I have this problem where almost anyone can tell me to get naked or take my dick out and I get so turned on by it that I feel like I have to. I’ve done it quite a lot for strangers online but I’ve also had a few experiences doing it in person.
One experience I’ve had was actually with an older female coworker. At the time I was 22 and she was about 40. She has a very pretty face and was a bit on the heavier side. While we worked together, we always had a flirty relationship but we never went any further than just some harmless flirting. I am a remote worker that works out of state from my office and so was she so most of the interactions I had with her were over IM or email. She would often message me after we had a video call for work and compliment me with things like, “Nice job on that meeting, handsome”. She would also send a lot of flirty emojis along with these messages. But it was always just flirting and nothing more.