by John Dylena
“From now on, until I unlock that door and set you free, you belong to me. You’ll address me only as ‘Mistress.’ Failure to do so will earn punishment. Do you understand, Tiffany?”
He grimaced at name. It was bad enough that she was going to dress him like a slutty schoolgirl, but did she have to give him such a girly name? “Yes, Mistress.”
“Good girl,” she replied. “Now stand up and take off all your clothes.”
Tyler gulped as he did as he was told to do. He obediently took off his shirt, jeans, shoes, and socks and set them on the desk.
“Those too,” Ms. Kilia said, pointing to his boxers.
His face turned red as he slid the solid-colored boxers down past his ass, to his knees, and finally to his ankles. The cold air of the classroom touched his naked body and he felt goosebumps on his arms and legs.
Ms. Kilia stuffed his clothes into a black trash bag and set it down by the door alongside his backpack. When she returned, she picked up the pink collar that she’d left on the desk next to him and wrapped it around his neck.
The collar was tight, and a shiny gold heart shaped tag dangled from the front of it. Etched into the metallic surface in a cursive font was the name “Tiffany.” Ms. Kilia grabbed his hand and led him to the desk where all the items were laid out for him.
“Sit on the desk and spread your legs.”
“Yes, Mistress.”
He climbed up onto the desk and opened his legs, exposing his flaccid cock. The desk was cold and prickled his bare ass. Tyler said nothing as he watched her play with his dick for a moment before locking it away in the clear chastity cage. He grunted as she slid it over his shaft. It was tight, but not too tight.
“So thin, and with barely any body hair! I lucked out,” she said with a devilish smile. “Now, put these on, Tiffany.”
Ms. Kilia handed him the white lace panties and he hesitantly took them from her. He held the dainty garment in his hands, his fingers stroking the soft, sheer fabric that would soon cover his groin.
Tyler paused, and he was rewarded with the sharp sting of her riding crop. Almost fumbling the panties, he froze when she placed the rubber tip of the crop under his chin.
“Pick up the pace, Tiffany. I don’t have all day.”
“Yes, Mistress,” he whimpered.
Tyler looked down at his feet as he stepped into the panties. He pulled them up past his knees until they were snug on his groin. His dick pulsed, and the fear of getting turned on by this grew in his mind.
The panties were light and delicate; he could barely feel them on him. There was a decorative floral pattern in the design, and the bra that she handed him had a matching pattern.
He slipped his hands into the straps and Ms. Kilia tucked her crop under her arm as she walked behind him to fasten the clips. The cups of the bra deflated against his flat chest, but that was quickly remedied with the insertion of some balled up socks that filled the B-cup bra.
Unlike the panties, it was hard to ignore the bra, and he felt the warmness in his body gather at his groin as Ms. Kilia led him to the large wooden desk and gestured for him to sit up on it. Tyler watched her roll up the snow-white stockings into a donut and slowly slide them up past his feet. The thin, stretchy material caressed his legs like a second skin.
He bit his lip as he watched her put the stockings on him. With each item added, he grew more and more aroused.
When she finished with the stockings, Ms. Kilia handed him the tiny pleated skirt. Tyler stepped into it and pulled it up to his waist, then buttoned the two round, flat buttons on the side. The pleats jutted out, and the tops of his stockings were clearly visible. This outfit was obviously designed for either a stripper, or as part of a sexy Halloween “costume.”
After the skirt came the blouse. The thin white top had sleeves that went just past his elbow and had large cuffs that were folded over. He started to button the blouse, but she slapped his hands away from the silver buttons.
“Unbutton the top two, leave the last one buttoned, and tie the bottom.”
This is ridiculous, he thought, but only said: “Yes, Mistress.”
He unbuttoned the top, and thanks to the stuffed bra, his blouse opened wide. The bottom half was tied in a knot, showing off his bare belly. She sat him back down on the desk and slipped the five-inch heels onto his feet.
The bright pink shoes reflected the white lights of the classroom, and thanks to the stockings, they slid onto his feet effortlessly. Ms. Kilia buckled the tiny strap and helped him back onto his feet.
