Zoey's Basement Transformation Pt. 01

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A pathetic young man's transformation begins.
3.3k words
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182.7k
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Part 1 of the 3 part series

Updated 06/08/2023
Created 09/05/2016
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Jack finished his morning workout by stretching. Sweat dripped off of lean muscle as the warm early sun beat down on the bare skin of his chest. He bent to pick up his water bottle, thankful for a sudden cool breeze as he made his way back up the short driveway of his nondescript house in his painfully ordinary cul-de-sac. He smiled and waved at a neighbor as he walked through the door into his pleasantly cooled house.

He grabbed a towel as he walked by the closet, then moved to the kitchen and poured himself a glass of water, walking further into the house as he drank it. He stopped at the stairs to the upper floor, but hearing no footsteps or movement from above, decided he should check downstairs. He unlocked the surprisingly heavy door to the lower floor and pulled hard to open it, then stepped inside, and let the door close itself behind him. The deadbolt automatically locked tight with a loud "clack" sound as it shut. The only way past it was to know the 4-digit code for the keypad. Moving downward, Jack pushed his way through an identical door, everything about it being exactly the same as the one above, except, of course, for the 4-digit code.

As he opened the second door he suddenly heard the sound of his wife's voice.

"...have to remember all the lessons you learned here or she'll send you back, and next time I won't be so lenient with you."

Jack smirked. His wife? Lenient? She was a lot of things, but that was one she couldn't lay claim to.

"Yes, Mistress," came a docile reply.

Jack finished shutting the door, checking to make sure it closed properly, before turning to take in the scene.

Jack's wife, Mia, stood on the far side of the room wearing yoga pants and a sports bra, both of the form-fitting garments looking incredible on her meticulously maintained physique. In her mid thirties with shoulder length red hair and stunning green eyes, she could have passed for a woman ten years younger.

On the floor kneeling in front of her was what appeared to be a young woman in her early twenties wearing a similar outfit. She stared at the floor submissively as Mia continued to lecture.

Jack interrupted with a polite cough. "Good morning, ladies," he said, "Working hard?"

Mia looked up with a smile. "Good morning, Hun. Did you have a good run?"

He nodded, "Just a short one to the school and back. I've got a couple advanced clients today."

Mia rolled her eyes, "It still amazes me that you workout before you go to work, where your job is to workout.

Jack bowed playfully, "The life of a personal trainer isn't easy." Gesturing to the girl, he continued, "I'm not interrupting anything, am I?"

"Oh, no," Mia said, "We were actually just wrapping up. Zoey's Mommy will be here to pick her up in about an hour so she needs to get cleaned up and changed anyways."

Mia snapped her fingers at the girl, "Zoey, towel off your Master Jack."

"Yes, Mistress," she said meekly, jumping to the task before the words were even out of her mouth. She took the towel from Jack's hand and started patting him down with it.

"When you're done go get ready to see your Mommy. I talked to her just this morning and I can't tell you how excited she is to finally get her little girl back." The evil glint in his wife's eye made Jack smile. Looking back at Zoey he could see her visibly pale at the mention of her Mommy, her eyes distracted as she slowly dried him. Still, she did a good job, making sure to be gentle but firm, but as she reached the waistband to his shorts, she hesitated, looking up at him.

Jack nodded, giving her permission to remove his shorts. She grabbed the damp garment by the waist and peeled it off, slowly revealing his large, hairless genitals. Hung at right around eight inches and impressively girthy, Jack couldn't blame Zoey for the way she licked her lips and swallowed nervously while eyeing it.. Behind him Mia gave an impatient throat clear, shocking the girl into action, maneuvering his manhood around so she could properly dry it. She spent an inordinate amount of time there, becoming fixated as, under her gentle ministrations, Jacks cock started to grow.

He ahemed, "Unless you'd like me to have to use you again before your Mommy comes to get you, I'd suggest you move on."

Zoey blushed furiously, immediately moving on to his legs and finishing. His wife gave a delighted giggle at the reaction. When she felt she had done a satisfactory job, Zoey looked up at him questioningly. Jack gave a curt nod, making Zoey smile as she leaned down and kissed his right foot, then tilted her head to put her cheek on top of the same foot.

"Thank you for letting me serve you, Master," she said, "How else may I be of service?"

Jack looked down and saw that she was nervously eyeing his cock again. He chuckled, addressing his wife over his shoulder.

"Hungry little slut, isn't she?"

Mia laughed, "You would be too if you hadn't cum in that long."

Jack shrugged, trying not to think about it.

