Poor Little Cassie by Demonhead Copyright© 2021 by Demonhead Chapter 92: More Captain and Taylor’s story Cassie opened the cabin door slowly and peeked inside. She saw Travis on the bed on his back with Helena sitting on him. She grabbed Taylor’s hand and led her silently into the room. They approached the bed and saw Helena’s shirt was still on but open, her plump breasts hanging from her chest as she leaned over with her hands on Travis’s chest. Helena’s long dark hair was hanging around her head, giving her the look of a crazy witch. Travis was smiling and turned his head to look at Cassie. “Comfortable?” Cassie said and Travis smiled. “Yes, very much so.” Helena turned her head slowly and Cassie saw her eyes were slightly glazed but she had a small smile on her face. “So big,” Helena said softly and slowly. Cassie stepped forward and moved some hair so she could see all of Helena’s face. She kissed her lightly on the lips and Helena’s smile grew a little bigger. “Take your time, enjoy him. You control it all,” Cassie said and kissed Helena’s nose. Helena took a deep breath and moved her hips slightly, wiggling them and then lifting them to let the humongous black cock slide out of her pussy almost entirely. She stopped with a few inches still stuffed inside her and then lowered her hips very slowly until she was sitting on him again. She lifted her head and let out a slow deep moan as the warm piece of stiff meat settled against her womb. “Oh God, that feels so good,” Helena said, and Cassie giggled. Cassie felt something and looked down to see Taylor on her knees in front of her, working on her skirt which quickly slid down her legs. She shivered as Taylor’s tongue licked slowly across her smooth pussy, placing her hand on the top of Taylor’s head. Cassie spread her legs a little and the magical tongue wiggled between her lips. Her nipples were now rock hard, and she felt something on her breast. She looked down to see Travis’s dark hand covering her right breast. “You don’t have enough with one girl?” Cassie said and he chuckled. “Oh, she is more than enough for me, but I will never be able to resist these beauties,” Travis said and squeezed her breast gently. Cassie moaned and rubbed Taylor’s head while Travis massaged her breast. The stimulation was hitting her from two different directions and her body was starting to respond. Travis pinched her nipple softly as Taylor flicked her warm tongue over her clit. Cassie groaned and shuddered as her orgasm started to build. Taylor ran her tongue around her clit and then sucked it on her lips. Cassie felt her pleasure erupt and she let out a small squeal. Travis held onto her breast and Taylor wrapped her arms around her thighs as Cassie trembled through her orgasm. Taylor pulled back and licked her lips. Cassie moaned and continued to shiver. Taylor looked up to see Travis holding onto Cassie’s breast. Taylor stood up and hugged her wonderful friend, trapping Travis’s hand between them. Cassie kissed her and ran her tongue inside Taylor’s mouth. Taylor moaned and kissed her back. Helena watched all of this with a hard cock buried in her body. A very large cock, in fact the largest one that had ever been inside her and now the one she would measure everyone against for the rest of her life. All this sex around her was making her lose herself in the pleasure. She thought about her momma, and would she understand? She thought about Jo and how she could keep her safe from all of this. Was this something she needed to protect Jo from? Could something that feels so good be bad? Helena’s mind continued to race until she felt her breasts squeezed. She opened her eyes to see Travis staring at her as he massaged her breasts. “What are you thinking about pretty girl?” Travis said and Helena felt herself blush. Helena watched Cassie as she climbed onto the bed naked. Taylor ripped off all her clothes and climbed on top of Cassie. They were both so beautiful and confident. They started kissing and Helena looked back at Travis. “I’m not pretty,” Helena said as she watched the two gorgeous girls. Travis chuckled. “I beg to differ, you are very pretty, even more lovely when you sit where you are now.” Helena giggled and Travis moaned as her pussy vibrated around his cock. “You’re just saying that because we’re...” Travis put his finger over her lips. “You listen to me little lady, I have noticed you ever since we stepped onto this boat. Don’t think that men don’t look at you and wonder how nice it would be to kiss you.” “To kiss me?” Helena said and wiggled her hips. “Yes, to kiss you. What I am getting to do now is beyond anyone’s imagination. However, the best part of all of this is looking at you.” Helena blushed again and laid down on Travis, her breasts smashing against his chest. She shivered as he wrapped his arms around her and hugged her, his cock flinching inside her. “You like this?” Helena said. “Oh baby, your body feels so good against me. Are you comfortable?” Helena snuggled her head under his chin. “Yes, very. Can we sleep like this?” Cassie chuckled as she watched Helena and Travis. She felt Taylor’s lips on her neck, and she turned to look at her. “They’re very cute,” Taylor said. “Yes, they are. Are you sure you want to do what we talked about?” Cassie said softly and pushed some hair off Taylor’s face. “Yes, I do. I want to feel what you did. Tell me what it was like,” Taylor said. Cassie thought back to how terrified she was tied up on the boat as the Jamaican man touched her and inspected her. She was sure they were going to kill her, but their touch was electric. When Cooper