Sissy Jen Gets Stretched

The buzzing of the alarm clock ripped Jen from her sweet dreams and dropped her into the nightmare that is her life. Her penis, or clitty as her mistress had renamed it, hurts as it threatens in vain to bust free from its permanent prison. She hated waking up in this room especially, there was no way to look at the strange surroundings and not be reminded of what she had lost. She had wanted to be humiliated, that was all, but her cruel girlfriend had transformed her from Jeff to Jen. In a quick series of events she had made Jeff get rid of his manly clothes, accept that he is a cuckold, begin to service her lover, and worst of all lose her to the superior man whose house they now both lived in and for who Jen was a live in maid and fuckdoll.

She rose and put on her maid uniform and headed off to the kitchen. Turning the corner into the hall she caught a glimpse of herself in the mirror. In the early morning light she barely recognized the slutty woman she saw reflected back. Her hair was long and she barely noticed the weight of the fake breasts she now wore for the entirety of everyday, her makeup was slutty and inviting and, much to her dismay, it invited all the wrong sort of attention. Was it that long ago that Tammy was hers and pretended to enjoy her tiny clitty? How far back did she have to go before she knew the taste of cock or the feel of it stretching her asshole? When had she last felt a pussy on her clitty? What did that even feel like? She pondered these things in misery as she made breakfast for the man of the house.

Tammy had left Jen with a simple task, keep the Master happy. No matter what he wanted or needed Jen was to attend to it for him. Tammy had left for New York a few days ago on her cabin crew job and in that time Jen had done everything demanded of her. She hoped that maybe if she was very good Tammy might let her out of chastity when she returned. She knew it was unlikely but hoping was all she had left after giving everything first to her mistress and then again to her master.

Soon she made her way into the room shared by the man who earned Tammy's time and body. She thought of all the times she had listened to Tammy cum while impaled on his superior and massive cock. The first time she watched them fuck in person she was mesmerized. Tammy’s face was contorted in ecstasy far greater than anything Jen had ever given. Her heart and stomach ached as she watched their union. Every time they finished she was made to clean them both. It was humiliating to see the woman she loved more than anything cumming on another man’s cock. It was worse still to taste her pussy so full of cum when it was stretched and used beyond recognition. Worst of all though was tasting his fiancés sex on her new boyfriend’s giant member. More than once the humiliation had made her clitty twitch and they both made sure to let Jen know it hadn’t gone unnoticed and clearly she liked it.

She set down the tray quietly and looked at her master. He had six pack abs and short dark hair that framed his gorgeous face. His arms and legs looked strong like they had been crafted out of marble and wrapped in soft musky flesh. She looked at him sleeping like an angel, or more likely a devil and decided it was time so she slipped below the covers to wake him up.

She found his penis hard as a rock and ready. In times past Tammy would be there silently watching with a hand on the back of her head to remind her she had no control but now it was just them and she couldn’t pretend she was doing it for Tammy. She slowly pulled down his boxers and his magnificent member bobbed in front of her face, she kissed it reflexively after doing it so many times. Her tongue swirled around the head as she tasted the salty, meaty taste of a real man’s cock. She let its head rest on her tongue as she slid the head into her mouth and began to suck. She had gotten good at taking the whole thing but god did she hate that fact. She slid her head up and down going deeper every time. She opened her throat and began to take it as she heard him stir.

Before Jen could react she felt a pair of hands grab either side of her head to hold her face in place. “Well good morning to you too Jen.” Jen knew what was coming but it didn’t make it any easier. He began to thrust his huge beautiful cock into her throat. At first he just moved his hips a little bit and Jen focused on pleasuring the head of his perfect flesh stick. Harder and harder he began to fuck Jen’s face bucking his hips like he did when he took Tammy. She tried to let her mind drift but every time he entered her throat again she felt ashamed and violated. Every time he pulled his glistening meat rod out of her throat she tasted the precum on the head of his cock on her tongue. Before long she heard him say “ slut I’m going to cum in your mouth, don’t swallow just hold it there.” She braced for one of his massive loads and he began to grind his cock on her tongue harder than she ever remembered him doing it before. His cock twitched that incredible and unmistakable pulse on her tongue before blasting his gift into her mouth. Jen felt it hit the back of her throat but didn’t dare swallow and soon her mouth was completely full of his love.

