Poor Little Cassie - Cover

Poor Little Cassie

Copyright© 2021 by Demonhead

Chapter 12: School

Fiction Sex Story: Chapter 12: School - Young virgin is taken advantage of by plumbers and then it only gets worse. She has many adventures and not all of them pleasant.

Caution: This Fiction Sex Story contains strong sexual content, including mt/ft   Ma/ft   Fa/Fa   ft/ft   Fa/ft   Mult   Coercion   Drunk/Drugged   NonConsensual   Rape   Reluctant   Slavery   Lesbian   School   Incest   Mother   Brother   Father   Daughter   BDSM   MaleDom   Humiliation   Light Bond   Rough   Snuff   Spanking   Torture   Gang Bang   Interracial   Black Male   White Female   Anal Sex   Bestiality   Double Penetration   Exhibitionism   First   Facial   Fisting   Food   Oral Sex   Voyeurism   Water Sports   Teacher/Student   Cannibalism   Nudism   Prostitution  

The week before I went back to school flew by, I slept a lot, I felt like I could not get on top of the fatigue. I guess getting fucked and beaten by a lot of men takes a lot out of you. Each day I felt a little less sore and the day I was leaving it almost did not hurt when I moved. My bruises were fading, and I could finally wear shorts. My legs were back to pretty again and it felt good to at least get out of sweatpants. My breasts and ass were still a little black and blue so no bikinis for a while.

My brothers all left for school during the week, and I cursed Tony again every time one of them left. I could see it in their eyes that they knew I was still upset, but they had no idea what to say or do. I tried to relax and be normal with them but as soon as I did, the image of their cocks sliding into one of my holes flashed across my head. I waved goodbye to them and hoped it would be easier the next time I saw them.

I sat in the backseat as my mom and dad brought me to school. Mom insisted on riding along and I appreciated that, it was nice to have someone that knew a little about what was happening to me. However, I wondered if I would ever be able to tell her that all the men in her family fucked her 16-yr-old daughter. I sighed when I realized that this was one of those decisions mom was talking about. I could not imagine ever telling anyone, it would hurt all of them and she was right in that it would not change anything so why hurt people for nothing.

We pulled up to my school and it was bustling with kids moving in. It was a prestigious high school, and it was very hard to get into. My grades were good, but I was pretty sure the fact that they needed a flyer for their nationally ranked cheer team was what got me in the door. I got settled in my room and we all went to lunch before they got back on the road. I hugged my dad and tried very hard to not think about him feeling my boobs. I hugged my mom, and it was nice.

“Call me if you need anything or you just want to talk.” Mom whispered in my ear.

“I will, thanks, but I should be ok here.” I said, hoping I was out of reach of Tony.

“I hope so sweetie.” Mom said and kissed me on the forehead.

I waved to my parents as they drove away and hoped my life would get back to some sort of normal. I saw one of my cheer teammates and she came running over. I took a deep breath and hoped this hug would not hurt too much.

The next three weeks were wonderful. My body was back to normal, my bruises were all gone and there was no pain. My classes were easy, and I felt like the material just soaked into my brain. However, the highlight of each day was cheer practice. My strength was back, and I was flying high. My bases came back from the break even stronger, and they were tossing me higher than ever. I was in total control in the air and the coaches were very happy.

We had a new assistant coach, and he was tough. He came from a strong college program, and he was in charge of the air stunts, so he worked with the flyers a lot, and he was pushing us hard. There was a new flyer, a small freshman girl, and she was very good and very cute. She was even smaller than me, so she was getting good height as well. The team was working well together, and I was getting very excited about the season. The thing I was most excited about is that I had not thought of Tony or any of the things that had happened to me for at least two weeks, and it felt good.

My world changed one Wednesday afternoon. I was sitting in math class learning about imaginary numbers when an office helper walked into the class and handed my teacher a note. He read the note and called me to the desk.

“Mr. Pennington needs you in the office, check with me tomorrow and I will catch you up with anything you miss.” He said and handed me the note.

