Dom’s Sissies Pt. 1: First Steps (Patreon)

Corey was getting fucked, at least metaphorically, for now. Dominic Mercer, the man his parents had gotten their divorce over, sat at the dinner table of their small, cluttered living room looking thoroughly out of place with his expensive suit and imposing height.

At the same table sat Corey, his mother Amanda, his girlfriend Emily, and his little sister Olivia. On the table between them lay the contract Dominic, and really all the others too, wanted him to sign. The contract that would ostensibly save him from the worst of the gambling debts Corey had amassed with his friend Liam. But this apparent salvation came at such a humiliating price. The same price Corey’s father had paid only a few years earlier.

"Think about it, Corey," Dominic said. The older man’s voice was deep and pleasant, and he tapped the pages of the contract on the table again with his ringed hand. "All your troubles, all your family’s troubles, would disappear." He snapped his fingers to underscore the ease of the rescue.

"But what is a sissy exactly?" Corey asked, unable to meet anyone’s eye, but he heard his little sister giggle and felt his mother shift on her chair beside him.

"Well, that is not something you have to worry about," Dominic announced. "Really that would only become relevant if, after the initial contract has run out, you would still be interested in staying with me." Dominic himself, of course, knew better. Once Corey had given his signature and Dominic’s foundation would begin making its first payments to his family and girlfriend, it would become exceedingly difficult for Corey to not go down the sissy rabbit hole completely.

"Well, Mr. Mercer," Corey’s mother said as she noticed her handsome guest’s cup was empty, "care for some more tea?"

"Why yes, Misses Porter, and thank you," he said, smiling kindly, still calling her by her husband’s surname. Her sissy of a husband, who had abandoned her for this very man, but now, looking at Dominic Mercer, she could kind of understand why. He was a tall, handsome man with a sharp jawline, some slight stubble on it, and dark brown eyes that maintained easy eye contact framed by thick, slightly furrowed brows. And he smelled good, of oud and leather, in a way Terrence never had.

Smiling slightly, she went up and off to the kitchen, glad to be out of the room as the man who had sissified her husband was talking about sissifying her son, whatever sissifying exactly meant. But what could she do? Her dumb son and his dumber friend Liam had, within one year, gotten themselves into a good $11,000 of illicit gambling debt, with mounting interest payments and penalties. She had cried the night Corey had confided in her.

And while she did not know any of the people her son owed money to, from what she heard about them from Corey and Liam, they were not to be joked with, and going to the police would not be advisable either, as both Liam and Corey were only 19 and not yet allowed to gamble.

In the living room, meanwhile, with Amanda out of the room, Dominic decided to use this opportunity to fulfill a little fantasy of his. Sitting across from Corey, he leaned back in his chair, pulled out his phone, made sure it was on mute, and opened a very special video.

Without any of the others in the room knowing, Dominic now saw Tiffany, formerly Terrence, arching her back as she rode him. Her long chestnut brown hair whipped and spilled around her. Her mouth hung open in a soft, perfect O as she moaned, though due to the phone being muted, nobody was any the wiser. Her tiny flat cage the ultimate proof of Dominic’s complete conquest of this erstwhile bully of his. The other sissy in the video, Jessica, younger than Dominic and Tiffany both, was playing with Tiffy´s nipples.

Dominic looked from over the phone at Corey, who was looking down at his hands. The idea of first sissifying his old bully from the 90s and then his son, who, by what Dominic’s PI had figured out so far was not much better than his father, was just exquisite.

Corey was good looking in a pretty-boy sort of way, which was exactly the right foundation for sissification in Dominic’s mind. He had light brown hair and eyes and at only 5 foot 6 was a bit smaller than his girlfriend. Dominic thought it was quite possible that he also weighed less than her.

Then Corey’s mother came into the living room again bearing his cup of tea and he put his phone away again as she apologetically muttered, "I’m sorry Mr. Mercer but I seem to have run out of sugar."

