Story 18
Summary: Darlene Madison-45 year old MILF, successful entrepreneur and industry leader
Andrew Thomas-21, seemingly awkward but handsome new personal assistant
Amazing Darlene Madison has climbed the ladder to the top rung of her profession.
As a successful entrepreneur, she has everything and more than she ever imagined.
The only piece missing is a robust sex life.
She hires young, geeky Andrew Thomas as her temporary personal assistant so she can free up some personal time.
To her surprise, Andrew assists her with more than just her exhaustive work load.
MILF, younger man, large cock, blow jobs, pussy licking, rough sex, sixty-nine, kissing, titty sucking, fingering, doggystyle, missionary position, sex in office
Cheers to me! I had made it! Professionally speaking, I had it all.
I built my Madison Media almost as if he could read my mind.
He was a brilliant assistant and with the right mentoring, had limitless potential in our field.
Andrew's employment was beginning to make room in my schedule for the personal time I craved.
He arrived early and left late which led me to believe that his personal life was also a bit lacking.
Andrew was twenty-one years old. I found him a little nerdy and awkward at first.
It was a shame because underneath his professional demeanor, was a handsome young stud waiting to burst out of his shell.
Some girl would be quite lucky to land him.
At the moment though, he was completely dedicated to his job.
Tonight was going to be another late night for us.
We had a few items to go over before we could officially close the books on another successful campaign for my oldest client.
It was the first such achievement during Andrew's brief tenure.
I brought in a bottle of expensive champagne so we could celebrate.
He had been working so hard that I thought it would be a great idea that we let our hair down a bit.
I was quite a taskmaster and I wanted to show Andrew how much I valued his contributions to my company.
I thought it was important that he know that I wasn't all work and no play if I wanted to secure his continued loyalty.
We zipped through the agenda quickly. Andrew was no joke when it came to getting things done.
It was after 8 p. m. when we finally finished and we were the only two remaining in the office.
It was time to break out the champagne. I grabbed the bottle and two champagne flutes and set them on the table.
“Hey, what's this?” Andrew asked completely surprised at the gesture.
“What does it look like? It's a celebration. I closed the deal and I wouldn't have been able to do it without you. Will you join me for a drink?”
“Sure! Of course! Thank you!”
I poured us both a glass, kicked off my heels, and threw my feet onto the table. I leaned back in my chair and watched as Andrew gulped down his first glass. I poured him another and he quickly tossed that back as well.
“Slow down buddy,” I teased. “Are you in a hurry to leave?”
“Not at all, Ms. Madison. It's just that it's been such a long time since I've had a chance to sit back and enjoy a drink. I stay busy. Plus, I can handle it. It's going to take more than splitting a bottle of champagne to get me drunk.”
“Yeah?” I considered that my cue. I pulled out my secret bottle of tequila and poured us both a shot.
We talked for the next several hours over that bottle of tequila.
Andrew was quite a remarkable person and he was rather tempting.
After polishing off the remainder of my liquor, he was beginning to look better and better.
He had taken off his jacket and loosened his tie hours ago.
Underneath his normal suit and tie, he seemed to be pretty fit.
His features stood out even more now that the business wear had been removed.
I was also beginning to notice how smoldering his dark brown eyes were once he disposed of his glasses.
His lips seemed more juicy and succulent as well.
I was right. Underneath that nerdy, professional exterior, there was a hot young thing.
I couldn't help but survey the handsomeness that was sitting right in front of me.
I was taking him all in, scrutinizing his entire body.
That's when I noticed it, the large bulge in his slacks.
I stared at it. I probably even drooled a bit.
There was undoubtedly something under those trousers that could use some attention.
It made me fondly recall the last time I sucked a big dick.
I was hoping that his dick would magically fall out of his trousers so I could test my long dormant dick sucking skills.
I couldn't take my eyes off of his erection and to my embarrassment, he noticed my stare.
“I'm sorry, I didn't mean to stare. That was pretty inappropriate. Maybe we should wrap this celebration up and get out of here,” I suggested.
“Too bad, I was enjoying myself. And, I was flattered by the staring. I don't think anyone has ever looked at me like that. For what it's worth, the bulge is for real. I do have a large package and I know exactly how to deliver it.”
“Is that so?” I coyly inquired.
“That is so Ms. Madison. I hope I'm not stepping too far out of line but I think you're hot too. I've been checking you out, just discreetly. Discretion is one of my specialties, among a variety of other things.”
“Let me stop you there, Andrew. I'm not sure if this is a line we should cross. I have a lot to lose.”
“You have even more to gain,” he interrupted. “I promise, you can trust me. I may look shy and nerdy but that's the work side of me. The real me will fuck the shit out of you if you let me.”
“Wow! That's quite an offer, Andrew. Are you sure you can live up to it? After all, I do have years of experience over you. Are you sure you can handle my old ass?”
“There's nothing old about you at all, Ms. Madison.”
The hours of drinking had handicapped my inhibitions.
Words just fell out of my mouth that I never imagined I would ever say to an employee.
“Well then, as long as you promise discretion, why don't you take that big dick out of your pants so I can suck it?”
“I thought you'd never ask,” he replied as he stood up to unbuckle his belt and let down his trousers.
I dropped to my knees just as he freed his monstrous cock.
It was stiff as a board, pointing straight out at me.
It was long and thick and beautiful. I dwindled not a moment.
I grabbed him by his bare ass and let the petrified rod brush itself across my lips.
I was stalling for time as I plotted my attack.
I knew he was expecting a superb blow job and I didn't want to disappoint.
With both hands, I began to stroke the stone-hard beast. I massaged it slowly and sensuously, reveling at its immense hardness and size. I twisted my hands all around his manhood as they glided up and down it. I cupped his balls when my hands reached the base of his swollen shaft.
I held his enormous fuck pole by the bottom as it continued to aim itself towards my mouth.
I licked the tip of his dick before sweeping my tongue along the protruding vein that ran down it.
I tickled his balls with my tongue and then reversed motions until my tongue found its way back to the head of his cock.