Young Boss, Unwilling Celebrity Pt. 23

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Tim enjoys spanking Mary, unaware of what he's in for.
2.6k words
4.43
6.5k
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Part 12 of the 28 part series

Updated 04/18/2024
Created 09/28/2022
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Barefan
Barefan
271 Followers

Tim looked into Mary's eyes as she stood in front of him. She was blushing, and her worried expression just made her look more attractive.

Tim gave her a small nod, and her hands moved to the button on her shorts. Tim dropped his eyes to take her all in. She was wearing tennis shoes and tiny white socks. Her legs were slender and tan, and when his eyes had moved up to her snug shorts, he saw that her fingers were trembling slightly as she fumbled for a moment with the button before it snapped open.

She paused for just a second, then pulled down the zipper and tugged the shorts open. She had just started to wriggle when Tim held up a finger and softly said, "Turn around for this part."

Mary swallowed at that, but then complied. When she'd turned so that her butt was facing Tim, she pushed her shorts down over her ripe, round ass, and then gave a wiggle that caused them to drop to the floor. She could feel Tim's eyes on her rump, and she was both embarrassed and turned on.

"Very nice," Tim said from behind her. "You can face me again."

When she turned, she saw a small smile on Tim's handsome face, as he delayed raising his eyes from her crotch to her face just long enough for her to see where he'd been looking. She felt her face flush, as she fought the temptation to cover her panties with her hands, since that would just make her look more like a naughty girl than she already did.

Tim's eyes sparkled as he said, "Please take off your shirt next."

Mary opened her mouth to complain, but then thought better of it. She pulled the polo shirt up over her head and off, and dropped it on the floor on top of her shorts. She wore a cream-colored bra, and she knew without looking that her hard nipples were obvious.

"Now the bra," Tim said.

Mary hesitated. "I just want--"

"You said you wanted to make it up to me, right?" Tim interrupted. "Well, this is how you make it up to me."

She looked at him for another few seconds, then reached behind her and unsnapped her bra. Before she could think about it, she pulled the bra away and dropped it on the floor.

Tim's eyebrows lifted slightly as he saw her very nice breasts bounce as she removed the bra. He'd guess that she was a 36-C, but her tits showed no sign of sagging. Her erect nipples were more pink than he'd expected, given her brown hair and olive complexion.

"Nice," he said softly. His voice seemed to make her shiver, and she couldn't stop herself from nervously cupping her breasts in her hands.

Tim smiled at that, and at the red flush that now extended down from her face to the top of her chest. He slowly slid his eyes down to her cream-colored cotton panties. "Just one more thing."

"Do I have to?" Mary said, noting the tremble in her own voice.

"What was I wearing last night?" Tim asked.

"Just your shoes," Mary mumbled. It was quiet for a moment. She looked at him pleadingly, but he just watched her.

Her mind made up, she quickly hooked her thumbs into her panties and pushed them down until they cleared her curvy tush and slid to her ankles. She made a little side-step with one foot, and then the other, and then she was naked in front of Tim.

Tim took in her lean, sexy body, including her brown pubic hair, which was neatly trimmed but not mostly gone, as seemed to be the fashion lately. He could see that Mary was struggling to not drop a hand down below to cover up.

"Embarrassing, isn't it?" Tim asked, and winked at her.

Mary couldn't trust herself to speak, so she just nodded her head.

Tim quickly got up from his chair, surprising Mary. He took her by her left arm and took a step toward his front door, tugging her with him.

Mary was startled, and said, "What are you doing?"

Tim just said, "You'll see," and pulled her briskly out of the living room. She started resisting more as they got closer to the front door.

"Hey," she said, "seriously. What are you doing?"

Tim didn't answer. The closer he got to the front door, the harder he had to tug his confused, naked neighbor. When he reached it, he opened it less than halfway and stuck his head out, looking up and down the street. He could feel Mary's generous breasts and hard nipples press against his back as she cowered behind him.

"What are you--"

Tim turned back to her, leaving the door partly open behind him. She moved back to keep herself out of sight from the street. "The coast is clear," he said. "So I want you to scamper over to your house, get your bottle of vegetable oil from last night, and bring it back here to me. But you are not to put any clothes on before you come back."

"Oh come on!" Mary looked horrified.

Tim just smiled at her. "I ran a lot farther than that last night, totally naked."

"But that was at night," Mary protested, looking past him to the sunny street outside. "It's broad daylight! Someone is going to see me!"

"You weren't worried about that last night, when you oiled me up and spanked my bare ass, laughing the whole time."

