The School Tramp

I was going to clean myself up and call Carlos to drive me home, when I realized it was still only nine pm - I could still safely stay out for another couple of hours.

There was a bar just down the street from the hotel. I fixed up my makeup, put on the blouse and skirt that I would have worn if Doug had taken me to dinner and I went out to the bar. I would I would have one drink and then I would head home. I left my bag and boy clothes in the room.

In the Kat Klub, I sat at the bar and ordered a cosmopolitan. I lit a cigarette, crossed my legs and looked around the place. There were maybe a couple dozen people there, most talking to each other, although a few guys and gals seemed to be on their own. A couple guys gave me questioning looks and one even had the bartender give me another cosmo. The guy was probably at least forty and had already had a few too many. He came over and sat beside me. We chatted and I eventually realized that he thought I was a hooker. He confirmed it when he asked me how much it would cost him to fuck me for an hour.

While I pretended to think about his offer, I lit another cigarette and took a closer look around me. I realized that many of the girls in the place were most likely hookers and most of the men were potential customers. This was not the innocent bar I had taken it to be.

I told him that I was not interested... tonight. In fact, his offer was tempting but I had to get home sooner than an hour long fuck would permit. And besides, I wasn't sure that I felt safe.

I left the bar and on the walk back to the hotel I asked Carlos to pick me up. I suggested though that he park and come up to the room, since I could give him his blow job up there much better than in his cab on the way home.

Five minutes later Carlos was squatted in a chair in the room, holding my head down onto his cock as he fucked my face vigorously. He was grunting and groaning and telling me I was a prettyboy, and that all sissy boys need a man to fuck their faces! But before he came, he pushed me off of his dick and I went sprawling on the floor. He picked me up and threw me on the bed. Before I could react, he had ripped my stockings as he roughly pulled my panties down.

He pushed me face down onto the bed and positioned my ass so that is was high in the air. Then he surprised me by pulling one hundred dollars out of his pocket and waving it in front of my mashed face. Is this enough, he asked? I said yes and right away he pushed his cock into my ass! He had no style, but he had stamina. He pushed and pulled, thrust and pistoned his dick in and out of my ass for the next fifteen minutes. He pushed me down on the bed, bent me over the table, pushed me up against the wall. We were all over the room as his cock pounded me. But finally he jammed his cock into me hard, and he jetted his hot cream into my bowels.

Almost instantly he became meek again and kept apologizing for being so rough. He even tossed another fifty dollars on the bed. I told him that I would need ten minutes to change and he should wait in the taxi.

Ten minutes later I was back in Carl mode carrying my Sindy bag and with an extra $170 in my pocket that had not been there at the beginning of the night. My nest egg was growing! I hopped into the back seat of the cab, leaned forward and gave Carlos a peck on the cheek and then leaned back as he drove me home.

Chapter 20 - Detention

The other night Principal Henderson has whispered in my ear that I would have detention on Wednesday after school. Well it was not quite detention, just a call to his office which was handed to me as a note during the day. As the final bell rang, I grabbed my Sindy bag from my locker and went to the school offices. I had to wait on a hard chair for ten minutes outside his door while he finished up with some other students.

When I was let into his office he surprised me by having me sit in the chair across the desk from him, and then talking to me about my grades. He asked me what I had planned when I left high school in a year and a half. I told him that my mom did not have much money, but I hoped to get a scholarship to go to university to study chemistry or biology, or maybe even some kind of engineering.

Looking in my file, he shook his head. He told me that up until this year my marks would have qualified me for a scholarship, but at the moment every one of my teachers was reporting a failing grade this year. I HAD realized this, but I could not tell him that I was no longer studying at all because instead Sindy was out chasing men to get them to fuck her!

He then asked to see the bag I had brought along. I opened my Sindy bag and he inspected the makeup, the bra and nylons and basic girl clothes. He came out from behind is desk and locked his office door. He then sat on the edge of the desk in front of me and put his finger under my chin and lifted my head. Lovely eyes and lips he said. He handed me the lipstick and told me to put some on. As he did so he pulled down his pants and shorts and his stiff cock bobbed in front of my face.

