A Learning Experience Ch. 07

Nis 15, 2024 // By:analsex // No Comment

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My father had disowned me in June of 1975, and my psychiatrist had apparently decided I was just too much to deal with, insisting I never appreciated his help during my transition. Because those two people provided so many links in my previous life, I felt I needed to leave them behind and move on with what was left of ‘my life’ if there was such a thing. I certainly was feeling sorry for myself, but it also went deeper than that, because I needed as much support as I could get right at this particular time. I was attempting to change my gender, never an easy thing under the most ideal conditions. Yet I never seemed to have anything close to ‘ideal conditions’, instead… I was now preparing to prove myself in the only way I could. And if the only way I could was to exploit my body for money, so be it.

As a side note, Philly Street Speak, at that time, was raucous and frequently bigoted in its content, although not in it’s meaning. It really meant nothing to be called a name that I simply would never think of using today, as it would be considered highly inflammatory. This may be difficult to understand, but it’s another reason why these chapters have been so hard to write. To try and take the words for what they were, without understanding the environment, would make this seem volatile to some, perhaps even traumatic to others. Therefore where direct dialog is required, I have heavily modified it to keep the more extreme forms of words used in our daily discussions, out of the dialog as much as possible. I know I am sacrificing reality, but words can hurt when used without consideration of other’s feelings, and I don’t believe it will help give you any better insight into what my life was really like. Instead I think the pain these words might inflict, makes me want to try anything to avoid it.

I think the ending of this chapter may need some explanation as it involves such intense and even brutal actions. But I felt forced into doing everything I did that day. In the city section of the Sunday Philadelphia Inquirer, the story that described this incident said, because the location was known for mob-sanctioned gambling… that this violence had to be part of the ongoing internal war happening within the Mafia at that time. Once you’ve read this chapter, you’ll know the real story and how it all actually happened. I hope that my gentle readers will try to understand… this was a violent and dangerous moment in my life… but only a moment.

To my muse & soulmate Griffin57, my love is yours Always & Forever.

I had been ‘working’ a particular area of old Philadelphia called the ‘blue zone’ or ‘blue district’ for its inclusion in the cities old ‘blue’ laws allowing stores to be open on Sundays and religious holidays. This included an area roughly encompassing the courthouse on one corner, Broadway and South Street, another. Then down to Front Street, basically everything east of Rittenhouse Square to the Delaware River, approximately a 10 by 14 city block area.

By walking through the area at around the same time everyday, I gave my regular customers an idea of exactly when they might expect me, and I tried to make sure it never varied. I would start at the courthouse around 1pm and down Market through Independence Square, back up Chestnut, then down Sansom. Then a zigzag route up and down Walnut, Locust, Spruce, Pine, Lombard and finally back up South Street and over to Broad Street, back to Suburban Station and I was usually home before midnight.

The traffic flow of the streets, even the street names themselves, have changed over the years, but if you are from Philly, you know I’m walking against traffic. What I found out the hard way was that vice cops are very good at sneaking up in their cars from behind you, with the traffic, always watching for any illegal acts you may be considering. Fortunately it was a rookie that spotted me in this way first. Once he decided to ‘take me down’, I had yet to actually finish my ‘turn’ and therefore had not yet received any money for my efforts. In this case, a very handsome young cabbie that had me take him orally right in his front seat. But without any exchange of cash, we might as well have been playing checkers in his cab.

There were any number of phrases I had to re-learn as I wandered through the blue district, mostly that were commonly (and incorrectly) used on TV and in movies, such as a ‘trick’. The term ‘trick’ is a base term for the customer, to the independent streetwalker, a sex act transaction was known as a ‘turn’. To ‘turn a trick’ meant performing a sex act with a customer. But the whole concept of a customer was almost irrelevant and therefore the only term we ever really used was ‘turn’. So you might hear someone say ‘Got tons of hi class turns down on the Wash today!’