touched her, it was more than electric. “It’s hard to describe, I was so scared to death and then it was like they knew exactly how to touch me.” Taylor stared at her as he spoke. Cassie smiled. “You’re so cute,” Cassie said and kissed her lips gently. “I want to feel that, even the fear. I have lived in fear my whole life. It feels good to be able to have some control over it now,” Taylor said. Cassie looked at her cute friend and thought about Taylor’s father and how brutal he was and the things he said to her as he beat and tortured her. Cassie’s thoughts grew dark as she thought about what she wanted to do to him. “Taylor, you know your father is going to suffer,” Cassie said. Taylor nodded. “Yes, and I would like to be there.” “Are you sure?” “Cassie, don’t think that you’re the first one he abused. He never hit me, but the verbal abuse was relentless. The thing that hurt the most was that I felt he was not even interested in me unless I pissed him off.” Cassie sighed and mentally compared Taylor’s father to her own. Could she hold her father accountable if he really didn’t know it was her? Could she be mad at him for not recognizing his own daughter as he shoved his cock in her mouth? Even if he didn’t know it was her, he still knew it was a young girl, how did her father turn into a rapist? Was Tony that powerful to be able to change people? Cassie’s thoughts were broken by a warm kiss on her cheek. She looked at Taylor. “I’m sorry if I made you sad,” Taylor said. “No baby, it wasn’t you. There are a lot of things flying around in my head. Sometimes it’s hard to ignore them.” “Would it help to distract you if you stuck this in my butt?” Taylor said and held up the small silver dildo. Cassie laughed and hugged Taylor. “Yes, that would be a distraction. On your hands and knees bitch.” Taylor scrambled up and stuck her ass in the air, her head on the bed. Cassie grabbed the bottle of lube on the side table and rubbed it all over the dildo. She slipped a finger in Taylor’s ass and heard a little squeal. She held her finger still and rubbed Taylor’s butt. “Relax, just breathe,” Cassie said and wiggled her finger. “It feels weird,” Taylor said. “You ready?” Taylor nodded and Cassie slipped her finger out, replacing it with the slick silver dildo. She pushed it gently and it slid into Taylor’s ass. Taylor let out a breath and moaned. Cassie buried it, pushing the base firmly against Taylor’s ass. Cassie slid next to Taylor’s face. “Are you okay?” “Yes, but I think I need some kisses to take my mind off the pole in my butt.” “I have a lot of kisses for you.” Taylor slowly got up and moved against Cassie, kissing her deeply as they hugged. Cassie ran her hand down and held Taylor’s cute butt as she kissed her friend. Taylor pulled off the kiss eventually and snuggled up against Cassie. Cassie kissed her forehead and heard Taylor sigh. “That was cool,” Travis said, and Cassie turned her head to see Helena on Travis’s chest with her eyes closed. “Is she asleep?” “Yeah, I think so,” Travis said and rubbed Helena’s back. “Your cock put her to sleep?” Travis chuckled. “I guess so, that’s a first for me.” “Yeah, I remember that thing waking us up in the room at HQ a few times.” Travis frowned and Cassie smiled. “Travis, all the memories are in there, and I can’t ignore them.” “I know, I’m just sad when I think about the things I did.” “You mean like being kind to us and saving Kelcie’s life?” Travis smiled awkwardly. “So, what are you going to do now?” Cassie said and nodded towards Helena. “I guess I will go to sleep with a pretty girl on my dick.” “Are you still inside her?” Travis nodded. Cassie snickered. “She looks very comfortable.” “Yeah, I can’t complain either,” Travis said and smiled. “Good night, Travis.” “Good night, Boss.” Cassie opened her eyes as her bladder gently screamed at her. She slipped out of Taylor’s arms and walked into the bathroom, naked again. She sat on the toilet and wiped her eyes. Her tummy rumbled and she looked up at the clock. It was 12:15, right on schedule, she chuckled when she thought about the captain and their midnight snacks. She finished and walked back into the bedroom. She quietly opened a drawer and found one of Travis’s white T-shirts. She slipped it on, and it fell to the middle of her thighs. She walked over to the bed and pushed Taylor closer to Travis. He lifted his arm and put it around Taylor with his eyes closed. Taylor shifted her head onto his chest and Travis’s hand landed on her tight little butt. Cassie smiled as Helena slept on Travis’s chest with Taylor now snuggled up against his side. She slipped out of the room. Cassie walked to her special spot and leaned on the railing. The ocean was calm with the moonlight shining across the small bumps of water. She heard the splashing against the boat, slowing down her heart rate even though she was at the exact spot she jumped from. She remembered the dream that night; it was so real, and she could have sworn Becky was down there hurt. She looked down at the water and shuddered. “Couldn’t sleep?” Cassie turned to see the captain walking up. “Hey Schmitty, no, I think my body is just used to this time of night.” “Yeah, I understand,” the captain said, looking at her in the oversize shirt and her bare feet. He looked back at the open water. Cassie took a deep breath and let her mind relax, the thoughts slowed down and cleared slightly. His voice broke her trance. “It really is nice out here. Boss, any idea when you want to leave?” Cassie sighed. “I think I have one more thing we need to do before we leave.” Captain Schmidt nodded and