Poor Little Cassie - Cover

Poor Little Cassie

Copyright© 2021 by Demonhead

Chapter 27: Sunday – Cassie Takes a Boat Ride

Fiction Sex Story: Chapter 27: Sunday – Cassie Takes a Boat Ride - 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   ft/ft   Fa/ft   Mult   Coercion   Drunk/Drugged   NonConsensual   Rape   Reluctant   Slavery   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   Prostitution  

I woke up with someone shaking my shoulder. I looked up and saw Tony. He looked angry.

“Get the fuck up, we are going to be late.” He said and I looked at the clock. It was 8:30, I had slept for over 10 hours. He grabbed my arm and pulled me up.

“Ouch, I am getting up.” I said.

“Don’t start with me baby girl. We are leaving in 10 minutes; I pulled your clothes.” He said and walked out of the room.

I sat up and looked at the clothes on my bed, there was a bikini, some jean shorts and a button shirt. Not bad for a dude. I got up and went into the bathroom, my bladder woke up quickly. I brushed my teeth and my hair, no time for a shower, hope they liked the smell of fucked teenager. I walked back in the room and put on the stuff he picked out. I touched up my hair and went downstairs. It hit me as I walked downstairs that Tony had gotten into our house.

“How did you get in the house?” I said as I got downstairs.

“Baby, with two of my prime sluts in the house don’t you think I would have a key?” He said.

“I wish you wouldn’t be so cruel; you don’t have to; I do what you want anyway.” I said and grabbed a glass of water.

“That’s true, so you are not a slut, how about cunt, is that better?” He said and laughed.

“Are we going?” I said and he stood up.

We got in his car, and he started driving. He got on the freeway, and I looked over at him.

“Where are we going?” I said.

“We have to meet them at the marina, we are supposed to be there at 9:30 but that ain’t happening.” He said.

“We are really going on a yacht?” I said.

“Yep, I hope you don’t get seasick, baby.” He said and I didn’t think about that. I had never been on a boat before.

“These guys are into ropes and shit so you will most likely spend a lot of time tied up, so I guess if you get sick you can throw up on yourself.” He said.

“You say such nice things.” I said and looked out of the window. He laughed.

We pulled up to the marina and he parked next to the pier. There were a lot of boats tied up and we started walking down the boardwalk. I saw a dude messing with some rope and Tony walked up to him and they shook hands. The guy was tall, a little taller than Tony and way taller than me. He had long hair in a ponytail, and he was wearing a muscle shirt with lots of muscles under it. He looked down at me as he was shaking Tony’s hand.

“Hey Tony, nice seeing you. Is this the little slut you talked about? She is tiny.” He said.

“She doesn’t like being called a slut.” Tony said and the man looked at me.

“She is going to fuck us all, right?” He said.

“Yeah, but you have to talk nice to her as you shove your dick in her.” Tony said and the man laughed.

“Ok, no problem. Welcome aboard, your highness.” He said and motioned to a ramp.

Tony laughed and I followed them up the ramp. This was not starting very well. The boat was huge, there was a massive deck on the front and multiple levels. There was another man, he was wearing a pair of white shorts and an unbuttoned Hawaiian shirt. He had a dark tan, and he was not bad looking, well at least I will get fucked by pretty people. I decided I would make the best of it, there were only three of them and that is much better than what I have had to put up with recently. They seemed relatively nice, but I have learned the hard way that nice can turn into a punch in the stomach pretty quick. However, it was a nice boat, and the weather was beautiful, it was a great day for a small gangbang.

Tony and I sat on the deck as they scrambled around the boat. Soon we were moving away from the pier, and I got a little fright. I would be out on the open water with these three guys with no way to escape, I hoped I didn’t end up in the water. Fred would be mad if I died, and he didn’t get to film it. I was not really worried about them killing me though as much as I was afraid of them beating the shit out of me. They were all big, that would not be pretty, and my body was still a little sore after my week from hell.

