Lady Boss Humiliates Intern

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Guy gets humiliated by female boss.
2.7k words
4.2
34.2k
21

Part 1 of the 2 part series

Updated 06/09/2023
Created 02/09/2019
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JRob
JRob
1,639 Followers

NOTE -- All naughty activities in this story are completed by people 18 years of age and older. No pets were harmed with the writing of this story. A big thank you to "Snookered" for editing duties.

*****

Lunching with a business associate recently we reminisced about our college days. The classes, the all-nighters to prepare for an exam, fake IDs and women.

Clearly Matt was a player back then, and I was, well, a book worm. I hardly had any luck with the ladies, and spent most of by interactive time with them studying, watching games or walking the quad. Oh, I did date, and actually got lucky a time or two, but it was Matt who was the big ladies' man.

One of the topics other than females we spoke about were our Internships and how they were great preparation for the business world. At our university it was required that students have two internships before graduation. My first was kind of dump, a gofer in the PR department. The internship consisted of copying, filing and mundane work in an office environment. The big highlight was writing a couple press releases about campus successes.

But as a 20-year-old guy it was not very exciting. The following year, however, was a whole lot more memorable. That's when I interned in a VP's office, and Mrs. Hopkins stated on my first day there would be no goofing off, work meant work, and by the same token I'd get to do meaningful work. My role was to be one up from the administrative assistant dealing with questions/comments on various policies.

For my part, I had to become very familiar with policies, and had a lot of face time with Mrs. Hopkins on issues which presented themselves. This was a whole lot different than my past jobs, like ice hockey referee and counter guy at a fast food restaurant.

I loved the face time with Mrs. Hopkins, as she was a brilliant lady. She was also an attractive woman of about 40 who never had a hair out of place. I loved the conversations with my boss, as she taught, listened and gave me enough rope to raise the possibility of screwing up all the while learning. It was a great time.

My supervisor was more than just attractive, she had a certain aura about her that exhibited confidence and the ability to handle a variety of situations. She dressed professionally, but one couldn't help notice her 34C top and legs that were to die for. Her dresses covered her knees but when she sat the leg that showed clearly displayed work in the gym.

Our office did a lot of work for west coast affiliates, so it was often required that our work day end later than east coast time when there were big meetings on the west coast. My work hours on such days would start a couple hours later than normal, and I'd stay in the office a couple hours past normal closing time.

Often Mrs. Hopkins and I and maybe one or two others would remain in the office for these west coast phone meetings. I was fine with that, as I was learning a lot and was happy to be an active participant in these meetings rather than one of 10-12 people in the normal meetings.

As you can imagine, with so much face time with my boss there were times when we'd share stories of our home life. She'd talk about her kids, I'd talk about school or future goals. Every so often she'd ask me about dating and girls, or she'd mention about not getting time outside the home having fun due to children activities. Her husband's job kept him on the road, and she lamented the time without him.

Then came the fateful day when Mrs. Hopkins had to head home early to handle a problem with one of her kids, and she didn't want to cancel a meeting with the group from the west coast. She said I was well briefed, and could handle it on my own. I took that as a compliment...until I royally screwed up and made a wrong interpretation of a policy that ended up costing the company time and money.

The immediacy of the problem and my misinterpretation of the facts led to a decision that was implemented quickly.

"What in the hell were you thinking," said Mrs. Hopkins the next day after calling me into her office. "We have discussed this situation numerous times. How could you screw up so badly?"

"I wasn't thinking. I just screwed up," was my quiet reply. I stammered about misunderstanding the question and answering from the hip, but that just made things worse.

"This has caused me a ton of embarrassment, and it's going to cost us money," said the woman. "I trusted you not to screw up, and this is terrible. This is the third screw up in a month."

We stared at each other before my head hung low.

"Didn't I teach you well? Didn't I trust you to not be stupid? I should fire your ass right now. I can't believe the problems this causes. I'm going to do everything in my power to fix this."

I apologized again and again. I'd forgotten about the two other mess ups, which were nowhere near as bad as the present one, and apologized even more. But there was no mistaking that she was steamed.

