Young Times

By sissi lesli

Published on Oct 28, 2013

Transgender

Young Times Part VII

I still have plenty of time before I have to be at work, so I decide to swing by my apartment and clean up. Between last night's partying and this mornings troll through the ABS, I'm looking and smelling somewhat `used' and in need of a little freshen up. All the groveling in the booths had left me with the usual cum/urine/disinfectant smell, and if I can smell it I'm sure everyone I come in contact with can too.

So, I drive down Williamson Road, past the Holiday Inn where I work, and on to my apartment on Elm Avenue. It's an older building, in an old part of Roanoke's faded past that hasn't been revitalized like so many of the downtown buildings have. Not that I'm complaining, it's run down condition serves as de facto rent control, and keeps it in my meager price range.

My apartment is on the second floor, end unit with a view of the city to the west from my living room/bedroom window. Not much of a view, given that the city in that direction is also suffering from lack of money and attention. But, again, it's in my price range and it's home.

I strip in the bathroom while the shower is warming up and fight the urge to take a long, relaxing, bubble bath in favor of a quickie shower and shampoo. My long blonde hair dries naturally, so I'm standing in front of the mirror working on my face with a towel wrapped around me when my bowels begin their early morning conversation with me. I don't really remember what I had for dinner last night, probably pizza, but after at least three and possibly four servings of semen in the past twelve hours, on top of the beer, my stomach has processed enough fluid to precipitate a movement.

And that comes quickly, followed by a pee before I clean up. Next I go through my normal morning ritual of an enema and anal douche. Now I feel clean and girly again!

After applying skin moisturizer to my body I pull on a fresh thong and the bra from last night. I have work clothes in my locker at the motel, so this morning I put on my go to work clothes' which consist of sneakers without socks, tight fitting jeans, and an equally too tight open neck pink tee with a girl rules' across the front. I pull my still damp hair into a pony tail, hang a pair of large loop plastic ear rings through my pierced lobes, and slip on the rest of my `bling' before checking my image in the bathroom mirror. Finding myself passable, I grab my shoulder bag and head out the door.

I've had my job in housekeeping at the Holiday Inn for seven years now. It's not rocket science, and there's no career path' to a higher paying job in it, but it pays quiet a bit more than minimum wage, provides minimum benefits and a somewhat flexible work schedule. All in all, just what I need to cover rent, transportation, spending money and enough left over to lead a more or less comfortable life. The key to living a comfortable life, I've found, lies in the definition of comfortable'. Sure, I could make more money as a prostitute, in fact I've made lots more money hooking, but the risk of harm or arrest isn't worth it in my mind.

Or I could live off a boy friend or lover. I've done a bit of that from time to time as well, but the paranoia and distrust and restrictions are too much of a hassle when it comes right down to it. Boy friends can be nice, don't get me wrong, and I do have sisters who have `married' a man, promising to be faithful and the whole nine yards, but that kind of long term commitment isn't for me. If I want to live with a man, I'll do it, but always with an escape route in case I, or he, tires of the arrangement.

No, I don't mind my job, don't mind working. In addition to rent and car and spending money, it also keeps me in co pay money for my hormones, and that is vital to life for me. I gave up the thought of GRS years ago, but have been on hormones so long I can't imagine life without them. Not true, I mean I can't imagine me without them.

But I do remember the days before hormones...

Young Times (the between years) Part VII

Over the next few weeks I would come to learn about living life as a girl. And I would learn the tricks of the trade as a prostitute. And, probably more importantly, would come to the realization that, while I could have never, ever, imagined this happening to me, it was a role completely in harmony with my view of myself. In other words, I came to not only accept, but truly believe (understanding would come later, with the help of a shrink) that I was meant to be a girl. While the mannerisms and appearance came quickly, the belief in my self built slowly over the course of my time in Roanoke. And beyond.

My `routine' was now dictated by the hours I worked the street, usually nine PM til one or two AM, depending on traffic. Weekdays were slow, with more johns cruising on Friday and Saturday nights. If the traffic was good, I could be on the street as late as four or five AM. But, at no time, would I be on the street during daylight. I didn't know it at the time, but Bill was paranoid about my being picked up by the police and traced to him. Since I was underage, he was taking a big risk.

Bigger than we knew, because sometime around the end of my first week on the street, people were looking for me. Even though Clarence hadn't given up any information about me, my hometown police were sharing enough information with the WVA police to cause them to believe that Clarence may have had a hand in my disappearance. They shared that with the Roanoke police and requested help.

