Will’s heels clicked over the wooden floor of his living room as he ran around setting up the christmas decorations. His sister Alice and her friend Liz would be back soon and he knew better than to upset them, after all, that is what had gotten him in this awful situation to begin with. A week earlier he had been caught with the panties of Liz, so the girls had decided that if he wanted Liz’s clothes so bad he could have them, they had superglued him into Liz’s tight latex mini dress and dropped him off at a college party with the promise that if he got a man to take “Willow” home, he would get the solvent. The hungry stares Will got from the guys and the grinding over their hard cocks he had to do on the dance floor had made him want to die, but before anything else could happen the party was cut short as the house owner’s parents had come home early from their trip and were obviously upset. Amidst the confusion, Will had slipped out the back and had made the walk of shame back to his house dressed like a latex stripper but ready to get the solvent.
However, the girls didn't feel like he had earned it. He hadn't gotten a man to take “Willow” home, so there was no deal. Will pleaded and kneeled before them on the verge of crying. he felt humiliated, dressed as a girl in full latex and begging his sister and her friend, but what choice did he have?. Upon seeing his pathetic display, Liz burst out laughing, further crushing his male pride.
“Okay Willow, I’ll tell you what, since you made me laugh I will let you out of that dress”, Will looked up, hopeful, “but Willow will have to make an appearance at next week’s christmas party”. Will’s heart sank, but he couldn't refuse, it was either dress up again or stay as he was.
“Great! oh, and just to make sure you don't try to back out last second, you will have to use something”. That something turned out to be a flat chastity cage, again, Will had no way of refusing and so Liz was the tasked with locking away his manhood, the cage was so tiny that it hurt poor Will. She then hung the key from her necklace like some sort of trophy. “See you next week, Willow!”.
Now as he prepared the house for the party, Will was having second thoughts, he had gotten his “clit” as his sister called it, caged, and he was back to being stuck in a dress!, not only that but this time he felt extra slutty; his red vinyl mini dress left nothing to the imagination and hugged every curve that Liz had crafted with the use of a corset, his white platform heels, courtesy of his sister, and red gloves only served to make him more feminine. Alice had even forced him to get fake tattoos, Will was nervous that people would think he was “that” kind of woman.
The doorbell rang and Will strutted over to open the door, it was hard to not shake his hips side to side with his current footwear. Alice and Liz greeted him and walk in followed by no less than 10 guys!. “Come on Willow, don't just stand there, greet our friends!” said Alice. Will did as instructed which meant he had to give each guy a kiss on the cheek with his cherry-red lips. He was afraid of what would happen if the guys found out he was a guy dressed as a woman, even in his heels they still were taller than Will, not to mention muscular.
“Willow!”, Liz called from the living room, “why don't you shake that little butt and get us some drinks?”. And so, Will spent the better part the night acting like a maid for the guests, each trip meant a smack or feel on the ass or a shot Liz would make him down so after a while Will himself was feeling dizzy. He didn't even notice when his sister and Alice disappeared each with a guy in tow, but he did notice the meaty hands that grabbed him by the waist and pulled him in to grind onto his girly ass. Will could clearly feel the outline of the guy’s erection pressing right into his buttcheeks which frightened him. However ,due to being drunk and stuck on the stupidly tall heels he wasn't able to run away. He spayed out his arms trying to balance and not fall forward as the guy humping his rear started to go faster. His manicured hands landed on the crotches of two guys now standing each at his side with a smirk on their face. A fourth man walked up to Will’s dolled up face, and the sound of three zippers being pulled down in unison filled the room. The guy humping Willow’s ass grunted and blew a white sticky load all over Will’s feminine ass and his back. With now four fully erect cocks surrounding him, “Willow” felt weak, vulnerable and scared. One thing was for sure, “she” was going to have a very white christmas.
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