Young Times Pt II
The joint had worked its magic and in short order I was feeling quite a bit better. Better enough that I actually decided that a bath was in order. I swung my legs over the bed, pivoting to an upright position, and pushed up, standing. Swaying, but standing. Oh my God, I had done it again, what must have been a pretty wild party with those two cowboys was coming back to haunt me this morning.
You're no spring chicken' I told myself, and then quickly ignored my own assessment. I'm as young as I feel' I said outloud, confident that I could make the few steps across the room and into the bathroom without vomiting. And that I did.
The bathroom was small with a commode on one wall and a bathtub/shower combination along the longer one. I sat on the commode and adjusted the bath water to a pleasing temperature. I ruled out the shower, too much standing, and let the tube fill, slipping in before it was half full. Ahhhhhh, the relief was almost instantaneous and I vowed to stay there all day. I fished the washcloth from the water, tore open the wrapper for the soap, and began working up a lather on the cloth. The suds were gentle on my skin and I began gently lathering up, first my legs, then my stomach. Cupping my left breast with the wash cloth I marveled at how the estrogen had produced such perky, attractive breasts and how they had remained that way for the past thirty years. I knew women my age who would kill for this youthful look!
My hole, however, showed the ravages of time. Tight in youth, thirty years of taking cocks of all sizes, shapes, and colors had left it with little elasticity. Still it was just the least irritated as I passed my fingers over it, no doubt to the credit of my cowboy friends. We had partied with pot and beer and cigarettes, shooting the shit as we got high. But when it came time for the sex, they weren't quite drunk enough for a three way so they did me separately, one with me while the other waited outside. In fact one of them did me twice, but didn't want his buddy to know. I was so fucked up that I ended up showing off by eating his cum out of the condom when he nutted the first time and that set him off on a marathon fuck, the aftermath I was feeling this morning.
As I settled back in the near full tub the water washed over my skin and the years washed away...
Young Times (the between years) Part 2
In all honesty I've thanked my lucky stars again and again that Cookie came along at that particular time in my life. No, to be honest, I've thanked the stars that she came into my life period. Cookie, quite accidentally, was the motivation that changed my life by showing to me a path forward that addressed, no corrected, my here to fore held perceptions of myself and those like me. To say that I wasn't who I thought I was is a minimization of just how far wrong my life was headed and how clueless I was about myself.
After putting me in high heels and coaching me how to deal with them, she turned next to make up. I was never a hairy person, facial hair never materialized, so any make up I needed was minimal. She used a light powder base with a little reddening of my cheeks, an eye liner pencil to define my brows, and dark red lipstick to highlight my lips with a dark liner at the edges.
Since Bill was not going to invest in clothes for me until I proved my worth, Cookie did a trim job on my shorts (I didn't think they could highlight my crack any more than they did but she masterfully trimmed the back until my cheeks were separated and what was left of the shorts disappeared between them), and cut my tee shirt until it was little more than a top with my flat stomach exposed. Then she cut the sleeves at my arm pits to show more of my upper arms.
When I studied the results of her work in the mirror I was amazed. Gone was the skinny high school faggot, and standing before the mirror was a cute, if slutty, high school girl. To complete the illusion, she helped me apply a bright red polish to my finger and toe nails.
It was then, for the first time, that I felt somehow complete. My body reflecting what had been repressed all these years. My feminine side I guess you could say.
Let's be honest, I had been a sissy for the past few years. But being a sissy faggot queer is nothing more than the widely held stereotypical view of a homosexual. And I suppose that a queer dressing up as a girl isn't that unusual, but I actually didn't feel like a queer dressing up. Something touched me deeper than that, and while confused, I found myself inching closer to the realization that I liked being like this.
Bill took a completely different view, to him I just might be marketable, something to finally make the money he and Clarence had expected to make for their investment. And he couldn't wait to test me out.
Fo sho ya gonna make dolla tanite' he exclaimed, Fo sho'.
`Ohyeh, fo sho, look betta dem tranny honey' Cookie chimed in.
So the die was cast, and to be honest, I nervously looked forward to it. Dressing like this and being on display on the street, oh yeah. And the chance to make money so I could stay here and not be sent home? Priceless!
Bill wasted little time in testing me out. By dusk he was teathing at the bit to get going and he and Cookie bundled me into the car and drove thru the city, west on Salem avenue to Loudon and 5th. It was a run down part of the city, some distance from where I had tried to hustle, just past the Park, Roanoke's gay club. Two blocks back from the traffic of Salem Ave, it was a dark place illuminated by a lone street lamp and not much else. The buildings in this part of town were dark, either abandoned, or slated for demolition, if not both. Cookie, bless her soul, was my guardian angel' that first night, giving me the pep talk and low down on how dem trannies do'. It seems that the trannies were trying to scratch out a living just like the genetic girl hookers were doing and didn't take kindly to competition. Especially, as it became obvious, if the competition was a dead ringer for the real deal. And, believe me, trannies, especially the black sisters, can be a real cat fight if they want to.
