The School Tramp

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He asked if he could get some from me another night, and we made a date for him to come by my apartment the next night. I told him how much money to bring and that the price included him paying for a round of fucking my ass, since I thought he looked cute.

Sunday night Jimmy showed up on time and although I rubbed up against him a lot, he was only interested in the coke. So I took his money, gave him the baggie and he was out the door. A minute later there was knock and I figured he had changed his mind. I opened the door to find Jimmy, and two uniformed cops. Jimmy showed me his badge and then the three of them ransacked my place. They found a lot of coke and weed since I had only just gone to see Jade and Dwayne the day before!

I was arrested and taken down to the precinct house. Once I was processed I ended up in the city jail. I called a lawyer - one of my regular johns. He talked to me, and then passed me on to a guy who cost a hell of a lot of money. I was in jail for three days, including being up before a judge for the charges to be read. I had to go THREE FUCKING DAYS with no cigarettes, no weed, no coke.... and no makeup!

I was looking at serious charges for possession and distribution. I told my lawyer everything and he was able to make a deal. I got immunity from prosecution and from testifying. But in order to get that I had to give up Jade and Dwayne as my suppliers. Once the cops raided and busted them I was free to go. Oh, and though I didn't have to, I gave up Karen to as one of my suppliers.

The next day the papers had stories about the major raids. One ran a picture of Karen being led away in handcuffs. The article also mentioned that several cops had been arrested, naming Dick Hooper and his partner in particular.

I knew this state was going to get very hot for me.

I phoned Troy and told him I was moving to LA!

I packed my bags, gave Cherry a big hug and caught the first plane to California!

Epilogue

This is where I am going to end my detailed story. In a ten month period I had gone from being a nerd with my nose in my books, to being an oversexed anal slut bimbo shemale with my nose constantly in white powder!

I moved in with Troy in West Hollywood. I did go to work in porn films. I started in a few bisexual videos, and soon graduated to several shemale lines. Troy was my partner in many films, but he was also very much in demand for gay movies as well. It seemed he loved having his ass pounded by thick hard cocks just as much as I did!

I soon got well known for being fisted regularly in my films... first just by gals, but then by men, and soon I was taking very large objects up my ass in specialty fetish videos.

While starring in these films I was enjoying the fringes of the Hollywood scene. I got friendly with several stars of tv sitcoms and various films. I was seen on several red carpets before movie premieres, and I was fucked thoroughly by some big hollywood names.

I paid good money to have a fancy website that promoted my porn career, and my outcall services. I often made a thousand bucks a night from just one rich john. I found myself flying to Europe a couple times, to be the trophy girlfriend for a long long weekend.

Troy and I were getting along well. I loved the way he pounded my ass on film, and he was a wonderful and caring lover when we were home together. He was often on the road though and so I was on my own a lot. He did not mind that I was selling my ass and mouth to earn a living - he was too!

Life was fantastic for about a year and a half!

However, I was living life very large. I was drinking a lot and using a lot of coke, ecstasy and any other drugs that came my way. There were many times when I would wake up without knowing what I had done the previous twelve hours.

I began missing my shooting schedules, or showing up drunk. Punters would phone me up after seeing my website, but I would then not show up or would not look my best. I got a bad reputation on online reviews and the calls from my website dried up.

Troy tried to help me, but he was not around enough. And I resented him for being sober. One time I called him a sanctimonious bastard and slapped him. Two days later he was in a car accident and he died! I totally fell apart at that point. I still had a drop dead body, well, mostly. I had put on twenty pounds of weight. At five foot six, that was a lot, and my tummy and face showed it! No one wanted me in porn films due to my drinking, drugs and memory problems. I swear I no longer had to act the part of a dim witted bimbo. The weed and drugs had burned out an awful lot of brain cells!

I found a low budget guy and started doing fetish videos for the internet. These involved me taking large dildos up my ass, and also lots of self fisting! My vids were popular and I made some good money from the passworded website. But a lot of my videos got pirated and ended up on torrent sites for free and my income shrank again.

At nights I began working the street corners with the other shemale hookers. There is was easy to pick up johns, but I was not making the money that I used to! I usually ended up the night slouched over a bar in some dive and finally going home with whoever would pay my bar tab for the evening.

I'm not going to tell you about the next six months. Just take it as given that I sank about as far as a human being could go - I started being able to tell different brands of dog food apart at my lowest point.

I finally ended up in AA. At the same time I had a couple of surgeries to sew my ass back together. I had regular prolapses as a result of all the large objects pulling my ass apart.

In AA, I went through all of the stages, including making apologies to all the people I had hurt along the way. This meant begging Cassie for money and travelling back to Bigelow and Springfield. Mom had died a year or two earlier. Cassie greeted me tearfully and I met her new husband and her baby son. I visited Karen in prison. She did not want to talk to me, but faced me through the glass long enough to spit at me.

Jordan Henderson had moved away from Springfield. Coach Grogan had survived all of the scandal and was now principal.

