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Karen Babysits for a Man Her Age

Karen was surprised when her neighbor, Mrs. Kendall, saw her on her way home as she was walking up to the front door. She had known Mrs. Kendall slightly but enough to know that her very attractive neighbor was apparently divorced and also was a high-powered executive with a major consulting firm. Karen was in her mid-20s and still a junior staffer at the business magazine where she had worked as an ad executive for about three years.

As time went on, she had more and more respect for her neighbor, who had clearly succeeded in the highly competitive business world. Mrs. Kendall was always well-dressed and perfectly groomed. Karen was forced to admit that she had somehow become a true role model and yet she knew little about her.

Mrs. Kendall called to her in a low but definite tone to come over for a moment. When the surprised Karen complied with the request, without even thinking, Mrs. Kendall invited her to step in for a moment. Karen never thought of asking what the invitation was about.

"You seem like a smart young woman on her way to success," Mrs. Kendall began. "I know you are quite busy with your work, but I'd like to ask you a favor."

Karen smiled and responded that she'd be happy to hear what Mrs. Kendall had in mind.

"First, my dear," her neighbor began, "please call me Claire. You seem to have enough experience of the world not to be too taken aback at what I will discuss with you."

"You may have seen my nephew Jamie who has come to stay with me while he gets a job and puts his life together," she went on.

"Jamie is here in my house much of the time and I thought you might stop in when you get home from work and see that he is doing what I have assigned him to do," she said. "He is supposed to be making contacts to find work and also to clean and do some chores for me. I have a list and a little notebook in which I keep track of him. I'd like you to have these and to supervise him."

Karen was surprised but thought this might be worthwhile, both in terms of what Mrs. Kendall could do for her if she helped her out now and the possibility that she, Karen, might get a chance to take charge of this young man.

"How old is your nephew?" she asked.

"Oh, mid 20s," Claire answered. "You'll have an easy time taking charge of him," she added, as if she had read the younger woman's mind. "I'll tell you that I have already had to discipline him for laziness and other things and I will welcome your doing the same if he doesn't do what he is told."

"Really?" Karen responded, showing some surprise although she was trying to repress her excitement at what seemed like her neighbor's ability to read her mind.

"Yes," Claire added, "so if you think he is shirking or misbehaving, you can take his pants down and give him a good spanking as if he were younger."

"Might I ask for what he has been spanked?" Karen ventured, as if she were just realizing what was involved.

"Well," Claire said, "he sometimes leaves the bathroom in a mess, forgets to flush the toilet, and I'm sorry to say I've caught him looking up my skirt."

"Oh, how naughty!" Karen exclaimed. "I forget how boys can be, although by the time they get to be his age, I would've thought he'd learned to behave like an adult."

"I find I need to spank him regularly," Claire confirmed. "And you are welcome to use other methods if you feel they would be more effective. My friends have suggested, for example, that I make him wear panties and check them regularly for cleanliness, or give him disciplinary enemas."

Karen was hearing all her most repressed fantasies coming to life as Claire described what clearly was part of her personality.

"I think I can help you with this," Karen said confidently. "When do you want me to start?"

"No time like the present," the always-decisive Claire responded. "Come inside with me now and I'll introduce him to you."

They walked into the house and Karen marveled at how tastefully Claire had decorated the home. The furniture was contemporary and Karen could tell that it was expensive even though the rooms looked a bit stark in that ultra-modern manner.

The blonde young woman now was staring at a fairly good-looking young man seated on a recliner, with a television on in front of him.

"Jamie," Mrs. Kendall said firmly, "turn that off and meet my neighbor."

The young man stood up, smiled, did what he was told, and walked over to the two women who were standing at the other side of the room.

"Karen, or rather Miss Cranford," Claire said, "this is my nephew Jamie. Jamie, Miss Cranford, as you will call her, will be in charge here when she returns from her office each day and she will be supervising you until I get back. I will remind you that she will check to see that you have done you chores and persevered in seeking a decent job. I have also told her she has my total authority to discipline you if she finds you shirking in any way or showing her any disrespect."

Jamie's handsome face reddened. "I'm sure she'll not find any problem here," he said softly.

"Well, I'm not so sure of that," his aunt answered sharply. "It's high time you found work and I don't want you causing Miss Cranford any bother."

Then she reached into a cabinet and brought out a small cane and a Scottish two-fingered tawse.

As Jamie blanched in shame, his aunt went on, "If he acts up or does anything to displease you, Karen, don't hesitate to use either of these. He already has felt them both on his bare bottom."

"Jamie," she asked, "to whom did you speak today about work?"

"Well, Aunt Carolyn, I got caught up in going through the announcements so I didn't make any calls," he admitted sheepishly.

"You see what I mean, Karen?" Claire inquired with a note of dismay.

