Sissy's Lot

 This is a commission I did for DeviantArt

Michael strutted onto the stage in the town hall with an unusual air of confidence for the occasion. The town's traditional annual Halloween costume auction was typically a bit of a crap-shoot for its volunteers, particularly the male ones. Every year, a selection of locals would sell their dignity to the highest bidder, who would give their bid to a worthy charity in exchange for choosing that year's Halloween costume for their lot. Finding volunteers had become increasingly tough after a few particularly brutal selections in recent years so anyone willing to put their neck, and the rest of their body, on the line would earn social currency within the community.

Social currency Michael badly needed after his recent divorce from local good-girl Sara – hence his agreement to volunteer for this year's auction. However, Michael had a plan. Michael had Roger, who had agreed to outbid any humiliating costume with something much more manly.

The auction started slowly – a buck to be Dracula, a couple to be Frankenstein. When a bid of eight nominated a cheerleading outfit, Michael nodded to his friend and Roger instantly bid ten dollars for him to be a biker. Michael rolled his eyes. Couldn't he have gone with something a bit less Village People...? The bids came in thick and fast after that – twenty to be a ballerina, thirty to be a belly dancer, fifty to be a princess. Sara and her friends had walked in directly from the bar next door and were drunkenly competing with each other to craft the most humiliating costume. Michael glanced to Roger in panic, but his friend had averted his eyes in despair – the going now far too rich for the small roll of bills in his pocket. The total spiralled upwards until finally Michael's fate was sealed with a winning bid of $200 from Sara's best friend, Steph, to spend Halloween dressed as a French Maid.

Needless to say, Michael didn't go trick or treating. When he arrived at Steph's house for his transformation, Sara and the rest of their friend group were already there. They took great pleasure dolling him up in a tiny maid's outfit and elbow length gloves. They waxed his body and painted his face with seemingly endless layers of makeup before putting a wig on his head that smelled suspiciously of glue. The rest of the evening became a shameless celebration in honor of Sara's divorce from him. He was made to crawl around on his hands and knees serving the women drinks and every so often Steph would draw everyone's attention and have an auction of her own. The friends would bid on giving him a spanking, having their toes sucked and even one particularly lucrative lot that resulted in him leaving a lipstick mark on Sara's bare ass cheek. The longer the party went, the drunker the women got and soon he was also answering the door to trick or treaters.

At some point around midnight, Sara gave him a long drunken look and smirked. “I never had this much fun with you when we were together. Fortunately, marriage can end, but blackmail evidence...now that's forever!”