Poor Little Cassie - Cover

Poor Little Cassie

Copyright© 2021 by Demonhead

Chapter 13

Fiction Sex Story: Chapter 13 - 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  

Friday started like any other day until I was walking to lunch with my friends. We walked past the office and Mr. Pennington was standing in the hallway.

“Miss Jones, can I speak with you?” Mr. Pennington said, and my friends looked at me strange.

“Girls, I will meet you in the cafeteria, cheer stuff.” I said and they nodded and headed down the hallway.

I walked up to Mr. Pennington. He looked down the front of my shirt, it was a yellow sleeveless that buttoned up the front, the two open buttons gave him a great view of my bra from directly above me. I saw him lick his lips and I got a shiver of disgust.

“Miss Jones, can I see you in my office?” He said, I nodded and followed him.

The office workers smiled at me as we walked past. I am pretty sure they had no idea what was about to happen. I was pretty sure that his cum was going to end up either on me or in me. I smiled back and followed him into his office. He closed the door and looked at me.

“You are so fucking gorgeous. Please take off that shirt and bra, I need to see those tits.” He said and I sighed.

I unbuttoned the shirt and then popped open my bra. I laid them both on the chair. He was staring at me. I was still wearing my jean shorts and my sneakers.

“You know, it is too bad you can’t cheer like that, you girls would get a lot more fan involvement.” He said and laughed. I smirked at him, and he walked past me to his desk. I just stood in the middle of his office, topless. He sat down and looked at me.

“Well, come over here. It will be easier to talk if you are a little closer.” He said and I felt my boobs jiggle as I walked up to the desk.

“God, they are beautiful, we have got to think of a way to start topless cheerleading.” He said as I walked over.

I stopped next to him, and he touched one of my nipples, they were stiff, I guess a slut’s nipples are always stiff when they are out in the open. He pinched it gently and he moaned.

“Ok, I must focus, let’s talk about your schedule moving forward. By the way, I am not sure what you did with Gregory yesterday but holy shit, he opened his checkbook big time. We may just get some new uniforms for you girls as a little reward for your efforts.” He said and turned his computer screen so I could see it.

“So, first you will be visiting Gregory at least twice a month, we don’t want that well to dry up. We will make that happen on every other Thursday. I will give you instructions the day before, his fantasies are somewhat unpredictable.” He said and smiled. He typed something and I realized he was filling out a spreadsheet.

Great, a spreadsheet to keep track of who gets to fuck Cassie, just what I always wanted. I thought school would be my safe place but now I was realizing Tony’s reach went everywhere. I felt a surge of hopelessness and then I remembered my mom had been doing this for 20 years, how did she do it?

“Speaking of instructions, I have changed your schedule. You will now be assigned to the office for third period. I moved your English to 5th period, and you will have to drop accounting. You can take that next semester, sorry about that but we must be flexible.” He said and I looked over at the screen. He slapped my boob and I realized I was daydreaming.

“Miss Jones, please pay attention.” He said.

“Now Miss Jones, did you follow that you are now assigned to this office 3rd period, and you will have to drop accounting?” He said and I groaned.

“Mr. Pennington, accounting is my favorite class.” I said and he grabbed my breast.

“I understand but we will make sure you get it next semester if all of this works out.” He said as he massaged my breast.

“What do I have to do during third period in the office?” I said.

“Well, a lot of what you are doing now, I just love your tits so you will rarely have a shirt on when you are in here. You will also be expected to deliver messages for me to classrooms and you will be sucking my cock quite a bit.” He said and I tried to keep a happy face. I didn’t want him to report to Tony that I was being difficult. Carl’s garage was an amazing motivator.

“Now, we will be scheduling more fundraising activities for you. They will be at least weekly, sometimes more, it sort of depends on our sponsors schedules.” He said.

I wasn’t sure if he wanted me to agree with everything or applaud him on his organizational skills, so I just stood there with my boob in his hand.

“You will start your new schedule on Monday. You can pick up your new schedule from Mrs. Sparks on your way out. Before you leave though, I need you to get on your knees and use that pretty mouth.” He said and I knelt.

