Not Willing to Go Back Ch. 03

Not Willing to go back Part III

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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Embracing all my options and Developing Skills

In the next two weeks I decided to take my sexual adventure further. I had made my decision. I was going to really see what would sex be like, beyond oral, with a guy. But to take that big step, I realized I needed to get myself ready.

It had been a tight fit to push even my index finger up my rear. How would I not get ripped apart or explode in pain when a real cock penetrated my tight ass?

I surfed the web to try to understand what one used to get ready for anal sex and how much it would hurt. There was a lot on line, of course, and a lot less that seemed at all helpful, of course. But I did find some training programs for men or women on how to get ready for anal sex.

The common thread was that with daily work, and the right tools and exercises this going to be ok. In fact, several promised readiness for any size cock in only two weeks. So, I now had a plan.

As I was walking around each day in my various high heeled shoes as part of my training, I started to build into my daily routine another training session. This included various fake cocks to ensure I would be able to handle anal penetrations.

It started with of all things, a pen case that was long enough and not very wide. Progress was slow, and at first a bit painful. But the feelings as I hit my P-spot were very different, very arousing but different. I got to like having my ass slippery with lube I noticed.

I graduated, in only a day, to one of Jill's smaller vibrators, then her bigger one, but knew it wasn't enough. Both of those toys weren't even my size, and I was at best average for a guy. However, the strong erotic sensations, as I penetrated my ass, already signaled I was going to like anal sex.

So, encouraged, I went into the least-seedy adult store in our town. I bought both a series of butt plugs as well as three, different sized vibrators. The smallest vibrator was normal sized, six inches. But the mid-sized one was a bit scary at eight inches and the largest was over ten inches and very wide.

I began to use the plugs every day, and in less than a week could take the biggest one easily past my sphincter ring and work all morning with it deep inside my ass.

I also used the vibrators each day. Starting with a six inch version, in less than a week it was no big deal. I was soon using the eight incher to train myself. All the vibrators had suction cups to keep them stable, allowing me to practice riding the hard plastic dicks. The vibrations deep inside me always triggered an orgasm, intense, but different from my other cums.

I finally went to the biggest test, a vibrator that felt like it was the size of a baseball bat. I had measured it and it was much wider than my dick and listed as over ten inches long. I was worried I would tear myself, but as the eight inch toy was causing no pain and lots of pleasure, the second week I figured I needed to try a porn-star sized fake dick.

That massive toy was called the dominator, and more than a little scary. But I figured if I could take this up my rear passage, any real dick would be easy.

Like the others it had suction cup option. So, during the second week of my training program, after wearing the biggest butt plug all morning, I decided to go for it. I stripped totally naked, but did wear a pair of spike heels. I had learned they allowed quite a bit of leverage.

I attached that huge device to the wood floor in the area right off the kitchen, of course with all the blinds closed. I had towels and a full bottle of lube to assist my efforts. I decided I would see if I could get it all inside my ass, before I messed with the remote controlled vibration modes.

The session started with a serious amount of discomfort. That toy was much wider than the one I had been using, and my prior toy wasn't narrow at all. However, after about a minute, and about half a bottle of lube on the toy and all over and in my ass, it slid past my sphincter muscle.

Wow, it wasn't hurting all that much, but could feel my whole pelvic area stretching to accommodate the toy. I was pretty amazed when I got the whole toy in my ass in about five minutes. I could honestly say I had never felt so full.

Soon, on my first session with the dominator, I was bouncing up and down almost the full length of the toy. Combined with setting the vibrate mode to high, I was loving this. It honestly had hurt a bit at first, but with all the lube and prior work and patience I had made it work.

I then got a look over at the mirror. I immediately thought it was very kinky and hot. This naked TGurl was taking a huge fake dick up her ass. That gurl was totally ripped and sexy all the same, grinning as she fucked herself. I found out if I played with my tits as I bounced up and down it both looked and felt a lot sexier, using those stilettos for extra leverage.

