Not Willing to Go Back Ch. 02

How Winning A Contest Transformed our Lives

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A multi-part story of how a husband transformed his life, initially to win a big prize, but more and more to explore who he really was. Post-Surgery, a new life begins for Jay / Jane.

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Recovery and Getting Comfortable

I recovered pretty well over the next two weeks, with most of the first week taking it very easy, with a decent number of painkillers the first couple of days. I told my boss that I had come down with a severe case of the flu, and used a week of sick leave. It was all kind of hazy, but I knew I really didn't like the feeling too much.

It turned out that after a week, I was actually itching to be back at work. The second week I could move around, but had to keep the medical bra on, so really didn't understand what I would look like after the surgery. This was actually the longest period of not working out I could ever remember.

Still, the bandages were waterproof, so I could function. I could shower, wearing the waterproof bandages, and shave, as well as work on my fashion, makeup and walking tasks Jill had assigned me. She told me I had to be comfortable in up to six-inch heels for the big party, and it would take a while.

We also knew that the implants and expanding fat cells would alter my center of gravity and balance. Even with the bandage covering my chest, I was much different in appearance. I was no longer Jay that short, slender runner. I really did look like Jane, a very fit, but all girl, runner.

And Jill was right, I had to walk like every other woman, not a man faking it for the party. I watched videos and all sorts of shows on TV, as well as working at it every day. I worked past the sore legs and feet, and was more than a bit turned on seeing my legs in a pair of ever higher sexy spike heels.

But actually, I was very proud that I was strutting around like a Vegas showgirl in the heels by the end of the second week. I had quickly learned to compensate for my altered center of gravity, and was able to build in a very sexy sway to my hips. I don't think Jill expected it to be that fast.

We even danced together once or twice. Jill noted that walking was fine, but I had to dance like a real girl too. She promised me we would branch out to try some platform heels as well as some very sexy boots. I wasn't missing my boring, but comfortable male shoes at all anymore.

However, in all honesty, beyond work, what else did I have to fill my time. I had to let my stiches heal, so no running or any other exercising, I felt self-conscious with the bandages so wouldn't go out. Instead I worked and every hour took a break to walk for five to ten minutes around our condo, practicing all sorts of different walks on each floor and up and down the stairs.

I wore whatever heels I was wearing that day, generally pretty high. The ranged from four to six and once even some seven inch heels Jill had in the back of her closet. In a cliché, I was a natural, it seemed. And walking in heels still got me hard every time too! I loved how I had to push my chest out and how long and tall those towering shoes made me look. And of course, by now, my hips swayed naturally.

The two week appointment was actually anti-climactic. The doctor was very happy with the healing. In just two weeks the expanding fat cells had already made me just about a C cup. The stiches were already dissolved under the bandages. I loved that there was nothing to painfully pull out. She had been very precise, there really was no visible scarring below my now healthy, smallish, C cup boobs.

After our follow-up two-week appointment, we decided to not go home right away. I wasn't nervous at this point, looking pretty hot in a simple T shirt and skinny jeans with some kitten heels. I had on my everyday light makeup, and my hair was in a long pony tail. As Jill convinced me to do dinner, I looked in a mirror and calmed down. We really did look like a pair of hot, very fit, twenty somethings.

We ate a light dinner out, at a small café, came home and cuddled over a glass of wine. I was still a little emotional with all the changes, so it was a quiet night. But Jill told me how much the waiters were all staring at us, especially as we went to the lady's loo. I had not even noticed; I was so focused on how my new breasts felt in a sexy lace bra instead of that ugly medical one.

My incisions had healed perfectly, but the injected fat would have to finish expanding over the rest of the first post-surgical month to my goal, a full C cup. My doctor reiterated how, although it was taking longer, I had made the best choice. She said my new boobs would feel much more natural this way.

The next day though I showered for the first-time bra-less. Wow, I nearly came from the feeling of the water on my breasts, I was rock hard in the shower. I couldn't resist, and when I stroked myself with one hand and rubbed my new boobs with the other, I came all over the wall of the shower.