He said that he did not think that he had ever had sex with both a mother and her son before. He then pushed his cock into my mouth and I began to suck him.

While I bobbed my head on his cock he told me that he thought he could solve my marks problem. He asked me if I had heard that Becky Winters had left school. I had noticed she was not around, but thought she was sick. He told me that she had become pregnant and that she and her boyfriend Dwight Moore were going to get married and had decided it would be best if they moved to another city. They were hoping it would be a nice black baby, so that Dwight could be confident he was the father, but Becky fucked so many other guys, that they would never ever be sure.

This left a problem though. Becky had been having regular sex with several of the teachers and they were all asking the Principal to find them a replacement who would be able to satisfy their needs but also be able to keep her mouth shut, well, other than when it was filled with cock.

Principal Henderson asked me if I would be interested in filling that position. In return, they would promise that my grades would be good enough to get my scholarship, even if I failed every single exam that was set for me.

My mouth was full of his dick, so I just smiled and nodded. When I could I asked him what he got out of this? He laughed and said that he was just a broker in the deal, but he got a commission - which meant that once a week he would want my services. He might ask me to suck him off under his desk, or he might take me to a hotel for an evening.

He asked me if it was going to be a problem, what with him dating my mother from time to time. Would I have a problem being fucked by my mothers-fucker, so to speak! I told him it would not bother me at all. I actually found it to be kinky, I told him.

He then pulled me to my feet and asked me to put on my nylons and heels. He also handed me a school cheerleaders sweater and skirt. He said that I should not bother with the panties.

I also lubed up my ass and two minutes later he had me bent over his desk and was ramming my bum with his stiff rod. Only a few minutes later, he spilled his seed inside of me, and a few minutes later I was out the door.

Over the next couple of weeks I had my first encounters with each of my teachers. These were mostly in their classrooms behind locked doors. The teachers who were not married generally took me back to their homes, and one rented a hotel room.

None of my teachers was interested in my boy equipment, and it did not bother any of them either. I did get compliments on how much tighter my ass was than Becky's pussy. I gathered that a few of them had similar arrangements with other students too, but I did not really care. What I cared was that I suddenly had an even wider assortment of cocks available to fuck me silly! Principal Henderson thought he was helping out his teachers, but he was definitely giving me more of what I wanted! Cassie had called me a cockhound, and she was right!

This is where I have to stop telling you about every single one of my meetings, but rather to just hit the highlights. But you can be assured that I now had at least one fucking every day, sometimes two and sometimes more, with plenty of sucking and my own cum spurting mixed in!

But I will tell you a bit about some of my teachers.

Mr. Jenkins was the most traditional. He wanted to sit and cuddle and kiss with Sindy for awhile before I went down on him and he eventually porked my butt!

Mr. Konstantin never fucked me. He did like me to suck him, but mainly he just wanted me to wear nylons and rub his cock between my feet until he gushed his cum!

Mr. Carpenter would fuck me sometimes, but really he just liked to watch me suck his cock. He liked me to wear bright lipstick and to be sure that I left lots of it on his cock as I slurped on it.

Mr. Strickland must have thought he was an old English professor. He mostly wanted to bend me over his knees, pull down my panties and whack my bottom with a wooden ruler. Of course, he also eventually worked two or three fingers up my ass in order to make me squirm.

I even serviced Mrs. Bumgartner. She was an elderly crone and I winced the first time that she told me I had to eat out her wrinkled pussy. But it quickly softened under my tongue and she was quite tasty. And she sure knew how to use a strap on. I think she fucked my ass better than any of my male teachers, the only disappointment being that it was cold rubber ploughing me, rather than warm flesh!

Chapter 21 - Baked

As I mentioned, from now on I am not going to tell you about ever single bit of sex I had. I am just going to hit the highlights. I now was seeing my teachers and several of the guys from my pimped out orgy that Johnny had arranged. Plus word seemed to be leaking out and I was getting emails from strangers looking to hook up. My own classmates were starting to look at me peculiarly and so I wondered if there was gossip around the school.

