Young Boss Tricked & Exposed Ch. 28-29

Story Info
Tim gets tricked out of his jockstrap.
3.2k words
4.54
11.2k
5

Part 16 of the 33 part series

Updated 06/10/2023
Created 08/04/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Barefan
Barefan
271 Followers

Part 28

The moment that Tim was out of sight and down the hallway, the women in the room all looked at each other in delight at their good fortune.

"He looked SO CUTE in that jockstrap!" Mia said.

"The way those straps cover a little bit, but still show everything off!" Kaitlyn agreed.

"I know!" Julie agreed. "It's almost better than if he were completely naked!"

"I wouldn't go that far," Becky said, to a round of giggles. "But it certainly is a nice look on him!"

Danielle and Shawna stepped away from the crowd, gesturing at Pam for her to follow. She did, and the three of them huddled up just out of earshot of the other women. Daniella said, "Do you have our leading man's next wardrobe change?"

Pam grinned, and patted the pocket of her snug khaki shorts. "I've got it right here!"

"Do you really think he's going to go for it?" Shawna asked.

"Once I've got him out of his jock strap, I think he's going to like this better than the alternative."

Danielle and Shawna grinned at each other, and Danielle said, "You mean going completely, bare-butt naked?"

Pam winked, and turned to go to the locker room. And to think that last night she had thought that she might be in big trouble with her bosses!

THE PREVIOUS NIGHT:

After having played her joke with the measuring tape on Mr. Johnson, Pam had walked out of the office in a hurry, eager to get back to her apartment. After getting the young boss hard and then tricking him and exposing him to Shawna, Danielle and Sandy, she was so wet and horny that she wanted nothing more than to get home and in bed, and conjure up the sight of a naked and cringing Tim Johnson while she brought herself to an earth-shaking orgasm!

But she'd barely gotten out of the front door before she heard it burst open behind her. "Pam!" Danielle called.

Pam turned, and saw that Danielle and Shawna had followed her out the front door.

"Yes?"

Danielle nodded back through the office door. "Come back in here. We've got something we need to talk to you about."

Pam stood still for a minute, and felt her heart sink. Had she gone too far by exploiting Tim in his office? Was she in trouble? It was obvious that the women had enjoyed seeing Tim's naked dick bobbing in front of him when they burst in, but what she had done could definitely be considered sexual harassment. Could she even possibly get fired?

She walked back through the doorway and into the office, looking at Danielle and Shawna, but getting only two poker faces. The three of them walked into the conference room without saying a word.

When Danielle had closed the door behind them, they all stood looking at each other for a long moment in silence. Pam looked seriously worried, and finally Shawna couldn't help herself: she broke into a broad grin and said, "Pam, I didn't think you had that in you!"

"Y- you mean..." a confused Pam stuttered, as Danielle also began to smile, "what I did in Tim's office?"

"She means stripping him naked, and then... measuring him?!" Danielle said.

Pam was starting to feel better. "Was that too much?"

"It was definitely too much," Shawna said. She looked at Danielle, then back at Pam. "We loved it, but it was too much. I think that right now, we've got the upper hand on Tim, and I don't expect any trouble from him from what's happened so far. But I'm concerned that we could still push things too far."

Danielle stepped in. "We're just not comfortable being kept in that dark right now. So far your wardrobe plans for Tim have been excellent, but you pushed things tonight, and we'd like to know what the plan is for tomorrow."

"We need to be kept in the loop, because it's going to be our butts on the line if we ever get any blowback from Tim - or even a lawyer that he might engage, if things get out of hand. So we need to know what you're thinking about doing before you do it."

Pam breathed a sigh of relief. "Understood. So for tomorrow's first shoot, the plan is to do what we discussed for the tv version, which is pantsing him and leaving him in some snug boxers. I've got a surprise for the internet version of the exercise machine stunts, but I promise that it won't go too far."

"But I've been thinking a lot about the shower scenes—"

"I'll bet you have," Danielle said, laughing.

Pam blushed a bit, but continued. "And I've got an idea. I know that baring his ass for the internet version can work, but full frontal is out."

"Sadly, yes," Shawna said.

"Well I've been to a few male strip shows in my life, and those gave me an idea," Pam said. "Have you heard of a 'posing pouch'?"

