Not Willing to Go Back Ch. 05

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. This part takes it to the culmination, or at least the current culminating point. Time will tell if there will be a Part VI.

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Jill Confesses and We have fun together

So Jill clearly had something to add to my parade of revelations. To have her absorb everything I had unloaded on her without an explosion meant she had something big to disclose too. I looked at her, quite curious, but still a bit worn out from our adventures. She gave me a guilty little smile and started,

"since, you came clean and admitted your extra partners and stepping out, I have to come clean too. I started fucking my boss about a month ago. I'm not proud of it, and still love sex with you, but needed that rough masculine fucking to go with our more feminine fucking."

She told me the first time was when she was relaxing after a long day of meetings. She and Robert, her new boss, were enjoying a well-deserved cocktail hour. Jill told me she was dressed totally professionally.

However, she didn't realize how enticing that was to her boss. It kind of hit her when she realized her narrow skirt was so tight that you could clearly see how her sexy stockings were hooked to a garter belt underneath.

Her boss was getting into her personal space and more and more friendly. She confessed she was enjoying all of it. She was shocked to admit to herself that she was primed and ready for some old fashioned work trip seduction. Soon they were both kissing passionately in the elevator on the way to his room. She had no doubt where this was heading, and realized she was sopping wet already.

As soon as the door closed to his room, they were all over each other, clothes flying off in every direction. But Jill left her heels on, and dropped to her knees to enjoy tasting the first new cock she had been near since our marriage. After she had him hard and throbbing, she looked up and spun around dropping onto all fours.

Jill took her boss doggy style from the rear, and realized she had been missing this...she felt like a hot woman again. They did it all night long, and before the night was done, he had fucked her up the ass too, telling her that she was perfect in every way.

My wife then confirmed what was pretty obvious by this point. She and her boss had been fucking every week during their business trips. She told me that it was physical an sometimes rough, but not intimate or loving.

This time I was the one to be shocked, but what was I to say. I had already admitted and told her about sucking and fucking numerous guys and gurls behind her back. I took some deep breaths and asked her,

"can we go forward from here? Do we have a marriage anymore?"

Jill nodded yes and told me she thought so, but if we were going to allow more openness, with all my changes, more openness for each of us, then we just needed to be honest about it.

She told me that she realized we made love and fucked, but with Robert it was only fucking. I too told her that with all my other partners, it was about the sex, not intimacy or love.

For instance, Jill told me she'd like to join Steve and I for a threesome, and with an evil little grin told me she was going to buy a strap-on and learn what it felt like to pound my ass. I smiled in relief and told her my ass was always hers to have.

She also said that she was sure her boss would have fun with both of us the night of the party, but not a word before, she lectured me. She told me she loved Jane, and all our adventures, but was still determined to win the big NYC trip at the party.

Her boss still had no idea of the whole plan, and simply thought that Jill had succumbed to his repeated advances and masculine charm. But she said he was pretty kinky, so it was worth a try.

Soon we did meet up with Steve, and he was more than a little happy when both Jill and I went down on him, taking turns swallowing his shaft and licking his nuts. We made sure, when he came in my mouth that Jill and I passed the cum back and forth. Sharing is sharing after all.

After Steve recovered, he took turns plowing both of us. All in all, a fun evening for everyone. We basked on the glow afterwards, all wrapped up on our big bed, realizing this had been fun for everyone.

This wasn't something we had ever discussed or even imagined, but it turns out we were both turning into, or had always been, sluts.

Jill also did surprise me soon afterwards, only a few weeks before the big party. She came home on time, but then called me upstairs to the master bedroom. I figured she was horny, but not the way I had imagined. I had totally forgotten her vow that she was going to own my ass.

I discovered her nude to the waist, with sexy heels and latex-trimmed thigh highs and garter belt. But the big surprise was what was hanging between her legs. It was a very realistic large black strap-on. She also had a studded collar and short leash.

