Poor Little Cassie
Copyright© 2021 by Demonhead
Chapter 40: Friday – Ass day
Fiction Sex Story: Chapter 40: Friday – Ass day - 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 food guys came into the room a little while later. They put down the trays and just walked to the bed and looked down at us. They dropped their pants and held their cocks, waiting for us. I guess we were past the need for words. I laid back and spread my legs. The black guy pulled me to the edge of the bed and sank his cock into me. Jennifer did the same and we were both getting fucked for food.
The guys finished and then just pulled up their pants and left. I realized as they left that they did not speak at all. Were we now just falling into a routine? Were we expected to just have our asses in the air tomorrow for “ass day”? I sighed and stood up, cum ran down my leg. I walked over and got some toilet paper; I didn’t want to mess up our clean sheets. I handed some to Jennifer. I wiped my leg and shoved the paper in my pussy. I picked up the metal cover and it was meat loaf. I had not eaten meat loaf very often, my dad did not like it, so mom never made it. It looked interesting, like a slab of meat. There was gravy and mashed potatoes. There was corn as well, the plate was very pretty.
“What is that?” Jennifer said and looked at me. She was holding the metal cover.
“It is meat loaf. Have you ever had it?” I said and she shook her head.
“My mom did not cook, all we ever had was either from a restaurant or a can. Is it good?” She said and I laughed.
“This is one of those things that a lot of people either love or hate. I am thinking it will probably be good since everything else has been.” I said and sat down.
I took a bite and not surprising it was amazing. The texture was different, but the flavor exploded on my tongue. Jennifer saw my face and sat down. She took a bite and smiled.
“Do you like it?” I said and she nodded.
“It is pretty good, feels a little different in my mouth but it tastes really good.” She said.
We finished our dinner, and I was again perfectly full. This chef must be a magician, he made meat loaf taste good. Mom never made it, but I had it before a few times at friend’s houses and I was not a fan. This one changed my mind. I crawled into bed and Jennifer snuggled up next to me. I heard her sigh deeply.
“What are you thinking pretty girl?” I said.
“I don’t know what to think. Is this our new life, having to fuck for food. Being naked all the time except when we leave the room and then we wear a dress that shows all our stuff anyway. Wearing these collars for the rest of our life? Cassie, are we going to have to do this with these people forever?” she said.
“I hope not, sweetie.” I said.
“How will it end then? They seem so controlling, how will we get away?” she said.
“Baby, you will just have to hold on for me until I can figure something out. I just don’t know how long that will take.” I said and I felt her take a deep breath.
“I know, I am sorry, I know you are trying. Please let me know how I can help.” She said and kissed my cheek.
“Well, there is one thing.” I said and she got up on her elbow and looked at me.
“What Cassie, I will do anything.” She said and I smiled.
“Will you make love to me?” I said and her face lit up.
“Cassie, I have been waiting for you to ask. I would love that.” She said and moved on top of me. I giggled and she smiled.
“You are very excited.” I said.
“Yes, I am, you are always the one that makes me feel good, I am happy I can finally return the favor. Do you hurt anywhere other than here?” She said and touched my shredded breast.
“No, and that only hurts if you press on the wound.” I said and she leaned over and kissed my nipple on my hurt breast.
“Did that hurt?” She said and I shook my head.
She kissed it again and then sucked on it gently. I shook my head again and she smiled. She kissed all around the bandage and then she moved to the other breast. Her little tongue was like heaven as she moved it over my sensitive skin. I closed my eyes and pulled my arms up over my head.
She moved her magical tongue down my body and was now looking at me from between my spread legs. She smiled and blew warm air on my open pussy. I groaned and moved my hips around.
“Did that hurt?” She said.
“Oh God no, Jennifer, it feels so good.” I whispered and she blew on my pussy again.
She lowered her head and then I felt the warm wetness touch my open lips. She moved slowly across my open pussy. It felt so good, I was breathing and trying to memorize this feeling. She slowly licked up and then she touched my clit gently. I whimpered and tried to push my hips towards her. She put her hands on my upper thighs and pushed me back down.
