Not Willing to Go Back Ch. 01

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.

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Identifying the Prize and How to Win It

This is my story over the last two years, recounting how what started as a complicated plan to win a contest changed my life, and for sure my wife's. It ended up with me not easily able and to be honest not willing to go back to my original condition and orientation. I found out that vague feelings and interests really signaled a much more complicated set of sexual desires lurking beneath the surface.

My wife Jill and I were really a matched pair. We had met at University, on the cross-country team, running had always been a big part of our lives. Standing next to each other, we really didn't look that different. We were both built for running long distances, short and slender, with narrow hips and a very low BMI. We each were about 5'5" and probably no more than a hundred and change in weight. Jill was more athletic than curvy. In today's slang she was more a spinner than a curvy woman. She had, to me, a sexy slender frame, with smallish but very sensitive breasts and muscular, very shapely legs. She liked to show off her hot body, but tended towards the classy and sexy instead of slutty. But for her it worked for sure.

I was maybe an inch taller and had always been a longer distance runner, starting to really hit my stride at ten K races or even half marathons. Generally ignoring the gym and weights and running five or six days a week, I was about as slender as Jill, but it didn't bother me that she was taller in heels, though it did take me aback when she joked my ass would look pretty good in her skinny jeans.

After graduation we formalized our long-term partnership and got married. Jill got into a development program for young managers in a high-tech firm and as a computer science major, I found work via a professor I had really liked with a firm of cyber consultants. We basically served as white hats, hackers hired by firms to test their security and then write up the steps to take to actually secure the firm.

I liked it in all of my work was from home, I never had to work in an office, sit all day in meetings, or wear a suit for customers. I was making great money working from our home office. Additionally, I had the ultimate portable job, as long as we had good internet connections, I was able to work, so we could move to wherever Jill's career took us. Life was good for about three years, till we each were about twenty-five. Hacking into customer's computer networks didn't even really seem like a job, in most cases it certainly wasn't hard to do. And with no kids and no really expensive vices we were already starting to be very comfortable financially, but that had occurred because we took no vacations and were slaves to our jobs fifty two weeks a year.

Jill went off to an April executive summit and retreat, pretty sweet for a junior manager; the nice part is she was only gone for three days. That was kind of a bummer, but Jill came back with a crazy bit of news. Her company was having a Halloween blowout in six months. That of course wasn't too crazy. But to encourage everyone, there was going to be a prize for the best costume or pair of costumes, but to win you not only had to be the best pair, the judges, from all across the company could not guess who you really were. The prize was $10,000, and a trip to NYC for a week with tickets to two Broadway shows.

Like I said, crazy, the total prize was probable worth over 15K. And for a couple who hadn't had a real vacation since graduation, that prize sounded extremely attractive, if impossible to achieve. But Jill was adamant, we were going to win it and she knew how. I was immediately a naysayer. Her boss and most of the leaders had met me several times and worked with her every day. How were we going to fool them? Unless we wore gorilla suits, and that was not going to win such a big prize, they would recognize both of us, and we wouldn't win.

As we relaxed with a glass of wine that night, Jill said she had the perfect plan, but I had to be willing to do everything she wanted and it would require total dedication. It would take six months of hard work, and really take me out of my comfort zone. Without really thinking about, especially that Jill had not share exactly what plan actually was, I agreed. Maybe it was the wine, and desire for that huge prize, but I grinned over at my bride and said

"Of course, lover, I trust you, we can do this, we just have to go all in. I will do anything you ask"

Jill gave me a big sexy kiss, after all she had been gone for three days and told me that tomorrow, Saturday, we would start the prep. We ate dinner, with the rest of the bottle of wine, and then adjourned to the bedroom to make up for three days apart. It was fun, we certainly were well matched between the sheets. People might look at us and think boring, but we really had fun in bed together, our sizes were a perfect match. On Saturday morning, over coffee, I finally asked her what was this big plan.

"Oh no one will expect this," she said.

