Poor Little Cassie
Copyright© 2021 by Demonhead
Chapter 90: Helena
Fiction Sex Story: Chapter 90: Helena - 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
Cassie walked into the dining room at lunchtime in her yellow sundress, feeling pretty and calm for a change. The rest of her gang were now dressed as well, looking incredibly cute even with clothes on. Cassie noticed Helena pushing an empty cart on her way to the kitchen. As she walked past them Cassie saw sadness in her eyes even though she smiled as she passed. Cassie watched her disappear through the doors. She felt a touch on her arm and saw Marcus smiling down at her.
“Go shorty, I’ll save you a seat.”
Cassie kissed his arm and followed Helena into the kitchen. She saw Gwen working with Helena to load the cart with plates of food. She noticed Gwen looked much more confident talking to Helena, who was nodding and seemed to be concentrating on her task. Gwen finished and Helena rolled the cart towards Cassie who was standing next to the door. As Helena turned from Gwen Cassie saw Helena’s face change from focused to sadness. She stopped Helena by touching her arm.
“Hey, how are you doing?” Cassie asked and she saw Helena straighten up her shoulders and look at Cassie.
“Fine boss. Do you need something?”
Cassie stared at Helena and saw her eyes looked sad even though her face was smiling. “No, I’m good.”
Helena nodded and pushed the cart through the doors. Cassie turned to Gwen, who looked nervous again.
“Gwen, how is she doing?”
Gwen looked at the doors and then back to Cassie. “I guess she is ok, she seems to be focused like usual. She is always very professional.”
Cassie looked back at the door. “Ok, how are you doing? Did John help you?”
“Yes, boss, he is great. I’m very excited. Thank you so much.”
“Good, we’ll be staying a couple more days here.”
“Okay, thank you. I will make sure we are stocked before we leave.”
“Thank you, Gwen,” Cassie said and heard a sound behind her.
“Boss, what are you doing back here? Do you want a turn?” Cassie turned to see Jo bouncing over pushing an empty cart.
Cassie looked at Jo’s outfit; she had on a white shirt with the top two buttons open and a very short red plaid pleated skirt. She was wearing white fishnet stockings, and Cassie could see glimpses of the lace at the top when she moved. She looked back at Jo’s face.
“Where did you get that outfit?”
“Jennifer helped me with it. She said the boys would like it,” Jo said and turned, the tops of her stockings and some thigh showing as her skirt flared.
“Yes, they will definitely like that. Jo, are you ok dressing like that?”
“Yes boss, I feel pretty, and Jennifer said it was safe, the boys are nice, and the staff has been wonderful since ... you know,” Jo said.
“Then I’m ok with it. How’s your sister? She said she was fine.”
“She’s a liar. She cries every night, I try to help her, but she keeps saying she’s okay.”
Cassie frowned. “Has she talked to Dr. Trish?”
“Yes, she said she’s very nice and it’s helping.”
“Is it ... helping?”
Jo frowned and shook her head. “I don’t think so, she seems to be so sad when no one’s looking.”
“Thanks, I think Gwen needs you,” Cassie said and nodded to Gwen, who had moved next to them.
“Oh, sorry,” Jo said and turned to Gwen.
Cassie turned and went into the dining room. Travis was teasing Helena, and she was smiling. Cassie watched her closely and saw her face change after she moved away from Travis. She was wearing the white shirt and black skirt from before with black stockings and black heels with her dark hair pulled back in a ponytail. She was very pretty and seemed to be fooling everyone with her smile. She saw it again as she put Kelcie’s lunch in front of her. Cassie sat next to Marcus and sighed.
“What’s going on Shorty?”
“I think Helena is struggling.”
“It’s understandable.”
“Yeah, I have to remember that it is just as hard to recover from one rape as it is from 20.”
Marcus sighed and leaned over, kissing Cassie on the forehead. “Help her shorty, it’s what you do.”
Cassie smiled at him. “You’re a very smart giant man.”
“That’s what they tell me.”
Cassie ate a wonderful roast beef sandwich. Her pussy was very satisfied as she still felt Taylor’s tongue. Jennifer was smiling and giggling with Jo, her pussy obviously happy after her shower adventure. Cassie watched Helena closely and tried to come up with a plan.
Everyone finished eating and Cassie noticed Jo and Jennifer were clearing the dishes. Cassie stood up and walked over to Jo.
“Jo, where’s your sister?”
Jo looked at Cassie with a frown. “She said she didn’t feel well and went back to the room.”
