Jack had been working at his firm for just under a year when the new class of interns were first hired. The new class was a group of five interns, four of which were male, and the last one, Juliet, was a woman. Juliet had just turned 20, was rather tall, and had long dark hair, that was rather thick and slightly curly. Juliet was somewhat chubby, with a bit of a stomach and a slightly pudgy face. Her things were thick and strong and her arms clearly had strength behind them. But what immediately stood out to Jack when he first met Juliet was how large her breasts were. Juliet was not the only chubby girl in the office, but none of the other girls had boobs anywhere near as big. They were large and round, and although they sagged a little, they looks surprisingly perky considering their size.
Jack had been working for nearly a year and although he was often nervous around his bosses, he generally did good work and had been starting to get a hang of things. As such, he was very involved with training the new interns. To Jacks luck, within a few weeks, Juliet was assigned to work on a project 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 more busy at work, dealing with his own work as well as training and supervising Juliet, that he began to fall behind on his own corporate mandated training. Finally, in a week where he missed two different trainings, he was called into Stella'a office, one of the Partners at the firm.
"Jack, you've been missing a lot of trainings recently, thats 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 have to 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 with confidence and had a stern demeanor to her that intimidated most of the younger employees.
"I'm sorry about that, I'll try to catch up this week, I've just been busy with this new project and I've been spending a lot of time training Juliet which isn't helping."
"Oh, so 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'a office a minute later.
"Hello Stella, is there something you needed from me?" Juliet asked.
"Yes, Jack has been falling behind in his training and he seems to think that 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 is perfectly capable of getting all of his work done, and he will be finishing that training today even if he has to work late. But before he does that, he needs to be disciplined. I trust that 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 across the country, but Jack had always thought it was just a threat - not something that would actually happen to him. Surely Stella wouldn't actually give him a paddling right in the office just for missing a few trainings?
"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. Now you have missed two separate deadlines just this week, so that 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 think I'm gonna bump it up to eighteen with the paddle!"
Jack had nothing to say to this, 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 just hoped that she would be asked to leave before the paddling began...
"I'm sorry, I promise I'll get everything done today, this won't ever happen agai-"
"I'm sorry but it's too late for that," Stella cut him off. "I should have intervened earlier but like you, I have also been rather busy. In fact, I'm still quite busy and I don't think I have the time today to give you a proper spanking. So I am going to 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 that 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 before?
"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 I assume?"
"Yes, I've seen my mom paddle my older brother a few times as well."
"Alright, Then why don't you take this paddle, and then walk Jack over to conference room D. That one is sound proofed 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 anyways catching up on his work. If he gets out of line at all or tries to argue with you I give you permission to give him additional whacks."
And 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 while 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.
They finally entered the conference room, Juliet closed and locked the door, then turned to Jack. "I've never heard of anyone actually 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 soo 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 definitely 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 second passing she gained confidence and she watched Jack stutter and look at the ground afraid to make eye contact.
"You cant make me do that, she specifically 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 day dreamed about seeing Juliet's boobs. He had probably stared a little too long a few times but as far as he knew, he had never gotten caught.
"Don't think I haven't noticed your staring, I know you want to see them."
Well so much for that. This was already a pretty shitty situation though. That paddle looked really 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 then patted her lap, indicating for 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 Jacks eyes. Jacks 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. Jacks 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 was expecting!"
"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 REALLY 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, well why don't I make this even better for you then. 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."
