The School Tramp

If we were at school, we were usually hanging around the front, smoking and making fun of the nebbish kids who actually went to classes!

Mom did not know any of this of course. She thought I was working hard. This was proven by all the wonderful test marks that I kept getting back from all the teachers who I was sucking and fucking for better grades.

Mom had no idea that I was such a cock slut. She did know that I was having sex, both with guys and girls. She most often saw me with Karen, but to keep her from being too curious I asked Jamal to sleep over several times. Jamal was one of the stars of the basketball team. He was not the tallest of the black players on the team, but after having sex with all five of the starters at the same time after one game, I knew that Jamal had the biggest dick. He was also smart, bright and articulate. So it was good to have him over once in awhile and pretend that he was my boyfriend. Jamal was happy to help me out, provided that I let him fuck my ass whenever he wanted, and also so long as I shared some weed each time!

One of the people who became a close friend during this time was Dougie. He was the first guy I ever fucked in the ass, and then I turned him over to Danny, remember? Well Dougie and Danny were definitely an item. Dougie came out to his classmates as gay, and over time he began to act more effeminate, adding a bit of swish to his step (I suspected that Danny had Dougie wearing a butt plug most of the time). If you looked at him closely you could see he was usually wearing a bit of lip gloss and eye liner, and clear polish on his nails. His mannerisms also began to take on a bit of.., um how do I put this.. well, he was acting more and more like a stereotypical fairy! But I enjoyed his company!

I began to drink a fair bit when I was out on dates. Cosmopolitans and chocolate martinis were my favourites! However, I would drink anything that a man would buy me, and so I sampled a lot of different alcohols. I can't say that I liked single malts, but I never turned down a drink from a guy. Many nights I came home ripped and would end up puking loudly in the bathroom. Mom really disliked having to clean up after me in the morning. And I really hated it when she shouted at me when I was hungover!

But I had been a nerd for nineteen years and now I loved being a party girl! So what if I drank a bit too much, smoked a bit too much, fucked every guy and gal who asked me for the time. Life was to be lived!!!!!

All of this was going on during the week. Friday and Saturday nights were different.

I had gone to see Coach's plastic surgeon friend. He had me strip naked and took a long look at me. He asked me what my realistic long term goals were and I told him the truth. I wanted to look like the most beautiful girl, but keep my dick. I wanted a nice round ass, and nice large tits. I told him that my fantasy was to have nice hard fake looking breasts, what I called porn star tits! He raised his eyebrows at this. He said most women wanted breasts that no one could tell were fake. I told him that I wanted everyone to know that my breasts were fake and I wanted them big.

He looked me over and said that this could be done. He also looked at my face and told me that I had a very attractive face, but that as I got older it would get even more angular and masculine. He suggested that I consider having some work done on it soon, to stave that off.

He told me that the breasts that I wanted... the size that I wanted.. would have to be done in stages, so that the skin could stretch and grow.

The first part of the procedure, to insert the smaller implants and to touch up my face a little bit would cost five grand, with another five grand needed after that. He said that when I had the money I should call and he would schedule me for a day or two after that.

He also told me that I should stay on the hormones to get the effect on my skin and some body shaping, but after a certain point I would need to get off of them because they would affect my ability to get an erection. Careful monitoring and using the hormones on an off should achieve the results that I was looking for.

I told him that it might be awhile before I could come up with the money. He just smiled and said that a pretty girl like me could come up with the money pretty quickly if I put my mind to it.

He also gave me a business card of someone he thought I should email. It was for a video production company in California. I did not recognize the name, but when I got home and googled them, I discovered that the company made porn films specializing in shemale series, including several that featured young performers barely over he legal age, like "Bang My Teen Tranny Ass", and "My Daughter Has a Dick". This was NOT something I was interested in. I stuck the card away in a drawer.

But his comments did get me thinking. If I wanted boobs sometime soon, I needed some money. And I knew how I was going to get it.