Cassie tilted her head and stared at Jo.
“Cassie, she was crying,” Jo said softly.
Cassie felt her anger rise rapidly and she clinched her fists. “Oh, Fuck no,” Cassie said under her breath and walked over to Travis.
Travis was laughing as Kelcie and Taylor were tickling him. She stopped next to them, and they all looked up at her.
“Travis, I need you.”
Cassie’s tone brought everyone back to serious.
“Sure boss, what do you need?”
“Meet me on the outer deck in 10 minutes,” Cassie said and turned, walking over to the Captain.
“Schmitty, I need the key.”
Captain Schmidt looked at Cassie. “Boss, what’s going on?”
“I have it under control, I just need the key to the lower room.”
Captain Schmidt pulled his keyring out of his pocket and handed the key to Cassie. Cassie tucked it in the pocket of her sundress. Helen looked at her daughter.
“Honey, what’s going on?”
“Mom, I’m good. I just need to take care of something. I’ll be alright; I’m taking Travis with me.”
“Okay,” Helen said gingerly as she watched her daughter walk briskly out of the room. Helen looked over at Marcus who nodded to her.
“Helen, she’s okay. I think there may be some vengeance happening soon.”
Helen looked at the door and then back to Marcus. “Wait, what?”
Cassie tapped on Helena’s door and heard a small voice.
“Come in.”
Cassie walked in and saw Helena curled up in the middle of the bed.
“Jo, I told you I’m fine,” Helena said.
Cassie walked to the edge of the bed, Helena was faced away from her and Cassie could hear her softly crying.
“Jo said you were a liar,” Cassie said, and Helena popped up, looking at Cassie with fear on her face.
“Boss, I’m sorry, do you need something?” Helena said frantically, adjusting her skirt and hair and sliding off the bed.
Cassie stepped in front of her and touched her shoulder. “Helena, stop, look at me.”
Helena looked at Cassie, her eyes wet and red. Cassie frowned and touched her cheek, wiping off some moisture.
“Helena, it’s ok to be sad. You don’t have to hide it.”
Helena shook her head and wiped her eyes. “No, I’m ok, really.”
“Helena, you were raped, it’s ok not to be fine.”
Helena opened her mouth to talk and then closed it and started to sob. Cassie pulled Helena’s head to her chest and rubbed her back as the girl cried.
Cassie felt her anger simmer as Helena cried in her arms. She took a deep breath to try and focus her rage. She felt Helena start to get control; Cassie pulled her off her chest and looked in her eyes.
“I’m so sorry I’m so weak,” Helena said softly.
“What are you talking about?”
“You and the girls went through much worse than I did, and you are all so strong.”
Cassie chuckled. “We weren’t strong a couple of months ago. I didn’t even recognize my mom for a while. In fact, when they rescued me, my mind was so messed up I thought I was a dog.”
Helena looked at her strangely.
“Helena, I almost jumped off the boat just a couple of nights ago. We’re all still working on this, and we’ll continue working for a long time. Would you like me to help you?”
“I have talked to Dr. Trish.”
“I know and you need to keep doing that, she’s amazing. Would you like me to give you a boost that might help you move a little faster?”
Helena sniffled and took a breath. “I guess so, what do I have to do?”
“Just follow me and open your mind,” Cassie said and held out her hand.
Helena took it and Cassie led her out of the cabin. They walked down the hall and up to the outer deck. Travis was leaning on the railing and Cassie nodded to him.
“Travis will be helping us,” Cassie said and walked past him, Travis following.
“Help us with what?” Helena said.
“With the beginning of your recovery.”
Cassie led them downstairs to the lower deck, they approached the large metal door, and Cassie pulled the key out of her pocket. She turned to look at Helena.
“Cassie, what’s in there?”
Cassie took Helena’s other hand and held them both. “This is where you have to open your mind. Did you hear what Cooper said to me about vengeance?”
Helena nodded. “Yes, Jo and I were listening.”
“Good, this is your vengeance. Nathaniel is in there.”
Helena started to pull away, but Cassie held her hands. “No Cassie, I can’t see him.”
“Helena, yes you can. The first step to recovery is to confront the issue. I’m sure Dr. Trish has said that to you.”
Helena nodded tentatively.
“You have the advantage of having him here so you can confront him directly. Let’s go in there and if you feel at any time you want to leave we will.”
“Okay,” Helena said hesitantly.