When a ‘trick’ or ‘john’ was mentioned, it was rare, and usually only as a warning for their deviant or forced sex behavior. Height, weight, skin color, hair color, facial hair, scars or tattoos, and finally their sex organ would describe them. You’ll have to take my word for it, once these items were known about you, you’re name just didn’t matter! If you hurt a girl, you could ask for sex erzurum escort until you turned blue and we would all simply ignore you as if you weren’t there… if we were alone. If we were with another girl, a simple two finger sign, and I might keep you entertained while the girl I signaled called the cops. Tricks that hurt girls could also end up on the wrong side of their pimps, but that was rare, we always looked after our own on the street, we were all we had.

Later on I would run into other transgendered streetwalkers. Even then, and this must just seem as incredible to you gentle reader, as it does to me writing this all these years later. We were VERY careful about who we told about our gender ‘issues’, because even other transgendered might give you up, and once you were ‘read’ or ‘clocked’, living on the street became a very different and unpleasant experience.

It took me a while to learn some of the ‘basics’ from the girls that had been out here a while. After a few bad confrontations on the street, I learned my ‘competition’ actually considered me family once they saw me working as hard as they did. As long as I made contact in one of the many ‘neutral zones’ such as diners, Denny’s and other eating establishments, and bought them dinner, we could become fast friends, and I did actually make a couple close friends this way.

As far as being ‘read’ by genetic females, I managed to pass with a little bit of attitude thrown in, because most women, even if they ‘thought’ they knew, would rarely attack and try to show you to others. My worst enemy here was the experienced male Pimp, who would not think twice about pulling your skirt and revealing all if he thought you were Trans. For no other reason than pure spite, these monsters were sociopaths and loved to be as sadistic as they could manage, and they managed it well. A run-in with one of these nearly cost me my life. But I’ll explain that in just a bit.

There were nights that I worked overtime. Always on the weekends, when I wouldn’t jeopardize my job at the garage, and the most Tricks were available. I had been living on the Philly streets for almost two months that summer of 1975 and had learned most lessons pretty well. If I didn’t have an ‘appointment’ I’d stay at a friend’s place for the night or go looking for a party where I could find a hook up. The shelters were good for a shower and something to eat. I’d duck in for the morning then I’d be out hustling again. There was something new going on with the shelters though, something aimed directly at anyone promoting sex through sodomy, especially transsexuals and I’ll explain that in much more detail later on as well.

I met three other transgendered streetwalkers during this time, and we tended to work together when we could. We called ourselves ‘stray cats’ since no one wanted us, even as we were, and once they knew we were trans, even less. As trans often tended to do, we formed ourselves into a support group to provide each other some small feeling of family and community in a world that had consistently denied it to us in every other way we had ever sought it. We would have killed for each other, our bonds were hard as steel, despite our outward appearances as feminine girls, we would take on anyone that attacked any of us.

Kelsey was a big boned midwestern girl, and she transitioned early, but even so was five foot eleven in her stocking feet. She had beautiful legs that just went on forever. Other than her height, she passed well, with dark brunette hair, and a very pretty face, long neck and the same well-sized hands and feet as I did. Her father was in the Marines, and expected his son to follow him. Funny how that works, but the Marines just don’t have much interest in high heels and skirts, so Kelly knew it wasn’t going to be working out well.

Her mother understood that, from an early age, Kelly was never going to be the man her husband was expecting. It was a typically depressing story, the father came home from a long tour on an aircraft carrier to find his son in skirts, blamed the mother and beat her senseless. Kelly escaped, and after several miracles was helped just enough to make it on the street. Kelly eventually transitioned to Kelsey and has lived in Philly ever since.

Simone was petite, just barely over the five-foot mark, and this alone allowed her to pass easily. She always had her hair dyed a fiery red color, which complemented her light complexion. Curves for days, what estrogen did for that girl should really be documented someplace, because she was simply gorgeous. We never knew much about her past, although she obviously had oriental genes in her background. One night when we had all gone to a nightclub to relax, she revealed that her parents were both from Korea, and her real name was Sim Hong Yul, which she ‘Americanized’ as well as feminized into Simone. She was pretty drunk by the time we got home, and when we got her undressed, we all saw several terrible scars on her back, which she had somehow managed to hide until then. Simone nonchalantly explained them away as the excesses of her father-in-law. I had nightmares for days after seeing them, they were that bad. ghpops.com She was terribly embarrassed the next day, and we all promised to never speak of it again for her.

