The School Tramp

He told me that he had never before hired a chick with a dick, but he could see where I might be a hit with some of the patrons, even after the novelty wore off. I told him that I was still in school in Bigelow. He said that was no problem as the club was not open early in the week.

He told me that if he took me on, he would expect me to be in the club Thursday Friday and Saturday nights, and sometimes on Sundays. The club hours were nine to two, but on slow nights I could leave at midnight if I wanted.

He told me the club did not pay me any wages at all, so that technically I was not an employee and they could not be held responsible for my actions. Yeah, the club got busted four or five times a year, but the charges never stuck.

I would be on stage dancing twice a night, and would wait on tables and serve drinks when I wasn't on stage or otherwise occupied. And by otherwise occupied, he meant that there were rooms down this back corridor where girls could take patrons who wanted private lap dances, or anything else they might agree to. There was also a stairway to the second floor where there were four rooms with couches or beds.

I got to keep all of the tips that I made while dancing and serving drinks. That was my pay. If I made any deals with patrons, I had to give the house thirty bucks every time I used a ground floor room, and seventy five bucks each time I used one of the second floor rooms. What happened between me and whoever I took up there was my business. He grinned at that!

He told me that on a good week, I could walk out of there with a thousand dollars of my own money, if I was nice to the customers, and they were nice to me!

I told him that I was not looking for a long-term job. I was only looking to make enough money for bigger boobs and some other enhancements. He told me to strip and I did, my cock hanging limply. He walked around me and poked my hard tits. I told him that my plans were to get some fat injections in the ass, and to get tits at least twice the size of what I had now, plus plumping up my lips even more.

He pushed me down to my knees and undid his pants. He waved his dick in my face. His whole body stank of stale cigar smoke and sweat, but I did not hesitate in taking his fat cock into my mouth and working it over real good. He let me suck on him for only a couple of minutes before he pulled me up. I thought he was going to bend me over his desk and fuck me. But instead, he told me to climb up on his lap. He leaned back in his chair a bit and I climbed up facing him, and lowered my dick onto his prick. He then sat back and told me to ride him. While I was fucking myself on his dick he was mauling my tits - squeezing them in his big paws, and sucking savagely on one nipple and then the other. And taking puffs on his obnoxious cigar all the time. Up close he smelled even fouler, but I realized that I wanted this job. It was a way of making steady money doing what I enjoyed, and was definitely a step up from working the punters at the bar at the Kat Klub.

While he was fucking me and grabbing me with his smelly greasy hands, Gambetti was also swearing at me, calling me a dirty whore, a fuck slut. He seemed to love foul language and trying to humiliate people. The only thing he said that did make an impression on me, was when he told me that my ass was even tighter than my boyfriend's. Apparently Gambetti preferred ass to pussy (something that most of the other strippers confirmed to me once I knew them better - he'd had his cock in all of their asses at one time or another). Also it seemed that Troy was one of his favourites when the male strippers performed at his club.

It took fifteen minutes to get him off. He dumped a heavy load of cum up my ass. I did not get any pleasure from the fucking, but I did get a job out of it!

As I tidied myself up and dressed, Gambetti told me that if I signed on, and I proved to be a good earner - meaning that I made HIM a lot of money, then in three weeks he would loan me the money I needed for the tits, bum, lips and whatever. I could pay him back by turning over two hundred ad fifty bucks each week until my debt was paid to him. He told me that he doubted I would need the loan though. He suspected that I would be earning quite a bit of money for myself, and for him.

We shook, and that was how I became an exotic dancer!

Chapter 27 - Dancing Queen

School was now SO absolutely fucking boring! Carl the nerd had liked the structure that school gave to his life. But Sindy had no interest in math, or geography or economics. Boring boring boring. School had now become just a place for me to hang out with my friends and get some good fucks behind the bleachers or from one of my teachers.

Once I started dancing at the Cradle and was getting money for sex in the back rooms, I realized that I was stupid to just give my ass away for free at school. I needed money for my bigger boobs fund, but also because I was now giving Karen a lot of money for weed, and for some blow from time to time, despite patrolman Dick Hooper's warnings. Oh, I made sure never to be carrying very much with me!

