Young Times

By sissi lesli

Published on Nov 4, 2013

Transgender

Young Times – The Inbetween Years – Part VIII

This is, for the most part, a true story based on my real life adventures (and misadventures) from the summer of 1982 thru end of year 1983. The period, and these events, are significant for me because during them, I came to understand and accept myself as who I was and wanted to be. My journey from point A' to point B' in role development began and ended during this time. As I became more and more comfortable with my new self, the journey and the development proceeded at warp speed toward the person I am today.

I'm sparing readers the `flashback' style of the previous seven parts of this series. I think you all have an idea of what I am today, so I intend to concentrate the remainder of this series to those early days.

If business on the street was slow and relatively calm during the week, the weekends brought it to full tilt boogey. Call it `payday largess, weekend crazy' or whatever, but the fact was the action picked up substantially, both good and bad.

The good because Friday was payday for a large segment of this blue collar cesspool that called itself Magic City', Traffic picked up for the genetic girls down on Salem Ave who flaunted their wares as they dodged the police trying to get them as far away from the city market as possible. As long as the girls stuck to the shadows of the abandoned buildings around 5th Street the cops were cool and generally didn't hassle the girls or their johns. Us trannies, whose ranks swelled from three to four on Friday and Saturday nights, stuck to ourselves on our' block of 7th Street between Salem and Norfolk Avenues. Since we were in an `undesirable' area of mostly closed warehouses and former businesses, the cops rarely, if ever, hassled us. There were no neighbors to complain, and we kept a low profile as much as possible.

Danny was part of the good, showing up early Friday, just after Bill had let me out on Cupcake's corner. I didn't even have time to chat with her and Mandy before he pulled up in front of me and motioned me inside. I bid a quick `bye' to the gurls and slid in beside him.

Good God' he exclaimed as he gave me the once over you are gorgeous. That dress is stunning on you."

`Thanks, I try' I nearly blushed. Where was the street strut, the tranny patter I thought I mastered. I felt like a shy 17 year old girl, which I know now I was.

`No parking garage for you, lady. Let's get out of town where we can have some real fun.'

`Sure' I agreed . I had no idea what time limit I should set, if any, on this. Bill seemed satisfied with the tricks I turned over the last three nights, so I figured I had some latitude.

Danny turned the corner onto Salem Avenue and headed in the direction I had learned was towards Bill's house. He drove past the turn I remembered Bill taking and kept driving into an area I had never seen before. I would later learn that we passed thru Vinton and into the county before taking the on ramp to the Blue Ridge Parkway and heading north. After another one or two miles, Danny drove up into an overlook just off the Parkway. I would come to know this particular overlook in the years ahead as a popular `makeout' spot for both hetro and homo sex. Apparently the park rangers didn't pay too much attention to what went on there.

Danny drove around the loop checking things out, and I noticed five or six cars pulled into the diagonal parking spots. Heads were visible in some, not in others, and I saw several figures standing by one car looking in. My experiences in the park back home suggested that this was a place people came for sex.

Danny turned the engine off and the quiet of the night engulfed us. Except for the chirping of the cicadas, there was complete quiet.

`Come here' he broke the silence as he reached out for me. I slid across the seat and into his embrace. His lips were on mine in a flash, and his tongue slipped into my willing mouth. God, how this turned me on.

I had been kissed by a boy before, but that was a case of two boys kissing. Definitely a homo thing. This was different, Danny was kissing me and I was kissing him back like a girl kisses a boy. He was the aggressor and I was the willing supplicant. And it didn't feel homo at all. In fact, it felt like the most natural thing in the world, and I gave myself to it completely, wrapping my arms around his neck as his circled my waist and pressed his body to mine. There was no rush to this, I was content to stay here in his arms as our tongues explored each other's mouth and his hands ran lightly over the curve of my body. I unwrapped my arms and brought my hands to either side of his head, holding and caressing his wonderful face as he pulled me tighter and our tongues continued their dance.

