Meg is stressed out, too

As you approach her office, you can tell that Meg's neck-deep in her own issues. An uncharacteristic scowl is on her freckled face. She notices you step towards her office and rolls back, attempting to cover her frustration.

"Hey Meg, you busy?" you ask. "If so, I can just ask you tomorrow."

"Kinda." she sighs. She rolls back from her desk in defeat and looks at you. "Just my stupid ex and my half of the Gutterman file." She reaches her hands behind her head and pulls her hair up.

"Yeah, that case is driving me nuts!" you reply. "I can't, for the life of me, figure out where this $3,500.00 went."

"You're only missing $3,500? I'm missing a lot more than that!" she replies. She then sighs. "I've been looking at this thing for hours, and frankly, I'm tired of it. I'm also really freakin' hungry. What time is it?'

You glance at your watch "7:05."

"Geez, this time of year, you can't tell" she states as she points out the darkness outside of her window. "Hey, would you want to grab a bite to eat?"

"Sure, works for me." you state. "Anything you have in mind?"

"Acutally, there's this place I have wanted to check out..." Meg and you share a few things in common, one of which was appreciation for good food. "There's this new hole-in-the-wall diner down the road by my apartment, would you want to come check it out?" She suggests.

"The Red Star? Yeah, I've wanted to check it out ever since I saw the review in the paper!" you reply.

"Yeah, that's the place! How about you ride with me?"

"Sure thing, let me lock up and grab my coat." You head back to your desk, shut your computer down and grab your jacket. By the time you're finished, Meg has grabbed her things and locked up her door. The two of you head out of the office into the chilly night of the parking lot and head towards her car. You get in the passenger's seat as Meg starts up the car and heads down the road towards the diner.

On the way, you catch up on what's going on in each other's lives. Really, more of what's going on in Meg's life. With two daughters in college, Meg suddenly finds herself with a lot of time on her hands. It seems the year-end crunch at the office has been a blessing in disguise for the both of you.

You reach the diner and Meg shuts off the engine. "Alright, here we are." She says. As the two of you approach the front door, you act the gentleman and hold the door for her. "Thank you kind, sir" she states.

"Anything for a lady," you casually reply.

You enter the greasy spoon, order your meal and chitchat about various topics as you wait for, and eventually, through your meal. Conversation has always flowed between the two of you like old friends rather than a manager and her employee. Unfortunately, she broaches a sore subject.

"So why in the world would Eileen have cheated on you?" she asks. You cringe. "I'm sorry, I probably should've phrased that better."

"Eh, I need to get over it sooner or later," you reply. "Preferably sooner. Eh, dunno on that one. Something about 'first loves' or some bullshit like that."

"Well, personally, I think she fucked up. You're honestly a great guy. If I was 10 years younger and not your boss...wait, never mind..." As she trails off, your cock stirs in your pants.

"Whoa, Meg...you can't leave me hanging on that one! If you weren't my boss?" you ask.

"Well, what I was going to say was that...well, I think you're kinda hot. But I'm too old for a guy like you to be interested." By now, you're hard as a rock.

"Hold on a sec there, Missy" you reply. "You know that age is simply how you feel," you tell her as you grab her hand off of the table. Her cheeks blush almost as red as her hair. "...or how others make you feel."

"You sure about that?" she tentatively asks.

"Of course, " you tell her. "I think you're pretty hot myself. Total MILF."

"MILF? Where have I heard that before?" she ponders. "What does that stand for again?"

"Mom I'd Like to...." you lead.

"Fuck?" she asks. You nod in response. Her usual confidence returns and slyly cocks an eyebrow at you. "Well, if you want that, you're going to have to work for it."

"Good things are only earned with hard work," you reply. You feel something playing up your leg. You realize that she's snaking her foot up your leg towards the tent in your jeans.

"Well, how 'bout you come back to my place and start putting in some overtime?" she coyly asks.