I've been sharing some stories with people I've chatted with via other subreddits, and decided I wanted to share them with a broader audience. So here you go.
So, my first time at a gloryhole was with my then-BF my senior year of college. We already had a pretty elaborate sex life, so there weren't many obstacles to us being honest about our fantasies.
One night, during a "what haven't you done with a partner that you want to" discussion, he mentioned that he's always wanted to take a girlfriend to a gloryhole and watch her work. I explained that I was MORE than okay with that, and told him that if he did the legwork on finding a place, that'd I'd do it.
It took him a couple weeks, but he found an adult bookstore with the booths in the back. I dolled up for the occasion, with a plunge neckline showing a quite significant amount of cleavage, a moderate-but-not-extreme short skirt, fishnets, and my go-to slutty dark red lipstick.