As I reflected on the two weeks of work, I realized something. It was crazy, but the stimulation and the very act of fucking myself usually made me cum, even though I was not even stroking my own dick. It wasn't easy, but in about ten days, I had ensured I would be able to take almost any size cock with no concerns or pain.

Now, I wasn't sure if I really would go through with it, or how I would do this, but my body was going to be ready. I was now also very confident in my oral skills. Working with Jill's dildos and my new set of toys, I now could swallow a pretty sizeable cock all the way, and was sure I could make any guy, no matter the size, cum in buckets.

So now my ass could take, with no issues, a fake cock that was both very thick, and over ten inches long. I also could swallow whole an eight inch dildo, so I knew I was a pretty talented gurl. I felt my skills were all in place to take the new me, as far as I wanted. But how far was that?

What helped was that Jill was taking more and more business trips, so I had longer and longer periods during the week alone. Jay was now a distant memory; I was Jane twenty four by seven now. I was now totally into a female rhythm and routine, so her trips were no big deal that way.

I didn't even have to think much as I pulled my outfits together each day. My makeup and hair skills were as good as Jill's anyway, I had to admit. I also realized I didn't even dream as Jay anymore; my dreams were of Jane exclusively.

I was better at being a slutty chick than being a guy anyway I now realized. Where Jay had been quiet and blended into the background, Jane was riveting in any room she was in. She got the immediate attention of any man, in a way Jay had never been able to with women.

Jill was always very frisky when she returned from her trips. So, unless she was feeling guilty, every time, I decided I didn't have anything to worry about. However, after-trip sex wasn't enough, I still felt driven to hit the clubs pretty much every night she was gone.

But still I knew if I hadn't been very macho before now, I was the least macho husband in the world at this point. In fact, although with the modern hormone mix, I was fully functional as a male, no one had seemed to suspect for the last two months that I was really biologically a male.

Especially with my smooth skin and great tits and ass, I wasn't looking at all halfway anymore. With my tanned body and hot outfits on that great bod, I was looking all gurl now. The fact that my makeup was always perfect and my own hair had grown out to a full wild mane of blonde hair didn't hurt either.

And I had to admit, feeling a guy pull me close, kissing and rubbing my body, and then later dropping to my knees for him, felt powerful not passive. And though I had trained my body for the final act, I wasn't sure I could cross that line. Getting fucked seemed to be far more of a step than sucking the several dicks I had enjoyed so far!

I would get bored after all day working on customers' computer networks so continued to go out for drinks and dinner when Jill was traveling. I sometimes had to pay for dinner, but was weirdly proud that I hadn't bought a drink since my transformation got going. Working my bar slut mode with the guys was amazingly effective.

I had figured out how to pick up unattached guys, my outfits drew their eyes and attention. But it was my flirting, rubbing and stroking their body, while smelling of expensive perfume, that kept them keyed up.

It was very clear if I wore anything skin-tight, and short, especially in leather or latex, I was going to get what I wanted. I found short latex or leather skirts with thigh-high boots always got me what I wanted. But I wasn't surprised, guys are pretty simple creatures.

I enjoyed the casual kissing, it never ceased to turn me on to be kissing with my heavy lipstick, often leaving those tell-tale marks on necks and collars. Twice I decided to branch out, really living the slut persona.

I approached the two target guys while their dates were in the ladies' room. I came up on them and rubbed my tits into their backs and pulled them on the dance floor, shamelessly rubbing all over them.

One time the guy stayed true to his date, telling me after the dance that he wasn't available, though his dick had felt pretty available as it pushed up against my stomach! However, the second guy was hooked. He told his date to have a nice night, he was with me now. She was shocked and pissed!

Wow, I was turning into a very proficient slut. We necked for a while as I rubbed his cock in a dark corner, before I took him into a back room to suck him dry, swallowing his cum with a big smile. He was probably amazed that a girl he had met less than an hour before had swallowed his cum.