I also couldn't stop myself and gathered a bunch of my cum on my fingers, and like Jill had done, when she pushed her fingers into my mouth. On my own, I sucked it my cum off my own fingers, swallowing it, in all its saltiness. It was different, pretty thick and salty.

But to me it was really not at all slimy like Jill always claimed. It was an odd viscous feeling in my mouth, but certainly went down my throat smoothly. Yet another odd sign, I was not the least repulsed by tasting and swallowing my own cum.

I dried off and moisturized, and played around in the bathroom in front of all the mirrors. I was amazed, as I looked at my body, post-surgery. I had real curves, and already I was so smooth below my neck. I was slender but not skinny, and realized my ass was probably too small and muscular.

With all my curves and long blond hair, I showed no trace of Jay at all, except of course for my cock. And it was rock hard from just the preening, sticking up at an angle and already dripping with pre-cum. I felt I looked pretty hot, but to some degree, a little bit if Jay remained. My skin didn't seem soft or smooth enough.

What Jill didn't know is I had been researching what hormones would do what to me. I was focused on how I could make sure no one could detect any maleness in me at all. The technology had really improved.

I found several mixes that wouldn't impact my male parts, but would greatly assist my feminization. I went back to her doctor buddy that week. Only after she swore to never tell Jill, I got a prescription for a cocktail of hormones. I was really focused on winning the contest, or was something more developing in all my efforts to be a perfect gurl

The hormone mix was one of those new mixes, designed to help my skin softness and curves, but not affect my ability to get an erection and perform as a male. Taking a daily dose was now part of my morning routine, and maybe it was hopefulness on my part, but it seemed that my skin was smoother and my pores smaller almost right away.

Though I was a little more emotional, it wasn't like I was all weepy. What was ideal from several points of view was that the hormones didn't stop me from functioning as a man at all, so Jill never had a clue. And the hormones did make a difference, I could almost feel my pores getting smaller and my skin softer and smoother.

I spent the rest of that day, my first real day as Jill, getting a little carried away. I wanted to see how this body looked in different outfits. I went through Jill's dresser, imagining all the outfits on my new body. I spent the most time trying on Jill's lingerie and heels, and experimenting with makeup.

I quickly realized that my new boobs, growing out to a full C cup were going to require my own bras at least. Jill's smaller B cup bras were way too tight, even as the injected fat cells were still enlarging! But I did still fit in some of her looser outfits, and most of her lingerie looked great, I just overflowed the bras and corsets.

Late that day, I finally laid back on our covers, fully en femme, and gave into temptation. I had done a full sexy hairdo, with my blonde locks all curly and full. Already my hair was half way down my back and more of a mane than a delicate head of hair. To me it was one of the Jane's best parts.

The hair went very well with my makeup look. I had worked hard on a very heavy, dark, effect. It did make my eyes really standout and my cheekbones had real definition. My lips of course were a bright shiny red color. I was thankful, looking at the mirror that I had never had much of an Adam's apple.

Raiding Jill's lingerie collection, I had tried on several outfits, finally settling on a bright lace red and black set that really worked with my blonde hair. It was a look I already dubbed, 'ready for clubbing'. The full set that started with a low cut bra, barely covering my nipples. It had a lacy garter belt and I added some fishnet stockings that I felt looked divine with my five inch heels.

As I lay there, I began to stroke my hard-on and play with my balls, peeling off the panties of that cute red and black lingerie set so I had full access to my cock and balls. After a few minutes, I even sucked on one finger to get it wet and played with pushing it in an out of my own ass. Wow, that was different.

At that point, Jill, just back from work, appeared in the doorway, luckily not while I was finger fucking my own ass. I had not expected her for another hour or so, maybe she wanted to be home with Jane more than she wanted to be climbing the corporate ladder...that was a nice change too.

My hot wife was clearly a bit surprised. She, gasped, smiled and asked me if I was going solo or wanted some company. I laughed and told her I was waiting for her. Jill then pulled off her jacket and immediately stripped off her entire outfit, as she put it, to not miss any of the fun.

