The School Tramp

Karen and I drove into Springfield together early in the day and did some shopping. We also met up with her supplier. This was at a house in one of the rundown sections of the city. We went inside and were met by Jade, a large black woman and her husband Dwayne who were in their thirties. She was a nice looking woman but decidedly on the heavy side. Apparently money was not the only payment Karen was making today. Jade led Karen into the next room, where she lay back on the bed. Karen knelt down and soon had her face buried in the fat woman's quim, eating her out.

From where I sat on the couch, I watched as Karen slobbered over the very meaty cunt, and then watched as she also used her fingers to flick Jade's clit. This soon turned into Karen sucking the clit and shoving a couple fingers into Jade's cunt - which became three fingers, then four, and then I watched as Karen folded her thumb into her palm and slowly pushed her entire fist into Jade's pussy. Jade squirmed about as Karen flexed her fist inside the black cunt, slowly rolled her wrist back and forth and then began to fuck Jade vigorously with her fist! God, but didn't that look... interesting. I wondered what it would be like to have cock in my ass that could squirm around that much. I wondered what it might feel like to have a fist in my ass! I guess that was possible!

As I watched this, I sat on the couch sharing a reefer with Dwayne. It was some damn good shit. He kept trying to put his hand on my thigh and suggesting that we go upstairs to another bedroom. I might be a cock slut, but I was not crazy. This guy's face was pock marked and his arms were covered in needle tracks. I was definitely not interested. He persisted and got more aggressive and finally I pulled down my panties enough for him to see my cock! That made him move to the table in the dining room!

Karen finished with Jade, who lay back panting as Karen used the bathroom to wash up.

Karen was careful with her driving after that, not wanting to get stopped for a traffic offense and perhaps have the car searched! Of course we sampled the weed and just before dinner we both snorted a bit of coke. Hey, it was my birthday! I deserved a treat!

We met Mom and Cassie at a nice restaurant. I had a couple of drinks and perhaps got a bit unruly. Especially when Cassie went on and on about Johnny. Cassie was again talking about how she and Johnny might get married soon. School would be over in a couple months and they would both be graduating. Cassie's marks were not good enough to go to college, but mom had arranged for her to get an office job in Springfield. Johnny would be going to college there and so they had talked about getting married and moving into married student housing there!

I of course new 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 boyfriend she would just ignore me. I held my tongue at dinner as much as possible, but I did let a couple of comments escape in side whispers to Karen. Mom looked at my sternly and decided it was best to pay the bill and get out of there, hoping to break that line of conversation.

The Cradle was only two blocks from the restaurant and so we walked. Mom and Karen had both parked in a parking garage between the two places. I was a bit unsteady on my feet, but I linked arms with Karen and we made it fine to the club. Mom was a bit frustrated at having to stand around outside the club while Karen and I finished our cigarettes.

Inside we had a reserved table for four near the front. They did not normally reserve tables, but Cassie had called ahead and told them that it was my birthday, so they had made an exception. When we arrived they checked our ID, and my new Cindy identification still had Carl's birthday on it, today. It seemed unusual that there were ushers in nice suits, but one of them who introduced himself as Troy led us to our table. He was tall, handsome, not much older than I, and well built. He complimented me on my looks, wished me happy birthday, and definitely ogled my tits. I could almost see him drooling. I turned my face to him and let my airhead personality take over. I giggled and asked if I could feel his muscle. He held out his arm, and bent it making a large muscle. I said not THAT one and giggled again! Being a sexy tease was such fun!

A couple minutes later the lights went down and the dancers/strippers came onstage. I realized then that the waiters/ushers WERE the strippers!

What followed was seventy-five minutes of yelling and screaming from the all-female audience as eight handsome hunks took the stage one at a time, and in groups, stripping down to almost nothing in time to steady thumping beats. Waitresses wandered through the room, replenishing drink orders and cleaning up the empties. I had two or three more cosmopolitans and was definitely feeling no pain!

