CHAPTER ONE

Libby Livingston bit her tongue as Pepper turned the pages of the diary. Abstractedly, Pepper toyed with a raven curl, and once or twice the beautiful lips showed some ghost of a smile.

 

Oh, God, Libby thought. Oh, Jesus, Pepper's going to think I'm some sick pervert...and she might tell Ted!

 

After all for years, the two had been in intense competition for Ted Sansalone's affections...would Pepper take advantage?

 

But as Libby bit her lip, watching Pepper's full breasts bounce against her pink tank top as she read the sordid journal, Libby wondered: Is it Pepper who I love? After all...

 

Pepper finally slammed the diary shut and looked at Libby, and mercifully, she was smiling. A pink tongue darted out between Pepper's lips, which seemed a good sign.

 

"So, I know it's goofy, Pepper" Libby said hurriedly, as she stared at the floor.

 

 "I--I have these weird fantasies, and I just needed to tell you. But we don't ever have to mention it again, y'know? I just-just couldn't hold it in any more."

Libby was sweating slightly under her auburn mop…she wondered what was next… would she lose her best friend?

 

Finally, Pepper spoke. "So, you--you fantasize about me giving you spankings and being your life-coach or something?"

 

Libby nodded, blushing more. Pepper was quiet again, which made Libby VERY nervous. Pepper usually did 70 percent of the conversation!

 

It was too weird. They were quite competitive, these girls, and not just about Ted. Libby and Pepper were two of the prettiest girls at Westerly High.

 

Libby was better known for her athletic abilities, where Pepper was a sort of fashionista clothes horse, but they both were quite popular, and in spite of the competition, best friends.

 

Would that end? What would Pepper say next?

 

Libby looked up at Pepper, who had a Cheshire cat smile on her face. "So, what would I spank you with? My hand?"

As Pepper said this, she looked at her beautifully manicured little hand with some horror.

"I mean...that big ol' butt of yours, Libby, it might be too much."

 

Libby felt herself bridling; the old competition was there...

"No, Pepper, but my butt isn't any bigger than yours is, and I think you know that! No, my mom used to use a hairbrush on me."

 

Libby now kind of hoped Pepper would drop the topic. Obviously, Pepper was just going to be a bitch about this...and make fun of poor Libby.

 

Pepper tossed her dark hair and crossed her long legs, smiling. "What kind of a hairbrush was it? A big one?"

 

"Oh-forget it Pepper, this is ridiculous." Libby was blushing. Oh, God, she'll tell Ted and Dan and Kitty and Melvin...the whole gang will think I'm a pervert AND a dyke!

 

Pepper looked at  Libby steadily. She didn't smile. "Go get me the hairbrush that your mom used. Or should I ask her where it is?"

Oh Jesus! Libby jumped up off the chair as if she'd been branded, and ran into Mom's room, picking up the vintage French ivory hairbrush.

 

Dad bought it for Mom when he was abroad in Africa during the war...they don't make hairbrushes out of elephant tusk anymore.

 

As Libby hurried back into the bedroom, old memories came back...Mama's rage when Libby spilled soup, going over the knee, panties ripped down.

Then the French Ivory hairbrush falling again and again...Little Libby crying in the corner, with her panties around her Reeboks!

 

Libby came into the bedroom, and tossed the hairbrush to Pepper, who caught it neatly and began examining it.

 

Libby rolled her eyes. "Look Pepper, forget all this. I was just goofing on ya, you know? Let's go to The Newport Creamery."

 

Pepper smiled to herself as she toyed with the large oval hairbrush. Goofing on me? Twenty diary pages? I think not.

 

 

 Pepper looked up at Libby, and smiled broadly. "I don't feel like going out right now, Libby. Maybe later we can go to the mall...but right now, I think I'll spank you."

 

Libby's mouth dropped in horror. She'd thought perhaps if she told Pepper about these insane fantasies that she'd been having...Pepper would make fun of her, and they'd drop the whole thing!

 

Pepper tucked in her tank top, emphasizing the huge breasts, and tapped the ivory hairbrush into her palm. "C'mon Libby...take your medicine."

 

Libby's legs quivered, and she felt a faint moistness in her groin.

 

"Buh-but Pepper, I just..."

Pepper crooked her finger and looked adamant. Finally Libby unbuckled her weave belt and took down her shorts and panties, and bent over Pepper's knee.

 

"Boy, Libby, you really are a sickie." Pepper said as she raised the hairbrush over the globes of Libby's bare buttocks.

 

"Why do you say that, Pepper? It's just a joke, right?"

 

Pepper laughed evilly. "I never told you that you had to take down your pants, you stupid slut--that was your idea!"

 

As Libby writhed in surprise, the hairbrush came down with a bang!

CHAPTER TWO

Climbing off Pepper's lap, Libby bit her lip and a tiny tear streaked down her face. She looked at Pepper and hiccupped, and looked at her feet.

 

Libby's wet eyes closed as she re-felt the vicious slaps of the hairbrush, again and again all over her cheeks and thighs!

 

But maybe Pepper felt bad for putting Libby through such pain. Was she feeling guilty?

 

Libby looked up hesitantly.

