Chapter 2: Chapter 2
Jena awoke in the morning getting ready for the next task Jason had given her last night . She took a deep breath and stood in front of the mirror, staring at her reflection. Her body was tense with anticipation and a hint of fear. She had never done anything like this before, but she had promised Jason that she would obey him, and she was determined to follow through.
She slipped off the robe she had slept in, revealing her naked body, the small cock still locked securely in the cage. She couldn't help but feel a sense of vulnerability and shame at the sight of her locked cock, but she knew that this was part of the journey she had chosen to undertake.
She took a shower, trying to relax her body and clear her mind. Soon she would be sucking a horse size dildo then it would be fucking her ass . She wondered how she would take it, but she was determined to try. After all, she had promised Jason that she would obey him, and she was not one to break her promises.
As she stepped out of the shower, she toweled herself dry and looked around the room for something to wear. She remembered Jason's instructions to wear something comfortable for dinner and decided to put on the same silk robe she had worn the night before. It was soft and smooth against her skin, and she felt a sense of comfort and security in it.
She checked her reflection in the mirror one last time before heading out the door.
She leaves her room walking through the living room and look at Jason through the dungeon door setting up the horse size cock to it.
She dreads what's to come, she's never been with someone so large, but she promises herself she'll give it her best shot. She takes a deep breath and knocks on the door,
"Jena, I see you're ready," Jason says, his voice stern yet filled with anticipation.
"Yes, sir," Jena replies, her voice barely a whisper. She steps into the dungeon, the air filling with a mix of fear and excitement.
Jason gestures to the horse-sized dildo now attached to the fuck machine. "This will be your first task for the day. Your going to suck it till you can take the entire length into your mouth and throat," he says handing her a switch "This switch has been programmed with your safe word press it if it gets to much," he says , his voice commanding yet steady.
Jena's eyes widen as she looks at the massive dildo, a shiver of fear and excitement running down her spine. She takes a deep breath, trying to calm her nerves. "Yes, sir," she whispers, taking the switch from Jason's hand. She walks towards the dildo, her heart pounding in her chest.
Jason watches her, a smirk playing on his lips as he sees the mixture of fear and determination in her eyes. He knows that she's going to try her best, and he appreciates her willingness to push her boundaries.
"Now get into position on the your knees and start slowly," he says , his voice firm but not unkind.
Jena takes a deep breath, her heart pounding in her chest as she gets down on her knees in front of the monstrous dildo. She reaches out tentatively, her hand wrapping around the base of the dildo, feeling the cool, hard material against her skin. She takes a deep breath and slowly leans forward, her lips parting as she takes the tip of the dildo into her mouth.
The taste is faintly rubbery, and the sensation of the smooth, hard material against her tongue sends a shiver down her spine. She tries to relax her jaw, willing herself to take more of the dildo into her mouth.
She can feel her lips stretching around the massive girth, and she knows that she has a long way to go before she can take the entire length into her throat.
Jason watches her intently, his eyes never leaving her face. "That's it, Jena. Take it slow. You're doing great."
Jena nods, her eyes watering slightly as she takes more of the dildo into her mouth. She can feel her throat constricting around the thick shaft, and she has to fight the instinct to gag. She takes another deep breath, trying to calm herself as she pushes herself furthe
"I'm going to turn the machine on it will start thrusting into your mouth now," Jason says, his voice firm yet encouraging.
Jena nods, her eyes locked on the massive dildo as she braces herself for the impending invasion.
The machine whirs to life, and the dildo begins to move, slowly at first, then picking up speed. Jena gasps as the dildo slams into the back of her throat, her body convulsing as she chokes and sputters.
"Use your safe word if you need to, Jena," Jason reminds her, his voice steady.
Jena takes a moment to catch her breath, her eyes watering as she looks up at Jason.
She can feel her throat raw and burning from the rough treatment, but she knows that she can't give up. She takes a deep breath, steeling herself for whatever is to come next.
"Good girl," Jason praises, his voice filled with approval. "You're doing so well, Jena. I'm proud of you."
He reaches down, brushing a strand of hair away from her face. Jena leans into his touch, her eyes locked on his. She can see the desire and satisfaction in his gaze, and it fills her with a sense of pride and accomplishment.
"Good six inches in already, 8 more to go," Jason says, his voice gruff with lust. "You can take it, Jena. I know you can."
Jena nods, determined to prove him right. She takes another deep breath and opens her throat, allowing the dildo to slide deeper. She can feel every inch of it, stretching her wider than she ever thought possible.
