What had started out as a harmless, fun-filled afternoon of prancing around in his older sister's clothes had turned into a disaster. He'd returned to her bedroom to grab one of her lacey bras when he suddenly heard footsteps coming down the hallway. For some reason, he'd failed to hear either a car pull up or the front door open as he normally did. Now, he was stuck in his sister's room about to be caught dressed in all her clothes!
Jimmy was so terrified, he nearly wet himself. He'd always known he was a sissy and he was used to being pushed around at school on a regular basis. One of the worst bullies was Chad, his sister's boyfriend who played on the school's football team. Chad was constantly pointing out Jimmy's feminine aspects, including his long red hair, and mocking him for his nerdy ways. And Jimmy's sister Brooke never did anything to discourage him. While she was unaware of Jimmy's secret fetish for dressing up in her clothing, she nonetheless agreed with Chad's general opinion of him.
That was all about to change as Jimmy stood there, cringing in one of Brooke's dresses, pantyhose and high heeled sandals. The look of shock on Chad and Brooke's faces was considerable but brief. Chad began laughing uproariously although Brooke was incensed at her sissy younger brother.
She immediately began shrieking at him while Jimmy tried to stammer out some sort of coherent excuse. In his distress and angst, he tried to run out of the room and past Chad but the bulky linebacker wasn't going to allow it.
"Oh no you don't," he said, gripping the fragile sissy's shoulder with his meaty paw, "You want to act like a girl, I'm going to see you get what you came for."
Chad pushed Jimmy down on his knees as unzipped his pants in one swift motion.
"I always knew you were nothing but a big, prissy sissy," he said as he fumbled for his cock, "Now we're going to take it to the next level."
Jimmy began pleading with Chad but he'd never had much in the courage department and everyone knew how much of a pushover he was.
"Open up, it's time you sucked your first cock," Chad said in a husky voice.
"No...no...please..." Jimmy squealed in his small, high pitched voice. He made a half-hearted attempt to get up but Chad easily held him in place.
Jimmy shook his head and tried to pinch his lips shut but Chad slapped him on the side of his face which caused him to cry out. Chad responded by jamming his swelling cock deep into Jimmy's mouth which made the sissy gag reflexively.
"I see you're learning to put on make-up," Chad said as Jimmy's warm mouth closed over his hardening cock, "With your sissy features, you could almost pass for a chick."
Jimmy could do little except struggle to accommodate the massive erection expanding and filling his mouth. He found his head bobbing up and down as Chad's slick pole was driven deep into his throat.
"I want you to look up at me when I blow my load into your mouth, sissy boy," Chad said as he guided Jimmy's auburn head into a steady rhythm that could only lead to one result.
It had been almost a week since Chad had last came and he knew he would be giving Jimmy a load that would fill his mouth to overflowing.
Being too terrified to stop the raping of his mouth, Jimmy sucked dutifully, hoping the jock who's pole he was sucking would make his humiliation short and quick.
"Look up at me Jimmy," Chad said as his breathing grew heavy and labored, "Because this is only the first load of many that you'll be getting."