“Relax, let the feeling just linger, like you did with me.” She said softly. This little girl had been paying attention.
She kissed my inner thighs for a minute and then moved back to my pussy. I was sitting on the edge of a cliff, and she was holding me gently. I felt her breath and then her tongue touched my clit again. I whimpered and she pulled away again. She kissed my thighs and that felt good as well. She moved back again, and my release was hovering. I tried to grab it, but she pulled it away. I moaned and took a deep breath. She kissed my open lips again and then ran her small tongue inside me. I flinched and she pulled out slowly. I was moving my hips and she was kissing right on the edge of where I wanted her.
“Please.” I whispered and she giggled.
“Please what?” she said softly.
“Please, I need it.” I whispered.
She licked up the length of my pussy again and then she ran her tongue around my clit. I moaned and then she flicked her tongue across my clit, and I screamed. She latched onto it and sucked hard. My orgasm exploded and I arched my back off the bed. I could not make my mouth work so the sound was more like a gurgle. My body was out of control, and she was still sucking on my clit. I was shaking and convulsing, and she held on. I grabbed her head and held her in place as I curled my body around her. I was whimpering and shaking for a long time.
I finally relaxed and unwrapped my legs from around her head. She took a breath and laid her head on my belly. I held her head and rubbed it gently. I flinched and shivered a few more times as my body slowly recovered.
“Was that good?” She said softly and looked up at me. I looked down at her cute shiny face and I started laughing. I couldn’t stop the emotion, it flowed into me, and I could not stop laughing.
I laughed and held her head. I tried to stop, and she was looking at me strangely. I settled down and tried to catch my breath. I got control so I could talk.
“Remember when we talked about dumb questions?” I said and she smiled.
“So that was one?” She said and I nodded.
“That was beyond good, that was the best I have ever felt.” I said and she gasped.
“Even better than Marcus?” She said.
“Baby, you are going to have to teach him that.” I said and she giggled.
“That will be fun.” She said and moved into her position beside me. I put my hand on her warm thigh as she moved it over my belly.
“Yes, that will be a lot of fun.” I said and closed my eyes.
Marcus laughed as he walked into the room.
“You are seriously asking me this?” He said and sat on our bed. I climbed up on his lap and straddled him, kissing his lips.
“Yes, I am. Are you too scared?” I said teasingly.
“Shorty, you scare me at least twice a day, but I don’t think I am afraid of this.” He said.
“Then you will try it?” I said and he hugged me.
“You know you did not have to convince me; any man would fall over to do this with two beautiful girls.” He said and kissed my neck, I felt a tingle between my legs.
“But you have to listen to her and do what she says.” I said and hit him on the chest. He chuckled.
“Yes, ma’am. I will be a good student.” He said and I kissed him. I moved my tongue inside his mouth, and we wrestled. I loved kissing him.
He laid down and I was on top of him. I felt his huge cock under my belly. I wanted that monster inside of me, but I had to be patient too. Jennifer walked up and touched my shoulder. She was so cute, she looked very nervous.
“You have to get naked.” She said and I smiled.
“Marcus, there is your first command, make me naked.” I said and he ripped my t-shirt off. My boobs bounced free over his face. He kissed each of them.
He rolled over and flopped me onto the bed on my back. He pulled off my shorts and panties and threw them across the room. He looked at Jennifer.
“Next step, boss?” He said and she giggled.
“You have to kiss her slowly, start with her face and then move down real slow. She likes it when you suck her nipples.” Jennifer said.
“Whew, that is tough, but I will try.” He said and kissed my lips.
He kissed my cheeks and then my neck. He moved down slowly; he did suck my nipples a little. He moved down my belly and onto my upper thighs.
“Ok, kiss her thighs, she is very sensitive right here.” Jennifer said and I felt her touch my inner thigh. I flinched.
“I see, that is interesting.” He said and kissed where her finger touched. I groaned as he kissed up and down the inside of my thighs.
“Good, now move slowly to the middle, you have to go very slow. Start at the bottom and move up.” She said and his large tongue licked the inside of my open pussy. I whimpered and moved my hips.