I walked down the hall; it was always weird when the hall was empty. Mr. Pennington was our vice principal, he was also the sponsor of the cheer team, I was sure he wanted to talk to me about that. I was not a captain, but I was in my second year and the team was very young so I was taking on a little bit of a leadership role. I walked into the office area and the secretary motioned to the door. I heard voices in the room, and I opened the door. Mr. Pennington was sitting at his desk and no one else was in the room.

“Close the door, please.” He said and I shut the door. I walked closer to the desk and stood in front.

“Is she here?” a voice came from the desk, and I froze.

“Yes.” Mr. Pennington said.

“Princess, come around the desk so I can see you.” The voice again. I walked around the desk and saw Tony on the screen. He smiled his evil smile.

“There she is, pretty as ever. How is school going, sweetie?” Tony said.

“Fine.” I said tersely and he frowned.

“Princess, did your daddy’s car ever get repaired? Do I need to call Carl and get an update?” Tony said, the evil smile again.

“No, it was done, it is ok.” I said in a much perkier voice.

“Good, I want to keep my princess happy. Thank you for coming today. We have some business to discuss.” Tony said.

“What kind of business?” I said and smiled.

“Well, you know this school relies a lot on contributions and support from the community and the local businesses. My buddy Vince here oversees fundraising, and he reached out to me for help.” Tony said.

I knew we depended a lot on fundraising, we had done a few car washes last year and made a lot of money, turns out cheerleaders in bikinis on the side of the road generates a lot of interest. I figured a lot more car washes were in my future.

“Ok, what do you need me for?” I said, trying very hard not to sound angry.

“Well, princess, I am allowing Vince here to use you if he needs any assistance with any of his efforts. I told him you were always willing to help.” Tony said and I didn’t like where this was going.

“So, Vince, do you think you can use her?” Tony said.

“Well, sure, I suppose. She is very young, are you sure she can handle this?” Vince said and Tony laughed.

“Vince, she may only be 16 but our little princess is very capable of anything you throw at her. Sweetheart, take off your shirt.” Tony said nonchalantly, like asking me to take off my shirt in my assistant principal’s office was normal. I looked at the screen and then at Mr. Pennington, he looked as stunned as I felt.

“Sweetie, do you not understand the task?” Tony said and I took a deep breath.

I was wearing a pink cotton halter top that came a few inches short of my white shorts. I pulled the halter up and off. My pink lace bra was now on display. Mr. Pennington was staring at me.

“What do you think Vince?” Tony said.

“Very nice.” Mr. Pennington said. He had known me for over a year, but he was looking at me like he had just met me. I wondered how many fantasies I was fulfilling for him here in his office.

“Oh Vince, we are just scratching the surface. Sweetie, take off that pretty bra.” Tony said and I heard Mr. Pennington take a breath. I opened the front clasp and felt my bra loosen. I slipped it off and put it on his desk. My breasts moved on my chest, and I turned back to the screen.

“Sweetheart, I will never get tired of looking at those tits. Vince, what do you think?” Tony said.

“They are remarkable.” Mr. Pennington said.

“Check them out, they are very sensitive, and she loves it, right sweetie?” Tony said and I nodded.

Mr. Pennington touched my boobs and squeezed them. He touched my nipples and I felt them respond. He was very gentle, and it did feel good. I stood and let my assistant principal feel my boobs. He pulled back and took a deep breath, his eyes never leaving my breasts.

“This is high class trim, Vince, we should be able to make a lot of money off these old rich fuckers if we play our cards right.” Tony said. I saw Mr. Pennington wipe his brow; he was obviously not used to seeing sophomores topless in his office.

“Sweetheart let’s show Vince some of your other talents. Get on your knees and pull that cock out.” Tony said. I tried not to look disgusted and knelt next to my assistant principal. I reached over and started unbuckling his belt. I felt him flinch as I unsnapped his pants.

“Tony, but, we don’t...” Mr. Pennington mumbled.

