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A Fitting For A Hairbrush

Charley gets a new hairbrush.
Charley’s first internet date with Abby, excuse me, Mistress Abby, was a disaster. He was looking for a strong good-looking woman, someone who would appreciate his body (he had no personality to speak of), and he found one. Strong was the operative word.

Abby was also very attractive and wore her clothes to accentuate her charms. Charley actually got so stiff when he first saw her that he was embarrassed at the expanding tent below his belt. Sexy and demanding too, Abby monopolized the conversation and told him exactly what to do. When he deviated slightly, Abby dropped his pants and took Charley over her lap and soundly spanked him.

This was not foreplay; Abby blistered his bottom. To bare himself this way was very humiliating; to say nothing of the terrible fires Abby set in his butt. Charley didn’t understand why that made his cock hard, but with his organ the size of a football, he needed some action.

Well, he did get some, sort of. Charley had to drop to his knees after removing his mistress’ panties. He was then ordered to massage her clit with his mouth! Charley knew she liked it when the hot streams of pussy juice hit his face. Her screams told him he did a nice job.

Charley was sent on his way with a wet face and a fully engorged, unattended to, penis. He was directed to call his mistress on Tuesday for further instructions.

Charley wasn’t sure if this was why he joined the dating service, but the chance of enjoying Abby’s great body overrode his thinking. Having seen his mistress’ uncovered body when he serviced her, and tasted her sweet honey pot, Charley wanted more. Maybe next time she would let him stick his swollen cock into her.

Charley’s buns burned all weekend, yet he couldn’t wait for Tuesday.

“Hello Mistress. This is Charley.”

“What do you want, you sniffing excuse for a man?”

“You instructed me to call today, Mistress.”

“Oh yes. You’re the one who cried like a baby when I spanked your cute ass on Friday. It was only a mild, first time, tune up hand spanking and you could hardly take it. I’ve spanked young girls who didn’t make half the noise! But I did enjoy watching your bare buns dance across my lap as they warmed up. Hope you enjoyed it as well.”

“I’m sorry Mistress, but you do spank very hard. May I see you again?”

“I have several other spankings scheduled for this week, but I can fit you in on Friday. Be here at 8 pm, and don’t be late! But first, you have to get your own hairbrush. All my boys have one.”

Why do I need a hairbrush, Mistress?Charley asked, already knowing the answer.

“Charley, you will go to ‘Amanda’s Beauty Salon’ for your hairbrush. They have a nice selection. Tell Miss Amanda I sent you.”

Abby’s hand, sharply spanking his bare buns, was difficult to endure, but now she wanted toast his butt with a hairbrush? Could he survive that? Having sex with this sensual woman would be great, but at what cost? Charley was thinking with his little head again.

Needless to say, his swollen cock won the argument and Charley found the salon. Upon entering, it looked like a regular beauty parlor, but he did see a few young men in the waiting area. Probably waiting for their wives, he surmised.

Finding a tall, stern looking, but attractive woman near the rear, Charley asked if she was Amanda.

“Yes, young man, what can I do for you?”

“I would like to see some hair … hair … hairbrushes,” he forced out.

“Will they be for grooming or training,” she smiled, as she pushed her well-formed tits in his face.

Charley got very stiff admiring this sensuous and well-dressed woman. She reminded him of his own Sweet Abby; dressed to show off her great body. Her short skirt and heels accentuated her long and firm legs. He couldn’t miss her chest and tried not to stare. He hoped she didn’t look below his waist and see him sticking out like a pole. Or maybe if she did, ... who knows?

As Charley continued stammering, Amanda said, “Come on boy, I don’t have all day. Will you be using it on your lady, or will it be warming your cute buns as you dance on her lap?”

Not being able to discuss this private and embarrassing matter with a strange woman, Charley just said, “Abby sent me.”

“You mean your mistress, you lucky boy. It isn’t everyone who gets to be spanked by such an expert, and a real beauty too. Come in the rear with me. We'll do a quick fitting for you.”