We go as a pair of blonde bimbo party girls. I was shocked. First, we weren't two girls and second Jill had brunette, very professionally styled hair and was nothing like a club goer in any way shape or form. She saw my look and heard my first questions but had all the answers.

"So, hey Jay, first we are the same size, and just about the same build, so that will work. Second, I will color my hair the night before the gala, so no one will expect me to be blonde, as they have never seen me as a blonde. Further, let's be honest, no one at work will think of me when they see two ditzy, flirty, slutty party girls!"

Jill continued with the rest of the idea,

"now the tough part, that you agreed to last night, is you have to get a total makeover and learn to be the best party girl possible in the next six months."

And she reinforced her main point, with laser-like focus, "I don't want to make light of this, no one can know, or think, or suspect you are a guy." Jill emphasized.

I was now thinking a little clearer, thank you coffee, and asked her,

"How I could do that and still do everything else I have to do for work and the rest of our life?" How about we get ready, but only change my look the month before the party?"

She immediately shook her head left to right. Of course, she also had answers for those questions. My work was all remote, I had never even been to my firm's offices. No one ever had me even see a customer. We lived in the country more than a city or the suburbs. Our neighbors were on their own one acre lots, we had found a place that was pretty remote, so we had quite a bit of space. She reminded me, we actually had never met any neighbor within a half of mile.

Jill said if anyone asked where I was and who this blonde visitor was, she would tell them I was on an extended work assignment at a customer site, and the visitor was her best friend from the University Cross-Country team. So, if you change, no one will ever know, because no one knows us right now. She also swore that no one would even have a hint the night of the party, but only if I didn't resist and embraced everything about the change and worked it hard every day for the whole six months. I would never convince anyone with just a month of play-acting as a hot chick.

So, it all made sense, I had to agree, but I needed to know the details. And it was just a bit odd that Jill had chosen this approach. I wasn't the most macho of guys, but still! I wasn't ready to give up and told her I could do this seriously for a week or two and be ok, and I guess we could glue on some fake tits. That, it turned out, was not what my wife, with her nearly manic attention to detail had in mind at all.

Jill told me I would have to start with me living as a woman full time. Since Jane was close to Jay, it would be my new name. I would have to get implants, wearing false boobs was too hard for six months. And of course, a careful diet; I was thin from 30 miles a week, but Jill wanted to lower my muscle mass and ensure I didn't look too "manly". She told me that I needed to look the part of a young hot girl, not a slovenly white-hat hacker. My hair was already shoulder length, I told myself it was long to save on haircut costs, but I actually liked it hanging down in a pony tail or loose over my shoulders. Jill said that was a good start, but it needed work too. She had clearly thought all this through, and reminded me that I had agreed to literally do "anything" to ensure we won that free trip to NYC.

Better yet, with the fake boobs and my almost non-existent body hair and runner's physique she felt I wouldn't have to use any hormone shots, so we could continue to have fun as husband and wife, despite all the external changes. Jill assured me that was a deal-breaker for her, she wasn't about to lose her husband over this costume party scheme. She told me, and I was a little surprised, that although she liked girls on occasion, she wasn't going to go all lezbo with this plan. Jill reinforced that I would have to do the face makeup routine daily and always wear high heels so I didn't look like a guy stumbling around in drag on the big day. Jill really focused on being serious and embracing all the changes. Again, it all made sense. So, I nodded my head and maybe a bit too quickly said,

"I'm in, when do we start?"

She may not have suspected, but I had always loved the feel of my runner's tights, much less the smoothness of satin and delicate lace, and to be honest leather and other exotic stuff got my motor going. I knew I wasn't all that macho, and liked to think I was open to new things. This might be fun, and to answer all men's curiosity, I had never been in a lady's room before, I would surely get to see those hidden precincts now.