The guys stripped right down to tiny briefs and thongs which covered their cocks, but did not hide the shape or girth. I guess there was some kind of law that said they could not be completely naked, but what that law was I was not sure. Then the host made an announcement that if the women made enough noise, the guys had a special treat for them. Spotlights showed that all of the doors were being closed. I realized this was for show, but it was quite effective.

Then all eight dancers came out on stage, fully dressed and began to wander through the audience, touching the women on their shoulders and elbows, and allowing the women to grope at their crotches. As the music continued the guys danced amongst the tables slowly removing their clothes until the only thing they were wearing was their tiny briefs. They all made their way to the stage, turned their backs to the crowd and suddenly tore off their tearaway briefs. Then they turned back to the crowd of hollering and hooting women to proudly display their might erections. None of the guys were smaller than six inches; all were thick.

I did not know where they had come from, but each of the guys had a can of whipped cream in his hands. They all spread out amongst the audience and each guy approached a different table. He would squirt a little bit of whipped cream on the tip of his dick and stand in front of a table. If one of the gals there motioned, he would step beside her and... well, some of the gals giggled and swiped the cream off quickly with a finger. Some women would take hold of the knob and scoop the cream off with her hand, before the guy reapplied the cream and faced the next gal at the table.

Some women were bold enough to lick the cream off of the cock. When they did that, the guy would apply more whipped cream and offer his cock to the same woman again. Most just blushed and turned away.

I was having a wonderful time, shouting and encouraging the women at the tables around us. I was quite plastered at this point, almost falling out of my chair at times.

And then Troy approached our table. Troy had a beautiful cock, and an interesting cock! It was eight inches long and it flared - it was narrower at the base, then thickened in the shaft, before tapering a bit again, reaching the nice mushroom helmet. He sprayed whipped cream on the tip and then presented his cock to Karen. Karen just shook her head. He swivelled to Cassie and Cassie put her hand around his cock and licked the cream off, her tongue not really touching Troy's cock. She giggled as she sat back, and Karen hugged her. Troy looked disappointed.

Troy reapplied the cream and approached Mom and raised an eyebrow at her. I had figured mom would shake her head, but she had also been drinking and was hollering along with everyone else. Mom did not use any hands, but opened wide and took the head and an extra inch of Troy's cock into her mouth. As he pulled back out, you could hear a pop from the suction, and then her tongue reached out for a final tickle at his cock head. Mom blushed!

Well I certainly had to outdo Mom! When Troy turned to me, I took the can of whipped cream out of his hand, used one hand to pull his dick down straight, and then squeezed out a thin line of cream from the tip of his cock, along to top to his pubic hair. I handed the can back to him, and he looked at me questioningly. With little hesitation I took his glans in my mouth and then I pushed, and slowly slid his entire eight inches into my mouth and down into my throat.

As my lips nuzzled his pubic hair, the tables around us went silent. I held my position for about thirty seconds, during which you could hear everyone breathing, and then I slowly pulled back, making sure that my upper lip dragged along his cock and cleaned all of the whipped cream off! As his cock left my mouth, all the women around us let out a roar and a loud cheer. I sat back satisfied.

I looked at Mom and she was stunned. I realized that this was the first time she had ever seen me as a sexual creature. Up until then I was her son, then her new daughter, and at times her unruly brat. She knew that I was dating Jamal and that he stayed overnight sometimes. She must have assumed I was having sex with him. (She certainly did not know that I was fucking multiple guys every day!) But this was the first time that she had seen me actually have any kind of sex with a guy. It was sinking in on her, that her little boy was now a big girl. And she was about to get an even deeper shock!

The emcee had the lighting guy turn the spotlight on me and asked me to stand. He introduced me to the audience as Sindy and told them it was my birthday, which got some polite applause. He then told everyone that I had just done something remarkable, which the couple tables around us had seen. He asked those tables if they thought the rest of the crowd would be interested in seeing it too, and all the women there yelled yes! He then asked me if I would be willing to repeat what I had done for the rest of the club!

Mom said no, no, but I just stared her down. I put on my now familiar vacant airhead expression and told him, sure! To a round of applause I was led to the centre of the stage. A short bench was brought out and I was asked to kneel on it. Then another one of the dancers, a Latin looking guy whom they introduced as Sanjay stepped forward. I saw that he had the longest cock of all the guys, probably about ten inches.

