Timmy's Prison Cavity Search

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A white boy goes to prison and finds out he isn't so tough.
3.2k words
4.35
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Part 1 of the 4 part series

Updated 10/29/2022
Created 08/28/2014
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smutnut
smutnut
165 Followers

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.

"Which one do you like best?" she asked him. Timmy's blank face turned to shock and then pain as she squeezed hard once again to once again remind him who was in charge. He cried out. "You better answer me or I'm going to rip these right off and wear them around my neck."

Timmy turned around and looked. He didn't answer but his eyes fell upon and lingered on a big black muscular convict sporting a fully engorged erection. The female officer who had him by the balls called the black convict to the front of the formation to join them.

"You don't mind if my girlfriend here holds on to you while I perform a cavity search on her, do you?"

"Not at all, Ma'am?" The black convict told the female officer. The female officer turned to Timmy.

"Darling, I want you to reach into my pockets and pull out my surgical gloves and put them on for me, understand?" she asked with a squeeze. Timmy was so out of it by the sheer terror and anticipation of the unknown and threateningly guessed at going on immediately around him that she had to squeeze even again to bring him back to reality. Bring him back she did though. He reached into her pocket and pulled out the surgical gloves.

He almost started to put them on his own hands.

"Not your hands, silly. Put one on my free hand, sweetheart," she told him squeezing for emphasis as she did so. She wiggled the fingers of her free hand in the air and Timmy slipped one of the surgical gloves over that hand.

"Now, I'm going to switch hands. Don't even think of trying anything," she told Timmy.

"Don't worry, Ma'am," the black convict told the female officer. "I'll keep an eye on her."

She smiled, "Thank you so much." She released Timmy and switched hands as the black convict watched them both. He smiled at the female officer. Timmy watched the two of them nervously. He was so afraid he didn't even take offense to the black convict referring to him as a "her". Maybe he had even lacked the awareness that it had actually happened. When the female officer had the hand he had gloved on his sack, she wiggled the one he had yet to glove in the air. Timmy slid the glove over that one like he had the other before. She didn't even have to give him the squeeze. He kept glancing timidly from the female officer to the black convict.

"Bend over now and hold onto Daddy's hips while I make sure you're not trying to sneak anything into the prison that might get you in trouble," the female officer told Timmy.

Timmy couldn't believe what he was hearing. He couldn't face anyone else in the room. He wouldn't look at the female officer, or the guards or the formation of convicts watching, whispering and snickering. When Timmy looked down he saw the black convict's fat erection pointing out straight from his hips. It would be right in front of Timmy's face. He shook his head in refusal. The female officer squeezed his junk hard. He cried out but still refused her request. She kept increasing her force on his sack until Timmy couldn't bear the pain any longer. Reluctantly, slowly but surely, he bent over and grabbed hold of the black convicts hips. He came face to head, cock head that is, with the black convict's huge erection. He was so close he could kiss it and he knew the black convict would have loved nothing more than that. In fact he felt most everyone in the room would have loved that, to see him do it that is, even the female officer. There was something leaking out of the head of the black convict's pee hole and it wasn't pee, not that pee would have made anything better.

The black convict placed his hands atop Timmy's to keep him in place as the female officer switched hands so as to get a better angle on gripping Timmy's nut sack. She reached from behind and between his legs. Having him in perfect position for her cavity search, she began running her fingers up and down the insides of his ass crack, spreading his ass cheeks and poking her fingers around. She teased his little brown hole until Timmy started feeling excited against his own will. He couldn't hide the shock on his face and it made everyone laugh. He knew they knew what was happening to him. Timmy thought he was going to start weeping. Finally, the female officer formed all the fingers of her probing hand into a spear and pushed inside of Timmy. Timmy screamed out. The black convict took this moment to push his fully hard cock into Timmy's mouth and down his throat. It shocked Timmy so much that he actually stopped screaming, but only until he realized what had happened. Then he started screaming again, more frantically than before and it would have been louder if it wasn't being muffled by the black convict's cock which was also choking him. Unfortunately, this second round of screaming along with the choking was causing vibrations and massaging around the black convict's cock. It only helped increase the pleasure for the black convict. The black convict began pumping his hips to fuck Timmy's mouth the way he would a woman's pussy if he had the woman on all fours.

Timmy had never so much as looked at another man's cock before except maybe for a few stolen glances at guys in the showers at public gyms. And that was only to compare size. Yet here he was with a mouthful of thick black cock meat. He thought of biting down to make the big black convict pull his cock out of his mouth, but he was too afraid of what the convict might do. Instead, when the big black convict told him to use his tongue, he tried his best to do so. The black convict wasn't happy with his efforts so he slapped him in the head and told him more tongue. It felt impossible. Timmy's mouth was so full of hot black meat that he had no room to move his tongue at all. Yet somehow he managed to move it just enough to start lapping around the warm dark meat stretching his mouth as it jammed in and out of his throat, getting bigger and bigger as it did so. When the black convict pulled back just so much leaving just the fat swollen mushroom head of his black monster cock just inside Timmy's mouth and told him to roll his tongue around it and around it and tease his pee-hole with the tip of his tongue, Timmy did what he was told. He received a mouthful of hot bitter pre-cum for his efforts. The black convict didn't stop there. He told Timmy to play with his big black hairy swollen balls and Timmy reached up and began doing so.