"I do indeed," Karen replied firmly. "It seems you have a difficult situation here."

"Normally, I would discipline him for this," Claire stated. "But if you're willing I'd like you to take him across your lap for a good bottom-warming."

Karen was surprised but thrilled and felt herself getting wet in her panties at the prospect of baring and disciplining this young man who was just a tad younger than she was.

"James," she pronounced, using his full name, "I'm going to sit on this chair and you will drop your pants and your undershorts and get across my lap."

Jamie was taken aback at how quickly he would be shamed by his aunt and this lovely young lady he would wish to date. But he complied and Karen saw his hairy crotch revealed along with a flaccid but clearly large penis.

Karen sat down on the armless chair, adjusted her skirt so it was straight and disclosed nothing to what she saw were Jamie's roving eyes, and beckoned him across her grey-skirted lap with her index finger. She had him right in position with his bare bottom cheeks staring up at her and his head down almost to the carpet.

Then Claire handed her the two-fingered tawse. She put it down on the end table next to her and began spanking the young man efficiently with an increasing tempo and intensity.

Watching as his cheeks began to redden and he began to whimper, she then picked up the tawse and started to apply it to the cheeks, occasionally letting the tails just barely slip between his anal crack.

When Jamie felt the tawse slip between his legs and snap lightly over his scrotum, he let out a slightly repressed cry. Karen didn't want to injure him so she now concentrated on his attractive slim bottom. Soon it had turned a nice shade of red. She let him get up and pull up his shorts and trousers.

Claire smiled and said, "Karen, I think I've found just the right person to supervise Jamie. Jamie, now thank Miss Cranford for disciplining you."

Jamie realized he had better show his compliance so he smiled and looked right at Karen. "Thank you, Miss Cranford, for disciplining me. I'll try not to make you go to the trouble again."

"That's fine, Jamie," Karen replied. "I only will need to punish you if you misbehave again."

Claire was smiling from ear to ear. "I'm going out now," she announced. "Karen, I hope you can stay for a while and get acquainted with my nephew now that you've disciplined him so well."

Karen smiled back and assured her that it was no trouble at all. Claire had told her how much she would be paid and that too was an inducement. But even more was the chance to show the obviously successful businesswoman how competent she could be.

Claire visited the bathroom to adjust her makeup and to empty her bladder. Karen was surprised that she could hear everything in the little powder room. She wondered why Claire had no blower but didn't think more about it.

When Claire had gone, Jamie put on his charm and told her he was sorry she had had to meet him under the circumstances. She merely said she hoped she would be of help to him.

He chuckled and asked, "Did my aunt warn you about my looking up your skirt?"

Karen's face reddened and she told him she thought he was being inappropriate.

Jamie decided to chance it and said his aunt didn't like him doing that.

"Well, no woman does," Karen said, a bit snappishly.

"You don't have to get your panties in a snit about it," Jamie rejoined.

"You're being inappropriate, young man," Karen answered, picking up some courage. "I don't want to have to spank you again so soon but I will if you don't stop that."

Jamie laughed and said, "You know I saw your panties when I was across your lap, Miss Karen."

"That's quite enough of that, young man," Karen said firmly. "Stand up and take down your trousers and undershorts. This time you're going to see what getting spanked is really like."

"Hey, I was just kidding," Jamie tried to defuse the situation. "Really, are you that sensitive?"

"I'm not here for you to joke about," Karen crisply declared. "If you don't do what I said right now, your spanking will be doubled."

Now, Jamie was frightened. This young woman was as tough as his aunt, maybe more so.

He did what she said and crawled once again over her lap with his reddened bottom staring up at her.

"I see that I'm going to be seeing a lot of this naughty bottom," Karen pronounced. She proceeded to remove his pants and shorts entirely and place them next to the chair.

"Hey, what's that about?" Jamie asked whiningly from his vulnerable posture across her lap.

"You'll see...after your spanking," Karen said sharply. Then she began spanking again, reaching after a few minutes into her handbag where she found her small wooden hairbrush and began to apply it to Jamie's backside.

"That's hurts!" he exclaimed.

"Yes, it's supposed to," she answered and kept striking him with the brush.

She then decided to up the ante and play on his clear fascination with her.

She told him to stand and face the wall. She told him he was going to spend some time in the corner and now he was afraid of her so he went right to the corner and put his nose into it.

Karen then reached under her suit skirt and slipped off her blue hicut panties.

After Jamie had spent ten minutes in the corner, she called him over and told him he would be wearing her panties.

"Since you were so interested in them," she said, handing the small blue garment to him, "put them on, right now!"

Jamie hurriedly stepped into the panties and ashamedly tugged them up and barely managed to make his hard-on fit inside them. They felt warm and he realized Karen had been wearing them all day. Maybe he would be able to keep them if he behaved.

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