A Change For The Better

by Steffani St. James

Part I

 

I'm a cross-dresser! What's that you ask? It's a male who prefers to wear the clothing usually reserved for females. Since I was very young, feminine attire has attracted me. In fact, everything associated with being feminine or female has attracted me. I love dresses and gowns, skirts, pretty blouses, high heel shoes, pretty under-things and sheer nylon hosiery. Being able to wear one's hair long and have it styled and get a permanent at a salon is another thing that as a male, I couldn't do. But in my feminine world, I could go to a salon, get a cute hairstyle and even have my nails done. Just the thought of being able to stroll out of such a place, leaving a sexy scent behind me, all the while giving no clue to anyone watching that I wasn't a real female has always been a fantasy of mine.

Until three years ago, I'd kept that side of me buried. Then, due to other circumstances, I finally admitted my hidden life to my spouse. To say the least, she wasn't pleased. How could she be. This wasn't something wives can easily understand or even accept. Mine tried to understand and grudgingly accepted to a degree. She said she never wanted to see me dressed. I showed her some photos of myself and she did say I looked very nice; not ostentatious or teasing in a negative manner, but acceptably attired. However, there would be no 'husband as a girlfriend' scenario. My outings or getaways would be solo affairs.

After I'd retired and we located, out of nowhere, she brought up the subject of my dressing one evening. First, she wanted to know if I still got the urge to dress and get made over. I responded that I did and always would want time to express my feminine side, even in retirement and even though I was approaching my "elder" years.

Then she told me since that was still the case, she wanted me to look proper when I did transform and to that end, I would have to lose weight. I didn't make a very attractive woman weighing 225 pounds! I agreed and she started me on a diet and exercise program. Oh yes, there was to be no dressing until I reached a certain weight that she had determined using my BMI. I knew that losing that much would be a trial but the lure to be able to continue dressing was such that I readily agreed. Maybe it was her way of coming to grips with having a cross-dressing husband and using that to some personal advantage. She also had me start taking 'natural' vitamins every day. Each morning I swallowed a large purple pill with my orange juice.

Once each week, she weighed me in on our electronic bathroom scale. Luckily for me, there was always progress. The first month I lost ten pounds. Each month thereafter, I dropped another eight to ten pounds and after the first six months, my weight hit 172 pounds, stripped. My wife praised me for my dedication but the exercise and strict diet continued. I thought that my BMI goal was about 172 pounds for my age and height and I was so close to that.

She countered with her position that a guy who cross-dresses needs to have a weight and shape that more closely mimics a genetic female's. So, the weigh-ins and diet and strenuous exercises continued. And, she began having me see a professional who used electrolysis all over my body. Soon, my face, neck, chest and legs AND bikini line were as smooth as a newborn baby's.

Three months later, I was greeted with hugs after a Friday morning weigh-in.

"Honey, guess what? You've hit my target finally. You weigh 145 pounds; that's about right for a gal who's six feet tall. Now, let's take a closer look at you. Are there any other things you feel we need to do before getting you all dolled up?'

I struggled to bring up this next issue. I'd been noticing a tenderness and enlargement in my chest which seemed centered on my breasts. Guys have breasts but they sort of become part of one's "pecs". Mine had blossomed and were showing definite nipple and areola development. In short, I looked like a pubescent teen! I began sobbing as I showed her my chest.

"Now, now, don't cry. You're just developing like any 'girl' would. Don't you like your new breasts? You look so sweet with them. Think about this. You used to be overweight and totally out of proportion. Now, with a slimmer you, your figure is beginning to look appropriate for an attractive woman. Leave everything to me. From now on, I'll help you be the kind of girl I know you can be!"

Now THAT was certainly a change in her attitude! She was going to help me?

