Debt           by: Janet L. Stickney                       JanetLynn17@Hotmail.com

 

As my mouth opened to take him, I was literally eye to eye with it, yet my tongue flickered out, and for the first time I touched a man in a way that not many men would do for another man. I felt his hand on the back of my head, gently pushing, opened my mouth again, and with a single plunge, took him.

Reckless and carefree, I had gained a taste for betting, often gambling more than I could afford, winning just enough to almost cover my debts and stay in the good graces of my bookie. My luck went sour, and with a string of eight bad bets, all made on the same day, I found myself tens of thousands of dollars in debt, debt I had no hope of paying off…ever. But I was sure that at the age of 15 I was safe. As a minor, no bookie in town should have taken my bets. It was my only hope. Mom worked as a waitress at some high class restaurant, dad was nowhere to be found, so we didn't have the kind of money it would take to get me out of the jam I was in. When I mentioned it to my bookie, he was all smiles and sounded very kind and understanding, then he told me, in very clear terms, that age didn't have anything to do with it. I owed the money, and unless I could pay the tab, he would find a way for me to work it off. Assuming he was going to have me run numbers of something, I said "okay" then left. But I knew that he was going to make me pay the money, one way or another, and with the interest rates he charged, I would never get out, no matter how hard I worked.

The minute I got home I stripped and jumped in the shower. What I had not told my bookie was that I had an alternate, someone I could become, someone that he would never find. See, I had been dressing up in my mom's clothes for as long as I can remember, and I thought I was good enough to go out, and had actually tried it a few times. I quickly changed clothes, knowing that I would have no choice but to tell mom what was going on, and the reason she was about to have a daughter rather than a son. I wore the nice straight skirt, the green one, with a simple white blouse and low heels, my hair done in a ponytail. My makeup was perfect, and just as I put on the earrings, I heard the door open, and mom call out my name. Believe me, I didn't want mom to see me this way, but it was either this, or end up dead. With a deep breath, I opened the bedroom door and walked out. Mom took one look and stopped dead in her tracks.

"What's going on here Kevin? Why on earth are you dressed like that?"

"Mom…I had too…"

"I knew you were into my things a few times, but I never expected to see this! What does that mean, you have to?"

I sat down, with mom staring at me, and told her the whole story, how much I owed, then, about the times I had been out as a girl, which is why I didn't think my bookie could find me. If I remained a girl, he would never know, and I would be safe! Mom listened without interrupting, then sat back. She did not look happy. Her eyes changed from wide open to thin slits, her mouth became a mere slash of red, her fists were balled up, and I knew she was more angry than I had ever seen her before. Finally…

"Just how stupid do you think these men are? They know everything about you, including where you live! If they see you coming and going, do you think they can't figure it out? How could you be so stupid!?"

There wasn't anything to say, so I sat there silently hoping mom would know what to do, but by the look on her face, I might have been better off with my bookie. Just then the doorbell rang, and mom opened the front door, and there he was, my bookie! He could not miss me sitting there, all dressed up, and there probably wasn't any doubt who I was. Mom let him in, then he sat without being asked. Facing us, he didn't seem all that tough, but…

"The kid owes us a lot of money, and I'm here to see how he plans on paying it back."

"But he's only 15!" mom said, "How can he possibly pay you that much money? If he doesn't what'll you do? Hurt him? Kill him?"

"Nah! I can't collect from a dead man, and if we break him up, all that does is bring the cops down on me." He looked at me from head to toe, the grinned at me. "You know, I can use someone, a girl that can work out front, serving drinks and so on, I'll pay $500 a week, with $300 coming back to me. She could keep all the tips. I figure, if we cut the interest, she would be all paid up by the time she's…what? 23? Other wise, I have to demand payment, right now. Those are the terms kid, take it or leave it."

"But…but…" mom sputtered, "he has school! He's a minor! He can't serve drinks!"

"I checked Madam, the kid attends school in the morning, and I don't even open until two, so it works out. As far as serving drinks…well, lets just say it won't be a problem." Turning to me…"What'll it be kid?"

