Spanked By The Intern
By Rosey01.

Jack had been working for nearly a year, and although he was often nervous around his bosses, he generally did good work and started to get the hang of things. As such, he was very involved with training the new interns. To Jack’s luck, Juliet was assigned to work on a project within a few weeks with him. Jack talked with Juliet every day, training her and occasionally stealing a glance at her boobs when she looked away. On days she wore a more low-cut top, Jack would find more excuses to come over to her desk and try not to get caught staring.
Over the next few weeks, Jack got busier at work, dealing with his work and training and supervising Juliet. He began to fall behind on his corporate-mandated training. Finally, in a week, when he missed two trainings, he was called into Stella’a’s office, one of the Partners at the firm.
“Jack, you’ve been missing a lot of training recently; that’s not something that we are ok with; you still have a lot to learn, and if you want to move up in this company, you must keep learning and being trained.” Stella was in her mid-40s and was tall and slender with long blonde hair. Her overall look was very polished and put together. She always wore high heels that made her taller than most of the men in the office, and every piece of clothing she wore always looked classy and expensive. She spoke confidently and had a stern demeanor that intimidated most of the younger employees.
“I’m sorry. I’ll try to catch up this week. I’ve just been busy with this new project and spending a lot of time training Juliet, which isn’t helping.”
“Oh, you think Juliet’s fault that you’re falling behind?
“Well, no, I don’t mean it like that. It’s just-”
“Why don’t I call Juliet in here, and we can sort it all out.”
Stella messaged Juliet, and she responded immediately and was in Stella’s office a minute later.
“Hello Stella, is there something you need from me?” Juliet asked.
“Yes, Jack has been falling behind in his training, and he seems to think it’s because he has been asked to help train you.”
“Oh, I’m so sorry, I didn’t realize-”
“Don’t you worry? Jack can get all his work done, and he will finish that training today even if he must work late. But before he does that, he needs to be disciplined. I trust you both have read the code of conduct and know the punishment for missing deadlines.”
Jack felt a lump in his throat. He knew Stella was talking about the corporal punishment section. It was a relatively new policy that had been becoming more common at companies nationwide, but Jack had always thought it was just a threat – not something that would happen to him. Surely Stella wouldn’t give him a paddling right in the office just for missing a few pieces of training?
“Ummm- yeah, I think I know what you’re talking about,” Jack meekly replied.
“The Code of Conduct clearly states that when an associate misses a deadline, they can be paddled over the pants up to six times. You missed two separate deadlines just this week, which would equal twelve. Plus, I don’t appreciate how you tried to blame Juliet for this and don’t think I didn’t notice two weeks ago when you showed up late to work three days in a row. So I’ll bump it up to eighteen with the paddle!”
Jack had nothing to say, although he never expected that this could happen to him. He knew what he had agreed to when he first joined the company. He just wished that Stella had done this in private instead of bringing in Juliet to watch him be scolded. He hoped she would be asked to leave before the paddling began.
“I’m sorry. I promise to finish everything today. This won’t ever happen again-”
“I’m sorry, but it’s too late for that,” Stella cut him off. “I should have intervened earlier but have been rather busy like you. I’m still quite busy and don’t have time today to give you a proper spanking. So I will have to ask Juliet to paddle you instead.”
Jack couldn’t believe what he was hearing. It was one thing to be spanked by an older woman in a position of authority over him, but to be spanked by a woman who was even younger than he was, an intern, someone that he was an authority figure to, that was something Jack couldn’t believe. Unfortunately, Jack was still speechless and couldn’t get the words out to protest.
“Juliet,” Stella continued, “Have you ever spanked anyone?
“No, ma’am, I’ve been spanked plenty of times when I was younger, though,” Juliet quickly replied.
“Ah, excellent. Then you know how it should be done.
“Yes, I’ve seen my mom paddle my older brother a few times too.”
“Alright, then, why don’t you take this paddle and walk Jack over to conference room D. That one is soundproofed and has no windows, so you two will have plenty of privacy. Take as long as you would like. Jack will likely be here all night anyway, catching up on his work. If he gets out of line or tries to argue with you, I permit you to give him additional whacks.”
With that, Stella handed Juliet the paddle, and Juliet opened the door and led the way to conference room D. Jack looked at the ground, trying not to make eye contact with anyone as they walked past several rows of desks. At the same time, Juliet openly held the paddle with no discretion. Jack heard some quiet giggling and whispers, but luckily, nobody said anything to him. He was sure that it would be the talk of the office for the rest of the day and probably the rest of the week.
When they finally entered the conference room, Juliet closed and locked the door and turned to Jack. “I’ve never heard of anyone getting spanked here. Is this common?” Juliet asked Jack.
Jack was still looking at the ground, too embarrassed to even look Juliet in the eye. “I know it’s something that can happen, but people don’t talk about it much.”
