Just confront them. If you're in a place in your relationship where you're comfortable, ask them how they feel about fetishes. Gauge reaction. Then, suggest the fetish and provoke them to voice how they feel about it without suggesting it's your fetish. Go from there based on how they react. You might need to be a little smooth with your language but thats how id do it.

>>17226714
So a bit like the whole "my friend has this problem" thing? I hope its not too transparent...

When he mentions anal you're supposed to say "you first." If he's not outraged, that's a maybe.

What are your fetishes OP??

>>17226917
Well, besides those two and off the top of my head:
>shibari
>rape
>golden shower
>chikan
>humiliation
>intercrural sex
>femdom
I consider myself pretty vanilla.

I might just be lucky and got myself a bf that's not inherently against those fetishes, but i slowly worked my way up by gently introducing assplay. so far we are at a point where i fuck his ass with a vibrator. I think it won't be long till i'm pegging him.
For feminisation, i was just always joking around with him and he wasn't put off by it. He's really into panties so i made him slip into mines. I'm not entirely sure how far i want to go with that, but i find the idea of him in girly stuff pretty arousing. I'd say, just take baby steps and let him get comfortable with something before going any further. I'm sure you can get far with that. I also think it's better than just outright ask him, cause the tought of getting pegged might be too overwhelming if you are not yet getting your ass fucked with a vibrator regularly. Sure, i won't just pull out my belt and start fucking him without warning - dear god... But i'm slowly broadening his mindset so he's ready when i ask him.

Make him take a shower before so that way he's not alarmed about being unclean or worried about anything.


Then blow him shortly after he gets out, while trying to slide a finger in his asshole.

He might protest, but tell him to trust you, or you wont finish the blowjob.

Then when he's getting close, stop all attention on his penis, work that asshole good, and let him nut all over your tits without stimulating his penis one bit.

I think you'll be able to work him into getting pegged after enough anal play.