Not Willing to Go Back Ch. 02

The hormones had also really started to help me. They softened and smoothed out my skin, and had given me a bit more of a curvy ass. I fit in the new skin-tight dress like it was made for me. I grabbed a small purse, spritzed on a heavy dose of perfume, and drove down to a local bar. It was well known for dance music, a great happy hour, and a bit notorious for being a spot to hookup for the night.

The bar was what I needed, loud, crowded and with a lot of energy. I also wasn't ever lonely there. The guys were all over me at the bar, and on the dance floor, each competing to get my attention. They were all trying different techniques, and I was getting distracted. So, I picked out one hot guy to try out my developing bar slut techniques.

I wanted to see how aroused I could get him, and what he would say to me and do for me. I was just a little worried, would he know? But in my dancing the week before, no one seemed to suspect a thing, so I went for it.

Joe, my target, didn't suspect a thing it turned out. He immediately had his hands all over my delicate smaller hands, with their bright red polish. Then he moved his hands up on my arms to pull me very close. You couldn't have squeezed between us even if you tried. In just a drink or two one hand had moved from caressing my bare back to resting right on my ass. Joe seemingly couldn't resist rubbing and squeezing my cheeks.

To say the least, he seemed to be quite smitten. He was just staring down into my eyes the whole time, telling me I was the hottest girl in the place, and he was going to be dreaming of me. Joe clearly intended to try to get me in bed.

The problem was I wasn't, I thought, even close to ready for that big step. But it reassured me that this big guy clearly thought I was a young blonde chick, and was doing his best to get me to go home with him.

So, after a couple of drinks and some long drawn out kisses, I apologized and told him I had to get up for work early. We had been getting pretty heated, our tongues seemed to be in each other's mouth more than our own. I was even so bold as to reach between us to his crotch.

He had what felt like a big hard cock, and he jumped and groaned when I began to rub and squeeze it. Just to see how much I could get away with he started to stroke his dick pretty aggressively. He finally grabbed my delicate hand and told me if I didn't stop, he'd cum in his pants right in the bar.

Mission accomplished, Joe was totally aroused, and willing to do about anything for me. While I was stroking his cock, he did sneak in a few covert gropes of my boobs. That actually felt more than a little nice. I stopped him when his hand tried to get under my dress to move north though. Even in the gaff I knew my groin didn't feel like a girl's smooth pussy.

I did have Joe help me out though with one last task. I couldn't resist reaching out to Jill. I had to untangle him from our tight embrace, and make sure my neck wasn't covered in hickeys, but I did manage to pull away.

Then, I had him snap a pic on my phone of me, looking very relaxed, glass of white wine in hand. As I looked at the pic on my phone, I did look hot and a bit flushed. I knew it was from my session in the dark corner with all the groping and long kisses. I texted it to Jill, asking her if our fathers would even recognize me now.

She replied in a few minutes w/several laugh emojis, then the comment,

"hell no, but they probably would buy you a drink and try to get inside your panties."

Then she finished text with a series of broken hearts and smiley faces.

I knew she was likely surprised and maybe worried by how I had grown comfortable in this new lifestyle, but oh well. She didn't even ask what I was doing in a bar dolled up on a Wednesday night, looking like I'd had a few drinks and maybe looking a bit ready to fuck.

And frankly, I was in fact, very horny from Joe's kisses and rubbing my boobs and ass. I'm not sure how I would have answered that unasked question about why I was in a bar dressed to kill. It didn't fell wrong though, instead I was more and more having fun as Jane.

I got home and I was no less aroused than at the bar. I couldn't resist pulling down my thong and then my gaff. My hard cock popped free, sticking out below my dress that I had pushed up above my waist. I looked super-hot I had to say. So, I pulled off that tight dress, it was too expensive to ruin.

Framed by my thigh highs I presented quite the picture as I laid on our bed, looking across at our wall mirror while I played with my cock. For the first time I not only lubed up a finger and my ass, but was able to cum as I stroked my dick with my right hand and my fucked my own ass with my left index finger. Wow, it felt so good I knew it would not be the last time for exploring my tight ass.

