it.

She asked me to go to her dresser and get two pair of panties. When I asked which ones she told me to chose, a pair for her, and one for myself. I looked through her panties like a seven year old at the candy counter and finally settled for a pair of red and black boy shorts for me. As I lifted them carefully from their place I spotted a pair of black and red ones. I couldn't resist the symbolism and took them for her.

"Perfect opposites!" I told her as I handed her the black pair.

She guided me to her vanity and once again began to make me into the female version of myself. We did the hair first, curling and blowing and fluffing until it was just right. With each step she showed me what she was doing and even had me try to duplicate some of her moves.

She looked at my face, evaluating the situation.

"You have a great face high cheek bones and a button nose. There is really nothing much we need to do, but.."

"But what?" I injected.

"Well you have a few stray eyebrow hairs that really should go."

"So what do you do, shave them off?" I asked.

"Well, we could do that, but the right way is to pluck them."

"Ok, so pluck them." I said stupidly.

"I have to warn you, it hurts like a bitch," she said with her usual laugh.

She stood in front of me, her bare breasts right in my face as she reached with tweezers to shape the first one.

"OH Shit!" I hollered as she jerked the hair from my face, roots and all.

"I told you!" She said, still laughing.

"And by the way, you need to work on that voice. If you stub a toe and yell out like that you will be uncovered for sure."

I place both hands over my mouth and repeated my curse, but this time in a very lady like voice and tone.

"Now sit up and take it like a girl!" she said.

She was now laughing so hard that she had to lean on the counter top to stay upright. I couldn't help myself, I had to join her. This was really pretty funny.

Next she started on the makeup. This time we sat side by side and she would show me what to do then watch as I tried it. I had to redo several things a few times but eventually I learned the way to apply eye shadow, mascara, and blush. Turning the brush through my eyelashes was easy, but outlining my eyes with the eye pencil took a few tries before I could do it without pulling away. She taught me how to highlight my cheeks with the blush, spinning the fine brush over my face.

We worked with the lip liner and gloss a few times before I mastered that too.

She took out the drug store bag and handed it to me to open. Inside I found stick on nails, red polish and clear covering and a pair of clip on earrings.

Taking my hand she applied the nails to each fingertip. While she waited for the nails to dry in place she lift my feet to her panty clad lap and did my toes in the bright red polish.

Once the fake nails were set she began to shape them for me. I watched fascinated as she worked on my hands. Man hands quickly became a woman's fine hands.

Next she applied the same flame red to my fingertips. There is something especially feminine about nail polish, particularly red. I felt sure that she had picked the color intentionally to reinforce my image.

Fingers and toes done she lifted my hair and slipped the earrings on.

"I really wish you had pierced ears," she said as she did it, "I have some earrings that would be perfect for you."

"Right now I wish they were too," I replied in earnest.

We each applied some of her perfume and were ready to dress.

Of course my dick was sticking straight up by now and when I stood up she saw it and just shook her head.

"My God Jessie, can't you control that thing?"

I was pushing the front of my red panties out. She stood in front of me and took me in her hand and began to stroke me.

"This is what, three times today? I don't think you have ever been this turned on before."

I tired to play it off, "Cat you know how hot it makes me to see you running around in just panties! Damn you are the sexiest woman I know."

"Yeah, right! Have you looked in the mirror in the last few minutes buster? You are giving me a hell of a race for that title! Besides, I think you like this."

I didn't say a word, after all what could I say as I stood there in full makeup wearing her panties.

She stroked me until just before I came and then grabbed a wash cloth to catch the mess in.

"I'm not ruining my makeup this time!" she chided me. Funny, I understood and agreed with her.

She handed me a fresh pair of panty hose and when I had them pulled up tight she reached from behind under my butt and pulled my cock back as far as it would go. Then she cinched the hose up tighter. I slipped the same panties back on my legs and snuggled them in place around my hips.

"Oh go ahead!" she said reading my need. "Go put your shoes on."

I almost ran across the room to the bedside and picked up the white strap sandals. It only took me a moment to fasten them on my feet.