The machine continues to thrust, each stroke pushing the dildo further into her mouth and throat. Jena's eyes water, feeling as the monster dildo stretches her throat almost to its limits. She can feel the cool, hard material against the back of her throat, and it makes her gag. Take it all," Jason encourages, his voice tinged with excitement. "You're doing so well."
Jena focuses on her breathing, trying to relax her body and take the dildo deeper. She can feel the pressure building in her chest, her body telling her to stop, but her mind is determined to push through.
The dildo reaches the back of her throat, and Jena can feel the tip pressed against her esophagus.
She gags again, tears streaming down her face as she struggles to breathe. The machine continues to thrust, keeping the dildo in place.
"Good girl," Jason praises, his voice thick with desire. "You're doing so well. Just a little longer, and you'll have taken the whole thing."
Jena focuses on the sensation, trying to ignore the discomfort. She can feel the dildo pulsing in her throat, the vibrations sending shivers down her spine. She takes another deep breath, determined to see this through.
Suddenly, the machine starts going faster biking harder into her throat and mouth causing her throw up all over the dildo and her breasts due to the immense pressure.
Yet she does not press the button . She decides to endure this, she wants to please Jason more than anything else.
Jason watches her with a mix of awe and lust, her determination and resilience turning him on even more. He knows that she's pushing herself to her limits, and he admires her for it. He can see the tears streaming down her face, the snot dripping from her nose, and the vomit covering her body, but he also sees the fire in her eyes.
"Good girl, Jena," he praises, his voice gruff with emotion. "You're doing incredibly well. Four more inches to go," Jason says, his voice hoarse with desire. "Just a little longer, and you'll have taken the whole fucking thing."
Jena's eyes are blurry with tears, her throat feels like it's on fire, and her body is shaking with exertion. But she can see the pride and approval in Jason's eyes, and that spurs her on. She takes a deep breath, her nose wrinkling as she inhales the scent of her own vomit, and pushes herself to take more of the dildo into her throat.
The machine keeps thrusting, mercilessly pounding into her, and Jena feels like her body is being torn apart. But she doesn't press the switch. She wants to prove to Jason that she can do this, that she can take everything he gives her.
Jason watches her, his breath coming in ragged gasps, his cock aching with need. He's never seen anyone push themselves this far, this fast. He knows he should stop her, knows that she's reached her limit, but he can't bring himself to. He wants to see how far she'll go, what she's truly capable of.
He can see the pain in her eyes, the tears streaming down her face, and the vomit covering her body. But he also sees the determination, the fire that burns within her. He knows that she wants this, wants to prove herself to him. Take it all. You can do this," Jason encourages, his voice thick with lust and admiration.
Jena takes another deep breath, steeling herself for the final push. She can feel the dildo pressing against the back of her throat, stretching her wider than she ever thought possible.
Suddenly it happens she feels the base of the dildo on her chin and she gagged violently as the entire length of the dildo slides into her mouth and throat. She's not expecting it so it catches her off guard. She chokes and sputters, her eyes watering even more as she struggles to breathe. She feels like she's being suffocated, like the dildo is going to rip her apart. But she doesn't press the button. She wants to please Jason more than anything else.
Jason watches her, his breath coming in short gasps, his cock aching with need.
He can see the sheer determination in her eyes, the fire that burns within her, and he knows that she wants this just as much as he does. He can see that she's pushing herself to her absolute limits, and he's incredibly turned on by it. You're doing so well," he praises, his voice thick with lust. "You've taken the entire fucking thing. You've done it."
Jena tries to catch her breath, her body convulsing as she chokes and sputters. The dildo is buried deep in her throat, and she can feel every inch of it pressing against her insides. "Good you may take the dildo out of your mouth now," Jason instructs.
Jena pulls back, the dildo sliding out of her throat with a wet, sucking sound. She coughs and gasps for breath, her throat raw and burning. She leans forward, her hands braced on the floor, and vomits again, her body wracked with spasms.
Jason watches her, his cock aching with need. He's never seen anything so fucking hot in his life. He walks over to her and crouches down, his hand rubbing soothing circles on her back. "It's okay, Jena. You did so well. Just breathe, that's it.
You're doing great," Jason soothes, his voice low and comforting. He continues to rub her back, helping her through the aftershocks of her ordeal. He can see the sheer determination and willpower in Jena's eyes, and it fills him with a sense of pride and admiration. She's pushed herself to her limits and beyond, all for him. He knows that she's truly special, and he can't wait to see what else she's capable of.