 

Pepper was laughing at her! "Baby, baby, suck your thumb!"

 

Silently Libby reached down to pull up her panties and faded jeans. Halfway up her long legs, Pepper put a small hand on the rising buckle.

 

"No, no...Did I say you could pull up your pants now?"

 

Libby bit her lip, half anguished, half annoyed. Pepper had given Libby twelve spankings over the past two weeks...this was getting out of hand!

 

The first one had been a light paddling and ended with a hug and Pepper taking Libby out for an ice cream at the Creamery...

 

But when Libby had shyly (and foolishly) asked Pepper to spank her again, Pepper had used her tennis skills! And what a backhand!

 

My God it had been practically a drubbing every day, and sometimes in the most improbable places--for Pepper had taken Mom's French ivory brush home with her--thank God Mom didn't ask about it!

 

Five times at   Libby's house, four at Pepper's, once at Ted's when he was in the back yard looking for a football (and boy had Libby yanked up her jeans JUST before Ted sauntered back in).

Then one horrible time in the changing room at  Macy's...Libby had criticized one of Pepper's purchases, a top that made her look fat...honesty was a bad idea right now!

 

And now... KNOCK! KNOCK! Melvin’s nasal tone.

 

"What are you guys DOING in there? We're gonna be late for Trigonometry!"

 

How could Pepper punish Libby in the Girl's Restroom at school? Anyone could walk in, you know...

 

Libby wanted to pull up her pants and panties but Pepper's finger was still on the crotch and the damn things were at knee level! Pepper was sitting on the toilet, fully dressed of course, and Libby was just outside the stall, biting her lip.

 

"P-please let me pull up my pants, Pepper, someone's coming in!" Libby protested weakly. "Jesus. C'mon!"

 

Pepper smiled. "All right, but I want you to come to my house after school today and winterize my clothes...summer's coming."

 

Libby sighed and rolled her eyes. "That's a big job..."

 

Pepper chuckled. "Do you want Big Hilda DeTerisi to trot in here and tell everybody you're bare-assed?"

 

Libby shook her head shamefacedly. "No, I'll-do it."

 

"I want you to clean all my tops and pants, dresses and skirts, put them in plastic bags with mothballs, but for God's sake don't hang my knit sweaters because they'll get out of shape--"

 

"O-okay Pepper!" Libby begged. "Can I pull up--"

 

Pepper shook her head. "Just a moment. Make sure the clothes are airtight in the bags, particularly my Donna Karan stuff. Yeah and take my winter jacket and blankets for dry cleaning."

 

Suddenly the door opened, and Libby hopped away from Pepper and yanked up her jeans, almost forgetting her panties in the process!

 

 

Pepper looked annoyed. "Did I give you permission?" But Libby was wiping her eyes and buttoning up her jeans as a troop of noisy sophomores came into the bathroom.

 

"Oh, and Libby" Pepper said as she and Libby went into the hall, to head for Trigonometry class.

 

"Yes Pepper?" Libby asked, trying to look positive, since her afternoon was now shot with Pepper's chores. "We're going to your house after--"

 

"No, here's my key, honey. I'm going to watch Ted and Melvin and Jug shoot hoops, and we're going to the Pizza Hut afterwards. I'll see you tomorrow. Make sure it's all done!"

 

Pepper spun on her heel, ignoring Libby's horrified look. That's right, you perverted cow, Pepper thought. Why should I waste an afternoon mothballing?

 

As she walked, Pepper remembered that she was supposed to be in Trigonometry...but, there might be a more productive way to spend the hour...

 

Pepper saw Mr. Marks, Westerly High assistant principal, coming down the hall, and she stopped and leaned against a wall.

 

Mr. Marks stopped in the middle of the hall also. Good God, he thought…there’s too much Portuguese-Italian trash in this school.” Miss Scarnarella, don't you have a class to attend?"

 

Reaching into her bag, the unconcerned Pepper pulled out a tube of  DiorKiss Luscious Lip-Plumping Gloss. "Ah, yes Berry Smoothie"  Pepper said softly, as she began "plumping" her lips.

 

"Did you hear me, Miss Scarnarella" demanded Mr. Marks. "I asked you if you had a class just now!"

 

Pepper looked up lazily, and unzipped her long leather coat, for as she'd observed to Libby, spring was here.

 

Pepper  unzipped further, casually exposing her neon pink lycra tie front halter crop top and matching open side mini skirt.

 

Beneath the skirt were Silicone Wide Lace Top Stockings, a sort that Mr. Marks recognized because Mistress Medusa had sent him some to beat off over in the mail last week.

 

"I--I'm sorry, Mr. Marks." Pepper said throatily. "I-I was hoping to talk with you for a moment."

 

Mr. Marks gazed somewhat abstractedly at Pepper's neon pink outfit and mumbled something about dress code.

 

Pepper looked up at Mr. Marks dreamily. "You-you don't like my halter?" She moved a little closer to the administrator.

 

"It-it is a little tight around the heart, do you know what I mean? I worry that the top is tied too tight, and I feel a pressure--"

 

Pepper reached out a red tipped finger and took Mr. Marks's hand in hers and put it close to her heart.

