Summary: Dean wakes up in quite a predicament after being knocked on the head by a mischievous poltergeist.
Disclaimer: This story is based on characters and situations created and owned by WB and Eric Kripke et al. No money is being made and no copyright or trademark infringement is intended.
Warnings: cross dressing, dubious consent
Author's Notes: Thanks to Soph for the beta. This is 21 out of 31 short fics, all involving masturbation in honour of the Merry Month of May. All fics were written with knowledge up to Hell House, no canon after that was used since that's as far as I've seen.
Word count: 1,635
Link: to other mmom fic
Dean woke up slowly and noted first that his head hurt. The second thing he noticed was that something was not right and the only thing he could come up with to explain why was the word 'draughty'. He took a moment to try and remember what had happened and as soon as he recalled something hitting him hard on the back of the head he sat up searching for his shot gun. He came to a horrified halt very quickly as he found out why it felt so breezy all of a sudden; he was wearing a dress.
Not an ordinary dress either, but a short, frilly blue dress with lace petticoats and knee socks. There was also nothing under the dress as a quick shift showed him by the absence of the feel of any material. If that wasn't bad enough his legs, his strong manly legs were completely hairless; some bastard had shaved his legs. If this was Sam's idea of a joke he was so dead he wouldn't even see it coming. Climbing to his feet he began swearing and taking in his surroundings at the same time.
He had been moved from where he had been attacked and from what he remembered of the layout of the house he was now in one of the back bedrooms downstairs. It was an old house, one that had been on the market for six months now and from which buyers were being frightened away. That was where Sam and Dean came in; someone on the staff at the realtors had known someone who had known someone who had called Dean. For once they weren't sneaking around; they had actually been hired.
Sam was off doing research and Dean had supposedly been doing an initial recon, but it seemed the resident poltergeist had had other ideas. If any other poor bastard had ended up like Dean he could see why the realtors were having trouble shifting the place.
He tried the door and was not surprised to find it locked. It was at this point he noticed the painted nails. His nails had been neatly filed and all painted a bright, cheerful red, at which point Dean had an awful thought. He walked to the vanity table that had a small mirror on it and he looked at his face; sure enough that hadn't escaped either. Whatever the poltergeist wanted it sure was a dab hand with a razor, because the five o'clock shadow he'd been sporting all day because he hadn't been bothered to shave that morning was gone and he'd been made up. There was kohl around his eyes and lipstick that matched the nail polish on his lips. He reached for one of the Kleenex on the table without even thinking about it.
Even as he brought it towards his face it was snatched out of his hand by an invisible force. Dean glanced around the room, but nothing else was moving.
"I am not your dress-up doll," he said pointedly and reached for another Kleenex.
This time the whole box flew off the dresser.
Dean was just about ready to rant at the entity that seemed to think he was a play thing when he felt something flutter against his knees. He looked down, still disturbed by the fact that there was a skirt in his line of vision to find that there was a pink, silk scarf hanging in mid air just at knee height. That was odd even for some of the things Dean had seen in his lifetime.
When the scarf darted between his legs and then snaked round one, heading upwards Dean was so shocked he just stood there and when the silk dragged across his balls he had to grab the vanity table to prevent his legs buckling. It dawned on him slowly that he was being molested by a poltergeist.
"Kinky, son of a bitch," he said and unceremoniously reached under the skirt to removed the scarf.
In an instant it was twisted round his cock and balls and tightening dangerously. Dean was not stupid and he lifted his hands away rapidly, feeling the tension go out of the silk as soon as he did. The scarf started moving again and he felt his knees going weak; it seemed he was stuck with a horny poltergeist with a kink for cross dressing who did not understand the word 'no'.
He would have protested more if every move of the scarf hadn't been reducing his brain power by exponential increments. It was so not his fault he was hardwired to his cock. Despite his initial protest Dean was hard and aching in less than a minute and considering the alternative was castration it seemed like a good idea to just enjoy what he could until an escape route presented itself. Dean could cope with kinky; it wasn't as if he hadn't indulged a few of his own from time to time.
When he found himself being urged to move by the invisible force in the room, he went and he felt a little nervous as he was pushed over the arm of a chair so that he was lying across it on his front, but the scarf was still doing its work and he couldn't complain that it didn't feel good. When the skirt was lifted up and over his backside he decided that his first assessment had been right; the room was very draughty.
Now Dean had been on the receiving end of a strap on in his time; he was willing to try anything once and in this case he'd been back for more, so he knew the sensation of something pushing at his ass. It was a lubricated something and he had no idea what it was, but it was hard and cold as it breached him and he was left gasping. The object was not large so it did not hurt him, but it sure as hell felt weird, especially when it began to move in synchronisation with the scarf.
There were worse things than being molested by a spook, Dean had to admit that as his captor began to blow his mind. The first time the intrusion in his ass hit the sweet spot he almost came and he could have sworn he heard faint laughter. If he hadn't been so turned on his might have been embarrassed.
The poltergeist upped the ante after than and Dean found himself moaning and writhing as he was tortuously brought to the edge several times and then denied the prize. He could give credit where it was due; his captor was good at this. Finally, after what could have been anything from minutes to eternity, the devices of his torture were employed to their full potential and this time it did not stop. Dean did not even try to control himself and he came with a shout that he was not sure was actually in English.
He collapsed in a post orgasm heap and tried very hard to put two thoughts together. The poltergeist, whoever it may have been, definitely knew what it was doing; he felt as if he had no brain cells left after the explosion that had taken over his whole body. Maybe he could forgive the knee socks for an orgasm like that, but there was no way he was going to forgive the dress or the shaving.
He was beginning to recover enough to think about more than his cock when he felt something sliding up his leg. He looked down to see another silk scarf making its way under his petticoats and he couldn't help himself; he panicked.
"Oh, hell no," he said and with a supreme effort of will he surged to his feet and took a running jump at the nearest window.
Smashing through he landed and rolled, not really caring if he'd done any damage on the glass, just very glad to be out of that house.
"Bastard, perverted, sick spook," he snarled to himself until his eyes landed on a pair of shoes and he fell silent.
Praying to god for some random stranger he could placate with a ridiculous story he worked his way up from the all too familiar shoes until he reached Sam's shocked face. He had to really be working through some bad karma today.
"Dean?" his brother said, clearly stunned.
Dean pulled himself to his full height and tried to look as dignified as possible, which, considering his outfit, was a feat in itself.
"Not one word, Sam," he said pointedly, "not one little word or I'll castrate you with a silk scarf. We have an exorcism to deal with."
He stalked past Sam towards where he had parked the car, very glad that there was a spare set of clothes in the trunk.
"Like the socks, Dean."
It was clear from Sam's voice that his brother had been completely unable to resist and when the laughing started Dean almost decided that shooting Sam would be quicker than anything else.
"Maybe you could wear the dress to give the clients the good news once we've cleaned house?"
Sam appeared to be finding the whole situation completely hysterical. Dean turned and gave his best death glare and then he changed his mind.
"Sammy, if anyone's wearing the dress it's you," he said changing his expression into a nasty grin, "you being the girl in this relationship an' all."
As calculated that stopped the laughter as Sam spluttered at the implication; it was just too easy. With renewed confidence Dean turned back to the car; maybe he could leave Sam in the house for a bit before they finished the exorcism; with that hair Sammy would probably come out with pigtails.