Not Willing to Go Back Ch. 04

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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Testing the Market, Expanding my Stable of Partners

I had decided to see if I my charms were compelling, but not just for Steve. So far, I had only been comfortable fucking Steve and his close friends. Could I spread my wings and pick up a total stranger? I hit one of my favorite places on a Thursday, trying out a new pair of heels with a slinky black outfit.

The heels were a full six and a half inches high, and made me look sleek, not the normally petite Jane. I went kind of classy, but really full pickup mode. I was wearing a new, pretty expensive dress, and wanted to know if it had been worth all the money.

The dress was black, pretty much the best color to contrast with my tanned skin and long, straight blonde hair. It was knee length, so you would think it was refined, but not when you looked carefully.

The dress had several bands of very thin mesh below the waist. That meant that my thigh highs showed clearly, and my legs, to about six inches below my panties, were on display. The silk dress was skin tight, outlining my tight ass nicely.

Up top, the dress covered, but showcased my tits, and that same mesh approach showed off most of my back, and the fact I was braless. My makeup was perfect, and the dress refined, but that large amounts of mesh panels made it quite sexy.

Showing off all my curves and shapely legs, I already thought it was really worth all the money it had cost. In one of my favorite bars, I enjoyed one of my favorite drinks, an original Mai Tai, free of course, and surveyed the field.

I located one of the guys I had flirted with before, and oddly enough, hadn't gone any further with. Dressed in my high fashion outfit I could tell he had no idea I was that girl. Of course, the last time I had toyed with him I had been wearing a short latex skirt, thigh-high boots, and a satin bustier top...tonight was a little different.

Not to mention I was taller tonight and my hair was not some curly cloud on my shoulders. But, regardless of all, that he was pretty quickly giving me all his attention. He was totally smitten, especially once he recognized the taller me, with long straight hair, as the slutty girl from two weeks ago.

We got reacquainted. He wasn't a total stranger, but very cute. I decided to bend my rule about picking up a total stranger. We talked and snuggled in a quiet corner of the bar, clearly we were both into each other.

His hands were all over my ass, and he sneaked in a few caresses of my nipples. I was totally hot for him too. I sucked on his neck and rubbed his dick till I thought it might explode right there.

He totally was into my efforts to get his motor running. In only a few minutes he was really pushing me to come back to his place for some fun. I laughed and told him he didn't have to beg; I was going to fuck him regardless.

I was torn on how to say yes, disclose my extra equipment, and not scare him away, so we both could have the steamy fuck we wanted. I had just about figured it out, when his phone buzzed.

His cousin was going to meet him in the bar in thirty minutes. This made it more complicated, but maybe there was a better payoff with two instead of one guy? I had thirty minutes to get this whole thing set up.

So, I stayed with the first guy, Roger, in the dark corner, now shamelessly rubbing his dick first through his jeans and then right on his hard cock after I fished it out of those tight pants.

He was beside himself, especially as I had started to lick and bite the sensitive side of his neck. I started to tell him that I wanted to swallow his first load, before he and his cousin fucked me senseless. Roger was hooked.

But I slowed down and pulled away to stare in Roger's eyes. I told him I had to be honest and if he wanted to walk away, now was the time. I figured it was safer to make sure he knew I had a hard cock under that tight designer dress out here in the public area of the bar.

I told him I hadn't been born this way, what he was seeing was the result of a lot of hard work, and some surgical enhancements. It was obvious that Roger's first thought was my tits were fake.

I realized that in a second and rethought my approach. I added more detail. Telling him that yes, my tits were fake, and they needed to be as I started as Jay not Jane in life. He clearly didn't believe me, even reaching under my dress.

I batted his hand away, telling him that of course my fun parts were tucked away, I mean how could I wear this outfit otherwise! Crazily enough he told me he was still hot for me.

We met his cousin and soon were on the way to Roger's apartment. We got some more drinks, and I sat between the two of them, getting kissed and stroked all over, while I played with both their dicks.

Roger was really enjoying the deception, but after about thirty minutes, he grabbed another bottle of wine and came clean with Ray, his cousin. Ray, like Roger had been, thought it was all a joke at first.