Jilly told me that the first steps were on Sunday to do as much as she could do without help. Then I had a full day spa appointment for a "makeover" on Monday, at her running buddy's place in town, called fittingly, The Total Deal. Later, on the following Friday, her very best friend, a plastic surgeon, had agreed to do the work after everyone else had left for the day to give me the right equipment, C cups to match Jill, but more natural on my slightly larger frame. It wouldn't be silly or unnatural, that would have never worked on the big night. Instead she was focused on just the right size and shape of fake breasts to match my body size. She told me finally that though we might have to buy some clothes, most of hers would fit, we just had to check on shoe size.

It Begins, Preparatory Efforts

Sunday Jill had me shave as close as possible. It was not really that hard as my hair was barely noticeable, it was so thin and fine. My hair was more blondish than light brown, especially in the summer when I was out running every day, so it didn't show much anyway. She then smeared a thick depilatory cream over my entire body from head to toe. After ten minutes of the mildly unpleasant tingling, and my whining about it, Jill pointed to the shower, where I washed the cream and all my hair down the drain. The cream reinforced the shaving, I was now baby smooth. We agreed to make that at least a weekly routine action. After rubbing a body lotion all over, paying special attention to my ass and cock she professed herself liking it so far, especially how hard my cock had become, interestingly enough, before she even touched my private parts.

I liked the effects too, I was smooth and my skin seemed so much more sensitive, in a good way. I was a bit paler that I wanted, but Jill told me that part of my preparation would include getting a golden tan to ensure no one who knew the nerdy hacker me, would see through the deception. We didn't go for the whole wardrobe effort on Sunday, but Jill did insist I get rid of my worn LL Bean terrycloth robe and spend the day in one of her satin robes. Not only was the robe supper slinky and soft, I loved that, but the cheesy leopard print patter looked pretty sexy wrapped around my slender frame. She also had me try on her shoes, luckily, I was able to fit hers, even though they were pretty tight. I could wear most of her shoes, though we discussed buying a few pair just for me.

Jill insisted I had to get to the point where I was walking in really high heels like I was born wearing them. That was going to be an issue. I was going to need a lot of practice, right away I nearly broke both ankles with her low two-inch heels. She insisted we work on it, because tomorrow I had to walk in heels to and during my makeover. But crazily, over the next four hours, we moved quickly from two all the way up to five-inch heels. What I learned was I had to alter my entire gait and way I walked. But to a runner it was just another stride I joked. I wasn't walking like a model I knew, but wasn't doing badly, and looking in the mirror with the satin robe and high heels the whole look made my legs super long and my ass was divine. Not very manly, but I looked sexy I thought. Why did I like this so quickly? And even more weirdly, I felt my dick hard as steel, which looked odd in the mirror with five-inch heels, making a tent in the front of Jill's robe.

My hair was already below my shoulders, but though it wasn't very brown, it nothing like the blonde Jill was aiming for. Jill said she and her buddy had some ideas for that. Monday was going to busy and we got our smooth bodies to bed, making love looking like man and wife, for the last time, it turned out. Everything was the same but different, my skin was so much more sensitive and Jill told me feeling me without all my hair was a huge turn-on.

She especially liked sucking on my cock and balls without getting any hair in her teeth she joked. It was hard for me to admit but this was a lot of fun so far. She loved it as I ate her out to a first strong orgasm, but I liked it better when she pushed me on my back and dropped her soaking wet pussy over my hard dick. She rode me for almost five minutes till my self-control evaporated and I came massively up inside her.

Monday Jill dropped me at the salon early in the morning. To say I was nervous would have been a huge understatement. She had put me in woman's jeans and a top and put a bra on me stuffed with pantyhose, so it didn't look too weird, but even combed out my hair and face looked at best androgynous. We got inside the salon without seeing anyone, it was really before the normal opening time, thank god. Anna, Jill's buddy took over till Jill got back from work that night and picked me up. Anna smiled at Jill,

"You will not recognize Jay or I guess it's Jane, when you see him tonight."