Tucked or not, my penis was on full alert, straining against the fabric of my panties to escape and find attention. I was shocked, surprised, and excited to feel his hand push my dress up in front. I spread my legs, giving him full access, and he responded by slipping his hand against my penis and gently rubbing it through the silk of my panties.

`Ohh...gadddddd.' I gasped at his touch, my penis rock hard now. He responded by gripping the shaft and gently jacking me thru the fabric. I was on fire now, starting to lose the ability to stay still. I pushed my groin into his hands and tried to spread even further as his hand moved down below my ballsack header for, I presumed, my ass, But, to my surprise, he stopped and moved higher, running his hand lightly over the wet spot in the front of my panties. As soon as he had sopped up some of my precum he brought his fingers up between our lips so we could both have a taste of pre sex cum. It was delightful and one of the most erotic things I've ever had done to me.

I was so hot that I had to have him, and I moved my right hand down between his legs where I felt the hardness of his cock. He was on fire too, and I unzipped him as his hand dived back between my legs, all the while our tongues played, probed, and lapped at each other. This time he went for my ass, pushing my panties aside, spreading my cheeks slightly, and probing with his finger. A shutter went through my body as his finger tip pushed against my tight puckered hole, and I relaxed my sphincter as much as possible to greet it. He pushed harder and I felt that wonderful feeling as my sphincter gave way and his finger slid inside my hungry cavity.

Even though my every thought was on what he was doing to me, my reflex action was as if I was on auto pilot as my hand attempted to free his cock from the confines of his underwear. The tip of his cock was wet with precum and I knew he must be as hot as I was. His finger was buried to the last knuckle in me as my anal canal involuntarily gripped, and squeezed around it as if I was trying to milk it. But he began to withdraw it, only to slide all the way back in, then slowly withdrew, bringing his finger up to my mouth. I sucked it in and delighted at the aroma and taste of my insides on his finger. Hungry now, I took a second finger in my mouth and slathered it with saliva. He then slipped both in my ass, which gladly accepted them. The pleasure was even more intense now that he had two stretching me. He continued finger fucking me as I pulled gently on his cock.

`Ohhhhhh...mmmmmm...' I moaned and rolled my head from side to side. The delirium was building and I was starting to lose focus, as my ass surrendered completely to what was going on down there.

He responded by bringing his fingers to my mouth again, and this time I took three inside to suck on. I slobbered and slathered them, knowing full well what he intended to do with them. My sphincter gave little resistance to them as he resumed finger fucking me and the fire in me ranged now. All my senses seemed to be centered in the fucking I was getting and I could feel myself stretching and relaxing with each thrust.

I was doing some serious jacking too and Danny was as hard as a rock. This was HEAVY petting, the likes of which I had never known. I got a lot of satisfaction from giving men pleasure, and I had done a lot of that, but this was different. I was on the receiving as well as the giving end. Other than a 69 or two with Donnie or Stephen, I had never, ever, been this hot. And, other than some playing around at conservatory, I had never been finger fucked before. It was driving me to the edge, very quickly.

I wanted to stop, to make it last longer, but I had no will to do it. Danny's fingers were turning my anus into a wet, sloppy pussy like hole and I craved it and more.

I came up for air long enough to lift my ass off the seat and tug at my panties. Danny got the message and pulled out long enough for me to pull them down to my knees. He pushed them down from there to the tops of my high heels which I promptly kicked off, allowing me to step out of the panties.

`I want you to fuck me – NOW' I demanded and shifted position so he could get in the floor on his knees. As soon as he was there, I leaned against the seat and scooted my legs around to be spread on either side of him then raised my feet and placed them on the dash, sliding forward until I felt his cock on my ass. I reached down with both hands and spread my cheeks for him as he placed the head against my slightly gaping hole. The feeling was electrifying, and I took in a sharp gulp of air to keep from swooning.

His precum was all the lubricant we had, but in my state I it didn't matter. I was so stretched by all the finger fucking that there was little pain as his cockhead cleared my sphincter and the shaft quickly followed. One or two short pumps and he was buried inside me, his pubic hair mashed against the smoothness of my shaved ass sheeks.