But I stopped giving my ass away at school. One or two of the guys would approach me but usually left angry when I told them how much I wanted. I was still getting lots of sex during the week. Coach Grogan was still ramming me on Mondays along with my double dose of hormones.

Jordan, the principal, was not a frequent visitor to my ass anymore though. Our schedules clashed too much and he was getting a bit more serious about mom. I guess guilt over diddling her former son was keeping him away too. I wasn't too pleased with this development really. Jordan was a nice fuck even though he was an older man. It was hard to believe but I was jealous of mom, and a royally pissed off at Jordan.

I went to the Kat Klub a couple more times to earn a bit of money, but soon stopped. I was now having to go midweek, and there were not many guys looking for hookups on those nights. Most of those evenings were spent in the company of men who had become regular customers... the few who could sneak out on their wives midweek

I never showed mom my test results anymore. They were coming back as either Ds or just as incompletes. Since I was no longer fucking any of my teachers, none of them gave me decent marks.

My debut at the Cradle had been a big success. Gambetti had decided my first night of stripping would be the Saturday night. Thursday and Friday and early Saturday I just waited on tables. I got my ass pinched and groped a lot. I made a nice amount in tips, but despite getting offers to take me in the back, Gambetti told me that the private rooms were off limits to me until my big debut.

A couple of the other girls gave me private lessons before the club opened on those nights, and I watched the girls stripping as I served drinks. None of the other girls knew my big secret though, not until the grand unveiling at the climax of my first strip on the Saturday night. Gambetti's voice introduced me to the audience by the stage name he had thought of for me: Sindy Suxxx!

I can't say that my first try at stripping in front of an audience was much of a success. I was nervous and dancing in four inch heels is a challenge for anyone. But everyone was delighted when my tits were revealed. And once I was down to my thong only, and then pulled that off, the crowd went silent, and then they roared with applause and laughter. I danced for the next five minutes with an incredibly hard erection sticking out from my groin. Despite being revealed as a shemale, the audience applauded and egged me on, just as much as they did any of the other girls, and the money handed to me and thrown on stage was just as good!

I left the stage to some standing ovations! And quite a few standing erections too!

When I went back out on the floor, I had several men eager to spend some personal time with me. Over the next hour I took three guys to the back room and charged them fifty bucks each for lap dances, and each took me up on a blow job for additional money.

I took a break to wait on tables. Now that my cock had been revealed, my waitress outfit consisted of a minimal bra and a pair of sheer panties that my cock could easily be seen through.

I danced a second set that night as well. I also took four guys up the back stairs, and up the back passage too, if you know what I mean!

At the end of the night I paid Gambetti his cut and also sucked him off. He did not cum very much, so I suspected that a few of the other girls had drunk at the same trough before me!

By the third week Gambetti admitted that I was a hit. The place was even busier than ever on Friday and Saturday nights because the guys were coming to see me! Gambetti had me start dancing a third set each night, and I was sharing top billing with one of the other gals.

I was also having fun playing at being a dim witted bimbo at the club. As Carl I had always been pretty sharp, but that had not gotten me anywhere in life. Men definitely felt threatened when their pretty women seemed too bright and so I found it much easier to extract more drinks and money out of my customers if I did not think too hard. Of course, being high on weed, and taking a snort of coke each night before getting on stage all left me pretty muzzy headed anyway. There were even a couple times when I forgot to get the money from the guys before they put their cocks in my mouth and between my tits!

In addition to the actual sex, I found it to be such a fucking turn on to give guys a lap dance. I would take them to the back room, get their money, and then spend the next ten minutes in front of them and on their laps, grinding my ass down on their hard cocks, trapped in their pants, and rubbing my tits across their face!

After my third weekend, Gambetti called me up to his office. We had a ritual by this point. I knew that before we would talk any business I had to blow him, so I got on my knees and took his cock in my mouth. I also pulled down my top so he could look at my firm tits while I sucked.