looked out at the water. “One more Cooper visit?” “Are you clairvoyant?” Captain Schmidt chuckled. “No, I just figured. She’s special to you.” Cassie sighed again. “You know, it’s funny. I went through a lot of disgusting stuff and during it all the only person that ever said anything that resonated with me was her. Now it was in the middle of a Jamaican gangbang and a drug deal, but it stuck with me. She seems to understand me.” “Yeah, I saw it. Cooper is very different. She can be very violent and ruthless but then very compassionate and empathic a few minutes later.” Cassie stared out at the water. “I wouldn’t want to piss her off.” Captain Schmidt chuckled. “It would only be once.” Cassie looked back at the Captain. “Schmitty, why am I not afraid of her?” “I have no idea boss, maybe you have seen scarier things?” Cassie sighed and looked back at the open water. “Maybe.” They both leaned on the railing for a few more minutes, the only sound being the water against the side of the boat. The rumble of Cassie’s stomach broke the silence. Captain Schmidt chuckled. “Snack, Boss?” “Yeah, I guess so.” Captain Schmidt turned and held out his arm. “My lady?” Cassie smiled and put her hand on his arm. “Lead on my champion.” Captain Schmidt laughed and led her to the lounge. They sat on the stools and Gwen popped through the doors. “Gwen, when do you sleep?” Cassie said. “Right after this, I have always been a night owl. Comes in handy, I get a lot of prep work done the night before.” “Okay, just take care of yourself,” Cassie said. “Thank you, boss. What do you guys want tonight?” Cassie chuckled. “Gwen, you have never served anything that wasn’t heavenly. Surprise me.” Gwen looked at the captain. “I’ll have what she’s having.” Gwen nodded and disappeared through the doors. Cassie looked at the captain. “What’s her story?” Captain Schmidt exhaled slowly. “She grew up in an abusive household. My sister married an asshole after he got her pregnant in high school. He was horrible and I’m pretty sure he beat her. I tried to help as much as I could, but I was away a lot, and she wouldn’t leave him. I don’t think he ever hurt Gwen, but she saw her mom getting hurt. My sister passed away due to cancer when Gwen was 13 and that just about destroyed her. Her father fell into a drunken depression, and I scooped Gwen out of the house. She has been with me ever since until she got the job in Montana. Cassie nodded. “Did you know what was happening in Montana?” Captain Schmidt shook his head. “I never knew exactly until it all blew up. The men on the cruises were not very nice and I didn’t like the looks of the girls they brought on board.” “Dead eyes?” The captain’s eyes got big. “Yeah, exactly. The men didn’t bother me, but I was pretty sure they didn’t treat the girls very well. About halfway through high school, she started cooking on the boat. At first, she was just assisting but then I lost my cook, and she took over. She did it for a couple years until she was asked to move to Montana.” “What happened to get her from the boat to there?” Cassie said and the captain frowned. Cassie saw the sadness in the captain’s eyes. “Victor ate her food.” Cassie felt her heart stop for a second and then she took a deep breath. “Victor was on this boat?” The captain nodded and Cassie sighed. “Did he ever hurt her?” Captain Schmidt shook his head side to side. “Not that I know of. Gwen was a little naïve when she was younger, and I believe her when she says she didn’t know what was happening up there. I think Victor treasured the food and he didn’t mess with her.” “Victor was very proud of the food,” Cassie said, remembering the dinners in Victor’s office. Cassie saw the frown still on the captain’s face. Cassie touched his arm, and he looked at her. “I’m sorry boss, I just can’t get what happened to Helena out of my head. I knew that the men harassed Helena and the staff a little. I tried to intervene as much as possible.” Cassie saw his eyes get sad and she rubbed his arm. “Schmitty, she’s okay. Nathaniel was the first time she was really hurt.” “Thank you, I felt so bad when that happened. After I met you I promised her it would be different this time. I thought Nat was a little bit of a wild card, but I didn’t think he was capable of that.” “Schmitty, we are taking care of it.” Captain Schmidt smiled. “I heard, I don’t want to hear the details.” Cassie snickered. “Let’s just say he didn’t appreciate a certain thing in his mouth today.” “Oh, I am sure. Nat is very homophobic.” “Really? Now that’s interesting.” “Boss, I don’t like that look in your eyes.” “Schmitty, you don’t have to be involved at all. We will take care of him and Beatrice will escort him to jail as soon as we get back to the states.” “Thank you for that.” The doors flew open, and Gwen came through with two plates. She put them down and Cassie looked down at a very interesting sandwich. “What is it?” Cassie said. Gwen lowered her head and spoke very softly. “I hope you like it; it’s swordfish.” “Swordfish?” Cassie said and Captain Schmidt chuckled. “Boss, you said to surprise you. That’s a dangerous thing to say to this girl.” Cassie smiled and picked up the sandwich. It smelled wonderful and she took a big bite. The flavors exploded on her tongue, and she moaned and closed her eyes as she chewed slowly. She swallowed and put down the sandwich. She got off her stool and hugged Gwen. Cassie whispered in Gwen’s ear. “I love you; you are amazing.” Cassie pulled off the hug and saw tears running down Gwen’s face. Cassie wiped them off with her fingers. “You will need to get used to compliments like