Stevie had not followed in my footsteps completely. He, or rather she, had abandoned the Mink name, and was now known as Stephanie. She was still a bit of a slut when it came to men, but she was able to control her urges. She was a chemical engineering major at State University at Springfield.

Most surprising, Johnny Long held no grudges towards me and thanked me for apologizing to him.

I returned to California and continued my recovery. I discovered that there was government funding for sex change surgery for people in my financially distressed condition. I still loved being fucked, but could not endanger my ass and my life anymore. As much as I loved my cock, I made the decision to have SRS. At the same time I had my giant bosom reduced down to much more modest levels. I also had laser therapy to erase or obscure my more lewd tattoos.

I kept in touch with Cassie and also, strangely with Johnny. Johnny even came out to visit me while I recovered from my SRS.

When I was fully healed, I visited Bigelow again and I seduced Johnny. He was the first man to fuck my new pussy, and he was just as sweet a lover as I remembered.

My Johnny. My first love. Well, my first crush.

Johnny and I got married and I moved back to Bigelow. Only a few people knew that the new Mrs Johnny Long used to be Sindy Barton, or Carl Barton for that matter.

Cassie was happy for me. Cassie, the sister who had made me the woman I had become.

The End

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AnonymousAnonymous4 months ago

This is actually quite a good story. Carl (Sindy) Barton comes across as a vivid character.

What's fascinating about the transformation from Carl to Sindy is how much self affirmation and power Carl gets from it. Carl starts out as a young man with serious confidence and inhibition issues, he's lonely, intimidated by life, intimidated by everyone, living a sexless life. Carl lives a life of unrequited desire, he wants to be desired, but no one wants him, not even himself.

Then, when he assumes a female role, becomes Sindy, suddenly, someone wants him. Everyone wants him. He's desired and desirable. That's amazingly powerful. Sindy gets pleasure from being fucked, she enjoys the experience prostate massage, and it's a formative first experience. But the pleasure of being fucked is second to the mind blowing charge that someone wants her, she gets second looks, she gets desire, it's the real drug for her.

It's interesting the power she gets from being a slut. She's completely amoral about it, completely hedonistic. But no matter what she does, or who she does it with, ultimately, she's always in control, it's all about her and her power. Even she's whored out by Johnny to a gangbang, she chooses to go through with it for her own power, and then she rips Johnny a new one, takes his money, and takes his power. No matter what she does, no matter what degrading acts, she takes power from it. She's never a victim. People try to use her like a whore, but she refuses to be used. She uses whoever uses her. She's the goddess that their pricks worship.

For Carl, being Sindy delivers everything she ever wanted or needed in spectacular ways. In a sense, she's super-addicted. Even the downside - the prolapses, the drug and alcohol abuse, the downward spiral into the gutter, she's still chasing being desired, still expressing power. All her mistakes and self damage are freely chosen in the pursuit of that self affirmation, of being desired, of having power over her life.

The only thing even a little false is the eplogue where she settles down and becomes a good little wife. Someone like Sindy might grow up and mature, but don't think she'd ever settle. I think she's pursue her drives, simply in less toxic but more managed or controlled ways. I could see her graduating to club owner, or porn director, or just finding a way to get up to higher level.

But excellent story, and hot as hell.

AnonymousAnonymous4 months ago

I read your recommendations in your notes after Predator and Prey chapters. One was this long story which I loved!! Yes, downbeat, but appropriately so. So well-written. 5 stars!!!

AnonymousAnonymousover 1 year ago

If anyone doubted Carl/Sindy was thinking like a woman, she got back with the first boy who treated her like shit. Basically, every woman I've met. Praise Kek.

AnonymousAnonymousabout 3 years ago

I have wrote on here before, I don't take back my comments on Sindy as the human being she ended up being. I wish her mom would've supported her in with Sindy wanting implants. Everything fell apart and I wish Cassie was the one who brokered the peace between them. Wish Johnny did not get a free pass for his cheating and pimping Sindy out. Wish Cassie would not have given Sindy a free pass like Karen did.

LuganisLuganisalmost 6 years ago
Great, good & depressing

The title describes the sequence of this great story. A lot has been said in the previous comments, but I will summarize

- To long. Would have been better to write as a series.

- Not really descriptive. Could have given amazing sex scene descriptions. At the beginning there were at least descriptions of the characters.

- The school’s slut disappeared from the story to fast.

- Carl got hooked to fast. Becoming a sissy (Sindy), then a prostitute, drugs. There is no psychological/emotional change.

+ Well written & easy to read.

+ Not many typos and grammar.

++ Very hot story. The story kept me aroused until the last chapter.

++ Shows how sex is an addiction, and anal sex is even more.

+ Presents the social bisexuality denial

++ Presents the dark side of human beings, from school bullying by teachers, “success”, the struggle to be on top of the pyramid, the need of power and greed.

++ Presents how a joke can change more than just one life

I like very much the story. It seems like a script for a 90210 style TV program.

My suggestion, write it again, add some of the elements mentioned in the comments and I believe it could be an even better story

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