Amanda pushed the curtains aside and entered her stockroom. There were several long handled hairbrushes on the wall, of various sizes and shapes. Charley also noticed a sturdy wooden armless chair off to the side.

“Close the curtain behind you, boy. I’m sure you want some privacy for this.”

Amanda went to the wall and took four brushes down. She handed them to Charley and sat in the chair.

“Over here, boy, you know the position.”

“What are you doing? I didn’t come here for a spanking. Just sell me a hairbrush and I will be gone.” Charley regretted saying that as soon as it slipped out. One way or another, he knew his ass would pay for that remark.

“Your mistress told me you were a bit resistant. She will deal with your insolence. Why don’t you call Miss Abby and tell her you don’t want to be fitted. Or you can just drop your drawers and get this over with? Your choice, Pal.”

As Charley pondered his situation, Amanda hiked up her skirt to avoid any wrinkles. She was also fully aware that many times these bare assed young men shot a hot load of jism into her lap, and she had no time for that today.

“You can either buy all four, or I can see which is the proper size for your sorry ass.”

Afraid to defy Abby again, Charley approached Amanda and stood off to her right, holding two brushes in each hand. A small and a large one in his right hand, and two mid sized ones in the other. Those two were similar in head size, but one was round and the other oval.

“Let’s get your pants down and see which one is best for you.”

“But why my pants? Can’t you just measure them against my butt, Amanda?”

“Call Abby and ask her why, and you will address me as Miss Amanda.”

Resigning himself to another humiliating over the knee spanking, Charley just closed his eyes and said, “Yes, Miss Amanda.”

Soon Amanda had his belt open and his trousers sliding down his legs. Once they were in a puddle around his shoes, her thumbs went into the waistband of his boxers. They were soon hugging his knees. It was apparent Amanda had done this before, many times.

Charley opened his eyes and looked down at Amanda’s open cleavage and well formed thighs. They brought life to his penis and it stood up and looked around.

“None of that here unless you want a real spanking,” Amanda said as she pinched his erect organ.

Yow, Miss Amanda, please don’t do that.”

“Do you speak to your mistress like that? Now drape yourself boy, I have a business to run.”

Charley realized the door to the stockroom only had a curtain across it, albeit closed.

“I hope nobody comes in. Can’t we do this somewhere else?”

“It’s nothing the others haven’t seen before, but for that small cock of yours, or heard for that matter. If you don’t start moving, we will do this out front! The ladies would love a floor show.”

Charley, not being as dumb as he looked, leaned over the bare lap and hoped this wouldn’t take long. His semi erect member was pressed between Amanda’s warm thighs and his.

Amanda placed him into a proper position and asked for the smallest hairbrush.

Charley happily complied. With his hands and feet on the floor, Charley’s white ass cheeks rose high on the lap and smiled up at Amanda.

“We usually use this model on the young girls needing training, but we can try it on you first. Two rules: Keep your hands on the floor and no discharges. I am very firm about that.”

With that, Amanda gave Charley’s right cheek two smart cracks. Instantly two nice small pink ovals appeared next to each other.

“Ouch, I thought this was a fitting, Miss Amanda. That was pretty hard.”

“Are you telling me how to size a naughty bottom for a hairbrush? Abby’s boys are much better trained than that. I’ll have to talk to her about your attitude.”

She then delivered two more smacks on the other side, this time one above the other and somewhat harder than the first two.

Charley groaned but kept his opinions to himself.

Examining the four pink ovals, Amanda announced, “This one seems too small for your butt. Your mistress will need double the amount of spanks to cover your sorry ass. Let me have the nice mid sized oval one.”

“Please not so hard this time, Miss Amanda,” Charley said handing up the requested hairbrush.

Again, two smart spanks fell on his right cheek, this time leaving two larger imprints. “This seems much better, don’t you agree? Let me have the round one now.”

Charley exchanged brushes with the woman he could no longer see and soon thereafter felt two hot smacks on his left cheek.”

Yowee, Miss Amanda, that really stung.”

