by John Dylena
Nothing could prepare him for what came next.
Ms. Kilia gently slid the head of the dick into his ass, then thrust forward all the way to the hilt. Tyler cried out as he rocked forward. His right arm gave out and he fell onto his elbow.
She pulled the dick out slowly, then thrust in again. If it weren’t for the inflatable plug that had stretched out his insides, he would’ve been in agony.
Ms. Kilia moaned as she thrust her hips backward and forward, the dildo inside of her moving her toward a second orgasm. Tyler’s grunts turned to moans as she fucked him relentlessly, her pace constant.
His hips and legs hit the desk with each thrust, and the antique piece of furniture moved slightly. Tyler grabbed the edges of the desk, his knuckles white from the force of the grip. He was bent over at a right angle and his face rested on the smooth wooden surface.
“Scream for me, Tiffany!” she demanded, slapping his ass.
“Ohhhh!” Tyler cried out, his voice high and feminine.
“Oh god, you’re such a whore! Come on, beg!”
“Please… please fuck me, Mistress.” He let go of the desk and lifted his chest off of it with his elbows. His jaw hung slack and his tongue flopped around his pretty pink lips.
“Louder, slut!” She slapped him again.
“Fuck me, Mistress! I’m such a slut!” Tyler could feel the orgasm building up inside of him. His dick fought to be free from the cage, but the plastic held firm. He swelled up inside of it, longing for release.
Ms. Kilia pulled out of his ass and turned him around. Tyler’s body moved on its own and he climbed up onto the desk. She lifted his legs into the air and he fell onto his back. Only a couple seconds passed before her dick was once again pounding his ass.
Tyler moaned loudly as she fucked him relentlessly. The desk rocked like a boat until she cried out once more. His own climax was delayed from the constricting chastity cage, but the front of his panties was completely soaked. He breathed heavily as Ms. Kilia’s thrusts grew weaker and slower until she stopped all together.
Both parties were exhausted and breathing heavily, but there was one more thing left.
“Up on your feet.”
Tyler slowly climbed off of the desk and stood by her. He didn’t even smile when she produced the little key to his cage.
“I see you enjoyed yourself,” she said noticing his soaking wet panties.
She pulled aside the soiled undergarments and unlocked the cage. Tyler’s dick sprung to life, hardening instantly.
“Kneel.”
“Yes, Mistress,” he said, obeying her command.
“I’m sure you would like to finally cum.”
“I would, Mistress.”
“Well, I will allow it, but only if you cum on my heels and lick it up.”
She leaned against the desk and slid her foot toward him. Her black patent heels reflected the white lights of the classroom. He wanted so badly to cum—to release the potent arousal that had been building up inside— but he would have to lick it off of her shoe.
Ah, fuck it. I’ve already gone this far. Who the hell cares anymore?
Tyler lifted up the front of his skirt and grabbed his dick. He eagerly stroked it, and it wasn’t long before he was about ready to blow. Ms. Kilia moved her foot right up to him and he aimed his cock at her. Seconds later, white-hot cum erupted from his tip and blanketed her stocking and heel. He jerked forward, the milky-white fluid jetting out of him in bursts until at long last, his balls were empty and the soothing post-orgasm chemicals flooded his brain.
It was the best orgasm he had ever had. But it was not over yet.
Knowing what he had to do, he bent down and licked his cum from her heel. The salty, sticky treat wasn’t as bad as he thought it would be, and after several good licks, her foot was clean.
“Good girl, Tiffany,” Ms. Kilia said as she removed the double-ended dildo from her vagina. Tyler watched her lick her own fluids off of the dildo as she removed the harness. He waited patiently for her to remove the clothes he had on.
She hummed to herself as she put her belongings into the suitcase and zipped it closed. Tyler stood there confused as she put her skirt back on and walked away from the desk toward the door, wheeling her suitcase behind her. Tyler was still in the outfit she made him wear. His eyes went wide when she grabbed the black trash bag that contained his clothes and unlocked the door.
