Sissy Training Center Chapter 2: Orientation

Story by Ralan165 on SoFurry

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#2 of Sissy Training Center

After being prepped, Jamie gets to go through the wonderful orientation of his new school/home. Learning of all the career paths good sissies like him can partake in, as well as a tour of what Sweet Tammy Caretakers has to offer!

A second story in a series commissioned by JamieKaboom. I hope you enjoy!


Jamie sank his head into his shoulders. Everyone he arrived with, like him, had been forced to wear these girly outfits and no doubt had their dicks locked up. Judging by how some of them walked, it wasn't exactly comfortable for them. It took Jamie a few steps to get used to it, and he had to get used to it quickly. The guard pushing him forward wouldn't let him rest.

They entered a small auditorium with a podium on stage. Franny, or Fran as she preferred to call herself, stepped up behind it and smiled. The guard roughly grabbed the mouse by his collar. "Take a seat." He growled with joyful aggression. Tim took a spot next to him, the tiger's eye leering all around them.

"This is pretty fucked up, Pinkie." He whispered. Jamie nodded but said nothing. Preferring to keep his head down during this whole process. It was bad enough he was sent someplace with actual criminals. Why his mother sent him here Jamie couldn't understand. He'd have to call her, next chance he got.

"Attention," Franny said, clearing her throat and tapping the mic, "Is this thing on? Do I need to give it a spanking?" The doe giggled, "Sorry, just a little STC humor for all you newcomers. We like to have fun here."

The crowd erupted in jeers. "Fuck off! Give me back my clothes you bitch! Unlock my cock!" Were among the many threats thrown about. Jamie sank into his seat, eyeing the guards and taking note of their smiles as they fondled their batons. Peering back to the stage, he saw the doe pull out a remote and press a button.

Electricity surged through his collar. Through every collar. Boys screamed, some falling from their seats as they fruitlessly grasped for their collars. The mouse's fingers dug into the cushioned armrests, biting his lips and praying for the pain to subside.

"I hope you'll take this lesson to heart," Franny said, pressing the button again, relieving them of the shocks, "But a good sissy doesn't speak out of turn." Jamie gasped for air, tears in his eyes. The tiger next to him had fallen over. The doberman guard from before had picked him up, locking his hands behind him and whispering something just out of Jamie's hearing. Whatever she said, it had Tim sit upright.

"Now, I'm sure you're all wondering what we do here and why you're here. Well, let me get the second out of the way first. Each and every one of you has failed to contribute to society. Some of you may argue that society failed you, but you have no right to argue behind these walls." The doe dangled the remote in her hands to quell any rebuttals, "As such, you have been sent here, to Sweet Tammy Caretakers, to be reintegrated into society as something anyone could make use of: A good sissy."

That word again. Even after Auntie Irene's explanation, the pink furred mouse still had no idea what they were talking about. He looked around, trying to see if any of the other prisoners here knew what she meant. Confusion and anger swept through them all, and the female doberman guard stared back at him with a smile that had his fur stand on end.

"As for what we do here, well," With a clap of her hands, a screen displayed behind her. The initials STC appeared in bright pink, "We aren't some hack facility that puts you in a dress and calls it a day. Oh no. We have three levels of training for our students. Based on what your benefactors have purchased, some of you will only experience one year or training, while others will experience all three years of what Sweet Tammy Caretakers has to offer."

Three years?! Jamie sank deeper into his seat, looking over to his fellow classmates and finding the same looks of shock, disgust, and anger across their faces. The tiger beside him was practically gritting his teeth, shaking in rage. The doberman guard behind them placed her hands on both his shoulders and softly whispered, "Don't ruin your makeup, tubby." The tiger relaxed, darting his eyes in embarrassment at the nickname as Franny continued.

"First-year courses are generally the most packed, but that's because they cover the basics." She said. Images of feminine furs appeared behind him, some pictures showing what looked like ladies, and others showing chastity locked boys. The most shocking to Jamie was how similar they all looked. "You'll be learning basics such as clothing, makeup, posture, pronunciation, and sexual skills befitting a sissy." The doe explained, a new slide showing for each category, "After which, if your benefactors only requested one year, you'll be reintroduced into society as a sissy. You'll still be leading a full life and potentially even allowed to make your own choices. That is of course if you still want to. Good sissies don't worry about such matters."

