Buddy's cock was in such pain. The Fun Pouch was everything the Little Shop in New Hampshire had advertised it to be!
A leather pouch just big enough to cover the penis and testicles, but a bit too snug...and filled with needles!
When Pepper had casually suggested it, Buddy had become quite excited, and had special ordered it from the Little Shop catalogue!
But of course, the idea of torture, and actual torture were two different things... Earlier that day, Pepper had come in between shifts and rubbed her long nails against the little leather Fun Pouch, leaning over and kissing Buddy on the ear.
"Do you like my perfume, baby?" Pepper had said softly into Buddy's ear. "It's Amirage D'Amour...you bought it for me last Christmas..."
Buddy's cock had instantly lengthened, and felt the thousand stabs of the evil pins in the Fun Pouch!
Pepper had snorted with laughter as her tearful boss had dropped to his knees in acute pain!
Buddy was trying to focus on a liquor purchasing order, but it was nearly impossible, as he kept looking at that evil bitch through the door of his office!
Buddy sweated bullets as he stared at Pepper's breasts beneath the snug backless rhinestone v-neck cleavage expanding purple crop top she wore today.
Her boobs looked like encased cantaloupes, for God's sake!
And then, instead of the regulation Bermuda Shorts for all Naragansett Cafe employees, Pepper wore a micro mini pleated denim thing that didn't get past her upper thighs.
And these gartered stockings that SHOWED the garter to everyone in the Naragansett Café!
Completely against the uniform rules for everyone else, but Pepper didn't care.
The other waitresses hated her--and who could blame them?
Pepper was lazy, she couldn't be bothered to clean her table when they had no busboys, she stole other waitresses tips, and she smoked as she worked!
Parading about lazily with a menu in hand, a Lucky Strike sticking out of her painted mouth...and what a sneer!
In a no smoking restaurant, if you could imagine. "Why don't you fire her, Mr. Cistulli?"
Every waitress had asked Buddy that in the last eighteen months, and several good ones had quit over Pepper's appalling behavior.
As Buddy looked on in horror, Pepper stumbled over one of her high heels and spilled some hot soup on a woman, and the customer screamed.
But, the woman's boyfriend ignored his scalded date, jumping up and taking Pepper's arm. "Are you all right?"
Buddy had to laugh at that. Pepper sure had men hypnotized!
But, as Pepper bent over in feigned concern for the poor woman, Buddy got a nice look at her cleavage again, and his penis inflated---and the needles skewered!
Buddy gritted his teeth, and tears streaked from his eyes. How he wished he could get the fucking Fun Pouch off his crotch...but it was padlocked.
And you-know-who had the key! Pepper looked up at him, as if she knew he was thinking of her, and winked!
For a moment, Buddy noted a piece of register tape that the owner had waved in his face the other day...and sweated.
"There seems to be some kinda discrepancy, what's going on, Buddy?" The craggy, trusting old man had asked.
But the fact was, Buddy had been spending a wee bit too much money on his favorite waitress. They'd just started out with light spankings and teasing and denial games...
As Pepper had a roommate deal at home, and Buddy still lived with his parents, she'd encouraged him to find them a nice motel room.
Tying Buddy up and teasing his cock until it nearly burst with her long fingernails was lots of fun.
Although she occasionally rode his face to an orgasm or two, he'd wondered what she got out of helping him with his particular kink.
After Pepper had put the Fun Pouch on Buddy nearly a year ago, things had radically changed! The evil little padlock had made things quite mandatory for poor Buddy! The first week of Buddy's chastity had been painful but exciting...Pepper had removed the pouch twice for teasing, after which she'd let Buddy fuck her, and the sex had been wild!
But then the next time, Pepper had been in a bitchy mood! Buddy had done all the nice stuff, rented a great hotel room (Pepper felt motels were getting low-class) brought her candles in the bath, and given her a hot oil massage...
Touching those beautiful naked breasts had driven his cock crazy, and Pepper had smiled grimly as Buddy had kept moaning, as he rubbed the contours of her body.
Buddy had gotten between Pepper's legs and licked her to a mind blowing orgasm, and then another!
