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Jimmy came into Aunt Polly's kitchen to find a plate of homemade chocolate chip cookies and a big glass of milk waiting for him.
"Hi Aunt Polly. Thanks. I love your cookies."
"Well go ahead and eat some but don't spoil your dinner appetite"
Polly was a woman in her late forties. A solid woman with a large bosom. Her hair was brown with streaks of grey she did not care to color. She was a strong woman who took usually had her way. After Jimmy had eaten his third cookie and drank half the milk she said;
"Jimmy, I asked you to come over today because we have something important to talk about."
This made him stop chewing and stare down at the plate in front of him. He said nothing.
"You know what I am talking about don't you?" He said nothing.
She repeated the question and he finally mumbled out a "No," but he said it with little conviction.
"We know you have been taking your sisters dirty panties from the hamper and wearing them. Is this not true?"
Once again he mumbled out a "No."
"We know it has been going on for some time and we hoped you would grow out of it but it doesn't appear you will so we have decided to try to break you of that habit."
He then exploded in a stream of denial. This isn't true. His sister and mother are liars etc. Polly let him go on until he ran out of breath. When he did she asked him;
"Are you wearing a pair of them now?"
"No. I don't wear..."
Before he could finish Aunt Polly came around behind him. With her right hand she grabbed his shoulder and bent him forward and with the left she reached into the back of his pants and fished around until she found the waistband of the underwear he was wearing and pulled it up to expose the stretchy pink material of a pair of very lacy panties.
"What do you call these?"
He said nothing. He didn't know what was going to come next but he was aware of Aunt Polly's resoluteness.
"You have committed three transgressions, haven't you?"
He looked at her and said "three?"
"Yes. Three, First you stole these panties from your sister. Dirty panties at that. Next you wore them, deriving some sick little pleasure out of them. And finally you lied to me about them. I do not like being lied to. Three transgressions three punishments. Let's start with the lie."
Polly did not give him a chance to reply. She grabbed him by the arm and pushed him into the bathroom. Jimmy offered no resistance. Once in there she sat him down on the toilet seat and reached into the shower removing a bar of soap from the dish. It was half gone and an image of Aunt Polly washing her naked body with it lept into his mind. He knew what was coming next. He shuddered as he noticed a small curly hair in bedded in the soap.
"Open," she said as she held the bar in front of his mouth. When he didn't she grabbed his ear and twisted until he cried out. She than shoved the bar into his mouth and held it there, moving it around to cause maximum displeasure.
"Will you ever lie to me again?"
"No," he said as best he could.
"Will you lie to anyone?"
Once again he mumbled out a no. She left the bar in his mouth for over a minute before removing it.
"May I spit this out?" he asked pathetically.
"No," Polly said, "I think you should swallow it". He choked it down.
Come with me," she said walking out the bathroom door. He needed no encouragement. He was fully submissive now. She lead him into the bedroom.
"Since you like wearing woman's panties I am sure you will like this."
On the bed displayed in front of him was a full set of woman's clothing. Or to more precise a a school girls uniform. There was a plaid wool skirt, a white blouse and red sweater vest. There was also a bra, a white full slip with a lacy bodice and a pair of knee high white socks.
"Take off your boy clothes and put these on."
Putting these on in front of her would be humiliating but he did love the idea. He tried not to show too much excitement as he removed his clothes.
"Keep the panties on. Put on the bra first."
He put the bra on backwards, connected the two ends and then turned it around properly. Polly noted this and knew this wasn't his first bra. Next Jimmy picked up the slip. Its silky touch excited him all the more as he slipped it on over his head. The feeling for him was glorious. Next he put on the blouse then the skirt and socks. When he was finished Polly handed him a pair of black patent leather Mary Janes to complete the outfit.
"Stand up in front of me" Aunt Polly said. When he did she took a small golden tube and applied a pink lipstick on him. One appropriate for a young girl.
"Now go stand in front of the mirror."
There was a three-way mirror in the corner of the room. He went in stood in front of the mirror.
"Do you think you make a pretty girl?"
"No Aunt Polly."
"I think you look ridiculous. You are a boy wearing panties and a bra. Your lips have pink lipstick. What kind of man likes doing that? Tell me."
"I I I don't know."
"Well I think you can stand there for the next hour and contemplate that answer." She then went across the room and sat in a chair and read a book. And she did make him stand there for an hour.
His legs were getting tired when she said "Now we will deal with the stealing. Come here."