Shawna and Danielle looked at each other. Danielle said, "I haven't heard that term before, but I can guess what you're talking about." Shawna nodded.

Pam reaching into her pocket and pulled out a very brief garment and held it up for them to see. It was basically a thong, with only a string in the back, and a slightly thicker string for a waist band, and a cotton pouch in the front. "It looks like this."

Shawna and Danielle looked at it, and then at each other, grinning. Shawna took it from Pam and held it in her hands. "There's certainly not much to it, is there?"

"Nope," Pam said. "It won't give him any more coverage than the sock and rubber band that I gave him tonight. But it will stay in place better, and that may make him feel a little more comfortable."

Shawna looked at the small scrap of material. "I don't think he's going to be very comfortable in THIS!"

"But I guess it's all relative," a smirking Danielle said. "Compared to his street clothes, wearing this little thing will be a nightmare for him. But compared to the sock and rubber band?"

Shawna said, "So that's why you were measuring him? For this?"

Pam nodded, and Shawna held the pouch up to eye-level, looking it over. "This looks a little on the small side for him."

Now it was Pam's turn to grin. "I know."

Shawna lowered the pouch, and Danielle blurted, "Why, you naughty little sneak! You took out his dick and put a measuring tape to it, and you're still not going to give him enough to completely cover himself?!"

Pam just grinned some more.

Shawna said, "If we're not careful and this doesn't cover him completely, we're not going to get any footage of him in this that can even make it onto the internet."

"I thought about that," Pam said. "And I figure that our editing team can do enough in post to edit out any wardrobe malfunctions that go too far. And besides, if he's got this on, and constantly worrying about inadvertently giving us the full Monty, we're going to get some great, authentic, embarrassed expressions from him."

At that moment, the conference room door opened. Shawna quickly put her hands and the posing pouch behind her back, but they were relieved to see that it wasn't Tim at the door, but Sandy.

"What are you up to in here?" she asked.

Danielle said, "Is Tim still here?"

"No, he just left. He had his head down and was still blushing," Sandy said, smiling. "Hey, listen. I was thinking about tomorrow, and the shower scene. I was worried that since we can't go full frontal, we might have a tough time getting a usable take, but I think I've got a way we can make this work."

The other three women looked at each other, and Danielle said, "How's that?"

Sandy said, "I think I can do enough with steam in the shower to keep the really fun parts hidden. I'm even going to bring a smoke machine in, which will supplement the actual steam, and should give us plenty of coverage."

"So what do you propose that Tim wears for that part of the shoot?" Shawna asked.

Sandy shrugged and chuckled. "If it were up to me, I'd like to see him in his birthday suit! Shoot him in the bare, give all of us a great show, and then conceal everything that we need to do to get an internet-ready version with smoke and careful editing."

"But practically speaking, I'd like to get at least a couple of shots of his bare buns - maybe from enough distance, or with enough steam or smoke to keep us on the safe side of the line. And since fully nude is out, he can wear a towel, or some boxers, or even a pair of shorts for the rest."

Shawna looked worried. "So you're saying that other than a butt shot or two, Tim could be practically fully dressed for the rest of the shower scenes?" Sandy nodded. Shawna said, "Did you talk about this with Tim?"

"No," Sandy said. "I thought I should talk it over with you first."

"Good!" Danielle said. "Because what he doesn't know, can't help him."

"Don't you mean, 'can't hurt him'?" Sandy asked.

Pam smiled and said, "Nope."

Shawna pulled her hands from behind her back and held up the posing pouch. "We've got a better plan."

Sandy laughed, and pointed. "THAT? You're going to put your handsome, shy employee in that tiny thing?" None of the other three women could bring themselves to look any more than slightly ashamed. "I love it!" Sandy said, laughing again. "But is that little scrap of material going to be enough to cover him?"

"Probably not," Shawna said, her poker face back in place.

"But—" Sandy started, and then stopped. She looked from one face to another, an evil grin dawning on her face. "Oh, you ladies are evil!"

BACK TO THE PRESENT:

Pam walked toward the men's locker room, a little bounce in her step as she patted her pocket. She couldn't feel the weightless scrap of cloth that would soon be Tim's only covering, but she knew it was there.

She couldn't wait to show it to him!

Part 29

Entering the locker room, Pam found Tim sitting in front of a locker, wearing a towel.

"Are you ready for this next scene?" she asked.

