Not Willing to Go Back Ch. 03

As I got ready to leave Steve looked at me,

"since you seemed to like this, what about a repeat soon, with some extra friends of mine?"

I had to consider that. I thought for about three seconds and looked into his eyes,

"Baby I'd love that, you sure they'd be ok with a Trans girl?"

Steve laughed and said once they fucked my hot ass, they might only want TGurls.

I seal the deal by kissing him. I nodded up and down and smiled saying I would like to have two or three cocks to make me feel full. As I got home, I really started to wonder, how would I explain all this to Jill.

She had no idea I had been sucking and now fucking during every one of her business trips. She must have been a little worried I would go through with this all of this deception and work. Instead I was loving all the changes, probably a lot more than she ever imagined.

I knew, even for me, the non-he-man, it was mind-blowing how much I loved being Jane. I certainly already knew I was liking the new me a lot better than boring old Jay.

I liked the whole experience of being a hot girl, the attention I got, but also how it felt to walk around in lingerie and sexy outfits. Hard as it was to believe that even included the hours getting my look right each day, the baths, and lotions, the plucking my eyebrows and applying very complicated makeup arrangements.

I still loved working out really hard almost every day. That with the daily dose of hormones was keeping me really thin, and allowing all my new curves to stand out. Now what would I say to Jill when she got back, would it be obvious how totally I had embraced being Jane?

But when she came home after her next trip, we had a great time, but not like I expected. Jill full on embraced me in my feminine persona on Saturday night. We stayed in and had a night just for ourselves.

Jill had me pull out all the stops, as our girls' night in was a couple of classic Hollywood glam movies. She encouraged me to go with a very 1940s look, including the makeup and having my hair up, using lots of gel and spray.

She matched me, with a retro dress and bold red lips. She also had gotten into changes I noticed, with a cute set of highlights, so her auburn hair now had blonde highlights. It was upswept too, like some old time star.

When she leaned over my shoulder caressing my right breast and nipple while her left hand was pulling on my cock, I was in heaven. Not sure if one or both of us was feeling guilty, but she sucked me to hardness over and over as we fucked each other raw.

Her nipples were red and swollen for hours and she returned the favor on my, still very sensitive breasts. I don't know what had gotten more attention, my tits or dick. Definitely not something you'd see in an old-time Hollywood film, but we liked it!

She also had fun, telling me I was all gurl, and taking her finger, soaked with her own juice and pushing it in and out of my ass. She was surprised when I was able to clench then ripple my ass muscles around her digit.

Little did she really know why I was so good at that. She told me we would have to explore that hole later, I smiled and told her,

"baby all my holes are yours, I have talents you don't even know about."

Jill thought it was a great joke, little did she know it was my first attempt to discuss my adventures. We repeated our fun on Sunday morning, then on Sunday evening, just not taking all the trouble to go all 40s retro glam.

It was kind of funny that both of us were sitting around in our silk robes drinking coffee, like two very cute girlfriends, when we had just finished a great wakeup sixty-nine session. That night Jill went further than using her fingers, moving up to her mid-sized vibrator.

I made a big act over being concerned it would fit, but of course it slid right in and I enjoyed her taking control of my ass. I know She had no idea of the size of my training vibrators and plugs, nor that I had taken a real cock up my ass only a couple of days ago.

A Parallel life; Developing Skills and Growing a Wardrobe

For the rest of the third month after we began this adventure, and into the fourth month, we had a pretty regular pattern. Jill was traveling more and more for work, which I guess was a sign she was going to get promoted soon, and I continued to work hard at my new persona and consultant work.

Now I was in a pretty self-absorbed daily routine. After Jill left for work, I changed out of my sweats, took a break from work and took my daily scented hot bath. After that the full body moisturizer and makeup, hair and hot outfit were second nature to me by now.

The hormone mix had done its job, I was smooth and my pores seemed much less obvious. I was aroused it turned out, no matter what makeup style I chose.

I also kept my weekly appointments at the salon, having my hair trimmed and nails worked on. The owner pulled me aside at one point and told me I was among the hottest of their clients, and she was still amazed how feminine I had become.

My arched pencil thin brows and my thick long lashes were the farthest thing from masculine, I had to admit. But of course, the hairdo that didn't need any extensions and went more than halfway down my back, as well as the perfectly manicured hands, with those one inch nails didn't hurt my look at all.

I was feeling ready for anything now. Steve and I had fucked pretty regularly, but I decided I wanted to see how slutty I really was. Late in the third month, as Jill was on the road, I accepted Steve's invitation to try a larger group.

He and a friend met me at the bar and bought me drinks. We were getting really frisky when Steve steered us the three blocks to his condo. The next two hours were a blast.