Cassie opened the door and Travis put his hand on the door over her head. “Not sure what you have planned but let me go first.”
“Not a problem, sir, lead on,” Cassie said, and Travis smiled.
Cassie walked into the room behind Travis, holding Helena’s hand. Nathaniel was sitting on the floor against the wall with his right hand up in the air, locked to a chain. He had a shoulder wrap on his left arm. Cassie chuckled, been there, done that. He looked up with a look of surprise and then he smiled.
“Coming back for more?” Nathaniel said with a sinister grin.
Helena stopped and Cassie turned. “He can’t hurt you anymore,” Cassie said softly as Helena started to tremble.
Helena stared at Cassie and tried to draw strength from her. She took a breath. “Cassie, I’m not as strong as you.”
Cassie smiled. “Yes, you are, you will see. Hang onto my hand and you’ll be ok.”
Helena nodded and then flinched as Nathaniel spoke again.
“I will be happy to take care of you both,” Nathaniel said, and Travis stepped in front of him with his fists clenched.
“Travis, no, this is for Helena,” Cassie said, and Travis stared down at Nathaniel.
“Yes, the girls know what they want and it’s not chocolate, my big bull,” Nathaniel said, and Travis moved towards Cassie.
“Cassie, I could make him stop talking,” Travis said, and Cassie touched his arm.
“I know but I have something else planned,” Cassie said and glanced over at the other side of the room. She saw the large bed with the red silky sheets. There was a table or bench of some sort with straps all over it and she smiled.
“Travis, can you put him on that bench face down?” Cassie said and pointed.
Travis looked at the bench and then at Nathaniel. “Do I have to be gentle?”
Cassie snickered. “Absolutely not.” Cassie handed Travis the key.
Helena flinched again when Travis unlocked the handcuff and then grabbed Nathaniel by the hair, dragging him across the floor as he screamed.
“Helena, come with me,” Cassie said and walked over to the side wall.
Cassie looked up to see the whips and canes and other things she didn’t recognize. It reminded her of the cabin and coach explaining all the things in that cabinet. She caught a memory of Brynn, and she shuddered. Cassie took a deep breath and touched the cane and one of the whips. She noticed there were a few drawers, and she pulled the top one open, seeing a bunch of different kinds of clamps. She caught a shiver when she remembered the jumper cables in Carl’s garage. She picked up one of the bigger ones and the teeth were sharp. Helena gasped and shivered.
“Do you think this would hurt if we put it on his balls?” Cassie said and Helena gasped again as Cassie held up the large clamp.
“Cassie, what are we doing?”
Cassie took Helena’s hand and kissed her cheek. “Helena, he hurt you and he took something from you. We are going to hurt him until he understands what he did to you. All you have to do is look into his eyes and tell me when he has had enough. Do you think you can do that?”
“What the fuck? What are you doing? Oh, fuck, stop it!”
Cassie and Helena turned to see Travis slamming Nathaniel down on the bench. He strapped him face down so he couldn’t move. His chest was on the bench with his legs hanging off the edge. He was struggling and cursing.
Helena remembered her head bashing against the footboard of the bed as he fucked her savagely. She remembered him slamming Jo’s head down on the floor viciously. She turned back and looked at Cassie.
“Yes, I can do that, let’s see what’s in the next drawer,” Helena said and smiled.
“Good girl,” Cassie said and pulled open the second drawer.
Cassie was shocked to see a collection of dildoes and plastic cocks. There were a lot of them in all shapes and sizes, and she saw a leather brace or something. She picked it up and looked at it.
“That’s a harness for a strapon.”
Cassie looked and saw Travis walking up with a smile.
“What’s a strapon?”
Travis chuckled. “It’s funny with everything you’ve gone through that there are still things you don’t know.”
“Well, no one ever used something like this on me.”
“True, they didn’t need to, they had the real thing,” Travis said and took the harness from Cassie.
Travis picked up a large black dildo that looked like a cock and attached it to the harness. Cassie smiled as she saw the cock thing hanging from the harness.
“Do you want to try it on?” Travis said and held it up.
“Oh yes, how do you do it?” Cassie said.
Travis knelt in front of her and wrapped the harness around her waist, running a strap between her legs and attaching to the harness in the back. He tightened it and stepped back. Cassie looked down and she had a cock sticking out in the front. Travis laughed and she looked up.
“Sorry, it just looks funny over your sundress.”
“I could take care of that,” Cassie said.
“Hey boss, your call. Most of the times these things are used everyone is naked.”