“Hey Tony, so tell us about our little snack here that is not a slut.” The man with the ponytail said and threw Tony a beer. Tony laughed and opened the beer, it foamed, and he sucked the foam off the top and took a big drink.

“Wait, she’s not a slut? She is going to fuck us all, right?” The other man said as he walked up.

“Jesus Christ, I just don’t like the word okay, don’t fucking worry you will all be fucking me.” I said and they all looked at me stunned for a second and then laughed.

“I like her. So, we can fuck you all we want as long as we don’t call you a slut, got it. How old are you?” The man in the Hawaiian shirt said and sat down.

“16.” I said and he spit out his beer.

“Fuck Tony, you running out of sluts, oh sorry, you running out of girls that will fuck everyone? You are trolling the high schools now?” He said.

“Sunshine here fell into my stable a couple of months ago when I busted her cherry on her daddy’s bed. She is quite the handful as you will see. I have been banging her mom for 20 years and the apple didn’t fall too far from the tree.” Tony said and I felt my anger rise as he talked about my mom.

“20 years, really, is she your kid?” The long-haired man said.

“Don’t know, maybe.” Tony said and laughed.

“Man, that is fucked up. But you know what? I don’t care as long as she can suck dick.” Hawaiian shirt man said.

“That she can do. Sweetie, show my friend Bob here how good you are at sucking cock.” Tony said and I took a deep breath, that didn’t take long.

I stood up and walked over to the Hawaiian shirt man who I guess was Bob. He stopped me and reached up and unsnapped my shorts. He unzipped them and leaned back.

“Now take those off nice and slow. I love seeing that.” He said.

I grabbed the sides and slowly pulled them down to my thighs. I stopped and ran my hand across my now exposed thigh, and he moaned. I pushed them down a little farther and let them fall to my ankles. He was staring at my red bikini bottoms. I kicked my shorts away.

“Fuck, Tony, she is a hot little thing. She will be perfect.” He said.

“I told you. Sweetie, take off that shirt for Bob, he hasn’t seen your best features yet.” Tony said.

I unbuttoned my shirt slowly and my red bikini top slowly appeared along with a lot of cleavage. I pulled the shirt off and let it fall. The man was looking at me like I was a steak. He licked his lips.

“That is a rocking little body, you are really 16?” He said.

“Yes, and never been kissed.” I said and Tony laughed.

“Yes, Bob, she is a virgin, all for you.” Tony said.

“Wait, what? You are fucking with me, right?” The man said and looked at Tony.

“Baby, will you scream and yell when Bob fucks you, so he thinks he is fucking a virgin?” Tony said and I nodded. Tony laughed.

“Fuck you, I knew you were full of shit, with a body like that no way no one has ever banged this little bitch.” Bob said.

“Yeah, she knows her way around a cock pretty well. Baby, get on your knees and suck Bob, make sure and show him your trick.” Tony said and I knelt.

Bob’s cock, as it turns out was kind of big. He opened his shorts and I fished it out. My hand looked really small holding it, I got a little worried for a second and then I remembered Marcus. I smiled and figured this one was no problem after tackling that black monster. I leaned forward and kissed the head. I looked up and he was watching me, why do guys love seeing us with their cock in our mouth? I kept my eyes on him and slowly licked down his shaft. I moved down to his balls and sucked them gently. He groaned and leaned back with his arm over his eyes.

“Fuck, that is nice.” Bob said and Tony laughed.

I sucked one of his balls into my mouth and rolled it around. I let it slip out and then licked his sack. I moved back up the shaft slowly and then rolled my tongue over his head. I felt his cock lurch in my hand, and I put my other hand on it and moved them up and down. I sucked the head in and started moving my head down. I felt him touch the back of my mouth and I took a deep breath. My mouth was a little stretched around this monster so I hoped I wasn’t biting off more than I could chew, or swallow. I got up on my knees and pushed my head down hard.