"I know," Mary said. "But no one else was going to see you, and I felt bad about it, and there's no way I can--"

"You're babbling," Tim said, amused. "And you didn't seem to feel bad about it when you were groping me and taking advantage of my helplessness to suck my dick."

Mary tugged her upper arm away from and crossed her arms over her chest, inadvertently making her bare tits jiggle enticingly. "You didn't seem to feel bad about THAT," she said, throwing his own words back at him.

Tim quickly stepped to one side, grabbed Mary's shoulders and pulled and then pushed her past him and out onto his front porch. She yelped in horror, and dove back toward him, forcing her way back into the doorway. "Don't! You can't throw me outside naked like this!"

Tim kept his poker face on as long as he could, staring deadpan at his attractive, squirming, blushing, naked neighbor as she clung on to his arm desperately. Finally he grinned and said, "I know."

He half-turned her back toward the living room -- she wasn't resisting any more -- and swatted her adorable bare backside sharply. "Now get back in there."

Mary's hands went to her butt, and she looked back over her shoulder at him as she quickly trotted into his living room, a relieved but questioning look on her face.

"I just wanted you to know what it felt like," Tim said.

"That wasn't funny!" Mary said, rubbing the sting out of her tush.

"You mean it wasn't funny like when I was stuck naked outside last night?"

"Well you were stuck in the window, all oiled up and kicking your legs," she said, with just a hint of a pout. "You've got to admit that that's funny."

"Oh," Tim said, crossing his arms, "so I can put your naked butt over my shoulder, carry you around the front of the house and push you halfway through the bathroom window, and THAT will be funny.

She frowned. "No. That's not what I mean." As her momentary fear of Tim pushing her out his front door totally nude receded, she felt more self-conscious. She dropped her left hand to cover her crotch, and crossed her right arm over her hard-nippled breasts.

Tim forced himself not to smile as Mary tried to cover herself. "Well what DID you mean when you said that you wanted to make it up to me?"

"I don't know," she said hesitantly. "It was really fun last night, and you looked so good, but this morning I felt guilty about doing... those things to you."

Tim nodded. "Okay. But talk is cheap. How exactly do you think you can make it up to me?"

"Well," Mary stammered, "by apologizing, like I'm doing now. And you've made me strip naked... so you've embarrassed me the same way we embarrassed you."

"Not exactly the same way," Tim said evenly. "I mean, you put oil all over me, and then groped and spanked me last night."

Mary didn't know what to say, but she didn't like where this was going.

"Why don't you take your little butt into my kitchen, get my vegetable oil, and bring it back to me."

Mary looked over her shoulder and toward the kitchen, then looked back at Tim, alarmed. "Oh, come on."

Tim uncrossed his arms and put his hands on his hips. "Would you rather I toss you out the door in your birthday suit, and make you bring the vegetable oil from your house?"

She stared at him angrily for a moment, trying to read his expression. "Don't test me, Mary." He had the smallest smile on his face, but she could tell that he was serious.

She opened her mouth, then shut it again, then took one more look at him. Then, with an angry little sound, she turned on her heel and stomped off toward his kitchen.

Tim watched her gorgeous buns bouncing, and he whistled, calling out, "I love the way your butt wiggles when you're angry."

Mary frowned at that, and tried to slow her walk so that she didn't give him the satisfaction. Under her breath she whispered, "I should have stuck that vegetable oil bottle up your butt last night when I had the chance."

"Did you say something?" Tim said, as he followed her into the kitchen.

"No," she hissed through tight lips. "Where's the oil?"

"Top cabinet to the right of the stove." Mary opened the cabinet, and saw that the bottle is on the top shelf. Tim would be able to grab it easily, but he's six inches taller than she is. She got up on her tip toes to try to reach it, blushing at the thought of the view she was giving Tim.

Behind her, Tim moaned softly at the way her calf muscles stood out and her bottom raised and tilted as she stretched upward. He stepped up behind her and cupped her downy right ass cheek in his hand as he softly said, "Do you need some help?"

Mary twitched at his touch and snapped, "No!" and she hopped upward and grabbed the bottle. She turned back to him, sliding her derriere away from his hand and holding the bottle out to him.

Tim took the bottle. "No go into the bathroom and bring out two towels."

Mary caught herself before she could ask why, and turned toward the bathroom. She took several quick steps, then blushed at his previous comment about her "wiggling butt," and forced herself to walk more slowly.

Tim followed her all the way to the bathroom, thinking that he'd happily follow that cute bare bottom no matter where she was going, or how fast she got there.

