The School Tramp

The next morning, I was up early enough that I avoided mom and the blowup that would happen if she saw the slutty outfit I had picked out for school. I walked the several blocks to school. Normally I would have met up with Karen this early and we would have driven up to Blueberry Hill, the make out point where we would have each snorted a couple lines of coke. Instead I had to do a line in the deserted school washroom.

When I came back out of the school, all the girls rushed to me and admired my new figure. Jordan... Principal Henderson called me into his office and scolded me for my attire. He said that low top, bare midriff, short skirt and four inch heels were inappropriate school attire. He forbade me to go to classes dressed as I was. Well fuck him! This made what I was about to do even easier.

So I did not go to classes. I just hung out in front of the school, smoking and laughing with my pals.

When classes ended, I did go inside and went to Coach Grogan's office. But not alone. I had asked Stevie to bring along a bag with his Mink clothes and he went with me. When we got to Coach's office he was not there and so I had Stevie change and helped him put on a bit of makeup. I then had him wait in a closet.

When Coach came in, he was amazed at my huge knockers. I let him lay me down on his couch, squat over my chest, and pound his cock between my tits. He loved hooking his fingers in my nipple rings and pulling and twisting my jugs! He also lifted me in the air, and settled my ass down on his cock, raising and lowering me, pounding his cock into my ass as my new soft ass cheeks quivered. As always he was a delightful fuck, and I squirted my own sissy juice high into the air at the same time as he squirted his jism up into me. I could see Mink's face peeking out of the closet every once in awhile, a look of envy and lust on his face!

When Coach reached for the syringe to inject my hormones, I told him I did not want the injections anymore, and told him that today was the last time I would be letting him fuck me for free. I told him I would love it if he would call me and we could arrange to meet elsewhere, but he would be paying my regular rates from then on. He hugged and kissed me and wished me luck. I then told him I had a surprise, and motioned for Mink to come out of hiding.

Coach was startled, and then disbelieving as he realized that this new crossdresser was principal Henderson's son! But Coach's dick began to rise again! I told Coach that Mink was a bit shy, but he wanted the same deal that I had had.

In truth, I had never discussed this with Mink, but I wanted to screw up the Henderson family even more if I could. I told Mink to drop his panties and bend over the desk. I watched as Coach gave Mink his first injection of the super strong hormones. I told Mink to thank Coach Grogan, and he did, by dropping to his knees and taking that impressive black cock into his mouth. I took a few pics with my cell phone and a short video.

As I left the office, I hear Coach telling Mink how much he was looking forward to fucking him up the butt!

I'm sure Coach would have called me up and been a regular customer for my ass, but the way that things went down soon after, I don't think I ended up being one of his favourite people.

That night Mom caught up to me and we had a roaring argument. It was nothing that I had not expected. She still figured I had a future at school. She just did not see things my way. I only wanted to fuck and suck.. although I put it in much more polite terms for her. In the end I finally flipped my middle finger up at her, told her she could go screw herself and then slammed my bedroom door. I did not have any money dates arranged for that night, so I just stayed in.

Fuck her, I thought. So I had no problem smoking cigarettes and having a few hits off of my bong. I really didn't care if I stunk up her house!

I did not expect to be living there much longer. I contacted Cherry and she said that she would be willing to share her apartment with me. I could have the other bedroom if I split the rent with her.

Tuesday night I put on a little black dress which showed off my ample boob cleavage and my ample ass as well. I also wore dark garter belt and stockings and five inch stiletto heels. I told mom I was going on a hot date and to not wait up for me. She was going out herself, to dinner with work friends. She was steamed because Jordan had cancelled with no excuse other than that he was busy, but she was going alone anyway.

Carlos picked me up and we stopped along the drive for his usual reward. As we entered Seneca, I was inspecting myself in my compact mirror and cleaning up the small flecks of Carlos's cum off of my face. Carlos dropped me off at a very fancy restaurant where Jordan was waiting. We had wine and very nice meals. All of the men's eyes in the place were on me and my very tight dress. Afterwards, Jordan checked us in to a very expensive hotel. As he freshened up in the bathroom, I figured out where to position the two small video cameras I had brought along with me. The two cameras captured all of the action over the next two hours as mom's fiancee fucked the living shit out of my ass! Oh, I sucked his cock a lot too, taking it all the way down my throat. But most of the time, his hard dick was buried in my boipussy. I was on my back, up against the wall, across the small desk and riding on top.