“Ok, slow, don’t touch her clit. Tease her a little and then move back to the thighs.” She said and he moved his tongue around my clit. I gasped and tried to move my hips to get him to touch my little pleasure button. He laughed and then started kissing my thighs again. I groaned and lowered my hips.
“Good, now keep her on edge as long as you can or until she starts hitting you.” She said and he laughed. I heard his laugh echo around the apartment.
He did exactly as she said at least three times, and I was now sweating and breathing hard. I needed release badly. I moaned and grabbed his head.
“Please, please.” I said and he looked up at me.
“You have to say pretty please.” He said.
“Pretty fucking please!” I screamed and he sucked my clit into his mouth.
My orgasm exploded and I felt my body jump off the bed. He was holding my hips and then I felt Jennifer lay across my chest. I felt her little boobs smash against mine and that set me off again. I screamed and thrashed under my two lovers. My body felt like it was water and just wanted to move around. The pleasure was rippling through me. I was screaming and holding onto Jennifer. I moved my right hand down her back and grabbed her tight little ass. I loved her butt, I squeezed it and let my orgasm settle over me like a soft rain. I relaxed and sunk into the bed. I started to focus on breathing.
“Was that a good one?” She said.
“God, yes, it was great.” I said and I heard her giggle.
I opened my eyes, and she was lying next to me in the room of whiteness. I took a breath. I was holding her firm ass in my hand.
“Did you dream about me teaching Marcus how to eat your pussy?” She said and looked at me.
“Yes, as a matter of fact I did. You did a very good job as a teacher.” I said.
“You have the strangest dreams.” She said.
The door opened and the food guys walked in. The smell was wonderful again. They put the trays on the table and walked over to us.
“Okay, ladies it is ass day. I want you on all fours.” Black guy said to me. I sighed and got on my hands and knees.
“Little one, I like that position as well, but you can put your face on the bed with your pretty little ass in the air.” White guy said and Jennifer turned over and got in the position he requested.
I felt the black guy spread lube on my ass and I looked back at him. He was coating his cock with the lube. Maybe this might not be so bad. He grabbed my hips and pressed against my ass. I took a breath and relaxed, he pushed and then slid in. He pushed all the way in, and I felt his skin against my butt.
“Fuck, this is a tight ass, I knew it would be.” He said behind me as he held himself in me, rubbing my ass.
“I don’t know buddy; I am not sure I can get into this one.” White guy said and I looked at Jennifer. She had tears in her eyes. I tried to remember the last time she was fucked in the ass, and I thought it was probably the night at the Jamesons by Teddy’s tiny dick. That was a week ago, but it seemed like a lifetime.
“Take your time buddy, she is young.” Black guy said.
I reached out and took Jennifer’s hand. She squeezed my hand and I saw tears run out of her eyes.
“Relax baby, close your eyes and think of Willie.” I whispered.
“Who’s Willie, is that your dildo or something?” White guy said as he kept pushing against her.
“Dude, use some more lube.” Black guy said.
I saw the white guy pull away and then put lube on his finger and stick it in her. She grimaced as he ran his finger in and out of her ass. I saw him push two fingers in and she whimpered. He lubed her up and then stuck his cock back in her butt. He got in a couple of inches and then he pulled on her hips and drove into her. She screamed and squeezed my hand.
“Fuck, her ass is going to crush my dick.” White guy said.
“We can only hope.” I said and black guy laughed. White guy did not look happy.
He pulled out of her and drove back in; I saw her small body move with his thrust. Her eyes were closed, and she was breathing deep. He was fucking her now and she was trying to focus on something else. Black guy started fucking me and I closed my eyes as well.
They did not last long thankfully. I guess they were excited about ass day. They pulled out after filling us and put their cocks away.
“Enjoy your breakfast ladies, we will see you for lunch. Ass day is an all-day party.” Black guy said and laughed.
They left and I moved over to her. I put my arm around her, and she cried into my chest. She recovered relatively quickly.
“Are you ok baby?” I said.
“That really hurt, he was very big.” She said.
“I am sorry sweetie.” I said and rubbed her back.
“The black guy is bigger; he is going to hurt more.” She said.
