Prom Mischief

"Mischief, thou art afoot. Take what course thou wilt." - Julius Ceasar, Act III, scene ii

Transcript: Could his day get any worse? Jack didn’t dare ask. Behind his convincing forced smile, Jack was seething.

His step-sister Brianna must’ve cheated, but he couldn’t prove it, and now here he was, stuck in a nightmare, all because of a stupid bet. It had been supposed to be surefire way to guarantee that Kelly, the hottest girl in school and his sister’s best friend, would be his date for prom. Instead, Brianna had won the right to choose a prom date for him! But that wasn’t even the half of it. Brianna had had the gall to pick Brant, varsity wide receiver and Kelly’s ex boyfriend as Jack’s date.

It was outrageous: two guys going to prom together? Jack had given Kelly an earful, but now, he just wished he’d kept his mouth shut. Brianna’s simple solution? Jack was to become Jacqueline, Brianna’s hot cousin from out of town. 

Brianna had also wasted no time and spared no expense in carrying out her wicked plan, which included inviting Kelly over and divulging the embarrassing details of Jack’s predicament to her. Prom morning, the girls had stripped him naked and shaved him unimaginably smooth, then painted his face with layers upon layers of makeup and styled his silky extensions, failing miserably all the while to suppress their giggle fits. When Brianna had unveiled the breast forms, Jack knew that Brianna and Kelly must’ve planned this far in advance. The forms were a perfect fit—a little concealer hid the seams—and it was impossible to tell he hadn’t been born with them. It had been horrifying for Jack to watch. The girls had even managed to tuck and tape back his dick so that it looked like he didn’t have one, even when wearing only the tight little panties they’d made him wear!  The tuck process in and of itself was a whole other debacle.


When it’d come time to hide his manhood, the girls had discovered that Jack was embarrassingly hard. After conferring privately for a short while, Kelly had surprised Jack by taking Jack’s cock into her mouth and masterfully using her sensuous lips and tongue to suck Jack off…over and over and over again until he was as limp as a noodle. Under any other circumstance, having his dream girl on her knees sucking him off would’ve been a fantasy come to life, but the whole experience was so horrendously humiliating that he couldn’t even enjoy it. Of course, Brianna’s snark comments hadn’t helped: at least with your balls drained, you won’t be having any ‘accidents’ when things start to get hot and heavy between you and Brant tonight, she’d teased.

A very tight but well concealed corset later, the dress, one of Briana’s old ones, had come to fit Jack perfectly. It was just the sort of dress that accented all the assets Jack wanted to hide, the type that would draw lots of unwanted attention from the boys. As reluctant as Jack was to believe it, Kelly and Briana had worked wonders and he not only looked believably like a girl, but a pretty one too.

The girls only had had only one more article for him after that before Brant arrived to pick him up: a purse filled with the usual assortment of feminine items, as well as a few condoms and a relatively humongous bottle of a water based lubricant—so the lube wouldn’t degrade the latex, Briana and Kelly had informed him with a snicker. Of course, the girls never expected to discover all the condoms missing or a completely empty bottle in ‘Jacqueline’s’ purse the next morning. But that wasn’t a bad thing. It just meant that the girls would have to go buy a few more bottles before they could continue with the next phase of their plan...