"No problem at all," Dominic said, taking the cup of tea, and then decided to continue the conversation. "Of course Corey, your girlfriend," he motioned at Emily, "has already agreed to join as well, as I’m sure she’s told you." Emily nodded and Corey said, "Yes, we talked about it last night."

Getting Emily on board had been important for Dominic simply because the idea of sissifying Corey while training his girlfriend up into a proper mistress was irresistible.

Corey meanwhile wondered how his life had gotten so out of his control. A year ago he and his friend Liam had gone illegally gambling to celebrate his eighteenth birthday and because neither of them wanted to wait for three more years. Now, barely a year later, his life was completely fucked and he was seriously considering signing up to do this perverse shit for three months. Apparently Liam had already signed as well, though Corey had an easy time imagining that for Liam being out of his stepdad’s house for the next three months was likely an improvement no matter what sissification entailed.

He was pulled out of his thoughts by Emily beside him gently squeezing his thigh. All four pairs of eyes watched him and he suddenly felt incredibly self conscious. His skin started to itch and he looked down again.

"Well?" his mother asked and he saw his sister move to cover her mouth. "Fucking bitch," he thought. Then he said, "Nobody can know about this."

"Of course," Dominic said airily.

"I mean it," Corey snapped. "Any of you," he looked around the table, "nobody can know about this and after three months I’m out, alright."

"You have my word," Dominic lied easily.

Corey signed, feeling an odd tumbling sensation in his stomach. "What are a couple dresses for all that money?" he asked himself, but looking down at his signature he immediately regretted it nonetheless. As if sensing his regret Dominic snapped the entire contract from the table lightning quick and immediately got to his feet.

"Well, Misses Porter, I thank you for the tea and as we have discussed your son does not need to pack at all. Everything will be provided for him at my manor and you will see him again on Friday."

Amanda got up as well, against Dominic’s expectations. He held his hand out for a handshake, and she hugged him deeply. Corey and his sister looked away.

"Thank you, Mr. Mercer," Amanda whispered.

"Really, it is no problem at all," Dominic said easily.

Outside, as Emily and Corey got into the back of Dominic’s Mercedes S Class, they were in for a surprise. Liam was already in the car, apparently having waited there the entire time while Dominic was inside.

"Hey, Corey. What’s up, Emily?" he greeted them respectively, but like Corey he seemed to have difficulty meeting anyone’s eye.

There was ample room for all three of them on the leather rear bench of the car. The door shut and the Maybach eased out into the thinning late evening New York traffic, slipping past rows of brownstones. And soon they glided onto the FDR.

None of them talked much on the drive but Emily’s thoughts were spinning. All this was like winning the lottery. Her dumbass of a boyfriend had gotten himself in a whole load of trouble, even owed her a couple hundred dollars, and then suddenly out of nowhere came this rich handsome middle aged guy offering her one thousand dollars a month for three months if she helped him with her boyfriend’s sissification. And all that in her gap year, so she could still start college as planned.

Emily had informed herself a bit about sissification in the days prior and decided that it would be quite fun, especially since she doubted Corey or Liam would extend the contract after the initial three month period and so it would be rather harmless and temporary. And it would certainly humble Corey a bit, plus she was sure he would look cute in make up.

In the country estate that was their destination meanwhile, sissies Jessica and Madison were on maid duty today.

The mansion was quiet in the afternoon, so quiet that right now only the clicking of their heels and their soft chatter could be heard in the eastern wing. Jessica and Madison moved through their assigned tasks with silver buckets, a small room service cart they pushed and their feather dusters.

Looking at them now it was nearly impossible to guess that they once had been guys if you did not know better.

Madison, no longer Matthew, now sported voluminous slightly wavy black hair, glossy and thick, falling around her shoulders in soft cascades that moved with every step. Her warm brown eyes contrasted beautifully with the stark black and white uniform, giving her a soft inviting look. The little lace maid cap perched atop her dark hair made her seem even sweeter, almost doll like.