She told me I was her servant bitch tonight and to get busy. After she collared me, she had me show off my new oral skills on her fake cock. She was totally into it, thrusting back and forth and telling me to swallow her dick. I proved to her I wasn't kidding when that whole black dick disappeared down my throat.

After her toy was totally wet, and she had finger-fucked my ass with K-Y to get it ready, Jill fucked my ass for at least fifteen minutes. It felt different than a real cock, but was a lot of fun.

She was getting more and more energized, moaning and encouraging me with a really filthy mouth,

"come on you little slut, start to move those hips, work those ass muscles, or you'll regret it."

I got into it rotating and thrusting in time with her and practicing squeezing down on her fake cock. Then I realized that it was a strap on with a smaller extension that filled her pussy. She later had a big smile on her face, as she disclosed it also had a ridged knob, designed to rub right on her clit.

No wonder, soon after I came all over the bed, Jill collapsed on top of me after what seemed like a world class orgasm. She pulled her well-used strap on from my ass, but didn't try to force me to lick the fluids from it. That was good, I hadn't had an enema today, and it was pretty slimy.

The Party, was it all worth it? Life goes on...

Now it was about three days before our big test. We had to convince everyone that we were two hot party girls, and not husband and wife. Jill gave me the plan for that day. It was all arranged.

She had arranged a complete makeover at her friend's salon the day of the party. I also stopped in for a little more work than I had been paying for every week.

We got highlights for our hair and special fancy makeup. Jill also got serious blonde highlights to bring her about half way to all blonde. We had special matching tight short dresses, to match our "valley girl" personas. We checked into our room at the hotel and got ourselves ready for the party. We had all been given special passes, so no non-employees could sneak in and spoil the contest.

Jill and I posed for the photographer at the entrance. We played up the whole Valley Girl Shtick, with the accent and silly phrases. We also made a point to constantly play with our hair and giggle at every man's comments.

Everyone was puzzled by who we were. Other folks were guessed pretty quickly. They hadn't really tried too hard. I did hear several catty women, in the ladies' room comment on how they wanted to know who the two slutty, ditzy bimbos were.

We did have to deal with some very friendly dancers, most seemed to have their hands on our asses and grabbing a bit of our boobs. And we both noticed there were a lot of hard dicks after we finished each dance.

At the end of the evening we had a scare. A couple was voted best costumes for their Dracula and his female vampire servant, but the panel quickly guessed they were the finance director and his wife. She was hot though. I had no idea a finance director could score that kind of hot woman.

We had been in second, but what made the difference is no one had any idea who we were. A few accused us of sneaking in, but Jill and I showed off our passes and laughed at them. Finally, the panel admitted they had no idea.

When Jill identified herself, quiet serious Jill was a blonde Valley Girl and I was her husband everyone was flabbergasted, even Jill's boss. We had won it all.

So, the audience was laughing and aghast at the same time. The reaction of the guys who had gotten all hot and bothered dancing with me was particularly funny. A few looked horrified, a few looked shocked, and some had a silly grin plastered on their faces.

But now we had to collect the prize and figure out what was in our future...what did our marriage mean and how would we behave going forward? The simple question was, now what?

It turns out life went on as it had for the past six months, but now with full and open transparency. The very next night Jill hosted her boss Robert, at our townhouse. We got very drunk and very friendly. He was intrigued by me, and maybe a little nervous and guilty. It all worked out as I told them to go for it, but wanted to play too.

Jill loved getting it doggy style from her boss while in a sixty-nine position with me. She was licking on my shaft as I took turns licking her clit and her boss' balls and shaft. They both had pretty serious orgasms, as did I, but then I sucked his cum from her pussy, causing Jill to cum again all over my face.

We kept it up all night long. I got to fuck my wife up the ass, a first. But then in a fair play turnabout I took her boss deep inside my ass, and Jill ate all his cum out of me. Now at least Robert knew we really weren't that boring, running obsessed yuppy couple people had always seen us as.

And after that weekend I had to admit I had finally come to a firm decision. I had no desire or interest in cutting my hair, having the removal surgery, wearing any male clothes ever again, and thus returning to boring old Jay. Jane was who I was and also the identity that brought me the most happiness.

