No one was surprised Timmy ended up in prison at the young age of eighteen. He had always been a hell raiser. The real surprise is how long it took society to finally lock him up. Somehow, he had avoided juvey while all his juvenile delinquent friends were making their rounds. Somehow the law had missed Timmy even though he had been almost going out of his way to get himself locked up. It was as if Timmy actually wanted to go to prison, at least subconsciously. Timmy wanted to be a real gangster and it was hard for a street punk to get the props he needed with some prison time on his resume. Timmy didn't realize he wasn't cut out for prison though. He was a pretty white boy who thought he was a lot tougher than he actually was. Probably more than half the problems in Timmy's life came from him trying to prove that he wasn't the soft delicate white boy he looked like on the outside. Timmy was about to learn a hard reality the hardest way possible.
It started on Timmy's very first day inside. He was standing in reception in formation with the other prisoners. The others were all hardened convicts covered in tats and scars. Not only could you see their hardness, you could feel it, and Timmy felt something else in addition. He could feel their eyes crawling over his body the way his would crawl over the female form when he was free and out running the streets. Even the guards had gleams in their eyes, though theirs were probably more for Timmy's entertainment value than any actual lust, except for maybe that select few. Timmy knew he had to do something quick to prove himself; otherwise, these animals would eat him alive and worse. He thought opportunity was presenting itself in the form of a female correctional officer. She was the only female guard on duty and had been eyeing him the entire time like she was judging him almost the way the other convicts were. It had been making Timmy feel very uncomfortable. She was attractive enough. On the streets Timmy would have more than welcomed her stare, but that almost made it worse. He knew in the joint, any courtesy shown towards a guard could be misconstrued to mean various things, none that worked in his favor and all could infer weakness. When the female guard approached Timmy, instead of turning on the charm like he would have done on the streets, he did the exact opposite.
"I run a program for younger guys who might not be ready for the hard realities of prison life," she informed him with a badly concealed whisper. "I can probably get you in it if you're interested. It will keep you safe."
"Are you crazy, bitch? I'm not some punk ass bitch. I don't need some special program." It was much easier for him to attack her when he knew how she saw him, like some little kid who needed protection. Did she think she was his mother or something? He glared at her, his eyes spitting venom in their contempt. It took her less than a second to respond back to him. Timmy's attitude was an act; hers was the real thing. She might not have been as hard as the convicts or the other male guards, but she was a whole lot harder than poor Timmy. She followed up her poisonous stare with a hard loud stinging slap across Timmy's face. Before Timmy had time to recover from the initial shock of her slap, she reached down and grabbed his groin. She squeezed a handful of nut sack, and held Timmy's balls tight in a vice grip. She squeezed and pulled down until Timmy was on his knees, screaming, crying and begging for mercy.
"Please, please, stop! Let me go!"
"You disrespect me when I'm trying to do you a solid?"
"Owe it hurts! I'm sorry! I'm sorry!"
"Not as sorry as you're going to be, sweetheart," she told him. She loosened her grip just enough to relax the more excruciating part of the pain, but that only made it worse. It allowed Timmy to become aware of his surroundings. He heard the laughter, howling and hoots of both guards and hardened convicts.
"Strip," was the next order Timmy heard the female officer bark at him! Oh God, no, Timmy thought! But before he even had a chance to disobey, she once again increased the pressure of her grip on his nut sack until it was unbearable. Timmy howled out in agony and this created more laughter, a ruckus. It wasn't long before Timmy surrendered. He quickly began unbuttoning his shirt, taking it off, kicking off his shoes and pulling off his socks...
"Pants and panties too," she ordered emphasizing the word 'panties' to an increased volume of audience laughter. Timmy would have been mortified if the pain his balls were enduring had been light enough to permit it. He allowed her to readjust her grip from one hand to the other as he worked around her and pull off his pants and underpants. When he was completely naked, she directed him to get up off his knees and stand. Without letting go of his package, she guided him to the front of the room and had him turn around to face the formation of hardened convicts.
"We'll watch the boys strip for us from here," she said to him loudly enough for everyone to hear. Then as the guards directed all the hardcore convicts to strip, she began stroking his cock. "Nice isn't it?"
Timmy wouldn't answer. Of course her hand felt great but not under these conditions in front of a group of drooling killer convicts with him under her complete control like her pet monkey or something.
"Would you rather I continue hurting you some more," she asked, angrily squeezing Timmy's nut sack to remind him of the difference. Timmy cried out. He shook his head that he didn't want that.
"Yes," Timmy said.
"'Yes', what?" she asked.
"It feels good."
"You're welcome," she said. "Nice show, too, isn't it?" She asked him nodding in the direction of the hard convicts stripping down naked. Timmy's face dropped. He realized what she was doing and what she was trying to make him say.
"Say it," she demanded, guiding him with a slightly, tighter squeeze to his package.
"Nice show," Timmy sobbed, realizing it sounded like he was talking about the formation of convicts stripping and showing off their hard bodies and semi-hard to fully hard cocks. Some of the convicts smiled at him, one even blew him a kiss. He quickly looked away and at her and she smirked.