The next slide had five numbers, each with a different category with the fifth one being three question marks. "Second and Third years get specialized courses. Second years will be put into one of the four categories selected based either on first-year performance or request on their benefactors. You will be spending your second year mastering every skill related to your specialized path, and your third year will be spent in the field of said path. If you do not meet the satisfaction of our field testers, you will be sent back a year to relearn. Failing again has...well I think it's better to discuss later. As for the courses." She let the slides move forward. Jamie kept watching, wishing to turn away but unable from his fear.

A picture of a fennec fox with cream-colored fur dressed in a black french maid outfit, giving a curtsey while carrying a small and reserved smile across her, well, his face, "First we have the classic sissy maid. On top of your regular sissy training, you will be expected to be masters of caring for your master or mistress's home and their wellbeing. From cleaning, cooking, childcare, and other physical tasks required to make sure your betters always return to a place of peace and harmony. Of course, the maid has many challenges, such as keeping themselves clean and tidy as well as movement in restrictive gear. Though at Sweet Tammy Caretakers, we have expectations that you'll keep a floor shiny even with your arms bound behind you."

A cat dressed in a deep red dress suit and glasses appeared on the next slide. "Next specialty is the Sissy Assistant. Usually, they provide work as personal assistants or secretaries, and are expected to be useful in the professional field." Several slides slipped past, each depicting the cat doing various acts of office work, "It's the most mentally demanding task of a sissy. But of course, it has your usual sissy requirements like any other," The final slide showed the cat on his knees, skirt up to expose the cage between his legs giving a blowjob to some sort of CEO. The crowd murmured in disgust, but a quick little jiggle of the button had them stop. Jamie reached for his collar in preparation, not that it'd stop the shocks.

The next slide showed a poodle dressed in a fine black silk dress, her fluff trimmed immaculately, and legs leaning like a model. "The trophy wife is a popular option. In this course not only will your make-up and wardrobe skills be tested greatly, but you will become masters of high-class etiquette and praise. While other trophy wives get by on their good looks, you will be a step above them by not embarrassing your master for eating the main dish with a salad fork."

A trashy bun filled the next slide, "Then there's the pleasure hole. Commonly used as a street whore or even a fuckhole to be passed around at parties, these sissies are the top when it comes to giving pleasure. No order is too demeaning, and no cock too big for these skilled individuals. Some of which are so well trained, that their customers don't even realize their hooker doesn't have a pussy. Some of you might have run into them." Fran giggled, "Though don't worry about your fragile sexuality. For a sissy, you have no sexuality. Just want your dominant demands of you."

This was all too much. Jamie had to leave, to escape from this place. In a panic, he stepped up from his chair. A heavy hand grabbed his shoulder from behind, pulling him back down against the seat cushion. "Where are you going, cutie?" A feminine voice whispered from behind. Chills up his spine, the pink mouse couldn't turn his head to face the speaker. She leaned into him, breasts against his head while whispering, "Scared? I wouldn't be. You seem like someone who will grow to love what's in store for them. And, if you're lucky," her hand brushed his cheek, slowly crawling down his face to cradle his chin and force him to look up at the smiling doberman above him, "Someone here might grow fond of you."

He gulped, but Jamie's throat froze in fear. This wasn't right. He didn't belong here. Fran clapped on her end, "Well that's the end of our little PowerPoint. I must say that I'm happy with how big our first year class is this time. We'll actually get rotating schedules! How fun." She said, spreading her arms as though she expected applause. When none came, the doe sighed and cleared her throat, "Anyway, you'll all be split into class groups and be taken on a tour by your teachers. I wouldn't try anything funny, as everyone here has access to your collar amongst other methods of control."

A pink leather leash latched onto Jamie's collar from behind. "Get up little sissy," the doberman said, attaching a new link to Tim and down the line until ten or so furs were attached. In this little chain gang, the mouse noticed the bunny from earlier, still bound and mouth lodged with that red ballgag, scowling at the guards in distaste. A sharp tug lifted Jamie up from his seat. He reached for the leash in a panic, but the guard slapped his hands away. "Ah, ah, ah. A little warning, mousie." She said, patting his head gently so not to ruin the headfur style, "Touching the leash like that could have dire consequences. And as cute as it would be to lock your arms in a sleeve, it's more fun to see the little nervous ticks you make with them."