I got to like the feeling, perched on my heels, of sucking and biting on their necks, leading to some very heated petting and kissing sessions. I was usually wearing my more restrictive gaff, so it didn't always feel great, as I was always super aroused when I teased the guys. But I was worried with my less restrictive gaff I would have shown a big bulge.

I got very good at taking guys upstairs and devouring their dicks...the taste was starting to be a reward for me. In another weird development, I starting to look forward to not just tasting but swallowing my partners' cum.

It was always a little different tasting with each guy, but I had a feeling of power as I drained them. I usually tried to kiss them; the keepers where the ones who didn't pull away, but locked lips with me. Those got to exchange cell numbers with me. The others...no way.

In fact, I had started to develop a whole bag of blowjob tricks, beyond what I had been copying from Jill's formable and varied oral standard tricks. I had a whole series of little techniques that I could mix together in several approaches, but all seemed to work equally well.

I liked for instance to get the head and shaft very wet, so I could move up and down the shaft really fast. Then I would move back up to the head and suck on it so hard that I could feel my cheeks totally change shape with all the sucking. When I pulled that trick, every single guy let out a series of loud moans in response. A couple of guys shot off in my mouth right then.

I also grew to like sucking on a guy's balls while jerked him off, but that was much better, I learned, if he liked to shave off his hair. All in all, I was pretty surprised that I not only got turned on, but judging by the loads of cum, was a pretty good dick sucker.

I think I grew to have a bit of reputation at my favorite bars, I definitely wasn't just a cock tease, I kept my end of the deal, nearly every time. It seemed that word got around.

I had been at the bar, when guys didn't know I was nearby; they described me to friends of theirs as this hot slut who would never hold back and had given them and their friends blow jobs upstairs. I felt like I was achieving my aim, not that the just called me a slim little blonde slut, but that they described me as the hottest girl in the bar.

One guy even described me as a girl who could make you rock hard with just a look and a kiss, and then drain you dry so you thought you would never cum again. Jill had no idea of course.

She didn't dream that almost every night she was gone I was flirting in some bar, and usually swallowing a big load of cum. I doubt she had imagined what I had become when she decided to win that contest.

She would have been more shocked if she knew that I had half decided I wouldn't ever change back to that grungy IT consultant she had married. Each week she still reassured me that this was only for the contest. I hadn't figured out how to tell her I was probably staying this way, win or lose.

I also figured it wouldn't hurt to keep my rear passage used to accepting penetration, if I decided to go that final step. I had used the plugs of course as part of my initial training. But now I made sure that I had the biggest plug in my ass all day long while working, not just in the morning anymore.

I loved that the jeweled end of that massive plug matched one of my favorite pair of uber-expensive red high heels. And the feeling as my ass was full the entire day was special. I learned I needed to work exercises with my ass muscles though, or I would have a permanent ass gape, not pretty!

Going all the Way.

The butt plug was pretty special. I not only started to love as it passed my tight ring, but how it popped into place. I could feel it very step I took, but the extent of the pleasurable fullness and naughtiness of it all was unexpected.

After the daily penetration sessions and wearing my plug, I knew I could do this. A few weeks after I finished my training, I decided I had to see if the oral adventures were the end of the line. I wanted to try to pick up a man, not hide what I was, and have him take my anal virginity.

I had decided I was ready to cross that line, and knew just how to do it. I had the guy and the place all picked out.

On my big target Thursday night, I picked the same bar I had grown to like, the one with all the private upstairs rooms that never seemed to be in use in the evenings. I figured it might be the perfect setting for a quick exploratory fuck.

I dressed in a retro white silk dress. It was sleeveless and simply tied behind my neck, linking the two narrow bands that partly covered my boobs. The silk was so narrow that it that exposed some side boob. The straps started at my naval, so I had quite a bit of skin showing in front. But in the rear, the dress was so long that I exposed a noticeable amount of ass cleavage.

Longer than many of my skirts or dresses, the new dress didn't even reach my knees. I paired it with some simple high white heels. I topped it off with another of Jill's wigs, this one a long 70s style platinum blonde wig. It was my color, but probably nearly a foot more hair.