He let out a huge groan as his cock slipped into my throat. I pushed down and felt his hair on my lips. I felt his hands on my head, but he was not pushing, that was different. I held him in my throat for a few seconds and then pulled off very slow. As soon as he came out of my throat, I felt a blast hit the back of my mouth. I swallowed just in time before the second blast filled my mouth. I swallowed that one and pulled him out, taking the last load on my tongue. I looked up at him and put his cock back in my mouth, swallowing his cum with his cock in my mouth. I pulled it out slowly and licked the head.

“Mother fucker, I think that is the best blowjob I have ever had.” Bob said and I smiled.

“Hey, not a slut, come over here. After watching that I need that little mouth on my cock like now.” The other man said.

I got up and walked over to him. I knelt and grabbed his cock, it was not nearly as large as the one I just swallowed but it was nice, nothing to be ashamed of. I sucked him deep and massaged his balls with my hand. I pulled off and he was looking at me.

“Suck my balls.” He said and I looked at him with a smirk.

“You have to ask nicely.” I said.

“Your highness, would you suck my balls please?” He said.

“Certainly, my lord.” I said and ran my tongue down his shaft and took one of his balls in my mouth.

He groaned as I rolled it around and sucked on it. I let it slip out and then I sucked on his sack. I ran my tongue all over it and then kissed it. I moved up his shaft, holding his balls in my hand. I kissed the head and then ran his cock into my throat easily. I pushed down, smashing my lips against his crotch. I rolled his balls in my hand as I held him in my throat. I swallowed a couple of times and I heard him groan. I felt him lurch and then a blast of cum fired into my throat, I held him there and he put another load on a direct path to my belly. I started to pull out and his third load slid down my throat. I pulled off him and licked all around the head.

“Fuck, you are a queen. That was remarkable. Tony, I hope you are charging for that.” He said as I sat back and looked at him.

Tony laughed and I looked over and he was holding his cock. I scooted over and started working on him.

“Tony, so this is how this will work. We should be meeting Cooper in about an hour. You will need to be fucking not a slut as we approach them. That is sort of a requirement.” He said and I was wondering what the fuck he was talking about as I licked Tony’s balls.

“Ok, I think I can handle that.” Tony said and the men laughed.

“Yeah, I figured you would be ok with that. So, Cooper is a little different. The quality of the stuff we get to buy is directly related to the quality of the offering we have.” The man said.

“Offering?” Tony said as I took him in my throat.

“Yes, pussy. Cooper only takes pussy as the offering, the better the pussy, the better the product. I am hopeful we will see the good stuff with this little one.” The man said and Tony filled my mouth with cum. I worked to swallow it but some of it ran off on my chin. I sat back and wiped my chin with my finger.

“That is different.” Tony said.

“Yeah, but they have the best stuff in the area. We have a few girls that we usually use but we were hoping you would bump the quality and I think you came through for us. Let’s just hope Cooper likes her, it could be a good day.” The man said and my cock count just grew by one, I guess.

I sat and looked at them and wondered what this was turning out to be, what stuff are they talking about, I had a feeling it wasn’t anything legal since we were meeting someone on open water that took pussy as an offering. Nope, nothing normal about that.

“So, let’s get some fresh beers and I have to take a leak, then we will get her set up.” Long hair man said and stood up.

I watched them both walk off and I looked at Tony.

“What is going on?” I said.

“I actually don’t know baby; I am surprised as much as you.” He said and I did see confusion in his eyes, I had never seen that before.

“Aren’t they your friends?” I said.

“Yeah, but all they said was bring a girl and meet them at 9:30. I didn’t know about any of this other stuff.” He said.

“It is a little scary. I am not sure I want to meet a man who takes pussy as an offering.” I said.

“Yeah, that is strange. These are good guys though; I think we should be alright.” He said and that did not make me feel any better, I didn’t really trust Tony’s judgement of character. These guys wanted a slut to offer to this Cooper person and they are the good guys?

