Whipping Boy, Part 2

Here is the conclusion of our story. Rory is drawn to Barbara like a moth to a flame and passions flare.


As Rory would later reflect, that little session did provide motivation—for a time anyway. He didn’t see Barbara for a while after that. Their schedules seemed to be out of sync. In frustration he found himself looking at her house constantly, checking to see if she was home. Anything, even just a glimpse. He told himself it was time. Time to declare himself. He was hers—in her hands to do as she thought fitting. She could command him. He’d do anything. Be her whipping boy if that amused her. He strongly suspected it did. His dreams at night had been fitful ones in which he saw himself on his knees before her, worshiping her while in her hand she held a paddle to discipline him if he disappointed.


He was by chance at an upstairs window when he saw her walk out into her back yard. The sun was bright, and it was hot. Summer beckoned and soon school would be out. Hopefully he’d see more of her then, but now she was a sight to behold as she carried a towel and a bottle of lotion with the obvious intention of using them to sunbathe. Rory’s eyes were glued to the scene as he watched her spread the towel out and rub lotion on her skin. Wearing a skimpy black bikini, she was a vision. What luck! The back yard was fenced and a row of tall shrubs provided almost complete privacy from eyes at ground level. But he had just happened to be in this upstairs room. Rory drank it all in, the high set breasts, the long shapely legs, the firm heart-shaped buttocks. He had to see better. In a flash he remembered he had binoculars. He raced downstairs to get them. When he returned she was still there.

The window was open. Rory slunk down below the sill and rested the binoculars on the ledge. He kept his profile low so she wouldn’t see him if she turned his way. She had opened the lotion bottle and was standing there, spreading it all over, rubbing her thighs and the backs of her legs. He could see it all now quite clearly. The binoculars made it look as though she were ten feet away. He could see every line, every curve of her body. His right hand stole down to the waistband of his shorts and slipped under the elastic. Finding his erection he began to stroke it. And lost his grip on the binoculars. They fell from the sill, clanged onto the top of a garbage can lid below, and bounced, landing in a plot intended for a garden in Barbara’s yard.

She froze at the sound of the clang. Her eyes turned in the direction it had come from. Then she looked up, only to see Rory half out of the window. He had lunged to try and catch the binoculars. She stared straight at him then followed his eyes to the garden plot. She walked over and found the binoculars lying in the dirt. Rory stood there, outlined in the window. He blushed, embarrassed and chagrined.

“Rory!” she said. “You have some explaining to do, young man.” She shook the offending eyepieces at him. “I can’t believe this. You get down here this instant. I’ll be waiting inside for you.” And she stormed off into her house.



He’d given her the perfect opportunity. She knew what she wanted to do with this boy. She’d created the perfect lure and he’d fallen right in. Come into my parlor, said the spider to the fly.

Yes, he’d be a very good boy indeed, especially after a little discipline. And she’d be in total control. It was a heady feeling.


Now he’d done it. That was so rude. What could he do? Beg for mercy, obviously. It was the only possibility.

With a heavy heart he went next door and rang the bell. A voice inside said, “Come in.”

There was Barbara. Now she had on a short linen robe. It revealed the long sensuous lines of her legs. She stood in the foyer. Her arms were folded and she glared angrily at him as he tried to make his apology.

“Barbara, I’m sorry…I just…” He started to stammer. She cut him off.

“I believe these are yours.” She proffered the binoculars.

“I…I don’t know what came over me. I saw you come out and I wanted, I wanted…” He couldn’t say it.

“You wanted to spy on me, is that it? It is, isn’t it?”

Rory couldn’t find words.

“Rory, I’m so disappointed in you. This is what I might expect from a fourteen year old adolescent. Peeping. A naughty little middle-schooler. Like that eighth grader you were long ago, perhaps? Were your hands down in your pants, too?”

Rory blushed beet red.

“I thought so. Uh huh. I thought so.” She tipped her head back and nodded to herself. “So what should I do with you Rory? What should I do with such a naughty young man?”

The way she said it gave Rory a chill. What did she mean? She looked sort of angry, but underneath there was this hint of suggestiveness creating an electric charge in the air. It felt like she was playing with him, like a cat plays with a mouse.

She answered her own question. “I think I should punish you properly, Rory. Give you what a naughty boy like you needs. What do you think, Rory?”

“You…you could punish me. Like before. Or any way you wanted.” It was all Rory could think of. Losing her friendship was unthinkable.

“I should teach you a lesson, Rory. Ladies do not like to be spied on, or ogled. Especially by boys who have their hands in their pants.” She glowered at him and said, “Go get the paddle.”

The paddle. It’s what he’d been afraid of and what he’d craved. Even so, Rory hastened to do her bidding. Was he going to really get it this time? Maybe it wouldn’t be so hard. The last time had been bearable, delicious fun, almost. Well, later anyway. Still he felt his penis thickening. He’d already been hard from watching and his erection was tenting out the front of his shorts. He took the paddle off the door and returned. She crooked her finger and turned to walk down the hall.