The first Friday night, I asked Karen to go along with me. I put on a skimpy skirt and tarted myself up real slutty. Mom practically screamed at me when I left the house dressed like that! She was getting to be SUCH a bitch! But after a ciggie and then a joint in Karen's car, I was feeling much more mellow. We drove over to the Kat Klub and went inside. We sat at the bar and ordered a couple of cosmopolitans. It did not take long before the first guy hit on me. I was nervous and I sent him away, disappointed, after a bit of conversation.

Karen was talking to one of the other girls in the place when the second guy hit on me. He was a lot older than me, but definitely cute in a distinguished way. He wanted to know how much it would cost for a fuck and I told him we should talk outside.

Fifteen minutes later he had paid for a room at the Ambassador and I had two hundred bucks in my purse. I was on my knees sucking on his cock and enjoying the taste of fresh meat. He almost blew his load, but he had paid to fuck me, so I laid him down and sat my boycunt down on his dick without him realizing he was in my ass, rather than in a pussy. It was another ten minute ride before he blew his load and then the guilt and shame took over and he practically ran out of there without even washing off. I wondered what he would think when he got home and his dick smelled of ass instead of pussy!

Before I went back to the Klub I opened a vial that I had bought from Karen and poured some powder on the bathroom counter. I formed it into a line and then snorted the coke. I'd told myself that I would only use cocaine on special occasions, and fucking my first stranger for money certainly counted as special!

When I got back to the bar, Karen was being rather friendly with the gal she had met. They were both touching each other provocatively. But when I ordered drinks for both of them and myself, they toned it down. Another couple of gals came over and suggested that we all move to a table.

They were all working girls, eager to get money from the guys who came into the Klub looking for a bit of relief. To my relief, they did not mind that I was there, also trying to make some bucks. They did however want to make sure that I was not undercutting their prices. They did not mind some competition, so long as it was fair. We talked about prices for blow jobs and fucking and such and I agreed to charge the going rate, or even more if I could get it.

The girls were also stunned to find out that I was transgender, a shemale in their own terms. They knew several customers who would be interested and said that they would steer them to me. They wondered about Karen, and Karen told them that she was just there for support for the night, and she was only into other women. The gals said that they could send some customers her way too, if she wanted, but she declined. She said she made enough money selling weed, and she proved it by selling some bags to the other gals there.

Karen left soon after, with the other girls promising to look after me on my first evening as a working girl. I had two more customers that night. One was just a quick blowjob in the parking lot, and the other was a guy who liked a girl with a dick. I took him back to the hotel room which was already paid for and he came in my ass once, and on my tender small breasts a second time.

The second guy asked for my email address so that we could work out some timing other than weekends.

It was late when Carlos picked me up to take me home. I'm afraid I had had too many chocolate martinis and was very drunk as he drove me home and so, for the first time, Carlos did not get his blow job!

I stumbled up the stairs and threw up before I got to the toilet! Mom was going to be pissed off again!

It took most of the next day for me to get over my hangover and I promised myself I would go easy that night. I was back at the Kat Klub again that night and I went back most Friday and Saturday nights.

One thing that I noticed was that the guys who approached me were often turned off if I seemed too intelligent. They seemed to like a gal who was a bit of a bubble head; who seemed to have only half a brain. It was not hard for me to just use short words and giggle a lot when they talked to me. And it was fairly easy to pretend to be ditzy after I had a couple of drinks in me, and had had a couple of joints. I began to enjoy playing the airhead!

I also realized that I had lost all interest in my studies. I had no ambition to go to college! So I went to each of my teachers and told them that I no longer cared about the marks. I told them it would probably be best if they continued to give me good grades, but I really did not care. Instead I wanted some money from each of them if they wanted me to continue providing them with sexual favours.

One teacher stopped seeing me. The rest went to Principal Henderson for a discussion, and then started paying up. When I got paid, I gave Jordan twenty percent, as we had agreed!

It took me seven weeks to raise the money that I needed. It would have been only six weeks but I also had to raise money to pay Karen for the weed that I was getting from her, and the bit of coke from time to time too.. Only a tiny bit mind you. I wasn't going to get myself hooked on the stuff, honest!