"No. I can't do it," Tim said miserably. He stood up, and unconsciously drew the knot in the towel tighter. "I know that they're going to want me to go completely naked, and I can't do that!"

"You don't have to worry about being fully nude," Pam said. "I've come up with a solution for you."

Tim looked at her defiantly. "If it's that sock again, I'm out. That looked ridiculous, and I could feel it slipping several times. If I'm going to be getting it wet in a steamy shower, it won't stay on."

"It's not the sock. I've got something better."

He eyed her warily. "Let's see it."

"Absolutely. But first, give me your jock." She'd guessed that he still had it on under the towel, and as his hands instinctively went to his waist, she knew that she'd guessed right.

"No way! Tim said. "That's all I've got, other than this towel. And I know that those sneaky women won't let me keep this on for very long!"

"C'mon, Tim," Pam said. "You know you can't wear a jock strap in the shower. Nobody showers in a jock!"

Tim crossed his arms. "Let me see what you've got for me first."

Pam crossed her own arms. "We don't have time for this. Either give me your jock, or I'm going to call the girls in here, and I think they'll be very happy to take your towel and your jock both!"

Tim fumed, but he knew that she was right. The two stood for a long moment, staring at each other. Handsome, well-built Tim was a full head taller than petite Pam. But he was half-naked and she was fully clothed, and they both knew that she had the upper hand.

She watched him thinking about it, in suspense, before he finally dropped his head, and reached up under his towel and fumbled around for a few seconds. Then she watched his jockstrap fall down from beneath the towel and land with a soft slap at his feet. Even though he hadn't shown any skin, watching this hunk reluctantly surrender his jockstrap was one of the sexiest sights she'd ever seen.

She quickly stepped forward and bent over, and Tim took a startled half-step back. She yanked on the jock and gave his calf a light slap. He stepped out of it, and she grabbed it and stepped away from him.

"Okay," he said. "Now what do you have for me to wear?"

She reached into her pocket and then held the tiny piece of cloth out in front of her.

His eyes widened in horror. "What the hell is that?" he asked.

"It's called a posing pouch," she said in a matter of fact tone. "A lot of bodybuilders wear them in competitions."

"It looks like something a male stripper would wear!"

"Them too," Pam admitted with a small grin.

"I can't wear that," Tim moaned.

"Sure you can. It's got a sturdy string that goes down the back, and another one that goes around your waist, so it's a lot more secure than the sock that I rigged up yesterday."

"That's great, but it looks like it will hardly cover anything!"

"That's why I measured you last night, to be sure that it would fit. It's more stretchable than it looks. Try it on." She tossed it to him, and he caught it and looked at it.

"This is what you measured me for?"

"What, did you think I was just groping you to get a cheap thrill?" Pam asked, smiling knowingly.

"The thought crossed my mind," Tim said acidly. "But I don't think this is going to fit."

Pam put her hands on her hips, and gave him an exasperated expression. "There's one way to find out."

Tim groaned, but then he turned away from her and bent over. He lifted one foot and pulled one string loop over it and up to his ankle. Then he stepped into the other side, and pulled it up gingerly. As he pulled it higher, he accidentally lifted the bottom of his towel on one side, giving Pam a quick peek at one firm bare butt cheek before quickly pulling down that bit of the towel again.

As Pam watched, he did an amusing little wiggling dance, with both hands twisting and maneuvering under his towel. When he was finally satisfied, he looked back at Pam over his shoulder, as if making sure that she wasn't peeking, and then opened the front of his towel and looked down. "Oh, hell no!" he said. "I don't know what you were measuring, but this isn't right."

"Let me see," Pam said, trying hard to keep the smile off of her face.

"It doesn't fit," Tim said.

"Let me see!"

"I can't."

"Let me see, or I'm going to rip that towel right off of you!"

"Promise you won't laugh?"

Pam put on a solemn expression and crossed her hand over her heart. "I promise."

Tim was blushing furiously and his hands were shaking slightly as he turned to face her, and held open his towel.

Pam's eyes dropped, and then widened. "Oh my!" she said, and covered her mouth to stifle a giggle.

"You said you wouldn't laugh!" Tim snarled, and pulled the towel shut.

"I'm sorry. I thought you were exaggerating."

"Well, I'm not! This doesn't fit at all!"