“Walk up and down the aisle, one foot in front of the other.”
“Yes, Mistress.”
He turned and walked away from her. His movements were slow, and he extended his arms out to his sides as he tried to maintain his balance. Walking became a chore, and he tried his best not to fall.
“Move your hips, slut! Show off that ass of yours.” Ms. Kilia walked parallel down the row next to him, her eyes focused on him. She barked orders at him like a drill instructor. “Arms at your sides, hands flat, fingers pointing outward!”
Tyler lost track of how many times she made him walk up and down the column of desks. With each pass, he felt his movements get smoother and walking in the heels became easier. His hips swayed back and forth and he pulled his shoulders back, forcing his chest—and imaginary breasts—outward.
“Looking good, slut! Now, sit down at the front middle desk. Time for your makeup.”
“Yes, Mistress,” he said as he scurried to the desk.
“Cross your legs!” she said, hitting the top of the desk with her crop. Tyler crossed his legs in the feminine fashion and watched as she placed her portable makeup kit on the desk and bent down in front of him. He said nothing as she transformed his face.
Much like the hair on his body, Tyler had very little on his face. He could go a year without shaving, and at the end of the twelve months, there would be nothing but stubble. The hair on his head was short and thick, but his eyebrows were thin in comparison.
She applied plenty of makeup to his face, hiding any blemishes and imperfections with foundation and concealer. Then she moved to his eyes and used a dark, earthy color for eye shadow. Mascara followed, and she finished with bright pink lipstick—a color that matched his shoes and skirt—and topped it off with a shiny coat of gloss.
“Perfect lips for sucking cock, don’t you think, Tiffany?”
“Yes, Mistress,” he whimpered. Tyler dreaded having to walk, talk, and act like this. But there was nothing he could do. Ms. Kilia was tenured and very good friends with the dean. Not only that, but who would even believe his story? If he went around telling people that she dressed him like a slutty schoolgirl, it would only make matters worse.
“Pucker those lips for me,” she said. Tyler mimicked her and she smiled. “Perfect. Almost done.”
Ms. Kilia dug around her suitcase and came back with a handful of costume jewelry. She clipped gold hoop earrings to his ears and glued a piercing to his belly button. In addition to the temporary piercings were a couple of dangly bracelets and a rhinestone anklet.
She had him bend over the desk, and he felt the cold, wet application of a temporary tattoo. The tramp stamp that she gave him was nothing more than the word “slut” with a tribal pattern. Ms. Kilia was going all out for this. He half expected her to produce a futuristic voice changer.
The final addition to his transformation was the layered brunette wig. It was styled, and once she put it on his head, the makeover was complete. Ms. Kilia handed him a small hand mirror and he took in his new appearance.
“Like it, Tiffany?”
“I… I can’t believe that this is me, Mistress. I look so—”
“Girly? I know. It’s as if it was meant to be.” She swiped the mirror from him and put it back in the suitcase along with the makeup. “Now the fun begins. From now on, you must talk like the slutty schoolgirl that you are, understand?”
“Yes, Mistr—” He jumped when
he felt the sharp sting of her crop. I forgot she had that. “Yes, Mistress,” he said again in his best female voice.
“Good girl. Now, sit back down.”
Tyler returned to his desk and faced her. He crossed his legs and waited patiently.
“Tiffany, you are here in detention why?”
“Because I’ve been bad.”
She slapped her crop on his desk.
“Because, Mistress, I’ve been, like, a bad girl,” he said again, trying to talk like a bimbo schoolgirl.
“Yes you have, Tiffany. And now you need to get punished. Stand up and bend over.”
“Yes, Mistress.” Tyler placed his hands on the desk and his back to her. He could hear her walking around behind him, but he couldn’t see what she was doing. She lifted up his skirt and exposed his panty-clad ass.
“Bad girls get spanked,” she whispered softly into his ear and he yelped when her hand made contact with his rear. The sting lingered for a moment, but before it could fade, she smacked his ass again. “Tell me you’ve been a bad girl.”
“I’ve been a bad girl, Mistress.”
She slapped his ass. “Again.”