Since my hometown police's description of me was a seventeen year old male homosexual', the Roanoke police began trolling the usual homosexual' hangouts in search of a clue to my whereabouts. They harassed anyone suspected of homo' activity looking for information. But since I hadn't been active in the normal' gay community, there weren't many around who knew me, and those few who might have seen my disappointing try at streetwalking either weren't questioned or if they were, weren't talking.

So, for now at least, I was saved by the fact that the police were looking in all the wrong places.

And so I worked the streets at night and lived the life of a hermit during the day, waking usually no earlier than noon, staying inside until Bill dropped me on the street at night. No life outside Bill's house and the street.

In Bills house, I learned everything I know about makeup from Cookie. By the third night I was in charge of it myself, following her directions and applying a pretty good `face'. I leaned the secrets of eye liner, mascara, rouge, lipstick, and nail polish before going on to the more involved aspects of body care.

Never one to have a lot of body hair, I nevertheless learned the secrets of shaving. First my legs, and eventually my whole body. The feeling was electric, and even though I only removed `fuzz' from my legs and arms, I felt as if my body was as smooth as a baby's. Two days later I discovered the amazing Nair, and used it every other day to stay smooth.

And on the street, I learned tranny specific tricks of the trade from Mandy and Cookie, like how to roll the sides of my panties to make the crotch tighten and hold my tucked penis in place. I learned never to wear a dress before first tucking and later, when I became comfortable with it, I tucked no matter what clothes I wore. I also learned to use a tampon after fucking to absorb the semen and keep it from seeping from my hole and staining my clothes. And I learned to carry baby oil as a lubricant for anal sex. It not only lubricated, but also soothed raw tissue. Both of which necessitated a purse or handbag to carry them in.

But the best of all the things I learned was that I adored the attention I got when I was on the street. I loved to be on display, with my short shorts or my dress showing off my cleanly shaven legs, thin waist, and bra (padded now with tissues) giving the illusion of a young girl's tight budding breasts. As my hair grew, I kept it pulled tight in a pony tail and wore a pair of large clip on ear rings and several ring bracelets that Cookie had stolen from Family Dollar Store for me.

I even came to terms with my high heels. After I saw what they did to accentuate my legs I began to practice wearing them during the day until I became proficient enough to wear them out at night, first with my dress and eventually with everything I wore.

During the day I wore an old oversized tee shirt, panties, and flip flops around the house. When I came to Roanoke with Clarence I only had the clothes on my back, and those were long gone now, leaving me with nothing but girls clothes to wear. And, funny thing, I couldn't imagine that as being anything other than normal.

Thursday was my third night on the street, and a fairly typical of the few weeks I spent there. I began getting ready just after dinner, first my face, then my hair, and finally dressing. Tonight was my first in a dress, and I was eager to experience this new step in my transformation. Although I might have been mistaken for a boy in my short shorts and tee shirt, there was no mistaking me as a girl in the black, sleeveless mini dress.

By 7:00 pm I was ready, but Bill said that was too early for me, so as he drove Cookie to her `spot' on Salem Ave, I watched TV. Well the TV was on, that's true, but I really spent most of the time checking out myself in the hall mirror. I was astounded at the girl who stared back at me. Tall (thanks to the heels), with smooth creamy white legs that reached all the way from the tops of the heels before disappearing into the tightness of my short dress. The curve of my hip tapering into the dip of my waist. Across my flat stomach which complimented and set off the slight swell of my faux breasts. My bare shoulders and arms, my slightly made up but fresh looking face, and my blonde hair pulled back in a pony tail that hung down the back of my neck and swung from side to side as I walked. The more I looked, the more my tucked penis strained to escape the confines of my panties.

Funny. I thought to myself, I've been outwardly effeminate since my summer at conservatory, becoming more and more so as time went on. Effeminate behavior was natural to me, but I had always felt unusual – effeminate yet dressed in boy's clothes. I had an epiphany that night, although I still didn't fully appreciate it, and that was instead of being at odds with each other, my looks now matched the way I felt. Effeminate felt right in these clothes. And instead of being a queer in girls clothes, these clothes felt right alongside my effeminate nature.

I was on the street by 10 PM, dropped off by Bill on Mandy and Cupcake's corner, and I would work til 3 AM before he picked me up and took Cookie and me home. It would go like this for the next three weeks, sometimes later depending on traffic. I would average 2-3 tricks a night, less during the early week and more on Friday and Saturday nights.

I learned the `look', the walk, and the patter from Mandy and Cupcake, the only two hookers working during the week. I matured at least 3 years in those three weeks, evolving from a shy 17 year old, unsure of myself, with no confidence in what I was doing, to a street hardened hooker, with the looks and the attitude that attracted the type of man who would pay for sex with me.