"Thank you, Zoey, but no, that will be all. Now go get cleaned up like your Mistress ordered."

She nodded submissively, "Yes, Master Jack."

She stood and walked toward the door that led to the bathroom, but Mia stopped her.

"Hold on," she said, "Why don't you strip out here and show your Master Jack the whole finished product?"

Zoey turned back, blushing deeply as she did so, but still she did as told, hands obediently pulling her clothes off. The sports bra came off first, revealing smooth, hairless skin shining with sweat. She had very small breasts, barely even A-cups, but they seemed to suit her just fine, and Jack could vouch for their sensitivity.

Next she turned her back to him, stretching low and pulling her tight yoga pants down over a full, spankable bottom, putting on a bit of a show as Mia had thought her. Jack felt himself start to stiffen at the sight. He shot an annoyed glance at his wife who smiled innocently, as though she had no part in tempting him with this display.

Finally, Zoey turned back around to face them, fully naked. Once again Jack marveled at how complete the transformation was. To all appearances, Zoey was a docile, obedient young lady. Hell, she'd probably be insulted if you didn't think that. But despite all evidence to the contrary, hanging there between her legs were a set of male genitals locked snuggly away in a chastity cage.

Jack walked closer, thinking about when she had first shown up as a petulant boy named Aaron several months ago. On arrival he was overweight, unmotivated, and had been leeching off of his wife, a woman almost ten years older than him, for nearly a year. However, as the year wore on, she had slowly introduced him to the concept of a female dominant relationship. She had reasoned with him that because she made all the money and paid all the bills, that she should also get to make the rules. Seeing no alternative, he had reluctantly agreed. Over the course of several months the rules became more strict, pushing him further and further until, one day, he rebelled, refusing to play along any more.

Unfortunately, this is exactly what his wife had planned on. Because he refused her authority outright, she presented him with an ultimatum and two sets of legal papers. Attend a special facility where he would learn what was expected of him by his wife over the course of a variable stay of several months, or get divorced.

Having no skills, education, or motivation, divorce hadn't seemed like a smart gambit. And so it was that Aaron, with much trepidation, signed away his rights to his wife for the duration of his stay in the special facility, granting consent for any treatment deemed necessary for his "rehabilitation".

That night he had been delivered to Jack and Mia's house, blindfolded and handcuffed, dressed in nothing but a thin robe. And so his own personal hell had begun, brought on by nothing but his own laziness. The first week was always the hardest. He was put on a strict diet, started on an exercise regimen, given voice training lessons to help feminize his voice, and taught how to dress like a woman, including doing his own makeup.

Most importantly he was fitted with adorable pink cuffs on his wrists and ankles, a matching collar around his neck, each with a sturdy D-ring attached. Each cuff had been locked on as well, preventing any kind of tampering. Not that she would try that now, but her first night had been a memorable one.

After being taken inside and properly restrained, Mia had started the introductory portion of his transformation, explaining to him that from now on his name was Zoey, and that for the foreseeable future he would be treated as a girl. A slave girl, in particular.

He had protested of course. Pulled against his restraints, spat, swore, begged, and each time he resisted, Mia explained that his punishment was growing steadily worse. Naturally Aaron, or Zoey as she was now being called, ignored her, continuing to dig herself into an even deeper hole.

Eventually Mia had lost her temper, shoving the contract he had signed into his face.

"Do you have any idea what this means?" She'd asked him.

He'd opened his mouth to give some smart alec remark when she reached down and grabbed his balls in a tight fist, squeezing until it looked like he was about to be sick. He'd struggled to fight it, but with his cuffs locked together behind him, there wasn't much he could do about it.

"It means that you gave me legal permission to do that to you whenever I deem it necessary." She finished, releasing her grip to the sound of pained gasping. "And trust me, if you think giving your worthless little grapes a gentle squeeze is the worst I can do to you, you're in for a world of pain."

The fear that had reflected back up to her from Zoey's eyes had lit her desire as well. She walked to a dresser nearby and opened it up, pulling out a few tools. When she walked back to him the first thing she brought out was the pink ballgag. Zoey flinched away from it, but a quiet reminder about how much she enjoyed the sensation of testicles being crushed in her grip encouraged her to open her mouth, even moving her head back and forth to help fit it. With a snap the gag snugged into place, filling her mouth nicely. Next Mia took a length of rope and tied it to his cuffs, then looped it through a set of chains hanging from the ceiling, however she left a lot of slack in it.

Leaning down, she closely inspected Zoey's genitals for the first time. Her cock was smaller than average, and her testicles were likewise unimpressive, though they would function for the job Mia needed them for.