Sliding Down that Slippery Slope

I was fine being alone during the days that week, I had a huge amount work to do. It was actually normal for work, but I had an extra incentive this week. If I could get this one current difficult work task done, it was going to be financially great for me. Amazingly, on Thursday I had a breakthrough and hit all our performance objectives on that big money project.

About six I was totally done. I knew I was now qualified for a big bonus for being done a week early. I knew this was not what my boss was expecting, but he now owed me an extra 10K. I was also suddenly considering something that the old Jay wouldn't never have dreamed of doing.

Even though I had been out Wednesday night, I was ready to hit the bars again. I convinced myself that I really deserved a bit of a celebration and to let my hair down, even more than last night. I wanted to go get a drink to unwind get some dinner, and maybe take my bar slut persona a little further.

All I knew was I was not going to be staring at our four walls for another night, alone. This Jane persona was really not like quiet Jay. I also was starting to consider what were next steps I was willing to take as Jane. Clearly, I was really liking not just all the dressing up that my deceit entailed, I had weirdly really liked all the kissing and groping last night with Joe. Maybe I wasn't as straight as I imagined.

So, just like last night, I spent the next two hours getting ready from my head to my toes. I showered up and shaved for the second time that day, very closely. I went with an evening approach to makeup, with strong colors and a very defined treatment for my lips. In fact, it was even heavier and darker than the prior night.

I also tried something new and didn't go with my normally blonde curly look. Instead I slicked my blonde hair back, tucking it behind my ears and letting it hang straight down my back. The slicked back blonde hair really showed off my face and my big silver hoop earrings.

I realized that I had the facial structure to really look good this way, and oddly, my face, with the long hair and well-done makeup didn't look at all masculine or even androgynous...just all hot chick. More and more I was feeling very natural as Jane, not worried at all about being exposed as Jay.

Then I went an extra step. I put on a very tight new fancy gaff that hid my dick much better than my other gaffs. It was also sculpted so on the outside it looked like a shaved pussy. I had to have this super tight gaff with my outfit I knew.

This gaff had a sleeve you lubed up and then your dick slid inside. The whole thing was skin tight, with that fake pussy slit that I could pee through, a pretty functional piece of deception. However, I didn't plan on testing the marketing claim that it allowed full on intercourse.

For my outfit, I pulled on a black lacy thong and set of fishnet thigh-highs. I wanted to keep it simple. Then I rifled through Jill's party clothes in her closet. I pulled out one of Jill's racier dresses, a favorite of mine. It was super short and super sexy with my bright red lips, and very high six inch heels.

The dress was not at all office wear. It was a low-cut shiny leather little black dress. But the best part was the series of very large rectangular holes cut down each side from just below my boobs to the bottom the dress, which was only about ten inches below my restrained dick.

The dress was very hard to pull up, it was that tight. But it made my braless tits and ass look great. And of course, the cutaways on the side showed off not just my legs but most of my torso, almost up to my boobs. They had to be at least a foot wide and six inches tall, I was exposing a lot of skin.

The entire outfit screamed hot slutty chick, ready for sex. In fact, as I strutted over to look in the mirror, I was amazed. I was now not just putting the whole outfit together, I was prancing around on heels that were ultra-high, as if I was born in them. I decided to not go back to the local meat market, but to go bigger.

I went to the next town over, it was a bit bigger than our little burg, and likely to have more going on. Even better, no one knew Jane there, so no danger of Jill hearing about my escapades. I settled on a new bar for me; it had a reputation for a great happy hour, and a total pick-up spot.

I was still amazed, another new bar and no one batted an eye, or seemed to suspect what I had tucked away into my new, fancier gaff. Then again, the outfit was totally rocking it.

Even before I got to the door several groups of guys turned to watch my ass as I walked up to the door and a guy literally tried to hit on me as he held the door for me. I also loved the sound my heels made on the walk up to the bar entrance. The whole place was already rocking, and a wave of sound hit me as I blew a kiss at the guy at the door and headed inside.