“Come with me,” she said.

He followed. They were going to her bedroom. His eyes followed her twitching hips down the hallway. Once inside a very feminine bedroom she sat on a padded chest at the foot of the bed. The robe came open. Rory’s eyes fixed on her breasts. She saw where his gaze was directed and frowned.

“That’s what I’m talking about. You need to learn some manners, young man, if we are to continue to be friends.”

“Yes, ma’am,” said Rory.

She took the paddle and put it on the bed. Put her hands on her hips. “Stand in front of me, Rory.” He obeyed.


“What you did was rude and childish. I’ve been thinking about an appropriate punishment for you.”

Rory held his breath.

“We can still be fiends, Rory, but you have to accept my punishment on my terms.”

“Yes, Barbara, anything.”

“You will call me Miss Tisdale or ma’am until we are done. Is that clear?”

“Yes, ma’am.” She sounded like the Miss Tisdale of old, the stern teacher with the paddle and the will to use it. Then came the words that nearly made his knees buckle.

“Rory, you are going over my knee for a very sound spanking on your bare bottom. That is what I would prescribe for a boy of fourteen, and that’s the way you’ve acted. Now,” she said, pointing with her finger, “take down your pants.”

His bare bottom? Over her knee like a kid? He blushed with shame, but his cock surged. He hesitated.

“Did you hear me, Rory? I said take down your pants.”

Gingerly Rory slipped his thumbs in the waistband of his pants and peeled them down, dragging his underpants with them. As he did, his erection popped up, a long thick cock bobbing up and down right in Miss Tisdale’s face. She blinked, startled at the size and strength of the male organ that confronted her. Rory thought he saw a faint blush.

Then she pursed her lips, recovering from the shock. “Well, Rory, I can see what’s been on your mind.”auntie

Rory’s blush intensified. He felt like his face must be bright red. Worse, he had noticed her robe. It had slipped open, revealing her bare thighs and the triangle of that black bikini.

“Over my knee, Rory. Right now.” She pointed a finger at her lap.

Rory eased himself face down across her thighs. He gasped as his cock came into contact with the flesh of her legs and he slid himself over. The tanning lotion had made her skin slippery and the friction sent a delicious surge of pleasure up his spine. Then she opened her legs slightly and his penis slid down between them. Once he was all the way over, nose nearly touching the floor, she closed her legs, clamping his penis between them. He moved a little. An experimental wiggle. He nearly erupted.



Barbara rested her hand on his bottom, squeezing, patting, testing the resilience of the globes she was about to chastise. Rory felt her hand and he shifted, tensing, waiting for that first smack.

“Now, Rory,” she said. “Let’s see if I can’t instill some better manners in you.”

Her hand smacked his bottom, the sound startling him with its sharpness. Another smack, different spot. Then another and another. It tingled. A not entirely unpleasant feeling. She got into a pattern, delivering brisk spanks to alternate cheeks, then occasionally, right across the center crease of his bottom. The spanks got harder, as if she had found the right leverage or angle of descent. Now it started to sting. She had some internal clock, like a metronome, timing the relentless repetitive spanks she applied to his bare bottom. The sting was like a slow burn, a fire gradually building. Rory found himself reacting, swinging his feet up behind him, clenching his buttocks, squirming. His behind was getting really hot. Still the steady smack—smack—smack  of her palm beat a steady tattoo made him gasp in air between clenched teeth. This was really starting to sting!


Barbara was wet. The boy’s cock had popped out at her and she’d had to stifle the impulse to just grab it and lead him to the bed. But dishing out a sound spanking, that was reward all by itself. The boy’s buttocks were pure poetry, little apples that quivered under her hand. She could feel his cock, all hard still, clamped between her thighs. His little boy behind just got redder and redder. It was a heady feeling, being in such control. He’d do anything she commanded. She was sure of that now. Her own personal boy-toy to cuddle or to spank! Just like this, she thought as she launched a rapid fire barrage that made him yelp.


“Ow! Ow! Ok, ok! Miss Tisdale, I’m sorry!” Rory squealed, bucking and writhing over the older woman’s lap. “I won’t spy any more! Please!”

“Stop squirming, Rory,” she chided, all the while continuing the spank briskly. “You’re only getting what every naughty boy needs, a hot stinging fanny.”

It was smarting ferociously now, wave after wave of unrelenting sting. At the same time the friction between his penis and her legs was driving him crazy with lust. As he pumped up and down to avoid her punishing hand, it was like sliding into a slippery sheath. Unconsciously, he had fallen into a rhythm, raising his hips in sync with her descending palm. He could feel a climax building. The only thing that tempered it was the burning hot sensation visited on his seat by Barbara’s sturdy palm.