I looked at mom, saw the sadness that filled her eyes, then back at the bookie. He knew what the answer would be, it was the only answer. I nodded my head yes, as he stood up to go, mom asked him if he was going to supply any kind of uniform for me to wear, or would casual clothes be enough. He looked at me, then back at mom, opened his jacket, peeled off several hundred dollar bills and gave them to mom, telling her that casual would be okay, but added that he wanted to see me in skirts, not slacks, and the money was a small advance so she could get me what I would need, but the money would be added to my debt. I had briefly considered going to the cops, but everyone knew that they were on the payroll so to speak, and all that telling them would do is get me busted up. He left, mom and I stared at each other, then she suddenly stood up.

"You've certainly done it now!" mom said angrily, "how could you bet so much money?! Do you have any idea what this is going to mean? With school in the morning, you'll have to come home, change clothes, and look perfect as a girl every time by the way, then work who knows how many hours! You'll have to do this day after day, every day, until you graduate! Maybe then you could dress as a girl full time, but for now, your life just hit the trashcan, and there isn't anything I can do except help you become a girl! And just how do I explain this to the rest of the family? Your grandfather is going to have a cow when he finds out, and what about your friends?"

Mom was right. My life went right in the can the minute I lost, and having my bookie see me dressed as a girl was almost as bad. But, he did offer to let me pay off the debt, the only hitch was that I had to do it as a girl, and like mom said, that was going to lead to some serious consequences.

"Since you're already dressed, we might as well get you some more clothes, you can get more as you get paid, but for now you'll need some items that I don't think we can get at the mart. Grab your purse, and lets go."

Since it wasn't a question, I did what mom told me, taking my empty purse in my hand and following her out of the house and to the car. Most of the money was spent on breast forms, good ones that could be glued on, for when I worked the weekends, a padded pantybrief, then a couple of bras, a few skirts and blouses, pantyhose and shoes. With each purchase my anger at how stupid I had been grew, which was not helped by the look on mom's face. I truly believe that if she had the chance, she would have killed me. Between us, shopping was not a fun experience, but when we left the mall, mom said that I had enough clothes to start with, then informed me that I would have to buy whatever else I needed with the few bucks the bookie gave me. I saw a few of my friends at the mall, but didn't make any effort to let them know about the predicament I was in. I was, in a word, ashamed.

When we got home, mom told me to put everything away, then left the house. I had plenty of time to consider my options, which amounted to zip. No matter where I went, what I did, they would find me, cause me great pain, and I would still owe the money. As I put the bras, pantyhose, slips and panties in one drawer, the skirts, blouses and shoes in the closet, I glanced out the window and saw several girls my age. Soft and pretty, they gave no sign that being a girl was something to avoid. I saw myself in the mirror, my reflection that of a girl the same age as those outside, and sighed. I looked enough like a girl to get by at the mall, but I knew that I didn't walk, act, or talk like a girl my age. I lacked the naturally fluid grace girls have, I had no idea how to do my hair let alone makeup, and only a cursory knowledge of what to wear and when. In short, I was a guy in a dress, wearing makeup and a padded bra. I sat on my bed and cried tears that just would not stop.

My carefully crafted image of a somewhat tough guy that made his money betting had been shattered to pieces, reducing me to next to nothing, while at the same time my secret, hidden so carefully for so long, threatened to be exposed. Tough guy and soft girl, the two sides of my personality, had never come in conflict before, because dressing up as a girl was, for me, a very private thing. I heard the door open, then footsteps, but stayed in my room, unable to face my mother dressed this way once again. Shut in my room I felt safe, the familiarity of it granting a sense of security that I craved right then. When the door opened I expected my mother to walk in, but it wasn't. It was my Grandmother, closely followed by my Grandfather. There wasn't any doubt about the way I looked, I still wore the skirt, blouse, and the remains of my makeup, surely streaked. In other words, I looked like I felt.

My Grandmother sat on the bed next to me, and when I broke out crying again, she held me in her arms. Then…

"I went" Grandpa said, "and talked to that bookie. He said he understands your problem, but he did the best for you that he could. He said that he couldn't simply write it off as a bad debt, because, in his words, there wasn't any such thing, only difficult to pay debts. I did manage to get you one day off, Sunday, and he also agreed that graduating from school comes first, but he was adamant that you will work in his shop, six days a week, and you'll do it as a girl. According to him, he has had some success curing other boys with gambling addictions the same way. He said that if you had a big test, a special dance or something like that, he would be flexible enough to make sure that you got the time you needed. So, it looks like you'll be working as a waitress whether any of us like it or not!"