He opened his belt and unzipped his pants. He pushed them down and his cock popped out. It was hard already; I was not surprised; most everybody likes topless sophomore cheerleaders. I wrapped my hand around it and sucked the head in. I ran my tongue around his head, and he moaned. He was easy to please. I slid him deep into my mouth, he was not large so I could almost get him all the way in without using my throat. I stroked him slowly as I pulled off him, I used my other hand to squeeze his balls. His sack was big and loose, it felt like a bag with two big marbles in it. He was groaning constantly.

“God, you are so good at this.” He said and I looked up. He was looking at me with his cock in my mouth and my boobs moving.

I could feel him getting close, so I took all of him into my mouth opening my throat for the last two inches. I kind of wanted him to cum in my throat so I wouldn’t have to taste it. He grabbed my hair and pulled me off his cock. I was stunned and then he grabbed his cock and started stroking it.

“Squeeze your tits together, I want to cum on them.” He said as he pumped his cock.

I pushed my boobs together and he exploded all over them. He shot out at least three ropes on my boobs and then he stood up and dripped more cum on them. My boobs were covered and there was some on my hands. I felt gross and he sat back in his chair.

“God, that was good. Stay right there.” He said and grabbed his phone. He snapped pictures of me holding my cum-covered boobs.

“Ok, you should get to lunch. I will see you on Monday.” He said and I reached for the Kleenex on his desk. He grabbed my arm.

“No, don’t clean them off, just put your bra on over it. Wipe your hands on your stomach.” He said and I almost groaned.

I stood up and picked up my bra. I put it on, and it covered most of the cum. It felt sticky and gross. I looked down and there was a glob on my cleavage, over the bra. I looked at him.

“Ok, that one you can pick up with your finger and put it in your mouth. Slowly.” He said.

I picked up the glob of cum and sucked it off my finger. He seemed pleased but I had swallowed so much cum recently that this was not that hard. I wiped my hands off on my stomach and now it was shining and sticky like my boobs. I put my shirt back on and buttoned it a little more than I had before. I didn’t want anyone to see anything wet on my chest. I turned and started walking towards the door.

“See you on Monday, Cassie.” He said and I opened the door and left without looking at him.

I picked up my new schedule and headed to the cafeteria. My boobs felt weird in my bra, and I could still smell his cum on my hands. This semester was starting to suck.

I went through the rest of the day in a daze. I was a little angry, this was supposed to be my safe place, away from Tony. Now it was a nightmare with a pervy assistant principal and a list of old guys that wanted to fuck me. The bell rang in last period, and I picked up my books. I started walking to cheer practice, the only bright spot left in my day.

I dressed slowly in my practice uniform. Yes, we had practice uniforms, we were nationally ranked, so we had many extras as they say. Our practice uniforms were just older ones from a few years back. These were pretty cool; the tops were tight and showed off a lot of stomach. We were all fit, so this was a good thing. The bottoms were the basic skirt, with cheer panties underneath. We always wore our regular panties as well, it helped to keep stray fingers from accidentally going somewhere they shouldn’t during the lifts.

We were in the gym today, it was raining. We gathered and waited for the coaches. I started a conversation with the new flyer, her name was Jennifer, and she was a freshman but she looked even younger. She had brown hair to her shoulders, and she was smaller than me with almost no boobs, but her legs were strong, and she was a great flyer. She was from a few states over and they moved here so she could be on this team. She knew the new coach; they were from the same town, and she had taken lessons from him for a few years. She seemed nice and I figured you never had enough friends.

Practice went well and I was really tired, they work us hard every day, especially our new coach. Jennifer was sitting on the floor, and I was wiping my face with a towel when I saw Mr. Pennington talking to our new coach. They were looking at us and pointing. I had a bad feeling and then my coach motioned me over. I walked over slowly, trying to think of something normal this could be.

“Cassie, I need you to go with Mr. Pennington.” He said.

“Ok, I need to take a shower.” I said.

“Go now and get it done quick.” Coach said and I headed to the locker room.

I showered quickly but I had to wash my hair, it was very sweaty. I stepped out of the shower as the other girls were coming in. I walked to my locker and Jennifer was sitting on the bench near my locker. She looked worried. I opened my locker and dropped my towel.

“I am worried about you.” She said and I smiled, sliding my panties up my legs.

“Why, sweetie?” She said as I started putting on my bra.

“Why did Mr. Pennington come into our practice and what does he want?” She said as I closed the front clasp of my bra and adjusted my breasts. I grabbed my jean shorts.