Then, when it got late, Pepper had said, "Well, I gotta go home to my roommate Libby now!" Buddy had looked like a whipped dog.
"B-but aren't we going to take off the Fun Pouch and--" Buddy protested, and Pepper had smirked.
"Buddy, why does it always have to be about you? Can't you just enjoy this time for me?" Pepper had casually kicked Buddy in his Fun Pouch, embedding the needles in his cock.
"That'll take your mind off pussy, right babe?"
It was true. It had been eight days since his orgasm, but he'd forgotten immediately in the intense pain...
It was a week before they got together again for hotel time. And what a week!
Every time Buddy saw his younger sister in her shortie pajamas, or checked out the Salve Regina coeds twitching their little butts...or the hot little secretaries in downtown Providence when Buddy went to the shrink to find out why he was such a pervert!
The next time at the hotel, Buddy had been even more pampering of Pepper, and of course the more he played with her body, the more painful it was for his penis in the Fun Pouch.
Finally, Pepper had bound Buddy's hands and removed the Fun Pouch, and began rubbing and stroking Buddy's penis and balls, remarking on how red and chafed they were.
"You must've had a horny week, eh, Buddy?" Pepper had even rubbed her full, soft boobs on Buddy's penis until he'd moaned.
But, just as Buddy was about to spurt, Pepper had removed her manicured little paw. "I have a financial problem, hon..."
A two hundred dollar loan. Plus the cost of the hotel and dinner, it had been nearly three hundred and fifty bucks for Buddy to get his rocks off!
And of course she'd locked the Fun Pouch back on...
Then Pepper had gone "out of town" and Buddy hadn't seen her for two weeks...the other waitresses, happy that the Brunette Bitch was gone, found their manager rather grumpy and anxious.
When Pepper had come back, she'd taken Buddy to the hotel again. He'd begged her to let him "stick it in" after he'd gone down on her and given her the requisite four hour massage...but again she'd beat his meat until the breaking point...
"I have a um, dental bill, babe...I need five hundred bucks!"
In the past eleven months, Buddy had given Pepper seven thousand dollars...none of it his.
Next week, the owners were bringing in an investigator to find out where their money had gone...and Mom was soon to discover that her charm bracelet made of authentic gold coins was missing.
Buddy was headed for jail, and it was bad news...
But Pepper was such a hottie, damn it!
Chapter Two Libby came into the dorm room, checking her watch. Shit. Pepper told her to be in twenty minutes ago.
Libby's knees knocked as she thought of Pepper's rage, how the rattan cane could slash bruises so fierce on Libby's thighs that she would not be able to wear a swimsuit 'til August!
But Libby had gotten caught up with a teaching assistant helping her in Biology Lab...It was so hard to explain this kind of thing to Pepper!
"I give a fuck what your idea of time is, honey." Pepper would say, blowing a bubble before ordering Libby to take her panties down and bend over the formica counter.
Libby looked around nervously as she entered the apartment. Pepper didn't appear to be home—she was probably off waitressing.
Libby had insisted to Pepper that she didn't HAVE to work, Daddy was paying the rent for both girls, and shit, if Libby asked, Dad would probably have paid Pepper's tuition to Salve Regina college as well.
"We Portugese don't need a bunch of sheepskin to make ourselves feel good" Pepper had said cheerfully. "Self-justification comes from hard work, babe...not endless school."
Now, Libby took her cell phone and photographed herself next to the clock, sending it to Pepper's phone. Twenty minutes late was bad, but it would have been worse if Pepper didn't know how late her roommate was, and assumed she was HOURS late.
Libby recalled the last time, when the car had blown a fuse, and she'd gotten in too late to fix Pepper's dinner...Pepper had laid Libby on the floor, bound at the hands and feet, and taken turns grinding Libby's tender nipples into the hard floor!
Best friends since childhood, Pepper and Libby's relationship had changed in senior year when quiet, athletic Libby had admitted to the brunette, gum-popping Pepper that she fantasized about Pepper spanking her...and other things!
Pepper had insisted on fulfilling Libby's fantasy, to the point that Libby was sobbing in the corner of her bedroom at the end of every visit of her old friend!