“Take it off.”
Travis unhooked the harness, and Cassie pulled her sundress off. Travis smiled as he saw her breasts move slightly as she tossed the dress on the bed. He looked down at the smooth pussy and shook his head. His cock was now raging in his pants.
“You are so beautiful; I will never get tired of seeing this.”
Cassie looked at his pants and chuckled. “I can tell, maybe you will get a reward later for your help?”
Travis knelt and attached the harness to Cassie. He had to focus as her breasts were inches from his face as he worked. He finished and kissed a nipple before he stood up. Cassie chuckled.
Cassie looked down and the cock was now covering her pussy. She moved her hips side to side and watched the cock dangle.
“It must be weird to have one of these attached to you all the time.”
Travis laughed. “You get used to it.”
Cassie turned and saw Nathaniel strapped on the bench, his head away from her so she was looking at his legs. He was wearing brown pants and a white shirt. They were both dirty, Beatrice obviously didn’t care about his hygiene. She walked over and touched his butt. He flinched.
“What the fuck?” Nathaniel screamed.
“Just relax my little piece of shit, you might enjoy this,” Cassie said, and Travis laughed.
“Travis, I think we need to get these pants off.”
Cassie chuckled as Travis ripped off Nathaniel’s pants, underwear and shoes. His hairy butt was sticking out and she stepped forward. She slid the plastic cock between his cheeks, and he screamed.
“What the fuck are you doing?”
“Pretty much what you did to Helena, you shoved your tiny dick into her against her will so now I’m going to shove this into you. I’m assuming it’s against your will but hey, you never know. Nathaniel, are you excited about getting fucked in the ass?” Cassie saw Helena put her hand over her mouth to keep from laughing out loud.
“Fuck you!! You can’t do that, that’s rape!”
Cassie laughed and pushed the huge plastic cock against his asshole. Nathaniel screamed.
“When I get out of here, I will fuck you to death, bitch!” Nathaniel screamed and Cassie pushed harder.
Travis stepped forward and touched Cassie’s arm. Cassie tried to push the cock into Nathaniel again, but she met resistance. She got frustrated and looked at Travis who was holding a bottle of lube.
“I don’t need that, I want it to hurt,” Cassie said harshly as she continued to push.
“Cassie, it’s not an issue of pain, sometimes it’s not possible without it,” Travis said.
Cassie looked at Travis and he was frowning. “Cassie, I did this enough when it was not wanted, believe me you need this if you want to get that in there.”
Cassie remembered Fridays and watching Travis drive his cock into Beth’s ass. She remembered Neal slamming into her own ass, even after a brutal gang rape the night before. She sighed and grabbed the bottle. She squirted a glob on the plastic cock and spread it around. She handed the bottle back to Travis and took a breath. She pushed hard and felt his ass give way, she slid into him and smashed against his ass cheeks.
“Argghh, fuck, pull it out, god damn, that hurts!”
Cassie held her body against his and looked at Helena standing in front of Nathaniel. Helena shrugged her shoulders and Cassie noticed Nathaniel had his head down as he whimpered. She looked at Travis.
“Travis, he needs to look at her.”
Travis grabbed Nathaniel’s hair and lifted his head. “Look at her you fuckhead!”
Cassie pulled out and slammed back into his tight hole. He screamed again.
“Mother fucker! This is not right!”
Cassie drove the cock deep and held it. “You’re right you son of a bitch, this is not right but this is how it feels to be raped. Nice, isn’t it?” Cassie screamed at him and ripped the cock out and back in.
Nathaniel grunted and Cassie started a nice rhythm. She could feel his ass loosening up as the resistance lessened. He was moaning and grunting as she powered in and out of him. She looked up at Helena; she was staring at Nathaniel, focused on his face. Cassie held the rhythm for another minute and then stopped with the cock buried deep inside him.
“Helena?” Cassie said and Helena looked up.
Nathaniel was making strange noises, and Cassie could hear his ragged breathing.
“Cassie, I don’t think this will work,” Helena said and looked back at Nathaniel.
“Oh baby, it’ll work. We’ll do this as long as we need to, but he will eventually regret what he did to you.”
Helena looked back up at Cassie. “I think he passed out.”
Travis lifted his head and nodded to Cassie. Cassie pulled the cock out of him and walked around to look at his face.
“Okay, I guess we’re done for now. Travis, can you put him back where he was?”
“Do I have to dress him?”
Cassie chuckled. “Nope, I think it might be naked day down here.”