“Oh my God, you look so embarrassed right now,” Juliet teased Jack, enjoying the role reversal of having power over the man who has been reviewing her work for the past month. “We’re you never spanked growing up?”
“I wasn’t. My parent didn’t believe in it.”
“Well, my parents certainly did. I was spanked pretty often, and I was never spanked over the pants; it was always pants down, bare bottom, over my mom’s knee. What do you think about that?”
“I think we should just do what Stella said.” Jack was almost shaking at this point. The thought of pulling his pants down in front of Juliet made him want to run home and never come back to work.
“Well, I have the paddle, don’t I? I’d probably listen to me,” Juliet chuckled. With each passing second, she gained confidence, and she watched Jack stutter and look at the ground, afraid to make eye contact.
“You can’t make me do that, ” she said over the pants.”
“Well, we don’t have to tell her everything, do we? I’ll tell you what, if you let me spank you on the bare, I’ll do it with my hand instead of the paddle”.
“It’s not about the paddle; I just don’t want you to see me naked; it would be too embarrassing.”
“Ok, well, if it’s about that after I finish spanking you, I’ll show you my boobs. That way, we’ll be even.”
Jack suddenly looked up for a second. He had often daydreamed about seeing Juliet’s boobs. He had probably stared a little too long a few times, but he had never gotten caught, as far as he knew.
“Don’t think I haven’t noticed you staring; I know you want to see them.”
Well, so much for that. This was already a pretty shitty situation, though. That paddle looked painful, and Jack knew he was getting spanked one way or another. So might as well get to see some boobs at the end of it, he figured. “Are you sure about this?”
“Come on, you know you want to see them; I have the biggest tits in the office, don’t think I don’t see how guys look at me.”
“Ok, fine, you have a deal.”
“Excellent.” Juliet pulled the chair to the middle of the room and sat down. She hiked up her skirt and patted her lap, indicating Jack to lie over it. Jack walked up, about to climb over her legs, when she put her hand up. “pull your pants down first,” she commanded, looking directly into Jack’s eyes. Jack’s already red face found a way to get even redder. He quickly pulled his pants down and climbed over her legs. Juliet quickly repositioned Jack so his butt pointed up in the air. She then tucked her fingers under the waistband of his boxers and swiftly pulled them down. Jack’s penis was semi-erect and bumped against Juliet’s leg, although she didn’t say a thing about it. She quickly began to smack with butt with a surprising amount of strength.
SMACK
SMACK
SMACK
She was alternating cheeks at first and then switched to smacking one cheek 10 or so times in a row and then slapping the other cheek 10 or so times. Jack was trying to stay quiet at first but began to shout and cry out in pain as the spanking continued, and Juliet showed no sign of stopping.
“You’ve spanked me long enough. This is more than Stella expected!”
“Well, Stella wasn’t expecting you to see my tits either, so I think you better hold still, or I’m not showing you anything.”
Jack couldn’t say anything to that. After suffering through this much of a spanking, he needed to see her boobs for it to be worth it.
“Oh boy, you want to see my tits don’t you” Juliet laughed and smacked him two more times extra hard.
“OW! I mean like you said, biggest in the office.”
“Bigger than you’ve ever seen, I bet!”
“I think so, yeah.”
“Alright, why don’t I make this even better for you? In my bag, there’s a hair brush. You hand me that, and i’ll give you 30 extra hard whacks, and then I won’t just show you my tits; I’ll let you jack off to them.”
Jack, face down, holding his body up with his hands, saw that Juliet’s bag was beside him. He saw the hairbrush; it was wide and made of thick wood. Jack knew it would hurt, but he also knew that when he saw Juliet’s boobs, he would be rock hard, and if he didn’t jack off, he would spend the rest of the workday with blue balls. Jack nervously grabbed her hairbrush and handed it to her.
“Haha, I knew you would do it. You boys are so predictable. Maybe if you spent less time staring at my cleavage and more time doing your training, you wouldn’t be over my knee getting spanked right now.” Juliet raised the hairbrush above her head. “I want you to count these strokes out. After each spank, I want you to count it out and say: Thank you, Miss. May I have another.”
Jack’s throat fully dried out; this would surely be the most embarrassing moment of his life. As much as he wanted to see her boobs, but was unsure how he would be able to show his face at work ever again after this. However, his thoughts were quickly interrupted:
SMACK!
The hairbrush came down even harder than he was expecting. The hairbrush struck down right in the middle of his right cheek and had a far more powerful sting than her hand. His already bright read-ass could hardly take that first hit, let alone 29 more.
“EXCUSE ME!” Juliet exclaimed. “Aren’t you forgetting something?
“One! Thank you, Miss, may I have another” Jack managed to stammer out, his face cheeks just as red as his butt cheeks.
“Since I had to remind you, that one doesn’t count. Start over.” Juliet quickly smacked his right cheek again with as much force as before.
“One! Thank you, Miss, may I have another!” Jack knew better at this point than to argue with her and did exactly as she said, hoping not to get any more extra strokes.
