32 [M4A] Drinks With The Former Boss & Her Wine Fueled Revelation Leads to Fun

She used to be my boss, 36, blonde, sharp, disciplined, decent milf that liked her skirts, but the kind of woman who kept her hair tight and her reputation tighter. For two years, I (Luke, 28 then) worked directly under her, she was tough, demanding, and never gave an inch. But behind all that control, there were always the looks. The subtle pauses during meetings, the way her eyes would linger a beat too long below my belt before flicking back to her notes like nothing happened.

I moved on a year ago to lead my own team. We barely spoke after that, just the occasional message, professional catch-up, until she invited me to lunch to talk about some project crossover. It was all business at first, but in between work talk she let it slip: she was separated. Early stages of a divorce. Her voice was casual, but her eyes watched me carefully.

That evening she suggested drinks, just to keep the conversation going. We met at the bar down the block from the office. A couple rounds in, she mentioned she wasn’t in Mom mode, since they were with their Dad for the night. Then she said it again. And again. By the fourth time, it wasn’t a hint, it was a challenge.

So I leaned in and said what we’d both known for years: “You’ve been eyeing my bulge since my second week on the job. Maybe tonight, you finally find out the answer you’ve been looking for.”

Want to know how it went from here or talk about a similar situation you were in, reach out and say something.

I’m Luke, 32M, 6’3”, humble and creative, bwc, strong arms and chest, six pack having, experienced bull. Let’s have a filthy chat and start with your age. 19+ only