In fact, as I made my way to the bar, at least half the guys seemed to be undressing me with their eyes. There were some very open dirty looks from their dates, and at least one slap. Wow, this was really the same guy who two months ago had thought wearing a collared shirt with jeans was dressy? The one who had been a grungy IT hacker two months ago?

I found that I wasn't going to be lonely for any part of the evening. Tonight, I had all sorts of options about who was going to spend time with me. What shocked me further, but I wasn't ready to pursue yet, was the hot stacked redhead who hit on me in the ladies' room, telling me,

"baby after a night with me you'll never want to go back to those dicks."

I grinned at her, gave her a little kiss, and told her,

"maybe next time. I feel like hard dick tonight."

The really nice part, with a happy hour crowd and my looks, is I again realized I didn't have to worry about paying for a drink. Though there was a cost. I had my ass rubbed and squeezed and at least three guys gave me hot kisses when I accepted their free drinks. Several unidentified hands cupped my cheeks as I tried to pass them on the way to the ladies' room.

All in all, my night out, that was my reward for finishing my project early and getting that bonus, was going very well from the bar slut perspective. I had my choice of who I spent time with too, there was a steady stream of guys who just had to try their pickup lines out on me.

By about ten I was feeling no pain, figuring I had pushed my development about as far as was smart in one night. An Uber ride home night tonight I realized was mandatory. But I had an issue. I was really getting friendly with this tall, fit guy who was maybe five years older than me.

He and I were very close to each other, and a couple of times I felt his hard dick, either rubbing between my cheeks or against my fingers. I wasn't sure how I was going to get free and even get to the Uber I needed to order. Besides, although I needed to work in the morning, I didn't really want to leave.

But it was partly my fault. I had to admit, I had made sure as my hand passed near his crotch, at the bar or dancing, I rubbed and stroked his dick through his pants. It was a nice big cock I thought to myself. I was wondering what it would taste like or how something so big would ever fit in my ass.

He wasn't too timid either, cupping my cheeks on the dance floor and rubbing my boobs from the side on a regular basis. I had enjoyed bending over and pushing his dick right between my cheeks on the dance floor too. Turns out my ass, strong from all the running, was perfect for squeezing that dick.

We had rapidly moved from discussing music, and the latest hit movies to very racy, suggestive back and forth. He was making all sorts of comments on my boobs and how he wanted me, and I was talking about how his dicked seemed happy to see me.

But most importantly, what had gotten into me, why was I so horny with a guy? I was totally hetero, or was I? This was going a little far, little did I know, I was already sliding down a very steep slope. I blamed the three strong martinis, and no food since breakfast, it had been a long time ago.

Steve, the tall guy, was just as heated as I was. He and I were kissing now almost continually, and in our dark corner he was massaging my very sensitive breasts and nipples. I had barely stopped him from pushing the dress up and rubbing me through my thong. We were close to seeing how good that expensive gaff was at hiding my hard cock.

I was in a little bit of a panic. How was I going to keep Steve from trying to take me home? Then I figured it out. I told him,

"baby I'm so hot for you, but his is the wrong time of the month. I'm so sorry."

It was all I could think of, as I didn't even know if my gaff would allow sex, and really didn't know how I would manage anal sex. My finger was the biggest thing I had ever had up my ass. I was hoping this would allow a graceful retreat to the Uber I was about to call. Oddly enough, I wasn't too sure I was opposed to Steve slamming that hard dick into me though.

Steve sighed and pouted, and then asked me if I was open to taking care of him other ways. I thought for a sec and after the kissing last night and tonight, I realized I was really actually ready to move further in my journey. So, I nodded, telling him I would love to swallow his cum.

This would be a first, but Steve didn't know that. I was going to see how another guy's cum tasted. From all our playing around I was pretty sure Steve wouldn't last too long either. I didn't really want to go to his place, and no way I was taking him back to our condo. But Steve smiled and told me he had this.

He knew the bar and took me upstairs where they had a series of private rooms. He checked the locks along the hall and found one open. It was a smaller room, perfect for private functions. Steve sat down on one of the chairs and pulled me over to stand in front of him. The room was quiet, with subdued lighting.