“I will be fine. Don’t worry about me. It is about some fundraising stuff.” I said and wondered why she was suddenly concerned about me. She smiled and was looking at me differently.

“You are very pretty.” She said. I sat down and put on my shirt. I pulled my socks and sneakers out of my locker.

“Not as pretty as you.” I said.

“No, I am not pretty.” She said and I looked at her, stunned.

“Honey, you are precious. Your face is flawless, your brown eyes are spectacular. I love your hair and your legs are amazing. You are very pretty.” I said, tying my shoe.

“I don’t have any boobs.” She said and I looked at her chest. I had seen her in the shower, and she was very small. Her boobs were just bumps with nipples but for some reason that did not take away from her beauty, at least in my eyes.

“How old are you honey?” I said.

“I turned 14 just before Thanksgiving.” She said and I nodded.

“Then your boobs are perfect, mine looked just about like that when I was 14 two years ago and look at them now.” I said and pushed out my chest. She giggled and she got even cuter.

“Do you really think they will grow that much in two years?” She said.

“Most likely, but even if they don’t, you don’t need them. You are beautiful even with them how they are now.” I said and took her hand. It was small and delicate, like the rest of her.

“Thank you for saying that. I wish I could believe that as well.” She said.

“Well, I will keep telling you until you believe it yourself.” I said and she smiled. Her lips and teeth were perfect, and her smile lit up her face. I stood up and kissed her on the top of the head, the smell of sweat was strong, she worked really hard today as well.

“Thank you for talking to me. I have never had any friends on my other teams.” She said.

“Anytime sweetie, us flyers have to stick together.” I said.

I turned and walked out of the dressing room. Mr. Pennington was standing in the hall, waiting for me.

“Thank you for making that quick.” Mr. Pennington said. I looked at him and he was smiling. I had a feeling this was not going to be anything good.

He walked out of the gym, and I followed. The halls were empty and quiet, it seemed strange. I was thinking about what Jennifer said. What could make such a pretty girl have such low self-esteem? Shit, I was being forced to be a slut for Tony and I still feel like I felt better about myself than her. It made me a little sad. We were walking towards the library. We stopped outside and I saw a few people sitting inside.

“Cassie, slight change of plans, I need your help with one of our morale events.” He said.

“What does that mean?” I said.

“Normally, another girl does this, but we thought we would give you a chance since you are new to us.” He said and I looked at the people in the library, I recognized a couple of my teachers.

“What exactly is this?” I said and motioned to the group of teachers.

“This is a group of our elite teachers and staff. They have been recognized for exemplary performance and we are hosting a little celebration. You will help with that.” He said and I sighed.

“What do you want me to do?” I said softly.

“Oh, just what you are good at, make people happy. You can do that, right?” He said and I nodded, unsure of exactly what he thought would make some of my teachers happy.

I followed him into the library and there were 10 people in there. Four of them were my teachers, two of them now and two of them from last year. The custodian was there and a couple of crossing guards. Most of them were guys but I noticed one of the teachers I didn’t know and one of the crossing guards were ladies. I still had no idea what was going to happen, but I had a sinking feeling it was not going to be anything close to normal.

We walked to the front of the room, and everyone looked at us. They were holding drinks and I saw food on some of the tables. Mr. Pennington started talking but most of the people were looking at me.

“Ladies and gentlemen, I want to thank you for your service, and I hope you are enjoying the food and drinks.” He said and there was clapping.

“We think it is very important to keep our employees happy, especially the excellent ones so we have come up with this new monthly recognition program. Congratulations to all of you.” He said and lifted a cup. Everyone lifted their cups and there was cheering and more clapping.

“Now, I want to introduce Cassie, she will be helping us today. She is new to the recognition program but one of the top performers on our cheer team. Please make her feel welcome.” He said and they all clapped, and I heard a lot of welcomes and greetings. As they were talking, I saw my new coach walk into the library.

“Good, coach Mike is here. He will take over as the program is his baby.” He said and my coach walked up next to us. I heard a lot of greetings and he waved.

“Welcome everyone and congratulations on earning your way into this room. It is very important that we recognize our top performers and make sure they feel valued. We have a new player with us today; I know everyone loved the girl from last meeting, but I have confidence you will be pleased with Cassie. She is an exemplary cheerleader, and she is cute as a button.” He said and put his hand on the side of my head, rubbing it gently.

