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Image Credit: Picture purchased and licensed for use from

123rf.com. The model(s) in this image is in / and are no way connected with this story nor supports nor conveys the issues and situations brought up within the story. The model(s) use is solely used for the representation of looks of the main character(s) of this particular story. ~Sephrena

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Chapter 1
 
My name is Jack and I’m a street rat, a homeless person, in New York City (NYC); I live several levels below the street in an abandoned subway tunnel. During my four years in the city it has been used two times as a by-pass for a regular line that was receiving maintenance; the other time another area was closed because of an accident.

I had been in the city a few weeks when I followed four older guys using a door ‘marked caution: warning danger do not enter’. But they entered and a minute later so did I.

I waited to hear another door to open and close, but it took a while. Each level, I since learned, usually has four turns of stairs going down. I finally heard a door open and I started down. It is was a faint sound and caused me to wonder. When I went down and got to a door, I felt I got there too soon. The steps going down were roped off but footprints showed others had gone down there. I now followed though the descent wasn’t straight down. Exactly where I was, was not certain nor did it matter. The next door opened to a small landing and onto some tracks. Like the last section of steps the lighting was poor.

Pausing, I waited, listened and heard to my left the group was walking and I followed. Then I heard them speaking but no movement. I was watching in front and behind for the sound of a subway train. The subway trains were heard somewhere above us, none on these tracks. I’m using my smaller flashlight not wanting to shine too far down the track and give my coming away. Possibly I passed someone on the other side, two tracks over. It was wise not to search for trouble, so I kept walking.

I did pass spots I could run to and jump in case of an emergency. The voices of the group went silent and shortly after I was being approached by someone. I waited too long to turn back, two guys caught up to me. I should have been in for a beating, but lucked out. While I got a hit to the stomach that bent me over, they had use for a reliable centurion. I was tied so I could not run away once I agreed to help them as a lookout.

One of them showed me where I was to sleep. It was a cutout for subway track lights: green, yellow and red. I was told the lights could never be covered, but plywood or cardboard could be used to close off a two by four-foot section. I was to stay and sleep there but run up two sections further and warn the group before hiding myself there or near the third section. There was up to six in the group at times.

Over time I found two more ways in and out. There were several times each year I needed to warn the others and either hide or escape the tunnel. I was both fortunate and very good not to be caught by others in the tunnel.

On the streets, I was caught more than once, placed in group homes, with foster families or in juvenile centers. Never was I held more than a few weeks. Two times I was caught within an hour to six hours of having escaped. After my 8 or tenth time of being taken by authorities, their interest diminished.

There were many people, police included, who finally saw me as an incorrigible street person to ignore. More than a few people came to give me change or a dollar or more, encouraging me to stay clean and move along. From fetching water or supplies, or getting through small tight places for others I found many ways to provide for myself. Early morning was a good time to search for discarded clothes, food or other things I needed.

I used small spools of discarded wire, two lights and a switch that allowed me to place the lights 250’ away from my hideout as warning lights to my group farther down the track. Because the strands of wire were thin, they were easy to hide yet serve their purpose. I learned it from a so-called uncle. It was another plus for me with the group and had its perks.

I learned over time the importance of keeping myself clean and presentable to the public. Among other things girls and women had a higher repulsion to a grubby kid. Looking needy helped to evoke their caring and help. Being too dirty or pungent hurt, especially as I became interested in girls. My long hair was not detrimental, but too clean made the impression of an easy mark. Grungy hair caked together had way too many negatives.

Once, I was held long enough that a social worker got me a social security card which later enabled me to get a bank card. I liked newspapers and finding books here and there. I used a calculator to continue to learn arithmetic, discarded copies of the National Geographic maps to learn about the world, forgotten iPods and cell phones were good for music, communicating with others was not advised.

SIRIUS once held a concert that I got into at Central Park, and with a bit of fast-talking and good luck I got an iPod with a five year subscription. It was something few knew I had and no one knew where I kept it.

It was over a year ago I spotted a woman who caught my interest. I thought I had seen her before but finally, I followed her to where she lived. She wasn’t the first woman I took an interest in. She was considerably older, as I was now fourteen; I figured she was probably 23 or 24. She was not only beautiful but was educated and carried herself with class.

She lived in a good size apartment building of brick and stone. There were two apartments in the basement and I never figured out how many apartments in the remaining three floors. There was another woman with whom she seemed to share an apartment. Several men seemed to live there in the apartment complex but I was never sure which of them lived there or which were visiting.