Reaching into a pocket she pulled out a custom made chastity cage designed especially for Zoey. Her Mommy had taken the measurements months ago and had the device made in anticipation of today. Mia just thought it was too bad she couldn't be there to see Zoey locked up in it for the first time. She struggled again as Mia explained what it was for, but there was nothing she could do about it.

Pulling out a small white jar as well, Mia snapped a glove onto her hand as she took the top off and took out a fingerful of orangish paste. Reaching down, she smeared it all over Zoey's crotch, making sure to get it everywhere. Following that, she managed to get the cage onto her pathetic little toy without too much difficulty, giving a satisfied grunt as the lock snapped closed.

Still moving around, Mia continued to set things up as Zoey started to notice a very unpleasant burning sensation around her groin. The heat seemed to compound by the second, becoming incredibly uncomfortable very quickly. Soon she was being quite vocal, whimpering around her gag.

"Oh," said Mia, "You must be starting to feel this," she held up the little jar of paste. "It's a proprietary blend of the business. Mostly vaseline, cayenne pepper, and chili extract." A panicked look crossed Zoey's face, making Mia smile wickedly. "The burning has barely even begun. You're going to be feeling that all night long. Some people even think it's worse than what comes next, but I certainly don't think so in your case."

Mia grabbed a leash and a large set of clamps. Attaching the leash to Zoey's cage, she gave it a firm tug, nearly causing Zoey's eyes to pop out of her head as her hips shot forward to stop the pulling. As the pressure built though, she eventually took quick shimmying steps, trying to follow, her legs going as far as the attached cuffs allowed.

"Very good," Mia said, "I see you understand the concept that when I lead, you follow. Lets just keep that straight and I won't need to attach one of these," she pointed at the clamp in her hand, "To one of those," she then pointed between Zoey's legs. "Get it?"

Zoey nodded vigorously, fear showing plain in her eyes again.

"Good. See? You're already learning. Unfortunately, we still have quite a few lessons to go over from earlier."

Mia moved away from her, going to a wall and grabbing a chair as well as some other things Zoey couldn't see. She moved the chair just behind Zoey, then grabbed her by the arm, pulling her back in a shuffle to the right side of the chair as Mia sat down. Sitting on Mia's lap were a wooden bathbrush and what appeared to be a clear plastic pingpong paddle. Hefting the bathbrush, Mia addressed Zoey.

"Sissy, I know these are big changes you're going through right now, but believe me, they're going to happen. I have as many months as I need to break you down and rebuild you however your Mommy desires, and what she desires is a meek, obedient, fit, little cock slut. You are going to become all of those things. Your wife wants you kept in chastity, and so you will be. She wants you trained to take cock in all of your holes, both the real and fake kind, and the bigger the better, so I'll train you to do that as well. She wants you to look as passably female as I can possibly make you, which means you'll have to fend off male advances regularly. Lastly, though, she just wants you to suffer, and so you will." She said the last matter-of-factly, making Zoey whine.

She placed the implements on the ground, then reached up, grabbing Zoey by the arm and pulling her over her lap, catching her as she started to fall and lowering her into position. As she lowered down, the rope attached to her wrist cuffs reached its end, pulling them up and behind her slightly, where they would be well out of range of interfering with her spanking. Taking hold of the leash, Mia fed it down through her legs, trapping the caged little cocklette between her warm thighs and putting her bottom squarely on display in the center of her lap. She whined through her gag as Mia wrapped the leash around her hand, leaving just enough slack to still be able to hold Zoey firmly around the waist.

Mia ran a hand over the naked bottom in front of her. "Has your Mommy ever spanked you before?" she asked, already knowing the answer.

She gave a reluctant nod.

"Did you enjoy it?"

Vigorous denial.

"That's too bad," she said, "Because I spank much harder and much longer than your Mommy. I'll be expecting tears well before I'm done with you."

Lifting her hand, Mia started, and tears there were. Zoey made it about 2 minutes with the hand before the sniffles started. By five minutes she was struggling as much as the leash would allow, crying as she was forced to endure the harsh punishment with no ability to wiggle or escape. At the ten minute mark she was openly sobbing around the gag in her mouth, all thoughts of dignity long forgotten in the inferno of agony that was her burning backside. Mia paused, but only long enough to grab the plastic paddle from the ground.

"The warmup is over now. I think it's time you met the lexan," she smirked, "You'll be getting to know one another quite well over the next few months."