“I’ve been a bad girl, Mistress.”
Another smack. “If you want to get an A, you have to play along.”
Tyler swallowed. “I’ve been, like, a bad girl, Mistress. I need to be punished.”
Ms. Kilia pulled down his panties and rubbed his now red cheeks. “Still not convinced,” she said, slapping him once more.
“Please punish me,” Tyler cried. “I’ve been a naughty girl!”
He waited for another slap, but it didn’t come. Instead, he felt the cold application of lube around his asshole.
Oh shit.
He remembered seeing the inflatable butt plug as one of the items she pulled out of her suitcase. Looking over his shoulder at her, he saw Ms. Kilia grin as she held up the black toy. He looked away and prepared for the inevitable insertion.
Tyler gritted his teeth and groaned as Ms. Kilia slid the rubber plug into his tight asshole. She didn’t slide it in all at once; instead, she pulled it out and pushed it in deeper; two steps forward, one step back. It was tight and awkward, but the foreign object managed to inch its way into his rectum until his sphincter swallowed the last bit. The flared tip kept it in his ass.
She pulled his panties back over his still red cheeks, the hose for the pump hanging out through one of the leg holes.
With a playful slap and a rub, she ordered him to straighten back up. Tyler did so unwillingly, forcing his back into an odd curve. The toy in his ass rubbed his insides with every little movement he made.
“Now, Tiffany, I want you to go up to the whiteboard and write: ‘My name is Tiffany, and I’m a naughty girl.’ Use any color marker you like.”
“Yes, Mistress.” He took a step forward and grimaced, the plug was right up against his prostate, making his dick throb inside its plastic cage. God damn it, why is this turning me on?!
Tyler’s gait was stiff. His body moved like he was incredibly sore. His trek was only made worse by Ms. Kilia’s riding crop. It repeatedly struck his ass as she urged him to move faster.
“What’s the matter, slut? Never had a dick in your ass before?” Tyler said nothing as he grabbed the marker and walked up to the whiteboard.
“Legs together, ass out!” Ms. Kilia commanded. She sat on the desk and watched him like a hawk as he wrote the first sentence on the top left corner of the whiteboard. She reminded him of her presence with the occasional whipping.
“You call that handwriting? Erase and start again. You write like a man. Dot your I’s with hearts and throw some curves in there!”
“Yes, Mistress,” Tyler said, wiping away the sentence with the black Styrofoam eraser. He cursed her under his breath and cringed as he wrote each sentence and dotted the I’s with little hearts. The process got easier with time, but an unfortunate side effect was that he was repeating it over and over in his head as he wrote it.
My name is Tiffany, and I’m a naughty girl.
He bent his knees and squatted in order to write the last couple of sentences for the first row, only his action earned him a couple strikes.
“Bend at the waist, not the knees. Stick that ass out.”
Tyler stood back up and bent over. He felt the toy in his ass swell up and he looked back at Ms. Kilia. She had the football-shaped pump in her hand and a cruel smirk on her face as she squeezed it again. The plug expanded and stretched the lining of his rectum. He said nothing as he returned to his sentences.
My name is Tiffany, and I’m a naughty girl.
Only a third of the board was filled with the sentences. He sighed as he straightened back up and moved further down the whiteboard. Tyler lifted the marker up and started with the second row, and removed ‘detention’ when it got in his way.
Halfway through the second column, Tyler could no longer stand still. He squirmed as he wrote the words, his stocking-clad legs rubbing together and he gripped the hem of his micro-skirt with his free hand. Biting his lip didn’t help to dull the arousal that was building up inside of him. His dick throbbed more and more often as the toy rubbed his insides, and Ms. Kilia inflating it only exacerbated the situation.
He covered his mouth as he moaned, and a dollop of cum oozed out of his imprisoned dick into the lacy panties.
Ms. Kilia snickered behind him. “Is my little slut getting all wet between the knees? Are you getting off on this, Tiffany?”
Tyler said nothing as he tried to recover from the sexual ordeal. No release came from the ejaculation; no relief from the erotic tension that was building up inside of him. He returned to writing the sentences and hoped that this would be the end of it.
