When I Was a Girl (part 1) by ShadowJack
Poor Timothy! He was just starting to get comfortable going out as a girl. He’d go to the mall, where he started hanging around with a gang of mall-rats. He dealt with the boys’ advances by sucking them off in the janitor’s closet so they wouldn’t learn his secret, but soon he was sucking all five of them. The girls in the gang didn’t care for that, and arranged a bit of revenge. They set up a group photo of the whole gang, with Tim in the front row. Just before the shutter clicked, they flipped up his skirt, yanked down his panties, and held up a big “slut” sign above his head. The photo revealed more than they’d thought it would!
Tim fled the mall never to return, but the photo went viral. It turned up in the hands of a guy who’d been bullying Tim for years, who threatened to expose Tim’s secret to the whole school. Tim had to do whatever the bully wanted. What did he want? Tim was going to have to dress up as a girl for him and his friends every week until they graduated.
The bullies had planned on just humiliating Tim, but when they saw how hot he looked as a girl, well, other ideas came to mind…
Ron and his buddies soon had Tim coming to their clubhouse, a low-rent warehouse unit in the industrial zone, twice a week. Tim showed up in his well-practiced girl persona, dressed to the nines, only to be humiliated, stripped and used. Usually it began with demands that he suck their cocks, but before long the horny, impatient bullies would be taking turns pumping Tim’s tight bottom-hole as well.
Tim told himself that he was only going along with their abuse because he didn’t want that incriminating photo to ruin his last few months of high school, but he often found himself daydreaming in class about what he would wear to the next debauchery and what Ron and his crew might do to him.
Then, one Saturday night after Tim had sucked off all four of them, the bullies tied him up in nothing but his stockings and told him they had guests arriving soon to fuck him. The “guests,” it turned out, were just random guys that the bullies had brought in off the street, guys who were willing to pay fifty bucks to fuck a naked sissy-boy.
One after another, they lined up to use Tim’s helpless body. Each in his turn, the faceless strangers thrust their hard cocks up into Tim’s ass, plunging his hot bowels with a sense of desperation until they had added another load of semen to the soup inside him. Some turned their faces away in revulsion, some closed their eyes and pretended he was a girl, and some groped his stiff little penis with thick, calloused fingers while they pounded him from behind.
Despite his desperate shrieks and squeals and intermittent tears, Tim came three times during the seemingly endless interlude. While most of the men were quick, hard and brutal, there were occasional moments of tenderness, too…