tagTranssexuals & CrossdressersTransformation Ch. 01

Transformation Ch. 01


If you are looking for a tale of thought provoking sexuality this may be for you. If you want mindless and indiscrininate sex maybe you should read something else.

The characters are fictional, the locations are fictional, and the events are fictional, all that is real is the most important part, the emotion of the fantasy.


Hello my name is Jessup and I wear panties. I know, that sounds like the introduction to a Crossdresser's Anonymous meeting.

Before I get into the heart of this story I need to fill in a little background for you.

I meet my wife, Catherine, in our first year at college. We were both new freshman members of the swim team. I was there on a swim scholarship, she was there on her Daddies money. She was a great swimmer and a great student, but her family declined the offered scholarships saying that they should go to more financially challenged students. For the first year we were just teammates, and sort of friends. The second year our friendship grew and we even started to date a little. Most of the time this was school events and with common friends along. We clicked. We found that we shared a lot of common interests and values. In our third year we became lovers and finally as seniors we shared an off-campus apartment. Right after graduation we married and have been very happy for the five years since.

One of the things we shared was the ability to talk. We found that we could speak openly and honestly about anything and not be afraid of the others reaction. That has been one of the best parts of our relationship. Even in sex we could be open and free. She had no false coyness or inhibitions about the topic or the act.

As I said I was at college on scholarship and had to keep my place on the team to stay in school, so I was very competitive and willing to do anything it took to keep an edge on the other swimmers. She swam for the right reason, she loved it, but she also loved to win and would swim her heart out at every event. When you are swimming at that level one of the things you do is shave any body hair off. Even one hundredth of a second can make a difference in a meet. At first I was very self-conscious about body shaving, but soon realized that no one noticed. I had always had light and fair hair, head and body, so I guess it just didn't look much different to people who knew me, and strangers just didn't look that close. I got used to it. Cat and I started to help each other shave when we moved in together. Those sessions became more often than not, highly sexual and a lot of fun for both of us. There is something very personal about it that makes it very intimate and sexually charged. Of course one night I had to carry the shaving to another level and through the laughter of both of us shaved her pussy bald. In playful retaliation she shaved my pubes bare too. The sex following was awesome. Over the years since she has kept the bare pussy saying that she likes it and that she knows how much it excites me.

Cat's wardrobe almost doubled when we moved in together, I am only 2 inches taller than her 5'4" and about ten pounds heavier. She was constantly raiding my closet for sweatshirts, shorts, t-shirts and even some of my jeans would fit her, if a little loose.

I couldn't bring myself to borough her primarily pink and blue shorts and sweats.

Over the following years, to keep a little spice in our lives we had developed the habit of making bets. These were harmless, sometimes sexy and sometimes not, little wagers with each other. We would bet on a football game, and election outcome, or even once on the "breakup date" for a couple we knew.

The wagers would be for a weekend of back rubs and pampering, a particular outing we might each want, or often a weekend of oral sex. We each love oral, both giving and getting and when the bet was for head the loser got nothing for the entire weekend and the winner got all of the attention. Winning or losing didn't matter to me; I loved the weekends. This story began with one of those bets.

We each came from a different hometown and each town had professional football team. Whenever they played we were certain to place a weekend bet on them. This was serious rivalry to us.

My team was the odds on favorite to win and had been doing great all year with only one loss early in the season. Cat's team sucked! She still felt a loyalty to support them and was ready to put herself, literally, on the line for them. We began to discuss the terms of the bet.

I have this thing for high heels. It is almost a fetish, or maybe it is. I love women in heels, I think they are the sexiest thing they can wear. Whenever I am out I can not help but follow the steps of a lady in heels. Heels do something for a woman, they walk differently, their butts look better, their legs shapelier, and their posture is much better. Cat has caught me at it and teases me about my little fetish. Cat wears them often, but not nearly as often as I would like, which is all the time.

"Ok, here's the bet," I told her, "If I win you wear high heels all weekend."

"Yeah, great, so what do I get when I win?"

"You name it lover, I have no doubt about this one!"

