It's been about 10 years since I sucked a guys cock and I really want to do it again. There's this tall good looking guy that's always at the casino where I gamble and we usually gamble together on Friday nights. I think he may have swung the other way once or twice but I'm really not sure. He's also a little on the female side which makes him adorable. I would love to suck his cock but don't know how to approach him about this. Any suggestions.
Propose a wager on something with his prize if he wins, your oral skills. Something like that can be put out there as a joke and avoids awkwardness if he’s not interested
Here's what I would say..."Not that it matters to me but have you ever been with another man sexually?" If his answer is no reply with "Ever consider it?"...I did this once and his second reply was "Are you hitting on me?" to which I replied "Yes I am if you'd be interested in a blow job"...30 minutes later I was on my knees sucking his cock.