"If you were my son or daughter and did this, I'd beat your ass. You would never make such a stupid, nonsensical mistake again!"

I laughed and that just made her angrier. She turned beet red, shot daggers from her eyes at me, and told me she wasn't kidding.

And then came the sentence I can't believe I heard.

"Close the door and lock it. Then, Get your ass over my desk, Jon, right now! Immediately. You are being punished."

Obviously, I didn't believe her, but I locked the door and stood next to the desk.

"Are you stupid? Didn't you hear me? "

She meant business. I didn't think she'd hit my ass, but I did think she was attempting to humiliate me for my mistakes. I did not want to do what she said, but what could I do?

"Take off your belt and bend over the desk. NOW."

Off came my leather belt. I put it next to me on her desk. Then I bent over her desk.

"Drop your pants!"

I should have run to HR, but I lowered me trousers and prepared for the worst.

Humiliated, I felt her hands pulling my underwear down, and soon heard the swish of the belt, which smacked against my bare ass one, two and then three times. These were not the hardest of spanks but they did sting, and it was humiliating to be treated like an insolent child. More swats followed, as she reminded me of my stupidity. After about 10 she stopped, told me to get dressed and went behind her desk and watched as I made myself presentable.

She told me to stand in front of the desk and apologize, and then recite the policies and interpretation that were at issue. She corrected my mistakes, and demanded that I read the policy manual again overnight and return the following morning. At that time, she'd decide as to whether I'd still be interning or, well, sent back to school as a failure. That of course would require an additional semester down the road.

That night I rubbed my ass and realized the swats really weren't that hard nor painful, clearly not as painful as screwing up and then baring my ass for the woman. I was humiliated. I thought briefly of talking to someone about what had happened, but quickly realized I needed to get through the week and convince my boss that I was with the program and wouldn't make the same mistake again.

@ @ @ @

The next morning, I was in the office bright and early, before anyone else in fact. I had studied the documents she had directed me to, I worked on a little speech as my defense, and I was clear in my head that I'd tell her nothing like this would ever happen again.

When Mrs. Hopkins arrived, she said once again how disappointed she was in my actions, that she'd been called by an Executive VP on the problem, and that her ass was on the line if all wasn't fixed immediately. She dismissed me with a wave of the hand and said we'd talk later as she had a lot of work to do to correct the issue.

It was a long day for me, as every minute seemed like five. Mrs. Hopkins stayed in her office most of the day, only barking orders out to her assistant. I thought of what I'd done, the stupid decision, the unprofessional attitude and so forth. It was not a pleasant day.

Remaining at my desk after the office cleared out at the end of the day, I still had not time or opportunity to plead my case to my boss, apologize further, nor even tried to convince her I was the best intern she'd ever have.

I got my work done, but it was difficult to complete. I needed this internship for many reasons, not the least of which without it I wouldn't graduate on time, I'd lose recommendations for future jobs, it would cost be another half year of tuition, housing and so forth.

Just after 5:30 I was sparked to reality with the firm voice of my boss. Mrs. Hopkins was calling and I jumped to attention, gathered some papers and strode to her office. Closing the door, I walked to her desk and stood. She reviewed some papers on her desk before looking up at me, inviting me to sit. I did, and she asked if I'd thought about the dilemma. Immediately I apologized again.

"Do you understand why you are hear? I know you are sorry, but your actions have caused me tremendous problems. The bosses upstairs want my ass, and I can't believe I trusted you. You have been taught well, you had the right information, and you with all that going for you it was a major screw up," said my boss, staring daggers at me. "Firing your ass seems to be the one option that works for me."

Almost begging, I spoke about how hard I work, that I was loyal, that I would continue to learn and help the organization.

She waved my talk off. "But are you willing to do what it takes to make this right?"

"Of course," I quickly replied.

Mrs. Hopkins looked at me, shook her head and seemed to be thinking about a solution. "You know my husband has been traveling all the time and quite frankly has been neglecting some things. I have needs, like any woman. You have a problem. And you can fix that problem."

My boss stood, walked around her desk, and sat back against her desk. She looked into my eyes, then gazed down at her midsection. "You know what to do."

