Earn your Debt to Society

Brent had been in prison for several days now. By his own count he had been sexually assaulted a dozen times each day. Both his jaws and his ass hurt from the regular abuse he received. The guards thought this pretty boy could earn them some money outside and they arranged for him to be the entertainment at a bachelor party. To get him ready to rent out, they made Brent shave every inch of his body. The guard who inspected him, Officer Sanchez, enjoyed making the new fish squirm and be humiliated. After the shave and shower, Officer Sanchez marched Brent back to the holding cell. Brent stood there naked while two black men wearing bulging jocks entered and inspected Brent.

These two men were instructed to run their hands all over every inch and crevice of Brent's body to make sure there was no stubble. They could be a rough or as gentle as they wanted but they could not have sex with Brent. They enjoyed talking dirty to him as they pawed his body. They especially liked that he still had small swollen breasts from the saline injections of a few days ago. Each took a turn grinding their cocks against Brent's ass while reaching around and fondling his small breasts, squeezing them and whispering in his ear how much they enjoyed bouncing his firm, little tits. They would place their hands under his breasts and bounce them up and down. They still hurt as he was not used to having breasts.

When they finished playing with his breasts and had agreed his head and face were clear and without stubble, they checked out his arms and legs running their hands up and down his legs and paying special attention to his firm buttocks. One man stood behind him and grabbed both butt cheeks and pulled them apart. The other knelt in front and grabbed his cock with one hand and his balls with the other. The man in front pulled Brent's nut sack down and slapped his dick back and forth a few times. The man in back ran his finger up the butt crack and poked but did not enter Brent's well used hole.

After he passed inspection, Brent was led back to the doctor's office. Over the next hour he was given four enemas to clean out his bowel tract. When he was finally passing clear liquid, he was ready. A queen from cell block Nan arrived and painted Brent's face, painting eyebrows, adding eye lashes, rouge, mascara and bright red lips. A long blond wig was attached to his scalp to make him look more feminine. His entire cell block lined the corridor as Brent was marched naked (as his new womanly costume allowed him to be) then Officer Sanchez brought him to the van with the box. When in use, the box had just enough room for Brent to kneel down, rest his ass on his heels, his head was placed in a sling attached to the cover and just before the box was closed, he would be doused in cheap perfume so he smelled like a whore. There were two sliding doors on the box. One in front created a glory hole for Brent's mouth. The other was for back door fucking up Brent's ass. The box would be secured with a pad lock. Officer Barrett was driving the van and Officer Sanchez rode in back with Brent who was shackled arms out and a bar separator attached to his ankles was driven to the bachelor party. Along the drive in the back of the van, Officer Sanchez donned a latex glove and added some lube. He stroked the cock of the helpless Brent and then lifted the separator bar and lubed Brent's bung hole which would get much use tonight.

The party was eight college frat men, already buzzed on beer, porn and pot. When the box arrived, it was placed on a two foot high platform by Officers Sanchez and Barrett. The front glory hole was opened and the first stud unzipped and rammed his already hard member into Brent's mouth. Brent knew the drill and sucked with his mouth and lips, no teeth. The first guy was so horny it only took three minutes of pumping to empty his nut sack of hot cream into Bent's stomach.

The second guy was thicker. He just put the head of his cock in Brent's mouth. Brent used his tongue to get it wet and play with it. He had learned a lot in two days from the men in his cell block telling him what to do and not do so he would not get hurt. He remembered well the one time he tried to fight back and used his teeth and was uncooperative. When he did that, snap clothes pins were attached to his nipples, cock, balls and down the length of his abs and his perineum (the space between balls and ass). It was very painful. He had to suck off two men while being fisted before they would remove the clothes pins and it hurt like hell to have them on and even when they were removed. But back to the second frat boy to skull fuck the bitch in the box. The thicker man meat slid just a little in and out until the stud was ready to work it in deeper and deeper each time. Brent relaxed his throat to take it all in and the second stud held it in deep for a few seconds before building a steady rhythm. The steady in and out pumping of the cock helped Brent pace his breathing so he would not gag or struggle to breathe. As things were building to an explosion, Officer Sanchez slid open the back door and invited the men to butt fuck the bitch. The crowd had been told that this was a woman from the ladies prison who agreed to a reduced sentence if she could entertain the boys. They were excited to help out and after an hour of hard core porn they were primed.