We made love, but did it almost lesbian style, with no penetration, all oral. She was voracious, sucking my head and then up and down the shaft and swallowing my balls one at a time. I was just as focused, sucking on each of her lips and really going to work on her very hard clit. Soon we both came, but I found out we weren't done.

While we were recovering, side by side in a 69 position, Jill spun around to kiss me, once again passing my cum back to me. Jill didn't know that I had tasted that flavor only a few hours before! What was she trying to teach me? I didn't know, but wasn't grossed out anymore at all by the texture or taste, and was actually starting to savor it.

Settling in to life as Jane

The rest of that first month I got into a routine. Like before my surgery, I got up as Jill was leaving, shaved very closely, took a hot shower and moisturized every inch of my skin. Some days I even lounged in a hot scented bath, with only my head out of the fragrant water. I was learning to enjoy taking care of my body, it made me feel sexy and very feminine.

This was easier as Jill had made sure I had no more plain soap and shampoo. We each shared a full suite of scented products, making my skin and hair look great while I had subtle floral aroma on my skin. Rubbing the various lotions into and body not only made me very horny, it made me skin look great.

Often, with my much enhanced body, I couldn't resist playing with my very sensitive nipples. I loved it when I combined breast play with my stroking of my hard dick. When I looked across the bath at the mirrored wall the sight was amazing. Here was a blonde with really big hair, looking like a girl in her "fun time" till you looked further and saw my other hand playing with my very hard, shaved shaft.

And now, every time I came, I made sure I savored the taste of my cum. It was very odd to me that I was actually swallowing cum almost every day. I even started to wonder, if all guys tasted the same and if I could get so flexible as to suck my own dick. But sad to say I couldn't spend all day in the bath playing with my body, I still had a job, just not one I did in sweats and a T-shirt anymore.

After enjoying my pampering routine, I then worked on a style for the day. I was quite deliberately attempting to expand all the ways I could look as a gurl. Starting with my makeup, I was trying to learn all the ways I could make myself appear. My skills increased rapidly, and I was amazed at all the ways I could make grungy Jay now appear as a much hotter and sexier Jane.

The looks ranged innocent young girl with barely a hint of lipstick and eye shadow, to stripper-slut. I soon realized I didn't do delicate or innocent very well. I seemed to be attracted to the sluttier, more ultra-feminine looks. My face had so many layers and colors on it, but I looked super-hot I thought.

I found out that I especially liked the feeling of long thick fake lashes on my eyelids. My lashes were now extra thick and long, and when I batted my lashes, I always got the attention I now seemed to crave. I also thought I looked super-hot with the thin arched brows I had adopted. But what made everything work were the heavy dark eyeliner and different eyeshadow colors.

And now my lips were never allowed to look "natural". They were always a bright color, usually red, often sealed with a shiny top coat. It was odd to see my lip prints on coffee cups and the marks I left on Jill's neck and breasts as we got frisky. But she told me it was very arousing to feel my lips on her body.

Then, unlike when I was a "conventional" man, I made sure I stayed dressed to the nines all day. From the hot, sexy lingerie, all the way to the dress or skirt, including heels, I worked my hacking job as if I was ready to go out to a club or dinner.

I was pretty sure no one would have expected a hot gurl was the one taking apart their corporate security systems. And if they had seen me, they wouldn't have connected me with Jay at all. I was now curvy and hot, down to my now one inch red nails. In looking at me they would never have guessed either that I had a full set of functioning male equipment under my tight miniskirt.

After the first week I no longer hid when the doorbell rang with deliveries. The UPS and FedEx guys seemed to enjoy getting my signature, and I was amazed that they were so blatantly trying to look down my blouse at my boobs, or watched my ass as I put down a package in the foyer. But it served as more validation that to the world I was Jill's college classmate and no one saw any part of Jay in my new body.

I also felt I was more convincing as Jill had gotten me those pieces of concealing underwear; she called them gaffs. I never said anything to Jill about my routine, but I think she thought I still spent the day working in sweats, only changing right before she got home.