Cat just glared at me. She was pretty certain that her team was going to lose big time, but didn't want to back down.

"Look you are always trying to get me to wear heels. You even have me wearing them around the house when I clean or in bed when we fuck. Do you have any idea how much trouble that is? Do you know how much my feet can hurt after a night out in heels?'

I smiled at her and admitted that I was sure she got a little uncomfortable in them sometimes, but look at he great sex she always got when she catered to my little peccadillo.

"Come on Cat," I teased her, "what do you want to bet? I doesn't matter very much because I have a sure thing here so make it whatever you want."

She just smiled at me. I should have run then if I had known what was good for me.

"OK, asshole," she retorted," if you win I wear heels all weekend. But if, no, when, I win YOU have to wear high heels all weekend! You'll get to see what it's like to walk around on your toes."

I laughed at her. "Don't be silly, your shoes won't even fit me!"

"You will just have to buy some when you lose. What's the matter, scared?"

"Hell no I'm not scared, you don't have a chance in hell of winning this one dear! Ok, Yeah, if you win I wear heels."

"All weekend is the deal, remember?"

"Yeah, all weekend, but I get to pick the ones that you have to wear, and we are going out to dinner with you in a skirt and the highest heels you own!"

She was giggling, "Oh I can just picture you in you slacks and new heels at the restaurant."

I felt a little odd with the bet, but still highly confident that I had nothing to worry about when the ball was kicked off.

Needless to say I wouldn't be writing this if my team had won!

The game went into over time and Cat was bouncing up and down on the sofa as her team pushed the ball down field. They scored and unbelievably, I lost.

She didn't say a word, just leaned over and kissed me and then headed up for bed. It was a Thursday night game that had run late so we both needed to get some sleep for work the next day.

I was certain that Cat wouldn't push the payoff on the bet. She was a good sport and would never do anything to embarrass me. All day I made calls for our small company while Cat did her magic in the home office. It was almost five when I pulled back into the drive and wandered into the house all smiles after a good day. I had completely put the lost wager from my mind.

She was there waiting for me with a cold drink and a wonderful smile. Oh I am so lucky to have such a woman love me.

"We are going to eat at La Perette," she began. It's usual for us to eat out on Friday nights, well actually most nights. Neither of us likes to cook much.

"I'll go change and be right with you," I replied.

"Wait a second," she smiled evilly at me. "Put these on when you change."

She handed me a pair of thigh high hose. I looked at her dumbfounded.

"What in the world are these for?"

"You can't try on shoes bare footed and your white socks will never do for a pair of nice heels so you need to have these on."

"What the hell! I ain't wearing stockings!"

"You're not going to welsh on our bet are you?" she asked calmly.

I sputtered out, "You're not really going to make me pay up are you. You're not going to expect me to really wear high heels?"

"Oh yeah I am! And if you welsh on this you will never collect on another weekend bet, you can be sure of that!"

"OK! Look I will wear the heels, but only in the house, you can buy a pair tomorrow that will fit me."

"That's not the bet!" she cried, "the deal is all weekend and that starts now."

"Well I'm not wearing them out of the house, period! People will think I'm a queer!"

"So it's ok for you to collect on your bets, dress me up in some skimpy top or t-shirt so everyone can see my tits and think I'm some sort of slut, but you can't take it when you lose!"

This was getting out of hand, I had to put my foot down.

"Cat, I will give you whatever else you want, just not this, ok. I wasn't serious about the bet, you weren't suppose to win!"

"Oh, yeah, that's right! But if I had lost I bet you would have me standing on my toes in the highest heels you could find! I bet you would do your best to get me in a little skirt and prance me around not caring one wit if anyone thought I was a tramp!'

She broke out her weapon of male destruction; she started to cry. I just stormed out of the room.

The first thing I saw when I entered our bedroom was our wedding picture. I just stopped in my tracks. I had been so lucky to find Cat, we were almost perfect together in every way. Looking at the picture I realized what a jerk I was being. For all the things she did and gave to me I could stand a little embarrassment. I headed back down stairs.

I just looked at her, and she met my gaze unflinching. Finally I took the stockings and made my way upstairs.

