Billy & the Big One

By JIMMY

Pulling a dumb prank landed me and my buddy Billy in jail. After the humiliating experience of being finger printed, photographed, and stripped searched, we were led to cells. I lucked out and got a cell to myself but Billy was put across the hall from me with some dude.

We stood at the bars and talked a little while, we had both called our parents and would get out in the morning. The lights went out at 10 PM and we hit our bunks. I had trouble getting to sleep but dozed off at some point.

I woke up suddenly. I realized it was Billy’s voice that had woken me up. I looked across the hall.

“Get away from me dude!” Billy demanded, “Get the fuck away!” He was backed into a corner of the cell.

I was shocked, his cellie was buck naked! I’d heard those things about not dropping the soap, who hadn’t? To actually see a situation like this was confusing and shocking.

Billy was a great looking guy, blonde hair, blue eyes, and a good build. His good looks had always worked well for him with girls, I guess in jail it was working against him.

He was trying to play tough but I could see he was nervous. I didn’t blame him, who wouldn’t be nervous locked in a jail cell with s naked guy.

Again, Billy demanded, “Get the fuck away! I mean it dude! Back off me!”

The man didn’t answer, he back handed Billy hard, a real bitch slap. I heard Billy’s head hit the wall with a thump.

“People are watching man, you better stop!” Billy was not able to hide his fear now. I could see it.

My mouth fell open as the naked man turned facing me! His dick was so big it didn’t look real, it didn’t seem human. It was so hard; it stuck straight up, reaching towards his chest!

He sneered at me, then turned back to Billy. “Your buddy is welcomed to watch. I don’t care. Hell, I kinda like the idea of getting watched. I got a big fucking cock, I don’t mind showing it off. Now, am I gonna have to mess you up? Or you gonna be a good boy?”

Billy didn’t answer, his face was pale. He was terrified. He had every reason to be, he was no match for the guy. Billy was a lover, not a fighter. He was trapped in that cell!

Billy cringed as the man’s hand reached out, I thought he was going to slap Billy again but it was even worse. He unsnapped the buttons on the jail coveralls Billy wore. He slipped the coveralls away from Billy’s shoulders and arms, they hung at his waist now. His chest was exposed.

“You are a pretty boy, fucking beautiful.” The man said. He ran his hand over Billy’s chest, feeling my buddy up. “Nice and smooth, firm muscles, soft smooth skin. Have you every pleased a man boy?”

“Fuck no!” Billy sounded hysterical. “I’m straight as it gets, I don’t do dudes”

Billy was backed up in the corner, his eyes had a wild look. I thought about yelling and making noise, maybe getting a guard to come help. That idea was in my head about a split second, it was snitching and that ain’t my way. Besides, Billy could yell for his own help.

I did wonder why Billy wasn’t at least fighting the guy. The guy was bigger and older, but you don’t just let a dude do shit like that to you, you know? Billy was my friend, it probably wasn’t cool to watch, but watch I did.

The guy’s fingers moved to Billy’s nipples. Billy’s look of horror intensified.

“Feel that boy? Your nips are getting hard just from my rough fingers. You need a man, boy.” He was sneering.

I couldn’t really tell, but Billy’s nipples may have been hard. I wrote that off as a guy thing, hell, my nipples get hard when the wind blows. I freaked out when the dude placed his mouth over one of Billy’s nipples. The guy had to be as gay as can be to suck another dude’s nipples!

Billy just squirmed and looked miserable as the man sucked and played with his nubs. The dude would play with one, and suck the other. Back and forth, and the guy was really getting into it.

Then I got a bigger shock! Apparently the man had tired of the nipples, he worked his was down Billy’s chest, licking, sucking, kissing, and nibbling. He bent and lowered, his mouth and face working down Billy’s stomach. I gulped as he began slipping the uniform down Billy’s hips!

“Yeah, you got a pretty dick, boy.” The man’s voice was raspy and husky. “Beautiful dick, nice smooth balls. Yeah, gonna suck you dry, pretty boy! I’m gonna drain you!”

I don’t know what my face looked like, I was shocked! Billy sure was too! That dude, that guy with that huge fucking boner opened his mouth and went to town on Billy’s cock!

The dude knelt before Billy, and just opened his mouth, taking all of Billy’s soft cock inside. As he sucked, both of his hands were between his own legs stroking that big prick of his!