I had a heart to heart conversation with Jill. She really wasn't surprised. She told me it was actually kind of cool. She got to live with a smoking hot husband, who she could go clubbing with and pick up dates, but she still got her husband's hard dick when she wanted it.

Our adventures continued, of course. I needed for Jill to meet Steve and his friends. So, I went for the slut look with fishnet hose, high heels and black lingerie. Steve had come over with three mutual friends and Jill got to watch me go into total slut mode.

I had them play with my cock while I sucked all four of them off at the same time. Jill was a little wide-eyed as I fisted or sucked all four hard cocks and then swallowed all their loads. I didn't want to let any go to waste. Each time I smiled over at her, opening my mouth so she could see me swirl the load around my mouth and then swallow it.

That was just a warm up to ensure they had the stamina to do everything I wanted. As the night went on, I used the guys to show Jill every combination possible. I was fucked up the ass by each guy, as I sucked the next hard. Two of them even enjoyed sucking me and having me bend them over also.

All in all, I finished with ripped hose, ruined makeup, and was totally sweaty. The guys were finally limp, but they had certainly gotten a sexy, busy evening. Throughout Jill had sat across the room, in her own hot lingerie

She got totally into being a voyeur. I saw her as I was on my knees and then on all fours staying busy. She would be fingering her hard clit while she rammed my huge anal training dildo into and out of her pussy.

During quiet periods I literally could her the wet sounds as she pounded that toy into her hot body. When my friends left Jill told me it was the wildest thing she had ever seen. Her entire midsection was soaking wet, so what was I to do?

Of course, I fell to my knees and buried my face in her bald wet pussy. I ate her relentlessly, bringing her to two amazing orgasms, the second while I played with her clit as my tongue was deep in her ass. I guess Jay as officially forever in our past now.

A few months later Jill laughed as she looked up from the bed one morning. She got to sleep in after a long business trip, but I had agreed to meet some clients in my cash-only consulting business at 10. So, I was quietly trying to get ready, without waking her.

I was wearing hot a hot black lingerie set, that included fishnet stockings. I matched the underwear with a kinky set of spikey black platform stilettos. On top of it all I put on a tight red satin blouse and black leather miniskirt for the day. As I was facing away from our bed, you couldn't even see my hard dick under my tight thong.

Jill grinned and told me that I was most definitely not the man she had married and she most definitely approved of all the changes. She told me to finish my meeting and get back home to fuck her, if I knew what was good for me. As I went to the bedroom door, I grinned back at her,

"baby I will not only make love to you, I really want to fuck that tight ass today."

Jill raised her eyebrow and smiled back devilishly,

"only if you tongue fuck my ass first lover!"

Yes, I might not be the man she married, but this hot slut wasn't the innocent girl I had wooed either.

Later that week I surprised her again. I wanted to repeat an encounter we had had right after my surgery. So, I was waiting at home half on the floor, half on our bed. I wanted to look all gurl for her, and had the soft lights on and a bottle of bubbly chilling.

I pulled on a red and black set of lingerie with some of my super sexy black heels and the boldest, brightest red lipstick I owned. The bra barely covered my nipples and it included a super sexy six garter set of suspenders.

As Jill came in out bedroom, ready to relax after a long day at work, she smiled broadly. I looked over at her, all dressed for work still, and told her I needed to get fucked so bad it hurt

She immediately peeled off her outfit, leaving on her own sexy set of lingerie. We kissed and groped for a while till she went and found her strap on, and fucked me till I screamed and came all over the sheets. Then she made me lick it up, as she relaxed on top of me.

Later we got our energy levels back up, drinking most of that bottle of champagne. We then enjoyed an extended sixty-nine session. I really got into her taste as I focused on her clit, but made sure she felt one hand in and out of her soaking wet pussy.