I took one more look over at my table. Karen and Cassie was watching me eagerly. Mom was staring too, but it was hard to read her emotion. It could have been dread... but I think it was shame and disgust. Quite frankly I did not care. I just knew that I had a nice beautiful cock in front of me. I opened wide, Sanjay moved his hip forwards and his cock head touched my lips. I stuck out my tongue and swirled it around his glans. I then reached my hand out, put it on his ass, and nudged him forward. He lunged a bit, and I took all ten inches down my throat in one gulp.

The women in the audience shouted and stomped their feet as Sanjay fucked his cock in and out of my mouth. I was loving the feeling of his delicious cock and was getting off on the chanting. As we continued, Troy walked up behind me and tapped me on the ass. I stopped sucking briefly. I looked back and nodded that it was okay for Troy to lift my skirt. I lifted one knee and then the other so that Troy could remove my panties.

My cock dangled down, but due to the skirt the audience could not see that I had a dick. Troy's eyebrows raised in surprise, but he was not deterred. I turned my head back again and mouthed, Fuck Me!, and Troy did. He put the head of his cock at my asshole and slid easily inside of me. The music thumped to a lively beat, and all of the women in the crowd were cheering, egging the guys on to fuck me faster and harder. At one point Sanjay pulled my blouse down and freed my tits from my bra. The perfect round globes bounced as I was fucked from both ends!

The guys were true professionals. This was not just a public fucking, but also a performance for the crowd. They ground their hips and were pretty much dancing as they skewered me from both ends!

The boys together lasted about seven minutes. Anything more than that would have lost the audience's attention, and the guys knew how to play to the crowd. Sanjay pulled his cock from my mouth and then used his hand for another half minute, finally blowing several streams of hot jizz across my face. The crowd groaned along with Sanjay.

Troy still had me stuck on his wonderful cock. He whispered in my ear asking permission. I was too cock crazed to care at the moment. All I knew was that my ass was getting a right royal pounding from a superb man dick. I said yes, yes, anything yes, just fuck me!

Troy stood up, lifting my light five foot four frame so that I was in his arms facing the audience, my skirt pulled aside - and all of the women say my own dick standing rigid, and that Troy's cock was shoved up my bruised arse and not inside a pussy as they had expected. The room was silent for five seconds, and then the women started yelling, fuck that bitch, and other obscenities even louder.

I looked over at my table and saw mom putting on her coat. She was still staring at me, but she had a look of loathing on her face! Cassie looked awe struck!

I grunted, I groaned, I shot my own stream of cum high in the air, as Troy raised and lowered me on his dick. Finally, with a low rumble, he thrust me down on his cock and grunted loudly, his face and legs straining as he came inside of me! The audience was quiet... unsure as to whether they had seen the climax of our act. Troy lifted me off of his dick and when he did, his cum ran out of my ass and pooled on the floor of the stage. The crowd erupted!

Troy put me down gently and we hugged. My legs were weak, my knees were wobbly. I gathered up my clothes and turned back to the table, just in time to see Mom pulling Cassie out the door. Karen gave me a hug. I sat down to gather my strength and slowly put my clothes on.

Karen hugged me and gave me words of encouragement, but also warned me that my Mom had been spitting mad at me. I shook it off as no big deal. Sooner or later Mom was going to find out that I was not a sweet innocent virgin girl and now was just as good a time as any.

Karen then apologized saying that she could not give me a lift home. One of the women from another table was lagging behind. Evidently Karen had made a new friend and would be spending the rest of the evening, and all night, with her! I told her it was fine, I would just get a hotel room for the night and get Carlos to give me a lift in the morning.

When Karen left, I sat there for a bit, but the management chased me out, since they had to set up for the rest of the evening.

Outside the door, I ran into Troy who had showered and was presentable. I let my face go vacant and began to cry a bit. He asked me what was wrong and I told him that the other people in my group had run out on me. I was all alone and had no way to get home!