“Wait! Ms. Kilia!”
“Don’t worry, Tyler. You’ve earned that A.”
“But—”
“See ya next week!” She smiled as she walked out the door, leaving him with nothing but his backpack and the slutty costume he still wore. He looked back at the whiteboard and the text scribbled all over it. My name is Tiffany, and I’m a naughty girl.
“Son of a bitch!”
UP ON THE STAGE
The night was young, and Scott sat mumbling to himself in a booth.
He had only been in the bar for an hour, yet he hadn’t had anything to drink. The beautiful raven-haired waitress walked up to his table again, and once more he sent her away. The first couple of times she came by wearing a smile, but her eagerness to serve him, whether genuine or not, had since vanished.
He didn’t even look at her when she came this time. His eyes remained on the women up on stage, the one in the schoolgirl outfit in particular. The waitress—whose name was Amy… or Alice? He couldn’t remember and he didn’t care—glared at him as she asked if he wanted anything to drink.
She didn’t even wait for him to say “no” before leaving and moving on to the table next to him. Her happy waitress persona reappeared as she greeted the other patrons. The men seated there were tipsy and tipping well.
Scott stared at the women on stage, his eyes focused on their sensual movements and slutty outfits. Any straight man would be turned on, but for some reason it wasn’t working for him. It probably had something to do with the rut he was in.
For the past year, Scott had worked for a shitty company and barely made enough to survive. The company had recently downsized, and in the process, he was laid off.
Now with no income, he wouldn’t be able to keep his cramped, one-bedroom apartment. A blessing and a curse, he thought, realizing that he wouldn’t have to deal with the shoddy living conditions anymore. If he didn’t find a new job soon, however, he would be homeless.
“These dancers are terrible, and the wait staff is horrible,” he muttered as he placed his forehead on the table and sighed.
There was a voice in front of him. “Oh yeah? Well, it isn’t easy.”
Scott lifted his head off of the table. Standing before him were two of the strippers. One was the woman in the schoolgirl outfit he’d had his eyes on earlier. Their arms were folded under their breasts they glared daggers at him.
The color from Scott’s face vanished when he realized that his thought hadn’t stayed in his mind, but oozed out of his mouth with distaste. Any rational and sober man would have apologized and kept his thoughts to himself, but Scott wasn’t in a rational mood, and despite being as sober as a saint, he opened his mouth once more.
“You just go up there in your slutty costumes and move your bodies to the music. It’s not hard.”
His eyes went from the blonde schoolgirl to the busty brunette wearing a bikini that looked like it was made from a disco ball.
“If it’s so easy, why don’t you get up there and show us how it’s done?”
“Hell no! Why would I do that?”
The brunette said nothing and smiled when the big burly man walked up next to her. Scott recognized him as one of the bouncers who was built like a brick wall. At 6’5” and 260 pounds, he could easily have doubled as a UFC fighter when he wasn’t bouncing strip clubs.
His voice was deep and rough. “Is this man bothering you, ladies?” he asked the two women.
“Yes, Roger. We’d like for you to kick this asshole out of the club.”
The man chuckled as he reached acros
s the table toward Scott and a look of pure terror crept onto his face.
Scott was never a big guy. He was thin and lanky, and Roger could easily have snapped him like a twig if he wanted to. He struggled, trying to get away from the hulk, but he had nowhere to go. The man grabbed him, his massive hand wrapped around Scott’s arm.
His struggle drew the attention of those around him who watched for a moment, but the other patrons’ attention quickly returned to either the women on stage or on their laps. There was always someone getting thrown out of the club, so seeing Roger grab a man and pull him out of the booth was nothing special.
The blonde woman followed Roger and Scott out the side door into the alleyway next to the building. It was dimly lit, the only illumination coming from the small yellow light above the dancers’ entrance.
Roger held Scott against the brick wall with the schoolgirl stripper standing next to him.