I looked up at him and saw the disappointment on his face, which crushed me. My dad had been a drinker, and was killed when he ran off the road. I was about two at the time. Now my grandparents had to face this. Yes, I liked to dress as a girl. Yes, I had gone out a few times dressed up, but never during the day, and I had never been found out. Now all that didn't matter, I was going to work as a girl, and everyone that meant anything to me knew why. There was nothing I could say, so I didn't. I just let grandma hold me. Grandpa left, shutting the door behind him.

"He blames himself honey. He thinks that if he had been here for you more often…"

"Grandma, he was here! I just thought…I was doing so well that I…"

"What you did was bet more than you could afford, with a man that doesn't care about you. Now, lets talk about this. Your mother says that when she came home you were all dressed up, and by her accounts, didn't look to bad. Was that the first time you had ever dressed up as a girl? Or was it just dumb luck that you got it right?"

"I…I…" Grandma has piercing blue eyes, the kind that drill holes in you, eyes that had never let me lie to her before, but I tried. "I…maybe…"

"So" she said, "you have dressed as a girl in the past! Your mother just cannot handle all of the turmoil caused by this. She doesn't think she is able make sure that you look like a girl every time you have to go to that place. She hates the idea of you having to wear women's clothing, and that attitude is not going to help you…is it?"

"No, I guess not" I said, wondering what she was trying to tell me. "Your mother thinks she is at fault. She thinks that if she had spent more time with you that none of this would have happened, which is nonsense of course, but, because she thinks she has failed you, she just can't bring herself to help you "degrade yourself anymore" as she puts it. That's why we are taking you to live with us. I have the time to help you become the girl you need to be, and your grandpa will make sure that nobody hurts you. We'll drive you back and forth to school for the next week, until the winter break, then you can transfer to a school closer to us. We will also take you back and forth to work, which will let us make sure your safe."

"Grandma I…"

"You pack up" she said, "I'll be back later today to get you, and by the way, don't change."

I heard my grandparents leave the house, then a few minutes later, my mom walked into my room. We traded looks, then she started crying. My mom doesn't cry…ever, yet the tears were very real.

"I didn't want this for you Kevin! I should have been here for you, I wasn't, and now look at you!"

I said the first thing that came to my mind, which turned out to be the right thing. "Mom, you're a girl, right? You turned out alright, Grandma made sure of that. What happened is all my fault, and there wasn't anything you could have done to change it. I admit that I like to dress up as a girl every now and then, and maybe I even thought about being a girl full time, but the problem isn't me dressing as a girl, it's the fact that I owe so much money! My dressing up as a girl was fun, only now I have to do it! Mom, this is my chance to get even with the bookie, and dressing as a girl isn't going to be that bad, plus, with Grandma watching how I do things, I should turn out just as nice a girl as you are! It was always about me mom, not what you did or didn't do for me."

"It's just" mom said, "that I never expected my son to like being a girl! Your father was a drunken bum, and I didn't want you to turn out like he did, so I guess I didn't pay attention to what else was going on around here, and that's why I never realized what you were doing. Dressing as a girl is one thing, but betting so much money is what brought this all on. I just hope that you don't ever go back to gambling ever again."

"Don't worry mom, I won't have the time, and I certainly don't want to be killed! I'll try to be as good a girl that I can be."

Mom and I packed up everything, and when Grandpa returned with the truck, I was ready to go. Mom and I hugged, and I left, still wearing the same skirt and blouse. Once I was settled into my room, grandma came in, and we talked some more, which is when she laid out what she had in mind.

