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Judgement Day: Barry's Cheer
🕑 Added 2025-01-23 14:00:07 +0000 UTC 
Dr. Lilith's Retreat
Judgement Day: Barry's Cheer
Barry could hear the scrape of chairs across the old wooden floor in the auditorium hall. He stood backstage, dressed in an absurd Red and gold cheerleader uniform. His bare legs wrapped in sparkling tights up to a pleated skirt that barely covered his ass and caged cock which were wrapped in frilly panties picked out for him by Mistress May this morning. His top was tight, hugging the artificial curves created by his waist cincher and bra stuffed with silicone falsies, intentionally glued a bit to the outside of center so that when they were stuffed into his pushup bra, it forced the flesh of his chest to create a crease of cleavage.
His makeup was full glam with glossy pink lips, pink and blue eyeshadow, absurdly long false lashes, and a long blond wig pulled back in a sporty headband.
As the shuffling in the hall slowed, he tightened his grip on the pom-poms in his hands. This was it, his moment of truth. Orientation day scared the hell out of him. He didn’t know if Dr. Lilith’s mad science formula was real or not but she could do enough damage with a scalpel alone. Barry was determined not to wake up dickless like in the video. Since that first day, he had tried to do what was asked of him. Licking cunt was easy enough, but sucking cock had made him vomit, leading to shocks and lost points, getting ass-fucked was almost as bad, and in the end, he had only cobbled through his “sissy week” with four points.
Desperate, he had begged Marcy for some way to save himself, some form of “extra credit.” She had agreed to talk to Dr. Lilith, only if he would wait in the guard’s quarters where they would take turns with his mouth and ass.
By the time Marcy returned hours later, Barry was bent over the arm of a couch with one guard’s cock in his mouth, his skirt around his waist and another guard’s cock in his ass. Those hours had earned him 8 more points, one for every load of cum he had received.
“I suggested a way that you could earn extra credit and Dr. Lilith agreed!” Marcy announced brightly as she walked beside Barry who was walking gingerly to protect his dripping sore ass. “Tomorrow morning, I am going to teach you one of my old cheer routines from college and then you can perform it for the staff as your evaluation!”
“Cheer routines?” Barry said doubtfully.
“Easy peasy! Shake your ass, bounce your tits and step through the choreography!” Marcy bounced in front of Barry and began chanting a cheer while moving her body through a complex set of motions.
Barry could feel his cock ache as it strained against its metal constraints. Marcy was so fucking hot, and he had been caged all week.
“I'll wake you before dawn!” Mercy Said as she left Barry at his dorm room.
She was good for her word, rousing Barry at 5am. She wore a skin-tight spandex outfit but handed him a skimpy cheer uniform. She led Barry out to the lawn overlooking the valley and then stepped him through the humiliating routine.
Where she was fluid and flawless, Barry was hesitant and choppy. She always knew what was next and Barry kept stopping to think. They ran it through until the sun was up, repeating the cheer and the moves again and again. Finally, it was time to report for breakfast. She gave Barry permission to dine in his cheer outfit rather than the usual school-girl uniform and then let him spend the rest of the morning rehearsing on his own in the square as he watched Nate, Dan, Timmy and Josh go to the building that housed Dr. Lilith’s office and the clinic one by one. So far, none of them have come out. At last he felt the painful low level triple zap from his cock-cage that told him that he was being summoned.
Marcy led him to the backstage area and told him to wait to be called, and that is where he stood listening.
At last he heard steps climb the stairs to the stage and then Marcy’s voice. “As you know, Britta finished Sissy week with the second lowest score, given the decisions that we have already made today, it would be unfair to subject her to anything less than complete feminization”
Barry gritted his teeth when he heard this. Some, maybe all of the men who had arrived with him were already downstairs waiting to lose their dicks.
Marcy continued, “Britta, I think, knew where she stood and had approached me looking for a way to salvage her manhood. After a long discussion with the Doctor, we decided to give her that chance. As you know, aside from Dr. Lilith, I am the only other CIS woman on staff. As a little girl, I got involved in cheerleading when I was nine and was an all-star by the time I graduated. This morning, I showed Britta a basic routine and I invite all of you to judge her based on her skill!”
There was a smattering of applause.
“But” Marcy said. “Before you judge Britta, you will need to know how it’s supposed to work!”
To Barry’s horror, he heard Marcy recite the chant as she bounced through the moves lightly without effort. Maybe performing alone in a vacuum, he could have convinced the crowd that he knew what he was doing, but now, following Marcy’s flawless dance, Barry would look like a clumsy butcher.
Sweat was beading on Barry’s forehead and under his wig when Marcy finished and she called “Britta! You’re up!”
Barry took a deep breath and walked out from behind the curtains. The hall held more people than Barry had anticipated. The front row was filled with women Barry had never seen before of various ages and one older man. Dr. Lilith sat in the center of the second row. On either side were the other instructors, May, June, Stephanie, and Marcy, plus many of the guards who had taken their turns on Barry the night before. The third row was occupied by women in scrubs and lab coats, the medical staff who would be turning him into a girl if he failed.
“You may begin Britta” Dr. Lilith’s hard voice instructed.
Taking a deep breath, Barry took his starting position, and then began to move through the cheer, fluid, bouncy and “fun” the way Marcy had instructed while he cried out his chant.