Cookie set them straight. We Bill's ho's, boton us' she announced to the two girls' hanging out on the corner. Betten not fuck wid eiedus, les you wanna get fucked up, eite?" The message was clear, succinct, and immediately acknowledged by the white, skinny, and pimple faced (even through the cake of makeup she' had on her face). The other, an overweight black thing who was actually prettier in the face, tipped her nose skyward and walked away.
Hey bitch' Cookie called out to the retreating whore, I sayed eite?! Doan make me get'n yo face'.
Doan hafta bring ya white trash bitch up in here take my bidness' the girl' shot back.
Mutha fuck you tranny' Cookie lit into her, my sista come up heah lukin betta both you shemale ho's. She be brangin class to this shit hole ya call yo bidness. She git bidness to dis place lak you neva seed, woncha honey?'
`I...I...sure' was all that I could respond with. I was mesmerized by the verbal back and forth of these two.
Cose ya will honey' Cookie reassured, and I saw the black girl' stop and focus on me.
Dat a girl' she said, not quire sure what she was looking at. Dat a ...?, No, dat ain' no boy! Sheeit!'
`Lak I say, bitch, she gonna git bidness comin here wid dat ass and dat face. Mo bidness dan you git nigga, mo tranny luvers dan you kin', Cooke spat.
Sheeit' the girl' exclaimed again as she walked away from the confrontation, seemingly whipped by Cookie's brash nigger talking.
`Eitha you or any other tranny ho's be messin wid my girl here gonna be hellta pay. Me and Bill gonna come lukin fo yo tranny ass to kick. You unnerstan me, bitches?'
"Yeah' the white `girl' said.
Whatevah' the black one murmured then quickly followed up yeah I unnastan'.
Crisis averted? Or just postponed? Time would tell.
And, while I would come to count these gurls among the best friends I had in the world, tonight – my first night on the street – they were the closest thing I had to enemies in my short life. And uneasy truce was struck that night as they moved off to the center of the block, leaving Cooke and me under the street light as she gave me final instructions meant to help me `make a dolla' without going to jail in the process.
Doan nevah axt fo money. Doan nevah gi a price. Make the john set da price. De axt, you say make a offa'. Cops cane make no offa. And, watevah ya do, doan go gittin in no car til da price be settled. An, no matta how ya might wan dat dick, doan gi nothing away. Bill kick yo ass ya gi it away. Gi yo paper baby, its all bout yo paper'.
`You're not going to stay here with me' I asked. It sounded like a plea.
`You be fine. You look fine. Ya see how deese tranny bitches look? De look like dey playin dress up. You look lak a gotdamned, honest to got girl. And a gotdamned gua luker too. Ya be fine. I gotta go make a dolla fo Bill kick my ass.'
And with that, she gave me a peck on the cheek and walked back up the street to Bill's car. They drove past me and past the corner where the other two hookers were standing, giving them a long warning look as the passed.
Then I was really on my own. My eyes had adjusted to the darkness that enveloped the part of the block I was standing in, where the streetlight wasn't, and I could make out how shitty a part of town we were in. Abandoned, or what looked like abandoned, buildings intermingled with empty lots, grass grown high and sprinkled with trash. Compared to the gay area I had streetwalked in this place was like some third world country. I guessed, correctly, that transvestites didn't rate surroundings like the genetic girl and homosexual hookers did. Out of sight, so to speak.
But something about being out here, dressed like this, excited me. Exhibitionist? Sure, I'd known for a while that I enjoyed being watched, being seen. But something else, something even more enjoyable. The clothes? Perhaps. The illusion? Yes, the illusion, the playing of a role. Of a girl. Only, was it role playing or was it assumption of a new identity? An identity so out of this world compared to what I had identified myself with just a day ago. I still had a long way to go before I figured that out, but at this juncture I was aware that something was working on me. And I seemed to enjoy it. It excited me.
I noticed action at the end of the block, a car turning onto the street, slowing as it passed the two hookers. Stopping. The white `girl' approached the car, leaned in, and after what appeared to be a conversation, going around the the passenger side and getting in. The car then sped down the block past me and took a right turn, and disappeared from sight. So that's the way it's done. All pretty simple I thought as I recycled the advice Cookie had given me.