I wanted to hit all her erogenous zones, so used my other hand to indulge in some ass play. I toyed with her rear, but then, lubed up two fingers and gave her a good ass fucking as I ate her out. Likewise, Jill made sure she sucked me deep inside her, but also massaged my P-Spot with a wet finger, over and over to make me feel my own fun.

I thought to myself, this is a marriage made to last!

Relocation and Completing all the Steps

So, we didn't know it, but our time outside Portland was soon to end. Jill had in fact been tapped for promotion and was moving up in her firm. But the Portland operation was just too small. She was offered a big promotion and position in the larger LA operation.

We sold our place, and at the same time donated all of Jay's old stuff to Goodwill as we packed up our house. We found a cute little mid-century place about four miles from the beach and Jill and Jane moved to LA.

California was great in more ways than one. All the neighbors only knew that two hot girls had moved in. I was able to easily change my gender and name on my license in California to female and Jane.

Since Jill had always kept her maiden name, we stayed married, but had a lot of freedom to do everything we had grown to love. As we finished unpacking, storing my huge sexy wardrobe in half our walk-in closet, Jill looked over at me and asked me if Jay was really dead and gone forever.

I looked back at her, wearing a functional but sexy outfit of yoga pants and a low-cut sleeveless top, with a cute pair of slip- ons and smiled back at her,

"look at me lover, what do you think? I believe it is safe to say that Jay stayed in Oregon, and the only one living with you here is Jane."

Jill nodded and gave me a hot kiss while she also played with my nipples, and then laughed,

"cool, I thought so, but wanted to be sure we were moving on. I still love my spouse, but now we seem to be able to do a lot more together."

Changes continued of course. I blamed the new LA lifestyle. I decided I didn't want to be so fit and slender. I continued the hormones and made some other changes, that meant another surgery.

Jill also decided that life in the sun meant some more changes for her. It started with a short sassy blonde remake of her longer brown hair. It all seemed to match our sun-centric, almost hedonistic new life.

We got very comfortable in our new home, embracing our new looks and a much more sexually active lifestyle. Jill got to enjoy being a blonde, and didn't want to go back for a while. She told me that the sassy short curly style wasn't so far off the wig I had worn to have my fun with Steve.

She also surprised me when she got her pert little nipples pierced. She didn't flaunt them, but once she got naked it was clear she wasn't at all the good little girl she appeared to be at work.

It was one more overt sign that Jill as well as I had changed on the last year. Of course, when we went out, she showed them off at every opportunity, it attracted immediate attention from guys and girls.

Jill didn't just admire my clothes and huge sexual drive either. Her own wardrobe was getting much sexier and less dowdy. She looked like a hot slut whenever we went out, and could be as hyper-sexual as I was.

She was definitely all about the pleasure now, not just staying all vanilla. She like girls and boys and gurls now. Of course, how could she not like all three while she was married to me. Jill confided that after sleeping with me, and how I straddled the gender line, she was really enjoying women too.

That was only a little bit of a surprise. I now had time to reflect on what had gone on, all of our changes, but of course most specifically what I had gone through and embraced.

I now understood that my feminine side, the one that reveled in the lingerie and silky, sexy clothes and the endless visits to the beauty salon, was more powerful than my biological male identity. I just seemed to not only enjoy it so much more, I was far better at it, and not just in terms of sex.

I could rock an outfit, almost automatically knowing how to pull it together with accessories and shoes. Yet another hidden talent I had discovered. And I was so used to being Jane I realized all my mannerisms and reactions were all gurl now.

I never regretted my choice or had any desire to go back to being Jay. I embraced all facets of my life, and decided to go an even more girly route. I had a small additional surgery to be a bit more enhanced. I was now straddling the line between a C and D cup.

It didn't help my running, but really helped my curves. Of course, I loved the increased attention I got in bars and nightclubs, with or without Jill. I also got a permanent prescription to keep on a hormone maintenance dosage. And naturally, I found a salon where I could keep up my weekly pampering.

When Jill saw me the morning after all the bandages were off, in the California morning light, she gasped. With my thong pulled down to show off my shaft, and my larger tits giving me a much bigger set of curves, she loved it.