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Author's Note: A short story I wrote a while back, hope people enjoy it! I know it could be longer and more detailed, but i quite liked keeping it short.
malcom stood outside the bar for a moment composing himself, his nerves were threatening to consume him and ruin what had been months in the making. One of his hands unconsciously fell to his side, tracing the strap of the suspender belt he had been commanded to wear that evening. His instructions from Mistress were clear, go into the bar a 7pm sharpe, find a free table, order a lemonade and wait. With a sigh he walked into the bar and followed Her commands, his cock straining in the plastic chastity cage that had gripped it for the past month, denying him release from the sexual frustration he bore.
It was nearly six months ago that Mistress came into his life via a blog, and tonight was the night he would finally meet her in person.
Six months ago malcom didn't even own a pair of girly panties, now his collection of lingerie out numbers his boy clothes ten to one. It was Mistress who pushed him to buying his first thong and he remembers the night she made him parade in front of his webcam in them for her.
He spent the whole of the following day at work wearing it as instructed, unable to concentrate on anything as he counted down the clock until he could run home to his PC and his online Mistress. That night he masturbated as she watched for the first time, his tiny cock spurting small globs of cum over his desk as she chuckled away.
He didn't resist when she commanded him to lick it up, his Mistress knew what was best for him.
From then on his collection grew rapidly, Mistress pushed him on and before long malcom was only wearing lingerie, his old boy things resigned to the back of his wardrobe. Panties, suspenders, stockings, and bra's during the day, skimpy nighties and babydolls at night. He confided all his fantasies to his Mistress, She and She alone understood him.
Mistress didn't stop with the underwear, she pushed him into getting his cock pierced after he confided it was a fantasy of his, all he needed was her firm guidance and before long a thick metal ring hung from the tip of his small cock.
Mistress made him start waxing his body, removing the light hair that used to cover it, and through all this malcom had never seen her face one, only heard her commanding voice. It was a month ago that she finally said she wanted to meet in person, but there were to be conditions. The next day a package turned up with instructions, and to his surprise a plastic chastity belt.
His hands shook as he pulled it out, it was another of his fantasies that he had recently revealed to Mistress. That night she watched as he masturbated for her as normal, and once his cock was flaccid she instructed him how to fit the cage. As the lock clicked shut he realised that from this point onwards, a face to face meeting with his Mistress was inevitable.
For the next month Mistress teased him about a meeting date, he grew increasingly frustrated as the chastity belt worked its magic and before long he was willing to do anything.
malcom sipped on the lemonade as he surveyed the quiet bar. He wondered why Mistress had picked this bar, it seemed a odd place somehow, and was really quiet. It had been an hour, but her instructions were clear.
'Wait for my instructions.'
A tall, slightly chubby blonde woman finally came over to him after 2 hours and smiled gently. "Follow me malcom".
"M-m-mistress?' he stammered. She wasn't what he expected at all.
The woman chuckled and shook her head "I'm not your Mistress malcom, but she has left me clear instructions to follow so hurry up."
The mystery woman led malcom out the back of the bar carrying a small bag, into a private room. malcom looked around to see a number of comfy armchairs laid out in a semi circle around a small platform. She put down the tray and pointed at the platform. "strip on there sissy, down to your undies. Your Mistress tells me you have quite the sexy body."
He looked up shocked, but he dared not go against his Mistress's wishes so he slowly pealed away the shell of clothes that hid his true nature. She handed him a pair of extreme high healed ballet boots that would make malcom totter on tip toe like a ballerina and watched as he put them on. She handed him the padlocks that clicked through the buckles of each boot, securing them in place.
His cock strained against its cage as the woman produced more items from her bag, picking up a set of small ear plugs. As she squeezed them into place Malcolm's world went quiet. Next up was a shining latex hood that she motioned for malcom pull over his head. It had no holes to see, only two small air vents over each nostril, and a hole over his mouth. Now blind and mostly deaf Malcolm's cock was even more energetic in its futile attempts to become erect and he gasped as the woman pushed something into his mouth.
He groaned in discomfort as the ring gag was put in place, securing his mouth wide open. She pulled his arms behind his back and pushed his palms together, malcom didn't dare move them as she worked something up trapping his arms. He grunted as he figured out what was going on, the arm binder tightened until his elbows touched. Finally malcom felt something heavy wrap around his neck before he was pushed to his knee's. The end of the arm binder must have been secured to the floor as he could no longer stand, then malcom felt nothing.
It was an age later that malcom felt a hand brush across his head, he groaned in response but his sounds were soon further muffled as his face was pulled into the naked sex of a woman. Malcoms tongue automatically darted out, he had never done this before but had always dreamed of it. He hope it was his Mistress, and he tried his best as the woman ground her sex into his face. As she came his face was pulled in so tight he struggled to breath, but in his position he couldn't struggle agains the two hands holding his head.