I had texted my first oral conquest, Steve, and asked him to meet me there. He was immediately agreeable. I knew he was expecting to go further than the hot blowjob he had gotten upstairs last time, and I had no intention of disappointing him.

I told him though that I had to share some secrets that night, and maybe we could take things further. I got some question marks as a text back from him, but we agreed to meet.

He loved my outfit and again we were again quickly extremely physical with each other. Steve had seemed very open to alternative lifestyles in my talk the first night. So, after we had drunk a few martinis, and necked in a dark corner, I decided to see how open he was.

I knew this could go all the way from immediate acceptance to a drink in my face. I was pretty hopeful but knew I could have been reading Steve totally wrong. But I was by now massaging his dick through his pants, he really liked that bit of attention. This was probably my best shot.

So, it was now or never I decided. I told Steve that I was a different kind of girl. He was puzzled and just stared back at me. I told him I was a girl with a little bit extra, that I hadn't been born looking this way. It was funny, it was if a light went off suddenly,

"No fucking way Jane, if you aren't all girl than I'm losing my mind. You weren't born this way?"

The cool part is he didn't jump or look horrified. But then again, it may have helped that I was still working my stick shift skills on his rod. I shook my head back and forth,

"this is all a recent transformation, will you help me take it further, like I texted you?"

He smiled and I took that as a positive answer. I went on,

"I can show you all of me upstairs, but I really want you to do is to make love to me, to be my first."

Steve didn't move away at all, but told me that he had never done it with a gurl, but had actually always wanted to do that, in fact it was one of his fantasies.

We started kissing again, getting much more spirited. But Steve told me he wouldn't do it in some meeting room, that wasn't right for my first time. He told me he had a much better idea. His condo was only three blocks away. I grabbed his hand, gave him a kiss and nodded up and down.

We left the bar and shortly were on the couch in his small studio. I got more and more aroused, and Steve loved it when I sucked his dick for about five minutes, taking to the point of nearly cumming at least twice. I backed off, I had better use for that dick than giving me another liquid snack.

Steve got some KY and a condom from the side table and started rubbing it around my hole and then inside, ending up with two fingers fucking my ass. He told me I was doing really well, and I told him I had been practicing with toys for weeks.

I leaned over, to make it easier, and threw my leg up high. Then with almost with no pain, he began to push his cock up my ass. It popped inside right away, after all he was smaller than my mid-size training vibrator.

The only change to my look is my long wig fell to the ground and Steve pounded into me with my shorter, curlier blonde hair. Wow, finally taking the big step. It felt smaller than the massive dildo I had bought, but any cock would.

Based on all my practice he not only slid right in, past my anal muscle ring, but I was able to immediately get into a rhythm with Steve. He was thrusting deep inside of me, and we were making a very wet squishy sound as we had really used a lot of lube.

In short order we both settled into a rhythm. Steve was pounding my ass with long hard strokes, and I was playing around with squeezing my ass muscles. He moaned and groaned, clearly loving that.

I was a little surprised, it was so much better with a real cock than all the prep work with my toys. My smaller dick got hard, but I didn't reach down to play, afraid I would spray everywhere.

As I was panting away, I started to see why people enjoyed this. The sex was fun, and intimate, and it didn't hurt that Steve was hitting my P-spot on every stroke. In this position, kind of sideways, I was able to look up at him. It was nice that he seemed to be as into the whole anal sex as I was.

After about five minutes he seemed to swell, my rhythmic squeezing was probably a big part of the reason for his imminent orgasm. Suddenly he tensed up, moaned, and pulsed.

I could feel like what seemed like a pint of cum deep in my ass. We kissed and cuddled as he softened, lying together on the couch. As he popped out, we cleaned up and relaxed in the glow of my lost anal virginity.

One thing I knew, this would not be a onetime deal. I now knew that not only could I fuck as a gurl, I really liked it too. I thanked him for being my first, and called it a night.