SMACK
“Two! Thank you, Miss, may I have another!”
SMACK
“Three! Thank you, Miss, may I have another!”
SMACK
“Four! Thank you, Miss, may I have another!”
SMACK
“Five! Thank you, Miss, may I have another!”
Juliet continued, alternating cheeks with each smack. Jack’s legs were kicking around uncontrollably, but he knew better than to move out of position or try to block the spanks. As Juliet continued, she began to target the upper portion of Jack’s thighs. She remembered from back when she was still getting spankings that that area hurt the worst. Tears began falling down Jack’s eyes.
SMACK
“Twenty-four! Thank you, Miss—may I have—a-another!” Jack could barely get the words out, stammering between tears. He was in more pain than he had ever been and was just trying to wait out the last six spanks.
“Boys like to say they’re tougher than girls, but I stopped crying when I got spanked by the time I was a teenager! But my older brother would cry every time, even when he was 18! I stopped getting spanked long before then, but my Mom believed that boys needed to be spanked more often to stay good.”
The tears only continued to flow as Juliet’s arm seemed to get stronger as the spanking went on. The pure humiliation of Jack having to present his naked bottom to a woman younger than him, combined with the pain he was feeling in his bottom, was too much for Jack to take. Juliet mocking his crying only emasculated him further, ironically making him cry even worse.
SMACK
“Twenty-five! Thank you, Miss, may I have another!”
SMACK
“Twenty-six! Thank you, Miss, may I have another!”
SMACK
“Twenty-seven! Thank you, Miss, may I have another!”
SMACK
“Twenty-eight! Thank you, Miss, may I have another!”
SMACK
“Twenty-nine! Thank you, Miss, may I have another!”
SMACK
“Thirty! Thank you, Miss, may I have another!”
“No, I think that’s enough,” Juliet unceremoniously pushed Jack off of her lap, and Jack kneeled on the floor, his hand covering his naked penis.
“What are you covering up for? Let me look.”
“We never agreed to that. We agreed that you would show me your boobs.”
“Yeah, and you were gonna jack off; how are you gonna do that without me seeing your dick?”
Jack’s face turned red as he realized she was right, she would have to see his penis, but he was hoping that somehow he could get out of it.
“Ok, fine, but let me see your boobs first!”
Juliet unbuttoned her shirt, fully exposing her large breasts, hidden behind a white bra. Her breasts looked massive, even on her rather wide torso. Her stomach was also exposed, and her large belly was remarkably smooth; her fat rolls looked inviting, and he wished she would take her skirt off so he could appreciate her thick thighs as well.
Even wearing her bra, she was showing a lot of cleavage, and Jack took a long look, getting lost in her cleavage. Jack was fully hard by this point, even with her bra still on.
“Ok, you like what you see so far. Let me see your dick, and I’ll take my bra off.”
Jack knew he couldn’t hide it any longer; even though his dick was fully hard, it was a rather unimpressive 4 inches. But at this point, he was so horny he would do anything to see her tits and quickly uncovered his penis for her.
Juliet looked flustered at first, then giggled slightly before holding back. She looked amused, almost embarrassed, on behalf of Jack but then became puzzled, then almost angry.
“So you knew this whole time that this was your dick, and you still thought you deserved to see my tits! I was under the impression that this would be a fair trade-off. I have the biggest tits in this whole office, I wasn’t expecting you to have the biggest dick in this office, but I figured you’d at least be respectable. Me showing you my tits is worth far more than that spanking you just got, and that little babydick isn’t enough to make up for it!”
Jack couldn’t look up from the ground. He wanted to argue with her but was so overcome with shame and too nervous to look up at Juliet and dare challenge her. After she reduced him to tears over her knee, she was now tearing apart his undersized penis while confidently standing over him in her bra exposed with no shame, and great confidence in her body, especially in comparison to Jack.
“Aww, I’ve never seen a man look like you. You can barely even speak, can you?”
“P-please, I did everything you asked,” Jack stammered.
“I’m a lady of my word, you can jack off to my tits as I said, but the bra stays on, and try to make it quick.
Fully defeated at this point, Jack accepted that this was his position and began to jack off. Despite the humiliation, his penis was still rock hard, and he wanted to get something out of this humiliating experience.
Juliet’s breasts still looked great behind the bra, and Jack knew he would have no trouble cumming to them. Although he wanted nothing more than to see behind her bra, he was afraid of what Juliet might do if he asked her again.
“Hurry up, I’m gonna give you one more minute, and you better cum by then, or I’m leaving you to finish by yourself!” Juliet then squeezed her boobs together and shook around a little. “There! Is that enough for your little guy!”
It was enough. Jack came almost immediately.
“Alright,” Juliet said as she buttoned her shirt back up. I’ll tell Stella we’re all done. You can get dressed, and then you have quite a lot of work to get done tonight, don’t you?”
The End.
*AI has edited this story to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.