He took me back to his hotel room. We cuddled together for awhile, before I kissed him and he kissed me back. As we sat entwined, he told me that he was bisexual and had sex just as often with men as he did with women. I was a bit of both, and so he was delighted to find me there with him. We soon ended up in bed, and I found myself on my back, with a sweet handsome sexy man, rutting his cock in my back passage for what seemed like an hour before we both shot our loads. We nuzzled and cuddled some more as we drifted off to sleep.

Chapter 26 - A Job Offer

In the morning I woke Troy up with one of my amazing blow jobs. This is when I found out that Troy had a fetish, which was that instead of letting me suck his cum out of him, he found it an incredible turn on to splash his cum across my face. Whenever we fucked, whether in my ass, or down my throat, he always wanted to pull out at the last second and splooge on my face.

When we finished, Troy left the hotel room, saying he was going to find us some breakfast. I washed up a bit and then crawled back into bed. I smoked a joint and then lay my head back. A half hour later I was awoken as he placed a tray of food on the bed.

Troy asked me how I had gone from being a boy to being a knockout shemale. I decided it was best if I continued to play the dumb airhead and so I told him, in small words, that my sister had tricked me into it and I had found that I liked being a cute girl! And then I found out that I really really liked having sex with guys!

As we talked we ate, and our hands touched as we reached for the same things at the same time. This led to us holding hands while we finished up. When the food was done, Troy moved the tray onto the floor and we embraced passionately. Soon he was fucking my face hard as I lay on my back with my head hanging backwards off of the bed. He was still amazed at how my throat easily accommodated his cock. It did not take long for him to cream his load across my face.

We showered together, which led to him soaping up my ass and driving his cock deep into my bowels. We skidded around in the shower stall, since the floor and walls were all slippery. This time he came inside of me! I chased him out of the shower after that so that I could get myself completely clean - inside and out. After the shower, I had to put back on the same clothes I had worn the night before. I did have my makeup with me.

Troy had to check out of the hotel after that. Downstairs in the lobby we met up with the other guys from his strip act. These guys had a large van which they used to drive them from city to city. Troy had two more weeks on the road before he would fly back to Los Angeles where he lived. Troy told the guys that he was going to spend a few more hours with me, and would meet them back at the hotel at 6 pm, when they would grab some grub to eat on the drive to the next city.

Troy and I walked around for a couple of hours, holding hands, and kissing every once in awhile. Here was a guy who I could really get into, could consider as boyfriend material, and he only came to my city twice a year!

As we talked, I remembered to keep everything that I said simple. Men did not like smart girls, I had found out. So I made sure to keep my words short and pause when talking to make it look like I was thinking hard.

As we talked and I got more comfortable with Troy I told him about my surgery for boobs and fixing my nose and that I hoped to have more surgery soon to intensify my femininity. He said that it must cost a lot of money and I found myself telling him how I had made the money for my first surgery. He was not surprised nor did he tell me that hooking was wrong. In fact, he admitted that sometimes he took money from women for sex, and from men too.

When he found out that I was eager to get my boobs enlarged again sooner rather than later, he said that he had an idea that he thought I would like.

Soon we were back at the Cradle. The place looked pretty dingy in the daylight. There were a couple of staff restocking the bar and one older guy mopping the floor of the stage. Troy led me into a back corridor and knocked on an office door. A voice told us to go in.

A fat man sat at a desk, smoking on a stinky cigar. He recognized Troy and they shook hands. Troy introduced me as Sindy and introduced the man as Mr. Gambetti, the owner of the Cradle. Gambetti sat back down, looking me over and expressed surprise at seeing me again. He remembered me from the previous night.

Troy suggested that Mr. Gambetti might want to hire me for the club. I blinked my eyes in surprise and kept my dumb blonde look on my face.

Troy told us both that he had to leave. He told me that he would be in touch by email. We kissed and then he was gone.

Gambetti asked me if I had ever danced in public before. Had I ever stripped? I told him that I had not, but I was a quick learner and I was not shy in public. Gambetti practically laughed, realizing that any gal who would let herself be fucked on stage was definitely not shy.