“Sit there silently while I eat then I have another task for you.” Jen hated the taste of sperm. It was humiliating having to sit there and taste it while he ate the delicious meal she had prepared but she knew if she swallowed or moved she would be beaten badly so she did as she was told. 30 minutes later he turned to Jen to address her again “get on your knees I want to do some face painting today.” Jen didn’t know exactly what he meant but knew it couldn’t be good. She did as instructed and got on her knees staring up at him from an angle she wished she was unfamiliar with. The master stood with his cock again at full mast. It’s length was close to 9 inches and it was the perfect girth . He told Jen to tilt her head back and open her mouth. He dipped his cock into her mouth and took it out and brought with it some of his cum she had been keeping warm. He quickly ran his dick across her face and repeated the process several times until her face was covered in his juices. “Now you look fuckable Jen. Actually that’s not a bad idea” he grabbed her head and without warning he rammed his long steel flesh stick into her throat. Jen tried to keep cool and was able to do so but she was dangerously close to gaging and knew that that would be a canning if she did.

He lasted for ages this time and Jen’s jaw began to ache but she had to press on. Jen felt his cock thrust across her tongue and stop just short of the opening to her throat. For a brief moment Jen wondered if he was going to pull it out before he thrust his hips forward and drove his member violently into her throat. Jen tried to breath and swallow both her pride and his cock. He stepped forward holding Jen’s head and began pushing himself deep into her face. She felt his penis deeper than it had ever been and still he trusted ever deeper. Without saying a word he stepped back and removed his cock with an audible pop from her throat and mouth and began to shoot thick hot ropes of cum onto Jen’s face. In time with the rhythmic pulsing of his cock more and more cum shot out onto Jen’s face. She could hardly believe he had so much still left in his heavy balls. “Don’t clean yourself off today I want you like that all day do you understand me!?” “Yes master of course” Jen knew there was no point in fighting, it would only end with her getting whipped or worse and doing what she was told anyway so she swallowed her pride and left the room.

“Go get started on your chores, I don’t let you live here because I like you slave now make yourself useful!.” She knew what the next few hours would hold and so she set out and did the long list of chores left to her by the master. She began to wash the dishes and do the laundry and before long she was washing Tammy’s panties. She found it heart breaking to do it as Tammy would often left her boyfriend fuck her and then put her panties back on to ensure that Jen would be washing out the cum stains by hand. She couldn’t help herself and brought them up to take a sniff. What would Tammy think seeing her like this? Would Tammy think he was even less of a man? Was that even possible? Jen kept washing the soft lacy material and thinking about all the times the master had been inside Tammy while Jen lay awake listening to her scream in ways Jen could never make her. The tears began to well in her eyes but soon they mixed with the dried semen and her eyes began to burn. This made her start to really cry. As the embarrassment and pain mixed she felt her clitty growing in her cage.

The master flung the door open at hearing the crying. “ Why were you sniffing my girlfriend's panties!? Are you fucking crazy, you slut bitch!? I’ll give you something to cry about” Jen froze as the master grabbed her by the arm and drug her into her room. She trembled thinking she was going to get punished but she soon found she was strapped on her hands and knees on the bed and she became even more afraid. “Jen I think it’s time we see what this machine can really do, and to celebrate turning it all the way up I got you a present.” He pulled out the biggest dildo Jen had ever seen. It must have been 12 inches. “This guy is going to destroy your asshole while I destroy your mouth again.” Jen knew better than to beg or plead so she just quietly said “yes master, thank you master” Jen heard him changing attachments and lubing up the monster before she felt it aligned to her tight pussy. “Jen, after today you my slut are going to gape” she felt the head push into her and she left out a shudder, her clitty betrayed her and she felt it strain against its cage. “Oh and don’t cum or you’re telling me you love it want to ride it for even longer”

The machine whirled to life and Jen thought she was going to split in two. The monster pushed further into her than she thought was even possible. Just as she thought she couldn’t take anymore it began a long retreat from her before once again forcing its way inside her. Slowly the pace picked up as she heard each click indicate it was about to get a little worse for her, but if she was being honest with herself she loved it. Every time it got faster she felt a little prouder of how well she was taking it, but her brain fought against the idea she was enjoying this humiliation punishment. How could she claim to still be a straight man if she was enjoying this? The confusion and the emasculating only made her cage tighter on her twitching clitty.