Every word she spoke carried a warm tone that kept chilling the poor mouse. He nodded slowly, keeping his hands to his sides as she led the conga line of crossdressed boys down the halls, side by side other lines led by the guards and staff dressed in the same pink business suits as Franny.

The doberman pulled them along to what looked to be a classroom. A chalkboard, teacher's desk, and even a closet to hang bags. The student desks however had ankle and wrist cuffs latched to them and strange helmets with visors hung from the ceiling above them. "Here's your main classroom, cuties. The lovely 3B." She said, waving her arm around to show it off, "In here we'll be going over basics of sissy knowledge and reinforcing that knowledge. I'm sure some of you will take kindly more to it than others, but that's why we have special tools to help you stay in line. And don't worry, this is still technically a school, so some days we'll focus on teaching things such as mathematics, literature, science, and even theatre. I think this year we'll be doing Hairspray."

"Psst, Pinkie." Tim whispered, "Take a look at those helmets." Jamie looked at them, confused to what their purpose was. The tiger already had an idea, "I think that's some sort of brainwashing device. These sick fucks are gonna mess with our minds. We need to get-"

Another tug at the leash cut them off, "Is there something you'd like to share with the class, Jamie?" The doberman asked.

Jamie shook his head, ears furled and eyeing the floor, "N-No...Miss..."

"Darling, sweetie." She said, hooking a finger under his chin and forcing him up to those deep blue eyes, "Denise Darling. And don't like the tough little security outfit scare you, they haven't sent me my new uniform yet."

"N-new uniform?"

She nodded, "Normally at STC they have a teaching staff ready for new arrivals. But it seems the teacher assigned to your class had been chosen for a new purpose and needed to be adjusted. I jumped at the chance of promotion, and now here I am, your new teacher."

Judging by the sudden pull Jamie felt from behind, Tim stood in attention at the news. Peering over his shoulder, the mouse saw the tiger's face turn white, eyes shifting back and forth while the doberman continued to smile, petting the pink mouse's scalp once again. "Now, we still have a few stops to make. Let's get moving."

Next on their list was a wide gymnasium, missing any stands or basketball hoops normally presented. The floor didn't even have any court markings, as if left unfinished. "This is where a lot of your physical training will take place. Things like walking, posture, and flexibility are key in this room. Of course, we'll also have an exercise regimen to keep you sissies as fit as a fiddle. Can't have sissies tire out too easily can we?"

"You gonna make us cheerleaders?" Someone asked from the back. Everyone, even Jamie, turned around to the weasel at the end, who smiled awkwardly and hung his head. Jamie felt the single phrase emanating off of everyone's stare. Two words: Shut up.

Denise laughed, "We don't have a sports team, so cheerleading isn't on the agenda. To do that we'd need actual athletes and sissies aren't athletes. Though if a client requests it, I'm sure at least one of you will be holding pom-poms in the future."

"You'd have to cut off my hands first," Tim muttered. Jamie wasn't so sure they wouldn't.

Throughout their tour, Jamie noticed not only other tour groups but other furs dressed like them. Except they were walking freely around the campus, some with smiles, others with looks of boredom or stress. As if they were actually in classes. Like Jamie, they each had a tag on their ear, but they were different colors. Hesitantly, he raised his hand. "M-miss Darling?"

That wide smile at her name made the collar around his neck feel oh so tighter, "Yes, dear Jamie?"

"Why are some..students walking freely?" He asked. The words 'stupid' and 'dumbass' heckled in hushed whispers from behind him. The mouse wanted to crawl up and die again, but his curiosity took hold.

The doberman rested her hand on his shoulder, "Excellent question, Jamie." She said with praise, "You see, despite the leashes and collars, students do have a little freedom around this campus. A sissy who can't function without orders is just dead weight after all. Once you have proven yourselves, you'll be given free access to travel around the facility, with doors you have access to opening freely at your presence. This freedom does have consequences, however, as you'll be responsible for arriving on time for classes. Tardiness will not be tolerated in my class, and I'd hate to put the lesson on hold to give a spanking." With how she smiled, Jamie believed she wouldn't hate that at all.

"H-how will they open?" He asked.