“So, here’s what’s going to happen,” she began. “You’re either going to come backstage with me and spend the rest of the night as a dancer and waitress, or Roger here will send you to the hospital with broken bones and bruises.”
“You’re fucking serious, aren’t you?” Scott groaned.
She nodded. “I am.”
He looked again at Roger, considering his options. On one hand, stripping and parading around like a slut taking orders would be absolutely humiliating. His gorge rose as he thought of it and every cell in his body urged him against this course of action.
On the other hand, Roger was massive. He didn’t doubt for a moment that he was capable of breaking his face, or any other bone he pleased. Clearly he’d pissed off the strippers enough that any appeal to their sense of decency would go unheard, and since Roger gleefully answered to them, he doubted if the burly bouncer would show any hesitation before bashing his skull in.
Humiliation, or untold amounts of pain? Talk about a rock and a hard place…
In the end, Roger begrudgingly chose the lesser of the two evils. The last thing he needed was to add extensive hospital bills to his pile of debt.
“Fuck it. Okay!” he shouted. “Just please get this guy off of me.”
“Roger, take him backstage.”
The man smiled and shoved Scott toward the dancers’ entrance. The woman opened the door and smiled. “Oh, my name is Bree, by the way.”
“Scott,” he spat.
Bree turned and walked ahead. Scott’s eyes were glued to her body. It was hard to look elsewhere. Her high heels, long legs and miniskirt had him hypnotized.
The walls of the hallway were clean but barren with a couple doors leading to other rooms. At the end of the hallway was a large locker and dressing room. One of the walls was lined with mirrors and lights.
Underneath the mirrors were many small vanity tables. Makeup and accessories of all kinds were strewn across the surfaces. Personal storage lockers were against the second wall. There were couches and chairs, large laundry baskets for dirty clothes and a massive wardrobe full of various costumes, lingerie, wigs, and everything else a stripper might need to get dressed.
There were several girls chatting as they quickly changed into different outfits. Silence filled the changing room when Scott was brought in.
“Umm, what’s going on, Bree?” one of the ladies asked.
“Yeah, who is this?” another chimed in.
Bree smiled. “This is the man that Allie was complaining about. Not only that, but Kerri and I overheard him saying how poorly we were dancing. When we confronted him about it, he said it was easy and all you had to do was ‘put on a slutty outfit and move your body.’ ”
The women stared at Scott. He could feel them disemboweling him with their eyes. “For the rest of the night, he will be dancing and waiting tables,” Bree finished.
The dancers erupted in laughter. “So we can…?”
“Yes. Dress him up. Give him an outfit, wig and makeup,” Bree said.
“She needs a name first.”
“Well, his name is Scott,” Bree said.
“How about Sapphire?” one of the women said. “Goes with his eyes.” Scott watched as the women talked amongst themselves, then nodded at Bree.
“He’s all yours, ladies,” she said. “I have to get back on the floor.”
Scott screamed as the women pounced on him. In seconds, he was standing in the middle of the room, naked.
“Eww, look at all that hair!” one of the strippers said, sticking out her tongue in distaste.
The women led him to the shower where they handed him a disposable razor and shaving cream. He lathered up his body and shaved his arms and legs while the women eagerly watched.
“Everywhere, Sapphire,” one of them said, pointing to his crotch. Scott watched his body hair fall off his body when the hot water came. He stepped out of the shower, his skin smooth and hairless. It felt weird, but he knew he shouldn’t complain. Roger was just a whistle away, after all.
A woman handed him a towel, and he dried off and they pulled him back into the changing room.
“He’s pretty skinny. That makes this easier, at least.”
“The only problem is he’s got no breasts.”
“Easy fix. I’m sure we have some breast forms somewhere. Slide them in and add some makeup around the edges to make it blend.”
“Becca, you’re a genius!”
“What about his hips and waist? He doesn’t have a single curve anywhere.”