I strode across the room in my four-inch heels loving the feel of them on my feet, and on my entire body as I walked back to her.

I couldn't help stopping to admire myself in the mirror.

When I got back to her she had the second package on the counter. She removed something from it that I had never even imagined existed, a breast form. There on the counter top was a pair of tits, complete with nipples, erect nipples I might add.

"Wow!" I cried as I looked in wonder at them, "are those for me?"

"Well they sure as hell aren't for me lover! Oh, and don't ask what they cost."

She showed me how they had to be submerged in hot water first, then pressed to my chest to take the inside shape that would mold to my body. As we waited for them to warm up properly she took an alcohol swab and cleaned my chest.

Gently she removed them from the soak and lifted them to me. I could feel the heat as she pressed them hard against my chest using the cover that protected the outside of them. Once they had cooled she removed them and again cleaned my chest with the alcohol. She applied spirit gum to the inside mold of the breasts and pressed them back on me.

I was looking down as she held them in place and for the life of me it looked as if my wife were feeling up my gorgeous tits.

After several minutes she gingerly removed her hands and magically the breasts remained in place.

Cat applied a coat of foundation and then some lighter blush to my upper chest, to the rise of my breasts and then stepped back.

"Amazing!" she cooed as she looked at me, "go look!"

I turned to the mirror and found a well-shaped lady, with perfect c cup breasts and hard nipples looking back at me. As I stood staring in fascination Cat spoke from behind me.

"I wasn't too keen on the erect nipples, but that's all they had. I thought we could just cut them off a little,"

"What!" I yelled, "not my tits you don't!"

"Yeah, that's what I figured!" she giggled. "I think you will have fun with these, I know you will certainly draw some stares!"

Cat got a bra out for me saying that she wasn't sure of the "integrity" of the attachment and thought that I should wear a bra until we at least had a chance to test them better. The one she picked was a light lace red demi-cup that lifted the weight of them nicely and helped to shape them even more provocatively than they already were.

The red bra and panties looked great together.

Then she led me to the closet and we began the hunt for clothes to wear. I tried on several skirts, discovering that my waist was about two inches bigger than hers. We had to look for skirts with an elastic waist and finally settled for a cream colored button up that reached to mid calf. At first I wanted something shorter, but Cat reminded me that I had no experience in lady like modesty and might find the short skirt difficult to deal with. She also pointed out that the button up could be left unbuttoned for the last four places and give a very nice swing to it as I walked. It would also be comfortable to sit in. She hinted that there might be another advantage, but I was already enamoured with the fabric swishing around my legs.

For a blouse we choose a white slip over that was almost peasant cut, allowing me to bare a shoulder if I wanted to.

I walked from the closet and to the dresser where I picked out some jewelry. I chose one of her gold watches, a charm bracelet, the same anklet that I had worn earlier and a pair of necklaces.

I was done.

Cat stepped to her dresser again and removed a garter belt. As she held it up to straighten the straps my dick tried to rise again.

"Oh God, you're not going to wear that are you?" I asked in a husky voice.

"You're always trying to get me to wear it, to dress sexy, so I thought that tonight I would, just for you dear," she was smiling as I have never seen her before.

Cat's a normally happy person and her face radiates when she is in a good mood, but this was way more than I had experienced with her before. She was too happy for my good I thought.

She slipped the garter in place and rolled stockings over her beautiful legs as I stood and stared at my sexy wife. I was beginning to ache already with the want of her and knew that it was going to be a hard night.

She slipped the black panties over the stockings and then walked back into her closet. When she returned she had on a short black skirt and a silk black blouse. The skirt was about two inches above her knees and full cut to swing as she walked. The blouse hung loosely about her, moving with every motion of her body and clinging to all the right places. It was obvious to me that she wasn't wearing a bra as the fabric slipped across her hard nipples.

"You look just plain fucking sexy!" I groaned at her as the impact of her outfit took me.

"Why thank you, you ain't half bad yourself girl!'