She reached over to the top of the dresser and brought out two items. The first was a very scanty, shimmering white satin thong panty. She had me step into the tiny panty and then she pulled it firmly up into my crotch. She grabbed my testes and pushed them up into a hidden cavity I never knew I had! Then, she pulled my penis back between my legs – it was completely flaccid – and smoothed the narrow crotch of my thong over my now flat front. Next, she took a sexy foundation – a gorgeous white satin steel-boned lace-up corset. Turning me away from the mirror, she wrapped the garment around my waist. Then, she began tightening the laces, bit by bit, making my middle even more slender and 'wasp-like' than ever before. The garment had little lace cups and these cradled my burgeoning breasts and lifted, separated and thrust them forward and up making them appear even fuller and more like a genetic female's bust. Lastly, she made me sit while she rolled sheer white back-seamed stockings on each of my legs, attaching them to the six dangling garter straps from the corset.

"Now, Jennifer is it? Please stand so I can get a better look at you. Mmm, you do look very nice now, easily able to pass as the woman you'd like to be. I've come to change my own mind about your dressing. From now on, I want you to be dressed as Jennifer all the time. Don't cry, sweetie, I know you need this. In fact, we're going to do oodles of things now that you can be out and about with no one "outing" you. Let's get you dressed for your first trip out as Jennifer."

She helped me don a cute petti-slip and camisole, high heel pumps that complimented the navy blue mini-skirt and fitted jacket she had chosen for me to wear. After clipping adorable large button-type earrings in place, she added a necklace, bracelets and a watch to my bejeweled self and watched as I filled a purse with the items a gal should carry. She took the time to carefully polish my longer nails and pinned a pretty curly blonde wig in place on my head – she used a tightly-fitting wig cap to anchor the hairpiece. Now it was time for my big test. Would I leave the house? Would I pass? Would that bother me? Or would it bother her? And what would happen next?

We walked outside and my wife opted to drive since I "hadn't had much practice driving in heels yet". Our first destination was a mall in a nearby town. I was to buy a wardrobe of pretty lingerie and foundations. My wife assured me that she would help. I discovered that her help was confined to the most risqué, wild fashions. I had to personally be fitted for most of the bras, panties, girdles, shapers and slips I wanted and needed. Then we hit a department store where I acquired several skirt suits, sexy tight jeans and loose-fitting trousers, blouses and some classic dresses; mostly sheaths, A-lines and shirtwaists. At a formal-wear boutique, we purchased two lovely gowns; one was a full-skirted ball goen and the other was a clingy sheath. My wife also insisted I be measured for a luscious satin bridal gown with crinoline, veil and gloves included! Next was a stop at a store that sold leather goods; add several purses and wallets to my collection. The trip wouldn't be complete without a stop at a milliner's for some picture hats and several wigs. "Jennifer" was to be the best "coiffed" lady in the neighborhood! Finally, we hit a specialty shop where I got some swimwear (bikinis and maillots), a special device designed to simulate a woman's vagina and some more exotic jewelry.

By late that day, "Jennifer" had a rather large wardrobe and 'her' wife was a proud 'sister' of a new girl. Back home, we put everything away in the spare bedroom that was my den, then set about putting together some supper. It was like two giggling girls that we prepared a light meal and cleaned up afterward. One obvious thing, my wife was pleasantly pleased at how nicely I got along with her, now that I was a woman.

We took turns using the bathroom and getting ready for bed. I showered, removed my makeup and applied night-cream and dressed in a cute baby doll, panty and jacket. I slipped into furry pink scuffs and sashayed into the living room where my wife was waiting.

I sat next to her and immediately she began cuddling and kissing me. I thought that she did not want our situation to become one where we would be 'lesbian' lovers, but it certainly seemed headed that way. She worked her hands under my nightie and began teasing and tweaking my nipples. I sighed as she suckled them and slipped her hands between my legs. I wanted to pull away but she held on, working herself and me into a frenzy. She had my face pressed into her scented crotch when she shuddered to an immense orgasm. Mine followed hers by about 30 seconds.

"Wow, you ARE a female now", she exclaimed. Your orgasms are just like mine! You pleased me so well, I wonder if you could please a guy? We'll have to find the answer to that, won't we?"

I merely nodded, shuddering a bit over her willingness to allow me to go much further as a woman than I'd ever planned. She wanted me to accurately look the part. She wanted me to be able to be naked but still appear to be female. And now, she alluded that I'd be involved with a guy. Where was all this to lead?

  

  

  

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