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Judgement Day: The Cuck of Jessica
🕑 Added 2025-04-28 18:46:38 +0000 UTCNone of the other sissies from Jeff’s class had come back once they were called in for their assessment. No one could tell him what to expect. This morning, Jeff had awakened in agony as the electric shock-cage around his cock surged with power.
“It’s decision day Jessica!” She had said as she held down the trigger button. She watched Jeff writhe on the bed, sheets thrown into disarray and the straps to the neglige he slept in falling off his smooth but still muscular shoulders. She let go and loomed over the bed as Jeff tried to regain his breath. When he finally looked up at him, she dropped a small key on his exposed chest. “Here!” she said. “You’re done with that cage! Either your wife will take you home, and maybe fit you with one of her own choosing or you won’t have a cock to cage anymore by tonight.”
Jeff held the key in his thumb and forefinger soaking in what Steppanie had just said.
“Exciting! Isn’t it?” She beamed before walking out of the bedroom. She returned a moment later and Jeff’s stomach turned. Stepanie held a shimmering pink dress. It had fabric roses along the bust line, a body hugging bodice, and a short skirt that flared over layers of taffeta petticoats. The hemline was also adorned with larger fabric roses. In Stephanie’s other hand she held up a pair of 5” silver strappy heels. “Look at the pretty dress your wife sent for you!” Stephanie almost sang the words.
“With all these petticoats, you won’t have to worry about a bulge, but don’t get too excited!” She hung the dress on the back of the door and set the heels on the floor before going out into the sitting area.
Jeff gingerly unlocked the cage and removed it carefully as the skin wanted to adhere to the metal. He saw two raw points where the electrode contacts had burned him. The smell wafting up was disgusting. “May I shower first, Miss Stephanie?” He asked with the most demure fem voice he could summon with his raspy morning throat.
“I insist upon it, Miss Jessica!” Stephanie called back. “Make sure to use your cream! You will want your skin silky smooth for your big day!”
Jeff pulled the spaghetti strap back to his shoulder and climbed out of bed, letting the hem of his silk negligee fall down around his thighs. He glanced once more at the dress, shook his head and passed into the bathroom. He knew better than to close the door, privacy was forbidden at the retreat. The hair removal cream needed about five minutes to soak in before being washed off, so Jeff noted the time as he began to apply it, starting with his face and working his way down his whole body. Once he could feel the tingle starting to give way to a sting, he stepped into the shower to rinse it off, soap off, shampoo, condition, and get clean. After toweling off he applied the fruit-scented body lotion to every inch so that he smelled like raspberries as he went back into his room to dress.
Knowing Stepphanie would be peaking, he carefully picked out pink silk panties with lace ruffles and a matching pink bra that would match the dress.
He was about to reach for the dress when Stephanie called, “Wait! You will need these!” and handed him a pair of white thigh-high stockings with pink roses on the top.
Jeff tried not to sigh as he fished a white garter belt out of the dresser.
“Garters under the panties!” Stephanie sang from the next room “In case a gentleman wants the goods!”
Jeff couldn’t contain the shutter as he flashed back to the last session of “Receiving” lessons the night before where he spent a good hour bent over the edge of a couch while one male guard after the next enjoyed his “boy pussy”
Almost as if she could read Jeff’s mind Stephanie walked back in holding what Jeff would have once considered an obscenely large stainless steel butt plug dripping in lube. “Like your cage, this has a kick to it, so no acting up!” she said. “Bend over!”
Jeff said nothing, turned and laid his hands and face on the bed as he felt Stephanie pull his panties down and slide the plug into his ass. He felt his sphincter close around the bulge and rest in the valley before the base, pulling it in deeper if he tensed, trying to remain relaxed, he stood back up and finished getting dressed.
The skirt covered even less than Jeff had anticipated and he could feel the wind on his ass while he clicked his heels against the sidewalk from his dorm, up the hill to the main building.
Stephanie had led him to a dressing room and told him to wait.
Nate, Timmy, Daniel, Barry, and Josh were all there too, each dressed in some ultra feminine costume or another. Assuming that the room was monitored, they sat in silence and contemplated what was to come.
Marcy came carrying a tray that held six small cups of water and six little cups of pills, setting one in front of each student. “Dr. Lilith knows you are all nervous, so this will help keep you calm.”
“I’m fine!” Timmy snapped.
“Take the pill or I’ll burn you balls off!” Marcy’s tone shifted instantly.