I was mad as hell but knew there was little I could do now. If I refused it would undermine the basis of our relationship, trust. I took a quick shower, and after drying off sat on the bed and pulled the stockings up my legs. They felt weird on me and looking in the mirror I thought they looked weird too. I pulled my slacks over them, slipped on loafers and a pull over and went back down to Cat.

"There," she said, "no one can see a thing, let's go"

"Well I can sure tell, and I feel like a fag in them!"

"Shut up loser," she teased. "Let's get out of here before the store closes."

She took my hand and we went to the car. She directed me to a discount shoe store. Fortunately for me it was a stand alone place that because of the low prices didn't have attendants to help you try things on. Walking into that store, knowing that I was the one buying the shoes scared me to death.

Cat held my hand as she walked me down the rows of shoes. She stopped at a chair and told me to sit, then picked up the shoe sizing gizmo and told me to take off my loafers. There were a few other people in the store, but none close to us.

"Size eight, not bad," she said, "we should be able to find some pretty things in your size!"

I knew that she wore a 6 ½ and as I have said I am not much bigger than she. Somehow I was pleased that my foot was an acceptable size.

Again she took my hand and began walking me through the size eight aisle. She would stop and pick up one, then another for my inspection. There were a lot of sexy shoes there, many I would like to see her in, but somehow I just didn't see one that I could picture myself wearing.

She insisted that I try two different pair on and made a show of kneeling in front of me and fitting them to my feet. By now there was one woman and her daughter that were openly looking at me.

I was so embarrassed that I couldn't even think straight. I just let her lead me about and show me shoe after shoe, no longer even trying to hide what we were up to.

I spotted a pair of closed toe shoes that I thought might work. These had a round leather black toe that would cover my foot to about midway. There was a closed back and a box heel that shouldn't be too noticeable under my pants. I examined them and then handed them to Cat. She just smiled.

As I tried them on she cooed about how nice they looked on me and what sexy feet I had. I knew a payback when I saw one and tried my best to just get into the humor of it all. I was beyond being embarrassed now, into acceptance of my plight, so I stood up bravely and walked in them.

I had always heard how difficult it is to walk in heels, but I found it easy from the start. Having my weight shifted forward on my toes by the three-inch heels was different, but not disconcerting. I paraded around for her as she held her hand over her mouth and giggled.

"You're a natural in those honey!" she squeaked through her laughter.

Yeah, a natural what I wanted to ask.

When I went to remove them she stopped me.

"Oh no! All weekend, remember? You start right now wearing them, and that includes out of the store!"

My face must have been a sight to see because she broke into another fit of laughing as she took my hand and led me to the register.

"He's going to wear them out" she said as she handed the box containing my loafers to the clerk.

Of course it had to be a guy and his look was one I hope to never see again, pure disgust.

I paid and we left. As soon as we cleared the carpeted area of the store I could hear the click of my heels on the hard surface. That was one of the triggers that I loved about Cat in heels. Every time she wore them I would listen for that tell tale click of her approach. More often than not I got hard when I first heard, and then saw her walk to me in sexy heels.

Now I was hearing myself. I hoped that my pants were long enough to cover the shoes and that all anyone could see would be the toe of the shoe. That didn't look too unlike any mans shoe, unless you got a peek at the rest of it.

At the car she insisted on driving.

"It takes practice to drive in heels, it's like an art form. I'd sure hate to see you try to explain your erratic driving to a cop in those shoes."

I let her drive. She headed right for the restaurant. How in the world was I going to face this? I looked down at my new footwear and sighed. "You know" I thought, "they do look nice, almost sexy, shame she isn't the one wearing them tonight."

I decided that the only thing to do was brazen it out and walk in as if a man in high heels was nothing unusual. As we neared the front door Cat moved behind me and whistled,

"You do have a cute ass in those shoes, it really tightens your buns up!"

God, how many times had I said something almost identical to her? I her case I was right, she did have a cute ass, but me?