I had been standing on the sidewalk in the dark and it occurred to me that no one could see me there, so I edged out into the street where the light shone a little brighter. I caught the black hooker starring at me and I quickly looked away, afraid she would say something. But she didn't and our uneasy truce was still intact.
After what seemed like forever, car lights cut the darkness at the opposite corner and a car came rolling slowly down the street in my direction. I stepped back up on the sidewalk, sure that whoever it was had seen me and anxious to put a little distance between me and the car. Just in case. It slowed and finally stopped even with me as the driver obviously checked me out. It didn't move. I was being checked out even more now.
Wake up stupid' I thought to myself, finally, what are you here for? Looking good isn't going to cut it with Bill, you need to make some money'. And with that I finally stepped off the curb, trying not to break my neck in these shoes, and did what I thought was a sexy stroll toward the car. The passenger side window was down and I bent down to see inside.
`Whoaaaa, lookin good. Where did you come from girl?' the driver, and lone occupant of the car, asked.
Just got in town' I answered, trying not to sound too masculine' which for me wasn't much of a problem. My normal tone of voice seemed to have sissified over the past few weeks.
`Well, hell, welcome to town. How much does a sweet young thing like you charge for a blowjob?" Cookie's voice rang in my memory immediately.
Make an offer' I said, and right then and there another thing rang out that I just had to add for effect, and don't worry, you can't insult me.' Brilliant I thought.
`OK, hop in' he said, reaching across the seat and opening the door.
`Offer first' I insisted.
"OK, OK, I'm no copy, don't worry. Twenty for a blowjob, OK?'
OK' I acknowledged, I'll ride with you' and got in.
I noticed the black hooker starring at me as we passed her. Daggers.
`I'm gonna go to the rail lot parking garage if you don't mind. By the way, name's Danny'
Cool' I replied, not having the first inkling of where that was I'm Lesli'.
Pleased to meet you Lesli' Danny said and you're some looker, I thought for a minute there that you were a real girl' `And what tipped you that I wasn't' I asked, delighted that I made such an impression.
`Well, the fact that you were in the shemale block for one thing.'
`Oh' I said, not sure what a shemale was, but thinking it was kina cool name. And before I had time to ask, he was wheeling into a high rise parking garage next to the downtown train tracks.
No security cameras in this garage' he chuckled and no charge for parking after 6 PM. Makes this a real popular place'.
We parked on the second floor at the far corner from the elevator. The only car there, so privacy wasn't going to be an issue I suspected.
Let's get in the backseat' he instructed more room'. I opened my door and he followed me out and into the backseat. He was immediately all over me, squeezing my legs and running his hands under my tee shirt, pinching my nipples.
God you're something' he gasped as he kissed on my neck you're the best looking tranny I've seen apart from one or two in magazines. Get your clothes off so I can look at that body'. I pulled the tee shirt over my head and he immediately bent to lick and kiss my nipples. I was getting extremely hot from all the attention and the fact that I had not had sex in weeks. Danny knew how light my fire for sure. As I melted into the back seat his mouth was on mine and I opened my lips to accept his thrusting tongue deep inside. I was on fire, ready to burn out of control. I had to have him!
`I want your cock' I moaned as I slid my hand across his stomach, reaching, searching for what I knew I needed.
And you'll have it' he whispered as he guided my hand to his belt buckle. As I tugged at it he was unzipping and the combination of our efforts brought quick results. He raised himself off the seat and pulled both his pants and underwear down, making way for my hand to grasp his rock hard cock. It was what I've come to call average', about 8 inches, circumsized, in essence just the right size for me in those days. I could get something that size in my mouth without straining and deepthroating a cock that size has always been a pleasure. Nothing wasted. Nothing for the hand to do. A cock I could make love to entirely with my mouth, tongue, and just the slightest bit of throat action.
But tonight, after three fruitless weeks of seeking sex, it looked, felt, and smelled like the most wonderful thing in the world. I lost no time getting down to it, licking all over the head as I gently jacked the shaft with my hand. Danny was going into orbit as I closed my lips around the head and continued my tongue caress on the underneath side. I was glad it was cut, not that I don't like uncut cock, just that I like cut ones better. Lots to tongue wash right off the bat, no waiting or pulling of foreskin. In fact, my preference is to get the cock in my mouth as soon as possible so I can take in the true taste of it before I flavor it with my lipstick, saliva, or cum breath. I like to get it in my mouth where my talent lies and make that first impression on my man. I know I'm an accomplished cocksucker, I want him to know and remember it from the first to the last of the encounter. I lick and nibble the cock and balls only after I've had it in my mouth long enough to bathe and slather it with my mouth and tongue. I always give it the attention it deserves up front, before I start playing around with it.