Each of them swallowed their pills quickly as Timmy and Marcy faced off. Marcy reached for her pocket where the control switch was. Timmy’s nerve broke and he took his pills.
One by one, Marcy would call them out. None of them came back after. Now Jeff sat alone, cross legged, one hand on top of the other on his knee like a “proper lady” as he had been instructed, and he waited, trying not to think of the massive intrusion in his ass.
Without warning, the plug began to vibrate. It started very low, almost unnoticeable but the intensity grew and Jeff shifted in his seat. It was uncomfortable, but mostly because it was pleasurable and Jeff didn’t want to admit to enjoying it. Glancing around nervously, he reached up his skirt, and pushed his penis between his legs, squeezed his thighs together and tensed his pelvic muscles trying to keep himself from having an erection. He could feel the pleasure growing still, so he bit the inside of his jaw while trying to focus on how angry he should be at Carol for sending him here. He was terrified of what kind of trouble he would get in if he were to cum in his panties right before his assessment. This had to stop, it wasn’t fair.
The door opened. “Jessica, this way please!”
Jeff stood and immediately felt his cock press against the silky fabric of his panties. He walked slowly, deliberately, to keep balance on his heels but also to try and keep everything in place. Despite that, with the humming of the plug in his ass, the motion of his steps and the slick surface of the fabric, by the time he reached the stage door, his penis had slid past the gusset of his panties and was jutting out the leg hole under his skirt. He stopped, wide legged and reached up his skirt, trying to stuff himself back in place, but he was rock-hard and would not bend. In the end he tented the panties under his erect cock, hoping to keep it pointed down. He looked up to see Marcy staring at him disapprovingly.
“I can see why so many of the girls come to appreciate being rid of that thing,” Marcy said. “Maybe you will by the end. Up the stairs and onto the stage, they will tell you what to do from there.”
Jeff gulped and climbed the steps, feeling himself slide out almost immediately. He hoped that the rose trimmed frilly skirt was puffy enough to conceal his protrusion as he stepped out from behind the blacks onto the stage and into a waiting spotlight.
He could make out shapes in the audience, nothing more. The spotlight in his eyes drowned everything else out. He did hear an immediate peal of laughter. He recognized the voice, it was Carol, she was out there and she was laughing at him. When this all began, he had signed the paperwork thinking he could save his marriage. They had told him it was couples counseling, but it was all a trap they had set with Carol’s help. The woman who he thought was his partner and best friend had betrayed him, subjected him to a week of unspeakable humiliation and violations. As she laughed he felt the plug in his ass and could taste the cum of his trainer in his mouth from the night before. They had turned him into a sissy. Something broke inside him at that moment.
He had already come to understand that the marriage was over. How could it ever continue after what Carol had done to him, but he hadn’t fully internalized or understood how much she must hate him until now, as he heard her laugh at the pink sissy he had become.
With every fiber in his being he wanted to jump down off the stage, smack her in the mouth and walk out of here. But he also knew that the pleasing hum in his ass would turn into excruciating pain the moment he stepped out of line. They would shock him, restrain him, and take him to the operating room if he dared try anything defiant.
He found his mark on the stage, curtseyed, and then struck the submissive “wait” pose his trainers had taught him all week.
“As you can see Mrs. Harris, Jessica has learned a great deal.” Dr. Lilith’s voice came from the silhouette next to the laughing one. “You should be proud to know that she has been one of our star students with the second highest score in the class.”
“Second highest?” Carol asked.
“Yes ma’am, Only Natallie surpassed Jessica in obedience and submission” Dr. Lilith replied.
“What happened to Natallie?” Carol asked.
“Natalie is going by the name Nathan again. He will be joining our staff helping to train the next batch of sissies.” Dr. Lilith said.
Jeff let out a sigh as he felt some of the tension in his chest release. There was such a thing as hope in this place. Nate made it through! But what about Dan, or Josh, or Tim? No mention of what happened to them.
“Are you a good, obedient girl Jessica?” Carol asked.
Jeff curtseyed again “As the mistress commands?” All he had to do was get Carol to take him out of this place, after that, he could make a run for it, get to safety, call the authorities and shut this place down. Just a little longer to make them believe.
“Go ahead.” Carol said.
A third silhouette rose from their seat, it was larger and masculine. It walked around to the stairs and climbed up to the stage. Jeff felt the blood drain from his face as he recognized David, his college intern. David had only been working for Jeff for a few months. Beside the fact that David used the company gym before work every day, and had the physique to match, Jeff had learned very little about him.
The younger man was half a head taller than Jeff, and broad shouldered. He had a thick black beard on his face, a ballcap with mirrored sunglasses on the brim. He was wearing a muscle shirt and baggy sweatpants which he dropped to the stage as soon as he was standing by Jeff.
“Blow me sissy!” David demanded.
Jeff looked at him in shock, then back to Carol who just tilted her head, then back to David who had placed a hand on top of Jeff’s head and was pushing him down.
No matter what happened, after this, Jeff would never command respect in the office again. Even if he fired David tomorrow, the story would get out before he was gone. The buzzing from the plug in his ass jumped in intensity and he felt a tingle between his legs that reminded him that he had no control of the situation at all. He sank to his nylon encased knees, opened his mouth and took David between his lips.
David was gentle to start, he moved his hand off Jeff’s head and let Jeff slide his mouth up and down on David’s cock at his own pace. While he did so, the buttplug started to change speed and intensity, rising to peaks and then dropping again and again, almost in rhythm with the bob of Jeff’s head on David’s cock. Jeff’s own cock was so hard it was throbbing now, surging against his skirt, he felt like it might burst!
Soon Jeff could taste drops of precum leaking from his intern onto his waiting tongue. He braced himself for the mouthful that would follow, but David pushed him back off him, cupping Jeff’s chin in his hand as strings of saliva and cum stretched from his mouth.
“Good Girl!” David said. “Now I’m ready for that boy-pussy! Are you ready?”
Jeff glanced down at the waiting silhouettes and then back up at David, then nodded.
“That’s my girl!” He said. He pushed Jeff’s chin aside roughly so that he fell onto his hands and knees, which was exactly where David wanted him.
David knelt behind Jeff, and pushed his knees apart before pulling up his skirt. “Look at this!” He announced. “This sissy is loving it!” Jeff felt David smack his balls and rock hard cock with his hand and he winced in pain as well as shame. He felt a trickle of precum dribble out of his penis down to the stage.
“She is going to have to lick that up,” Carol announced.
“Every drop!” David agreed, “mine and hers!”
Suddenly the plug in Jeff’s ass went silent. He had only an instant of relief before he felt David roughly yanking it out of him, leaving him feeling vacant and empty. That emptiness did not last as almost instantly, Jeff felt the pressure against his anus of David’s penis thrusting into him.
Jeff’s own cock twitched at the intrusion as David’s cock slid past his prostate. Jeff bit his lip to contain screams of horror and pleasure while his own subordinate fucked his ass. He tried to clench his pelvis but this just made David’s motions hurt so he let go.
As he felt David thrust in deep and hold, he also felt himself let go. His cock throbbed and a ropey white trail of cum spurt out onto the floor under him. He grunted at the first unrestrained orgasm he had felt since he arrived while David cheered and pulled out, warm fluid ran out of Jeff’s ass and down his leg.
Jeff was still panting when David came round and forced his sloppy dick into his mouth. The taste was revolting and Jeff tried to pull back but this time David’s hand was holding him firmly in place.
“Clean up time, sissy!” He announced.
Jeff had no choice but to lick and suck until he tasted nothing but skin. By then David was already hard once more. He began thrusting again, holding Jeff’s head in place while he fucked his face until Jeff felt him surge into the back of his throat once more. This time Jeff swallowed everything quickly and pulled his head back gasping, trails of cum and spit running down his face.
“Stage too!” David tapped his toe next to the pool of cum under Jeff’s cock. Without hesitation, Jeff crawled back two strides, lowered his face and lapped up his own cum. He was almost done. What more could they throw at him now? Carol had no reason not to believe Jeff would obey any command after what had just happened. He just had to clean this up and they would be going home.
“Come on back David,” Carol called.
David bowed, pulled his sweat pants back on and climbed down to take his seat.
Jeff watched him as he licked up the stage. Carol took David’s hand immediately and pulled it to her own crotch where David’s strong fingers seemed to dig into her jeans. She kissed him.
Jeff’s heart stopped. David. This was all about David.
David the kid.
David the intern.
No, David the mastermind, David the prize, David the object of Carol’s desire and the reason for her betrayal.
Carol and David.
Now Jeff knew. There was no fooling Carol. She didn’t come here to “fix” her husband. She came to swap him out for the sissy he just proved that he was. Was there still hope? Carol, plus David, plus sissy Jessica?
David had clearly shown that he would be happy with the arrangement and Carol had sent him to do it, so maybe that was the play. Maybe Jeff could survive as their sissy third until he could get out.
The stage licked clean, Jeff rose to his feet, feeling the sticky sensation of cum drying in a steady line from his ass down his right leg. He lowered his eyes and adopted the submissive pose once more.
Carol finally spoke. “Ok, she’ll do as she is told. What did you think honey? Did you like her?”
“A huge improvement from the original.” David agreed.
Jeff wanted to throttle the boy, but he held his pose. They were about to free him.
“Congratulations, Dr. Lilith.” Carol went on. “She is just as you described. I honestly cannot believe how far she has come in the past week and I really want to take her home as is since we both could make a lot of use of her.”
Jeff withheld a smile.
“But” Carol said.
Oh no! Jeff knew that “But” Whenever Carol used it, she was unwavering in the decision that followed it.
“But, she clearly enjoys this too much! I cannot have a sissy that's turned on by my man!” She said, “The whole point was to make Jeff suffer, and yet this sissy likes it up the ass so much that she blew a load all over the stage!” She sighed. “Frankly it’s pathetic and he clearly was never a straight man.”
Jeff looked down at the discarded buttplug on the floor. It looked featureless, there was no way for Carol to know that he had been edged up to the instant David entered him. “Carol” Jeff said.
“Shut up!” Carol snapped.
“But Carol!” Jeff tried again.
“Silence her!” Carol demanded.
Suddenly a pair of arms grabbed Jeff from behind and a large rubber ball-gag was shoved into his mouth. He felt it pull tight, straining his cheeks and heard the click of a lock behind him. He tried to cry out, but only a muffled moan could be heard.
Carol looked up at Jeff, then climbed the stage. She lifted Jeff’s skirt to reveal his still hard cock with a new drop of precum emerging. “The fucking sicko likes this!” She turned to Jeff and slapped him across the face before turning back to Dr. Lilith. “I have no use for his cock, take her all the way!”
“As we discussed?” Dr. Lilith asked
“Bigger!” Carol growled as she picked up her purse.
Jeff screamed into his ball gag and tried to run off the edge of the stage. There was an exit in the back of the room and no one was ready for him. He took two steps before he was seized and pulled back. He felt a sharp pain in his neck and the room spun. He tried to take another step and his knees folded. Hands caught him and lifted him to a gurney. He could see the pipes over the stage as he was rolled past the blacks and into the hall.
Light, Tile, Tile Tile, Light rolled by above him. He couldn’t move but he could see, he could hear and he could think. Oh God, would they leave him like this while they operated? He tried to ask, but his mouth wouldn’t move. He remembered the ballgag, but he couldn’t feel it. He was entirely numb.
Light, Tile, Tile, Tile, Light
There was a bang and he was passing through a set of double doors. The room was bright white, there were poles with complicated machines attached to them, then he was under a large round light hanging from an adjustable arm.
They sat him up and Dr. Lilith walked in. She ignored Jeff as she walked over to a box and pulled out a pair of latex gloves that she started putting on.
Jeff tried to look around in desperation, but he couldn’t even control the direction of his eyes.
Dr. Lilith showed Jeff the purple encased gloves she wore. “More tradition than precaution. My MACR formula negates almost all bacteria. Infection does not happen in this theater.” She motioned to someone behind Jeff.
Suddenly he saw but did not feel Stephanie and June pulling off his dress, his hose, his bra and his panties leaving him naked on the table. He was positioned looking down at his still rock hard cock, standing erect straining toward his chin. The phrase “last stand” was inappropriately funny to him.
He was scared to death, angry, and also utterly defeated. How was he so hard? This wasn’t fair! He was supposed to hate all of this! Carol wanted him to hate it and he had obliged her in every way except his damned cock! It had doomed him. It had doomed itself. He could see Dr. Lilith uncovered a tray covered in clamps, and scalpels. He had to find a way out of this but he couldn’t move. He could hardly breathe. Despite all this, his cock remained rock hard.
The realization struck him and would have knocked him over if he had any motor control. The damned pills Marcy handed out in the green room. Everyone else got white pills. Jeff didn’t notice it at the time, but his were blue!
“At this point, I wish our paralytic wasn’t so effective.” Dr. Lilith said. “I really want to know if you figured it out. The viagra before the show? The vibrator in your ass? I knew what Carol wanted and what she didn’t want.” She laid a drape down over Jeff, the rectangular hole in the paper framed his stiff penis. “You are the perfect mix of genetics, and bodytype for my non-compression formula tests.” Stephanie loaded a thick rubber band onto a device, then squeezed the handle. It opened, spreading the band into a wide circle.
Dr. Lilith continued. “You were always coming to my table Jessica. Your penis was my accomplice in betraying you. Now. Let's have it off!”
They kept Jeff awake and made him watch the whole procedure.
The elastic band closed around his scrotum, he watched his balls turn blue, then purple before Dr. Lilith cut them away with her scalpel.
“In the old days, Vaginoplasty would take hours and we’d never attempt it on a cock covered in hair like this” Dr. Lilith said.
She held Jeff’s cock and traced lines with the back of her scalpel. “We would have to cut here and here, Pull this part aside, Open this up, move this, invert that… it was a real chore” She flipped the scalpel over and almost carelessly cut Jeff’s cock free.
Stephanie was right behind with clamps and bandages to stop the profuse bleeding from the bare circle where Jeff’s penis had joined his body.
Dr. Lilith held the severed member in Jeff’s face for a moment. “Nothing but medical waste now.” She tossed it into an open stainless steel tray. “I’d weigh it for you, but you would be disappointed in the results” She moved away, leaving Jeff to watch as Stephanie continued to hold the bandage in place over the amputation site.
It was gone. Jeff was dickless. His vision blurred slightly. He may not be able to feel the liquid on his cheeks, but he knew he was crying.
“Now comes the miracle of MACR!” Dr. Lilith announced as she returned with a curved device that looked like a metal codpiece covered in black rubber circles.
“Ready!” Stephanie announced and moved back, uncovering the bloody mess for an instant of horror before Dr. Lilith fit the codpiece over Jefff’s crotch.
“Injectors” She said coldly.
One after the next, Stephainie handed her glass tubes filled with liquid with a needle on each end. Dr. Lilith pushed each needle through one of the black circles and left it in place until all 13 had been positioned.
“Three, Two, One, GO!” she said.
All 13 vials drained at once. Once they were empty, Dr. Lilith pulled them out one by one.
“Now we wait.”
Someone behind Jeff unlocked and removed his ball gag.
As the hours passed, Jeff could start to feel again. Strangely, he did not feel pain in his crotch under the metal plate. His fingers tingle, then burned then sensation returned and he could wiggle them once more. He felt the tears still running down his face and he managed to tilt his head to catch a glance of the discard tray that held his severed manhood. He reached up to wipe his tears and was surprised when he realized that he was not restrained.
“You bitch!” he sniffled with a shuddering breath
“Oh good! You’re back!” Dr. Lilith smiled. “An unintended side effect of MACR is that it negates most paralytics or anesthetics since it can heal faster than they can inhibit. If it’s rolling back your motor control, that must mean it’s all done with healing your injury!”
“You mangled me!” Jeff slured
“Not at all!” Dr. Lilith beamed. “Look for yourself!”
Jeff put his hand down on the metal plate covering his crotch, then paused for a moment. He took a deep breath and pulled it aside, bracing for the horror show underneath.
What he saw took his breath away.
There was no blood, no stump, no open wound.
Instead, there was a bare hairless slit, two labia lips pressed together. He brushed against them with his fingers and felt a tingle through his body.
“No,” he said.
“It’s quite real, and far more than cosmetic.” Dr. Lilith remarked. She loomed over him. Stephany pushed him back against the gurney and held his hands back.
Dr. Lilith put her fingers between the lips of Jeff’s labia and opened it, explaining as she went. “You now have a complete vulva. Your urethra has been rerouted automatically to the proper point. She moved on, your clitorus is of average size but it’s much more sensitive than that of a natural born woman. A request from your wife.” She moved on. “And that leads us to…, she pushed and Jeff felt the doctor’s fingers inside her in a way he had never felt before. He gasped in shock and in pleasure while his mind reeled at sensations it had never been meant to experience. “Your vagina” The doctor said, “Complete with self lubrication, G-spots, and…” she pulled her finger out and tapped on Jeff’s belly “Once your uterus and ovaries form, you will have a menstrual cycle too.”
“How” Jeff had watched the whole time.
“The same way Stephanie, or June, or May got theirs. Modified Accelerated Celular Regrowth, MACR.” She shrugged. “It started as a healing agent, but the feminization factor could never be overcome. They considered it a failure, I have other opinions.”
“You’re a monster!”
“I’m a healer Jessica!” Dr. Lilith said. “The rest of your body will catch up to your pussy over the next month or so, but your contract has you here till next spring.” She smiled. “By then you will learn to appreciate the gift I have given you.”
She turned and left while Stephanie handed Jeff a hospital gown.