Timmy felt the female officer probing deep inside his asshole, fingertips rubbing over his prostate as she moved in and out, fucking him like her fingertips were the head of a cock. Timmy's ass ring stretched tightly around her wrist and sometimes even around her forearm as she pushed in deeper and deeper. He was mortified at the sensation she was creating in him - hopefully it was she. Her actions started giving him a painful erection. It was clearly visible to all. He heard the formation of convicts watching commenting on it. The shame was overwhelming but he kept sucking the big black cock and he even started humping back on the female officer's pumping arm like he had no control over his own actions. It was like he was deep in lust, and disgusting more so than he had ever been with any girlfriend he had ever been with in his straight normal life when he was free on the streets outside of prison.

The black convict pulled his cock out of Timmy's sucking, slurping mouth with a loud sloppy pop as if Timmy had been trying to keep hold of it and not to let it go. Who knows? Maybe he had been. It had actually made his eyes pop open from sleepy lazy eyelids to wide shocked eyes. This increased the laughter from the watching convicts and it made Timmy wonder if he had momentarily for maybe just a second actually done in truth what he was silently being accused of. He felt that overwhelming shame only a pervert caught in some shameful act can feel. It came once again with that sudden awareness of his surroundings that only enhanced it. The black convict told Timmy to lick up and down his fat black veiny shaft like it was a lollipop and that's exactly what Timmy began doing. He even started adding sound effects that seemed to emit from him on their own volition, sound effects that would have an unknowing witness think he was actually enjoying himself. Out of the corner of his eye, he could see some of the convicts had begun stroking their own big fat hard cocks, watching and wishing they were getting Timmy's expert service. Timmy wondered if he would have to do just that next, service each and every one of them; worse, he wondered if he wanted to.

Timmy put his mouth back on the fat black cock and began bobbing his head. He choked, gagged, gurgled and slurped, not of his own volition he kept telling himself, but no spectator ever would have bought that. Why he was doing what he was doing meant very little to the black convict. All he knew was that he was receiving one of the best blowjob he's ever had in his life.

Timmy was in for another shock. The female correctional officer was still deep inside him and still doing that thing to his prostate, rubbing her fingers over and over it. He had read about this sort of thing, but he didn't realize it was fact instead of fiction. She kept rubbing his prostate, massaging and milking it, causing him to have an intense erection and then...

Oh, no! Oh, God no!

The worst possible thing that could happen happened. He felt his little cock jump and twitch and jerk around and then, and then...

He was cumming!

Cumming after some shameful thought is embarrassing enough when you keep the thoughts to yourself, but cumming after performing a shameful act in front of a live audience is almost debilitating. And this wasn't just some live audience; this was an audience of stone cold killers whose perversions had no end to their dark depths whatsoever. There were cheers and whistles as Timmy's cum shot out across the floor and Timmy groaned out in an intense orgasm. The big black convict still hadn't emptied his balls into Timmy's sucking mouth. It was like he was holding back to fill Timmy's mouth full of hot, steamy, salty, bitter spunk during Timmy's peak moment of shame and humiliation and make that shame and humiliation even more intense. When his cum finally did fill Timmy's cock sucking mouth, he ordered Timmy to swallow it all. Timmy tried, but repulsed, he let a lot of it spill out and down his chin. Timmy began weeping while the convict used the head of his cock to wipe up Timmy's face and feed him back his own cum. He smeared what he couldn't fit back into Timmy's mouth all over poor Timmy's face.

"Thank him," the female officer ordered Timmy, squeezing his balls.

"Thank you," Timmy wept.

"What are you thanking him for?"

"I don't know," Timmy continued with sobs.

"What did you just do for him?"

"I sucked his cock."

"Then thank him for letting you." She squeezed his nut sack hard again.

"Ahh! Thank you for letting me suck your cock!"

"Daddy." She squeezed.

"Daddy! Ahh!"

"Again." This time she decided she didn't need to squeeze and she was correct.

"Thank you for letting me suck your cock, Daddy!"

"Anytime, sweetheart," The black convict said.

"And thank you for being so cooperative," the female guard told Timmy. She slapped his ass hard! Smack! Timmy was sure she must have left a handprint. "My name is Officer Monique Michaels, Miss Monique to you. I think I'm going to let these boys play with you a while and when you can't stand it any longer, you come and see me and maybe I'll still be interested in getting you into that program."

She walked off out of the room now and one of the male guards approached Timmy.

"Get back in formation, convict," the guard barked!

Timmy did so, weakly and feebly with his head down.

smutnut
smutnut
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AnonymousAnonymousover 2 years ago

I know I am late to the party but fuck I want to be Timmy. Awesome story and I can't wait until the day I am owned like that. As a skinny white boi it would be a dream come true to service the domiant race on this planet. I know my place and it is beta and to serve

getarisegetarisealmost 5 years ago
Oh baby. Yes.

I can’t wait to read on. But I don’t know if I can hold it down that long.

AnonymousAnonymousabout 8 years ago
Wow

Yes very nice . If all black men discovered that we white men all want to suck and be fucked by there black cocks where would the world population be. I have wanted a black cock for years and would love to be Timmy. All you black men out there find a white man any age and make your ancestors proud and own us, even us married straigh men want black cock. Find us and use us all.

AnonymousAnonymousover 8 years ago
Always good......

Always good to read about a white boy sucking a superior Black cock. The way things should be.......

AnonymousAnonymousover 9 years ago
Your terminology cracks me up...

"The female correctional officer was still deep inside him and still doing that thing to his prostate."

Oh No!... Not THE THING!... but she was doing him a SOLID! lol

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