Author: thedirtyboss

Smells Like Middle-Aged Desperation [MF, light age-based humiliation, oral]

I’m in charge of a business function that covers several different offices, so I’m often on the road to visit the locations. I kept hearing the name of a new salesperson come up: Linda Marconi. Some of my staff at the office she worked at were becoming very involved with problems she should have been calling into a service desk for. I asked them to redirect her, but then I would hear from other employees that they continued to help her.

I was a little puzzled–these guys usually tried to avoid dealing with people as much as possible. So on my next visit, I kept one eye out to see if Linda would stop by the area where my team was assigned. By noon on my first day there, the question had been answered.

The clicking heels announced her presence and I looked up subtly to see a nice pair of legs. She was wearing a skirt that was too short for an office and four-inch heels. I already had a feeling about what her deal was before she turned to peek into my office. Once I saw the tell-tale overuse of eye makeup and low cut shirt, I knew she was experiencing what I call the “aging stewardess syndrome”: an aging woman who relied on her looks for professional success and was not dealing with her decline very well. I didn’t give away that I had checked her out and continued to work. Read more »

Rear Entry [Str8, Mf, creep, masturbation, anal, oral]

Mark was annoyed when he got the rear door of the McNair’s house. They were good neighbors and had helped him out in the past, but he didn’t want to have keep walking over here to check for Sam’s “important letter.” He shared a backyard property line with them and had to cross some brush that inevitably scratched his hands every fucking time. But Sam said this letter had some information he really needed while he and his wife were on vacation.

He found the magnetic key box hidden under the small back porch and unlocked the door. He walked through the kitchen and living room to check the mail on the floor under the mail slot. He picked up and sorted the mail. No letter. He put the pile on a small table next to the stairs with the rest of the mail he’d picked up the last 3 days.

It was cool and drizzly outside, so he was in no hurry to get back home. Besides Margie was on the rag and being really nasty today. Maybe he’d hang out here for a bit and watch one of the college games. Sam had a much better TV anyway. Read more »

Asian Take-Out [Str8] [Mf] [cheating]

I’m a creature of habit, until I’m not. Left to my own whims, I’ll stick to a well-worn path of choices with predictable results. When I’m pushed in another direction, I find I really enjoy it once I get past the initial resistances. Yet for whatever reason I have difficulty in moving myself away from my norms.

Gretta, known as Gigi, was based in my company’s Manila office. Gigi and I had worked together for a few years before we met in-person. We had a great rapport and even engaged in some playful flirting while we had calls, which wasn’t unusual with the single women from that office. I always enjoyed their schoolgirl-like giggles when they first heard my deep voice.

The events in this story took place during the tail-end of the years of being able to know someone without being able to find them easily through social media. So, I’d have pictures in my mind of these Filipino girls I spoke with–eager, lithe, and just out of college–but I didn’t know what they actually looked like. Read more »