The guys loved it when I peeled off my top and skirt to reveal a patent leather piece of lingerie that left both boobs exposed. Down below it just had two straps to leave my cock open to the air and wandering hands. Of course, they both loved my six inch heels.

I traded back and forth sucking dicks, on my knees in front of the duo. I then spent the last hour rotating back and forth between the guys, one deep in my throat and the other deep in my ass. In a nice touch, I kept my heels on, and they did give me more leverage.

I liked being on top that night, as I could play with myself as they pushed up into my rear. All in all, I had provided some of the answers I was seeking. I was for sure at least bi, and loved being the center of a gang bang. I wasn't sure how big a group I could take but I loved it. I stilled loved to take Jill to bed, but having a dick in my mouth and another up my ass was pretty fine too.

Steve introduced me to some of the many folks he knew in the area, some were just regular bar and restaurant owners, but some were a little sketchier. A few of them even reminded me of characters from the Sopranos.

When they heard I was an IT consultant they were all shocked, how could a blonde who looked like me know anything about hacking a computer network. But a five-minute discussion pretty much convinced them I had a brain between my pierced ears.

Two or three "businessmen" asked me to take a look at their operations. I was a little scared to dig into the systems, I liked my heels and boots not Mafiosi cement shoes, so swore I only worked with total discretion.

Once I identified some critical actions to take to protect them against cyber threats, and of course various law enforcement efforts, they were sold on my talents as a cyber gal. In fact, they didn't want the tech support to be a one-time effort. That surprised me.

I was suddenly on retainer for two different "business" groups, for very lucrative monthly fees. All in cash of course. I had to configure their networks and set up all sorts of systems to detect law enforcement monitoring and intrusions, but I could do that in my sleep. And the extra untraceable cash helped all the new things Jane wanted...a lot.

This cash flow, totally unknown to Jill, allowed me to expand my purchases of all the fun stuff, racy or even slutty lingerie, shoes and boots that men would drool over, and of course tight sexy outfits.

I also bought some rather expensive wigs, so I could go short and sassy blonde or a wild redhead. I stored everything in a spare bedroom in the townhouse. Jill hadn't gone in there in years, I figured she would never know.

In only a couple of months I had a really hot wardrobe, just none of it suitable for a traditional office, and of course none of it usable as Jay, all of it was only suited for Jane. But I was starting to like Jane a lot more than I remembered liking Jay.

I could have fun with men, women and both together as Jane, not something I think I could have done as Jay. I now had to admit I liked to fuck and be fucked. And to be honest, the clothes I wore now were so much nicer, and sexier.

At one point I started to wonder, why was I shopping for all these items when after we won the prize and took our trip, I was going to have the breasts removed and go back to Jay? I was having trouble understanding and justifying the weekly shopping trips, paid for by my cash-only consulting business.

Other than the fact I loved how the clothes looked and felt, there was no rational basis for the growing wardrobe in that spare bedroom. I mean I knew that reverting to Jay, before our trip to NYC had been the plan all along.

I was working this hard only to win the prize and trip, right? Maybe I was starting to rethink that too? In fact, I was realizing I really wasn't going to willingly change back to Jay. It was good that Jill had fun with Jane, because she was probably permanent.

My shopping trips were generally when Jill traveled. I was still a little self-conscious about vamping it up and buying super sexy clothing with her around. Besides, how would I explain all the money I was using to buy all the clothing, lingerie and shoes?

So, I would take a break during my working time to hit some of my favorite boutiques. I wasn't going to find my kind of stuff at Macy's or Target after all! Instead I tended to favor the smaller, trendier boutiques, and I never got even a second glance from any of the sales help.

And I had to admit, with my new boobs, my tanned and fit body, I could make a lot of outfits look great. I just knew I looked super good in my new brown leather skinny jeans, especially when they were stuffed inside my thigh-high black leather boots, definitely a fuckable look. It was a sexy look, even though I was showing no skin at all.

But skin was sexy I knew, and had proven its effect in multiple trips to various bars. So, most of my outfits may have been expensive, but didn't cover a whole lot of my short, hot body. I literally got aroused just getting dressed and felt a surge of power, not fear at the whistles and comment from guys.

With that knowledge, it was only natural that I liked strutting around in my skin tight mini-skirts, along with other boots, especially my new "classy" favorites, knee high black suede. I already had a lot of choices filling that spare room. I had made that much from my consulting gigs.

I realized as l looked through my closet after a while that there was no way the old me would have worn the equivalent of this stuff in the men's section. But I of course had always loved it when Jill looked this way, so maybe that was something.

I was basically realizing that Jane was not just Jay, shaved with bleached hair and woman's clothes. Jane was much more about the sexy looks, the teasing, and getting fucked whenever I wanted it, however I wanted it.