I guess that really hit me. We were going out as two girls, not a guy and his sexy wife, but a girl and her sexy girlfriend. I had a moment of shock as I took that in, but before I could really get too scared she was there and had me in her arms, covering my mouth with hers. She held me for a few seconds, then whispered in my ear, "Take a look in the mirror honey."

I turned my eyes to be able to see in the glass and there was the most incredible sight of two girls locked in an embrace as obvious lovers. I think every man has a weakness for seeing women together and here in the mirror was one of my fantasies, my wife with another woman.

I cupped her breasts through her silken blouse and heard her moan into my mouth.

She returned the favor, but of course I couldn't feel anything, still the sight of her hand on my breasts was thrilling.

She slipped into a pair of black pumps and took my hand leading me out to our adventure.

She held the car door for me and as I started into the seat said, "See if you can get in without flashing me."

I tried, working first my butt and then my legs into the car. She smiled and cooed, "Oh what pretty red panties you have my dear."

She had picked a nice Italian place to eat and on the drive there we chatted as I played with my skirt, practicing how to get the material to fall over my knees leaving my thighs slightly exposed.

I found myself looking at my chest. My God I had tits! I couldn't believe it and several times I found my hand going involuntarily to my chest to test the weight and size of them. I experimented with the blouse, leaving first one shoulder bare, then the other, then neither, trying to move enough material of show some cleavage. Holding my blouse away from me I could look down and see the rise of my breasts into the bra and the deep valley between them. Letting the blouse lay on me I could see the two points made by my hard nipples.

I was mesmerized by myself.

We turned into the restaurant parking lot and Cat told me that it would be valet parking so to be ready to exit like a lady. As we parked two young men in red coats held our doors open for us. I sat for a moment and watched as Cat first turned her hips then lifted her feet out of the car. I duplicated her movement and as I started to stand I could see his eyes fall to my legs, then move up until they locked on my hard nipples. He held out a hand for me. Instinctively I took it and let him assist me from the car. His eyes didn't leave my breasts until I was fully standing in front of him.

Here I was standing all of 5' 10" in my four-inch heels holding the hand of the valet as he ogled my breasts. I stood paralyzed under his attention. Cat took my arm and led me into the restaurant. I heard the stereo tapping of heels as we walked through the door arm in arm.

We were quickly shown to a corner table where we were seated. Cat declined the facing seat and took the one on the side of the table next to me. I smoothed my skirt as I sat then parted the front opening allowing it to fall either side of my legs. I scooted around a got comfortable in my chair. Cat reached over and covered my hand with her.

"Nervous?" she asked.

"Of course I am," I replied with a grin, "but I have got to admit I haven ever been so excited, or horny."

Cat was beaming, her whole face alight with the happiness and excitement of this. I knew that she had been having fun with all of this, partly from putting me in my place, partly from winning the bet, but there was much more going on here.

The waiter came, introduced himself and left us fresh water. Nervously I took a sip. For the first time in my life I left lipstick marks on a glass. I sat staring at it. Cat patted my hand and smiled at me.

"Looks kind of sexy doesn't it?" she asked in a soft voice.

"Yeah, or at least I used to always thinks so when you did that, it sort of turned me on because it was just so feminine. Seeing it on my own glass is really mind blowing."

I looked at her suddenly feeling very vulnerable and frightened. In a choking voice I asked, "Cat do I really look alright?"

She raised her hand and cupped the side of my face lovingly, "Honey you look great, fantastic! Just try to relax and enjoy your experience."

I smiled at her and we took up our menus.

A couple of glasses of wine followed by a great pasta dinner helped to relax me and put my mind at ease as everything went along just fine.

Cat and I talked. We talked as I had never experienced before. Cat led the conversation into topics of fashion, celebrities and female oriented politics. I was amazed that I could not only follow along but actually contribute to the discussion. I guess reading the paper every morning had helped, and I also must have paid more attention to female-sided topics than I thought over the years. We moved into her girlfriends and degenerated into gossip quickly. I was learning things about the private lives of our friends and neighbors that I would never had known otherwise.