“I will see if I can get them to not switch.” I said.
“That is probably a rule.” She said and I chuckled.
“Yeah, you are probably right. We really need a handbook.” I said and she laughed.
We got up and looked at our breakfast. It was an omelet. She looked confused.
“You are going to like this one for sure.” I said and sat down.
“I guess I need to learn more foods.” She said and took a bite. I could tell from her face that she liked it.
The breakfast was great again. I felt much better now with food in my stomach. We laid down on the bed again. We held each other for a while and didn’t talk. The silence was nice.
Our trance was broken by the door and the doctor and coach walking in. Her hair was loose today and there was a lot of it. It was very long and pretty. She had on her white coat over a blue dress. She knelt next to the bed and touched my belly.
“You are healing nicely; the lines are almost gone.” She said as she rubbed across my belly and thighs.
“The only thing that hurts is my breast.” I said and she nodded.
“Let’s take a look.” She said and started to pull off the bandage. I grimaced a little, mostly from the tape pulling on my skin. I felt her touch my wound.
“Cassie, this looks good. The skin is closed, I don’t think you need a bandage anymore. We just need to keep applying salve.” She said and I looked down. The skin on my breast was smooth but there was a thick red line that looked like it was under my skin. I ran my fingers across it, and it felt weird.
“Will it leave a scar?” I said.
“No, I don’t think so.” She said.
“That is good for Taylor.” I said and looked up.
“Yes, it is. Victor will be pleased.” She said.
“I would have liked to see Mr. Jameson get in trouble though.” I said.
“You and a lot of other people. Jennifer, let me take a look at you sweetie.” She said and I moved closer to coach.
I sat up and leaned my back against him. I held out the tube of salve. He took it and didn’t complain. He spread the salve over my breasts, coating them. He spread more on my belly and then on my thighs. His hands felt nice on my skin, I felt nice for a man to touch me that didn’t want to hit me or eat me. I moved over and laid on my belly. He started rubbing salve on my back.
“Jennifer, it looks good, I think a few more days of salve and you will be good as new.” Doctor said.
She took the tube and started to spread it on Jennifer’s small body. I saw Jennifer watch the doctor closely and I could tell she was enjoying her touch as much as I was coach’s.
“Girls, I am going to add a massage into your schedule. It will help your muscles recover and go well with the training.” Doctor said.
“Ok, I like massages.” I said and thought of Frances and his magical fingers.
She finished with Jennifer and then she gave us our pills and left. Coach was still rubbing salve on my butt.
“Coach, where are you taking us today?” I said.
“Victor wants to see you.” He said and I looked up at him.
“Why?” I said.
“I think he wants to see how you are healing. He is getting a little bit of pressure to schedule the photo shoot. The photographer will be here tomorrow, and he really wants to use you guys. If you are not healed enough, he will have to use other girls, the rate will be less, and Victor will not be happy.” He said.
“Why does he want us? There are plenty of pretty girls around here, much prettier than us.” I said and coach laughed.
“It is cute how you think like that, you have more orders pending than all the other girls combined. Victor is trying to schedule you for something every day and he is itching to get started.” Coach said.
“Great, I can’t wait.” I said.
Coach rubbed my butt and thighs for quite a while, and I did not complain. I heard the door, and I looked up to see trainer guy. Our days are starting to fill up quickly. Coach got off the bed and got two dresses out of the cabinet. He slipped them on us and clipped on the leash. He handed it to trainer guy, and he led us out into the hall. I tried to look around closely as he led us like puppies through the halls. He opened the door to the workout room and walked us to the complicated machine.
He showed us three exercises he wanted us to do, one of them was of course the leg spreader thingie. I think he liked watching us on that. I started on that one and Jennifer started on some kind of back exercise. Trainer guy watched me spread my legs to push the weights out. My dress pulled up to my waist and my pussy opened wide. I saw a different trainer guy walk by leading a short brunette girl. He looked at my pussy closely, even pausing a little. I smiled at him; this place was so strange.