He was wrong.
When Tyler finally covered the entirety of the whiteboard with his girly handwriting, he realized that his punishment was only just beginning. He set the marker down on the tray triumphantly and turned toward Ms. Kilia. The movement was so quick that his skirt flared up and exposed his panties. Anyone with eyes quick enough would’ve noticed the wet patch on the front.
She smiled and quickly glanced at the writing on the wall. “Very good, Tiffany. Looks like you’ve earned a reward.”
Tyler’s smile grew wider as he watched Ms. Kilia remove her gray skirt. She unzipped it, and he realized that she wasn’t wearing any panties.
The smile on his face vanished when she turned around and grabbed the double-ended strap-on. Fear and arousal fought for dominance inside his mind as he watched her step into the harness and insert one of the ends into her pussy. She moaned as it slid into her, and Tyler’s heart raced in his chest. Ms. Kilia exhaled and adjusted the straps.
“I don’t know, Tiffany—would a slutty girl like you consider this a reward, or a punishment?” While waiting for his reply, she playfully stroked it. “Well? On your knees, slut.”
Tyler once again hesitated. It took three whips from her crop to get him moving.
He whimpered as he got down on his knees and came face-to-face with Ms. Kilia’s dildo. It was a silicone replica similar to the phallus that he had locked away between his legs, and much like the one he had, the dick pointed at him had a bulbous head, veins, and a pair of heavy balls that hung from the base.
Ms. Kilia pushed her hips forward, bringing the tip of the dick to Tyler’s hot pink lips. She moved it around his mouth and slid it on his cheek, teasing him. After slapping his face with it a couple times, she pressed it against his lips once more and pushed forward.
“Take it, you cock sucking slut! You want that A?”
I do want the grade… Just get this over with, Tyler.
He closed his eyes and opened his mouth. The rubbery phallus slid in and he wrapped his lips around it. She pushed it in deeper, then pulled it out. The dildo left his mouth with a pop and he took a couple deep breaths.
“Use your tongue. Show me how much you want that A.”
Tyler sighed and went to work on th
e dick in front of him. He leaned forward and stuck his tongue out, cradling the head of the dildo with his slippery appendage as he licked the tip and moved down the base to the shaft. He stroked it with his left hand as he sucked on the fake testicles that hung below it.
Ms. Kilia moaned as the other end of the dildo writhed around inside her pussy. Every bit of movement sent jolts throughout her body, and watching Tyler suck on the dildo heightened the pleasure.
He took the cock in his mouth once more and bobbed up and down on it, sliding it deeper and deeper. In no time, he was taking in the entirety of the pole, the slurps and the sucking noise filling both his and Ms. Kilia’s ears.
She gripped the desk with both hands as the Tyler picked up the pace. The faster he moved on the shaft, the quicker Ms. Kilia approached orgasm. Tyler’s own dick throbbed in its cage and he ignored the spurt of cum that leaked out into panties. He needed to get this over with as quickly as he could, and if it meant throwing his inhibitions to the wind, then so be it.
Her moans grew louder and louder until she jerked her hips forward and orgasmed. Tyler watched her knees buckle and he removed the dick from his mouth. He looked up at her and waited for her to tell him that he was free.
Unfortunately, she wasn’t done with him yet.
Ms. Kilia’s body was flushed and her breathing heavy, but she was an experienced woman and she wasn’t quite ready to throw in the towel.
“That was wonderful, Tiffany. I wonder how many men you’ve satisfied?” Tyler said nothing, his face turned bright red. “Up on your feet. Hands on the desk.”
She stepped away from the desk and watched Tyler climb to his feet. He placed his hands on the flat surface and stuck his butt out instinctively. He looked over his shoulder and watched her smile as she lifted up his skirt and pulled down his panties. She rubbed his ass, and seconds later, he felt immeasurable relief as the butt plug inside of him deflated.
He grunted as she pulled the plug out and set it aside, but his ass wouldn’t be empty for long. Tyler felt the tip of the dick press against his asshole and he knew what was next. Closing his eyes, he gritted his teeth.