Booping his nose, Denise chuckled, "With Auntie Irene's magic of course."

The bunny behind Tim muttered something, but his gag made it all but incomprehensible to understand. Reading the sign on their next stop, they had reached the mess hall/canteen. Opening the wide doors, the boys were greeted to chairs bolted to the floors with wrist and leg cuffs attached. But that wasn't what caught Jamie's attention and everyone else's ire. No, what caught that were the phallic instruments propped upright in front of the chairs.

"Gaining and keeping the sissy figure is challenging work." Denise said, walking up to the chairs and tugging the line of crossdressed prisoners along, "Not only do we need to instill proper exercise, but a good diet is required. Thankfully here at STC, we found a way to keep your training up while feeding you." Leaning against one of the machines in front of the chairs, she gripped the phallic tool and flopped it around, showing off its elasticity, "This tube delivers a special yogurt, but you need to treat it properly to get it out. And just underneath it," Her hand reached down to a fake fleshy slit underneath the cock-like tool, "Is a liquid dispenser, which requires a little pressure to get it going. You'll find buttons on your chair to extend the tools forward."

Jamie wasn't a fool. He could tell what she meant by 'treating it properly' when it came to getting the yogurt. He decided to keep his mouth shut on the matter. Tim did not. "I ain't sucking cock to get food!" The tiger roared, stepping up and dragging Jamie and some other boys with him by their latched leashes. "You can't make me."

With a single beep, all their collars turned on. Volts passed through Jamie's system. Crying out, he fell to his knees, reaching for the collar in vain. Then it stopped, and Denise's eerie chuckle emerged, "Of course we can, silly. If we discover you haven't been eating your assigned portions, then we'll personally feed you. But don't worry, soon it'll become second nature to you all. For some," She winked at Tim, "It already is."

Confused as to what she meant, Jamie turned and saw Tim gritting his teeth and avoid her gaze, staring down at the floor in shame. "Well, that concludes the basics of our tour." The doberman said, helping the bound and gagged bunny stand as the rest got up, "We'll finish our day with your final medical examination and then you sissies get some free time in your rooms. We're not monsters after all. Sissies need to be somewhat autonomous."

No one argued back, not even Tim. They knew that any more lip would lead to another shock, no matter who said it. Jamie could already feel eyes staring forward, glaring with anger. But he knew it wasn't meant for him. Just the tiger behind him.

The rest of the facility they got to see felt almost like an actual school. Sure it lacked lockers, but it had the same squeaky floors and crushing feeling of cement walls surrounding them. By the end of the corridor, however, it felt like something out of science fiction. The walls were immaculate and chrome, with pink hearts dotting the walls. Two broad guards stood at the entrance of a sliding door, like statues of muscle. Denise latched her class against nearby hooks, and unlocked the fur at the end first, passing him off to one guard. Jamie bit his lip watching the fur dragged behind those sliding doors, eyes unable to catch a glimpse of what went beyond them.

Denise leaned up against the wall beside him, "You know, I think you have the cutest face when you're nervous." She said, pinching his cheeks while he stood frozen. "I'm sure others will love seeing it."

"W-why are you doing this?" He whimpered.

Her warm smile didn't fill him with confidence. "Because it makes me happy. Isn't that what we should want in a career?" The door buzzed. Grabbing his leash, she pulled him along to the white room with a gynecologist chair in the middle. Legs freezing up, Jamie felt the urge to run. But the last boy who did any resisting had been bound and gagged the entire trip, and even if he had failed to protect himself before now, Jamie didn't want to be robbed of the option.

"Subject: Jamie Knox. Please remove clothing for examination." The disembodied voice of Auntie Irene asked. Gulping, Jamie did as instructed, stripping down until the only 'clothing' he wore was the cage locking his cock and the restraints bound to him. Taking him by the collar, Denise locked him into the chair. Arms and legs spread, the mouse tried hiding his head in embarrassment.

"There it is," Denise softly growled, running a finger through his headfur, "That lovely embarrassed look. Makes me want to keep you. We'll have to see how that goes."