We worked out for an hour, rotating through the three exercises the whole time. We were both soaked in sweat, the dresses pretty much transparent. We got a lot of looks from all the trainer guys as we walked to the showers. We entered the dressing room, and it looked a lot like our dressing room at school now that I paid attention. I had never looked really close at it before. Trainer guy pulled off our dresses and tossed them in the box with wheels. He grabbed two towels and led us into the shower area. We were able to take real showers today with all our bandages removed. It felt so good, it was nice to feel clean all over. We wrapped our towels around us, and he led us out of the dressing room. I noticed a hallway leading out of the dressing room on the opposite wall. It did not look like the others in the building.
He led us through the halls in our towels. It struck me that I never saw any other girls in towels, I wondered if our trainer guy had a fetish. We got back to our room, and I tossed my towel in the corner and stood next to the wall. He stretched my leg up and held it next to my head. He moved his hand down and started playing with my pussy.
“Do you like it when we wear towels?” I said and he looked at me.
“What are you talking about.” He said and slipped a finger into me.
“I just noticed we are the only ones that walk through the halls in towels. Isn’t the rule that you have to wear the white dresses when you are not in the room?” I said and he smiled.
“Yeah, I do like seeing you guys in towels. The rule is not to be naked in the hallways, towels are approved but if they fell off, we would have an issue. That is probably why most guys don’t do it, but I figured it was worth it to see you hot little sluts in towels.” He said.
“Would you get in trouble if our towels fell off?” I said and he smiled.
“Always thinking, you are something. If your towel falls off, you go in the dungeon for a day, and I get re-assigned to a different girl. I would be sad but not as sad as you.” He said. I decided I would be holding my towel a little tighter in the future. He stretched my other leg, there was no pain anymore.
“So, who is handling payment?” He said as he lowered my leg.
“I will.” I said.
“Ok, I want to fuck your pretty face again. On your knees.” He said and I knelt.
He shoved his cock into my mouth and started pumping. I put my hand on his shaft.
“Put your hands behind your back.” He said and I followed directions.
He put his hands on the side of my head and started fucking my face. He drove his cock into my throat and held it there for a few seconds. He pulled back and just used my mouth like a pussy. Drool was leaking out of my mouth, hitting my breasts. I closed my eyes. He fucked me for another few minutes and then blasted the first load into my mouth. I swallowed all three of his loads and then he pulled out.
“Thank you, I do love all of your holes.” He said and tucked his cock away.
He pulled Jennifer over and put her up against the other wall. He stretched her leg up and played with her pussy. I got up slowly and wiped off my mouth with the sheet. I sat and watched him stretch her other leg and fiddle with her pussy. He finished and left. She sat next to me.
“Are you ok?” She said.
“Yeah, I am wondering if a day in the dungeon would be worth getting him re-assigned.” I said.
“Cassie don’t even say that as a joke. We may get someone worse, and I do not want you in that room.” She said and grabbed my arm. I looked down and she was scared.
“I am sorry baby; I was just angry. I would not do that.” I said and she sighed.
“Good, because that would be really bad.” She said.
We laid down and held each other. I did not realize I had fallen asleep until I felt someone shaking my arm. I looked up to see white food guy.
“Wake up princess, time for more ass-fucking.” He said and smiled.
I groaned and got in the position. Jennifer got next to me, and we held hands and closed our eyes. They lubed us up and fucked our asses. The black guy fucked Jennifer, but he went in easier this time, I guess she was stretched out a little from this morning. They fucked us for a few minutes and then left. I felt the cum running down my leg. I used the sheet to wipe it off. I hoped Victor was right in that we would get new sheets after dinner.
We had a roast beef sandwich, and it was excellent. My stomach was very happy. The rest of my body wasn’t so sure. The “payments” were starting to wear on me. It was noon and I had already been fucked in the ass twice and face-fucked brutally. That was not a good morning. I was simmering in my anger when a tall man walked into the room. I did not recognize him, but he was dressed like trainer guy, so I knew he was staff.
“Ladies, I am here to take you to your massage.” He said, his accent was different, it was nice. He was dark-skinned but I am not sure he was black, more of a mixture. His eyes were very pretty.