Nauseated inwardly at the clammy middle aged paw resting on her chest, Pepper said: "Do you think I have a medical condition?"

 

Mr. Marks's knees knocked together slightly. Although he dearly wanted to examine Pepper's condition further, he reluctantly pulled his hand back, and smiled.

 

Pepper smiled back, a finger on her chin. "I look up to you, sir...and I just didn't feel comfortable talking with the school nurse."

 

"No, no she's a quack" Mr. Marks said. "Well, Miss Scarnarella, if that's all, perhaps you'd better be going to class now."

 

Mr. Marks was hoping to make a bee-line to the Faculty Men's Restroom, where he planned to take the pressure off with a little pud-pounding.

 

But Pepper said innocently, "I thought maybe we could go into your office. I have this terrible grade on my Lit exam? I know I have a class right now, but possibly you could excuse me from it?"

 

It seemed to be in Mr. Marks's power to excuse her...

CHAPTER THREE

Mr. Marks carefully locked his office door after Pepper Scarnarella left, twitching her little pink miniskirted tush.

 

Mr. Marks stripped naked, his obese form jiggling as he searched in his drawer for his Special Kit.

 

"Ah yes!" Marks said happily, pulling out a three pronged piece of clothesline.

 

 On two of the ends there were clothespins, which Mr. Marks clipped on his nipples, and on the third was a snug cock ring-rope.

 

Now, the rope was tight, so that Marks's nipples were being dragged downwards by the Y ends, and the balls were pulled upwards.

 

This ring-rope, with some painful tugging over the vice principal's tumescence, was pulled round his cock and balls.

 

Mr. Marks then reached into his drawer again, grunting, and took ten metal jacks that he'd confiscated during his years as an elementary school teacher out of the desk, as well as some sandpaper from the Shop class, and lubricant.

 

He then laid the small metal six-pointed stars on the floor and then knelt on them, so that the pressure from the floor through the sharp jacks bit into his knees.

 

Mr. Marks sat up straight, and bit his lip as he felt the cruel tug of the nipple clamps. Dousing his penis with the lubricant, he wrapped the sandpaper in a grip around his penis, and began rubbing it up and down the shaft, called by one ex-wife "The Vienna Sausage".

 

As the sandpaper ripped back and forth along his tender penis,  his nipples and crotch both felt as if they were being torn apart...

Marks thought of Pepper Scarnarella, and he began fantasizing!

In fact, all that had happened was the little minx had sat in front of Marks's desk, with her gorgeous legs crossed.

 

Those hot little sheer stretch spandex thigh high stockings with wide opaque faux chain design tops...and the wet looking six inch fuchsia high heels!

 

They had had a conversation about a ridiculous grade that Ms. DeStefano had given the poor girl, and Marks had become so concerned that he'd come out from behind his desk, and pulled up a chair close to Pepper...

 

The girl had taken Marks's hand at one point, looking tearful, oh my! And breathing heavily in that obscene little top.

 

Before she'd left, Pepper had borrowed twenty dollars from Marks, because she said the school bus gave her sniffles.

 

But didn't the girl live three blocks away?

 

Marks began to fantasize, while rubbing the scratchy sandpaper across his penis...

In the fantasy, Marks was kneeling naked before Pepper, who laughed haughtily, and walked back and forth on the fuchsia high heels, while wielding a horsewhip...

 

CRACK! WHACK! SLASH! "Take it, you fat little piggie!" Pepper said, waving her cleavage in the sweating Marks's face.

 

"You're nothing but a worm who needs to be reminded what a worm he is!"

 

The physical, actual Marks ground his knees into the jacks and pumped his cock faster, grimacing at the pain  in his nipples.

 

 

The nipples were being pulled harder as Marks's scrotum filled with semen, and his knees were in sorry shape, now!

 

Mr. Marks sweated as his fantasy changed...now he was strung up by the balls from the ceiling in the gym while Pepper, clad in a blue lace stretch teddy, was  standing on a painter's ladder, playing with the cock and balls that supported Marks's swinging body.

 

Pepper's long nails were tickling and tugging at Marks's throbbing cock, but the stretching of the balls was almost too much.

 

Marks also fantasized that his nipples were being dragged down by large anvil weights, and he was gritting his teeth desperately, trying to keep from falling into the earth!

"Please, Miss Pepper" screamed the fantasy Marks. "Please let me down from here, before you completely stretch my scrotum!"

 

But now Pepper was on the gym floor, giving black student and frequent detention attendee Polonius Ponds a slurpy blowjob.

 

Polonius   looked up contemptuously. "What's wrong, you fat honky? Don't you know what a loser you are?"

 

Marks, in his physical form, kneeling on the jacks, now quivered and shot across the office. Suddenly, fantasy gone he was aware of the intense pain in his knees, and the shame he felt...

 

He got up quickly, pulling embedded jacks out of his knees, and cursing to himself...ah well!

Outside, school was letting out. As Mr. Marks dressed for home and Libby disconsolately headed off for a dreary afternoon of  mothballing, Pepper Scarnarella walked out into the Rhode Island sunlight with five attentive boys, whistling.