“Vince, relax, she is very good at this. Let her show you how she is going to suck money out of those old guys.” Tony said. I unzipped him, reached in and pulled out his hard cock. It was not as big as Tony’s, but it was still hefty in my small hands. I leaned forward and slipped him into my mouth. I heard him gasp.

“Good sweetie, do your thing and don’t miss a drop.” Tony said and I continued to suck the cock of my assistant principal. He did not last long, and I had a mouthful of cum in a couple of minutes. I swallowed and felt the slimy stuff slide down my throat.

“Stand up princess.” Tony said. I stood, wiping my mouth with my hand. Mr. Pennington looked at me, his cock shriveled up in his lap.

“Now take off those shorts.” Tony said. I knew I would do anything at this point, my old memories coming back. I saw a vision of Carl walking towards me with the jumper cables. I shuddered and my shorts fell to my ankles, my pink lace panties the only thing left on my body.

“Isn’t that beautiful?” Tony said.

“Yes, she is amazing.” Mr. Pennington said.

“Touch her Vince, her ass is fucking incredible.” Tony said. Mr. Pennington touched my thigh and then rubbed over my crotch lightly. He moved his hand around and squeezed my butt. I closed my eyes and tried to focus on anything happy.

“Vince, slide the panties down and take a look at nirvana.” Tony said. I felt his fingers slip into my panties and pull. I felt them slide over my thighs and down to my ankles. I was now naked except for my sneakers and socks.

Mr. Pennington touched my thighs again and then he squeezed my butt again. He gasped and then his fingers slipped across my smooth pussy. I took a breath as his finger slipped between my lips. I could feel myself sliding back into slut mode. I was so happy for the last three weeks, thinking that this life was behind me but now with my assistant principal fingering my pussy while Tony watched I was thrust right back where I was before I got back to school. It made me sad, and I tried not to cry.

“So, Vince, do you want to fuck her? I think you should make sure you know what you are getting.” Tony said.

“Yes, I would like that.” Mr. Pennington said.

“Baby, bend over Vince’s desk.” Tony said and I followed directions. I could feel him behind me and then he was rubbing my butt.

“Pick your poison, Vince, she is full service.” Tony said and laughed.

I felt his cock on my butt and then he sunk it into my pussy. He slid in easily, I was wet, that is what sluts do. He buried himself into me and I heard him groan.

“Nice pussy, huh Vince?” Tony said.

“Yes, wonderful.” Mr. Pennington said and started to fuck me slowly.

“Baby, I guess you have figured out by now that Vince here will be using you to help with fundraising and general moral. You keep being a princess and making good grades, good job so far this semester by the way. However, whenever Vince reaches out you will do whatever he says, imagine he is me.” Tony said as my assistant principal fucked me on his desk.

“Do you understand baby?” Tony said.

“Yes, Tony.” I said and laid my head on the desk.

“That’s my girl.” Tony said and I heard Mr. Pennington groan as he squeezed my hips. I felt a warmth and I knew he was filling me with his cum.

He pulled out and sat down in his chair. I heard him take a deep breath. I stood up and looked at Tony.

“Get dressed, sweetie, you don’t want to be late for 5th period.” Tony said and laughed.

I pulled up my panties and shorts. I slipped my bra and halter on and straightened my hair. I looked at Tony and he was smiling.

“So pretty, you run off to class now. Vince will let you know when he needs you next. By the way, you need to go to the mall tomorrow, there is a shop called Mystique, see a woman named Ginger. She will get you set up. Have a great semester baby girl.” Tony said and I turned and walked out of the office.

I walked back to class, a little numb and leaking cum. I looked down and hoped it would not leak through my shorts. I made it back to my math class just as the bell rang. I grabbed my books and headed to my locker, hoping no one could smell sex on me.

Cheer practice was tough that afternoon, I cleaned myself as good as I could, but I am sure it felt different when my base had to lift me, his hand over my crotch. I hoped it was not too bad, he didn’t seem to notice. I showered after practice and then again in the dorm, but I could not wash off the scent of slut.