“We Don’t Deserve, To Keep our dicks!” He crossed the pompoms in front of his crotch and flashed a false surprise look at the audience then flicked his hair. “Take our cocks and make us Chicks!” He continued the memorized phrase that he had repeated at the top of his lungs again and again as staff and other subjects moved past him in the central square. “Give me a P! Give me a U! Give me a S and another S! Add on a Y and what do I get?” He went down into a crouch and stuck out one leg and then another in rapid succession on each syllable. “Pussy! I get a Pussy! Give me a P.U.S.S.Y and big tits!” He rose up straight, bouncing up and down as he repeated. “Give me a Pussy! Take off my wenie! Give me a Pussy and big tits!” He repeated this three more times and then finished bent over, arms crossed toward the floor, cleavage on display on the last “Big Tits”
He was met with giggles but no applause. “Thank you Britta, Please wait in my office for our decision” Dr. Lilith said as Stephanie mounted the stage and led Barry out of the room.
Alone in Dr. Lilith’s office, Barry squirmed. The glue holding his falsies in place was getting loose due to the sweat of the day. He was careful not to disturb them as he sat in the wooden chair across from the large oak desk. He noticed gouges in the wood on both arms and was studying them when the door opened.
Dr. Lilith, May and June walked in. The two assistants took up positions behind Barry while Dr. Lilith went behind her desk and opened the folder laying there. “You certainly put in the effort Miss Britta.” Dr. Lilith said.
Barry bit his lip and swallowed.
Dr. Lilith continued. “We had quite the discussion after you left.” She had not yet even looked at him as she turned through the pages. “Some of the sponsors were even willing to let you go.”
Barry leaned forward in anticipation.
“Seeing as you were a field recruit and not a sponsored guest, the ultimate decision however, lies with me.” She closed the folder and looked up at him. She held his gaze for a long time. “I can’t decide one way or the other, so I think you will remain in between.” She waved her hand.
Barry found his voice. “In between?” he asked. “What does that..” He felt a sharp pain in his neck and felt like he was sinking into his chair.
“You will understand when you wake.”
Britta looked out at the line of new guests standing shoulder to shoulder in the main square of the compound across from the clinic. Each of the newly arrived men tugged at the hem of their cheer skirts or shifted their stance, still uncomfortable and sore from the newly applied and demonstrated shock-cages on their cocks. She remembered the agony of the cage and understood better than most how powerful a motivator it could be. She looked in the mirror, glossed her lips, and then pushed her DD tits together making sure they were well displayed in her skin-tight, low cut catsuit. Down below, she grinned at the bulging outline of her uncaged and intact cock in the black shimmering fabric.
“Showtime” she said to herself as she picked up the cage-remote, clipped it to her belt and strode outside.
“Sissies!” She announced. “I am Britta, your cheer instructor! You will listen and learn from me!”
“What the fuck is that?!” sneered at the ugly one at the end.
Britta quickly tapped the sissy’s image on the remote and slid the slider up watching with satisfaction as they collapsed in a high-pitched squeal of agony. Britta strode over the tormented sissy, stuck her thumb under her waist band and pulled her leggings down. Her cock flopped out, large and growing hard. Tormenting sissies was always a turn on for Britta.
She kicked the sissy and barked “Get on your knees and look at it!” She showed the remote for emphasis.
The sissy got up to her knees, eye level with Britta’s rising phallus.
“THAT! Is my state of the art, scientifically enhanced girl dick!” Britta barked. “Kiss it!”
The sissy looked up at Britta with disgust and horror.
Britta thumbed the control and the sissy fell over again.
She waited for the sissy to get back to her knees. “Now you need to suck it!” She demanded. Usually blow-job training doesn’t start till day 3 but this Sissy needed to be broken early and Britta needed a release. She locked eyes with the next Sissy in line and grinned as she felt the fallen Sissy’s lips close around her shaft. “Mmmm… she knows how to suck a dick!” She scanned the other horrified sissies.
“I earned this dick by learning my cheers! DO YOU UNDERSTAND?!” She waited. The sissies all nodded. “Cocksucker, fondle my balls!” She yelled. She felt the sissy’s hand come up and then flatten against Britta’s crotch. “Oh right,” she went on. “They're gone!” She looked down at the Sissy who had frozen. “Keep sucking! Use your tongue more!” She then looked at the rest of the horrified class. “I lost my balls and earned these tits by NOT DOING WHAT I WAS TOLD! Is that clear?” The standing sissies cringed and stepped back a second as they nodded. “Good! Oooh… Hold on.”
Britta gripped the wig of the sissy on her knees and pulled her face against her, forcing her cock down the sissy’s throat as she felt a faint pulse and a little dribble combined with an electric surge of pleasure through her entire body. “Oh GOD!” she gasped. She pushed the sissy off and onto her back and looked down at her wet dick. A droplet of clear liquid emerged from the tip.
“Estrogen,” She explained. “I only get a dribble now, but the full body orgasm is fantastic!” She pulled her leggings back up pressing her damp cock against her belly. “Now, to keep functioning, I have to work that out every day, so I’m lucky that I have you all!” She took a step back.
“Ok, girls, let's begin!”