Oh, my god' Danny moaned above me, your mouth is sooooo hot'.
`Ummmmph' I moaned as I lowered my head on it, taking it past my gag reflex and into my throat. My hands went to Danny's legs and I ran them lightly along, feeling the goose pimples I was causing along the way. My hands were free to roam because his cock was totally under the control of my mouth. I was in synch now, bobbing up and down on his shaft, letting my tongue flick out at bottom of the stroke to caress his ballsack. I was using the cocksucking skills I had developed over the past few years to advantage on him, he was coming closer and closer to climax.
`God, I want to fuck you' he exclaimed.
`God, I want you to fuck me' I replied as my mouth came off his cock for the first time since we started this. I was serious, my ass burned to have this cock inside me. As much as I wanted to taste Danny's cum in my mouth, I wanted it in my ass more. I was on fire for it, and the only thing that would cool that fire was a good drenching way up in there.
I have twenty bucks, that's it' he moaned I don't have any more cash and I don't get paid til Friday'.
I don't care' I gasped, I want you in me. I want you to fuck me'. It was the truth, and at this very moment, money meant nothing to me, the passion burning in me for this man, actually for any man, clouded out everything else. I had to have this. I had to be fucked, and cummed in.
`I don't have a rubber' he admitted.
I don't care' I assured him it doesn't matter. I'm not going to get pregnant'.
And with that ice breaker we got down to business. I pulled my shorts off and, as Danny knelt on the back floorboard, I slid forward until my ass was at the edge of the seat and pulled my legs up until my feet were resting on the front seat, spread on either side of Danny. Impatient to have him inside me, I reached down and guided his cock until the head was firmly positioned against my hole. I was tight, and Danny was gentle, but it still hurt and I cried out as I felt the first stab of pain. He recoiled.
No, don't stop' I groaned thru clenched teeth, put it in'. Danny complied and I cried out as the head slipped past my tight sphincter and into the warmth of my love canal. I pushed down and out, as if I were pooping, and the pain eased a bit. Encouraged by the slackening resistance, Danny bore on, sinking first one third then one half of his length inside me.
Oh god' I moaned that feels sooooo good', and that seemed to be the sign he was looking for as he then impaled me, sinking all the way. I felt his pubic hair against my cheeks and reached down to spread them so he could go deeper. He was in all the way now, pausing for a few seconds to let me adjust to him being there before withdrawing til his cockhead was again poised to come out. Before my stretched anal canal had a chance to shrink even marginally, he drove back in again like a piston, moving everything out of the way, stretching me and causing to gasp. I thought I would pass out, the feeling of him so completely inside me making my head spin.
`I'm going to cum' he gasped, and I felt him withdrawing.
No, no, no' I cried cum inside me. Fill me, I have to have you there'. And without another word he did just that. I felt the warmth before I felt the wet. It spread inside me like a heater had been turned on to slowly warm a room. My anal canal which had withstood the onslaught but still hurt was instantly soothed by the warm goo. Danny was still inside me, his cock jerking involuntarily as it emptied the last of his seed in my quickly filling cavity. His mouth came down on mine again, engulfing my lips as his tongue found it's way, once more, into my willing mouth.
Godamn' Danny exclaimed, that was terrific. You are one phenomenal piece of ass'.
`I'll bet you say that to all the trannies' I deadpanned.
`To tell you the truth, I haven't been with another tranny this way' he said seriously.
`You're kidding, how did you know about that place, this place?'
`Oh, I've been with other trannies, but only for a blowjob now and then. I mean I've never fucked a tranny before.'
`Oh I see' I was confused. Was Danny straight, bi, gay? I had no experience in this tranny thing, in over my head in other words. What type men and boys were attracted to sex with other men or boys who dressed and acted like girls? I sure had a lot to learn.
But not now.
Now I was, in truth, in a state of sexual stupor that I had not encountered before in my life. All the elements – the man, the place, the risk, my new `identity'- worked together to put me into an altered state of mind that has stayed with me to this day, and will til the end of my days. Gone was frustration. Gone was any stigma I may have realized or attached to my sexuality or way of life. All that was replaced by a feeling of serenity. A beginning. Some understanding that my life was to be defined in the future, not by what people called me, or thought of me, but instead by my desires. What I wanted. What I responded to. How I felt.
And right now, with this one encounter, my new identity had been validated as best as it could be. I didn't know exactly what a tranny was, other than what I had seen, but my long journey had begun that night.
To be continued...
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