After a minute of struggling, Lauren gave up. Sam walked back into the room. In one hand he held a dark and long cucumber. It was sixteen inches long and at least two and a half inches thick. In the other hand he held a bottle of raspberry flavored personal lubricant. With him he also had a large, cube-like cushion that he dropped on the floor. Lauren's face was motionless in an expression of anguish. "Please, Sam!" she cried out. Tears started to form in her eyes causing her eyeliner to blur.
Sam sat down on the bed next to her. "Just relax, Lauren," he said sweetly. "You have no idea how much pleasure this is going to give you. Just lay back and don't struggle, okay hon?" He bent over and kissed her softly on her forehead.
Lauren let her head drop down back onto the pillow. Maybe Sam was right, maybe she would enjoy it. She couldn't stop the tears streaming from her eyes. They ran down her face and onto the pillow.
"Oh, honey," Sam said, kissing her again. "You know I really care about you." He used his thumb to dry away her tears. "Okay sweetie, I need you to turn around, okay? You know what's cool about these handcuffs? There's a rotateable hinge in between both cuffs so you can turn around the 'captive'" – he said this with a laugh – "at any time. I need you to turn around and lie on your stomach."
Lauren did so. In a way, she realized that she was giving into him again and she had no idea what he'd do to her, but she couldn't help going along with him. "What are you going to do to me?" she asked.
"You'll see," he said. "Arch your back so your butt is popped out into the air." Lauren complied and Sam placed the cube cushion under her stomach. "There. Now you can place all your weight on the cushion and not feel uncomfortable." He spanked her ass playfully.
"Why do you need the cucumber and the lube, then?"
She feared that she already knew the answer, but Sam didn't reply. He opened the bottle of lube and squirted some on her small, tight asshole. Sam started massaging the orifice with the lube and before Lauren knew it he had two and eventually three fingers deep in her pooper.
"Sam..." Lauren whimpered. She was finding it hard to talk due to the new feeling of something going up her ass. She was a complete anal virgin, and his warm slippery fingers felt strange sliding up her anus. "Sam... I don't think I can have anal sex." No response. "Sam, please don't anal me. Sam!"
"I'm not going to stick my cock up your ass, Lauren."
The sick feeling Lauren had felt on the toilet hit her again like a tidal wave. "The cucumber... Oh my god, Sam! It's too big! You can't do this to me, you'll kill me!"
Sam took his fingers out of her butt and cleaned his lubed-up fingers by smearing them on her butt cheeks. He spanked her again, this time more roughly. She let out a little yelp. "You'll love it. Trust me." He picked up the cucumber and covered it with more lube out of the bottle. Once he was satisfied it was slick enough he opened her little winker again with his fingers and placed the tip of the cucumber inside her constricted hole. "Don't resist and you'll be fine, Lauren."
"Ahhhhh!" Lauren burst out, clenching her teeth.
"The more you resist, the more uncomfortable it'll feel and the more it'll hurt." Sam continued pushing the cucumber up her anus. Slowly but surely, her sphincter muscles relaxed and accepted the new intrusion against her will. Sam poured more lubricant all over her ass, on the cucumber and in her asshole. Lauren moaned, screamed and cried out, trying to resist the cucumber. She hated the full feeling it gave her and the thing she hated most was that it felt good. "I know it feels good in a weird way, Lauren," Sam said. "Just don't resist it and you'll be fine," he repeated. After a minute eight inches of the vegetable were well in her anus and in her rectum. He pushed on the cucumber a final few times and managed to get it in a full ten inches. Six inches of the rod still jutted out of her extraordinarily dilated hole.
"No, no, no, no!" Lauren cried out as more tears began emerging from her eyes.
"It'll hurt a bit, Lauren, but I know it's starting to feel normal up there and I know it'll be the best thing you've ever felt in your life when you cum." He started stroking his cock to get it fully hard. "This is cool, feel this," he said. He wound up his hand and spanked her ass brutally.