this, especially from Jennifer,” Cassie said, and Gwen chuckled. “Thank you, I’m so happy,” Gwen said. “Good, we make a great team, you make me very happy,” Cassie said and hugged Gwen again. Cassie broke the hug and kissed Gwen again on the forehead. “Now, you go get some sleep and let me finish this incredible sandwich.” Gwen nodded and scampered through the doors. Cassie climbed back on her stool and picked up the sandwich. She looked at the captain and he was staring at her. “What?” Cassie said. Captain Schmidt shook his head. “You are something else girl. Thank you so much for what you are doing for her; I will never be able to thank you.” “Oh, I can think of a way for you to thank me,” Cassie said and took another bite. Captain Schmidt chuckled and picked up his sandwich. “No, you’re just being silly. Now that you’re healthy you don’t need this old guy.” Cassie swallowed and smiled at him. “Schmitty, have you ever heard of sexual training or grooming?” “I’ve heard the words but not sure I completely understand.” “Well, for three months we were forced to have sex before we could eat. In fact, there was a rule that you could use any hole, but every hole had to be used at least once a week so that created Ass Friday.” Captain Schmidt lowered his head. “Schmitty, it’s okay. We are working on it, but sex and food are still all mixed up in our head. My body reacts in strange ways.” “Strange? How?” Cassie leaned back, forcing the shirt to tighten across her chest. Her nipples were painfully obvious as they stuck through the white fabric. Captain Schmidt blushed but couldn’t take his eyes off her chest. “And that’s not the only thing that reacts, my pussy is tingling with every bite.” “Boss, I’m so sorry. So, you want to have sex every time you eat?” “Yes, but it’s more like a need than a want. It also works both ways. Sometimes when I have sex, I get hungry. It’s very frustrating but we’re learning to live with it.” “We?” Cassie chuckled. “Yes, Jennifer is fighting the same battle. I would not be surprised if she needed you a few times before we get back home.” “Oh, my goodness,” Schmitty said as he remembered the adorable little girl dressed in the French maid uniform. Cassie smiled and rubbed his arm again. “You can relax, she is very sweet, and I promise you if it happens it will be a core memory for you.” Captain Schmidt shook his head again. “This is turning out to be a very interesting cruise. I guess it does help to have a lot of friends around you for that ... need.” Captain Schmidt said, and Cassie smiled. “Yes, but they are all asleep right now so you will have to be my savior tonight.” “Boss, are you sure?” Cassie leaned over and whispered. “Yes, very sure. Finish that sandwich so we can go to your cabin, and you can stuff that thick cock inside me.” “Oh God,” Captain Schmidt said, and his face turned very red. Cassie wiped out the marvelous sandwich and slipped off the stool. She held out her hand and he took it. “Lead me to your cabin, please, so you may ravish me,” Cassie said and slid her hand up his arm. Captain Schmidt led Cassie to his cabin. He closed the door and locked it and then turned around. She was climbing up on his desk and he watched her arrange herself in a sitting position with her legs hanging off the front. He noticed the white shirt barely covering her pretty thighs. Her nipples were still hard and sticking out through the material. His cock flinched; he was in turmoil. This was not right but she was so pretty and then she looked at him and licked her lips. Cassie leaned back on her hands, letting the shirt slide up her thighs to barely cover her throbbing pussy. He stepped closer and she saw the bulge in his pants. “Schmitty, would you use that magic tongue on me again?” Cassie said and spread her legs; the shirt pulled up to her waist. Captain Schmidt watched the young pussy open before his eyes. His brain felt the loss of blood as his cock stiffened. He knelt before the beautiful girl, putting his hands on her tender thighs and spreading them even farther. His mouth watered and he lowered his head. Cassie moaned as yet another tongue lapped at her pussy. She would never get tired of this; she chuckled when she thought about Taylor doing this to her all the time if she asked her. His rough hands rubbed the inside of her thighs; it brought her back to the present and his large tongue as it bathed her hot opening. Captain Schmidt had been around his share of pussy in his life, but this one was just a little bit sweeter than any he had ever tasted. It could be the girl it was attached to, but he was not questioning as he drank her juices. She was moaning and he saw her drop onto her back on his desk. He drove his tongue into her as deep as he could, and she shivered. Pulling out and licking all over her opening, he tried to capture everything her body offered. He saw the small clit situated at the top of her beautiful pussy and he moved his tongue up slowly through the tasty lips, eventually circling around the small nub. She lurched and grabbed his head. Cassie loved the way he licked and slurped all over her. Her pussy was in heaven, and he really knew what he was doing. She smiled when she thought about a competition between him, Taylor, and Marcus. That would be interesting, and she would love every minute of it. His tongue moved through her open lips and then touched her clit. A surge of pleasure rocketed through her bones; she grabbed his head, his hair too short to get a handful so she rubbed all over it as he ran his warm tongue over her most sensitive spots. Captain Schmidt felt her start