One boy shouted that he had never butt fucked before and was first in line. After a stroke or two to stiffen up, he plowed right into Brent's hole in one steady and rough push. This caused Brent to lunge forward on the spit roast cock he was swallowing and the sudden lunge caused the stud in his mouth to shoot three volleys of sticky cum into Brent. The suddenness of the loads shooting in his throat caused Brent to push back and impale himself even more on the rod up his rear. The boy on the butt end shouted that she must really like this because she just humped back on his dick. This third man was all the more excited and slammed rough and hard into Brent until he shot off a few loads deep upside Brent.

Meanwhile a fourth man was in Brent's mouth. His jaw was getting tired from being open so long. A second man (number five in total if you are keeping count), mounted behind Brent and used the cum already inside to lube his manhood. I may have sloppy seconds but at least I'm not dead last to hump her, he said. Brent would take two more cocks up the ass and two more in the mouth. That makes nine in total as the guy who went first was ready for a second round and wanted to try the back door entry this time.

When everyone was done and unloaded their spunk into the good prison bitch, Officer Sanchez placed a butt plug up Bent's ass to prevent the seed from dripping out and then closed up both slots and collected the box. Officers Sanchez and Barrett carried the box back to the van and unlocked it letting Brent out and shackled him like before. Officer Sanchez was driving back to Brutewood so Officer Barrett remained in the back of the van. Once the van started to roll, Officer Barrett walked over to the bench where Brent was restrained. He stepped up on the bench and placed his legs on either side of Brent. He unzipped his pants exposing a semi erect eight inch piece of uncircumcised meat. Brent knew the drill; he had tasted Officer Barrett before. Brent opened wide and Officer Barrett entered his now growing hard on into the waiting lips. Officer Barrett skull fucked Brent banging his head against the van wall. Officer Sanchez heard the noise and knew what was going on. He unzipped his pants, pulled out his member and jerked off on the ride home.

When the van reached the prison gate, Officer Cowen greeted Officer Sanchez and noticed his stiff meat. Officer Cowen commented that there must be a bitch waiting in the back to finish off the job, Officer Sanchez agreed. They pulled the van inside the gate and Officer Barrett released Brent and brought him to the cab of the van. Officer Sanchez opened the door and ordered Brent to suck. Brent did as he was told. He had swallowed all of Officer Barrett's jizz and now he would get a mouth full of Officer Sanchez's hot juices. Officer Sanchez held Brent's head down as he blasted a few loads of cream. Brent was returned to his cell block dressed up and with the butt plug still inside. He was ordered to sleep like that so he might get pregnant and breed other bitches. No one was allowed to touch him that night. He had earned fifty dollars a pop plus travel expenses. That was a good night's wages for the Warden.

Since Brent was new and still firm, his ass was not torn up too bad, he would be in high demand soon. Showing pictures of a man with both cock and tits made him highly valuable in the party trade. Now that he had been broken in, he would earn money each weekend by being rented out. For every one thousand dollars he earned, Brent would have his sentence reduced by one week. He had earned $450 for the one party. The next night he was scheduled for a gay party and he would service a dozen men each paying $100 for what they believed to be a transgender. There would be no box on this next trip. He would earn his pay lying on a circular bed that spun like a lazy susan for the men to stuff both ends at once and rotate to take turns. By the end of the weekend, he earned one and half weeks off his sentence. With this second group, they would also wanted him to drop a load or two so he would get some relief for his sexual tension.