What to do? What the fuck? Was she asking me, telling me, to perform for her? Down there?

"Get to it, boy, take care of business."

Stammering something, I got the idea. It was my casting couch moment. Pushing my chair back, I slipped down to my knees before the woman. Looking up, I saw she was pleased, so I realized what was next.

Reaching out I slipped up her red dress and immediately noticed the black thigh high stockings that had looked so attractive earlier in the day. She moved the dress under her, displaying her French cut lace red panties. I noticed the dark bush being covered by the slinking nothings.

Pressing on, I bent my head over and began kissing and licking her thighs, drawing some oohs and ahs from my boss. Some of the licking was right up against her snatch, and I realized immediately her panties were soaked. I moved my nose up and down her panties over her slit. It was so hot. I mean, I was somewhat humiliated from the actions, I was being bossed around, but it was a beautiful, sexy situation.

Grasping her panties by the side, I slipped them down her thighs and legs. Taking them off one ankle, I left them on floor as I turned back to face her.

In front of me was a woman with a dark brown bush, a true patch that would give the person who came up with the beaver moniker a huge smile. Now, I realize I didn't have a lot of experience "down there" as I'd only seen a couple pussies in my history - other than on web sites - and one was trimmed and the other bushy but trimmed to a point.

Mrs. Hopkins' bush was only slightly trimmed. It was a whole patch of pubic hair that was different and hot for me. I treasured it for a few seconds before my boss gave directions.

"Lick my snatch... now."

Kissing her thighs, I began alternating kisses with licks between her legs. My fingers played with that pubic patch holding her steady and bent forward and licked that sexy snatch as my boss directed. My head worked around her pussy as I licked and licked that tasty treat. Nature took its path, as I heard my boss moaning and directing from above.

My nose slipped into the folds of her pussy, an action which drew a gasp from the woman.

"OH yes, oh yes, suck it, suck me you bastard."

Along the way I moved one hand around to Mrs. Hopkins ass, caressing it, while licking on her pussy. My other hand moved up to her pussy and I slipped a finger up and down her slit before sliding it inside and playing with her clit.

That move caused Mrs. Hopkins midsection to move forward and back to the tune of my mouth and fingers. The gasps continued and soon she was holding my head in her hands and pushing me against her, using my head as an implement of her satisfaction. The woman cooed when I slipped my finger along her ass crack.

I was being used, of course, but I was into the act. While on one hand I was still concerned about my work situation, I was into the performance and wanted to satisfy my boss.

Apparently, that was working, as Mrs. Hopkins kept manipulating my head and soon was cooing and let out another deep gasp. "Damn it, I'm cumming, you bastard. Suck it, lick it, take it you whore."

The woman let out another deep groan and I sort of smiled by my success between her legs. She had an orgasm but remained glued to my face. Bringing her down from her high, I was not sure how to handle but figured staying between her legs was the way to go until she pushed me away. So, I kept licking her snatch and playing with her ass.

She kept rubbing my hand, pushing me toward her slot with some pressure and then releasing. Finally, she pushed me away.

"That wasn't bad, I think you've kept the right to keep your job at least for a little bit," said my boss. "Here's the deal, you can stay here and work for your grade by working hard, and by doing more of what you just did. Perform well, and this will work out. I will handle the guys upstairs. Sound like a deal?"

Of course, I said yes. Looking up at her, I gazed into her eyes and told her I would be a hard-working guy who would do anything needed to make her successful.

Watching my boss get dressed was so very hot. I knew at that point this wasn't to be a one-time thing. I knew how I could keep my job and she could count on me to perform.

She dismissed me, saying she had to head upstairs to plead our case before the two bosses.

JRob
JRob
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AnonymousAnonymous3 months ago

What a cunt! But the spanking wasnt brutal, and he was into the muff diving so good story. even though I hate her guts.

AnonymousAnonymousabout 5 years ago
Nice boss!

Reading about going down on a sexy woman, and your boss at that, is a real turn on. Then when you say you kissed her thighs? That really got me excited. I LOVE nice legs and ti kiss them is very exciting, even if they belong to a sexy black man.

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