Auntie Irene spoke before he could think to respond, "Sissy body assessment test start." Robotic hands on metal tendrils slithered from the walls, just like the shower. "Nipple stimulation begin." Two gloved and cold hands rubbed against his nipples. He gasped, struggling in his bonds, he mewled at the groping of his hardening nipples, the hands twisting, pinching, and rubbing them relentlessly. Denise's chuckled from the sideline, watching with interest as he struggled to even beg for relief.

"Nipple sensitivity, above average. Possible rewardable erogenous zone." Auntie Irene said aloud, "Next, gag reflex test." Another tendril came from the wall, the end tip replaced with a black and rubber lick rounded rod instead of a hand. Closing his maw, the mouse swayed his head back and forth. The mechanized hands grabbed his head, forcing his maw open while keeping him steady. The tendril sank past his tongue. He gagged, his body trying to expel the horrible thing from his throat.

"Gag reflex strong. Requires extra training to suppress. Testing for capacity." The tube inside him expanded, filling his mouth like a balloon. "Oral capacity struggling. Requires update when gag reflex is suppressed." Auntie Irene said, shrinking the tool and pulling it out. Jamie sputtered and coughed, gasping for air.

Something wet and cold brushed against his pucker. Yelping, the mouse tried and failed to move his exposed ass away from whatever was touching it. "Anal sensitivity test prep complete. Commencing anal sensitivity test."

"A-anal what? No, no, no..." he cried out, legs shaking in his restraints. This wasn't happening. This couldn't be happening. He'd never even thought about sticking anything up there. Nothing should go up there!

Denise's warm hands clamored up against his face, "Aww, don't worry Sissy. Technically, you'll still be a virgin after this." She said, shoving her chest against his face before he could cry out. "Auntie Irene doesn't count after all."

The plug pushed into his ass. Unable to push it out, the meager mouse froze, trying to breathe between the suffocation of the doberman's breasts. Back and forth it went, his dick twitching inside the cage as though he was being jacked off without even being erect. Only to keep hitting a wall as the pleasure built and built. "Anal sensitivity: High." Auntie Irene said.

"Oh? Sensitive little butt?" Denise cooed, "Sounds like fun."

"Test anal capacity." The plug inflated inside him. He screamed, the sound muffled by her tits while he struggled fruitlessly. "Below average capacity." Auntie Irene said, shrinking the plug back down and pulling out of him, leaving the mouse gapingly empty for a few seconds.

"So we have room for improvement? Oh what fun." the guard said, giving the mouse a chance to breathe. Gasping the air, tears in his eyes, he softly cried. Denise wiped his tears away and undid his restraints, "Don't cry, Jamie. It's all over."

But it wasn't over. He knew he'd be stuck here for months, if not a year. Helping him get dressed, Denise pulled him back out and walked him along the corridors of the campus. "Your classmates are already in their dorm rooms. And I think you should know, you took it better than everyone else." He sniffed, unsure of what to make from her praises. "I mean, don't get me wrong, I do enjoy a good struggle, but you were like a cute little bound angel in there. You might be my favorite student, a class pet even. Oh but I shouldn't get too attached. This is my first year being a full-fledged teacher after all."

Another door slid open. Denise unhooked his leash and pushed him inside, waving happily. "Toodles. I'll see you two bright and early tomorrow morning."

When the doors closed, Jamie looked around. The room was pink. Painfully pink with mixtures of other light and girly colors, the darkest of which was a warm purple. Stuffed animals with attachments to their crotches were laying on the bed, as well as a certain angry tiger boy with his arms crossed and headful stylized into pigtails. Tim smiled at the sight of Jamie, "Hello, Pinkie."

Shakingly standing, the mouse cowered under Tim's shadow as the tiger stepped up and over him. His roommate had tossed aside their girly uniform, except for the skirt. "Seems you got the bitch's attention."

"I'm sorry." He said, not even sure what he was apologizing for. "I'm sorry."

"Sorry?" Tim smiled, another evil smile not unlike Denise, "Nah, Pinkie. That's perfect. Means we can abuse that."

"Abuse it?"

He nodded, grabbing Jamie by the ear and pushing him against the second bed, face first into the crotch of a stuffed animal, "Yeah. Means that we can use you to keep her distracted. Get you nice and deep so that we can take her out from behind." The mouse didn't struggle against his roommate's grip, shivering and closing his eyes to forget everything that happened. "We're gonna escape this hellhole, Pinky. And you're our ace."