Once I got him off, and swallowed - he always made sure I swallowed his foul slime - once I swallowed, he showed me a loan agreement and asked me how much money I needed. He was making good on his promise to fund my next round of surgery. But I declined. He had been right when we first met. I had already saved up almost enough money for the surgery. I figured that three more weeks of earnings would be enough for me to be able to afford my larger tits without going in debt to this sleaze.

I told Gambetti that I had already talked to the doctor and that when I had the surgery I would need three weeks off from the club in order to heal up. We looked at the calendar and agreed on which three weeks off I would take.

I figured I should thank him for his support and so I bent over the desk and let Gambetti sink his cock into my boipussy and fuck me from behind. While I sucked him off almost every time I saw him, this was only the second time Gambetti had fucked me. This time, with him pounding me from the rear, I could work his cock against my prostate and get some pleasure of my own. As he fucked me, I lit up one of my cigarettes. I needed something in my mouth!

Three weeks later, I did indeed have enough money for the surgery. It had been a bit close though. The rain had been heavy one weekend and so the crowd at the Cradle was a lot smaller than usual. So the next week, I had gone to the Kat Klub almost every night, looking for some extra money, and I had also called up many of my regulars. I got home way past two am every night and mom was furious with me!

Well she was going to get even madder at me, but thankfully I would not be around to see her explode!

Chapter 28 - A Bit of Revenge

One unsettling development was that I had a falling out with Karen and it was a serious one. Though why the fuck she really cared, I do not know. But of course, I had to get my own back at her, and I did! On her and her dad in fact.

Jordan's defection from my attention was really bothering me. He had not fucked me in a couple of weeks. I liked his hard cock in my mouth, and ass. But I also liked the nice hotels and restaurants that he took me to when we went out. He was about the only guy who treated me like a real woman.

I guess this was too much on my mind one time when Karen and I got together. One Thursday night I left the Cradle early because Karen came to Springfield to pick me up. She had actually gone into the city to make a pick up from Jade and Dwayne and offered to give me a lift home. It was a slow night. I had only taken one guy into a back room for a lap dance and a blow job, and only one other guy had taken me upstairs to fuck my ass. Gambetti agreed that it was a slow night and, once I blew him too, he agreed I could leave early.

Karen pulled her car over on the way home and we toked up on her bong pretty good. I think we sat there for over an hour just getting mellow and talking about life. I had told her I was close to having enough money to get my next surgery. She told me she was happy with the ample tit flesh she had come by naturally. We got talking about our bodies and then about the various men (in my case) and women (her) we had been having sex with, and somehow it slipped out that I had been fucking with her father, or rather, that he had been ramming his stiff cock up my butt, repeatedly!

As I say, I don't know why it should bother her, but she went fucking ape shit crazy on me, yelling and screaming. It was like I had somehow invaded her family life! She swore at me and told me that I shouldn't have anything to do with her dad again!

As it turned out, Jordan did not want to see me, but I was not going to tell Karen this! What fucking business was it of hers as to who I sucked and fucked!

Karen dropped me off at home and drove away in a huff. Later I was concerned about losing my supplier for weed and coke, but Karen was not that kind of gal. We did not hang around much after that, but she still sold me dope, though she charged me more.

That night though, I was steaming mad myself at her reaction. At her, and at her father. Hell, at the whole Henderson family - Jordan, Karen and even Stevie. Poor little virgin Stevie who was too shy to ask me out on a date.

Hmm... now there was an idea. Maybe I could have some fun with Stevie, and get some of my own back on his family!

The next school day Karen was not talking to me. I hung out in front of the school with a few of the other cool girls, but when Karen saw us, she just hurried past. I flipped my middle finger at her back and muttered fuck you under my breath. A couple of the other girls noticed and asked what was wrong, but I did not tell them

After classes, I waited in the hallway outside of the math lab. I knew it was math club night, Carl used to be a regular. I had been such a dweeb back then!. When Stevie came along and saw me, he hesitated. But I put on my sweet smile, batted my eyelashes at him, and made sure that he got a good luck down my ample cleavage. I told him I was so sorry about laughing at him the other week, and asked if what his sister had told me was true, that he wanted to go on a date with me? He blushed and stammered, yes.