But after he felt my dick pushing hard against my gaff, he believed me. But as Roger had said, he was still ready to get naked. I went to the bedroom, and had them follow in about ten minutes.

I had stripped off everything but a barely there sexy bra I had worn that outlined my tits, but didn't cover them a bit and put all the rest of that expensive new outfit off to the side on a chair. Of course, I did leave on my thigh-highs and heels.

I called out and had the guys come back, my dick standing proud as I spread my legs, nearly naked. I posed, smiling on the bed, with my arms under my breasts, pushing them up, as that tiny lacy bra wasn't going to do that. But the guys loved the look of that lacy black bra against my C cups.

The night was a lot of fun. I got to play around with a new pair of guys and realized many people, beyond Steve and his friends, would do anything to get me to bed. I first sucked both guys dry to take the edge off, telling them that it was just the first part of a long night of debauchery.

I then took turns sucking them deep into my throat, while I told the second guy to lube up and fuck me. Each of them found out how tight my ass really was, and how ass muscles could milk a dick.

One of them, I think it was Ray, also showed me how good it felt to get rimmed, he made me so wet, including pushing his tongue as far as he could up my ass. I'm not sure I really needed it, but then he made sure to use a generous amount of K-Y to get me really ready.

The only surprise of the night was when the macho cousin Ray asked me to do him. I thought he meant sucking him off again, but he got on all fours and raised his ass instead. I had cum once already during the ass pounding, so was more than ready.

I lubed up and for the first time felt what it was like to fuck a guy's ass. I had a lot of fun. First, I rimmed him out and tongued his ass before thoroughly greasing him up. I then gave Ray my first ever dicking, including a friendly reach around of course. A great end to the night.

As we finished up, the two cousins lay on either side of me in the bed and surprised me. I got another confirmatory signal of hot guys thought the new me was. Both the guys nearly begged me for my cell number so we could coordinate future hook-ups.

They were not coy at all, they told me it had been more fun than they had dreamed about, and Roger even admitted he was envious of Ray when I slammed my gurl dick into his ass. Roger told me he wanted to make sure I was ready to break him in next time.

Boy this was going beyond my dreams as far as how easy it was to seduce and get wild with almost any guy. And I had to admit, it felt good to finish the night fucking a guy, not just receiving a hot cock up my ass or sucking off a throbbing dick.

Can I Ever Go Back, Another new Experience!

I soon got to enjoy another groundbreaking episode with a friend of a friend. I was now really starting to get into my comfort zone as a slutty seductress. I was now so comfortable as Jane; I wasn't surprised when I realized I was now almost always the center of attention in any bar I entered. It actually felt normal.

This time it was another friend of Steve's, a guy I had never met. He struck up a conversation one Thursday night in the bar, asking me if I was Steve's hot friend. He was big, buff and friendly, and also very black.

I had never been with anyone not white, man or woman, so this had me intrigued. I also smiled to myself, would I find out with Trey that all the black cock size urban myths were true?

But if I was neutral to intrigued, he was totally into me, as I sat perched at the bar, my high heels taking up the seat next to me. I couldn't tell if he was attracted to my blonde hair, by my brand new aqua colored latex minidress, or those matched latex stockings, or maybe even the super high stripper heels?

But regardless of what attracted him, he wouldn't leave my side. He couldn't take his eyes off of me, and kept on running his hand over my legs and across my mid-section. I too was very interested, thinking yet again, were all the stereotypes right, was he really packing?

However as big as he was, I was a little worried how he would react to my unexpected parts. I knew that a lot of guys could get violent when they found out what a trans gurl was, and this guy was big.

I tried to delicately bring it up and Trey stopped me cold,

"baby, Steve told me all about you. I am all in, you are what I want tonight, after all, variety is the spice of life."

Trey had keys to Steve's condo, and we adjourned there after only a couple of drinks. I learned that black means bigger, at least tonight it did. Trey's cock was at least three lengths of my fist, so I knew I would never get him all the way down my throat.

But I made a great effort, jerking him off, while sucking his knob. I was running my lips up and down his length, and boy a lot of dick on this man. At a certain point I felt he was getting close to blowing his load, and neither of us wanted that.