to shudder and he continued his tongue lashing. She was making cute little noises and rubbing his head. He thought about all the bosses in his life and how she was officially the best one by far. He flicked his tongue over her clit repeatedly and she screamed and went perfectly stiff. He continued and her muscles released, she shook all over his desk and he held on and continued to lick. Cassie’s eyes rolled up in her head as the wonderful orgasm surged through her body. She relaxed and let him do whatever he wanted. His tongue was relentless, and she went limp under him, her body shivering every few seconds as the pleasure flowed all through her. He stopped licking and she looked at him as he lifted his head from between her legs, his face shining and smiling at her. “You okay boss?” “That’s a stupid question; I think I may be paralyzed.” Captain Schmidt stood up and looked down at the pretty girl spread out on his desk. Her shirt was gathered on her chest, her left breast out in the open. He reached down and squeezed the perfect globe, and she smiled. “You are very good at that,” Cassie said. “Thank you, my lady, it was a pleasure. Are you ready to go back to your cabin?” Cassie laughed. “Not quite yet buddy.” Cassie slid off his desk, dropping to her knees in front of him. She grabbed his pants and started to open them. “Boss, it’s okay.” “It’s more than okay if I remember right,” Cassie said and yanked his cock out of his pants. “Yes, much more than okay,” she said and sucked in the thick head. He groaned and she whipped her tongue around the head. She pulled off and licked all over the shaft, going down and flicking her tongue on his balls. He flinched and groaned, and she sucked his sack gently and then ran her tongue slowly up the shaft again. His hands were in her hair, gathering handfuls as she made love to his cock. She sucked it back in her mouth and pushed it to the back of her throat. She felt him pull her hair, but she pushed, and the cock slipped into her throat, blocking her air completely. She pushed hard into his body, driving the cock as deep as possible. Captain Schmidt let out a growl as his cock slid into her throat. He looked down and her face was smashed against his crotch. No one had ever done that to him, and he lost it. His balls contracted and blasted a huge load into her belly. She held onto him, her hands on his ass pulling him into her. He saw her throat flexing as she swallowed. His balls emptied and she pulled off slowly. His cock was sensitive, but she avoided those parts expertly. Her tongue was all over him and now she was sucking on his balls again as his soft cock sat on her head. He tried to get control, but she popped a ball into her mouth, and he groaned. She didn’t stop and now she was licking slowly up his shaft. After a few minutes his cock started to respond to her relentless technique, and she licked slowly around the head and smiled up at him. “Schmitty, time to fuck the boss.” Cassie stood up, holding his cock in her hand and climbed back on the desk. She spread her legs and held him at her opening. She looked at him, his face was red, his eyes were blazing with lust, just the way she liked. “Captain, will you shove this fat cock into me, please?” Captain Schmidt growled and powered his cock deep into the young girl, bottoming out quickly, grabbing her thighs and pulling them against his body. He felt her hands on his arms, and he looked at her. “Schmitty, stay right there for a little while.” Cassie felt him pause as his cock pulsed deep inside her, she could almost feel his heartbeat. She closed her eyes and felt the wonderful stretching as the thickness filled her so differently. She remembered being on her back on Victor’s desk so many times, his cock stuffed in exactly the same place. She recalled all the interesting conversations they had as he was inside her, how she occasionally saw his humanity through all his cruelty. She knew he was still out there, and she knew she would not truly rest until she found him. She had a lot of work to do before she was ready for that, but he was the ending. She would need her whole team for that, and she had no idea how she was going to do it. Her thoughts were broken by a voice, and she realized she was still on her back on a desk, stuffed with a thick cock. “Boss?” Cassie realized her mind had wandered. She looked up at his face, lined with worry as he held her thighs in his hands, his cock still pulsing deep within her. She reached up and ran her hands along his arms. “Sorry Schmitty, would you mind fucking me now and don’t hold back please or you’re fired.” Cassie chuckled as he growled and started to punish her pussy. She leaned back and let him fuck her hard. She felt her body sliding under his thrusts and his cock was flying in and out of her like a piston. His face was twisted with lust, and she felt a little bad for pushing him into this. He would feel bad, but she would worry about that later, right now he was fucking her like a madman, and she loved it. She closed her eyes and let him try to destroy her pussy. She smiled when she thought about all the cocks that had tried to do that, but no one could. He was hammering her, and she heard his breath racing as he fucked her viciously. She opened her eyes and saw her bare feet in the air as he pushed on her legs, getting more leverage to drill down into her. Dr. Trish was going to have a field day with this one. Captain Schmidt looked at the young girl smiling at him as he fucked her brutally. Her pussy was still tight and warm, and his cock was loving it. He worried about how hard he