After what feels like an eternity, Jena's breathing finally starts to even out, and her body begins to calm down. She leans back, her eyes meeting Jason's.
"Now I want you to turn around, your going to take the dildo in your ass now," Jason instructs, his voice firm.
Jena nods, her body aching, but her mind determined to please Jason. She turns around, her knees shaking slightly as she presents her ass to him. She can feel the cool air against her wet, stretched throat, and her ass feels exposed and vulnerable.
Jason walks over to her, his footsteps echoing in the otherwise silent room. He runs his hand over her ass, squeezing it gently. "You have a beautiful ass, Jena," he comments, his voice low and husky.
"It's going to take this dildo perfectly."
Jena flinches slightly at his touch, but she doesn't move away. She knows what's coming and she's determined to take it like a good girl.
"I want you to relax your muscles, Jena," Jason instructs, his voice soothing yet firm. "This is going to hurt at first, but then it will feel good. Trust me."
Jena takes a deep breath, trying to relax her body as much as she can. She's never had anything this big in her ass before, and the thought of it sends a shiver of both fear and excitement down her spine.
"Yes, sir," she manages to whisper, her voice barely above a tremble.
Jason applies a generous amount of lube to the dildo, making sure every inch of it is coated. He then begins to rub the lube onto Jena's ass, his touch gentle yet firm. He starts with her puckered hole, slowly working the lube in, feeling her tense and then relax under his touch. He moves his hand up and down, making sure her entire ass is well lubed.
"Relax, Jena," he says softly, his voice soothing. "I'm going to push the head of the dildo in first then I will turn the machine on," he explains.
Jena nods, her body tense but trying to relax. She feels the head of the dildo press against her, and she takes a deep breath, trying to push out as Jason instructs. She feels the initial burn as the tip of the dildo breaches her, and she lets out a hiss of pain. Breathe through it," Jason encourages, his hand resting on the small of her back.
Jena focuses on her breathing, trying to relax her muscles and take the intrusion.
She can feel the stretch as the tip of the dildo opens her up, and she winces at the sting. Jason's hand on her back is a comforting presence, and his words of encouragement help her to relax a little more. Just breathe through the pain. You're doing great," Jason says, his voice soothing.
He pushes the dildo in a little further, the head of it now fully inside her. Jena feels a mix of pain and pleasure, her body adjusting to the invasion. She lets out a soft moan, the sound muffled by the vomit on her face.
She then heard the machine start to whirr to life just as Jason said "hold on to that switch Jena, just press it if it gets too much"
Jena nodded, her fingers gripping the switch as the machine started to move. The dildo began to slide in and out of her ass, inch by agonizing inch. She could feel every ridge and vein as it pushed deeper, stretching her beyond anything she had ever experienced.
Jason was watching her intently, his eyes never leaving her body. He could see the pain and pleasure mixing in her expression, and it turned him on even more.
He walked over to her, his cock rock hard in his pants.
He wanted to fuck her so bad, but he knew she needed a break first. He rubbed her reddened skin, feeling the heat radiating off of her. He leaned down and whispered in her ear, "You're doing so good, Jena. I'm so proud of you."
Jena moaned softly, her body trembling with exhaustion and pain. She felt like she had been put through a meat grinder, but she also felt a sense of accomplishment.
"You got the first four inches in, most everyone I have been with brea here," he says looking down at her as he rubs his hand along her back.
She was trying to catch her breath and relax her muscles, but she could feel the massive dildo pulsating in her ass, the vibrations sending shivers down her spine. "You've done so well, Jena. I'm incredibly proud of you."
He leaned down, his nose brushing against her hair, inhaling her scent. "You smell so good, Jena," he murmurs, his voice husky with lust.
Jena felt a shiver of pleasure run through her at his words.
Despite the pain and exhaustion, she felt a sense of pride and accomplishment. She knew that she was pushing her limits, but she also knew that Jason was with her every step of the way.
"Thank you, sir," she whispered, her voice hoarse from the exertion.
Jason kept rubbing her back, his touch soothing and comforting. But I think that's enough for now. You need to rest before we continue."
Jena nodded, relief flooding through her. She had no idea how much more she could take, but she knew that she didn't want to let Jason down.
"No sir, let me take, let me prove I can take this cock all the way," she says waiting to move forward.
Jason pauses, his eyes narrowing as he looks down at her. She's already taken more than any of his previous subs, but he can see the determination in her eyes. "Alright, Jena. But remember your safe word. If it gets too much, don't hesitate to use it."