Now I'd been fucked my guys before, plenty of times, it was a homo thing. But I had never given myself so completely to anyone like I was giving myself to Danny. A lot of it was because of all the foreplay, something I had never really known before. But a lot of it was (I would come to learn over time) that I was coming to grips with my feminine need to please a man. And I was vulnerable enough, emotionally, to give everything in myself to that man in exchange for him treating me like the woman I so much felt like. And Danny was the first man to do that. The first to touch my feminine side with an understanding of how I was feeling. I was a tranny, sure you could categorize me that way, but no matter what you called me, you couldn't change the way I felt. One thing I wasn't, and tonight proved it to me beyond a shadow of a doubt, was a faggot dressed as a girl. That `faggot' thing was like a train that had left the station, it just wasn't there anymore. Now I had the feelings to go with the looks, and I never wanted this to end.

For the first time in three years I was truly happy, and about to get happier.

Danny grasped my ass and lifted me off the seat slightly as he continued to slowly fuck me. I grabbed the back of his legs with my hands and pulled him closer, trying to get as much of his cock inside me. It felt as if his cock was in my stomach on the in stroke and as if I was going to poop on the out stroke. To this day I have never forgotten the pleasure he gave me that night.

I didn't notice the faces of the men who had gathered around Danny's car. There were at least three and they were watching us through the windows. I'm not sure it would have made any difference to me, I was complete engrossed in sex at this point.

`Oooh...aaaaa' Danny moaned as he pounded my ass. I tried to moan but found myself unable, in a trance like state, focusing on nothing but his cock sliding in an out of me. My own climax was building and before I knew what was happening my cock was spewing come all over my leg and Danny'stomach. I had never cum from a fucking before and the feeling was awesome. Instead of peaking after I came, like most times, my delirium hovered and the feeling of sexual arousal never diminished. I felt as if I could keep doing this all night long.

But Danny was as hot as I was and his climax was soon in coming. I felt the first powerful spurts as they further lubricated my anal canal and the warmth of his cum heated my insides. He came in me for what seemed like minutes, a near steady stream of semen filling my bowels to overflowing. My sphincter was sealed around his cock, so nothing was running out and I felt as if I had been filled by an enema, I had never experienced this much flow and I began to have doubts about holding it all.

Danny was still now, his cock softening but remaining in me. As my sphincter tightened (or tried to, it was stretched to the tearing point) it slowly forced his cock back until it finally slipped out with a plop as my hole clamped shut. It was then that I remembered the tampax that Mancy had given me the night before. I swung my legs around and searched in the floor for my bag. Finding it, I fished out the sealed tampon, tore the packaging open, and inserted it into my sopping wet hole with my right hand while pushing the tube to seat the soft cotton device in my rectum.

Impressive' Danny said as he watched me finish the insertion. Where did you learn how to do that?'

`A trick of the trade' I joked as I reached up to touch his face. He responded by leaning into me and engulfing my lips with his. I opened and let his tongue play inside my mouth, the fire starting to stir again.

It was while we were cleaning up that we noticed the men outside.

`What are they doing?' I asked.

Aw, just looking. They get off watching sex. Does it creep you?

Actually, no it doesn't' I admitted. I've done some group'.

`Well, they're harmless. Just want to make sure it doesn't bother you. I don't want to do anything that bothers you.'

I didn't realize it at the time, but our exhibition here tonight would come back to haunt me and throw another wrench in the works. But that was weeks later.

`Baby you do all the right things as far as I'm concerned. All the right things.'

`Uh huh, and I haven't found anything I'd rather do than do them to you. With you.. You are the hottest chick I know.'

My ego shot about ten feet high when he said that. So it wasn't just me who felt touched by what we had just done. Here, in Danny's words, was validation of all the things I had felt over the last few days. Here was acceptance of me as the person I had discovered, as the person I so wanted to be. The role I was comfortable with. Sure, I was passable and could fool some men into thinking I was a girl. I had the clothes, the looks, and, increasingly the mannerisms of a girl. But now I had confirmation that I could take it farther. I could BE that girl so well as to be indistinguishable FROM a real girl. And that would be key to my life from now on.

