***if you can’t tell the title is a joke ***
I was a first year teacher, just turned 22. My evaluator was a late 40s slim Greek trophy wife looking type of woman. She had a perfect ass and fake tits. Not huge but perky enough to know they weren’t real. She stood maybe 5’2” in heels. For someone who’s 6’+ and then some she was my work fantasy. To make it worse she was my evaluator. The first time she came into my classroom i wasn’t expecting it, it was an informal observation. She caught me off guard. I could feel myself getting aroused, I immediately went behind my podium to finish my lesson. I got a terrible rating, being told I should facilitate more discussion.
The next time she came in was another informal, again off guard and I could feel myself beginning to bulge. But fuck it if I wanted my job I needed to continue. As I walked by her I saw her catch a glimpse. When we met for the debrief I thought she’d mention something but instead just gave me a glowing review then mentioned I might want looser fitting pants.
That Friday our crew went out for drinks, we sit at the edge of the bar, i got their early and I sat on the corner with my back up against the back wall of the bar in the corner seat. She walks in with the crew and positions up next to me. She ends up buying my first drink and a shot to celebrate and apologize for her comment. We do another shot, and she’s a light weight. She begins telling me all her martial problems, placing her hand on my thigh feeling my bulge. By then end of the night she was riding me in the back of her Cadillac Escalade.
Source: reddit.com/r/sexystories/comments/vgpu97/what_do_you_do_when_your_boss_is_also_in_charge