The next day when I edited the videos together I particularly liked and featured the moving images of me riding on top of his cock, pumping my ass up and down on his cock, my large firm tits rigid on my chest, but my boyclit bouncing and waving around wildly.

As I put together the DVD, I also included many still images I had discretely taken from past meetings with Principal Henderson. The pictures had been taken over many months, so that it was very clear that Jordan had not just now been tempted by me, but rather he had also been fucking me when I had small tits and even back when I had no tits whatsoever, back when I had just started dressing. The earliest pics showed me still to be just a crossdressing boy - very cute, but a young man, nonetheless.

I put the DVD away for safekeeping. I would need it in a day or two.

Chapter 32 - Pounding Nails in the Coffin

Things got excruciating around the house when my final marks for the school year showed up. I had clearly failed every class and failed the school year. When Mom asked me point blank if I had been sleeping with my teachers, I told her that that is exactly what I had been doing, up to a point, and then I had decided I did not care, and so my marks had plummeted.

Mom broke down in tears and I just walked away from her on my four inch heels.

Cassie and I still hung out together at times, but as you know I now was spending much more time with Mink. Although I had turned him on to sex, booze and weed only a couple weeks ago, he was a fast learner and eager for more new experiences. I still never touched him, but we went on several double dates with some of my better paying customers. Of course I never told him the men were paying for his company and kept the money for myself. I was still taking discrete pictures and videos of him having sex. In particular I was training him to call all of the older men he fucked "daddy" and to be very vocal while cumming!

My sister Cassie was beginning to sound too much like mom - telling me I was drinking too much, getting high too much, and she told me I was fucking too much! She was much more privy to my private life than mom was. She was getting to be a bit too high and mighty for me so I had no qualms about finally making her see the light about Johnny. I of course knew that Johnny was a piece of shit! He was not good enough for my sis, but any time I tried to warn her about her darling fiance she would just ignore me.

So one day at school, I nuzzled up to Johnny, rubbed my enormous tits against him and told him I was no longer mad at him. Cassie had already told him that she was not going to see him that night. I told him that Cassie was going to be out until midnight, and Mom was away overnight. In fact, I knew that they were out together and would be home by ten. I grabbed his dick through his jeans and let him look down my top at my new cleavage and he agreed to see me that evening.

I made Johnny take me out to a nice dinner. While we ate I had his dick out of his pants under the table and was stroking him. I might be mad at him. I might think he was a louse. But he still had a nice cock! By nine we were back at the house and up in my room. He was very turned on by the sight of my melon sized mounds as I sucked on his cock. He got behind me and pounded his cock into my ass. My ass cheeks jiggled delightfully.

Johnny came twice - boy, he had stamina! We smoked some weed together and cuddled for awhile. When it was close to ten, I told him that I wanted him to fuck me again. His cock was up and willing. I told him that this time I wanted him to fuck me downstairs, bent over the dining room table. I led him down the stairs by his dick. I turned up the music loud on the stereo.

I was wearing dark stockings and garter belt and four inch heels. I leaned against the table, and Johnny rammed his cock up my bum chute and was fucking me furiously when mom and Cassie walked in the front door! Johnny did not notice them at first. Mom let out a gasp. Johnny's lubed cock was pistoning in and out of my ass, and I was panting in heat!

Five minutes later, Johnny was still trying to make apologies. I had immediately gone upstairs and put on a pair of slacks and a low cut blouse. I lit up a cigarette and walked back downstairs. Mom and Cassie were both screaming at me, Cassie calling me a cunt, and Mom asking me what the fuck I had thought I was doing!