I was having my weekly jab of hormones from Coach and I could feel the hormones working inside. I had also started tweezing my eyebrows and had gotten my hair coloured even lighter. I still had to wear Carl clothes to school of course, but I now found myself having better taste, and with a bit more money in my pocket I had improved my wardrobe. However I realized that all of this was making Carl look much more effeminate. And you know what, I did not care!

Christmas was coming up very soon and I had gotten out and picked up some nice presents for mom and Cassie. I wondered what they were going to get me.

On the Saturday before Christmas, the whole family was going out, but separately.

Mom was being picked up by one of the women from her office and they were going to a Christmas function at her boss' house.

Cassie was going out somewhere with Johnny. I barely said anything to Johnny these days. A couple times when he stayed overnight with Cassie I heard him tapping lightly at my door in the wee hours, but I just ignored him.

And me... well, it was going to be a girl's night out. Karen Henderson was picking me up in her car and we were going to go to a bar and dance the night away - me looking for a cute guy to fuck, and her.... well, she would be looking for a cute gal to fuck!

Mom was gone early which gave me time to get dressed at home. Karen came over early enough to help me with my makeup and once again she had me looking pretty slutty. That was fine with me. I wanted the guys to know I was hungry for them! Karen also helped me lube up my ass and insert my butt plug. She thought it would be a real giggle to see me squirming all evening!

We never made it to a dance club. We did not drive into Springfield but rather drove only as far as Seneca. I soon figured out that Karen was again making the rounds, dropping off weed to various of her customers. We smoked a couple of joints in the car and eventually we stopped off at the Kat Klub for a couple of drinks. I had mentioned the place to Karen and she was curious to see it. We were there for only a half hour but we were approached by several guys, first trying to get into our panties for free and then offering us money. One older guy was particularly cute and so I let him take me out to his car and I sucked him off for forty bucks. But we got out of there soon after. The other gals in the place were giving us hostile glares. I suspected they were regulars who did not like competition from young amateurs.

I found I liked being able to put a bit of extra money in my purse and figured I would be back.

Both of us were a bit drunk but the weed was wearing off. Karen just drove us a couple miles out of town to Blueberry Hill, a lookout point that was popular with our classmates. It was a bit early and there were only a couple of other cars there. Karen fired up some kind of bong and we both took a couple of strong hits. We talked a bit, cuddled a bit, made out a bit. We had more weed. Soon I got soppy and began crying, telling Karen that I was all confused. Sindy was taking over my life and I liked it SO much. I just wished that Carl could go away forever.

We toked some more and the car became thick with fumes. We were totally ripped, stoned, baked! Cars around us came and went and we just sat there and talked about my family life, her family life, the woman who had first seduced her, how strict her father was, how she had gotten into selling weed.... just good girl talk. With some heavy petting tossed in. Occasionally Karen would reach into my panties and grab the base of the butt plug and move it about inside of me, making me squeal with pleasure.

I played with her large gorgeous tits for awhile. It made me realize that I really did want breasts of my own. But visions of Becky Winter's rock hard fake jugs kept coming to mind. Karen's boobs were nice and jiggly and fun to play with, but Becky's bullets had slut appeal!

I was nuzzling and sucking on one of her nipples and Karen was moaning softly when I heard a sudden knocking on the car window. I looked up and was surprised to see a female cop peering in the window and beckoning Karen to roll the window down. I looked out my window and there was a male trooper, shining a flashlight in the window! When Karen opened her window a cloud of sickly sweet funky air hit the female cop in the face and she coughed!

A few minutes later, I was sitting in the passenger seat of the cop car with the Patrolman Dick Hooper while Karen was in the back seat of her own car with the female officer. In the cop car the officer asked me my name and asked me for my identification. I told him my name was Sindy. When he asked me my last name I told him it was Barton. He took a close look at me and asked me if my mom was Miriam Barton from Bigelow. I said yes and he said he thought that Miriam's daughter was named Cassandra, not Sindy.