I fell asleep early and had vivid dreams of jumper cables and whips. I woke up tired and went through the motions the entire day. Practice was better than yesterday, but I was so tired I made a lot of mistakes. My new coach was not happy, and he let me know it. I showered and then caught a bus into town. I found the shop in the mall and walked in. A pretty lady with short black hair walked up to me.

“Hello, pretty girl, how may I help you?” the lady said in a French accent.

“I am Cassie, I was told to ask for Ginger, Tony sent me.” I said and the lady put her hands to her mouth.

“Oh, mon dieu, you are Cassie?” The lady said and I nodded. She took my hand and led me to the back.

We went through a curtain and there was a large dressing room with couches and two rooms facing the couches. She sat me on the couch and looked down at me.

“You are precious, you sit here while Miss Ginger gathers some special things.” She said and I watched her scamper off.

I looked around and just the furniture looked very expensive. I would never be able to shop in a place like this. I guess being Tony’s slut allowed for certain niceties. I saw Ginger walk back in with clothes over her arm. She went into one of the rooms and looked back at me.

“Come sweetheart, let’s get you dressed.” Ginger said and I stood up and walked over to her.

The dressing room was large with a big bench and a couple of chairs. There was a huge mirror on one wall. I stopped in the middle of the room and looked around. I felt Ginger touch me and then she pulled my shirt over my head. She gasped and then popped open my bra.

“Oh, my dear, you are remarkable, they are so full and yet so dainty.” She said and held my breasts in her hands. She squeezed them a little and then knelt.

She pulled off my shorts and then my panties. She untied my sneakers and removed them along with my socks. I was standing in the middle of the room totally naked. I saw another worker walk by and smile. Ginger stepped back and smiled.

“It would be impossible not to create a masterpiece with a canvas like this. I am honored to dress a beauty such as you.” Ginger said and I smiled.

I felt good for a second as she complimented me and then I realized she was dressing me up to get fucked by old guys. She turned and pulled out some black hose. She knelt and picked up my foot. I saw her look at my foot and then run her fingers through my toes.

“Even the feet are splendid, you are quite the package my little one.” She said and started to slip on the hose.

They were stockings and they had black lace at the top that hugged my thighs. She put the other one on and then held up a small piece of black material. I realized it was panties, well barely. They covered my pussy lips and that was about it. She stepped back and put her hand to her mouth again. She pulled a black dress off the hook and slipped it over my head. The top was a little low, the tops of my breasts looked good. The straps were tiny and delicate and slipped over my shoulders. She straightened out the bottom and I looked in the mirror. The skirt was decent but showed a lot of leg. I did look good, I had to admit. My blonde hair with the black dress was dramatic. I heard a click and I turned to see her taking a picture with her phone. She took another with me looking at her.

“Tony insisted on pictures.” Ginger said and I nodded.

She quickly pulled the dress off and then the panties and hose as well. She pulled out white hose and soon I had on white thigh high stockings. She pulled up some sheer white panties up my legs. They had ties on the sides, and they were basically see-through. I looked in the mirror and it pretty much looked like I was naked. She pulled a white dress off the hook and dropped it on me.

It was a white sundress with lots of lace. It really was pretty, and I liked the way it looked on me. I looked like an innocent schoolgirl, that made me chuckle. I knew this dress would be used to create lots of excited men that would then deposit their seed in one of my holes. I sighed and looked back at Ginger.

“That is precious, like a spring day.” Ginger said and I smiled. I did make me feel good when she said stuff like that.

She pulled four other dresses and I looked good in all of them. She giggled and soon I was naked again in the room. She turned around and picked up something. She turned back around, and she was holding a red plaid skirt. It was pleated and short. She slipped it up my legs and it fit perfectly. It fell across my thighs. She picked up a white shirt and put it on me. She buttoned a few of the buttons and tucked it into the skirt. She opened the top two buttons, and my cleavage was visible.