I handed Cassie an envelope. Inside she would find other pictures of Johnny fucking me over the past several months. I handed Mom an envelope containing the DVD I had put together showing her finance porking me. I did not wait for them to look at the contents. I just picked up the two suitcases which I had already packed and had waiting by the front door. I took the suitcases out to Carlos' waiting cab and we drove away.

I had Carlos stop at a mailbox and dropped in two envelopes containing the same DVD. One was addressed to Jordan at the school and the other to Cassie at home. Each DVD contained lots of pics and videos of sweet Stevie dressed as Mink and fucking and sucking a variety of men. I especially liked the videos I shot of Mink telling his daddy to fuck him hard, since I had been sure to not get the man's head in the shot. Cassie would be wondering if it really was her father fucking the shit out of his own son!

I had destroyed the chances of Cassie marrying Johnny, and of mom marrying Jordan Henderson. Plus I had outed wimpy Stevie to his family. I was delighted. The Barton and Henderson families had fucked with the wrong gal, and I made them pay!

I never set foot in Bigelow again until after mom died.

Chapter 33 - Cherry gives me a helping hand

I settled down into a pretty stable life living with Cherry, for about six weeks. Thursday to Saturday nights I was stripping and waiting tables at the Cradle. My enhanced boobs and butt brought in a lot of cash and made me even more popular in the back room and upstairs. All the guys were fascinated by my giant jugs. The thick rings through the nipples were a sensation too.

I also saw regular customers on the other nights of the week, including some of the guys who I knew from the Kat Klub

During the daytime, I rested mostly. Oh, I got my hair done and my nails. But I spent most of the day time in a marijuana fuelled haze. I saved the coke for the evenings before I entertained a guest at home, or before I went on stage at the Cradle.

I was emailing regularly with Troy. We had both really enjoyed each others company and we suspected we could have something special if only we were both living in the same city. We talked about me flying to see him a couple weekends later, in one of the cities where he and the guys would be dancing.

Gambetti was thrilled that SinDD StaXXX was bringing in so many punters. I was happy with the arrangement and could have quite happily stayed dancing and hooking at the Cradle for several more months.

A couple days after moving to Springfield, I was almost completely out of weed and coke. Karen would not be talking to me again any time soon, much less selling me any dope. I thought of asking one of the other gals at the club if they know someone I could trust to supply me, but instead I figured I would go right to the source.

When Jade opened her door to peek through the crack, I had to explain who I was. I'd been through my second operation since I had been to her place with Karen. She was reluctant to open the door to me, but when Dwayne looked over her shoulder and saw my giant boobs, he pushed past her and invited me in.

Fifteen minutes later, I was sharing a giant reefer with Dwayne and Jade. They had listened to me and agreed to sell me some of their stuff. I was taking just enough to satisfy me for a week. They were not interested in selling me small quantities though. If I came back again, they wanted me to take enough to sell on to other gals at the club, other customers, heck, anyone I wanted to. If I wanted weed and coke from them, I had to pass some one. When we talked price I realized that I could make enough money that the stuff I used myself would pretty much be free. I liked that idea. I did not take a larger quantity with me this time, because I had not brought enough cash with me for a larger quantity.

Jade also wanted me to service her the same as I had seen Karen doing for her. So she took me into her messy bedroom and spread her large black legs. I got on my knees and soon after I wound myself licking and sucking on the largest, and smelliest, cunt I had ever buried my face in. I remembered what else Karen had done and soon I had worked several fingers into Jade's quim, and them, folding my thumb in to my palm, I buried my entire fist inside of her. I had never done this to anyone before. There was some pressure around my wrist itself but my hand felt very flexible. I was able to turn my hand anyway I wanted. I was also able to open and close my hand. Moving my hand back and forth, and changing the shape of my hand brought moans and groans from Jade.

While I was kneeling, I felt my skirt being pulled down. Looking back I saw that Dwayne had his cock out and I knew what he intended. I wanted to resist. He looked just as skanky and strung out at the first time I saw him. But with my fist buried in his girlfriend, I could not really get away. And I did not want to piss off the people who had just agreed to start supplying me with the drugs that I needed. So I resigned myself and did not fight when Dwayne pulled my panties down.