Zoey was mostly too far gone by that point to register much beyond a brief pause in her punishment. It didn't last long though, as the wicked little paddle splatted down with a furious CRACK! Zoey shrieked through her gag, tears redoubling as the lexan started it's long campaign across her wayward bottom. The swats came hard and often, and over the course of the next five minutes, Mia roasted her ass, leaving it a bright red crimson and hot to the touch.

Sighing, Mia tossed the lexan down and picked up the bath brush, testing its weight as Zoey continued to cry miserably.

"Big lessons for big trouble makers," she said in a kind of sing-song voice, bringing the brush down with impressive force, causing Zoey to start struggling once again. She pulled, strained, tugged, twisting this way and that but nothing worked. Finally giiving in, she slumped across Mia's lap, defeated as the woman continued to bring the bath brush down time and again on her poor defenseless bottom. A short time later, though it probably seemed like an eternity to Zoey, Mia finished with the brush, taking the opportunity to lay on some especially hard swats before she tossed it to the side with the lexan and pushed Zoey off her lap. With her arms still bound, she was forced to kneel, arms pulled up way behind her as Mia stood up.

Mia had hardly spoken during the punishment process. Her philosophy was that the first spanking wasn't really designed to achieve any particular goal, it was simply supposed to inspire fear in her subject. Fear was a great motivator for getting people to do things they didn't want to, and Mia would need that advantage during the later stages of Zoey's training. Besides, the fear would help keep Zoey in line, which would spare her a lot of punishment in the long run.

Mia left the miserable girl to herself for a few moments as she returned everything to its rightful place. As she finished putting away the last items, she turned to eye the pitiful girl, her expression oddly amused.

"Not as much fun as when your Mommy does it?" she asked.

Zoey shook her head miserably. It had been a thousand times worse than anything she'd ever experienced, the fire in her backside continuing to grow until it had consumed her every thought. There was no mercy in the woman, and Zoey flinched back as she crouched down next to her, running a hand over the girl's slick skin, a wicked glint in her eye.

"Don't worry, sissy," she said sweetly, "With all the stuff I have in store for you, it won't be long before you look back at this and think of it as the good old days. Now tell me," she added, her smile seeming to grow an extra row of teeth, "Have you ever been given a proper enema before?"

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SissyBoy1WarszawaSissyBoy1Warszawa12 months ago

Interestingly written, although for me personally (maybe because I am a sissyboy myself and experienced severe violence and even rape) too much violence, brutal beatings ... I am very curious how the whole transformation of Zoey will develop and how his own mother and wife will treat her. Greetings from Poland SissyBoy from Warsaw. 📝🧒👨‍❤️‍👨👧

Interesująco napisane, choć dla Mnie osobiście (może dlatego że sama jestem sissyboy i doświadczyłam ostrej przemocy a nawet gwałtu) za dużo przemocy, bicia brutalnego... Jestem bardzo ciekawa jak rozwinie się cała transformacja Zoey oraz jak potraktuje ją jego własna mama i żona. Pozdrawiam z Polski SissyBoy z Warszawy. 📝🧒👨‍❤️‍👨👧

DomFckrDomFckrover 1 year ago

I am actually looking for sweet sissy bois to mol and make into my own little Zoey. I will help him transform into a Gorgeous beautiful sweet sissy and if lucky enough a full on transformation from a trap to a trans beauty all the boys want to have, own or have sex with and the girls will want to dominate. But she will be my prize and pride in joy maybe even going further or closer then my last gurl. More then fun and games it will be a life lesson and mentorship better then anything you can imagine as it will be reward based and she will crave and want the pleasure, the fun and joy along with the freedom of stress and having a daily grind. Instead her true destiny and purpose will be acheived. Come to me now and be better then Zoey..

BumD77BumD77over 2 years ago

15-20 minutes of hard paddling and no serious damage or bleeding. OK. Not what I would expect. Let's see if the next part is any different.

GrrrreatImaginationGrrrreatImaginationabout 3 years ago

Interesting story-line with much (additional) potential. Characters seem worth getting to know, and discovering how the dynamics of Tran-Sexual/Cross-Dressing play out with them is refreshingly attractive. I hope you come back to this some day and let the opening scene be the start and have the story-line move forward from there.

The opening scene would have been a good place to start from for this story to be in the TS/CD category. Because it went quickly into undeniable BDSM and Non-Consent/Reluctance, and spent more time in that content, it seems only fair to categorize it that way, or offer a heads-up at the top of the story.

Off to read the rest of this series.

Thanks for sharing your talents.

AnonymousAnonymousover 3 years ago

nice!!

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