I heard people clapping. I was a little confused, what was going on here? I felt a little pride as he talked about me. I looked out and saw people starting to sit down. My coach was still rubbing my head and playing with my hair.

“Ok, let me show you two of the reasons Cassie is a star on our team and how she will lead us to a championship this year.” He said and I looked up at him. He was smiling.

“Cassie, please take off your shirt and bra.” He said calmly as he held my head.

The reality hit me hard, and I looked out at the group of people that were about to see my breasts. There were a lot of smiles, and some did not look nice. This was very different, all the other times I was in these situations either nobody knew me or didn’t know who I was. My family didn’t know they fucked me; they just fucked a cute girl named Rose. Carl and his gang just looked at me as a little blonde girl for them to abuse, they didn’t really know me.

These people knew Cassie, I was a student in some of their classes. The crossing guards I said hello to every day and the custodian was very sweet to me every time I saw him. The other three people I didn’t know but they knew I was a student and I had three more years to walk these halls. This was so different, and I was suddenly scared. My hands were shaking as I loosened the buttons on my shirt. I slipped it off and I heard some oohing and some murmuring. I put my shirt on the table next to us and then popped open my bra. I took a deep breath and slipped it off and put it on top of my shirt. I looked back out and the smiles were still there.

“Aren’t they impressive? So full and firm, you have to love young titties, right?” My coach said and held one of my breasts up. There were a lot of whispering and chattering.

“Now Cassie, let’s show them some more of your skills. Please step forward and pull a needle.” He said and l looked up at him, he smiled and motioned.

I stepped forward and pulled my right leg high in the air, holding it in a full split position. I heard oohs and aahs from the crowd. This was an easy position for me, although it felt weird doing it topless in the library in front of my teachers. I felt my coach move and then I felt this hand on my inner thigh, I flinched but held my position.

“Very nice, wouldn’t you say? Notice how flexible she is, and how she holds her concentration. This is important in competition; we have to be strong and sturdy in our stunts and Cassie is one of the best.” He said and then I felt his hand move down my thigh over my shorts and then to my other thigh.

“But, ladies and gentlemen, how hot would this position be without these pesky shorts?” He said and I gasped. I heard a lot of agreement.

“Ok, Cassie, you can let go.” He said and I lowered my leg and stood next to him.

“Now, let’s see, how about Mr. Johnson. Cassie, would you walk in front of Mr. Johnson?” He said and I walked to stand in front of our black custodian. He was staring at my boobs. He had always been very nice to me but now I saw lust in his eyes as he looked at me.

“Willie, can you take those little shorts off of Miss Cassie?” my coach said.

“It would be my pleasure, sir.” He said and reached to open the button on my shorts. He opened it and then pulled the zipper down slowly, exposing my pink panties.

He slid them slowly down my legs, his fingers gently stroking my legs as he moved my shorts down. I stepped out of them, and he held them up. There was more clapping. I was standing in front of my teachers in my pink cotton panties.

“Nice, you can keep those as a souvenir, Willie.” My coach said and I looked back at him.

“Thank you, sir.” Willie said and held them up to his nose.

“Now we may as well finish what we started so we will need another volunteer. Cassie, would you move over to Mr. Jerkin?” He said and I walked over to my current science teacher. He was smiling at me with a strange look on his face.

“James, please help Cassie out of her cute panties.” My coach said and my science teacher reached out to the waistband of my panties.

“I have been wanting to do this all year.” He said as he pulled my panties down very slowly, his eyes focused on my smooth pussy. I thought about what he said, my science teacher was thinking about me in that way? He dropped my panties over my ankles, and I stepped out of them. He picked them up and he held them up in the air. More clapping.

“Ok, Cassie, please move back to the front.” My coach said and I moved to stand next to him. I could see the anticipation around the room.

“Folks, you have seen the needle but now you will get to see it in its full glory. Cassie.” He said and I took a deep breath.

I looked around and then I pulled my leg up straight into the air like I had done thousands of times. This time, however, my young pussy opened wide to a group of my teachers. I heard a lot of gasping and comments.

“Impressive, yes?” my coach said and I heard a lot of agreement. I felt so weird with my crotch spread wide open in the library.

“Now, when you see this position at a game in the future you will be able to think of this image. You are welcome.” He said and I felt his hand on my thigh again. I stayed as still as possible as he ran his hand down my thigh, over my pussy and onto my other thigh.

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