Prison Lesson

Grant continued to defy the men until the third one said, "Lets just plow him dry!" They waited for permission from the prisoner with his penis on Grant's lips, who appeared to be the man in charge. Once he agreed the third prisoner dropped his pants and started to stroke his long circumcised penis. It wasn't as long as the first prisoner's which was about ten inches, but it was thicker like a beer can and it still looked to be about seven inches. The third prisoner shoved a finger into Grant rectum and Grant screamed in pain. Once he opened his mouth the first prisoner shoved his long foreskinned dick into Grant's mouth with a warning, "You bite me and I will cut your balls off and shove them up your ass."

The third prisoner told the second to operate the bed and push Grant's Stirrupped legs back until he was in a fetal position which would open up his ass hole even more easily. Once the machine had pushed them back as far as they would go the third prisoner enter Grant's ass with his beer can cock. Grant couldn't scream because his mouth was full of cock, which was making him gag as tears ran down his face. Grant's ass took the first pounding for about five minutes until the prisoner shot a big load of cum up his ass.

The first prisoner whispered into Grant's ear as he pulled his dick out of Grant's mouth that he should have sucked the first cock and got it all slathered up and then it would not have hurt as much. The first prisoner went around to take his turn at Grant's ass while the third prisoner pulled his cock out of Grant's ass with a wet plop sound. The second prisoner dropped his pants and came around and shoved his little skinny four-inch penis into Grant's mouth. Grant had little fight left in him as he tried to get past the pain of the beer can cock's invasion.

The first prisoner pushed his cock into Grant's ass with little resistance and some ease because of the cum left behind by the third prisoner. It wasn't until the extra length of penis began to go where no cock had yet gone that Grant even felt this intrusion and he winced and almost bit down on the cock in his mouth. Trying not to bite the second prisoner's cock he used his lips to soften the impact, which in turn caused the little penis to explode in his mouth. Grant was surprised at the taste of cum in his mouth. He thought it would make him vomit but he swallowed it quickly and was amazed at how inoffensive the salty fluid really was.

All of a sudden the cock in Grant's ass hit something inside of him that made his own cock jump to attention and the third prisoner laughed and said, "look he is getting off on this!" Which of course couldn't have been further from the truth. The first prisoner then blew his load up Grant's ass and pulled out quickly. He slapped Grant's hard dick and told him, "You are now property, welcome to hell!"

I sat on the couch and was flabbergasted. I couldn't believe that anyone could rape Grant. I suddenly became very afraid. How was I supposed to stop them from raping me? I had never been in a fight in my entire life. Grant went on to tell me that he had many experiences like that, but after awhile he began to enjoy certain aspects of them. He told me it could have its enjoyable side to it , but that I should never admit I am enjoying the experience because that could get me killed. I stared off and blanked out for awhile, going into my own little terrified world until Uncle Grant opened a bag he brought with him. He took out a large bottle of petroleum jelly and unbuttoned his jeans.

“You need to be broken in, because the dick in prison are a lot bigger than mine. So, get your clothes off and get on the floor.”

“What??”

“Or bend over the sofa, I don’t care, but your hole needs to be prepared or they’ll rip you in half.”

I sat there and just stared at Grant as he got undressed and started slathering his dick with KY. It began to harden and it was even bigger than I remembered and my asshole started to clench.

Grant grabbed my arm and guided me to my feet, turning me around and bending me over the arm of his sofa. He yanked my sweatpants down around my ankles and began to lube my really, really nervous asshole.

“Relax, or it’s really going to hurt.”

There was no way I could relax, and when Grant stuffed a thick finger up inside me I yelped. I realized that this was going to happen and was probably good for me to not be raped the first time, so I grabbed a pillow and bit down on it.

Grant’s thick penis now split my cheeks and pressed against my slick, but tiny hole. He gently pushed the head of his cock into my rim and I bit hard into the pillow and it sent a jolt of pain through me. Then the entire shaft got slowly stuffed in and Grant started to fuck me. He fucked me deep and slow at first, then seemed to enjoy himself as he picked up the pace. As Grant rammed into me, his fingers dug into my hips and the fury of his cock slammed into me like a whore.

Grant’s palms pushed my ass cheeks upward so he could get his meat deeper into my fuck hole and I thought I’d explode with pain and humiliation until a twinge went up my own shaft and I realized I was getting a hard on.

Suddenly a warmth filled my asshole and I realized that it was Grant’s load spurting into my asshole. I didn’t know what to do, so I just remained still, even though the idea of his wad up my ass was disgusting to me.

After a few seconds, Grant pulled out and jerked my pants back up over me then told me to go ahead and stand up. As I did, his spoo began to ooze from my asshole and I yelled, “What the fuck? Why’d you cum up my ass?!”

“Get used to it,” Grant told me, “because you’ll likely have 4 or 5 loads in you at a time. I thought you should know what it felt like before you have a strangers cum in you hole.”

Grant and I watched football for the rest of the evening and I mentally prepared myself for the reality of prison.