I've had a few hot bosses. The first one was a store manager and he had a nice bulge and he was well aware I looked every time I saw him. He would often become erect so I could get a good VPL. But it was always unspoken. The closest we came to speaking or making any advancements was one time we were discussing what we did on New Year's and I said, "Nothing. I don't do anything." And he walked up next to me and placed his bulge on top of the chair I was standing behind where I was resting my hand and said, "I know you like to get down and party." But other coworkers were in the room so I couldn't exactly rub it. Although there was another time where we were peeing next to each other and when he was done, he turned towards me with his zipper down and then zipped it up. Not sure if that was a move but who zips up not facing the urinal?
Another store manager I flat out told him he was the hottest guy in the store and he had an amazing ass. But his ass was an open topic to everyone as he liked showing it off. He wore extremely tight pants to do so. Even stated he worked hard to make his ass as great as it was. He openly admitted to having a small penis too. As was obvious as there wasn't even a mosquito bite from the tight pants he wore. A department manager at the same job was also hot and I told him we should have sex many times but I believe he thinks I was joking from how bluntly I would say things like that. I would even tell other coworkers I gave him a blowjob while he was standing there and he never denied it. (It unfortunately wasn't true.)
An assistant store manager at another job I had I think was turned on by my bulge as I caught him sneaking a peek a few times. And one time he offered me a ride to work on his day off and he picked me up while wearing pajama pants. I turned over and it looked like he had a full erection. To this day I regret not asking.
Not to mention all the coworkers I've flirted with at all of these jobs. I say it all depends on how important your job is to you. Two of the three jobs I listed here aren't in business anymore so it wouldn't have mattered whether I made stronger advancements or not. My current job I like and don't plan on losing so I haven't flirted with anyone. The closest I came to was a coworker explained a situation and his stance on it and asked, "You feel me?" and I replied, "Not yet, I haven't." I really feel like you should get a feel on situation first. Read the room as carefully as possible. If your gut tells you that you can randomly suggest sucking his dick then I say go for it. If you're close enough friends, you could probably play it off as a joke. Like if he ever asks you what you're doing after work you could say, "I don't know. I'll probably suck your dick or something." His reaction to that will tell you all you need to know. A coworker I suggested this to replied, "We'll keep that a possibility." And we both wanted it, he even rubbed his penis on me, but we never did because our bosses would micromanage us and we had too much work to do so go off and do that.