All I knew about my friends was basically their favorite football team and golf handicap. Now I was getting inside information about finances, children, and even the sex lives of people I thought I knew. I had to wonder if they all knew as much about our life.

I quickly picked up on her habit of touching when she spoke. She would place a hand on my hand, or arm, or shoulder or even my leg as she leaned in to relate some bit of juicy information. I found that doing so in return increased the sense of intimacy and involvement in the conversation.

Soon I was telling my own stories of women, and even some of the men I met through my job. I was surprised at how much I really did hear from them and was seeing that for some reason most of them felt at ease talking to me. Cat listened with attention to every word I had to say, and I found that I was doing the same.

No one paid any undue attention to us, at least that I had noticed. That is until Cat leaned over to me and spoke.

"Honey, don't panic and please don't look, but there is a man over there trying to peek up your skirt."

My face must have been a riot of expression as Cat broke into a fit of giggles. I jerked my legs together and reached to tug down my skirt.

"Slow down Honey," she said, " there is nothing to get upset about. He is just trying to check out your panties."

I don't know why that confused me so much, but it did and I just stared at Cat. She was getting a big kick out of my dilemma.

"He's been looking at us, you mostly, for about a half hour, I wanted you to be more relaxed before I made you aware of it. This is just one of the things you put up with when you chose to wear a skirt."

I was shocked, "You mean this happens all the time?"

"Oh don't go getting self righteous on me, how many times have you been on the other end of this buster?"

I just grinned, "Who me?"

"Yeah, you. I always knew when you were checking out some legs or doing a little panty peeking, I just let you think I didn't know."

Now I was even more confused, "Why?'

"It didn't hurt anyone and it always got you in the right mood for me, so what's the harm. Besides, you obviously enjoyed it."

"Ok, ok, so now what the hell do I do?"

"Well you have several choices in this situation. If your skirt is long enough, and yours is, you can just tug it down or rearrange it a little to cover your knees, or you could simply turn your knees away from him so he can't see anything. Of course in a restaurant like this you could place your napkin on your lap and let it cover your knees. The thing is to do it so that he doesn't know that you know he is looking. Once it becomes common knowledge it can get embarrassing for both of you."

She continued, "That's assuming that you really want him to stop looking."

I still hadn't moved, hadn't done anything but stare at her since she began this lesson in "skirt etiquette".

"What do you mean, if I want to?"

"Oh, I don't know," she said with a sly smile, "maybe you are in a really good mood, feeling kind of sexy or daring and want to tease him a little. Or maybe you are just a pervert and want him to look up your skirt."

I was stunned, "Damn Cat, you mean you guys really do that, let men look up your skirt and see your panties?"

Her smile turned to a lopsided grin that said, "Duh, earth to Jessie!"

"Look Jessie, just between us girls, ok? If you tell my husband I will fill your douche with pepper juice, I swear! But yes, sometimes I feel sort of playful and sexy, especially if I am out with him, and I will tease a little. I mean who does it hurt, right? It makes me feel, oh I don't know, special, sexy, attractive, and a little naughty."

I still hadn't moved other than to turn my head and catch a look at the man she was talking about. He was not bad looking, maybe in his late 40's or early 50's and sitting across from a well-dressed lady who was obviously his wife. With each forkful of his desert he would move his eyes to my legs. I really didn't know how to feel about that.

Cat saw my discomfort and continued, "Now when you wear stockings and garters, like I am tonight, it's as if you hooked a rubber band to them. Every time they turn away from you their neck just springs back around. It is really funny to watch."

I was just staring at her, dumbfounded.

She went on, "If I'm feeling really naughty I will let my skirt ride up and show the lace at the top of my stocking and maybe a garter strap or some bare skin."

I think she knew all too well what her confidence was doing to me. I could feel the head of my dick struggling under me, trying to get free in vain.

Report Story

bystillconfused© 29 comments/ 333347 views/ 55 favorites

Share the love

Report a Bug

4 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: