After Sheba pumped her spunk into Timmy's suck hole and had him swallow her load, she shaved him smooth and hairless like a woman should be. She then dressed him up in a patchwork of lacy lingerie similar to the way Madonna used to dress when she started her career. She even put a bow in his hair and had him put on the lacy fingerless elbow length gloves. A lacy garter held his fishnet stockings thigh high for a nice sexy effect. There was no need for a skirt or panties. They wouldn't be on long enough for the bother.
When Sheba walked him back out and reintroduced him to Kong and his crew of gangsters, no one could believe their eyes. No longer could anyone possibly think of Timmy as a man. That wasn't even an option. The only thing that even hinted of masculinity about him was his hard little two inch pecker shamelessly pointing straight ahead like it was telling him which way to go. It danced around like a little puppet whenever he would take a step. There was no sign of male left in Timmy's appearance except for that little thing and that didn't really matter to anyone except maybe Timmy. Timmy had been transformed into a pretty girl. Granted he was a flat chested, shapeless girl, but lots of pretty little prison girls were that way until some big strong prison daddy decided to start feeding them hormones or inject them with silicon in all the appropriate places. Timmy was soft, smooth and pretty with a delicate fragile body and that was what mattered in the beginning. Everyone was speechless, even Johnny for once. Johnny kind of stared with a mixture of shock and lust. Then Sheba introduced Timmy with the announcement of his new name.
"Meet Tiffany, everyone. We'll call her Tiffy for short," Sheba said. It made Johnny snort out a laugh and mimic the name. It made Timmy/Tiffany put her head down in shame. Kong approached her and took her chin gently in his hand. He lifted her head and forced her to look up into his eyes.
"Is that little white monkey bothering you, Tiffy darling?"
Tiffany rolled her eyes sideways at Johnny who nervously backed up and stared in disbelief. "Maybe a little," she said with a shrug.
Kong let go of Tiffany's chin and stomped over to Johnny. "Get over against the cell wall and stand in the corner."
"Are you serious?"
"Either stand in the corner with your pointy nose stuck to the wall or Sheba is going to take you into the back and fix you up nice and pretty so you can join us."
"I... I'll just leave, okay?" Johnny asked.
"No, it's not okay. You have two choices. Pick one."
Johnny hustled over to the corner of the cell and pressed his nose into it.
"That's right, boy. Press your nose right up against it. And close those fucking eyes and keep them shut. You know the drill, boy! Don't make me take off my belt!" Kong reached for his belt and Johnny trembled. Kong turned back to Tiffany with a wink. "Is that better, baby?"
Tiffany wasn't sure how to answer.
"Of course it is," Sheba cut in, wrapping her arms around Tiffany and licking her ear. She was actually cutting Tiffany off before she could answer to make sure she said the correct things. "I'll bet she wants to thank you for getting rid of that annoying little shit but doesn't know how. You can just give him a little 'thank you', baby. That's all Daddy needs."
Sheba smiled at Tiffany and Tiffany took the hint. Tiffany glanced at Kong, "Thank you, Daddy."
"That's alright, Princess. I'm sure you'll be showing me how grateful you are in a few minutes here."
Tiffany looked to Sheba for guidance. Sheba slid down Tiffany's torso to her knees and took Tiffany in her mouth. Tiffany gasped. She thought for a moment Sheba was about to return the favor Tiffany had done for her in the rear cell moments ago. She was, actually, in her own way, just not yet. Sheba brought Tiffany to the edge only. Then she wrapped a piece of twine tightly around the base of Tiffany's cock before she could cum. In addition to making her unable to cum, it kept her hard without the possibility of going soft.
"This will keep you right on edge. We heard about you and that female officer and Daddy doesn't want you cumming too quickly."
Tiffany heard Kong behind her. He was unfastening and unzipping his pants. She heard the material drop to the floor. She watched the pants slide forward past her feet as Kong kicked out of them and scooted them out of the way. Tiffany started to turn her head to glance back over her shoulder and get a good look at Kong's cock, but Sheba popped up and grabbed her face and kept her looking straight ahead.
"Don't," Sheba warned. "If you see it before you've had it, you'll be too afraid to take it and it will make the pain worse. Just look at me and lean backwards. That's right, just like that. You're doing great."
Tiffany felt it now. It felt like someone was trying to force a baseball bat up her tight asshole. She started to scream and Sheba slapped her face. Sheba grabbed Kong's pants from off the floor and pulled his belt through his pants loop. She folded it and put it in Tiffany's mouth and told her to bite down. Tiffany did. Sheba reached around her and grabbed both her ass cheeks and spread them apart as wide as she could. She pushed her back down onto Kong's cock. The pain was excruciating. Tiffany felt as if she were being split in two.
"Remember, don't look back and keep biting down," Sheba warned. Then she disappeared back down to her knees and between Tiffany's legs. She took Tiffany back into her mouth sucking and licking and lapping. She was an expert; Tiffany felt that. As good as she was though Tiffany couldn't cum because of the cock ring of twine wrapped tightly around the base of her little hard on. This kept her on edge and horny and wanting to fuck. Unfortunately, those feelings didn't overpower the excruciating pain of Kong's monster cock going deeper and deeper into her asshole and spreading her ass cheeks and hips wider and wider apart. She bit down hard on the leather in her mouth and felt the wet tears rolling down her cheeks. Her asshole burned like someone had fired up a blow torch and was using that to fuck her with. She imagined the head of Kong's cock all the way up inside her belly. It felt like it wasn't going to stop until it rode up through her throat and poked its head up out of her mouth. She felt his big hairy balls, one under each ass cheek and almost as big, and then...
Then the pain stopped.
Tiffany couldn't hide her sweet surprise so everyone knew what had happened. She had been blacked, turned out, emasculated and feminized by the master of prison sissy slut creators. Her asshole had been turned into a pussy for all intent and purposes and she accepted that. Sheba came up smiling and kissed her on the mouth. "Are you alright, baby?"
Sheba already knew the answer, but felt compelled to ask anyway. Tiffany confused, submissive and dreamy eyed, nodded. Kong grasped her hips and began sliding her up and down his fat hard meaty fuck pole until Tiffany's asshole began making wet, sloppy, squishy sounds like a used and abused hooker's snatch that had been working all night without a shower. Tiffany was no longer in pain. She had fallen in lust, love possibly, but definitely lust. The only thing keeping her from cumming was the twine wrapped around the base of her lady-cock sissy-clit. Her cock was twitching crazily, trying to cum, but failing. She had a case of "the cum shooting dry heaves". She was dizzy, euphoric and ready to faint from the pleasure of being on edge too long.
Sheba went back down and took her back in her mouth and started sucking. She released the twine, and Tiffany had an intense orgasm and flooded her mouth with cum. Sheba kept sucking until Tiffany's balls were contracting and aching from being drained dry. Then she climbed back up Tiffany's torso and sealed her lips over Tiffany's. Sheba hadn't swallowed. She flooded Tiffany's mouth with Tiffany's own spunk. Almost at the same time, Tiffany felt Kong filling her up with hot steamy spunk deep inside her bowels. His cum burned and stung because of the damage his huge HGH mutated cock had done to her insides, but it felt good too.