I was not exactly buying into Anna's confidence, and my face clearly showed that. But Anna knew the whole prize-winning plan, as did her girls. She gave me a big kiss and stressed to me that in order for Jill to get the full effect I had to trust her and her staff! I was told to change into a very short pink satin robe, over my bra and panties. I was kept in the back, away from any other customers, for most of the morning, moving from work area to work area, to get the key early efforts complete and disguise my true identity. Later I was allowed to move around in the more public spaces, but by then I was getting into the spirit of the whole makeover and not feeling any pain. After all the entire crew did make sure I had plenty of wine to keep me relaxed throughout the day.

The day was full of new and novel experiences. It included another full body massage and another application of the hair removal cream from my neck to my toes. The team also gave me slightly shaped nails and painted my fingers and toes a bright red color. That was odd for sure. Anna said they weren't going with fake nails, too much trouble, and I had plenty of time to grow real ones. She told me that natural nails were much stronger than glue-ons. Even without fake nails, my hands looked oddly feminine immediately with that bright red polish.

The biggest amount of time during the day was working on my hair. It wasn't really long enough I knew, and clearly the wrong color. I seemed to spend at least three hours being the center of attention to just working on my locks. My hair was first washed and then a strange smelling goop was spread all over my head. The stylist worked it deep into all of the strands of my long brown hair, while wearing gloves, it stunk. I was kind of nodding off, wine in the morning will do that, and the girls worked on my nails while I napped. When I woke up the nails were fully dried and the strong-smelling stuff was being washed out in an odd sink, rounded low in the front, that my head fit into. I was not allowed to see myself; all the mirrors were kept covered. But next I did feel one of the girls working on each section of hair, it seemed. I had no idea what that was for. They told me they were weaving in extensions, but beyond guessing what that meant, I was puzzled.

Finally, after another hour, and now with a very odd, thick green paste all over my face, I was ready to finish up the transformation with a group effort to take what I thought was a very smooth face from maleness to a totally feminine look. I asked, and was told the paste was to smooth my skin and close up the pores. My stylist finally peeled it off and washed my face and neck with warm scented soap. It turns out now I was ready for my first lesson on something I would have to master, how to employ on all the mysterious kinds of makeup to truly look like a woman, not some drag queen. I was told that for the entire next six months I needed to do that facial treatment at least twice a week, every other day would be better.

The team got together for a group lesson on all the different bottles and pastes, as well as the brushes, pads, and other odd looking tools that were all considered normal for a woman to use creating her "look". First, they taught me what every different item was, its purpose and what sequence to apply it. Then the lesson progressed to how to apply makeup. It was far more than just allowing the technician to give me a new look. The focus was not just on how to look appropriate for the daytime or evening, but being self-sufficient, like Jill and all other independent women, able to do my own makeup.

It was all about lessons so I could do this every day, and quickly. The team applied the whole style, explaining everything, then I was taught how to take it all off and had to do it myself. First of course I was taught how to pluck my bushy eyebrows into a thin arched, very feminine style. Looking in the brightly lit mirror, there was no way I was looking masculine for quite a while now. It was probably the most painful part of the day, and my team laughed at me and told me, "welcome to being a girl."

After the third practice, I wasn't too embarrassing in my results. The three hours of work included of course all sorts of new items, foundation to hide imperfections and my very light beard, as well as blush to bring out my cheekbones, dark eye treatments and of course bright red, retro-style lipstick. I learned to use all those odd brushes and tools. I also learned to get that super shiny lipstick effect I needed at least two layers, including a bright shiny outer layer to seal in the deep red color. It was the oddest feeling, so new, to have this thick coating on my lips, all creamy feeling, it totally changed how I looked.

All of it felt weirdly different, but were not any kind of big deal, or painful, other than that plucking routine on my brows. But that part I was actually pretty good at, plucking my eyebrows to shape them and ensure they were a thin sexy shape was easy to master. Finally, in something that sounds minor but really changed how I felt and looked; the team showed me how to add thick, long false eyelashes to my natural ones. For the first time ever, my eyelashes felt quite heavy, but they told me it looked divine. Anna gave me a page with links to makeup tutorials and got me to promise I would work on them every day for at least the first two weeks. Even so, I wasn't sure I could ever recreate this totally different look again, despite all the practice.