And so, I called the plastic surgeon and a couple days later I took the day off school. It was just simple day surgery. He cut me just underneath my developing breasts and inserted the very round, very firm implants. At the same time he used his implements to shape my nose a little bit and he dabbed just a bit of collagen under my lips in strategic places to make my lips a bit fuller.

He talked about how next time he would like to make my lips fuller still, and how he would like to enhance my cheek bones and perhaps alter my eyebrow ridges a bit.

When I got home I went straight to bed and did not encounter mom until the next morning. My chest was bandaged, as was my nose. She instantly knew what I had done and she broke down crying. She told me I was out of control! She wished she had never given me permission to become Sindy. I told her I didn't care what the fuck she liked or did not like. This was my life and I was going to live it how I wanted to!

I went to my room and opened my window and lit up a joint and tried to calm down. I admit that the pain from my chest and from my nose did not have me in the best of moods.

I went back to bed and slept most of the day.

When Mom came home from work, I had dinner ready for her. I hugged her and told her I was sorry for saying the nasty things I had said. She forgave me, but still wanted to scold me for what I had done. But she knew that this would only make us shout again, and what was done, was done. We ate in silence.

A week later all of the bandages came off. I put on one of the new bras I had bought and wore a low cut top in order to show off my new tits at school. Everyone oo'd and ah'd. My nose was now shorter and upturned slightly. My lips were thicker.

But it was my breasts that got the most attention, of course. They were each about the size of a softball, nice and round and firm. As I said, I had no interest in nice soft boobs. I wanted obvious fake tits and that is what I had. My nipples were stretched a bit too, but when I got excited they perked right up and were very evident even through my bra and blouse.

Principal Henderson was the first man to put his cock past my new lips. Coach Grogan was the first man to slap his large cock between my tits and fuck them.

That night I preened in front of my full length mirror and adored my new hard firm tits. I plunged my dildo in and out of my ass as I masturbated furiously!

It was so nice having tits. I loved having them sucked on and I just adored having a man use them as handles to hold onto firmly while he jackhammered into my ass from behind! And of course, they increased my business on Friday and Saturday nights.

I continued picking up guys at the Kat Klub on weekend nights. As I mentioned earlier, I was having fun dumbing myself down and playing the airheaded bimbo to these guys. It snared the guys who thought they could take advantage of me.

Many of the guys who sought me out knew about my big secret in my panties. Some did not care, some wanted me to fuck them! I charged extra when a guy wanted me to fuck him, or if he wanted to suck me - and those guys gladly paid. Sometimes a few of us gals would go to a party and we would have to split the take. Karen drove me over some evenings, usually because she wanted to drop off some weed to many of the other working girls who had become regular customers.

Chapter 24 - The School Tramp

Life was strained in our house from then on. Mom was constantly angry at me, and I was mad at her.

I was not very happy either, having lost my direction. What DID I want to do with my life? Truthfully, as I said before, I did not have any plan except to suck and fuck and smoke weed. I wanted my next surgery. I wanted larger boobs. In addition to the facial modifications, the doc had also suggested moving some fat around on my body, onto my ass, to give me an even fuller figure.

I was doing my best to earn the money for the surgery. Mom would object again, but I had no intention of telling her when I was going to have it done.

I was being much more select about whom I was fucking lately. Well, let me correct that. Anyone with the right money could have my ass or mouth. But I was more picky about who I would fuck for free, or for the price of a nice dinner. I dated very few schoolmates now.

I did get one scare. One Saturday night I had just gotten back to the Kat Klub after being fucked by a chubby business man. That had put another hundred and fifty bucks towards the bigger boob fund. I had the keys to the Ambassador room, so I was hoping to be able to make some more money on my back before the night was done. I was talking to Candice, another of the working girls, when a good looking guy came up and bought us both drinks. He asked how much we would charge for both of us to do him at once and we worked out a price. We took the guy back to the room and just after he paid us and I put my share of the money away, he pulled out a badge and told us we were under arrest for being hookers!