But I also made sure I gave Trey my phone to take a pic as I was nibbling on the tip of his dick, while holding his massive shaft in my hand. Later when I showed it to Jill, she said it was the biggest dick she had ever seen, and was amazed at the slut I now was.

I told her, as I recounted that night, that I had been a little worried, it was about as big as the massive toy I had trained on. I then told her that I was so horny at that point that no way I wasn't giving that huge cock a try.

Trey was ready for more fun as I grabbed his hand and led him to Steve's spare bedroom. We kissed some more while I used my hand to keep him interested. He was such a big guy, but wide and ripped, not tall at all. Looking in the mirror, especially with my heels off, I looked tiny next to Trey.

I couldn't wait to have him inside me. But I was not in charge of all that.

He had strong ideas, and the muscle to make them happen, but It went a direction I would never have guessed. This was the most macho guy I had met since I started as a gurl, and boy did I read him wrong.

In a big surprise Trey pushed me down on a couch in the spare room, which seemed to also be a TV room. He buried his head in my crotch, something I was not expecting, and took all of me into his mouth and throat. This surprised me as I had given no sign, I really wanted to receive any oral favors.

But this was still an awesome scene as far as I was concerned. I tried to return the favor, laying on the couch and pulling him next to me. I tried and tried to swallow his rod, but he was just too big.

Still it was my first sixty-nine while a gurl, and I really liked it. Trey took care of business, I totally lost control and came, and he didn't say a word, he just swallowed it all.

Next, we got down to business he pulled me up onto all fours on the bed. He used some lube that Steve had left on the side table. After I was fully greased up, I got to experience what ten to twelve inches felt like pounding your ass.

In summary, it felt great. It seemed like his massive dick was going to come out my throat. I felt really good for the five plus minutes he slammed me. There was of course some discomfort as I stretched to fit that huge cock, but really not all that much.

I also got more comfortable after a couple of minutes taking all of Trey's huge dick. Then I showed my skills and freaked him out as I started to milk his huge shaft with my muscles. As he went in and out, I did my rippling trip, squeezing him from deep inside all the way back to my asshole.

That was enough to send Trey over the edge. He gave me the expected huge volume of cum, filling my bowels. Wow, I wasn't going to avoid diversity in my partners from now on!

Afterwards we relaxed, and I told him that his was the biggest dick I'd ever had, bigger even than the biggest dildo I had trained on. He grinned and told me he'd never had a T girl take even most of his dick, much less all, and I was a rare talent.

Trey said that only the most experienced girls could take him, and never on a first date, so I was a very rare partner. So, no big surprise, I made sure to get Trey's number. I laughed at him as I told him,

"I won't say I'll never go back since I went black, but I'm for sure putting you on regular rotation. And I am sure, very soon, I'll be swallowing that whole dick."

He laughed with me telling me, "baby, I'd fuck you twice a week if you'd let me, so I'm up for your challenge."

Going for Quantity and Confronting the Future

About a week later, Steve called me up with an offer I had to take,

"hey Jane, if two on one was fun, are you up for four or five on one?"

I was thinking that I was sliding onto very steep slope, but agreed to meet the crew at Steve's condo on Friday night. Jane was not back till a morning flight on Saturday, so I had a rare Friday night to have fun.

Steve had told me that no one believed the pics and the stories and he knew I was slutty enough to love a session of four or five dicks just for me. With Jill gone till Saturday I had some recovery time. And boy did I need the time. It was five on one it turned out.

The guys were not just curious about fucking a hot gurl, they had big stiff dicks that seemed to never go limp. And with a five to one ratio, someone was ready all night to suck or fuck with me.

I spent hours with a dick thrusting in my ass, while I sucked another and had my hands on one or two more. Oddly enough, after a while, when I had cum three times myself, I was still enjoying it, but my dick didn't even seem to be willing to get hard anymore.

But the guys stayed hard for two cums a piece, but it might have been more, I lost count. The bed was soaked, I was soaked, and I thought I might need a crash diet with all the calories I had swallowed during the session.