My johns, I observed, fell loosely into two categories, the first (who I called nearly straight') were mostly husbands or boyfriends who weren't getting what they wanted from their wives or girlfriends and thought nothing of dropping $20 for a blowjob. I called them nearly straight' because they would never consider getting head from a boy or man. But the illusion of a woman that we presented made it alright. As long as we projected a passable submissive feminine image, they were OK with it. And, to be quite honest, Cupcake and I, at least, were passable. These guys were about instant gratification, with little talk beyond the deal, and even less after they had cum. One hundred percent wanted a blowjob, fully dressed, no foreplay, no play afterwards. I had been sucking dick since I was 14, so it was safe to say that I liked it and I enjoyed giving these guys what they paid for. Their mechanical attitude and complete indifference to how I felt or what I may have needed was completely beside the point and I didn't concern myself with thinking about it.

But the second category, and their were only two in three weeks that fit it, were the ones who touched me to the core, in a way I had never been touched or affected before. They were, I would learn later, bisexual and they treated with a respect and compassion that reinforced my desire to be with them, to experience the true meaning of a sex object. With them I felt completely at ease and complete in my feminine self. I was for them, they were for me, we were for each other in complete sexual harmony. I know it sounds strange, but being with them foretold how I would come to form my sexual self.

All three tricks tonight would be of the first category, with the first deal being struck shortly after I arrived. An older black man in an old red pickup truck would go through the negotiation `dance' with me, agree to the $20, and invite me for a ride. After 5 or 6 blocks, he pulled off the street into the parking lot for some electrical supply company. He edged the truck into a narrow space between the building and a dumpster and left the engine running while I worked on his belt and pants to free his huge dick. It must have been 10 inches long and as fat as any I had ever seen before. I laid across the seat and dropped my open mouth to the head. I could tell I was going to have a problem getting this all in my mouth and started to jack him as I licked around the head. His scent was over powering, he had obviously cum not too long ago and not cleaned (or been cleaned) himself and I almost gagged as the smell hit my nostrils. It became a little more bearable as I got the head in my mouth let my sense of taste offset, just slightly, the smell. My tongue was working around the head, from the bottom, clockwise, and my saliva washed some of the dried cum from it and I concentrated on the taste rather than the smell as I started to stretch and take more of him inside me. My hand continued to jack as I got into the task at hand and began to lose my self in it.

He was getting into this as well, running his hands from my head to my bare shoulders to my back as I bobbed up and down on the top third of his cock. I was laying flat on the seat now, my feet off the floor and wedged between the dash and the door, my dress riding up to expose my panties. I don't know if he appreciated the view or not, but it certainly didn't turn him off, and I felt his hand caress my ass cheeks.

`Wanna fuck me, baby?' I asked, taking my mouth off his cock for a second.

`Nah, jest suh ma dick off.' He responded. Probably a good thing, this dick would , in all likelihood,, split me open.

`MMMMffffffffhhhhhhh' I groaned as I took that dick in, trying to deep throat it but failing after about half the length was inside. I settled in to a slow blowjob, letting his dick slip from my mouth on the upstroke and impaling myself on about half of it on the down. As I worked, my throat warmed up and I got the head past my gag reflex but couldn't keep it there more than a few seconds before having to pull out a bit to get air. Meanwhile my hand tightened around his cock and I increased the jacking tempo.

`Ahhhhhhhhhh...aaaaaa...' he moaned as I felt the tell tale signs of his orgasm building up from his ball sack. I no sooner squeezed them before he let loose the first pulse of cum. I pulled back until the head was in my mouth and started drinking down the first of what would be four swallows of strong tasting cum. He held my head tightly until the spurts trailed off, while I massaged the cockhead by relaxing and contracting my jaw muscles to milk out every drop of the tasty reward that I had earned.

`Ahhh...good.' was all he said as he pushed my head away and zipped up. I knew enough to realize that he was finished with me, satisfied meant no longer interested, and once money was exchanged he reached across me and opened my door.

`Out' he grunted as he straightened back up.

`But I...need to get back...' I stammered.

Then fuckin' walk' he growled as he stiff armed me across the seat. Knowing that it was useless to argue, I climbed out of the truck, straightened my dress, and began walking in the direction I thought was toward Cupcake's corner. As the truck passed me on my way I heard him say the other way Mary'. Well, at least he saved me a long trip, and I turned around and walked the other way, realizing that, for the first time, I was outside dressed and not on `tranny street'. It felt sort of exciting and sort of scary to be out like this, but by the time I arrived back at Cupcake's corner, it seemed as natural as could be.

To be continued

tvlesli@gmail.com

Next: Chapter 8


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