I giggled a bit, still quite high from the dope we had been smoking. Office Hooper asked me what was so funny. When I tried to hug my pocket book close to my chest he took it from me forcefully and searched it. He found a joint, which he put into his shirt pocket, and then he found my id. His eyebrows raised when he read that my real name was Carl. He again took a hard look at me and then nodded and handed me back my purse. He asked me if my mom knew what I was up to. I giggled again, and said no.

I thought I was in serious trouble, but then a grin broke out on his face and he told me to relax. He took the cop car's lighter and lit up the joint, inhaling deeply. He told me that he and his partner were off duty and they had arranged to meet Karen up here to buy some weed from her. She was their supplier too. His partner was a lesbian and so was having a bit of fun with Karen in the other car as well.

He looked at me and said that he might have asked me if I was a lesbian too, but, now that he knew my secret, he wondered if I was more interested in men than in girls! He leaned over and kissed me at the same time forcing some of the weed smoke into me. We sat there and necked for awhile. Dick had a full mustache, which tickled me. It was the first time I had ever kissed a man with facial hair, other than just stubble.

He asked if he could see my cock. I pulled down my panties and held my skirt back so he could see and stroke my dicklet. He continued to kiss me as he teased my cock head. Then he noticed I was squirming. Reaching lower down he discovered the plug in my ass. This amused him.

He pulled my head down into his lap and released his cock from his regulation trousers. It was already quite stiff and I mewed and giggled again as I opened wide and took his dick all the way down my throat on first gulp. He gasped at how far down his cock my face had plunged, but groaned encouragement at me. For the next five minutes I licked and sucked on his gorgeous meat stick. But I wanted more.

While Karen and I had enjoyed ourselves that evening, I had gone out expecting to find a dick to fuck me and finally I had one in my grasp - we, in my mouth at the moment. I managed to lean Dick's seat back enough that was able to straddle his lap and then I sat down facing him, letting his cock slide into my boycunt that had been held open by the butt plug that I had just pulled out and flopped onto the passenger seat.

Dick's cock was fairly thick and felt oh so very nice as I let myself sink down on it. Dick grabbed my ass and helped me to raise and lower myself on his cock. It was awkward because I had to lean against him since the roof of the car did not let me sit fully upright on him. I squeezed my ass muscles and shimmied my butt on his lap for the next ten minutes. Just before Dick spurted his cum into my ass, the car doors opened and Karen and the woman cop both peered in to see what we were up to. Karen stroked my arms and murmured encouraging words as I fucked myself on Dick's... well, on Dick's dick! Finally I let out a soft moan as my own cockette spurted my cream onto Dick's chest. With this, I clamped my ass hard around his pistoning cock, and he shot his wad deep into my boipussy!

I retrieved my butt plug before the cops drove away. Karen and I helped each other get dressed again. I noticed that she had a violent hickey on her neck that I had not left there. We were both tired, but were much more sober and less stoned after that experience, enough so that Karen felt comfortable driving me home. But she was not in good enough shape to make it back to her own house AND past her sleeping father. So Karen came upstairs with me.

As we crept up the stairs, I could hear a lot of noise from both my mother's room and from behind Cassie's door. They had both gotten lucky and brought men home with them. I cleaned off my makeup and climbed in bed with Karen. We kissed a little bit, but we were still both pretty buzzed and we each slowly drifted off to sleep. I was on my side with Karen spooning me from the back. It felt so nice to have her big soft pillows against me.

In the morning I heard lots of activity from other parts of the house as Karen and I slowly woke up. There was a knock on my door and Cassie poked her head inside saying that breakfast would be on the table in fifteen minutes. We both quickly washed enough to be presentable. Karen dressed in her clothes from the previous night and I put on some good Carl clothes..

When we got to the kitchen, Mom beamed with delight as I led Karen into the room, hand in hand. I was surprised to find four women in the kitchen already. It turns out that Mom and Cassie had each brought home a woman lover last night. Mom was sitting beside Mrs. Morton who worked with her but was not the co-worker who had picked her up last night. Cassie was passing some toast to Angela Simpkins, a cute girl from my junior class who was looking rather smitten with Cassie.