He handed us two dresses and we put them on. He clipped on the leash and led us out of the room. We headed the same way as the gym but did not turn down the first hallway. He turned down the second hallway and led us into a door about halfway down the hall. It was a room a little bit bigger than our room, but it was coated in soft yellow light. There was soft music playing and there were two tables with sheets on them.
“Take off your dresses and get on the table, face down to start.” He said and I pulled off my dress and climbed onto the table. I was getting way too comfortable being naked around strangers.
I laid down on the table and saw another man walk in and stand next to Jennifer’s table. He was tall as well, but he was definitely black. He was not huge like all the other black guys around here; he was still muscular but more defined and slender. I saw him pull out a bottle and spray some oil on his hands. He started on her foot, and she moaned immediately. I felt hands on my foot, and I understood.
My massage guy was very good. He rubbed all the sore muscles and some I didn’t even know were sore. My body was feeling wonderful. His hands were soft and warm. He was very careful around my butt wound but he was able to work on my thighs and butt easily. I felt the oil leak down between my legs as he rubbed my butt. He tapped me and told me to turn over. I flipped and he started at my head.
He massaged my scalp and my head, and I almost went into la-la land. He worked his way down my chest and belly and was soon massaging my thighs again. He worked them and then he spread my right leg out, hanging it over the edge of the table. He worked on my thigh in this position, and it felt totally different. No massage therapist would be able to put a client in this position, so I guess it was unique. He worked my left leg and spread it over the over side of the table. I was spread eagle on the table as he worked on my legs.
He worked on my feet again and I looked over and Jennifer was in the same position. He moved up my leg slowly and was back on my thigh, his fingers moving very close to my open pussy. He worked the other leg and then I felt him grab my hips and pull me closer to the end of the table. I looked up and then I felt his cock slide into my pussy easily. He buried himself and then started massaging my hips as his cock was embedded in my pussy.
“I figured it was easier to do payment this way, like it is part of the massage.” He said and I smiled.
For some reason I was not minding this payment. I turned my head and Jennifer was paying her guy as well. He massaged my hips and then my chest again. He pulled my legs up on his chest and started working on my calves as he moved in and out of my pussy. He was able to massage both of my legs and then he pushed in and completed the transaction. He pulled out and laid my legs down. He moved over and ran his hands slowly down the length of my body. It felt really good.
“Stay here for a minute. I will be right back.” He whispered and I was happy to follow directions.
I looked over at Jennifer and she was smiling at me. I could tell she was feeling as good as me. The men returned with water for us and helped us sit up. I was dizzy for a minute, and I drank the water.
“You will take a bottle of water with you; I need you to drink the whole thing. We released a lot of toxins over the last two hours.” He said and I looked at him.
“We have been here two hours?” I said and he nodded. I would not mind this every day.
He slipped my dress over my head and then helped me stand. I held onto the table until I got my bearings. My head cleared and I felt better. He clipped on the leash and led us out into the hallway. We walked back to our room; my body was feeling better that it has in a long time. He sat us on the bed in our room and pulled off our dresses. He smiled and left the room. Jennifer looked at me.
“What was that?” She said.
“I am not sure, but I can’t wait until tomorrow to do it again.” I said and she nodded.
She snuggled next to me, and her skin felt different with the oil on it. We laid down again and held each other, waiting for the next cock.
I heard a noise and opened my eyes; I had been napping. I saw coach pull out two dresses and walk over to the bed. He looked down at us.
“Did you like your massage?” he said and we both nodded.
“That was amazing.” I said and he smiled.
“Victor hired those two brothers from the best salon in France. He pays them a fortune, but they keep the girls happy and healthy, so they are worth it.” He said.
He held out his hand and I took it and sat up. He put my dress over my head and helped me stand. He did the same for Jennifer and then he clipped on the leash.
“Where are we going?” I said.
“To see Victor.” He said and I looked at him.
“Don’t worry, he is in a good mood.” He said.
He walked us out of the room, and we headed the opposite direction from the gym. We went past the hallway that led to the dungeon. He turned down the next one and then we went into a door that coach opened with his card. There was an elevator with a man standing next to it. He was older and looked like a normal guy you would pass on the street.
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