The long hair guy walked up and held out his hand. I took it and he helped me up. He took my hand and wrapped a leather buckle around it. It was brown and had two silver rings hanging from it. He pulled it tight around my wrist and then put one on my other wrist. He took my hand and I followed him to the front of the boat. There was a big table set up and some chairs. He walked me over and then I saw a structure of some sort. He grabbed a chain that was hanging and attached it to a ring on my right wrist. He grabbed another chain and attached it to my left wrist. I looked up and there was a bar running across the top of the structure that the chains were attached to. He pulled on a lever of some sort and the chains started moving up, pulling my wrists. My arms went up and soon they were straight above my head. He pushed down on the lever and the chains stopped moving but I was now stuck with my arms in the air. My feet were still on the ground, so it was not painful, but it was scary not being able to move.

“What is going on?” I said and long hair man walked up to me.

“Cooper likes the bitches secured so they don’t run away.” He said and that did not make me feel good at all.

“Bob, what is happening?” Tony said.

“When we get close to the boat you will need to be fucking her. Cooper wants to see someone fucking the girl or they will not even start the negotiations.” Bob said.

“What negotiations? What are we doing, Bob?” Tony said and the man laughed.

“We are buying cocaine Tony, I thought we told you that. Not a slut here is our ticket in the door.” Bob said and I saw confusion again in Tony’s eyes.

Tony did not look strong or scary like this, he just looked lost. I guess I was at the mercy of Bob, long hair man, and the mysterious Cooper. Yeah, this wasn’t scary at all. I tried to slow my breathing to slow my heart rate. Long hair man walked over and looked at me. He smiled and untied my top. He pulled it off and tossed it aside.

“Wow, Cooper will love these. You are a gold mine, little one.” He said and rubbed on my breasts.

“He knelt and I felt my bottoms get loose and disappear. I felt his warm breath on my pussy, and I moaned. He stood up and looked at me.

“That is a beautiful pussy. You ready to get fucked, not a slut?” He said and smiled.

I did not think he wanted an answer since he grabbed my leg, lifted it and ran his cock into me. I groaned as I was not prepared to start the gangbang yet, I was still working on what the fuck was going to happen. He pushed it all the way in, and he kissed me on the lips.

“Nice and tight, at least for now.” He said and grabbed my boob.

He fucked me slow as he rubbed on my boob and kissed me occasionally. I felt a little helpless as my arms were secured over my head. It was a weird feeling, of all the sick things that Tony and coach had done to me this was the first time anyone tied my up or whatever this was called. I felt his hand on my ass as he pulled me into his cock. He was holding my boob and my ass as he fucked me, he had everything covered.

“Tony, this is some nice snatch, I will not mind fucking this little one a few more times.” The man said as he moved in and out of me.

Tony did not respond; he did not look comfortable. I guess he did not like it when he was not calling the shots. The man was lasting a long time, I guess my blowjob took the edge off. He was still moving slow, I appreciated that, I had been fucked hard and fast a lot lately, this was a nice change. He finally finished and came in my pussy. He pulled out and kissed me as he dropped my leg.

“You have a fine pussy, sweetie. I look forward to the next time.” He said. He squeezed my boob and walked away. I saw Bob walking up and undoing his pants.

“Ready for another one, sweet stuff? But from the looks of you I think you can take on quite a few more pretty easily, am I right?” He said and pushed his monster cock in me.

I groaned and I was glad long hair went first, it loosened me up and lubricated the path. This big cock would have hurt a little if I had to take it dry. He slid it deep, and I felt it touch places that rarely got action. He grabbed my boob and leaned over and kissed a nipple. That felt nice, as did the big slab of meat buried in my pussy. He was moving slow; this was turning out to be the gentlest gangbang I ever had. I just hoped this Cooper dude didn’t throw a kink into things. He was a drug dealer though so I was not feeling really confident that I would get this type of treatment.

“Fuck, this is good pussy.” Bob said and emptied his balls in me. He pulled out and touched my cheek.

“You are special, little one, and I am glad you are here.” Bob said and walked away.

“Nice, isn’t it, Bob. I am thinking we may get the top-level stuff today.” Long hair said.

“Yeah, I am not counting my chickens. Cooper is so unpredictable.” Bob said and sat down at the table.