Once I followed her to Fordham University where she attended classes. While she was sociable with others, she wasn’t dating anyone in particular nor did she seem to have many close friends. More than once she was picked up at her apartment by one corporate car or another. Some nights a guy in a fancy car or a limousine picked her up. Sometimes she ate at neighborhood cafes and restaurants, but most often at her place.

It was usually at least once a week that I tried to see her, while three times a week was the most I dared. It was unusual that we would be close enough to talk and rarely more than say hello. Once I was not paying close attention when she saw me near Fordham University and asked why I was over there. I told her I had to make a delivery, she asked what and I said it was a computer part, but that I didn’t know what. She frowned a bit when she asked where my bicycle was and I told her I didn’t have one.

Most the people who delivered things any distance rode the city streets on a bike. If you didn’t have a bike you were considered a neighborhood errand boy. I covered myself saying it was an unusual request and I did it as a favor and because I needed the money. When she smiled, I walked away feeling lucky to have visited with her, and was a good liar to get away. After that I knew enough to keep a good distance.

It was a few weeks later I was following her back toward her apartment and a couple of guys made fun of me for following her. Things would have been okay and I was handling things until one of them called her a whore. I am not naive to think she never had sex, but it just didn’t sit well that they called her a whore. I said she was no such thing and they should take it back.

I’m not a big guy and usually I would be smart enough to back off or get even another way. Today I wasn’t being very smart. I got in a good hit and knocked the guy down. Then it went from me fighting one to fighting three. They were bigger and I was on the wrong side for where I needed to go. I picked up a garbage lid and tried to charge though, but the fight escalated. Several cars were damaged, an older person was knocked down and hurt. By the time police got there, the others had run and I was having trouble picking myself off the sidewalk or street whichever it was.

The police in this precinct didn’t know me nor did they care. When I was dropped off to be processed as a juvenile, one officer noticed me. “Hey Jack, it has been a while. You know you could have picked a better time.”

That usually meant the juvenile courts were backed up or people in juvenile services were on the rag. It was a political summer which meant politicians were getting tough on crime, and by this time the courts and others were hard to get along with.

I got one day getting medical attention, unfortunately that meant 24 hours of people getting the wrong side of the story. Social services were called in and between the stories they were told and the broken record of my placements with them, things were not looking good. Everything broken and the person hurt were all credited to me. The person associated with me was unnamed; the label of her being a prostitute elevated me to a different level of crime and charges.

“You are lucky they didn’t find any drugs on you, but tackling the group you did, leaves little doubt that you are using something,” my caseworker said. While I admitted to it not being the smartest thing I ever did. I denied hurting the elderly person and admitted to only damaging one car.

I joked, “I hope you don’t hold it against me if they broke a side window with my face or dented a door with my head being driven into it by others.” They didn’t see any humor in what I said. They wanted me to acknowledge I was associated with a prostitute and to name her.

“If we identify the prostitute and have her come in, will she be able to validate your side of the story?”

“One, the person in question is not a prostitute; she was probably at least a block or more away and I don’t have a name to give you," I said.

The caseworker introduced herself as Valerie, but as we closed the session it was Ms. Jones and tomorrow was the deciding day for what laid ahead for me.

The next day I was shackled along with being cuffed before being transported. It did not bode well as good news. Ms. Jones and a female officer greeted me at the other end of my trip but we were meeting in a lounge. Ms. Jones said, “This will a be a very unusual meeting to determine where you will be staying next and which judge you would be appearing before.” With her nod, the officer invited in Dr. Roberts introduced as a clinical psychologist for the city and state. It was the next person who was invited in that caught me by total surprise.

It was the woman I was following the day I got in the fight and was arrested. She was calm, nicely dressed and gave me a slight but untelling smile. “Ms. Bridgette Riley has been asked to be here. She is said to be the woman you had been with prior to your fight and arrest Jack.” Ms. Jones continued, “Jack, we would like you to confirm for us you're knowing her and your relationship to her?”

“I’m a street person and on a rare occasion I take an interest in people I see. I usually don’t know them by name as in this case,” I said. “I stay away far enough that they usually don’t know I am there. Some time back she struck me as an attractive, educated, and classy lady, and I began to follow her now and then.”

“You are not the same age, so what was your intent? Are you a pervert, did you work for her or did you imagine her to be your girlfriend,” Dr. Roberts asked?