As he sucked, Billy was getting hard. There he was, with another dude forcibly sucking his dick, and he was getting hard. But just from watching it, I was too! I was hard as a rock!

The guy worked his head up and down! He’d pull off and go down and suck Billy’s nuts. He jerked his cock as he sucked my buddy! Billy moaned, his body was tensed up. The guy was gobbling Billy’s goober like a pro with a lot of practice!

Billy gasped and his body flexed! I knew he was cumming! I’d never seen another dude cum before but I knew he was shooting a load! If I hadn’t been so shocked, I probably would have pulled out my own stiffie and got off! Oh, and that man, he was swallowing Billy’s juice! That big dude with that huge cock was swallowing Billy’s cum like it was a cold beer!

Billy & the Big One Part 2

By JIMMY

Billy’s cellmate licked his lips, “Ain’t nothing like some sweet cum from a pretty boy’s cock. Pretty fucking little man! You got some sweet cum, hot little dick! Yeah!” The man stood, he was using both of his hands, jacking on the super sized cock of his, licking his lips, staring at Billy! “Yeah, you are one hot pretty little boy stud! Gonna make me cum, you pretty mother fucker! You’re so hot, so sweet! Oh, fuck! Here it comes!”

I watched as the dude aimed that huge thing and began spraying cum! Some of it hit Billy’s face, some hit his chest, but the dude shot most of it right on Billy’s manhood! This was sick! He sucked my buddy off then shot his nut right on my buddy’s private parts!

Then the man started licking, eating his own load right off my buddy’s face and body! He started licking cum strands of Billy’s face and worked his way right on down.

As he cleaned Billy’s cock, he started sucking on it again. Billy protested, saying his dick was too sensitive after he nutted but the dude didn’t want to hear any of that. I knew how it almost hurt after I jerked off and my dick touched something, and Billy was squirming and flinching. The man just worked on Billy’s fuck stick. After a while, Billy was firming back up. His dick was getting harder and harder as it was forced sucked for the second time.

I wondered what it felt like. It had to feel good, Billy was hard again. That dude had some kind of nerve, making Billy give up some dick, not just once, but a second time. I needed to jack from just watching but I suffered. I could see the guy’s cheeks, all sucked in as he worked on that dick! He never gagged or choked, just slurped up and down the cock, only stopping every once in a while to suck on Billy’s nuts. The guy handled nuts as good as he handled cock, he sucked them both in his mouth at the same time, his jaws bulging as he rolled them around.

It took a while, but Billy was getting close! His face tightened, his muscles tense, and his hands were fists as he started blowing load number 2! Again, the dude just swallowed it all, not missing a drop!

“You drained yet, pretty boy? Did I drain you? Or you want some more? You got any more cum for me? I like that sweet cum! I like that pretty little cock!” the man seemed to be bragging.

“I’m done man, I’m fucking done! I can’t take no more!” Billy announced.

“That’s cool then,” the guy said, “I’m gonna eat your ass now. I’m gonna lick that straight ass for you!”

Oh, fuck! This guy was sick! He had no shame, first a cock sucker, now an ass eater? I shuddered, feeling disgust. Billy didn’t want the guy any where near his ass, but he didn’t seem to have much choice. The man threw a mattress on the floor, and forced Billy down on all fours.

He ran his hands over Billy’s butt, “Pretty ass, I’m gonna rim this sucker good. Nice little asshole, gonna lick it. Hold these big muscled cakes apart for me, so I can get my tongue up in that pretty hole!”

That is exactly what happened. The dude had his face down in Billy’s butt crack. For a few seconds, Billy had that horrified look on his face. Then his face changed, it looked like he was enjoying it. I could hear the man slurping away back there, and then Billy would moan ever so often.

From across the hall, from where I stood, it looked like Billy was in heaven. That look on his face was definitely pleasure. His cock was even hard again! But my buddy couldn’t see what was going on behind him like I could. That dude was licking Billy’s bum and jerking on his huge cock!

I knew that this guy wasn’t just gonna be happy sucking dick and eating butt, this dude was gonna want more. Soon enough, I was proven right.

The guy pulled his head away from Billy’s butt. “I got you all opened pretty boy. That little hole of yours bloomed like a rose. It’s winking at me. It likes me, and I like it even more.”