Besides coloring nicely, Charley twisted and rolled his buns over Miss Amanda’s lap. With his cock squeezed between both sets of warm thighs, Charley tried to hold off a cum. But just as with being spanked again, Charley realized he had no control over what the rolling pressure on his stiff member would cause.

“They’re both about the same size and nicely cover your butt. Which do you prefer, boy?”

“I don’t know, Miss Amanda, they both hurt.”

“OK, now hand up the larger one. May as well try it so long as your sorry ass is still in position. Not to worry; you need a good spanking for your behavior today.”

After eight strokes of the hairbrushes, Charley’s ass was throbbing, but he knew already not to resist these domineering women.

Amanda looked down at the bare and well-marked globes below her. She could clearly see the red imprints of the three different brushes that loudly cracked off Charley's ass. She glided her hand across both trembling ass cheeks and pressed a finger into the center of each mark.

Charley yelped at each one and kicked a leg out.

“Stop squirming, young man, I barely touched you. How does Abby deal with you? She may have to send you here for a few sessions to toughen you up.”

Amanda, now having the largest of the brushes, gave Charley a firm spank on each side of his steaming ass cheeks.

“Oww, oww, oweee. Please no more, Miss Amanda,” Charley cried out as he rolled his butt from side to side, hoping to fend off any more heat.

“Charley, from the outlines on your delightful butt, I think the oval hairbrush will suit you best. You can pick out any color you want. Maybe pink is best, since you cry like a little girl. It comes in ivory and mahogany, your choice.”

Charley tried to get up, but Amanda held him down.

“Just a quick inspection before you go, boy.”

Amanda ran her palm over both ass cheeks again, this time very slowly, not missing a spot. She even went between his cheeks to compare the white of the separation to the red of his butt.

Opening his cheeks with the fingers of her left hand, Amanda admired how his butt hole winked up at her and quivered. Amanda gave Charley's asshole a little tease with her right forefinger. Applying some pressure, it relaxed and Amanda slipped into the pink opening about an inch, wriggling her invasive digit back and forth. Charley didn’t like that at all, but besides twisting real hard and kicking his legs about, he was helpless to resist. Other than a “Please Miss Amanda, please stop that," Amanda owned his butt.

With his butt starting to feel the fires building up, Charley didn't need this extra attention. He continued fanning the heat, but all it did was make Amanda wet.

“Please Miss Amanda, my mistress spanked me only a few days ago and my butt really stings. Can you stop? Is my fitting over?”

"Yes Charley. You can get up now. I’ve had about all the crying I can take for one afternoon.” Before he did though, she wiped her finger on his shirt.

Charley stood up, trying to hide his frontage from Amanda’s view. It didn’t help, as she grabbed his extended penis with her left hand.

“I don’t know what Abby sees in you, boy. This is a poor excuse for a grown man. Maybe your mouth is better!”

Amanda felt the cock starting to swell and pulsate and didn't want any jism squirting onto her nice outfit. She gave Charley a hard pinch on the purple head of his tumescent organ and let him go.

Yoweee, that hurt, Miss Amanda.”

Charley pulled up his boxers and trousers and redid his belt, trying all the while to push down his flagpole erection. Amanda put the oval shaped hairbrush in some pink wrapping paper and then into a small bag. The bag announced “Amanda’s Accessories.”

“You may pay at the front.”

Charley made his way through the store and walked past several glum faced young men. The women there, in various stages of having their hair done, looked at each other and giggled. Charley tried to hide the bag behind him and walked out as fast as his stinging buns would allow.

Sitting in his car was not fun, but he finally got home and drew a cold bath, taking it on his knees, of course! Having today’s fitting on top of Friday’s hot spanking definitely had his ass cheeks blazing. He hoped his butt would be less pained by Friday, when he would get to see his Sweet Miss Abby again. His dick got hard just thinking about it.

Eventually Friday rolled around and Charley showered and dressed for his date. This time he put on some nice solid colored shorts, instead of the silly flowered ones he wore last week. Realizing he couldn’t take Amanda’s little bag into the street, he put it into a brown shopping bag and walked to his car. This time he would not be late. Miss Abby didn’t like that.