Soon her master was in front of her completely naked and Jen had to admit to herself, he was a near perfect specimen of a man, with a perfect tool. “I have something else I want to try Jen open wide” he produced a metal ring and harness that he then fixed to Jen’s face. Jen was distressed to see she couldn’t close her mouth. “Jen I’m going to use your mouth and throat like a fleshlight today. If you thought I was fucking it hard before, you’re in for a rude surprise.” Before Jen registered what she was told he drove his cock into her throat with such force Jen thought she was going to black out between the two cocks. The master began to fuck her face so hard his balls were making loud slapping noises on her chin. The dildo was driving her wild in the meantime, it was fucking her so hard and fast that it was almost hurting but she couldn’t say anything or try a safe word with the cock taking her breath away over and over.

With every thrust he made he pushed her back onto the dildo and it made the pace of the machine feel even faster. Soon the rhythm was too much and she couldn’t think or focus on anything else, her world was this moment between these two cocks bouncing back and forth between them. She felt her body begin to react in time with them and she would open her throat when she came forward and relax as she came back and in this way she was almost able to enjoy it. Her body became in tune and, as much as she hated to admit it to herself, she felt like the centre of the world.

It wasn’t long before she felt the master slow his pace and rest his cock at the back of her mouth. “I'm going to blast this straight into your throat, if you gag or do anything other than swallow it all so help me I will push you down onto that machine as hard as I can.” Jen felt the pulsing and then the flood gate open as the cum flowed into her throat. She swallowed and swallowed and even though this was his third orgasm of the day it seemed like the biggest. He left his cock in Jen’s mouth and told her to look at him “ be honest Jen do you like the huge dildo?” Jen knew it was a trap, if she said yes she was damned to keep taking it like this but if she said no she would be punished and left on it as a lesson. Like everything else in her life it was a lose lose game. “Yes master I love it” her pride died a little more even after she thought it was all gone. “Good in that case I’ll leave you on for an hour or two then you can make me supper.”

Over the next hour Jen’s body relaxed and she found that the huge dildo was sliding easier and easier into her, the pain had all but subsided and she was suddenly able to let her mind wander as the device worked her over. Soon she found herself imagining Tammy’s pussy before her face. The scent was intoxicating and her mouth was watering for it. She imagined probing that perfect temple to femininity with her tongue, sucking on her clit and feeling it grind against her face as the goddess wielding it began to cum. Worshipping the divine while her masculinity was thrust out of her. Soon she felt her balls grow tight and a tiny sad dribble of cum emptied out of her and she heard herself moaning through the O ring in her mouth.

“What the fuck did I tell you?! Don’t cum! Well in that case it’s twenty lashes with the cane and you’ll spend the night on the machine you slut!” Jen felt the dildo being slid out of her and quietly marvelled at how easily it did so. She felt movement on the bed behind her and realised the machine was being moved to give her master room to swing at her exposed ass with the cane. “Jen this is going to hurt and I want you to know, this wouldn’t have happened if you just had a little self control” the master reached back and brought the cane down as hard as he could and Jen jumped against the restraints. She let out a cry like an animal caught in a trap. Again the cane made its round trip at lightning speed and brought a guttural cry from Jen. It came down on her again and again every time eliciting yelps and squeals. By the time he stopped, her ass was red and swollen with growing welts in a few spots where the cane had slammed into her skin. “Maybe next well take your ability to cum Jen since you can’t behave!” Jen couldn’t hear him over the sound of her wheezing, crying, and her heartbeat in her ears. “Now Jen since you are seasoned and prepared I’m going to use one of your holes one last time today.” Jen didn’t hear him as he lubed up his now glistening perfect cock and moved behind her. She only realised what was about to happen when she felt the head of his cock align with her pussy. “This is also going to hurt Jen '' he thrusted into her with no resistance, the dildo had done its job and he felt his body slam against her ass and she screamed in pain.