She knelt and slipped on small white socks with lace at the top. She reached over and slipped black shoes on my feet. She stepped up and then she pulled out a brush. I looked at her strange and she smiled. She brushed my hair and put it in a ponytail with a red bow. She giggled and stepped back.

I looked in the mirror and I looked like a cross between an innocent schoolgirl and a porn star. I looked back at her.

“I was told you were to wear this home.” Ginger said.

“Um, can I have some underwear?” I said and she shook her head.

“The instructions were very specific.” She said and I sighed.

I looked back in the mirror and wondered what kind of attention I would attract dressed like this. I held onto the hope that I would be able to get home safely.

“I will pack up the clothes and have them shipped to your room. Is there anything else I can do for you sweetheart?” Ginger said and I looked at her. She could tell something from my face.

“I am so sorry; you really seem like a sweet girl.” She said softly and I smiled at her.

“Thank you.” I said and walked out of the room.

I walked out of the store and started walking through the mall. I caught a lot of the men glancing over. I could feel my breasts bouncing slightly as I walked, I figured that wasn’t helping me blend in. I felt my phone vibrate and I looked down at it.

“Hello Tony.” I said.

“Hey, princess, you get all your new clothes?” Tony said.

“Yes.” I said.

“Are you dressed in your pretty schoolgirl outfit?” Tony said.

“Yes.” I said.

“Good, have a seat over at the wall surrounding the fountain.” He said and I looked over and saw the small wall. I walked over and sat down, my feet dangling.

“I am sure you are precious; I wish I was there to just fuck the daylights out of you.” Tony said. I didn’t say anything as he didn’t really ask me a question.

“Ok, baby, here is what will happen today. First, your name for today is Francesca and you are 14. Do you understand?” Tony said.

“Yes.” I said, thinking this was getting weird.

“Ok, you remember what it was like to be 14, right baby girl?” Tony said.

“Yes.” I said.

“Good, I want you to be a good little actress today. By the way, you are a virgin as well. I know you remember what that felt like.” He said and laughed.

“Tony, what is going on?” I said.

“Baby, you are going to start your fundraising activities today. You see, there is a man that has some distinct likes, and you will meet most of them. You just have to go with the flow and be the little 14-yr-old virgin and make all his dreams come true. Do you think you can do that sweetheart?” Tony said, his voice sounding a little more serious. I thought of Carl and his strap, and I took a deep breath.

“Yes, Tony.” I said.

“Good girl, now I need you to go and buy an ice cream cone and then sit at one of the tables in the food court. The rest of it will take care of itself. The man will have on a suit with a red flower, don’t go off and fuck anyone else before he gets there.” Tony said and laughed. He hung up and I lowered my phone to my lap.

I sat on the wall for a couple more minutes, thinking about what my life had become. I thought of my mom and how she had been putting up with this for 20 years. I could keep it up for a little while longer, but I realneeded to think of something soon, this was getting weirder and weirder. I got off the wall and went to buy an ice cream cone.

I sat at a table at the edge of the food court, trying not to look at any of the men or boys that were staring at me. I licked my ice cream slowly and I could tell they liked that. I must look like a walking wet dream, an innocent schoolgirl licking an ice cream cone. It didn’t take long, and I heard a soft voice.

“Little girl, are you ok?” I heard a voice and I looked up. There was an older man in a black suit with a red flower in the pocket. He had gray hair and small wire glasses. He did look like he was nice, and he was smiling. I remembered what Tony said and I took a deep breath. I looked up at the man and shook my head side to side, trying to put on a sad face.

“Oh my, honey, what is wrong?” He said and sat down. I tried to think of what he would want to hear.

“My daddy said to call him when I was ready to be picked up, but my phone doesn’t have any service and I don’t know what to do.” I said in my best little girl voice.

“Sweetie don’t be sad. I will help you, what’s your name?” He said.

“Francesca.” I said softly and he gasped.

“What a beautiful name, that is my granddaughter’s name.” He said and I figured out one of his fantasies right away.

“That is cool.” I said and licked my ice cream again. I saw his eyes light up when he saw my tongue slowly move across the cone.

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