I slid close to Danny and wrapped my arms around his neck as he pulled out on to the Parkway and headed toward town.

`I want to see you again' he said, further stroking my ego.

`Me too' I replied.

`I don't mean like tonight...I mean...like a date, you know? Can you go out...I mean...not working...like a date?'

I was flattered and I was excited, but to be honest, I was completely unable to answer his question. I had no idea if I could go out, I hadn't been allowed to since coming to Roanoke and., to be honest, I had never felt the urge to. But here was an opportunity I definitely wanted take up – a date – wow, could this get any better?

I don't know' I admitted Bill...you know, my ...ahhhh...'

`Your pimp?'

`Yeah, my pimp'

`You have to ask your pimp if you can go out – on your own time?'

`Uhhh...yeah. I live at his house. I don't have my own place or anything. He drives me to work and he picks me up when I finish. He takes care of me.'

`Of course he takes care of you – you make money for him. But you should have your own time, you know? You should be able to go where ever you want when you're not working. Jesus Christ, he can't keep you a prisoner in his house.'

`I...I don't know if he would let me Danny. He has strict rules about what I can do. And I can't piss him off, cuz he could send me home and then I'd die. I just have to stay on his good side.'

Send you home?' he repeated what do you mean?'

`Well...I...I mean...uh...I'm not from Roanoke. To be honest, I ran away from home, and Bill and another man have been taking care of me...and...and I have to make money to pay for my share. You know, food, clothes, and all that. And if I can't make enough money Bill has threatened to put me on a bus for home.'

`You're a runaway? Send you home? How old are you?'

`Seventeen' I mumbled.

`What?' his voice rising now.

`Seventeen'

`Holy shit – seventeen – holy shit. You're jail bait. And I could get twenty years in jail for what we've done. Holy shit – and you're a runaway. Are they looking for you?'

`Who?' I asked, genuinely confused now and starting to get just a little upset at his tone.

`Your parents? The fucking police? Surely somebody is looking for a seventeen year old runaway.'

`I don't...I don't know' I admitted, my voice breaking as the emotion took hold. I had never even given these things any thought for weeks now. I was away from home, I was living a grown up life, who cared that I ran away from home? I belonged here, I enjoyed being here. This was my new life. Why the hell should I worry?

Shit' he exclaimed I can't afford to get arrested with you in the car. I can't go to jail. My wife would take me to the cleaners in a divorce if I was caught with a prostitute. An underage prostitute at that! Fuck'

`But...but I thought you liked me. I thought I made you feel good. I thought you wanted to see me again' I choked the words out as my emotions took over completely and I fought back tears.

`I do. You do. I did. But not enough to go to jail for. I mean, you're a good looking, sexy tranny and I have enjoyed your company. But I can't risk losing everything I have because you ran away from home before you came of legal age. I just can't do that.'

I was speechless. I had nothing. My emotions were completely sucked out of me now, I sat, numb and quiet starring into the dark of the night as Danny drove.

This is as far as I can take you' he finally said, pulling the car to a stop in front of the Transportation Museum. Three blocks to walk, that's all...I just can't risk any farther'. And with that, he reached across me and opened my door, leaving no doubt about what he wanted me to do.

He pulled off as soon as I was on the sidewalk, without a goodbye or a `see ya around' or anything. Tears welling in my eyes, I began walking west on Norfolk Ave in the direction of 7th Street. Dejected, and still too young and naïve to feel contempt for this man. My head was still too far in the clouds to realize the disdain he had shown toward me, his refusal to give back the love I was feeling for him.

No, I was the victim tonight. Tonight was the beginning of the `hardening' process that would help wash a little of that naivety from me and replace it with street tranny smarts. The kind of smarts a hooker needs to survive in this world.

To be continued

leslitv@gmail.com


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