Author: dirtybossforyou

These days, I have a lot to lose. I have a marriage that is not fulfilling, but would be very expensive to end. I have a job where character issues mean unemployment. I have people relying on me to disappoint.

But I still have needs I need to feed, so I end up in places like this looking for like-minded people who need to get off.

Lori was 18 and a half when I met her online. I laughed when she told me how old she was because she was still young enough to add “a half.” I had posted a fairly mild ISO-type post that I had some success with, but none of those connections quite scratched my itch.

Within 15 minutes, Lori called me Sir without asking. I knew she was special.

She provided verification photos proving her age and her description of herself were accurate. She was a petite college freshman–barely 5 feet and 100 pounds–with a pretty, but not beautiful face. She was biracial–white and Asian–which gave her some interesting facial features. She told me from the beginning that she would not send any pictures that could come back to haunt her later, but I found myself rubbing myself through my pants all the same as she sent me her suggestive, but tasteful selfies. Read more »

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 peak 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 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 »

Ally was my niece through a former marriage. She stopped by my place last month before heading back to college for her junior year. I thought she just wanted to say a quick goodbye since we had gone to a couple of baseball games together over the summer, so I didn’t hestiate to let her in even though I had a friend I made the night before still sleeping in my bed.

Ally walked by the door to my bedroom and saw the young woman’s bare back and her pile of clothes on the floor next to the bed. She raised her eyebrows as she walked over to the couch. “Based on her style, she’s a little young for you, Uncle Roger.”

I tried a sheepish grin. “Ah, I don’t think so. She’s getting ready to head back to college herself–it’s nothing serious.”

“I didn’t realize you liked girls who were so much younger.”

I really didn’t feel comfortable discussing my sexual interests, so I tried to change the subject. We talked a little about Ally’s upcoming semester. Read more »