Bad boy gets caught

I'll call him "Robert." Robert likes to fantasize that he is a young teenage boy with a crush on his next-door neighbor, Mrs. W. When Robert and I play, I become Mrs. W. Some of his misdeeds include going through Mrs. W.'s lingerie drawer while he's house sitting for her, and actually trying on her panties, and then her bathing suit, and jerking off thinking about her.

Because Robert is careless and doesn't cover up his crime very well, she discovers what he's done. She also catches him watching her in her pool, from his second floor bedroom window -- one hand on binoculars, the other hand out of sight, down his pants, most likely.

Mrs. W. gets out of the pool, wearing her new one-piece bathing suit that she'd purchased to replace the other one she'd found soiled and, in her eyes, ruined. Looking up at the second floor window, she crooks her finger and beckons him to come down to the pool area. Startled by his discovery, Robert jumps back from the window. She smiles to herself, wondering if he has the nerve to come do as he's told -- or if she'll have to punish him at a later time. One way or another, sooner or later, he WILL be punished.

But he is obedient and soon her pool gate opens and he enters her yard, sheepishly, hardly daring to look at her. "Let's go inside into the air conditioning, Robert," she says. "I have things I need to discuss with you that I wouldn't want our other neighbors to hear -- and I don't think you'd want your mother to hear, either -- would you?" He blushes, puts his head down,mutters "No, Mrs. W."

"Let's go, young man."

Inside her house, she begins to lecture him sternly, chastising him, telling him his behavior has been despicable and he needs to be taught a good lesson. She says he needs a good, hard, bare-bottomed spanking. He jumps at the words. "No, Mrs. W. I promise, I won't do it again," he protests.

"Would you rather I tell your mother? And recommend that SHE paddle you?"

He whispers, embarrassed, "No, Mrs. W."

"Then let's get this unpleasantness over with, shall we?" She wastes no time pulling out a low stool from the wall. Grabbing his wrist, she yanks him over toward it. She stands him in front of her and unbuttons his pants, lowers them. "Step out," she commands. Next, his drawers are lowered to his knees. "Oh, god," he whispers. She responds: "It's time, Robert. Get over my knee, now!"

And the spanking begins. She uses her hand, hard, as hard as she can, for several minutes. Robert is kicking and yelping, crying out that he's sorry and he won't do it again. "I know you won't, dear," she says, "but you're being punished, and we've barely started." Mrs. W. makes him get up for a few minutes and stand in the corner, while she lectures him about her clothing that he ruined. She shows him the old bathing suit, which she says he will have to pay for out of his paper route money, OR pay over over time with a weekly spanking all summer long.

She then grabs his ear and pulls him yelping from the corner, back to the stool where she throws him back over her knee. She spanks him with a large wooden hairbrush now, which makes him sob and kick even harder. She does not stop spanking until she has given him one hundred strokes with the hairbrush. His bottom has turned very red.

Standing Robert in front of her again, Mrs. W. says that he is a child, out of control. She says in order for him to learn better self-control, she's going to embarrass him by making him wear plastic pants like a baby would, like a toddler would. "No, Mrs. W. Please..." She picks up the hairbrush again and whacks his behind with it a few times, very hard. "Okay! Okay!" he yells. He puts on the plastic pants, and finds himself right back over her lap, staring at the floor again. She continues the hairbrush spanking, covering every inch of his bottom.

"I still don't think you've learned your lesson," she says, pausing the spanking. When the next stroke lands, he yells, "Yes, I have! Ow! I have!"

"I'm not satisfied," she says. "Stand up and face the corner again. I think I'm going to have to make SURE you remember this." She picks up a bottle of baby oil, pours some onto her hands, then goes over and rubs the oil all over his bottom so that it is shiny and red from the spanking he's already gotten. She can feel him shivering, a bundle of nerves. She knows he wants to be good -- but he's got to try harder.

Mrs. W. tugs Robert's arm, pulls him out of the corner, and back to the stool. laying him across her knee once more, she rubs in a tiny bit more baby oil to make sure everything is covered. And then she lifts her arm and resumes the spanking, this time MUCH more painful.

"You're getting spanked just like the little child you've been acting like," she says. "Just like a little boy who hasn't learned to control himself." She picks up the hairbrush again, tightens her grip on his waist, and says, "Well, now you're going to learn. I hope you can't sit comfortably for a week!" And she begins to paddle his bare bottom, not letting him loose no matter how much he kicks his legs, sobs, and promises he'll be good. The brush strokes just keep coming and he has no choice but to take them...