Jessica, once Jacob, beside her wore her sleek perfectly straight platinum blonde hair, cut to fall in a smooth immaculate curtain down her back. Her icy blue eyes were Dominic’s favorite feature on her. The way those beautiful and cold eyes gazed up at him with unmistakable dislike while her lips obediently worked around his cock was one of the best confirmations of his victory.

Unlike their appearance their maid uniforms were identical. A short black dress with white lace trim, puffed sleeves and a corseted bodice that cinched their figures to resemble an hourglass and pushed Madison’s D cups and Jessica’s C cups out respectively. The skirts were just short enough that when they bent, as Dom’s sissies were trained to bend at the hips, the layered petticoats would lift in a practiced flutter, exposing the tops of their fishnet stockings, the pale straps of their garter belts and even the lace edges of their panties and the butt plugs beneath. In front their lacy panties covered their flat metal chastity cages.

High heels completed them and forced a delicate sway to their gait. The open toed design presented their painted toenails to the world, today soft pink on Madison and white on Jessica.

Jessica wiped down the banister with swift strokes. Her nipples, constantly sensitive from the hormones, dragged against the fabric of her stiff bodice with every breath, stiffening gently from the friction. She squirmed, thighs rubbing together, which caused the plug inside her to shift. She moaned involuntarily and felt arousal spread out from her belly, where it began as a warm fluttering sensation, throughout her entire body. God, how hormones had reshaped her. Feeling arousal as a man did, concentrated in the cock, was becoming a faded memory. It was something that happened to Attila or Dominic, not her. More than once in recent months she had caught herself thinking about men as separate from herself, thinking of herself explicitly as a sissy. It seemed Dominic was now even winning in her own mind.

The constant pressure of the butt plug against her prostate was so emasculating, a constant reminder of Dominic inside her body.

She bent down to scrub a tile, and another soft gasp escaped her lips. "Hnnn..."

Madison, who was kneeling at the baseboards scrubbing gently, looked up smiling absentmindedly and asked, "You alright, babe?" The gentle rocking motion of cleaning made her plug nudge upward with each stroke, sending fluttery heat through her belly. Her clitty pressed lightly and impotently against its tight cage. Unlike Jessica, Madison enjoyed all these sensations outright.

Jessica flicked her a look. "I’m fine. God, Maddie... what are you smiling about?"

Madison blinked up at her. "Oh, uh, was I?" She glanced back at the tile, brushing a stray hair behind her ear. The tongue stud caught the light when she spoke. "The new girls should be arriving soon."

"You really think they were dumb enough to sign?" Jessica asked, arching one perfectly shaped eyebrow.

"We were," Madison giggled.

Jessica rolled her eyes. "Yeah, yeah, but seriously? Boys are still signing? You would think someone would have warned them by now."

"Well from what I heard," Madison said as she scrubbed, "that Corey is definitely gonna sign because Misses Mercer’s son."

"Right," Jessica said. She had heard that too.

The sissy Dominic had made his wife was the oldest one here, apparently his very first. But she had only permanently become a sissy about four years ago. Before that she had lived a double life for quite a while.

And she liked to talk. A lot.

Especially about her two actual children, an eighteen year old daughter and a nineteen year old son. Corey.

Dominic meanwhile was guiding the Mercedes north along the Hutchinson River Parkway, the trees thick on either side. And he was wondering about whether he would still have time for today’s scheduled workout now that he had taken this detour to get the three or whether he should skip chest day this week. But looking into the rear view mirror, seeing Corey Porter sitting there looking outside, he decided he would get his workout tonight fucking Corey’s sissy mommy. Fuck, he was horny now.

As the exit approached he eased into the right lane, already picturing Tiffany moaning beneath his toned body.

Approaching the massive entry gate to his property he pulled down his window, greeted Michael Duster, who was on duty tonight, and then said to all the occupants of the car, "Welcome to the second largest Mercer property."