They were all sitting at the table, drinking beer as I hung from this strange contraption with cum running down my legs. It felt a little weird and the fact that none of them were even looking at me was even stranger.

“Ok, we should be in range in about 10 minutes, can you go tell Frisco they are going to board starboard.” Bob said and long hair got up and left.

Who was Frisco? I wondered if I needed to raise my cock count?

“Tony, we will pull up alongside the other boat, when we are in sight range you need to be fucking her. Go slow, you need to last until they board.” Bob said and Tony looked agitated. I guess he didn’t like being told what to do. I sort of liked that.

I saw the other boat and it was getting closer. It was as least as big as this one and I could make out a lot of people running around doing stuff. I assumed it had something to do with operating the boat, they were pulling ropes and moving things, it looked very busy over there. I guess one Frisco adds up to all those dudes.

“Ok, Tony, you can start.” Bob said and Tony got up. I worried for a second if he would be hard, this was a lot of pressure. He pulled out his cock and my worries disappeared. He picked up my legs and sank his cock into me and held it still. His head was near mine, but he was watching the other boat.

“Tony, what is happening?” I whispered. He did not turn his head.

“I don’t know baby.” He whispered.

“I am a little scared. If something happens, I can’t move.” I whispered again.

“Yeah, I know. I don’t know what is going to happen.” He said and I saw the boat getting closer.

“Tony, start moving now.” Bob said and Tony started fucking me slow.

I have to admit this was the fucking weirdest thing ever. I sure hoped they didn’t have guns, the small naked girl hanging there would be an easy target. That would suck. I realized as I was hanging there getting fucked by Tony as a drug dealer prepared to board us that I was a little obsessed with death lately. I guess the whole snuff film stuff fucked me up worse than I thought. I hadn’t had that nightmare the last couple of nights, but I think that had to do with me being either beat up or coming down from whatever pill coach gave me.

The other boat got close enough for them to throw a rope over. Long hair caught it and tied it to something. Tony continued to fuck me as they tied the boats together. It looked weird being out here on the water and the only two things in sight were now tied together. I saw a black man step out onto the deck of the other boat. He was big and dressed way differently than all the other guys around him. He was wearing sunglasses and dark clothing. He looked ominous, I guess that was the drug dealer look.

“Tony, finish if you can.” Bob said and continued to look at the other boat.

Tony sped up and he was fucking me hard now. My gentle gangbang was over, my feet were flying around, I noticed I still had on my sandals. That struck me funny for some reason as I was getting fucked while we waited for a drug dealer to come over and meet us. Tony groaned and I felt him fill me with his cum. He dropped my legs and sat down at the table.

The man walked slowly across the board they had put between the boats. He looked even bigger as he got closer. My three men just watched him as he got closer. Nobody else was moving on the other boat, they were all just watching him. He walked over to me and looked down at me. He put his hand on my chin and lifted it. He turned my head from side to side slowly. Was he checking my ears? He moved his hand down and grabbed my boob, squeezing it and then pinching the nipple. I flinched and he looked at me. This was so fucking strange.

He walked around behind me, and I felt him grab my ass and squeeze, I felt like he was inspecting the merchandise. My three guys just sat and watched, they looked like they were nervous. I hoped I was passing; I did not want to see what happened if they did not like me. He walked around the front and knelt. He pulled my legs apart and he was looking at my pussy. He stood up and started to open his pants, here comes the final inspection. He pulled out a long black cock and lifted my leg. He slid it in, and it felt like it was in my stomach as it entered.

He lifted my other leg and then pushed in a little deeper. I grunted and he smiled. His teeth were gold and some of them had little diamonds in them. He pulled back and then pushed back in hard. I felt myself grunt as he hit bottom. He continued to pull out and then drill into me, it was not painful, but I was terrified. He started speeding up and then he was hammering me. I closed my eyes and put my head back as the huge black man dominated my little body. I heard him grunt and then pull me into his crotch. I opened my eyes and watched his face as he filled me with his cum. He pulled out and walked over a few feet to the left of me and stood there.

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