Soon he was knocking on her door. Abby opened it wearing a kimono that showed her long hose clad legs from the thighs down. Abby’s great tits pushed out the top of the wrap. Her black silk stockings and high heels got Charley’s juices flowing.

“I see it’s two minutes to eight, Charley. Isn’t it amazing what a little hand spanking will do for you?”

“Hello Mistress, it is so nice to see you again. You look lovely.”

“What’s in the brown bag Charley? Did you bring me a gift?”

“It’s the th … th ... thing I got at Miss Amanda’s, Mistress.”

Hoping the hairbrush would never have to be used, Charley nonetheless offered it up.

“Show it to me, you silly boy.”

Charley opened the bag and took out the gift bag with the pink writing that announced to all who saw it what was inside. Abby looked at the cute pink bag and brush, but dropped them back into the shopping bag.

“Charley, this is something to be very proud of. You must bring it each time you come here. Now go back to your car, leave the brown bag there and properly bring me your new hairbrush. Don’t take too long.”

Charley hid Amanda’s bag as long as he could, but once back at his car, he had no choice. He held the gift bag, which was conveniently a few inches too short for the hairbrush. For two blocks, Charley carried the small bag behind his back, but the few people he passed noticed the handle protruding and smiled at him.

Returning to Abby’s loft, Charley knocked on the door, and when it opened the lovely Miss Abby was not wearing the robe anymore. Abby’s long black stockings came high on her thighs. Above she wore the skimpiest of skirts, not much bigger than a handkerchief. It barely covered her pubic hairs. When it swished, Charley actually saw Abby’s well-trimmed bush. Panties were nowhere to be seen.

Then after a few inches of bare midriff, Abby wore something that merely pushed her full tits up and out. Her hair and face were perfectly made up and Charley’s cock jumped up.

Abby grabbed the protuberance and led Charley into her apt.

“I see you have a present for me Charley. That’s so nice. Is it something we can both enjoy?”

Pulling him to the couch by his cock, Abby asked Charley if he would like to kiss her breasts.

“Yes. Miss Abby. They are so beautiful,” he said, never having seen them bare before.

Last week Abby had freed her tits as Charley ate her clit. He missed the show, as his face was buried in her crotch.

“Then unzip my bustier and get them out. I wore this outfit for you, but it is rather confining. Be gentle with my nipples.”

Charley couldn’t believe the change in his luck. Finally going to make it with the lovely Miss Abby!

As her firm tits popped out, Abby put them in his face and opened his belt. When Charley’s pants fell to the floor, Abby entered his shorts and grabbed his ever so hard member and told him to go to work.

Between nibbling on those greats frontal globes and the massaging of his cock, Charley was afraid he would shoot his load too soon. Now that would be embarrassing!

Abby, feeling the monster throbbing, asked the delirious young man, “Charley, would you like to fuck me?”

Holding back the jism rising through his system, Charley thought he was in heaven.

“Yes Mistress. You are so desirable. May I?”

Pinching the erect organ very hard, Abby told him he hadn’t earned that right yet. "Maybe I will allow you that pleasure after we complete your training."

“Yow, Oh that hurts, Mistress. Did I displease you?”

‘Charley, I am very distressed over the report I received from Amanda. You were very disrespectful, defied her and totally embarrassed me. My boys don’t act like that. You apparently learned nothing from last week’s spanking.”

“Oh, I’m so sorry Mistress,” Charley sputtered as his pants covered his shoes again and his now limp cock hung in shame.

“Sorry doesn’t cut it, Charley. Go get the spanking chair and give me your new hairbrush. When you get back to me, make sure those boxers are gone as well. After we dispense another twenty-four, you can thank me for all of this time I am giving you!"”


Rickey Smarts © 2014

Does Charley ever get his wish to enjoy the luscious body of Miss Abby, or is this “date” just another excuse to get his still tender buns spanked, this time with his new hairbrush?

Care to wonder why Abby invited Charley back? Stay tuned as Mistress Abby takes Charley through his paces.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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