Travis laughed and unstrapped Nathaniel. He drug him across the floor and pulled off his shirt before cuffing his right arm again. Cassie snickered when she saw Nathaniel slumped naked against the wall with his hand in the air. Travis helped her out of the harness and held it out.
“I guess we need to clean it,” Cassie said.
“Ya think?” Travis said and smirked.
“There is a sink over there, bring it and I’ll wash it,” Cassie said and walked over to the sink.
Travis saw her tight ass as she walked and felt his cock react again. He carried the strapon over and put it in the sink. He moved Cassie aside.
“I’ll take care of it, you go to her,” Travis said.
Cassie looked over and saw Helena sitting on the bed with her head down. Cassie walked over and sat down next to her. Helena looked at her and moved her eyes up and down Cassie’s body.
“How are you so comfortable naked?”
Cassie smiled. “Believe me, you really don’t want to know the details.”
“Yeah, I guess not. That was tough to watch.”
Cassie rubbed Helena’s arm. “Was it too much? You don’t have to be here in the future.”
Helena looked at Cassie and her eyes were bright. “No, I want to be here. It was just harsh but still not as bad as what he did to us.”
“That a girl. We can try again later tonight.”
“Really? You want to do this more than once a day?”
“Helena, I will do this as much as it takes until he looks you in the eye and apologizes and you believe him.”
“Hmm, not sure that will ever happen.”
“Then he will be very sore when we get back to the states.”
Helena snickered and Cassie hugged her. Travis walked up and stood next to the bed. Cassie noticed his pants had a huge lump in them. She whispered in Helena’s ear.
“I need to thank Travis for his help, do you want to go back up?”
Helena looked at Travis and then back at Cassie. “No, can I stay and watch?”
Cassie smiled. “Absolutely, you can see what love is supposed to look like.”
Cassie moved away from Helena and laid down on the bed. She looked at Travis and spread her legs slowly. Travis smiled as he looked down at her glistening pussy.
“Come on big boy, time to get your reward,” Cassie said and squeezed her breasts.
Travis ripped off his pants and stepped to the edge of the bed. He grabbed Cassie’s legs and pulled her closer, holding them apart as he slid his rock-hard cock into her wet soft pussy. Cassie groaned as he bottomed out inside her body.
“Oh God, that feels so good,” Cassie moaned. She moved her left arm and felt Helena. Helena grabbed her hand and held it. Cassie looked up at her and smiled.
Travis held her legs and powered into her slowly. His strokes were long and steady, and he felt her getting slicker as he easily split her lips with each stroke. He pushed her legs a little to get better leverage and continued his cadence. He noticed Helena was holding Cassie’s hand and that made his cock a little harder. He sped up slightly and Cassie groaned and pushed her hips up to him.
Cassie felt his huge cock rubbing her pussy wonderfully, big enough to touch good places but not too big to stretch her out. She wondered if there was a cock that was too big for her now. She felt a small tinge of sadness as she thought about all the cocks that had been inside her over the last few months. She thought back to last December laying in her bed rubbing her virgin pussy when the doorbell rang and changed her life. Travis sped up and she remembered Tony ripping her virginity from her on her parent’s bed begore he let his friend fuck her too. It was a perfect introduction to sluthood. She felt Travis push hard and heard his groan. Her pussy soaked up more cum, she had a lot more work to do with Dr. Trish.
Travis pulled out and laid down on the bed, his wet cock flopping on his thigh. Cassie sat up and kissed Helena.
“That is what it’s supposed to look like.”
“It was beautiful,” Helena said softly.
“Do you want to try it?” Travis lifted his head and Cassie laughed.
Cassie grabbed his soft cock and wiggled it. “Not right away, relax.”
“Yes, I think so,” Helena said softly.
Cassie looked back at her and smiled. She hugged Helena and whispered. “Good girl.”
Cassie looked at Travis over Helena’s shoulder. “Now I’m hungry, take me to dinner?”
Travis laughed and fell back on the bed. “Cassie, we literally just ate lunch.”
Cassie grunted. “Dammit, Travis, I think you broke my pussy.”
Helena laughed and Cassie kissed her on the nose.
Taylor stepped out of the pool and walked over to the lounges. She saw Helen, Kelly, and Dr. Janice laying in their bikinis. She grabbed a towel and wiped off most of the water over her blue bikini. She stepped in front of Kelly’s lounge and the pretty brunette raised her sunglasses and looked at the young girl.
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