This was going to mean being hauled down to the police station and held in a cell while the cops called my Mom! I definitely did not want her finding out about my weekend activities! The undercover cop called for a cop car to take Candice and I to the station and the holding cells. A few minutes later Patrolman Dick Hooper and his female partner walked through the door. Dick took a long hard look at me - I had tits and a new nose now - and asked me if I was Sindy! I nodded, almost in tears. Dick took the first cop aside and talked to him for a bit. The first cop turned back to us and said that he was not going to pursue the incident further, since officer Hooper had vouched for me. The cop and Dick's partner left with Candice leaving Dick and I alone in the room.

Dick opened my purse and took out a joint. He also fingered something else that was in there. We sat and smoked the joint together. He told me I was looking very fine and reached for his belt. I knew the price I had to pay, so I knelt and gave him a quick blow job, swallowing his cum at the end.

Dick told me that if I got in trouble like this again, I should call him from the station, rather than a lawyer. However, he said, I needed to be careful. He had found the small vial of coke in my purse and told me that he could get me off of a prostitution charge, but if I was caught with coke there was nothing he could do for me. I thanked him with a kiss on the cheek and then called Carlos and had him drive me home. I'd had enough excitement for the night.

A couple days later I was standing outside the school smoking with the other cool girls. Not a joint, just a cigarette. I did have a mild buzz from some coke I had snorted about an hour earlier.

Stevie Henderson came up the sidewalk towards us and tried to speak to me. He stammered something, and I mimicked his stutter. He got all red and ran off. I think the dweeb was actually crying! I laughed and shouted after him that he was a pansy. All my friends had a good giggle at that!

At the end of the school day, Karen and I were sharing a joint behind the sports field bleachers. I had just finished sucking off one of my teachers and needed the joint to relax. I told her about her brother and she said that she had told him that it was hopeless, but he had persisted anyway.

I asked her, what was hopeless? She said that Stevie had approached her the day before and said he was going to ask me out on a date? A date, I echoed? Yes, she replied. Stevie had confessed that he was a virgin (well, duh! after all he WAS a nerd - what girl would want to date him!). He had asked Karen for her help, to ask me if I would go out with him. Karen had said that he should ask himself if he truly wanted a date.

Why me, I asked her. What made him think that I would go out with him. Yes, we had been friends when we were both guys, but now.. well, I was so far beyond him!

Karen looked at me and told me. Stevie had told her that I was the School Tramp. He figured that if anyone would go out with him, it was me! He'd heard I had fucked most of the guys, and a lot of the girls, in the junior and senior classes, and even some of the teachers. So surely, he reasoned, I would be willing to go out with him, and he could lose his virginity.

Karen and I laughed at that.

But he was right, in less than six months, I had gone from wanting to lose MY virginity to Becky Winters, the School Tramp, to becoming the School Tramp myself!

Chapter 25 - Happy Birthday to Me!

My birthday was in early March and Mom, being Mom, tried her best to mend fences with me. Unfortunately, this ultimately led to her finding out just how big a slut her new daughter was!

I had seen a poster at the Kat Klub for a strip club in Springfield where there was an upcoming event that I thought would be a hoot to go to.

The club was called the Cradle and was a typical female strip club. Twice a year, including this Saturday night, they kept the men out and let only women in - to see the male strippers that they brought in. Sort of Chippendales, but not with that trademarked name. The club found it to be good business because the women spent a LOT of money, and also, once the show was over, at midnight, a lot more guys showed up and paid for admission, knowing that there were a bunch of horny gals inside!

Mom agreed to treat Cassie and I to an evening out, and Karen was going to join us as well. If you have not guessed already, Karen was my closest friend amongst all the other girls at school. Mom approved of her because she was Jordan's daughter. Mom knew that Karen was a lesbian, and was fine with that. Of course if she had known that Karen was the biggest seller of weed in the city and that she was selling other drugs too, she would have freaked.