She sensed Rory’s impending climax. Oh, no you don’t, she thought. I want to save that for later. She stopped spanking Rory’s buttocks and pushed him unceremoniously off her knees. How to calm that rampant penis down, she wondered. Her eyes fell on the paddle.


Rory saw her reach for the paddle and he put his hands behind him rubbing and shifting from foot to foot. His cock bobbed up and down. The combined effect was almost comical. Then he heard the dread command, “Over the end of the bed, Rory. You’re getting six with the paddle.”

He started to plead with her, then shut up. Something was happening here. She was breathing heavily, her eyes alive with excitement and lust. He was aware that she must have sensed his near climax and had called a halt. Her robe swung open freely now. She made no attempt to close it. Rory’s eyes widened as she flung it away. In the tiny bikini she was magnificent. He faced the bed and bent over, his hands on the coverlet. He felt her hand on his back, placed there to steady him no doubt. The paddle tapped him once, twice then—

Smack! Crack! Whap! Three rapid spanks.

“Ahh…ow…Arhhh!” Rory yelped, rising on tip toe.

“Hold still, Rory. Take your licks, young man.”

The last three were spaced apart. Each one felt like an event. Each one was a searing blast of heat. Rory’s finger clutched the bedclothes so tight his knuckles were white. His knees sagged after the last one. Whew! That had been something. His behind was a roaring bonfire. It throbbed in waves.


Barbara stood back, contemplating her handiwork. Rory’s bottom cheeks looked like a pair of tomato red beacons, almost shiny, set off against the pale flesh of his legs and back. His once rock hard erection now drooped, but Barbara had decided she’d fix that. “On the bed, Rory,” she said.

“What?” Rory stood and turned, his hands now gently massaging his burning seat.

She pointed with the paddle. “On the bed. On your back.”

Rory didn’t know what she had in mind but he was in no condition to argue. He scrambled onto the bed. Barbara stood beside the bed. She flung the paddle down and reached behind her. Rory’s eyes grew wide as her breasts sprang free. “Touch yourself now, Rory. Make yourself ready for me,” she said, as she tweaked her own nipples making them hard.

Rory’s hand dropped to his groin and he stroked his penis. It took only seconds for his erection to return and soon his cock was standing straight up. He watched, amazed, while Barbara tugged the brief bikini bottoms down, revealing the luscious triangle and its mass of dark curly hair. She placed one knee on the bed and lifted the other across Rory’s torso, straddling him. She hung there for a moment poised right above Rory’s upright cock. The she took her hand and seized it, placing the swollen head at the entrance to her vagina. Slowly she lowered her body, impaling herself on Rory’s stiff shaft.

The sensation was exquisite. He felt his member entering the slippery sheath and it took his breath away. Slowly, almost agonizingly so, she lowered herself until his shaft was embedded in her to the hilt.

“Don’t move until I say,” she whispered.

Rory nodded. He was close to losing it and he wanted this intense pleasure to last forever.

Then Barbara began to move. Short strokes at first, then longer ones as she rose and slammed down bucking on Rory’s groin as if riding a horse. Soon she was coming almost all the way up the length of Rory’s shaft before dropping back down to impale herself to the hilt. She mixed it up, sometimes rotating her hips as she leaned forward, hovering over him. “Lick my nipples, Rory. Go on, lick them.” Rory obeyed, reaching up with his hands, squeezing her breasts, putting the nipples together so that his tongue could flit from one to the other. She moaned and bolted upright. Barbara threw her head back and pounded her body up and down, feeling an eruption coming. When it hit she thrashed in uncontrollable spasms, moaning and flinging her head back. Rory’s climax came nearly simultaneously. The friction from the sliding sheath of her vagina overcame his desire to make it last and he too erupted in a frenzied dance, bucking and thrusting against her pelvis.

Barbara renewed Rory several times after that and taught him how to use his tongue to pleasure her as well. He especially liked it when Barbara had wanted it from behind and he got to appreciate the rippling of her lovely buttocks as his smacked her quivering bottom, his shaft thrusting deep inside her.


Friday night was whipping boy night. Rory found the summons in his mailbox. Once unleashed, Miss Tisdale had become insatiable. And now every Friday night a new instruction awaited him. He gulped as he read it. He was come in the door at 7pm. It would be unlocked. He was to strip completely and stand in the corner, hands on his head. The day before, as instructed, he had written down every lapse, every fault for the entire week. She, Miss Tisdale, would decide on an appropriate punishment. Sometimes it was a mild spanking with her hand. Other times she’d get out the paddle. But always they ended up in her bed. Lately she’d talked about more exotic instruments like a cane. She said English schoolboys got the cane and she’d always wanted to try one out. He gazed at her house, silent and dark, wondering what was in store tonight. But he’d be there, oh, yes he’d always be there, waiting, naked and shivering with both fear and lust.



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