Chase loses his virginity a second time

*gay warning alarm*

Chase was minding his business when someone approached him. He looked up to see the broad figure of Gary, the class bully. What made his demeanor even more infuriating was his natural good looks and wealthy family. Life truly could be unfair sometimes. Chase prepared himself for a wedgie, or water poured on his head, or being made to be a gopher. Wedgie it is then, Chase thought when Gary reached for his pants. Instead, he pulled them down in one move, exposing his ass and crotch.

"What the fuck?" Chase yelled and tried to pull his pants back up. Gary stopped him from doing even that, and overpowered him easily. "What are you doing?" Chase asked, feeling both fear and humiliation. He noticed Denise, Gary's hot girlfriend nearby.

"What do you think, dumbass. It's free use day!"

"What does that have to do with me?" Chase was still not connecting the dots. Only when something hard brushed against his ass did he realize the trouble he was in.

"Wait wait wait, no! Stop!"

"Shut the fuck up! You're ruining it!" There were boos from the rest of the class. Free use day was to be strictly adhered to, and deviation from the rules was seen as a major faux pas. Besides, even if Chase wanted to run away, he couldn't shrug off Gary's iron grip.

He felt a touch on his limp cock. "Look at this cute little guy!" She teased. Denise was one of the popular girls at school, perhaps even the most popular. She was a tall Nordic goddess with a perfect, toned body and leg for days. Chase had of course used her as fap fuel countless times in the past. Just a light touch from her gave you an erection in a matter of seconds.

Denise raised an eyebrow and giggled. "Maybe not so small after all." Distracted by the beauty, Chase momentarily forgot his impending fate until something poked at his anus. He squirmed to no avail. Gary must have put on some industrial grade lube because his large cock began to penetrate his virgin anus.

Chase squeezed his eyes shut as he was forcibly violated by a man he despised. To his surprise, there was no pain or discomfort. Only... pleasure? Chase was equally horrified at the idea that he loved a cock up his ass, but there was no denying it when Gary began to thrust and a small moan escaped his mouth.

"You love it don't you, little bitch!"

Cheeks burning from shame, Chase had no retort. It was the truth. Every time his cock slammed into him, Chase felt his mind go blank and his cock throb with pleasure. He had never experienced such a sensation and it was overwhelming him. It didn't help that Gary was fucking him at mach speed.

"Fuck, that's hot," Denise said. Chase looked at her, and his eyes nearly popped out. She was sitting on the desk beside him, watching her boyfriend fuck another guy while she had one hand up her skirt and was obviously fingering herself.

Staring at the gorgeous woman masturbating made the ordeal much more bearable. In fact, he was even beginning to enjoy himself.

"Look at this sore cock. Let me help you with that..."

Denise's fingers, slick from her own juices, wrapped around your aching cock and began to stroke it. Remembering that free use day rules should still apply, Chase grabbed Denise close and began to feel her up in return. He had never been in such lust. Denise's handjob felt amazing, just as Gary's cock stirred up hitherto inexperienced sensations.

His orgasm approached at a glacial pace, but once at the point of no return it struck like an avalanche.

"Cumming! Holy fuuuuuuuu-" Chase screamed his throat hoarse. Denise only jerked him harder, and the first rope of cum shot out like a straight beam, hitting the person in front. Subsequent loads painted his desk white. Chase had never cum so hard in his life and his body went limp.

"His ass is so fucking right! I'm gonna- gonna blow too!" Gary said, and he ejaculated inside Chase. Denise was licking the cum off her hand, enjoying the show from the side again. When her man was done, she embraced him and gave him a sloppy kiss. Chase was left half-naked on his seat, abused asshole leaking cum.