I said, “Neither as you said we are not the same age and I don’t work for anyone on a regular basis.”

“Miss Riley would you please tell us for the record your full name and what you do,” Ms. Jones snidely asked.

“My name is Bridgette Olivia Riley. I am a business consultant and I attend Fordham University seeking my Master’s degree in Business Management.”

“Have you been or are you now also involved in prostitution as has been insinuated by others,” Dr. Roberts asked?

“No, that is not true nor do I think you would have asked me here now if that were a serious allegation.” I liked how cool she was.

Dr. Roberts again spoke up, “That is very true and I would like to strongly advise Ms. Jones not to polarize this discussion. But you do know or have met Jack before, have you not? Did you know on the day in discussion that Jack got in a fight and that he was seen following you?”

“No, the last day I remember seeing and meeting Jack was about two weeks earlier near the Fordham University campus.”

“Jack would you please tell us what happened on the day you got into that fight and were arrested,” Dr. Roberts asked?

“As she said, it was about two weeks since we bumped into each other near Fordham. This was the 3 or 4th time I gone to see her since. I learned to keep my distance again. She had gone into her apartment building and I wasn’t sure what to do. I was walking the block before her apartment when some guy asked what I was doing following her. Then he made the mistake of calling her a ‘whore'. I pushed him saying it wasn’t nice and he should take it back. We both swung at each other and I got in a good hit that sent him back.”

“When two other guys stepped forward; I realized I was in trouble. I was in their neighborhood and I was on the wrong side of them. I didn’t want to go north that would take me close to her apartment. I was afraid she'd know I was following her. So I grabbed a garbage lid to help me work my way through and I rushed forward to get back to a subway tunnel. They knocked me down and kicked me but I made it up with my back to a car.

“One of the guys told me not to mess with the car or he would take it out of my hide. When he acknowledged it was his car. I smashed the outside mirror with the lid and the fight turned uglier. I should have gone down and stayed down that is when the elderly guy tried to stop the fight. They threw him down and out of the way and the fight continued. The next thing I remembered was trying to get up; the guys were running; then I heard the sirens and a couple of officers had me.”

They said, “Three cars were damaged and I hurt an old man.” I looked around and I was not where I had remembered and three cars were indeed damaged and I was bleeding and having trouble catching my breath as they gave me a good beating.

“So you’re saying you were a relatively innocent victim of circumstance,” Ms. Jones snidely commented. “You just happen to be the one arrested and charged.”

“No Ma’am, I’m not innocent, but I am the one out of that neighborhood and unknown to the police in that precinct. The others were able to run and by that time I was in no shape to run. I didn’t hit or hurt the elderly man, I don’t do that. And I didn’t damage the other two cars. I don’t take the blame for others, I just don’t do it. Nor is this woman a prostitute and if I had known her name I wouldn’t have told you anyway.”

Dr. Roberts was upset with the exchange between Jones and me. “We identified Miss. Riley as the woman in question and asked her to be here this morning. We need to decide how we are to proceed with you. In our system, you are considered incorrigible. We wanted to give her a chance to take responsibility for you without any charges made against her and possibly being dropped against you.

We asked Miss Riley here having told her what happened to see if she wanted to take responsibility for you. The other two choices as we told her are permanently putting you into a group home in lock-down or putting you over to juvenile court to face your charges. This being a political year, they want to waive your status as a juvenile and to try you as an adult with the charges upped to felony charges separated out so you could be facing some good time, 10-15 years.”

Miss Riley was asked to speak. “I would need to speak to Jack, but I am not expecting him or you to approve my alternative. I don’t think he is the violent, troublemaker people are making him out to be. The idea of him a fourteen year old being treated as an adult and thus placed in an adult prison is repulsive. But there is little I can do about it.”

Ms. Jones said, “Tell Jack what your option is? While it is unusual Dr. Roberts said it has been done with a troubled transgendered person, so it is possible.”

“I would not do it as something forced upon him, but if Jack was under my responsibility I would feminize him and she would live with me, go to school and do as I said. I would need to legally be her guardian and her identity formally changed to go along with the reality of how she would be raised. It would include more than appearance but how she lived and acted. Being fourteen I would expect her to go to school until she graduated from high school. I would need to speak with Jack alone and have his agreement without the threat of others.”

“Expecting he will turn me down, I will then leave this session and what happens after that would be your responsibility. I or someone I know of would speak up in concern for his rights, if he goes to trial,” she said.