I leaned down and started rubbing his dick through his pants, while we kissed some more and he ran his hands up and down my legs, finally reaching up to grab my ass. It was nice to have him lower than me. Even with my five-inch heels I had to look up to kiss Steve when he was standing.

Now I was leaning down to kiss him as I stroked that hidden big dick. I was a little scared he would cum from my hand job, but also a little nervous about facing his dick. Finally, I took a deep breath, paused in my stroking motion through his pants, and unzipped him.

I fished his very hard cock out into the open. It was hot and hard already, big and thick. Steve's dick was just a little bit longer than my cock, but much thicker. Wow I was really was moving into uncharted territory, bet Steve didn't know that!

Steve's dick had a nice shape and was very warm and even throbbing a bit as I fisted him. I figured it was time to break my oral cherry. I dropped to my knees on the carpet and I paused with my tongue just touching his tip. I did notice, allaying one of my fears, that his dick smelled really nice up close.

I thought, wow, didn't see this coming this morning when I woke up. It was now or never; would I lose my nerve?

The answer was no I wouldn't. I was actually really aroused and was frantically trying to think of what to do next. So, I decided to just do what Jill did to me, I loved her blowjobs. That did the trick, based on Steve's moans and groans. For my first attempt at oral sex, I was surprised at how quickly he reacted.

I began by tonguing and sucking the head of his cock, swirling my tongue around him, while I continued to jerk him off with my hand. Then I began licking up and down the length of his throbbing shaft, pausing to suck on his shaft over and over.

Oddly I wasn't disgusted or revolted, instead it just felt very natural. Steve's hands were buried in my long blonde hair, and he never stopped moaning and encouraging me,

"oh Jane, suck harder baby, that is soooo good." was a typical comment.

I spent the next five minutes with variations of Jill's best tricks. I was generally licking and sucking, moving up and down his shaft, over and over. But I was also sucking really hard on the head of his dick occasionally. While I was doing that, I was rubbing his balls, trying to repeat what I loved Jill to do.

I wanted to see if I could deep-throat him and got about half his dick down, but it turns out the gag reflex is real. That would take some real training I realized. But even getting only about half his cock in my mouth got a loud reaction from my partner.

Steve had been moaning more and more, he was close. I felt him start to throb, he grabbed my hair and told me in a hurried voice that he was cumming. I clamped down with a really tight lip lock on his shaft, I freaked out as I realized I could not stain Jill's dress. That I could not explain!

And so, I got my first load of cum in my mouth, and there was a lot. It felt like a half pint, even though I knew it was only a few tablespoons worth. It was a little saltier than mine, but not too different. I swirled it around my mouth, savoring the taste and texture and realized I had to spit or swallow.

It hit me that I had taken another giant next step in becoming Jane not Jay.

I decided to do what a real slut in a bar would do. So, I swallowed it all, licking my lips to make sure there was no mess. While doing this I was staring up into his eyes, through my thick fake lashes. My new friend grinned down at me, and admitted he was done for the night. I as looked up at him, hard dick still in my face, I knew he had no idea I didn't have a pussy under that tight leather dress.

Then I really went crazy. I pulled my smart phone out and had Steve take several pics of my sexy face licking and sucking his cock as it softened, clearly cleaning it up after finishing sucking him off. I wasn't sure if I was ever showing Jill those pics, but wanted a record of my progress, or so I rationalized it.

Steve did kiss me with no hesitation and played with my boobs till I knew I had to stop or I would go a lot further on my first night than just a blow job. We said our goodbyes soon after, though we did text each other our numbers as I waited for my Uber to show up in front of the club.

I was shocked but also very turned on, I could feel inside my gaff that it was soaked with my own cum. I had not just been ok with it; I had been so turned on I came without even touching myself. What would I tell Jill, or would I tell her? I had not only sucked a guy I barely knew in a bar; I was so turned on I came too.

Part III Coming Soon...Jane hits her stride and expands her parallel, hidden life.