was hitting her, but she kept smiling. She was really a unique girl, maybe that was why everyone gathered around her. His cock was actually getting hotter with the friction as he powered into her over and over. He was lasting longer than he thought possible and then his eyes caught movement as she lifted her shirt and started to squeeze her own breasts. He focused on the stiff little pink nipples and his balls contracted. He growled and slammed into her feeling his cock shoot stream after stream deep into her small body. Cassie smiled as he finished inside and then collapsed over her. She grunted as he landed and then ran her hands over his shoulders. She felt his breathing start to slow down, and she kept holding him. She felt his mouth move on her breast and then heard his voice. “Boss, I’m so sorry.” “Schmitty, it’s okay, you were amazing, you did a great job, but you had to finish eventually.” He pulled his body up and looked down at her with a confused look on his face. She had that same pretty smile. “Schmitty, that was amazing. Thank you.” “Boss, I shouldn’t ... I’m sorry...” Cassie laughed. “Schmitty, when are you going to believe me when I say that is exactly what I wanted.” “Boss, I don’t understand.” He lowered her legs, and she held out her hands. He helped her sit up and she ran her hands over his chest. “Schmitty, as you can tell we are all a little messed up and we are working hard to get better. I’m sorry to tell you but when I tell the others about this you may have some more visitors quicker than we thought.” “Oh God no.” The captain looked terrified, and Cassie giggled. Cassie walked slowly back to the cabin, her legs a little shaky after the captain’s session. She slipped into bed behind Taylor and snuggled up against her cute rear, she ran her hand over it and felt the plug still in her butt. She chuckled and closed her eyes; sleep took her quickly. Cassie woke up as she felt the bed moving. She opened her eyes and saw Helena on her back with her legs in the air, Travis between them and fucking her slowly. She could tell they were trying to be quiet and not disturb her or Taylor. She could hear Taylor’s cute little snores as she slept on Cassie’s left breast. Cassie kept her eyes mostly closed as she watched the slow, deep fucking. Travis continued for a while and then Cassie saw him clinch his butt as he pushed against Helena, causing her legs to dangle over her head. He groaned and thrusted into her a few more times. He pulled out and Cassie saw his stuff flow out of Helena’s pussy. Travis kissed her gently and then sat up, allowing Helena to get up. Cassie saw Helena was still wearing her stockings and watched her pick up her shirt and slip it on as she stood next to the bed. “Travis, thank you, that was great,” Helena whispered and kissed Travis again. Travis watched her scamper out of the room, her cute little butt flashing him under her shirt. “That was sweet,” Cassie said softly, and Travis looked at her. “She’s a nice girl but if you keep adding them you will need to get a few more guys, I think my dick might be broken,” Travis said as he held his soft cock. Cassie giggled. “Travis, are you complaining about too much pussy? You know you could lose your man card for that.” Travis leaned his head back and laughed. “I guess you’re right, I should be counting my blessings.” “Yes, you should, and you know Kelcie will never let you rest for very long anyway.” Travis sighed. “That’s true, I’m surprised she’s not in here yet.” “The last time I saw her she had her hand wrapped around Marcus’s cock and she was fast asleep.” “That sounds interesting.” “Yes, it was, Jennifer was on one side and Kelcie on the other.” “So, Marcus will have a similar wakeup call?” “Most likely, if I had to guess it would be Jennifer on his face and Kelcie bouncing on him.” Travis laughed. “Cassie, sometimes I think I have died and gone to heaven.” “Nah, I heard all the girls in heaven are virgins, you are definitely not in heaven.” Travis laid down and started laughing. “Cassie, I love you.” Cassie sat up and saw Taylor was still sound asleep. She noticed Travis was staring at her chest, she chuckled and shook her breasts a little. His eyes opened wide, she smiled and crawled out of bed as Travis pulled Taylor next to him. Cassie saw her snuggling on his chest. “Thank you, she should be okay when she wakes up.” “I’ll believe that when I see it, every time one of you guys wake up it seems I end up fucking someone.” Cassie stood next to the bed and held out her hand. Travis looked at it and then at her face. “Man card, hand it over.” Travis laughed hard and Cassie started laughing with him. “You’re right, counting my blessings,” Travis said and squeezed Taylor’s cute ass. Cassie nodded and walked out of his room. She closed the door and looked up to see two men walking towards her. She looked down and saw she was naked again, fuck. The men froze when they saw her, and she saw them take off their hats and hold them in front of them. They looked terrified. She looked at them and they lowered their eyes. “Boss, sorry, we didn’t know ... we can ... would you need...” Cassie saw the man look up at her as he stumbled with his words. He was now looking at her face and she could tell he was struggling as she stood naked in front of him. “Gabriel, right?” Cassie said and he nodded. “Thank you, Gabriel, for staying with the girls the other night.” Gabriel smiled. “Not a problem, I was happy to help. How is Miss Helena?” “She’s doing much better, thank you for asking.” “That’s good, I am happy to hear that,” Gabriel said. Cassie looked at the other