In a minute they were back in the living room, where Tim pulled a chair away from the table and into the middle of the room. He laid one towel on the floor in front of the chair, and flopped the other one over his shoulder.

He sat down in the chair, put the oil bottle on the floor beside the chair, and looked up into Mary's pretty, red face. "Do you know what comes next?" he asked, playfully.

Mary spoke softly, and through clenched teeth. "I've got a pretty good idea."

"I'll bet you do. And I know just how you feel."

Mary didn't know what to say to that. Tim patted his lap with one hand, and Mary forced herself to bend forward, and lower herself across his lap.

She closed her eyes, feeling a series of conflicting emotions. She was embarrassed to be so exposed and in such a vulnerable position, but she also knew that she was wet, and her nipples were hard, and she felt warm all over. She could feel Tim's erection pressing against her lower belly. It felt good, and warm, and big.

Tim picked up the bottle of oil, uncapped it, and tilted it until a stream fell onto her lower back. Mary hissed at the sensation and a tremble went through her glutes as he moved the bottle lower, drizzling more oil over her sexy, bare buns.

He capped the bottle and put it back on the floor, then dropped his hand lightly onto her ass and began spreading the oil around. "You have a great butt, Mary," he said quietly.

She muttered, "Thanks," and then cursed herself for saying something that sounded so dumb.

"Are you ready?" Tim asked, after her bottom was shiny and slick with oil.

After a moment, she softly said, "Yes."

Tim raised his right hand and gave her round right cheek a sharp spank, and then watched as it jiggled delightfully. At that moment, he had forgotten his humiliating exposure from last night, and how he'd been manipulated, stripped and spit-roasted by four pretty young women.

For Tim, the chance to take charge of his attractive neighbor and give her the bare-assed spanking she deserved somehow felt like it gave him his dignity back.

But at that same exact moment, a few miles across town, something was happening that would lead to a mortifying loss of dignity for poor Tim.

A young woman whom Tim didn't know sat down at her computer and logged on to a popular local site in his town. It was called "City Wiki," and was a combination of an online and continually updating newsletter, a local marketplace, and a community bulletin board.

The staples on the site were people sharing recommendations for local tradespeople, restaurants and businesses; and notices of upcoming concerts and community events; and people seeking or offering goods or services.

The young woman on the computer was named Tracy. She was a pretty blonde in her mid-20s, and she had a small grin and a faint flush of excitement as she clicked to a section of the site labeled "Happening Now."

She began to type. "If you haven't heard about this yet, you're going to thank me for telling you about a new commercial that was recently shot in our town, and that I saw for the first time yesterday."

"Before you stop reading, I know: Why should you care about a commercial, when all of us are bombarded by them all day and every day?"

"Well this one is different. It features a hot male boss and his four young female employees, and the plot involves his employees outsmarting him and undressing him in a really funny and sexy way."

"Better yet, there is a tv version, but there is also an R-rated internet version, and in that one, the hunky boss suffers some VERY cheeky exposure!"

"If you're straight and female, and you've ever had an attractive male boss who you've fantasized about taking down a peg, you're going to LOVE this commercial!

I'm going to put the link to the tv version first, and then the internet version."

"But take my advice: make yourself watch the tv version first. That one is a delicious appetizer, and you should savor it before you move on to watch the "main course" internet version, with its VERY tasteful and much appreciated male nudity!"

Tracy smiled as she proofread her post, then typed in a smiley face after her last sentence.

Then she hit, "Post."

Across town, as a horny, smiling Tim began turning his wriggling, naked neighbor's gorgeous bare bottom an enticing shade of pink, he was blissfully unaware of the humiliating public embarrassment he was shortly going to experience.

Barefan
Barefan
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36 Comments
AnonymousAnonymous9 months ago

Poor Tim ! 🫢🥺 By the sounds of this comment section 😬

AnonymousAnonymous9 months ago

He Could be Fucked up the ass with a hands free cumshot ! 😳

AnonymousAnonymous9 months ago

That Finger up his Ass Could Change Everything on him !

AnonymousAnonymous9 months ago

Cum dribbling out of Tim's poor asshole ! And down his ass and legs and thighs ! 🫢😳 Fuckin Hell ! That would be embarrassing and utterly devastatingly humiliating for the poor hunk ! His Masculinity taken from him 👀🫣

AnonymousAnonymous9 months ago

Just to add Tim is probably due some humiliation where he comes or is forced to or accidentaly comes in his own face and has to taste himself ! 👀🫢🫣😳💦💦💦

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