"Your grandpa and I talked about this situation for a long time Kevin, and we have decided that after you change schools, we think it would be best if you just kept dressing as a girl, full time. All that changing back and forth is going to be very hard on everyone, especially you, and I'm convinced that with some help, you'll be able to attend school as a girl easily, and since you only go half a day, you won't have as much exposure as someone who went to school all day. That said, you and I are taking the whole day tomorrow, and we will get you a wider wardrobe, some better makeup, then we'll see about finding the things you'll need to present yourself as a girl without any problem. Dinner will be in a few minutes, so you go get washed up."

Grandma left me speechless! That would mean that within a week I would be dressing as a girl full time! I had serious doubts that I could do that, but she didn't sound like she was asking, in fact, it sounded like she told me what was going to happen. Whether I thought I could do it or not, I knew from past experience that all arguing with grandma got you was tired, because I never knew anyone to get her to change her mind, including grandpa! Looking in the small mirror I saw that my makeup was starting to give way, a bad sign of course, but I had had a rough day. I washed up, then helped set the table. Over dinner, grandpa asked me what they should call me, since "Kevin seems a little to masculine when you look like that" he said. I told them I liked to be called Diane. From that moment on, that's the only name either of them used when they talked to, or about me. Just hearing it was strange, but my entire life had just dropped into the twilight zone, leaving me only to wonder about my future.

Grandma was, if nothing else, thorough. She had me standing in her sewing room, naked except for the thin white panties, taking measurements. Then she consulted a big catalogue, arriving at the proper size for me, from bra size to shoes. She also figured out how big my hips and breasts had to be as well as how small my waist needed to be for me to present myself as a normal girl. She did not talk much, clearly focused on the task at hand instead. When her list was done, she told me to get dressed, which I did, including a modest bit of makeup. Then it was off to the stores, starting at a shop that sold breast forms. By the time we got home, I was wearing the new breast forms, and my hips were padded to give me a better shape. I dragged all of the bags to my room, put things away, then sat on the bed wondering how I could be so stupid to get myself into this mess.

I began to dress every day, getting better at it I guess, then I reported to the bookie, dressed as a girl. He didn't bat an eye as he gave me an order book, a tray, and told me to get busy. The deal was that I could keep the tips, and as the day went on I began to see that many of the guys there would tip well if they did well, less or nothing, if they lost. At the end of the first day I had about $200 in tips! Grandpa picked me up, we went home, and it went like that day after day, then, school started, and I was enrolled as a girl. Surprisingly, nobody knew or cared what I looked like, and I kept working. As the days became weeks I was able to adjust my thinking, and in many ways, became the girl I looked like. Because I was so active at work, I lost weight, which made me look even more like a girl, and my mannerisms, the way I talked, and how I related to the men that I served became almost natural. The bookie always kept track of what I owed, always gave me the money I was due, and never let anyone touch me in any way inappropriate. He broke one guys arm when he squeezed my butt!

About the time summer break started grandma pulled me aside for one of her "friendly" little chats, which always meant that she talked and I listened. This time, what she suggested was no longer unthinkable, but probably for the best, and I did not object when she told me what the consequences would be. I didn't even ask what my mother said about it! Grandma simply told me she would take care of it, and within a few days I was taking the pills that would give me the body of a girl my age. I kept attending school and working for the bookie, while at the same time the pills were working on me. It didn't seem to take that long, but my body was soon hairless, I had grown my own breasts, my hips had filled out, and I had a little bubble butt. I had turned 17 with no sign that I had ever been a boy, unless I undressed, and even that was useless by then. When it happened I was out front, serving drinks as always. I heard the three shots, bang bang bang, and like everyone else, I hit the floor. Two men ran out, followed by almost everyone else. Someone had stepped on my arm in their rush to get out, and broke it. Laying there in pain I wasn't able to leave before the cops showed up, but after they found out I had a broken arm, the gave me to the EMT's while they searched the place.

They found the bookie, still sitting at his desk, but he had three small holes in the middle of his forehead. I was taken to the hospital, met by my grandparents and two husky cops. They knew that I had not shot the bookie, so all they asked me was what I saw and when, then I was able to go home. Of course, without the bookie there, I didn't go to work. It was almost a month before someone called me, and asked to come over. Grandpa said it was okay, but he had his gun in his lap when grandma let the guy in.

"Hello" he said, my name is Mike, and I work for some people that the bookie dealt with. Going over his books we saw that Diane was working off a debt she incurred by waiting tables."