man. He was still looking down at his feet. She reached out and touched his arm. He flinched and his eyes shot to her face. “What’s your name?” “Mario ... I’m sorry ... I didn’t mean to stare.” Cassie snickered as she saw his eyes flicker down quickly and then back up to her face. “Nice to meet you Mario, it’s ok to look, I don’t mind.” Cassie saw his shoulders relax and then his eyes moved to her chest and then back to her face. “Looking is not the issue, what happened to Helena was much more than looking,” Cassie said, and Mario nodded. “We are so very sorry for that, Nat surprised us as well,” Mario said. “I’m glad to hear that. I know Beatrice put the fear of God into you guys, but you can just treat us like regular girls.” Mario looked back at her breasts and then back to her face. “Um, boss, this is not ... regular.” Cassie chuckled. “So, the girls on the other cruises didn’t run around naked?” “No ma’am, they were naked sometimes around the pool, but the men were always there and the girls never...” “They never talked to you?” “No ma’am, they were always sort of ... lost.” Cassie frowned. “I understand. Would you like me to ask the girls to not run around naked?” Mario’s eyes got wide. “No ma’am ... I mean...” Cassie smiled. “How about we continue as we are, and you relax around us? Also, not do what Nathaniel did.” Mario and Gabriel shook their heads. “No ma’am, never,” they said in unison. “Thank you, can you share it with the other guys? How many are you?” “Yes, boss. We will let them know. There are five of us left. Mario, myself, Terry, Gerald, and Juan,” Gabriel said. “Thank you, Gabriel, nice to meet you, Mario. You guys have a nice day,” Cassie said and walked past them. Cassie reached her door and turned to see the two men looking at her. They nodded and left down the hallway. She did tell them that looking was okay. Marcus heard the door and looked to see his shorty walking up, her perfect breasts moving slightly on her chest. His cock flinched again. “Good morning,” Cassie said. “Good morning, shorty” Cassie saw Jennnifer shift her head and let out a small sigh, her eyes still closed. Kelcie was out like a light. Marcus had his hands on both of their butts as he held them. “Hands full, I see.” “Yeah, they were really tired, I don’t think they moved other than taking their hands off my dick.” Cassie chuckled. “I’m going to take a shower, let them sleep.” Marcus frowned. Cassie stopped at the door and looked back. “It’s okay, you will get the breakfast duty,” Cassie said and disappeared into the bathroom. Marcus sighed, closed his eyes, and squeezed two perfect little butts. Taylor opened her eyes and saw black skin. She sat up slowly and saw Travis looking at her. “Good morning, sunshine,” Travis said. “Good morning, where’s Cassie?” Taylor said, wiping her eyes. “She went back to her room to take a shower and wake up Marcus, I figure.” Taylor nodded and stretched. Travis couldn’t help noticing her body and his cock flinched. “Taylor, what’s with the plug?” Taylor looked at him. “Um, well, I’m in training.” “Training for what?” “Well, I guess a lot of butt fucking.” Travis sat up and looked at the young teenager. “Okay, what the hell is going on?” Taylor flopped down on the bed. He was staring down at her, and he looked worried. “Travis, it’s hard to explain.” “Try me, I spent two years in a pornography and sex trafficking operation.” Taylor sighed. “I just want to experience some of the things she did.” “Why? What she went through was horrible.” “Not everything, the thing with the Jamaicans didn’t look horrible.” Travis shifted and sat her up against the headboard. “Taylor, what are you talking about?” Taylor sighed again. “I know it sounds bad, but she admitted it was nice, and she wouldn’t mind doing it again.” “Doing what again?” “The thing with all of Cooper’s men.” Travis looked at the young girl. “Are you telling me you are training for a gangrape?” “When you say it like that it sounds bad.” “Taylor, it is bad. Cassie and Jennifer were raped for three months by numerous guys, none of that was good.” Taylor sniffled and Travis saw a tear run down her cheek. He pulled her into his arms as she started crying. He rubbed her back and kissed her head. “Travis, I just want to feel what she’s feeling.” “I understand but baby can you pick something else a little less severe.” “She said it was amazing; I saw her eyes when she was on Cooper’s lap and then when she asked her if she wanted to spend time with her men again.” Travis took a breath and held the small girl. He really didn’t understand this at all. He was vaguely aware of Taylor’s obsession with Cassie, but this was nuts. He looked down at the girl and she looked up at him with sad eyes. “Travis, would you help me?” “Help you with what baby?” “The butt stuff, I know you don’t understand but I really want to do this, and Cassie said I needed to prepare.” Travis sighed. “Taylor, I don’t know if I’m okay with training you for anal sex.” Taylor lowered her head and then reached over to the nightstand. She grabbed a gold plug and looked at Travis. “Will you at least help me change out this?” Taylor said and pouted. Travis took a deep breath and took the plug from her. It was about 5 inches long and relatively thick with a wide base. He looked back at the young girl. “You don’t have to do anything else, just pull out the one that’s there and put that one in.” “Taylor, you are insane.” Taylor snickered and jumped onto her knees. She leaned forward and stuck her ass in the air. Travis saw the S carved into the smooth skin of her left cheek and he frowned. She wiggled