There were a million conversations going on at once. Each woman was examining Scott, and they all had their own ideas for what he should wear. They eventually all agreed on an outfit and look. Because this was supposed to be a punishment, they went with something especially slutty and revealing. One of the women handed Scott a black thong.
“We don’t have all night!” she said as he hesitated.
He slowly put it on and pulled it up, stopping the moment the back hit his cheeks. One of the women behind him reached out and pulled the strings up, forcing the strap into his crack.
Following the thong were black fishnets. Scott sat down on one of the chairs and two of the women helped him put them on. When he sat down, the thong went deeper into his crack and the discomfort was written all over his face. He felt like it was splitting his balls.
“Like that, don’t ya?” one of the women teased. Scott didn’t answer. What he wanted to say to her would likely get his ass kicked.
They stood him up and handed him the next piece: a bright red leather miniskirt. It was nothing more than a piece of fabric wrapped in a tube shape. He pulled it up to his hips and looked down. The hem stopped halfway down his thigh. It had a slit in it, giving his legs more room to maneuver, but making it easier to see what was underneath too. All he had to do was bend over and the world would see his junk. The same woman who pulled up his thong pulled the straps out higher so they came out from underneath his skirt.
“That’s so the men can tip you,” she giggled.
They gave him the next piece: a red bikini top. They tied it behind him and stuffed in the breast forms, giving him cleavage that amounted to something slightly larger than an A-cup. Then they led him over to one of the empty desks and sat him in one of the chairs.
With the lights on his face and his reflection in the mirror in front of him, he watched them decorate his face with makeup. The women applied everything they could think if. They painted his lips red and used dark eye shadow; mascara, eyeliner, blush, lip gloss—anything they could get their hands on.
As they painted his face, two women glued acrylics to his nails. With the makeup done, they gave him a brunette wig with shiny, luxurious locks that cascaded past his shoulders.
Scott said nothing the entire time, watching in horror and awe as they turned him into a woman. I look so sexy. I can’t believe this is what I look like.
When they finished with his hair and makeup, they gave him jewelery and accessories: a leather choker to hide his Adam’s apple, gold clip-on hoop earrings, bracelets
, perfume and a liberal smattering of body glitter.
Then came the last part of the outfit: his heels. They sat him down and brought forth the finishing touch: five-inch, clear-soled stripper heels with an ankle strap. They put the shoes on him and stood him up.
“Give us a twirl.”
Scott turned, staggering a little as he presented his final look to the ladies. They replied with eager screams and laughter as they patted themselves on the back.
One of the women pointed at Scott’s crotch. “Oh my god, ladies—look!”
Scott looked down to see his hardening dick poking against the miniskirt. His face flushed. No… seriously?!
The stripper grinned as she addressed her compatriots again. “He’s getting turned on by this!”
Scott moved his hands in front of the skirt to hide the bulge, but it was no use. Everyone in that room had seen his growing arousal.
I…I don’t understand. Why am I getting turned on by this? Why am I getting a hard-on from being dressed up like a woman?!
“What’s the matter, Sapphire? Seeing yourself dressed like this got you turned on?”
“No! It’s not that…” he replied. “It’s your outfits.”
“Right,” Becca said. “You sure it’s not your outfit that’s getting that little guy all excited?”
The women moved in closer, completely surrounding him. They whispered playfully in his ears while touching him all over. His heart was racing. His mouth was dry, and he was twitching with anxious energy as he tried to resist his growing arousal. He looked down and watched as one of them grabbed his hand and placed it on his crotch.
“Go ahead, Sapphire. Play with it.”
He swallowed as he lifted up the hem of the miniskirt. His penis was so rigid that it shot up once he pulled aside the fabric. The thong provided no resistance against his boner.
He bit his lip as his fingers grabbed his shaft. Never before had he been so against satisfying himself, yet he wanted to so badly. His hand slowly shifted up and down as the women watched and urged him further.