"Ahhhhh!" Lauren screamed out again. He butt clenched itself in defense and the whole vegetable moved up and down her anus with each clench. "Ohh..." Lauren moaned. This was the thing that hurt most. She was being abused and humiliated by this man she felt so attracted to, and the worst thing was that he was right: it felt so good.
"I was right, wasn't I?" Sam smiled. "It does feel good to have ten inches of that thing right up your little pooper." He removed the cube cushion and held up her waist, supporting her with his hands. "I'm going to slide under you now, Lauren, and you're going to place all of your weight on my body. I don't want you to fight me, okay?" She didn't respond. "Any brash moves and that cucumber will start to hurt you. I can tell it's your first time because of the tightness. Get ready, sweetie."
Sam slowly spread her legs and eased himself under her so they were face to face. He helped Lauren ease herself down onto him. Then he reached under her, grabbed his steel hard penis, aimed the head at her vulva and pushed in with one stroke. Lauren moaned and said his name repeatedly as he slowly started fucking her vagina. With every stroke in and out the cucumber would move as well. Her ass clenched tightly onto it and never let it go. She was full and it felt good.
"Sam..." Lauren moaned. He paused to kiss her passionately. She had fallen for him again. He had done some terrible things to her, and still she'd broken again. She knew she needed to cum to feel better again.
Sam continued to buck his hips and slide deeper and deeper into his babysitter. He wrapped his arms around her ass and grasped the end of the cucumber. With every pump he'd move the cucumber around her anus: pulling it out slightly, twisting it or pushing it even deeper in. With every movement of the monolithic vegetable Lauren would yelp out and raise her head in agony, and with every yelp of hers Sam would pump more brutally, harder, faster, unrelenting. Sam could feel the massive cucumber rubbing against his cock on the other side of her pussy. He knew she was getting closer and closer to orgasm, as he was himself.
He grabbed the cucumber and started to stroke it in and out of her butt, timing it so it alternated with his own penetrations. Lauren screamed out in anguish as the vegetable moved six inches out of her ass then pushed back in, just in time before her muscles tightened up again. "Aaahhhhh!" she yelled, before she started panting again: "Aah, aah, aah, aah, ugh, ugh, ugh, ugh!"
Within a minute she achieved her fourth orgasm of the night. She arched her back and convulsed heavily on Sam's cock. She felt the cucumber proceeding further into her bowels as her whole body shook. It was the strongest orgasm she had in her life. Pussy juice squirted out all over Sam's pole. Suddenly he found himself slipping around recklessly inside her small, shaking body. After two minutes of utter bliss and palpitations, Lauren collapsed on Sam. She had temporarily lost consciousness from the strong high. On the verge of orgasm himself, Sam withdrew from her and slid away from under her body, laying it softly on the bed. He carefully withdrew the cucumber from her anus and dropped it on the floor.
He flipped her around so her back was on the bed and kneeled above her stomach. Sam pinched her nipple strongly for a second, then relinquished his grip and slapped her breast. A red mark appeared as Lauren winced but didn't open her eyes. He did it again, yanking strongly on her rock-hard nipple and slapping the C-cup jug. After a third time, with a raw red color enveloping her tit, Lauren awoke. She looked at Sam with a twisted expression on her face.
"Hey," Sam said. He stroked his still hard cock twice and started ejaculating instantly. He blew his cum all over her face. She closed her eyes to avoid the milk spray. After three shots, he grabbed her head and pulled it closer to his penis. He drew her long hair together and fired what was left of his sticky cream straight into her blonde hair. When he'd blow the last of his load he wiped the semen on her face off with her hair.
Lauren's hair was a mess. It had been roughed up, and most of it was covered in Sam's sperm. The sperm had already started to dry and clot to the strands. She was still groggy after the rape fuck and the strong orgasm she'd just had. She felt sick and used up.