My red thigh highs were ripped and stained, and my hair was matted with dried cum. By the time I got home, at nearly dawn on Saturday, I was ready to crash. Everything was so messy all I had on were heels, those ripped stockings, and a raincoat I had borrowed from Steve.

I took a long hot shower, and collapsed till about an hour before Jill got in from her trip. I rushed around, getting dolled up to show her I had missed her. If only she knew what I meant when I told her it was ok, she was traveling so much,

"baby it's ok, I've been keeping busy even with all your travelling." I added, "you know I attract a lot of attention walking around like this."

She gave me an odd look, clearly not sure what that comment meant, but kissed me and told me she was glad to be home. And she did love my cute top and long skirt, with some sexy ankle boots.

We had a quiet Saturday night, which was good as I was still thinking I had swallowed about a quart of cum on Friday night, and how would my body digest it. I was surprised my breath hadn't tasted of it when Jill and I were kissing.

Then, one day, near the end of the fifth month since I'd started to train for our big Halloween competition, Jill came home unexpectedly around two o'clock. She was shocked and froze.

She had clearly expected to see Jane, but not looking so hot. She must have expected me, like before the changes, to be hacking away in sweats and a ratty t-shirt. Instead I was dressed in a sexy silk robe over my lingerie, with some fishnet thigh highs.

I was of course fully made up with big pouty lips and even wearing a trashy choker, and perched on high platform heels at my workstation. I must have looked like a stripper at a club who was hacking during a break from dancing.

Jill was clearly a little surprised and asked me if today was special. I told her no; I dressed this way every day. She paused and clearly was thinking things through,

"so, maybe I was off base feeling guilty recently about forcing you to dress and act like a woman for all these months. Jane tell me honestly; this isn't a hardship or pain to train for the big prize?"

I smiled and kind of gushed out with an answer she clearly wasn't expecting,

"no baby, I love how all this lingerie and pampering makes me feel. How I look now is crazy hot, and everyone's reaction to this new me really turns me on. It's so hot to be dolled up every day, totally not how I ever saw myself before.

Then I paused and figured it was time to start addressing a dangerous subject,

"And baby, I don't know if I can go back to being boring old Jay, to be honest. This 'new Jane' is just as much me as the old ratty Jay. In fact, in a lot of ways it's opened new doors for me. I love being sexy and slutty and even almost a bimbo some days."

Jill was deep in thought for quite a while. I guess she was digesting all that I had laid on her and not ready for more discussion of what I had become and what was ahead of us. I kept on catching her staring over at me, head tilted to one side. I realized that last part had been unexpected for her.

We had a quiet dinner, but despite the deep conversation, still enjoyed an evening of oral fun. This was what she seemed to like more and more these days. I had to admit, she tasted great, and I loved it when she had at least three orgasms from my tongue and fingers.

More than One Confession It Turns Out

The next day was Saturday, and I decided it was finally time to come clean, so to speak with Jill. We woke up slowly, first I wanted to get her relaxed so I played with her breasts and clit and then went down on her, while she was still half asleep.

She tasted great, and got really wet and aroused, moaning and rubbing her own breasts, cumming in less than five minutes. I figured she was now awake, and maybe more accepting of what was coming next.

We cuddled again, and I told her I needed to tell her everything, even if it cost me everything, I owed her that. I tried to make it clear that some of it wasn't going to easy to hear. She was now wide awake, staring at me with a look of pure apprehension.

I needed to take it down a notch, so I told her to relax in bed with the morning coffee I had brought her. I smiled and told her I was going to give her a fashion show, and chat during and after about what I was now.

First, I left her for about 45 minutes. That allowed me to go to the spare bath and bedroom down the hall and get all dolled up. I showered, did my hair and put on a very different outfit from what she usually saw when she came home from work each night.

This first outfit was definitely not for work. It consisted solely of a set of latex pieces. Up top was a sleeveless low-cut top in black and red that I wore with my favorite latex leggings, which were inside a pair of knee-highs, fetish type high heeled boots. It sounded kinky, and was, especially with my wild blonde hair, long red nails, and bright red lips.