Charlene was a striking African-American girl, very tall at six foot and an inch. She had to be a little careful with heels or she ended up towering over her Tricks. Actually some of them liked that, but Charlene was hardly Dominant. I believe she would have been considered developmentally challenged today, but back then… well, it took our best efforts to keep her out of trouble… lets put it that way. She knew how to take care of herself, if nothing else, her Afro was always immaculate, and we would all fight over which of us she would help with our nails. Charlene just knew beauty the way others know how to breathe… it came so very, very naturally to her.

But her past was a little unusual, Charlene’s parents were killed in a car accident and she grew up with her grandparents in South Philly. Her grandmother saw ‘Charlie’ wasn’t growing up as the grandson she had expected and tried very hard to get her into the proper programs that could help. But those were few and far between, and rarely available to someone of such limited means. Charlene’s grandmother eventually fell ill with terminal cancer and sent Charlene to live with an uncle that was close by.

I had actually talked to her grandmother, once when Charlene asked me to help her take a little table she bought for her Nana’s birthday, over to their house. Her grandmother told me that when she had a temporary remission, and got out of the hospital, Charlene simply appeared next to her bed one day, and begged her to never send her away again. The grandmother said she could never get the uncle to explain what happened, but that Charlene would simply weep if she was pressed about it. She also told me Charlene was now on the deed to the little row house she owned, and in her will so that she would always have her own place. In the most emotional scene I’ve ever lived through, this dying woman asked me to watch over her granddaughter for her. And on behalf of the ‘stray cats’, I agreed. To this day we send Christmas cards and talk when we can. Charlene still lives in that South Philly row house with her husband and an adopted daughter. I would bet you anything that daughter is the prettiest girl on the block.

As Smitty said that night that seemed to have happened so long ago… I was a protector, and I took to the role of group leader and protector as soon as I met Kelsey, who looked up to me as a big sister for years after our first meeting. The role did something else… it started rebuilding a very fragile ego and gave me a new start, once again believing in myself simply as another human being. I actually began thinking about the friends I’d left behind too, and dealing with pains… hard to explain even today. Yet I would see those friends in dreams… searching… they wouldn’t be really though… would they?

Early in the first week of August, I’d made contact with a drug dealer willing to sell us the drugs we all needed, estrogen and testosterone blockers to continue our Hormone Replacement Therapies. However, this drug dealer saw me as a good ‘mark’ and attempted to rob me of the money I had brought to our meeting for purchasing the drugs I’d asked for. If it was only for me, I’d have let it go, as there were plenty of dealers. But I felt responsible to the three other women in our group, and his .25cal revolver didn’t have the intimidation factor I guess he thought it should, especially since I was nothing but a ‘faggot in skirts’ (his words). But this skirt had a solid six years of Tae Kwon Do training and he found himself on the ground watching me unload the 8 shells from his revolver’s cylinder. I did not rob him, and threw the empty revolver on the ground next to him while I walked away… as I said there were other dealers. But the city streets were a network of their own, and what I never realized was his association with much more powerful people. Turned out that his boss was an established Pimp, trying to break into drug dealing as a sideline and was not happy that I had roughed up one of his dealers. This set the stage for the scenario I describe next.


On this hot & muggy Saturday morning in August, I was visiting one of my most important clients, Miles Rueben Rosenberg. I called him Miles Standish because he reminded me of the pictures of puritans I saw in high school history class. He was also actually part of THAT family of Rosenbergs, the same family that played real life monopoly with some of the biggest pieces of real estate in New York, New Jersey, and Pennsylvania. But Miles had some sort of clerical position with one of their attorney firms that managed real estate transactions for the family. He did his work and then went home, and from what anyone could tell, he didn’t do much else… unless you worked the kinds of places the ‘cats’ worked.

