When asking me (a cis gay male) about sex; here are some of the Don'ts if you still want me to think you're Educated.
Never ask flat out, within the first five questions, “So are you a Top or a Bottom?” This is something that I will most likely share on my own, and if I don't; please don't fucking ask. Think of it this way, for me it makes me feel like you've questioned my masculinity and think you know the answer... which by the way I even find it offensive if someone asks me the same question on Grindr within three speech bubbles.
“Does it hurt?” or “Is it messy?” - Yes to both, but no if it's done right. See, anyone who uses their asshole as an orifice is usually smart enough to know that there is going to be shit, the smart ones usually 'clean' it out before engaging in anal sex and know what happens if they don't. But no matter your taste, duh it hurts! Unless you have the right amount of lube, and maybe poppers. Every time I am asked this question, I first laugh then ask; “Well have you shoved more than three fingers in your ass?” followed by, “How quickly did it take for it to feel good?” finally, “How much shit did you have under your nails?”. Just know this, ass play is usually going to get a bit shitty (pain wise or, actually) so just leave the topic alone! Unless, you are asking because you want to try it then usually anyone who's done that 'deed', will share some tips... just make sure that they have done it more than four times so you'll get solid advice.
Stop, please just stop asking me what ‘I'm into’. The only way you should ask me what I'm into is because you're about to show me a photo of your hot friend that you want to hook me up with, and have done enough research to know if it'll be a one time thing or BF shit, thanks.
Also I faced enough discrimination in my life for being gay, but then asking me, “So, you're a twink right?” is such a basic description of a person and because of my body type, means that yes I would then be considered a twink, but just because you've put on a few pounds doesn't mean I then consider you a Bear, right? Cool, because then again, who would want a pole dancing, Vers, Femme Identifying, Hair Stylist who likes to stay active; when they can have a twink instead.
Heck, if you want to ask me questions about why I'm gay or even how I knew I was, please lets chat; because that uses brain power to think of how to explain myself and articulate it... rather than what stereotypes I have 'subscribed' to.
Don't ask me if I'm a power bottom, because you don't have to know how much or little of a freak I am. A “Man” is only so lucky to know how I play it in the bedroom, so why the hell would I let you know something so intimate? Should I ask you if you how hungry you are when you get some? Jeez, can't I keep my “Freak in the sheets, Lady in the streets” thing going? I feel like it's only talked within a conversation with my sexual partner leading up to the deed, and after who's been coined the bottom for that round.
Another thing that I feel too many people ask me is, “Do you like, use Grindr?” Yes, yes I do, but no I don't like it because I never get what I want, it's like a meat market that I can't touch. And if you're asking to see it, just ask to see it... just don't start any convo's with anyone because then you're most likely going to see something that I would rather you not. Let me show you the dirty pictures, please.
All in all, I am a pretty straight forward person who is willing to share with you as much as I am comfortable with, just don't go right for the gold without prefacing the conversation first with a tone that would warrant that level of intimacy and have enough smarts to know that gay sex is very, very varied so sometimes it might not be the best conversation to get into unless you want to genuinely know more about it and have enough respect for the people you’re exploring those conversations with.