His cock twitched inside her hearing her cries of anguish. ‘Tammy is right’ he thought, ‘her pain is delicious!’ He began to slam into her over and over harder and harder every time he’d slam the welts and drive his cock to the hilt into her. Jen thought she would pass out or throw up but knew she couldn’t so instead she tried to think of Tammy. She imagined her body and of the times before all this when they could lay in bed tougher after just having fucked but the image flipped to Tammy laying next to her best friend after Jen had made them dinner and then his best friend and her had a night of hot passionate sex. Then she tried to imagine the drives they used to take and the conversations of their future but again it morphed into Tammy reaching over and wiping her tears away as Jen cried about becoming more feminine as the humiliation was to much for her, before using the tears as lube to masturbate in front of Jen. She imagined their apartment and sitting on the couch having a quiet evening at home before it shifted to Jen on her knees sucking the very cock in her now. She couldn’t escape no matter where she tried to escape to in her mind her new life permeated every aspect.

He began to slap her ass between thrust and Jen went wild. She was bucking and screaming but was too into it to stop. The cocktail of pain and pleasure was too great for her to deny her enjoyment of it. Soon Jen was out of her mind and a single image came to her, the first time she was fucked by her master, and Tammy’s words “You will never be a man again after this.” Jen came a second time. The master pretended not to notice he had Jen right where he wanted her. Jen couldn’t deny that she liked it after this. It had taken a little over a year for them to transform Jen to the creature below him and he knew there would be no going back for her now. They had succeeded in moulding her into a near perfect sex toy.

He felt himself start to cum and thrust himself deep into Jen. She shuddered feeling him pulse inside her and his hot cum inside her pussy. He pulled out and told her to stay and laughed as he left knowing she couldn’t move. Her mind was swimming now. Had she really just orgasmed on her master's cock? Was this really what she wanted? She knew that Tammy would never let her hear the end of it. “See I told you. You are made for taking cock Jen. You just didn’t know it when we met.” Even just the thought of Tammy saying that to her made her twitch and her stomach drop. Maybe she was right.

The master returned with a camera and began to film. “We’ll Tammy, I think we finally did it! This little slut just came on cock twice in one day! She knows what she is now babe! See you soon.” He quickly pressed a few buttons and turned the camera toward Jen and to her horror she was watching herself be a whore for him. Everything they had done today. “Tammy wanted something to remember the day you broke!” He sent the videos he’d taken for Tammy of the whole event to her. He knew she’d be rubbing her pussy to it over and over enjoying the sweet humiliation she had brought to her pet at his hands.

While Jen’s mind grappled with the realisation that video evidence of who she really is was in the hands of her mistress and master she felt something pressed against her now gaping hole. Her master slipped a large plug into Jen.” I want you to leave that in until I tell you to take it out, understand? We don’t want you leaking all over the house or for you to loose that new stretched opening of yours.`` `Yes master” her voice up an octave from all the pain and crying. “Now get to making dinner I want everything done early so I can get you back on the machine for the night.”

Jen walked to the kitchen but it wasn’t easy. Her ass hurt from the canning and hitting and her pussy was stretched like never before. Every step she could feel the plug shift and at times it hurt but other times she almost liked it. Her throat hurt from being fucked so much and her jaw was tired. She had one load smeared and dried on her face, she had drunk two loads of his and had one more in her ass. They had a video of her doing all of this and cumming on camera twice from being fucked. Worst of all was her sense of worth, she felt like a cheap toy, used and discarded and worse still she wouldn’t get the attention of Tammy for this just the hard thick cock of master.

Jen went through the usual motions of making dinner and through her pain and humiliation she was still able to make a wonderful meal. As she served it to the master he made a simple command “on your knees sissy.” Jen got down onto her knees and there she stayed for nearly an hour while her master slowly ate his dinner and watched television. When he was done he handed her the plate and told her to take it to the kitchen. Jen quickly took it to the kitchen and knew that this night was going to end in misery for her like so many others. She didn’t dare try to find a reason to waste time and so decided it was better to return and face her fate.