Chaperone Becomes a Bitch Chapter 3 by Jack Sone
Josh sat on the bed, leaning against the backboard with his legs spread. I crawled up to do what I was supposed to do and started giving him the best blow job of my limited experience. I hoped he wouldn't treat me bad. He was in a tough spot. I still think he was a nice kid and maybe I could limit the damage to my future. After all, I had four years of Josh to look forward to, or dread.
Chapter 3
Josh didn't take long at all and really didn't participate except by feeding me his sweet boy cum. He just laid back and I did all the work. His eyes were closed and he moaned, but he didn't guide my head or fuck my face. I just bobbed and slobbered and tried my best. Evan and David just watched jerking their dicks and waiting. I didn't get it. Why did they invite Josh? What did they have to gain from it? Josh was a stupid little freshman who was using their new bitch, just delaying them getting another crack at my holes.
After Josh came, Evan gave him props. "Nice job little man! How'd you like your first blow job?
"Awesome," said Josh, aglow in the aftermath. "I could get used to it."
"Exactly!" said Evan. "See, girls take work. You gotta charm them and waste time trying to get it. It takes money and effort. Teacher-fag here is our cum dump. Whenever we're horny, he's going to do what bitches do, right fag?"
I nodded. I had no choice. To tell the truth though, giving Josh a blowie wasn't all that bad. I actually enjoyed it. He was cute. He didn't treat me like shit, and there was no pain or humiliation. This might work out ok, as long as no one else found out. Evan isn't Josh though. Evan enjoyed being mean. He liked to see me suffer. Maybe it was caused by something in his past. I don't know, but I could see in his eyes as he stared me down while stroking his cock, that he was going to take advantage of the fact that he could take what he wanted.
"Watch and learn Josh. I'm going to show you how to fuck a pussy," said Evan as he moved toward me. He grabbed my hair and shoved my face to the mattress. Getting behind me, he grabbed my hips and pulled me toward him. He was strong and he lifted me off my knees as he pulled my ass into a position that he wanted. His needs were all that mattered and that was apparent to everyone in the room. He was showing off for Josh, establishing himself as the alpha male. Josh was stroking his growing dick again - ahh, to be that age. Recovery takes seconds.
Evan pulled my ass to the edge of the bed and lined up with my hole. I heard him spit and felt the head of his cock pushing against my asshole. I heard him spit again.
He leaned down and whispered in my ear, "Open up bitch, I'm here for my pussy." On the word pussy, he shoved forward pulling me back by the shoulders and impaling me on his spear. He drove it in fast in one motion until it couldn't go any further. I cried out and tensed up, trying to squirm away. He pulled me back.
"Where you going boi? Come on back here," he said while he pulled me back onto his cock and into him. He was so strong. I was no match and couldn't pull farther away if I wanted to. The pain made my eyes water. I looked up at Josh. He was still stroking himself, but looked worried... maybe scared. Then his mouth corners turned up a bit and he started to smile.
"Yeah dude. He's fucking crying," said Josh. "You're making a teacher cry!"
"You ain't seen nothing yet." Evan was in his element. He had an admirer. He liked fucking, but he liked showing he was top dog even more. I was moaning and grunting with each thrust. "Shut the fuck up," grunted Evan in rhythm with his assault. "Josh, stuff his mouth man. Bitch is going to wake up the whole hotel."
Josh moved onto his knees and his dick was level with my mouth. My sight was blurry from the tears, but not enough that I couldn't see his now familiar dick. Evan took what he wanted. With Josh, I wanted to please him. He was a nice guy. I leaned forward and engulfed his dick. With my mouth full of Josh, the assault on my behind become more bearable. Evan thrusted into my ass while Josh pushed the other way into my mouth. With two dicks invading your innards, you begin to wonder about your life choices. More questions came to mind when the biggest dick in the room came into view.
"Yo bro, let me get in on that." It was David, the mocha colored, big dicked, happy-go-lucky friend of Evan's who was along for the ride. David was bare assed naked, skinny and brown, with dark curly pubes that seemed short due to the sheer size of his manhood. David had moved up to Josh's side, dick in hand, ready to get his rocks off in my mouth. Now there were two dicks in front of me. One at least 8", dark, hard, and angry looking. By comparison, Josh's dick was a little toy. Skinny, about 5", light blond pubes, and a pink head.
David slapped my face with his cock while I continued to give Josh a blow job. It was hard and the slaps hurt.
"Come on teach," said David. "You know you want it."
I let Josh go and moved my mouth to my left and took in David. I had to open wide and David immediately started fucking my mouth. I gagged as he wasn't gentle as he plowed the back of my throat. He grabbed my ears and pumped while Evan continued his assault behind me. Their enthusiasm and endurance were admirable. I'm not sure how long it continued, but it was long enough to begin to get pleasure. Evan had his way with my prostate and I guess I just let it overcome me. I bucked in rhythm to the assault and began to moan, reaching down to stroke my cock. I lost sense of all but the intense sexual feelings of being used by two teenagers who left no doubt they were in charge.
Evan began pumping faster and harder. He began slapping my ass with each inward thrust. Sex to him involved being in charge and making the other suffer. His sweat dripped onto my back and my ass began to sting. He grabbed my hips and pulled me back hard onto his dick, taking David's cock from my mouth. Evan leaned back on his heels and had me on my lap. I felt his cock shudder inside of me and then the warm spurts of fluid filled me up. He shook. I could tell it was an amazing orgasm. He held me tight with his cock as deep as it could get while he recovered, not moving, but breathing heavy. David and Josh were watching and stroking. It must have been a hell of a sight because David got to his knees and shot stream after stream into my face. Josh leaned back and shot his second load of the hour. Wasn't much, and it pooled in his belly button. I was the only one who hadn't gotten off. The sound of heavy breathing filled the room - most from Evan whose dick began to deflate.
He slowly guided me off his dick. He didn't say a word and got up and headed to the bathroom. I was left on the bed with David and Josh. Josh cleaned himself off with the sheet as David's cum dripped onto the bed.
David smiled. "I like that look on you Jack. You should keep it."
They all dressed and left. No one said another word to me. As they dressed, they chatted about the trip. Tomorrow we headed home.
After they left, David's cum drying on my face, I jacked off my biggest load in a decade smelling Josh's cum on the sheets and the feel of Evan's ravaging of my ass.
At least it was over tomorrow. We'd get on the bus. Head back to town. Life would return to normal. Right?