Its hard to explain what all I did while selling my services for my client’s sexual needs. I’m sure people come up with their own ideas of what my days as a streetwalker were like, some exciting no doubt. But most of my clients were like Miles… depressed and fairly morose people that I would do things for that no one else in the whole world wanted to do. Because Miles did everything he could to punish himself, and the keyword there was ‘self’. He performed self-bondage, self-flagellation, and self-humiliation in more ways than most people could possibly imagine. He had been hospitalized many times and nearly succeeded in killing himself during a couple of those incidents. His doctors had managed to get him a little better balanced with various drugs, but he always ended up back on the street looking for submissive sex.

One day Miles found Charlene, and she agreed to come back to his apartment and have sex, but it quickly got beyond anything she’d experienced. Right in the middle of their session, Miles started begging her to cane him, and Charlene just couldn’t handle it. At first Miles was upset, but then just as quickly became enamored with Charlene, who tended to have that calming effect on people. She explained that she knew of a Dominant streetwalker, who he might be able to hire under the conditions he required. Which brought me into this charming little nightmare. After a long meeting that detailed what he needed me to do, and the money I would need to do it, we set up a Saturday session every week. My limited training under the Sisterhood’s guidance served me well, and I knew I would be able to give Miles the release he needed, and of course the money I needed.

But before I would agree, HE had to agree to a few extra steps. Anyone with even preliminary experience with real S&M practices understands the importance of a three-letter acronym called SSC, or Safe, Sane, and Consensual. The first two terms are straightforward enough, the last means nothing should happen within a session that has not already been discussed and agreed upon with all parties involved. And the first item we had to agree on was a safe-word. We made it the color red, and if he said this safe-word, the session would end and I would leave. In the case where speaking was not possible, jerking the right leg twice in a row would cause me to ask him if he was using the safe-word, and if the response was positive, the same result would occur.

I told him that when he safe-worded, he would not see me again, in order to make sure I really had crossed a boundary with him. In reality, I would call once again to discover why he safe-worded and if there was something we could alter to allow him a better level of comfort in our sessions. I’m not a monster, but I am a Dom, and a good Dom ‘pushes’ their subs to better discover their limits. However with someone like Miles, I was actually afraid to know what his limits might be. So in this case, defining his limits was every bit as important as my own, giving me a better feeling that I could maintain control, and in S&M, control is everything. Once our limits had been reviewed and accepted, I let drop my ‘special’ attribute, just to make sure it was okay with him, and as I expected he was delighted.

Once Miles knew I was a pre-op transsexual he thought it would be a wonderful addition to his overall ‘humiliation’, to have forced anal sex with a transgender woman, which was enough to trigger my anger, and get all my ‘Dom’ juices going. But I finally decided I would use this as a test case, if I could get Miles to see I was nothing more than a girl with a little something extra, maybe I could convince others. That particular morning I walked up the small landing in front of his Rittenhouse Square apartment, found the key in the usual spot and let myself in.

He was tied to his bed, which was the position I usually found him in, a ball gag and blindfold finished the bedroom apparel… in other words… he was naked. Surprisingly, or perhaps it shouldn’t really be surprising, Miles maintained a good regime of diet and exercise and he was actually quite a good-looking 24-year old man. About five feet ten inches tall, and 180 pounds, he had washboard abs to die for. Not really one of my ‘body favs’ but they WERE impressive, he also had beautifully well toned skin with brown hair, and puppy-dog brown eyes. I gave out a long sigh, as I usually did when I first laid eyes on him. I could no more hurt this boy as murder a kitten, but that’s what I was hired for, and that would have to happen… but on MY terms… not his.

Despite the family background and last name, Miles had been born to a very strict catholic mother and had just been given his first communion the day of a terrible fire that took his Mother and Father’s life. I never was able to get him to tell me much more about this horrible event. However, part of his reaction was to renounce God, and just a quick look around the bedroom showed many hidden satanic symbols drawn on his bedroom walls or arranged with toothpicks. Miles grunted now, letting me know he was awake and heard me. I went to the kitchen and got a cold glass of water and a dishtowel, then returned and unbuckled his gag. I then carefully poured water over his lips and mouth, catching it in the towel, as I slowly pulled the gag out of his mouth. I took out my switchblade knife and opened it next to his right wrist. The loud clack caught his attention and produced a quick gasp, as I slid its razor sharp blade under the clothesline he’d used in a slipknot to tie himself to the bedposts.

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