(Commission of OC by Alexander "Alex" Whitemount.)
(Bigger versions found on my Fanbox.)
SUBJECT: sissy, femboy, orc, horsecock, bulge, cumflation
"All his hard work was paying off. His bodyguard turned mistress had been slowly but surely crafting his already feminine body into a figure of swaying hips, fat thighs, and an oh-so-fuckable rear. He had questioned her methods at first. Not many boys want to make their ass their best asset but after the first couple of weeks of training accompanied by some "deep training" from his bodyguard, he'd quickly come to appreciate the wonders of a bubble-butt. The perfect amount of sculpted cushion did wonders for one's self-worth as well as providing the kind of buffer against the powerful swinging hips of his mistress. She loved seeing his pale cheeks turn a cherry red.
This all came to a head when she suggested he try out for the cheerleading squad as a freshman. This would be his first year. He was unlikely to make any friends, let alone make the cheerleading team. He expressed his doubts to her that evening, those vibrant blue eyes staring up at her as his head bobbed back and forth, "Sqlch! Squick! Glrck!"
"I know," she murmured as her hips rocked against his face, pushing deeper to hear the sounds of his strained throat, "it's scary but I didn't have you craft that perfect little ass not to show it off." Her fingers threaded through his hair as her balls started to lift in anticipation. "You'll make the team. Trust me," she promised as he felt her stretch the deepest recesses of his throat. His eyelashes fluttered as she dumped her thick heat into his belly.
So there he was, being led back to the locker rooms. A trio of giggling older girls walked before him. He could see their hips swaying side to side and felt a bit of pride that his hips and ass were the best of all of them. It also sent a tingle to his uncaged cock idly. That had been the biggest surprise. "I have another chastity cage on order and it should be arriving soon. It'll completely hide that worthless thing. However, I don't want the cage to ruin the lines of your skirt; it's pretty tight and the cage will stick out like a sore thumb. But by itself, that thing won't leave a dent at all," she said with her usual smirk, a sight that would have taken Alex's breath away if she hadn't already been pounding it out of him. His ankles were by his ears as she loomed above him, long-stroking inside him as he gasped and mewled his pleasure. Even if he was still caged, it did nothing to stop the relentless onslaught of pleasure as she ruthlessly steamrolled over the little fag-button inside him. Soon his meager load dripped from his cage to fill his belly button (and not much else) while she filled it from the inside with a roar of pleasure.
He entered the dark lockers, standing there meek and demure as the trio spun around on him. "Congratulations, Alex! You could potentially be the first freshman to ever make the squad! We'd love to have you out there with us to support the team. But there's only one test left. We have a tradition here: you try out for the team so the team tries out you!" the bubbly blonde told him. No sooner had those words left her heavily glossed lips than a dozen or more huge figures step out of the shadows. Alex was immediately surrounded by the hot sweaty figures of the football team fresh off the practice field. As he felt a pair of thick wet fingers push between his cheeks and slide easily into his rosy pink asshole, now he knew why they asked him to take off his panties.
"Of course! I'm ready to support the team any way I can!" he asserted as those fingers left him and his lithe body was hoisted up into the air. His eyelashes fluttered when he felt his body weight settle on a familiar shape pressed against his lubricated hole. He looked down to see another large black shaft slide under his tiny coinpurse. His eyes widened as the pressure between his cheeks suddenly doubled. "O-OH!" he gasped as he felt his hole stretch to accommodate both.
"Welcome to the team, Alex! Enjoy the tryout." said those glossy lips before leaving Alex to those hulking forms in the locker room."