Just as he thought he would pass out the woman let go, and malcom gasped as he tried to recover his breath. He felt someone else grab him, and flinched as the flaccid cock was pushed into his mouth. He tried to pulled away but once again his position made it impossible. The man face fucked malcom, his cock growing in width and length until malcom was chocking and gagging on it. With one huge thrust the man buried the entire length of his cock into Maclom's throat, and he felt the first spurt of cum his the back of his throat. The man held his cock in place as he deposited his huge load into malcom, only pulling out when he was finished. malcom coughed and spluttered once more, but his torment was not over yet.
He felt the end of the arm binder being unclipped from the floor before it was hoisted high into the air, pushing him over. He moaned as something was pushed into his arse, something rubbery that extended deep into his virgin anus. He screamed as it started to inflate, and just as he felt he would rip in two it stopped. He felt like a beach ball had been inflated inside him, and try as he did the thing wasn't going to be pushed out.
Suddenly his insides started to flood with a warm solution, as as the first cramp hit him another cock was pushed into his mouth. By the time the next man came in his mouth the fluid had completely filled his insides, and the cramps ripped across his bowels. He felt someone fiddle with the lock on his chastity belt, his Mistress was here!
He groaned loudly as it was taken off but the pain from the enema meant his tiny cock hung limp. He felt his piercing being removed, before cold metal was pressed to his skin. He felt a new device being fitted to his cock, it was far tighter than the plastic cage and it threaded through his piercing. With his cock once again locked away Malcolm's hands were released and he was pulled back to a sitting position. He felt the bowl beneath his bottom as the enema tube was deflated and quickly pulled, the fouls stench of his shit mixed with the enema filled his nostrils.
Malcom received two more emena's, and was in the middle of pleasuring a woman when he felt something else push against his rear. The man's cock slid deep into him and started fucking his arse without consideration. The woman came fast, seemingly spurred on by the sight of the man fucking malcom and soon moved away. The man suddenly pulled out of malcom and grabbed his head, pulling it back. The mans's cock was thrust into Malcolm's mouth just in time to catch the first spurt of the man's cum. Malcom could taste the salty load, mixed with the juices from his own arse as he chocked on the load.
After being used five more times malcom was exhausted and sore, the last man hadn't pulled out and instead had deposited his cum deep in Malcolm's arse, which was currently dribbling down his inner leg. Hanging in his bonds he suddenly felt very alone, it had been a while since anyone had touched him and he wondered why they had stopped.
An age later hands returned, and he felt the bonds being taken off once more. The mystery woman appeared, smiling at him. "Someone had fun with you didn't they!" she said. malcom looked around, the room was as empty as it was when he walked in. The woman pushed the gag back into his mouth and clicked another padlock closed.
"iiisshhhtresssshh?" he said, gagged.
"She's gone, but left you this note." the woman said. "Take your time to get dressed, your Mistress left you something clean at least." the woman pointed towards a small pile of clothes.
The woman walked off, leaving malcom alone in the room holding the note. The collar and boots were still locked in place with small combination locks and malcom quickly opened the note up.
'Slave,
Your performance tonight was pitiful, you are terrible at giving satisfactory blow jobs to my lovers and your pussy licking leaves much to be desired. The only saving grace is that you have, what I'm told is a very fuckable behind.
You will notice that I have upgraded your chastity belt to a far more secure Lori device. I, and I along hold the key to that device so I suggest you work on pleasing me if you want to ever cum again.
You will put the clothes on I have left you and go home, the combinations to the locks will be emailed to you later. I will send you more instructions tomorrow.
Mistress'
Malcom read the note three times, downhearted. Mistress was disappointed in him and that hurt more that the enema or anything else that had been done to him that night. He vowed to try harder, follow her instructions and one day please her enough to see her divine face.
He went over and picked up the clothes, blushing as he read the writing on the skimpy dress that had been left for him. 'Cum whore' was written on the front of the black dress, and 'ask me how much' on the back. Malcom panicked, there was no way he could wear this but after looking around her realised he had no choice. The only thing he found was the key to his apartment, everything else had been taken.
He pulled the dress up and slid his arms in, the straps of his bra clearly visible as was the tops of his stockings and suspenders. What was more embarrassing was the fact the dress was so short, his tiny, caged cock was clearly viable. He knew he had no choice, and as he tottered towards the door his cock strained against it's new cage. malcom felt the tighter grip of his new prison, and longed for the comparative freedom of the other cage. His cock could barely twich in this device it was that tight.
He opened the door and was greeted by a far different sight in the bar. It was packed, the music was pumping and currently up on stage a partly naked man was stripping and being cheered.
malcom gasped as he twigged what type of bar this is, and tried to turn but two of the men stood closest to him had all ready spotted him. Hands shot out and grabbed him, pulling him towards the stage as the music shut off and the male stripper made way. malcom was pushed onto the stage and felt someone grab his hands, pulling them behind him. He heard the duct tape as it was wound round and round his wrists but all he could do was stare out at the crowd of men.
"Blow jobs 5 buck, arse fucking 10!" the man shouted behind malcom. "Who's first?"
malcom saw a sea of hands jump in the air and groaned, his night was far from over. "Still he thought to himself, at least its practice for Mistress...."