"Is there a problem?" grandma asked, "Diane did everything she was told to do, and she did not shoot that man!"

He held up his hands, then…"No Ma'am, there isn't any problem, we have written off the entire debt. She was a minor, and that is against our house rules, but bookie took advantage of the situation, and pocketed the money she was paying him. That has made my superiors very unhappy, but we do not hold Diane responsible in any way. I am here to tell you that your debt is paid in full, and that you have no obligation to out organization in any way. That said, I am also here to offer you a job. Since we are completely aware of the circumstances you were in, and what bookie made you do, we have an opening at one of our finer establishments that we would like you to consider. We'll pay you the same $500 a week, plus a third of all of the tips."

"What kind of job, and where?" grandpa asked.

"She would work as a reservation clerk to start, and fill in for the Maitre' de when needed. It is the Chez Riverfront, and I assure you, she will be in no danger. My own son works there, and one of his duties will be to make sure that Diane is home safely every night, even if he has to follow you in his car."

Making $500 a week…plus a third of all the tips? I would be able to go to college! I immediately said "yes", but grandpa told him we would let him know, and he handed grandpa a card. Then he left! I was, for the first time in three years, debt free, plus I had a job offer that was better than fantastic! We talked it over, but there wasn't much of a struggle when I said I wanted to do it. I would be able to wear nice dresses for a change, rather than skirts and jeans, but I didn't say that. Grandma knew it though, and after grandpa called Mike the next day and told him I could take the job, grandma and I went shopping again.

The work was easy, and I felt like a real Princess. All of the men and women that came there to eat wore beautiful clothing, and were generous when they tipped. Only once did I have any trouble, some guy made a grab for my breasts after he had to much to drink. He was hustled out, and I never saw him again. James, the young man assigned to make sure I got home was a waiter. He was about my age, and like his dad, very handsome with bright eyes that seemed to twinkle, and a smile that always seemed better when he looked at me. But I had never once considered that a guy would find me attractive, simply because I had always hoped that I could be a man again. But that changed when my body changed. Once I was able to cup my own breasts in my hands, feel the softness of my skin and enjoy the sensations my nipples gave me when I rubbed them, I quit worrying about being a boy again. James, for the first time awakened in me the realization that as a girl, I was pretty enough to have a guy want me.

Over time, James began to pick me up and take me home, which lead to our stopping on the way home one night. When his lips touched mine I felt the jolt only a man can give a woman. Wanting more, James and I stopped every night, which made it hard for me to keep saying no, especially when he had his hand in my bra. When I touched him for the first time it was over. I had to make him happy, and I had only way to do that. I unzipped his pants, reached in, and felt it, throbbing and hard, yet soft to the touch. He lay back, letting me caress him, then, all at once, it was out. I looked down, bent over, and found myself eye to eye with it. As my mouth opened to take him, my tongue flickered out, and for the first time I touched a man in a way that not many men would do for another man. I felt his hand on the back of my head, gently pushing, opened my mouth again, and with a single plunge, took him.

He was very satisfied, and I was happy that I was able to do that for him. Even though I was a male in my panties, I was a woman everywhere else, and I didn't even consider not making him happy. James and I started dating, which neither of my grandparents said anything about. It was after Jim and I had been dating for a month that I took him to see and meet my mother. Mom and I had seen each other about once a month since this all started, and while she still held out hope that her son would return to her, she knew that I had the body of a girl, and didn't want to be a boy any more. Having her meet Jim would be my way of letting her know that I was a grown woman, not her son. Grandma talked to mom on the phone before Jim and I went there, paving the way for us.

Mom took it well, smiling the whole time we were there. Jim held my hand and was the perfect gentleman, which made mom feel a little better I think. Mom always referred to me as Diane, and never once mentioned that I had been a boy at one time, and that eased my fears a little.

I'm now in college, a complete female, courtesy of Mikes contacts, who were able to help me. Jim and I parted ways, but as the first guy that loved me, he holds a soft spot in my heart. I'm taking business management courses because Mike has promised me a job in his organization when I graduate. Life is good now.

 

© 2001

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