her hips, and he put his fingers on the base of the plug in her butt. He pulled it out slowly and she moaned. He saw her ass slowly close, and he remembered all the young girls that he shoved his cock into. Sadness rolled over him again and he took a deep breath. “Travis?” Travis looked at her and she was holding out the bottle of lube. He took it and coated the bigger plug. He placed it against her asshole. “Don’t hold your breath, just breathe deep and slow and try to relax.” “Okay.” Taylor took a slow deep breath and felt her butt opening. Travis pushed slowly and let her get used to the width. He had never been this close and now he knew what his cock looked like going into a young teenage asshole. He stopped and took another breath. Taylor groaned as her ass stretched and then she felt the thing slip in and the base hit her ass. It felt so strange, like something way too big was where it wasn’t supposed to be. She started to question her decision, could she take on a bunch of men with larger cocks than this? Could she take them in her butt if they wanted to go there? From Cassie’s explanation she knew there would be double penetration, she had never done that. She would have to figure out how to train for that too. She felt Travis touch her butt and rub it gently. “Are you okay?” “Yes, your hand feels nice, you can keep doing that.” “You know you will not get gentle stuff like this in a gangbang. You’re going to feel like a piece of meat, like you’re nothing to the men but a place to stick their dicks.” Taylor sat up and turned to look at him. She touched his cheek and saw the sadness in his eyes. “Travis, you are a wonderful man, and I promise eventually we will be normal friends, maybe with benefits but it won’t be weird.” “That sounds nice.” Taylor smiled. “However, I have some issues that my father, mother, and brother carved into me over the years. I am trying to come to terms with the fact that people might think I’m worth loving. I wasn’t for a long time.” “Taylor, you are...” Travis started, and she put her fingers over his lips. “Let me finish.” Travis nodded and put his hand on her hip, rubbing the soft skin. “I was a psycho bitch for a long time. I had to be to survive at my school and in my house. I never knew I could be anything else until she walked into my house.” “I get that,” Travis said and nodded. “When I realized who and what she was I wanted to be her friend desperately. My father was furious and increased his cruelty towards her because of it. He wanted to show me that she was nothing, just a whore that was not worthy of us. He tried but he couldn’t do it. Cassie fought him the whole time, it brought on more abuse for her, but she never backed down from him.” Travis sat stunned as he listened to the girl’s story. He knew Cassie was special but now he was getting more evidence. She stood up to a senior member, and a cruel one at that. He had seen Jameson a few times and knew he was an evil fuck. Taylor rubbed his cheek, and he focused back on her. “Travis, he hurt her badly and he made me watch. I watched her and her strength, and I wondered if I would be able to do that if I was ever in that position. Eventually I was when Stratford raped me and then gave me to a dog before he branded me.” “Taylor, I’m so sorry.” Taylor smiled. “It’s okay, I’m not telling you this to get sympathy. What happened was that I figured out I was strong too. I started standing up to my father and reaching out for more time with Cassie. When she disappeared, I was heartbroken. I figured she was gone, and I had lost my one true friend. I had just about given up and then Beatrice walked into my house and arrested my father.” Travis tried to talk but he didn’t have any idea what to say so he closed his mouth. Taylor snickered and scooted closer to him, kissing him lightly on the lips. “What happened next?” Travis said. “Well, my mother never came home, and they took my brother to a juvenile home. I knew I was going into foster care, and I was ready for that. I figured it couldn’t be any worse than where I was living. Beatrice took me to an apartment and Helen opened the door. I had no idea that was going to happen, but B set it all up ahead of time and she was my foster mother.” Travis felt his throat get tight and then a tear came out of his eye. Taylor smiled and wiped it off his cheek. “So, you see Travis, I love her, and I worship her, she saved me. I will never be able to pay her back but as long as she lets me hang around, I will do whatever she needs me to do.” Travis nodded and continued to try not to start outright sobbing. He pulled the girl into a hug. He felt her breath on his chest. “So do you understand why I want to experience anything that she loved. Anything that could make me more like her. You saw her with Cooper. I think I will be safe with them.” Travis took a deep breath. “I understand. I only have two questions.” “Okay, shoot.” “Would you be okay if I went with you when that happened. I’m sure Beatrice will not let you go without her if you tell her, and I would advise you to tell her.” “Travis, do you want to be my champion?” Taylor said and looked at his face. “Yes, if that would be okay with you.” Taylor smiled and kissed him gently on the lips. “I would be very much okay with that.” Travis pulled her into a kiss and wrapped his arms around the young girl. She broke the kiss after a little while. “What was your second question?” Taylor said and rubbed his cheek. “When would you like me to fuck you in the ass?” Taylor started laughing and fell into Travis’s chest. He joined her and they laughed for a while.