Corey just nodded as Emily launched into small talk with Dominic about the property, at least he hoped it was just politeness. He barely heard a word. Ever since Dominic had stepped into his living room earlier that day Corey had felt small, intimidated in a way that made his insides feel slick.

"Shit... how could any of this have happened?" he asked himself again, stomach twisting.

The car slowed, then stopped. Corey glanced up and felt his breath catch.

A beautiful mansion stretched out before him, its stone facade glowing softly in the orange wash of the setting sun. Several smaller buildings dotted the surrounding grounds, guest houses, service wings, dorms. The Mercedes had pulled into a small parking lot, half filled with other cars.

As all four stepped out of the Mercedes Corey barely had time to shut his door before a delighted squeal cut across the parking lot. A moment later he was yanked into a tight perfumed hug, soft arms wrapping around him with startling enthusiasm. He did not need to look up to know who it was.

His dad. Terrence Porter. Or rather now, Tiffany Mercer.

Corey had only seen her a few times since the divorce, but seeing her now was alarming. Worrisome.

Tiffany was more feminine than Corey’s mother had ever even attempted to be, a full Stepford wife fantasy made real. Her long brown glossy hair curled perfectly over her shoulders, her lashes thick and fluttery, her lips a soft cherry gloss. She wore a cinched pastel dress with a sweetheart neckline, pearls at her throat and a tiny polished waist that looked like it had never known a day of male muscle.

Her voice was breathy and musical. "Oh, sweetheart, it is so good to see you again."

Corey swallowed hard. "Yeah... hey, uh... you," he said and was relieved to see that his awkwardness did not impede Tiffany’s happiness.

"That voice," he wondered, "how did they manage to make that voice? Fuck. Is this what happens if Liam and I do not jump ship in three months?" Tiffany’s speech was soft and lilting, every word floating out in a breathy practiced sweetness. Terrence’s voice had never been truly deep, but this was certainly unnerving.

Since his parents divorced Corey had met his father only intermittently, but every time they had met he or she had been more and more feminine.

Liam had observed the entire scene somewhat baffled as he did not know the woman that had hugged Corey. Though they seemed very close. Corey, having been ashamed of the transformation his father had undergone in the last few years, had never told him.

Now Dominic had already seized Tiffany by the waist and pulled her in for a kiss. His hand bracketed her lower back, firm and possessive, lifting her slightly onto her toes as he angled her head back. Tiffany melted into him instantly, her body leaning in delicately. Corey and Liam both looked away but Emily only smirked. This was getting better and better. Tiffany’s lashes fluttered as she offered him her lips and the contrast between the two was undeniable. Dominic tall, solid, commanding, and Tiffany soft and yielding in his arms, only being able to react.

"Alright," Dominic then announced, immediately taking command of the situation, "Emily, Tiffany will show you where the other superiors in training sleep." He looked at Tiffany and smirked, knowing full well that she would prefer to spend some time with her son right now, but if he had learned one thing when it came to sissies it was that they needed to be teased. "And I will be showing you two," he motioned toward Liam and Corey, "where the other beginners sleep."

Liam and Corey followed Dominic through his mansion as he explained, "Madison and Jessica are house girls. They will be responsible for the two of you the next couple days. In this mansion sissies pass through three classes before they are finished. Beginner, intermediate and advanced." He then paused for a moment and looked at them, a knowing smile playing on his lips and a twinkle in his eyes, "Unless of course you will decide to leave us when the three months are up." Corey said nothing, but the way the bastard had looked at them was ominous.

Dominic led them down a quiet side corridor of pale pink doors, the sound of his polished shoes steady on the hardwood. Corey and Liam followed a step behind, both tense and lost in disbelief. Eventually Dominic stopped in front of one of the doors and said, "If I remember correctly, this one was free."

Dominic pulled out a keycard and held it against a reader next to the door and a soft click indicated that the door was now open.