I heard him gasp when he saw my erect cock. I guess he had forgotten my little secret from when I was there last. But he was doped up enough that he did not care. It would have been nice if he had used some lube, but he place his cockhead at my sphincter and pushed himself inside. My ass was still tight, but it was now loose enough to take in a dry cock.

I did go back the next week with much more money. Each time I went back, I tried to buy as much weed and blow as I could so I could go longer without having to get fucked by Dwayne.

I was curious about fisting though. A couple days later Cherry and I were both lounging around the apartment. I pulled out some weed and we smoked a couple of joints together. We cuddled a bit and I let Cherry fondle and suck on my tits. I moved down to her pussy and began to suck and lick. I used my fingers on her clit, then as I flicked it with my tongue, I inserted two, then three fingers into her pussy. I tried to work four into her, but she told me to stop. She asked me what I was doing and I told her what I had done with Jade.

Cherry said she had no desire to have her pussy stretched by having a hand in there, but did express some curiosity about my ass. So we changed positions and she grabbed a bottle of lube and my large dildo. Soon she had me on my back, with pillow under my ass and my butt high in the air. I needed to watch this! She vigorously shoved my dildo in and out of my ass. She swatted playfully at my erect cock, but I wanted her attention on my ass.

She removed the dildo and lubed up her hand. She worked two and then three fingers inside of me. Then she folded her fingers and thumb as tiny as possible, and twisted her fingers around and around in my asshole, slowly pushing in. My ass resisted, but it had taken several thick cocks in its time and without too much effort, Cherry's wrist passed the resistance and her entire hand was suddenly in my ass!

I felt so fucking full! The feeling was both incredible and... weird. Cherry kept pushing and she manage to slowly get about half of her forearm inside of me! But the best part was when she flexed her hand, and then twisted it as she moved her hand in and out of me. The sensations were like nothing I had ever experienced from a cock. And then on one of her twists, she rubbed against my prostate and I almost fainted! My hard cock spurted its load all over my chest and face!

I gave her directions.... in a bit.. out... around a bit... and finally she had her fingers rubbing against my prostate... She massaged and squeezed my ass lining right at my prostate. I moaned and came a second time in two minutes! Oh fuck, was it intense!

I had to tell her enough.... enough! And she pulled her fist out of my ass with a loud plop. That was absolutely incredible and I knew that I was going to have fists up my ass many many more times!

Chapter 34 - Moving On

Life in Springfield was good for about six weeks. I was making lots of money at the Cradle. I was seeing lots of customers on the other evenings. I was not fucking as much as I had been back in Bigelow, but it was much more rewarding!

I was also making good money pushing weed and coke to regular customers.

Troy and I were getting along great online and I was hoping to visit him in LA in a week or two when he would be done his latest tour. Then out of the blue, he asked me to move in with him in LA. He said that there was a porn film producer whom he was doing work for - mostly gay films, some bisexual, who wanted to hire some shemales for his stable. Troy had showed him my latest pics and the guy was eager to have me in his films.

Troy and I had got along great for one evening and the next morning. But I had no idea if I was ready to move in with him! I told him I needed a few days to think.

I really meant to get back to him the next day, but it turned out it took me a week since I could not get to a computer before then.

That was on a Saturday and I danced my usual shift at the Cradle that night. As usual, I took along some coke which I sold on to some of my regular customers when they took me upstairs. I made terrific money from some of these guys. I took them upstairs where they put money on the dresser to fuck my ass and my mouth, and then afterwards they gave me even more money for a baggie with some white powder in it!

Towards the end of the evening, I was approached by one of my regulars who introduced me to a friend of his. My regular was looking a bit nervous, but I didn't pay much attention. I took his friend Jimmy into the back room since he said that tonight he was only interested in a lap dance. Jimmy was enthusiastic as I ground my ass on his hard cock. He paid me extra to suck on my hard tits and twist my nipple rings. When he paid me, he said that his friend had told him I could supply him with a bit of weed, and some harder stuff. I told him... maybe, but I did not have anything with me. (That was the truth, I had sold on all the stuff I had brought with me that night)