The way I walked, got into men and women's personal space, the way I touched and caressed in almost every encounter, was not what Jay would ever have done. Jane was wanton and forward, and thoroughly sexual creature. She didn't stroll, she seemed to stalk around.

But even though I often seemed to end up on my knees with my mouth stretched around a hard cock, or on all fours spreading my cheeks, I was in charge of deciding if that was going to happen. As Jane I controlled my sex life, even though the guys I was seducing didn't seem to realize that.

I also had to admit, that I liked how I looked and was treated a lot more as Jane than as Jay. Now if I walked across a street or across a bar, every heterosexual male and quite a few hot girls were undressing me with their eyes.

They all seemed to want me, and not in a platonic way either. To be honest that was a big part of why I liked the whole Jane persona. As Jane I didn't want them to be with me in a platonic manner either.

My secret vice, beyond my sex toys, expensive makeup and wigs was my feet. I specifically wanted to have designer boots or heels on my feet every day. Also, nothing demure; they had to be high enough to make my five and a half feet look tall and distracting, so never less than five inches.

This was a clothing choice that took some training and practice, but from Jill when she came home to every guy whose eyes snapped to my ass as I walked past, it clearly was pushing buttons with everyone. I had quickly realized that though my hips and ass weren't Kardashian-like, when I had on my heels, I picked up a very sexy sway that seemed to demand attention.

I soon had a row of at least ten pairs of sexy stiletto heels. The only thing they had in common was the fact that every one of them had really high heels. I had black ones, red ones, white ones, and even purple ones. Some were classic spike heels, some looked like stripper shoes. And walking wasn't a challenge for me either.

I had gotten quite used to the balance issues, and my runner's legs both looked good and were flexible enough so my tendons didn't kill me. It certainly made it easier that I wore heels at least nine hours a day. Besides the sound of the heels on hard floors made everyone notice and still got me all hot and bothered.

But if I loved my sexy shoes, I adored my boots. I reveled in all the choices, but generally liked black most of all. I had realized that boots set a certain tone for the whole outfit and a lot of guys were simply mesmerized by a chick in hot leather or latex boots.

And if knee high boots drew attention, my thigh high black boots made guys stare and almost drool. Their eyes were drawn to the shape of my legs, but also to the small gap between the top of the boots and the bottoms of my dresses or skirts.

Whether that gap was tanned skin or some hot fishnet stockings, it always got more attention than my legs when I wore my running shoes. To be honest, I kind of got into that sexual power trip. A girl in those type of boot just radiated that she was in charge tonight.

In fact, I learned if I placed my long boots over a guy's legs in a bar, or rubbed them against him while standing together, his interest level skyrocketed. That seemed to also show in the tent that almost always instantly appeared in his pants. I may not have admitted it when I was a traditional guy, but I now knew how simple men were in their drives and focus areas.

I also got the wigs I felt I needed. If I didn't want to always take the time to work on my hair, or if I was bored with the long blonde hair look, curly or straight, I donned a wig. It was funny how a new color and style of hair allowed me to adopt a whole different attitude and vibe.

The blonde short haired sassy wig was one of my favorites. It showed off my long neck and he lines of my shoulders, and allowed me to be much more playful instead of just bimbo-ish. And I think I rocked that look too. When I combined it with some hot red lingerie, it oozed sex, especially with my dick poking straight out below the garter belt.

Steve certainly felt so, when he came in and saw me kneeling on his bed, I got everything that I had wanted when I used the key, he gave me, to let myself in. I knew I was being forward not calling first and then setting myself up on his bed, but my instincts were good.

First, I enjoyed some great worship of my breasts and nipples, it still did feel so good when my nipples were sucked on, even though surgery had been quite a while ago. But I wasn't going to be selfish that night. As Steve must have known, I was going to give as well as receive pleasure.

I pulled him away from my tits so I could begin to lick and suck his dick and balls. I was in the mood and soon had Steve very hard and begging me to let him cum. I didn't want to swallow I told him. Instead I smiled and told him I wanted his dick deep inside me. So, we finished with Steve buried all the way in my ass and depositing a nice big load of cum up there.

I wasn't sure what Jill would think of this new side of me, but it was rapidly becoming a part of me, as much as fucking and sucking with her had been for years. This Jane character was just not the flip side of Jill, she was a feminine sexual aggressor in so many new ways.

I still loved to pound my cock into Jill, but taking hold of my undiscovered feminine side was really hot too. Having a guy's weight on me as he pushed his dick inside me, normally after I had sucked him hard and often drained him once, was an unexpected pleasure.

And oddly enough, cuddling up against my guy after he popped out of me was relaxing and a final scene I grew to look forward to. I wasn't sure what Jill would say, but this Jane person was me now too.

Part IV Coming Soon...Jane really pushes her limits, but then Jill and Jane come clean with each other.