Jena nods, her body tense but ready. "Yes, sir."
Jason turns the machine on, the dildo beginning to move again. It starts slow, giving Jena time to adjust. She takes a deep breath, trying to relax her muscles and take the intrusion.
She can feel the dildo pushing deeper, inch by agonizing inch. The pleasure begins to mix with the pain, creating a strange, intense sensation that she's never experienced before.
The machine gains speed, and Jena grunts with each thrust, her body tensing and relaxing in time with the movement. Sweat begins to bead on her brow, and her breath comes in ragged gasps. She can feel the vibrations of the dildo resonating through her body, sending waves of pleasure and pain coursing through her veins.
The sensation is overwhelming, unlike anything she has ever experienced. She tries to focus on her breathing, inhaling deeply and exhaling slowly, trying to ride out the intense waves of sensation.
"You're doing amazing, Jena," Jason praises, his voice thick with desire. "You're taking it like a champion."
Jena focuses on the words of encouragement, pushing herself to take more of the dildo. She can feel her body stretching to accommodate the massive invader, and she revels in the feeling of accomplishment that comes with each inch that disappears inside her.
She's never experienced anything like this before, and the intensity of the sensation is both terrifying and exhilarating.
"That's it, Jena," Jason encourages, his voice like velvet. "Just a little more, and you'll have taken the whole thing."
Jena grunts, her body tensing as the dildo slams against her prostate. She lets out a low moan, a mix of pain and pleasure, and her body convulses around the invading object. She can feel her orgasm building, the pleasure coiling in her belly like a snake ready to strike.
She's never felt anything like this before, the combination of pain and pleasure is overwhelming and intoxicating.
"Just a little more, Jena," Jason encourages, his voice hoarse with desire. "You can take it.
Jena nods, her body pushing back against the dildo, wanting to take more, needing to feel more. She can feel the dildo hitting her prostate with every thrust, sending waves of pleasure coursing through her body.
"That's it, Jena," Jason praises. "You're taking it all.
You're fucking incredible," Jason gasps, his voice thick with raw desire. He can see the determination and sheer grit in Jena's eyes, and it sends a surge of pride through him.
The machine is now pounding into Jena's ass at a relentless pace, the dildo disappearing completely into her with each thrust. Jena's body is taut, her muscles trembling as she takes the forceful invasion. She's grunting and moaning with each thrust, her body a symphony of pleasure and pain.
She moans as she her cock cums as the dildo rams into her ass.
The dildo hits her prostate with every thrust, sending shockwaves of pleasure throughout her body. Her orgasm starts to build, and she feels like she's about to explode.
"That's it, baby. You're doing amazing." Jason praises, his voice thick with desire. "Let go, give into the pleasure."
Jena bites her lip, trying to hold back her orgasm, wanting to drag out the sensation for as long as possible. But Jason has other plans.
He turns the machine up to the highest setting . The dildo starts to pound into Jena with merciless force. Jena screams, her body convulsing as the massive dildo fucks her ass with no mercy. The pleasure and pain mix together, creating a sensation that is unlike anything she has ever felt before.
She cums again as the machine fucks her ass , her body shaking and convulsing with the force of her orgasm.
"Fuck, Jena," Jason pants, his own cock aching with need as he watches her. "You look so good right now."
He can see the tears streaming down her face, the snot dripping from her nose, and the vomit covering her body, but he can also see the sheer determination and willpower in her eyes.
As her organism ends she feels the machine slow and sto and hears a loud pop athe didonis pulled from her ass.
Jena collapses onto her knees gasping for breath and fighting back tears of pain and relief. She feels the cool air hit her ass and it's sore and raw.
Jason walks over to her and bends down to help her up. "It's alright, baby. You did amazing," he whispers in her ear, his voice gentle and soothing. He wraps his arms around her, holding her close as she trembles in his embrace.
Jena leans into him, her body wracked with sobs. She's never experienced anything like that before, the pain, the pleasure, the intensity.
"No one ever has taken that entire thing dear, you might be the first to be able to take my cock for real, but first I think you earned a reward and rest. Tomorrow I will take you to see that doctor I told you about," he murmurs.
Jena is still shaking and sobbing in Jason's arms, her body aching and raw. She feels a sense of accomplishment despite the pain.
"Thank you, sir. I'm... I'm honored," she manages to say between sobs.
"Come on, let's get you cleaned up and into bed," Jason says, helping her to her feet.
He guides her to the bathroom, turning on the shower and helping her inside. He washes her gently, taking care to clean every inch of her sore and abused body.