I reached my hand down and gently cupped his rigid cock in his pants and told him that I would love to have him take me out and I suggested that we get together on the following Monday night. He moaned, and I suspected he had just cum in his pants. He nodded and ran off.

We talked by email over the next couple of days. I danced at the Cradle as usual on Thursday to Sunday and made some plans in advance for the Monday night.

When Monday rolled around, I went home and changed and picked up a bag. As I went out the door, Mom was yelling at Cassie about something for a change and so I made a quick escape. Carlos picked me up and we headed downtown to pick up Stevie. Stevie was cleaned up and wearing his best shirt and pants, and even a tie. He was even carrying a small bunch of flowers which he gave me. He was very nervous. I had Carlos drive us over to the Ambassador hotel in Seneca. When we left the cab, I gave Carlos a peck on the cheek, promising him a special treat on the ride home. I left Stevie's flowers in the back seat. I did not forget them, I just had no use for them.

I checked us into a room, and then Stevie and I walked to the Kat Klub where we sat and had a nice light dinner. With the food I made sure to have three drinks myself and put a couple of sweet drinks into Stevie as well. He'd had beer before but never a cosmopolitan, nor a margarita. I gave tentative waves to a couple of the other working girls who were in early. But they picked up my signals that I wanted to be left alone with my... date.

Stevie had been my best friend for several years, until Cassie had made me dress up as Sindy for a date and my whole world had changed. We had grown apart as I began spending more evenings sucking and fucking. By Christmas time when I had become Sindy permanently I had written Stevie off as just one of the losers at school.

I had to admit that for a guy who had never had a date with a girl, Stevie was trying hard. He actually found things to talk about, and did not stammer. Even though he was a bit over eighteen, he did not have to shave much, but even that was nice and smooth. He offered to take me to a movie or do something else, but I told him that was not a good idea for first date. We would not be able to talk, and he would not be able to look at my boobies. That made him flush.

I told him that I knew that the main reason he asked me out was because he wanted to lose his virginity. He nodded hesitantly at that. I told him that was okay, because I was eager to take his virginity. However I twisted the conversation around so that I was talking to him more about myself for awhile. I told him how Carl had been unhappy, without knowing it. It was only when I started playing at being Sindy that I was really happy... and the more time I spent as Sindy, the happier I was.

I made sure that Stevie paid the bill and we started to walk back to the Ambassador, but I took the long way. I had time to finish a cigarette. We held hands as we walked, Stevie's hand gripping mine very tightly. When we got to an isolated spot, I lit up a joint and took a couple of good long pulls on it, then handed it to Stevie. He shook his head, and so I leaned forward and kissed him, exhaling smoke into his mouth. He gasped and coughed. Then he reluctantly took the joint and toked on it himself. He said that he had stolen a joint from his sister once and tried it, but did not like it. I intended to make sure that by the end of the night he definitely enjoyed weed as well as several other things!

When we got back to the hotel room, I had convinced Stevie that becoming Sindy had been the best thing that could possibly have happened to me. When I looked him in the eye, I could see he was a bit glazed and I lit up a second joint and we shared that. Between puffs we kissed a bit, sharing the intoxicating smoke between us. I think this was the first time Stevie had ever kissed a girl and I wanted to be sure he related the pleasure of kissing with the sensation of being high.

I then told Stevie that we could have sex. He looked eager. Or, I said..... Or, he asked?

I told Stevie that I would have sex with him. I would love to suck on his cock. I grabbed his cock in his pants, and he squirmed. I would let him fuck my boipussy. But we would do it only this time. He should have no delusions about us having sex again. And he could go back to fantasizing about girls, and jerking off alone at home. Or..... Or, he asked?

Or, I said, I could help him to be like me. I could show him how to dress up nicely as a girl, and introduce him to some nice boys who would love to have a good time with him. It was his choice. Did he want to have one night of fun, or did he want me to open the door for him to escape his nerd world and start to have lots of sex and fun?