What would she say if she knew I was fully in character dolled up every minute of the day? How did I tell her I really loved taking all the effort to be a sexy slut...that it seemed to be taking me over? All I knew is I was no longer nervous, and in fact felt more at home as Jane then I ever had as Jay.

Month Two: Starting to Feel at Home with the New Me

As my second month preparing for the contest began, my confidence was rising daily. I knew I was a very hot gurl, and could already wrap almost any guy around my finger without even trying. It wasn't just my body, or my deliberately sexy clothing, it was how I carried myself and even walked...or strutted.

But more interestingly, I didn't miss dressing as a guy or doing all those guy things. We still really enjoyed sex together, but I was Jane every other moment of the day. I found I truly enjoyed all the very feminine parts of Jane, the primping, the sexy clothes, the strutting around in super high, sexy shoes.

I had been proud of myself, not just ordering clothes from the internet, but hitting the mall to buy some bra and panty sets at Victoria's Secret, now that I had stabilized at a full, round C cup. Jill had said we could save money by sharing lingerie. But it wasn't just that my chest was bigger, I wanted to have my own cute things, that were just as sexy, but a little different than Jill's tastes.

I also picked up some cute outfits that were all mine at the mall. I loved how the bored guys, waiting while their girlfriend or wife was trying on clothes, couldn't keep their eyes off of me, or at least my ass or tits. But then again, I was rocking it in skin-tight short skirts and very low cut tops. Not to mention my big wild blonde hair seemed to transfix half the guys.

I had also been losing weight, hard as it was to believe. I followed Jill's doctor's plan and religiously took the hormone cocktail, while still running at least 30 miles a week. I was only 120 on my slender 5'6" frame. With the running and weight loss I was now very slender, but pretty curvy.

The nice part is I could now fit in any of Jill's skirts or pants, no matter how tight. However, with my bigger boobs, only some of her tops fit me without being obscene. So, I knew I was going to continue to hit the stores for a lot of dresses and tops. It somehow wasn't a problem for Jane to shop for a whole new wardrobe, Jay had hated shopping in any form.

Our doctor had recommended now weights at all, but a total focus on core strength and flexibility. She told us I needed to not bulk up, but become more sinuous. So, I had been doing yoga and core exercises to increase my flexibility. As a result, I rapidly improved my strength, and had a very toned physique.

I had really increased my flexibility, with the daily hour of yoga. I also loved looking over at my curvy body wearing some of my new skin-tight spandex yoga outfits. It was only when you saw the bulge between my legs that I didn't look totally female.

I had, of course, another goal in all this yoga. And though I could only just kiss the end of my dick when my legs were thrown over my head, I was getting more of cock in my mouth each week. My goal remained to be able to deep throat my own dick of course. I also figured being ultra-flexible would make my partners happy too.

Every day as I posed and admired myself after my shower or bath, I was starting realize, I truly was a hot chick now. Jay seemed more and more like a distant memory. At night Jill and I would often vamp in front of our big bedroom mirror.

We were each wearing some hot outfit, always with sky high heels. I got hard each time I was kissing her, especially seeing our heavily made up faces locked in a sexy kiss. But what appeared in the mirror was two slender, fit, hot women, not a girl and a guy in drag!

The nicest part was that my arousal wasn't wasted. Jill would feel my hardening dick and it just seemed to arouse her more. She often would push up my skirt, and drop to her knees. She now seemed to revel in swallowing me whole, while running her hands up and down my garters and stockings.

I wasn't allowed to cum, instead Jill would strip, often leaving on her lingerie, to pull me down to her soaking wet pussy. I loved how, without fail, I could bring her to a moaning intense climax, especially if I sucked her clit as I finger fucked my hot wife with two or even three fingers.

By then I was more than ready to cum. Jill didn't disappoint either. She seemed to prefer being on top, but no matter what the position we loved to fuck while playing with each other's tits. All I knew was that when Jill stroked and pinched my new tits I was going to cum explosively. I loved that of course.

I had more changes than just a nice rack. I was now sporting a huge head of curly blonde hair. It complemented my body and my clothing, turning me into a very hot package. Of course, always strutting around in sky high heels and favoring tight, revealing outfits didn't hurt either.