The room was small. Smaller than Corey expected. Two narrow beds sat side by side, close enough that the blankets almost touched. Both beds were made with soft pink duvets, white lace trimmed pillows and little decorative cushions shaped like hearts. The walls were painted in a warm pastel rose and lined with framed photos of feminine poses, corset silhouettes and vaguely inspirational quotes. It was very much meant to impress their new status on them.

A large vanity took up the far wall, covered in neatly arranged brushes and palettes, next to which stood a rack of identical pink robes. The bathroom door stood open. White tiles trimmed with gold, soft lighting, an overly large mirror bordered by tiny bulbs and two toothbrushes already waiting for them, each tied with a ribbon.

Liam exhaled shakily. "This is a joke, right."

Dominic simply laughed. "Not at all, little guy." He motioned casually toward the beds. "Madison and Jessica will be here shortly." He paused then, letting his gaze pass over both boys with a softer expression than either expected. "And truly, welcome. This place will be your home for a while, so treat it as such. I take care of the people under my roof."

He gave them a small nod before turning toward the door.

This took Corey aback. Dominic exiting on such a note did not fit into his mental model he had made of the man.

For a moment neither Corey nor Liam moved. They just stood there staring at the beds, the vanity, the soft pink everywhere. The tiny glittering heart stickers on the mirror. The perfume sampler tray. The lace curtains over the window.

Liam rubbed his face. "Holy shit dude, this is real."

Corey just growled, "Fucking gambling."

Before either of them could do anything there was a light knock at the door, followed by it opening without waiting for permission.

Madison entered first, smiling brightly. Jessica followed, posture perfect, expression bored and slightly annoyed, though her eyes flicked over the boys with cool appraisal.

"Hi, how are you," Madison said cheerfully, clasping her hands in front of her. "We’re Madison and Jessica. We’re the house girls assigned to you for the next couple days."

Jessica nodded once. "We handle your schedule, your grooming, your orientation and everything else Mr. Mercer wants."

"Fuck," Corey thought, looking at these two pretty girls, unaware as he was that these were sissies. He had not expected that girls his age would be there as well. This was humiliating.

Madison and Jessica no longer wore their maid uniforms. Instead they wore casualwear they got to pick themselves. Madison was in a soft lilac sweater that hugged her waist paired with purple leggings. She was barefoot on the heated floor of the mansion and her black hair spilled freely over her shoulders. Jessica by contrast wore a fitted pale blue top that revealed the sculpted curve of her corseted waist, tucked into a short white skirt that showed off her long legs. Her platinum hair lay in a smooth sheet down her back and she had switched to sleek nude heels.

"Are there also gonna be any... others... like us?" Liam asked carefully, looking between the two.

"Like you?" Jessica asked. To Liam her voice sounded snooty, but she was a hot chick nonetheless. "The entire mansion is full of us, maybe thirty here, and several dozen more over the entire country, I think."

"No, I mean... when I say 'like us' I mean..." Liam struggled to find the words and shook his brown haired head. Corey intervened. "He means other guys like us who signed that fucked up contract for money."

Madison giggled at that as it dawned on her these two guys thought they were actual girls, and Jessica seemed annoyed saying, "I just told you."

"Jessi," Madison tittered. "They think we are real girls."

"Ohh," Jessica said, on the one hand feeling flattered and on the other annoyed at herself for that. She should not feel flattered for looking like a real girl by now.

"You are not... ah, fuck off, you are not," Liam said robustly. He looked again at Jessica’s face, and there was no trace of masculinity to be found there anywhere. She had long, dark, and helplessly fluttering eyelashes that beautifully framed her cold blue eyes. Full, pouting lips painted in a dark cherry red, and there was certainly filler at play here. And while her hair was clearly bleached blonde, it otherwise looked real.

Madison, who increasingly seemed like an airhead to Liam, giggled again at that. A pleasant girlish sound. Then with one hand she delicately pulled up her skirt and revealed white crotchless lacy panties, and in the central hole a small penis encased in a flat chastity cage.