The man stood up, Billy started to rise. “Oh, no, boy! You stay right down there and keep those buns of yours spread. I like that little hole. I ain’t done with it. I got some more work to do on it, gotta get it ready for my dick.”

Billy jumped up, “I ain’t getting fucked! It ain’t happening!” He backed into the bars now, I could see spit on his ass!

The man just glared, “Get your bitch ass back down there! Stupid ass punk! Get back down!”

Billy must have sensed the same thing I was sensing, this guy could be violent. Billy got back down. It was wrong of me, this was my best bud, but I wanted to see this, I just couldn’t believe that huge cock could fit in an ass!

The guy had a bottle of lotion, he knelt behind Billy again. He slapped Billy’s butt, “Spread em pretty boy. I gotta dilate you and grease you up. You ain’t ready for my cock yet. I ain’t trying to hurt you. If I wanted to hurt you, I would have just fucked you from the get go. You’re a sweet looking kid, I just wanna enjoy a piece of you. You’re in jail, you’re a pretty boy. What did you think was gonna happen?”

Billy was holding his butt spread, he was looking over his shoulder at that super cock and that bottle of lotion. He looked at me, his face red with shame. Billy went into a plea bargain mode, his voice was low. “I’ll suck it if you don’t fuck me.”

The guy grinned, “You think I’d let those sharp teeth of yours around my cock? No way! Besides, you need to suck your way up to be able to handle a cock my size! Maybe when you get out, you can practice on your buddy over there. You ain’t ready to suck a dick like I’m packing!”

Billy tried another approach, “Please don’t do this to me, sir. Please?”

The guy ignored him. “I’m gonna finger you, take my time, get you opened all the way. I want you to relax that tight little ring, think about my tongue when it was inside you, come on relax, relax it boy!”

The guy had a finger in Billy’s ass! “See boy, that’s a finger, my tongue had you all ready for a finger. Can you feel it? I’m lubing you inside. Yeah, just stay relaxed. I’m gonna add a second finger now, boy. More lube and more finger. You just stay relaxed, you take it easy and I’ll get you all ready. I got two fingers in you now, feel them?”
“Please stop it man, uh sir! I don’t like this, I ain’t liking this at all,” Billy pleaded.

“What about this boy? That’s you butt clit I’m touching! It’s making your dick and balls feel funny, huh boy? Pretty gay boys all have this little special place in their asses, a place that can be touched and make them know what they are. I’ve found your little clit, boy.” The man was breathing heavy.

The guy was finger fucking Billy, two fingers inside my buddy’s ass! Bill had a strange look on his face, a look I didn’t recognize but somehow knew was sexual.

“Your dick is getting hard, boy. Something happening that you like? Something turning you on?” The guy questioned. “Here comes finger number three. Don’t tense up, just relax.” Billy gasped and it looked like he was feeling some pain. “That’s three fingers inside you. You got three of my fingers, you can take it. Yeah, you can take it.”

At first Billy seemed in pain from the three fingers. Then he had that strange look as his ass was finger fucked, I could see his dick, he was rock hard. I looked at three of my own fingers! No way! Damn! How could Billy take that?

“Okay, boy, here comes finger number 4, relax that sweet hole, relax it, think of how good it will feel to have 4 fingers touching your boy clit. 4 fingers rubbing inside you, touching that special place in your hot pretty ass.”

Billy groaned, “It hurts, oh, it hurts.” He looked horrified again, his cock was rapidly shrinking. He groaned.

“That’s it boy, all inside, all inside your tight ass. Yeah, take it, your almost ready boy. Give into the feeling, give into it. Your little dick is getting hard again, don’t be ashamed. Try and just enjoy it. You’re opening up real good. In a few minutes, I’m gonna replace my fingers with my cock, boy. I’m gonna give you the real thing.”

Billy looked frightened, he looked scared. I could hear some squishing sounds as the dude used four fingers to fuck Billy’s ass. I saw him add some more lotion and finger it into Billy’s ass. Damn! I watched as the guy started lubing his cock! The thing was huge, and the lotion made it look even bigger. I had watched Billy take four fingers, but how was he going to take that dick in his ass?

“Just relax, I’m only get put the head in right now. The head ain’t that thick, stay relaxed. That’s it boy, I’m going in, real slow, just the head. How’s that boy? How’s that feel?”