This was not a fancy place, in fact it was counter service and scattered tables around the room and on the sidewalk. We proceeded down the counter and got our trays of food then I followed Cat to an outside table. I picked the seat by the wall, hoping that it would limit the view of me to passers-by. We ate in silence for a few minutes.

"You really are a pervert, aren't you?" I heard her say over the table.

"What the hell do you mean, this was your idea!" I retorted sharply.

"Oh I know that, but I'm not the one sitting there getting off on the sight of my own feet in sexy shoes."

"What," I started to say, then realized what I had been doing. I had been watching my own feet as I wiggled a heel around. I blushed deeply and just smiled at her.

"Well they are sort of sexy aren't they?"

"Yeah, they are, and so are you, even if you are a pervert!" she snickered.

"I am not a pervert, I just have a thing about heels, I think they are sexy!"

"Oh yes, I can see that, even when you are the one wearing them," she continued to laugh.

I was starting to get mad and she quickly saw that in my face. She reached over with her hand and covered mine and looked into my eyes.

"Relax, I'm just teasing you. I think you are being a very good sport about all of this and right now I am so horny I think we should hurry up and eat and go home and fuck our brains out!"

I thought that was a great idea myself and quickly we finished our food and I again paraded out of the place and across the lot to the sound of my own steps.

She was insatiable. We screwed in every way we could for hours that night and finally fell into sleep in each other's arms.

The next morning I was up early as is my habit. As I rolled out of bed she leaned over to me and pulled me back for a hug and kiss.

"Don't forget you shoes,' she said in my ear.

I had forgotten, but her words brought it all back to mind.

I pulled on my swimsuit and slipped the shoes on my feet then left the room.

Behind me she called out, "You really do have a cute ass!"

This was my first trip down stairs in high heels and it was considerably more precarious than the trip up last night. I realized why women use the handrail.

Outside at our pool I kicked off the shoes and jumped in for several laps. As I swam my mind went back to last night and the silly bet that I had lost. I had been terribly embarrassed a lot of the time, but also turned on by the sexy shoes on my own feet. I felt that the lift of the heels had made my legs tight, my ass tuck in and my walk sultry. What kind of thing was that for a guy to be thinking about!

I swam harder.

Finally I was winded and had to get out of the water. Once again sitting by the side of the pool I asked myself if I really needed to put the shoes back on. After all Cat was still in bed and I could always just slipped them on when she came down. No, a bet is a bet and I needed to wear them even if she wasn't watching me. I slipped out of my wet suit and into my heels then wrapped in my robe.

My morning routine is to swim then get the paper from the front walk and sit reading it while I have my morning coffee. You don't even think of habits like this until something interferes with them. I already had the heels on when the thought occurred to me that I still hadn't gotten the paper.

I walked to the front door and peered through the sidelight looking for any neighbors about. No one was in sight. Quickly I opened the door and made for the paper. I wasn't exactly running, but was scooting along as fast as I dared in the 3-inch lifts. No one was around as I grabbed the paper and made my way back to the door a little more calmly. Then I did an odd thing, I just stopped in the door and stood there looking around.

"What you doing, flashing the neighbors?" came Cat's happy voice from behind me.

"Uh, no, just getting the paper," I replied weakly.

I went back inside and poured us both coffee. We sat together and shared the morning quiet.

"Why don't you go get a pair of your cut offs on and then you can help me do some house work," Cat said after some time.

I grinned at her. Hearing the playfulness in her voice I knew she was up to no good, "What do you have in mind lover?"

"Oh I though a little lesson in what's good for the goose is good for the gander might be appropriate right about now."

"Oh?" I asked raising an eyebrow.

"Yeah, you always want me to wander around the house topless and in heels doing the house work, like what's her name, Melanie whatever, in that movie vacuuming topless. Well I think you should try a little of that yourself."

"Oh crap! Come on Cat, you can't really mean that?"

"Oh yes I do! You come on yourself, be a good sport about losing and go get those shorts."

A couple of minutes later I came back downstairs wearing a pair of cut off jeans. She motioned me to her and when I was in front of her she rolled the cut off legs over and over until they wouldn't go any higher. She had effectively made hot pants out of my cut offs.

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