The lack of a crotch area in the panties rendered them purely decorative as instead of hiding her locked clitty, it instead framed and pulled the eyes toward the small, flat, metallic cage that could not have been much bigger than a single inch. “My trophy,” as Dominic liked to call it.

"What the," was all Liam could manage. He had signed a contract to be a sissy for three months, but in his mind, sissy had meant guys, clearly recognizable as guys, would wear dresses and skirts for three months and prance around for the enjoyment of middle-aged perverts. He had not looked forward to it, but the gambling debts had to be settled somehow.

But clearly this Dominic Mercer was running a far more sophisticated operation here.

Liam shook his head. He could not make eye contact with either of them now and felt a hot prickling all over his face. Was this what Mercer had planned for them? Madison and Jessica looked and sounded so utterly feminine.

"We are going to take you now for your first before and after picture, alright," Madison chirped. Liam still found it difficult to accept that this was, or had been, a guy, and Corey asked, "Before and after picture."

Now Jessica answered. "Yes, we all had them taken at regular intervals during our sissification. Not so much anymore since we have been finished though. This first one will be you as you are now, and then we will be putting makeup on you and making you as feminine as possible, given," she looked both of them up and down and seemed to sneer, "well, given what we have to work with so far."

"But these pics stay private, right," Liam shot in, worried. Corey nodded.

"Sure," Madison said cheerfully.

Jessica turned, expecting the boys to follow without question. Liam shot Corey a queasy look, and Corey swallowed hard, and off they were.

Jessica and Madison minced like well-trained sissies, while Liam and Corey, following them, still walked like guys.

They were led down a short hallway, the windows outside showing the red of the evening sun. Then through another pink-trimmed door into what looked like a small professional photo studio. A white backdrop had been set up, a sleek digital camera mounted on a tripod that faced it, and some standing lamps.

"Step inside, please," Jessica said, guiding Corey forward with a hand at the small of his back. He almost wanted to say something. Corey felt heat creep into his face. It was humiliating to have this sissy treat him like that. But he guessed being rude might blow up his contract, and he really needed that damn money.

In no time at all the before photos of both were taken.

"Good. Now onto the other photos," Jessica said, stepping out from behind the camera. Her eyes lingered on Corey, seeming faintly amused. In truth, she was glad for every new sissy that arrived and had to share her fate. So many guys liked sissies because they used them to feel secure in their own masculinity, which was usually more fragile than they pretended. Seeing guys like Corey get pulled under too ensured that they could not view her as just a sissy.

"Now we will split up. Madison will finish Liam’s set and get him ready. And you are coming with me," Jessica said to Corey. She knew that Corey was Tiffany’s son and she knew that his girlfriend was with him. She intended to have a bit of fun and let Emily and Tiffany see Corey done up for the first time, and they would see how he put his first chastity cage on.

Jessica guided Corey toward a small nearby room as Madison and Liam split from them.

It looked like a beautician’s parlor redesigned by a sissy. Soft pink walls, gold trim, and delicate sconces cast a warm glow over everything. Three salon chairs sat in front of a long illuminated vanity, each one upholstered in plush pastel velvet with little embroidered bows on the headrests. The counters were lined with neatly organized brushes, curling irons, palettes, perfumes, and rows of lip glosses arranged from nude to deep rose. A faint scent of vanilla and lavender hung in the air, unmistakably feminine.

Corey sank into one of the chairs, the seat far too soft and welcoming, and immediately felt ridiculous. His feet barely touched the floor, and the curved armrests cradled him like he belonged there. The oversized mirror framed him with bright bulbs that exaggerated every hint of softness in his face. It was impossible not to feel girly.

Jessica stood behind him, resting her hands on the back of his chair as she met his eyes in the mirror. "Good," she said with a little smile that was not kind. "Let’s begin."