“It hurts a little, its real hard. It’s hurting,” Billy groaned. All I could do was stare, my buddy had a cock in his ass! A dick! Shit!

“Just relax, stay relaxed, I’m letting you get used to it. It’s gonna get thicker and thicker. There’s gonna be some pain, its gonna hurt. You try and enjoy that pain, boy. You’re tough, you can take it. I’m gonna slide a little more cock in you, boy. Couple more inches!”

“Uh! Stop! I can’t, it hurts! No more! Gawd, no more!” Billy’s seemed hysterical. “Oh fuck! Fuck!”

“That’s a third of my cock boy. A third of my prick in your hot tight hole. Yeah, your gonna be a sweet fuck. My big dick is popping your cherry. I gotta lot more dick for ya boy. We’re just gonna work slow, a little at a time. I’m stretching your ass, making it into a nice boy cunt. A pretty boy like you needs a nice big stretched out pussy. Your buddy over there is watching, his uniforms all tented, he’s all boned up watching us. I bet he wants some of your cunt, maybe he wants some of my cock.”

I could feel my face burning, I had been trying to disguise boner. I could have climbed in the bunk, but there was no way I could stop watching.

The man called over to me, “Go ahead, pull your dick out. You know this has you hot. You ready to see your buddy take a little more dick?”

Truth was, I did want to see that. As sick as I thought all of this had been, it had me turned on. It had me as stimulated as I could ever remember being.

“Okay boy, time for a couple more inches, time for me to slide you a little more dick. This is gonna be the thickest part. You’re gonna think your being torn in half. Assholes are amazing things, boy, they stretch and stretch. Relax boy, here it comes!”

Billy cried out, “Stop! You gotta stop! Stop, just for a second! Gawd! Gawd!”

The man chuckled, “That’s half of my dick. It’s the thickest part though. You got a lot of cock in you, boy. But I got a foot of prick, you still got 6 inches to go. Its gonna get easier after this. You think you can’t take it, but you’re asshole is already relaxing again.”

“It hurts so bad, man. I don’t wanna do this. I feel like I’m gonna black out or something.” Billy groaned.

“Oh, then you feel free to pass on out boy. Now, I’m gonna start fucking. Just a little, I’m just gonna use the first 6 inches. I’m gonna leave the head inside you and just fuck a little, slow at first. That’ll help stretch you and get your cunt ready for the real fucking.”

“Gawd, no!” Billy groaned. I couldn’t take much more, I opened my jumpsuit and touched my cock, the man was fucking Billy! My straight buddy was getting fucked up his butt!

I stood, touching my dick, watching the scene. Billy squirmed, his hands were opening and closing as he got his ass screwed!

“Yeah, boy, yeah, you got a good cunt. Yeah, you were made for fucking!” The guy growled. “Umm, nice big boy pussy! You ready for more? You want a couple more inches?”

Billy gasped, “Just a little more, not too much, okay?” I was in total shock, my buddy was basically asking for more dick! He wanted more cock! I’d known Billy a long time, he’d always been straight, he’d never shown any sides of being gay!

The dude gave Billy some more, he fucked slowly, sometimes sneering at me when Billy moaned. He worked more and more of that cock inside of my buddy.

“I’m in all the way, boy. I’m in all the way. Found that pussy muscle of yours and learn to squeeze it. Tighten that boy cunt! Yeah, milk my cock! Squeeze that pussy!”

“Gonna take it home boy, gonna screw you good!” the man was moving again, he was biting Billy’s neck, fucking faster and faster!

I was looking down, now openly beating my meat, when I heard a yell! I looked up.

“I’m gonna cum!” Billy was yelling again! “I’m gonna shoot!” Billy’s hands were on his cock, they were holding the bars tight! His face was contorted! “I’m cumming!”

The man sneered at me, then he winked. “Yeah, yeah shoot that load pretty boy! Yeah, ah yeah! I’m gonna join you, boy! Gonna fill your cunt up with my boys! Yeah, gonna cum in your big juicy cunt!”

I started shooting my own load then, I let my cum fly, it was landing in the hallway. I moaned and in the background Billy and the guy were moaning. They fucked several more times that night, I woke up and watched them, pulling my pud as I watched my buddy willingly take the long thick cock inside his ass!

Tomorrow, when we got out, I was gonna have a lot of questions for Billy, well, after I tired some of his jailhouse cunt.

The End

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