"Let me see," Pam said gently, and coaxed him into opening the towel again.

The cotton pouch clung to his balls and the thick shaft of his mostly erect dick very revealingly. Even though the cotton did stretch, the top inch of him was sticking up above the top of the pouch.

"Why are you so hard?" Pam asked.

"Why did you put that measuring tape on me if you couldn't get any closer than this?"

"It was very distracting... handling you like that. Is it possible that It's... bigger now?"

Tim snorted in exasperation. "My dick didn't grow overnight!"

"I know. I'm sorry. But why are you so hard?

"I don't understand it," Tim said. "I'm so damned embarrassed, you'd think I'd be shrinking to escape the shame."

"You are certainly NOT shrinking!" Pam said.

"What am I going to do? I can't have all of those women see me like this!"

"Can't you make it softer?"

"I wish! It's like it's got a mind of its own! But I NEED to get it to do down."

"I agree," Pam said. And then she shocked Tim by stepping forward and kneeling in front of him, reaching out toward him as she did so. Before Tim knew what was happening, Pam had grabbed the top of his shaft with one hand and tugged the pouch down and out of the way with the other.

"What are you do-" he began, but his voice caught in his throat as she spit on her hand and started rubbing it up and down his dick.

She turned her pretty green eyes up to him and said, "I'm trying to help. You've got to get rid of this gigantic hard-on, and there's only one way I know to do that."

"You can't just—" Tim began again, but when Pam tightened her grip on him and began to stroke faster, he once again caught his breath. He felt paralyzed, and unable to close the towel that he was holding open on both sides, watching as Pam kept looking into his eyes, as she jerked him off.

After a minute or more, Tim managed to say, "They're right outside. They could come in at any minute."

Pam nodded her head. "I know what you're saying. We've got to speed this up." Her heart was pounding in her chest, and as soon as she thought of it, she forced herself to follow through before she lost her nerve.

And as Tim watched in disbelief, pretty Pam, kneeling in front of him with his dick in her hands, leaned forward and engulfed his head and the top of his shaft into her warm, wet mouth. "T- that's not what I m- m- meant—" Tim said.

Pam hollowed her cheeks with one aggressive suck, and Tim felt her tongue moving across him, before she slipped several inches further down his shaft.

Tim felt himself get weak in the knees, and he started to close his eyes.

"Are you two all right in there?"

Tim's eyes snapped open, and Pam pulled back off of his cock with a comical popping sound, her eyes as wide as his.

They both recognized the voice as Shawna's, and for an instant Pam stared up at Tim while he stared down at her. Then she quickly leapt back and stood up. For one more second Tim stared down at himself.

Pam had only made things worse! He yanked the pouch back over to cover up, but now two inches of himself stuck out of the top, his skin tight and shiny with Pam's saliva! He yanked the towel closed and knotted it tight just as Shawna rounded the corner.

Barefan
Barefan
271 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
10 Comments
Cyberweasel89Cyberweasel89about 1 year ago

I really like how the way Pam felt while jerking and sucking Tim off was written. It helped me as the reader see that this was exciting for her as well, while also showing that as much as she had control over Tim in that situation, she didn't have full control over the situation. That kind of thing makes Pam feel more relatable and human, which is rare for a woman in a CFNM story.

KingflintKingflintover 3 years ago
Wonderful

Story is great when is next addition

AnonymousAnonymousover 3 years ago
I love these women!

I like how they are always tricking Tim into more embarrassing positions. Keep finding ways to get him naked girls, we're counting on you!

AnonymousAnonymousover 3 years ago

I've been loving the progression so far, keep it coming!

AnonymousAnonymousover 3 years ago
Finnlly

At least now he's getting some action. All these women drooling over him and not even a hand job to orgasm. Seriously?

Show More
Share this Story

Similar Stories

Joe's Embarrassment Continues Joe is naked again in public.in Exhibitionist & Voyeur
Entertainment for the Party Gay themed story of guy stripping at party.in Exhibitionist & Voyeur
Everybody Wins Arrogant Thomas has a humiliating vacation!in Exhibitionist & Voyeur
The Streaker Tricked into streaking leads our hero to more humiliations.in Exhibitionist & Voyeur
Classroom Erection Hot shot gets knocked down and embarrassed.in Exhibitionist & Voyeur
More Stories