Dr. Roberts spoke up indicating that an officer, Ms. Jones and she would leave the room and allow us to visit. She assured us that no one would be listening or watching save to make sure I did not seek to do escape or act violently. The officer unlocked my shackles and handcuffs. Dr. Roberts stated to Miss. Riley, “We have met your requirements, against our advice for your safety.”

“Jack, I need to ask and make sure for myself that you are not a stalker or under the allusion you and I have any romantic future? Who do you think I am and what is your interest in me,” she asked? She shook her head and asked, “How old do you think I am anyway?”

I opened a Pepsi in front of me and took a drink and rubbed my wrists and ankles as I took my time before I spoke. “No, I am not a stalker and I suspect you are 24 or 25, way too old for me. You are a good looking lady, your educated and you’re classy.”

“I’m a street rat, but I’m human not an animal. I work hard to learn and read, and years from now, I’m going to be off the street. I have people I look up to and want to be like. I’ve been on my own over four years. It would be at least two years before I can begin working my way off the street. I have a cop and a construction worker that I look up to as well as the likes of you. I got in a fight when someone called the cop Rogers a pig and wouldn’t shut his mouth. But I didn’t get in trouble for that like this.”

She said, “I’m Bridgette, and strangely enough I believe you. But what I am suggesting is real, though I don’t expect you to take me up on it. I’m sorry but I won’t deal with a young man. If you were under my care I would feminize you and you would become a young woman and have to go to school come September. You'd be under my care until you graduated from high school and were ready to be on your own.”

“You would have me cut and made into a woman?” I stepped back in shock, unconsciously covering my male parts.

She laughed then turned serious, “No, I would not seek anything done surgically to you. Your male parts would be hidden but otherwise untouched. I would expect you to dress and act like a woman including your attending school. I would ask you to be put on a hormone blocker and a light dose of female hormones to be taken ongoing. You would wear breast forms as appropriate for a girl your age. I won’t put up with arguments; you would have some say in how you dress as a girl fashion-wise.”

Bridgette was pretty sure I had heard enough and got up and asked the others to come back in. She had her purse and laptop in hand expecting to go. Ms. Jones was smiling, almost laughing as she asked, “So what do you think Jack do you want to take that option or can we let Miss Riley go?”

I looked down but didn’t answer. Dr. Roberts let some time pass, “Jack, are you seriously considering Miss Riley's suggestion or can we let her go and get on with business? This is your decision, but I need a formal response.” She waited and I looked at her and then at Bridgette.

“It may sound crazy, but it is the one thing I think I could handle. I am pretty sure lock-down in a group home isn't acceptable; I'm not an animal. My Dad gave up on me long ago, and I wouldn’t go back there anyway. I didn’t do so well against three bigger boys. So I'm sure a prison would be no better than living a nightmare.”

“You might be surprised, but I do know what a transgendered person is and I’m not one. But Miss Riley is open and honest, so I know what I would have to live with. I expect that she will turn me down when I say yes, but that is up to her. I see living as a girl as my only real option.”

The room went silent as Bridgette put down her stuff. Ms. Jones’ jaw fell and the officer and Dr. Roberts were just quiet. I do think the officer was ready for me to try to bolt. She moved and I believe she was going to tighten my shackles and handcuffs. Dr. Roberts signaled her to stop.

Dr. Roberts turned, “Miss Riley, he has said yes to taking up your offer; what do you say?” Miss Riley had a bag of stuff that she lifted and put onto the table.

“I didn’t expect it, but I have prepared things just in case he said yes. There are clothes in the bag and a note of what she would need to do now so you people know upfront what I am doing. You need either say no now or I follow through with what I said. Ms. Jones said there would be a unisex restroom that could be used by Jack.”

She pushed over to me a bag; I took it with me as the officer showed me the restroom. I was given another bag for the clothes I was wearing. I stripped down and put my clothes into that bag. There was a page of instructions at the top of the other bag. I found a pink panty and stepped into it and pulled it up my legs. It was different as I tucked my boy self back between my legs, bringing the panty up in place.

There was a bra with rolled-up sock for each cup. I tried putting them on all together and finally decided to put on the bra and then put in the socks. The bra had nice lacework around the cups, along with the straps as well as the bottom of the bra. The white item was a pullover blouse with pink trim and short puffy sleeves. I put it on and smoothed it out, my chest appeared to have soft bumps with a V opening around the neck. I noticed my arms and hands were shinny when I washed my hands very well. They weren’t big but they weren’t a girl’s. I felt frustrated.