He turned from his image in the mirror and came over to where she was sitting. She had put down her book and had picked up a 18" long wooden ruler. "Lie across my lap."
"Please Aunt Polly. I have learned my lesson and will never take her panties or wear them ever again. Please don't spank me." His voice was once again pathetic.
"You are going to get 25 swats. If you are not over my lap by the time I count to three I will give you 50. Even if I have to tie you down. 1."
By time she said 2 he was positioning himself over her lap. She took her time getting him the way she wanted. When he was how she wanted him she lifted up the skirt and pulled down the pink panties exposing his bare butt. "Count them." She wasted no time and brought the ruler down hard on the bare flesh.
"Oh." It was worse than he imagined.
"You didn't count so that didn't count. Start from the 1. And she brought the ruler down again.
"Ahhh." Then he said "one".
The second came down from a different angle forming an X shape red mark with the first."
The third, fourth and fifth were delivered as to form horizontal stripes across his ass. With each blow his pronunciation got worse. By ten she could merely make out the number of syllables. By twenty it was just grunts. She stopped then and gave him a chance to catch his breath (and to contemplate the final smacks). And then she delivered them. They were the hardest of the day. Each one in rapid succession.
Somewhere in his brain he was able to think that he was done. "Thank God," he thought, He did not think he could have taken anymore. She gave him a push and he crawled off her lap and onto the floor on all fours.
After a second she told him to stand. When he did she told him to "Lift up your skirt."
"W w why?"
She brandished the ruler and said "Do you want 25 more?"
Jimmy very reluctantly pulled up the skirt and exposed a hard cock straining against the pink material. There was a large wet spot growing in the center,
"You're a disgusting little pig. What was it the pain, the humiliation or rubbing your little tail against my thighs. I thought we were done but I guess not." And while ignoring his pleads for no more she grabbed his arm, spun him around, pulled his wrist behind his back and tied a scarf around them in a tight knot. She then pulled his panties down to his ankles
"Wait here," she said and went back to the bathroom, re-emerging a few seconds later with a tube in her hand. He recognized the label. Icy Hot. "Oh God!" he thought.
She had put on a latex glove and squeezed a large handful of the unguent onto her palm and then grabbed his erection and smeared it all over his cock and balls. When she was satisfied that she had the coverage she wanted she basically knocked him down onto his back and put her heavy foot on his chest. He was totally trapped.
"If you start making noise I will I will shove those dirty panties into your mouth." And then they both waited. It did not take long.
At first the sensation was pleasant. It was like a cool breeze. But soon the breeze became very gentle pin prick, but the pin prick kept getting stronger and hotter and soon there were no more pin prick but just ever growing heat. He was unaware of how long it took to peak and how long the near unbearable pain went on but somewhere along the line Aunt Polly kept her word and removed his panties and shoved them in his mouth.
Eventually the fire went out leaving a sore itchy member behind. Polly let him up and allowed him to clean up and get dressed. When he was ready to leave Aunt Polly pulled him into her large breast and whispered;
"You know I did this because I care about you."
"Yes I know," he said burrowing his face into the warmth and softness of her flesh. Her dress was low-cut and she wore no bra. She allowed him to work out her nipple and draw it into his mouth, suckling contentedly.
"Did you put the panties back on?" she said.
"Yes Aunt Polly."
"Then we are not done." She lead him to the door. "I will be in touch."
James Stickly was impeccably dressed when he emerged from the apartment. He was a wealthy and important man. His driver having been texted by Polly had the car waiting. He slid into the backseat and felt the soft leather seat of the Bentley envelope his battered bottom.
"Is the plane ready Roger?"
"Yes sir. I just spoke with the pilot. The jet is gassed up, checks are done and food and drink is onboard. The pilot has submitted the flight plan for Zurich."
"Thank you Roger." Mr. Stickly was always polite with staff. "I will be returning probably on Monday depending how the negotiations go. I'll let you know when to pick me up."
"Yes Sir."
And then he fell silent.
"Zurich," he thought. "Good." The negotiations were all but concluded, he would be in and out in a few hours, hopefully after a good meal. He would need it. He knew a Russian couple in Zurich that ran a private prison in the countryside. They would keep him naked and bound for three days. Feeding him bread and water and an occasional gruel of some sort. He would be locked in small cages and kept in stressful bondage. He would undergo a long, painful integration that he would be unable to answer any of the questions. He would be waking in the middle of the night for floggings and probably rape.
James Stickly was a wealthy and important man and men like him can always get what they need.