Author: Mango4211

[MF] My first time with an older woman at work pt.2 (based on a true story)

See pt. 1 for context

After we got cleaned up a little bit, we went into the restaurant. She reapplied her lipstick and handed me some napkins before we walked in to make it less obvious she had just sucked the life out of me and made me squirm five minutes earlier.

I was still in shock at how quickly our first encounter had happened. There was still a great deal of tension between us because I was pretty embarrassed and I don’t think either of us had anticipated this whole hookup actually happening despite us both wanting it to.

Surprisingly, dinner was totally normal for what two coworkers on a business trip. We even ran into a couple other coworkers which made me incredibly nervous. I didn’t know how obvious it may have been, but to this date I have never had any reason to believe any coworkers had a suspicion, to which I attribute our age difference.

After dinner we walked straight over across the parking lot to the hotel. Knowing we had coworkers staying at the hotel, we both checked into our own rooms like normal. As we walked to the elevator she looked around to make sure nobody was around and told me quietly Read more »

My first time with an older woman at work [M/F] (based on a true story) Pt.1

Right out of college at age 22, about 5 years ago, I started work, not a boring 9-5 desk job, but corporate nonetheless. I was put through a training program to learn how to do the job, and in order to graduate from the program, I had to have once a month check ins with the hiring manager.

Her name was Cindy, she was laid back, professional, very personable, and had the mom next door vibe. She was in her early 40s, had a couple kids at home, and was going through a divorce. She mostly worked from home, so we really only saw her when we had scheduled meetings.

Something about her though caught my eye. Her voice was sultry and kind, she dressed in unassuming work clothing, but you could tell even at 40, she still had it. Her wavy brown hair and bright red lipstick always caught my eye.

Our first couple meetings were straightforward, we would work for a few hours in the morning, go grab some lunch, then go back to review at the office. We got to know each other pretty well at these lunches. Both professionally and personally. I found out all about her divorce and frustrations with that. Read more »