There was a nicely folded pair of red slacks that snuggled my legs and body as I pulled them up. I was sure they won’t fit and would rip when I bent down or moved the wrong way. But I realized that was the style. Bridgette wanted me to sense that they and I were different. I found some stockings but they were anklets and had gone up far enough to give the appearance that I was wearing stockings.

There was a pair of shoes with a two-inch, narrow heels. There was a pouch at the bottom of the bag with a brush, lipstick and mascara. I got frustrated and loud with the brush and trying to make something of my hair. Dr. Roberts knocked at the door and asked, “Are you dressed enough I can help you finish up.” I should be embarrassed but said yes and she came into the bathroom.

“You have done well; I heard your frustration and gathered it was either makeup or your hair. She took the brush and brushed out my hair from the mess I made and then began to style it. It was simple, nothing elaborate, yet it helped to transform my look to that of a teenage girl. I did the lipstick and grabbed the mascara brush, but I was having trouble to move my hands right to apply the mascara, until Dr. Roberts spoke. I was going to give her the brush but she said I could do it and she guided me as I was looking into the mirror. She suggested how to hold the mascara stick and turn the wand ever so slightly as I approached the lashes. I got the lashes in close to my nose as well as a light touch on the lashes along the bottom of my eyes.

When I stepped back I was happy with my eyelashes and hair but my lips looked like someone pushed on the lipstick. I wiped them off saying I was done, but Dr. Roberts said I could do it with a little pointer. She was right and I liked the look of my lips glimmering with lipstick. I couldn’t believe what I was thinking. I hoped I didn’t say it out loud.

“Yes, you did quite well with a little help; I suspect in a few months you will be amazed with the look you can put together. Now I think you are ready to step out and we can finish things up and you two can get going,” said Dr. Roberts. She took time to speak to me and asked me to try and stay out of trouble. She gave me her card and invited me to call if things got out of hand. It would be six months before my record would be cleared.

Two women stepped out of the rest room and I handed my bag of clothes to Bridgette. She held out two hands like women sometimes do. I took hold and it comforted me. This time I sat down next to Bridgette with a big unbelievable smile on my face. Dr. Roberts asked for a name. Bridgette spoke up, “Ashley Phoenix Riley will be her name unless she protests too much.”

I quietly said it to myself, 'Ashley Phoenix Riley,' "I like Ashley and Riley means you are accepting me into your family which I like. I haven’t belonged anyplace for quite a while. I will probably make you sorry that you gave it to me. But why Phoenix as my middle name?”

Seemingly the others figured it out, “Hopefully it fits and is becoming of you.”

Ms. Jones felt a need to remind me I could soon be hers again, “I look forward to seeing you back and turning you over to the adult courts. Your role then as a girl there would be very uncomfortable for you.” She laughed at me.

Dr. Roberts said, “Ms. Jones seemingly your supervisors either like or put up with your attitude. But I am putting in a recommendation that you do not work with juveniles any more. I am also putting an injunction against you having anything to do anything with Ashley or her case. It will place you on the edge of being out on the streets, let’s see if that impacts your sensitivity.” She dismissed us, and Bridgette handed me a purse as we left.

The purse has a long strap that I placed over my shoulder as she gave me the bag and her laptop to carry. Walking out and down the steps made me think of how I was walking; Bridgette suggested smaller steps. I made them narrow with one foot in front of the other but worked to limit any wiggle in my walk.

She signaled for a cab and instructed me how to sit down and move over. She gave the driver an address and was on the phone calling a friend, Cathy. “We are on our way over. She surprised all of us and she’s coming over for your help.” They talked a bit more as she looked at me with a smile and motioned me to check my purse. I was looking into the purse of a woman but it was neat and organized like a girl owned it.

Before we pulled away the officer ran over to the taxi and handed a card through the window. Bridgette handed it to me. It was a driver’s license marked ‘Identification only’. There were my picture and name as Ashley Phoenix Riley. I found a wallet with a change purse and a place for my identification along with a place for a phone with an I.O.U for a new phone.

We were on our way. I knew where Bridgette lived, but I wasn’t sure of anything else. A confused look must have gone on my face. Bridgette leaned over and gave me one of those women kisses on the cheek, saying “Welcome to Oz Sweetie.”
 
 
To Be Continued...