>>17146193
>Sharpie in pooper

Nice setup.

I have regular anal sex with my bf and sometimes it's really amazing and other times it's too painfull. What makes the difference is small stuff like how relaxed and horny i am. I usually like it best if we start with oral, then proceed to PiV sex and then when we are both already really worked up, bf proceeds to play with my ass. We also use loads of lube and then the trick is to not go too slow when entering. That's the part that might be pretty painfull. It sounds weird, but it's better tolerable when he's balls deep inside you. While he is entering you, BREATH. Seriously. It keeps you relaxed. And try to keep your jaw soft. Don't clench. It helps to not tense up, which leads to pain. Make sure he has been almost at the point of no return before you started so he will only need a few minutes of anal to cum buckets. Prepare for anal leakage and bloating after... It works like an enema.

Thanks, was just going to try and get my gf into anal tonight.

Explore your anus on your own to understand the realities of sticking things up there and what is pleasurable and what isn't. Then you won't be an anus virgin and you'll have some experience as to what will work and what won't. Then you can introduce him as someone who you hopefully trust enough during sex to listen to your feedback during the act itself.

With my current gf who'd never done anything like that before I introduced the idea and encouraged her to explore it herself. She wasn't actually interested at all until I brought it up and she still didn't seem that interested until I hinted that I'd be interested in checking her progress. Then it somehow became some sort of 'ass training' game for her mixed up with some sort of mild teacher/student fantasy play where I'd eventually fuck her ass when I decided she'd done enough to have a practical exam. Not really my bag, I'd rather she wanted her ass fucked for the pleasure of having her ass fucked itself, but then anal sex connects up lots of different kinky feelings and ideas for different people and whatever, I got to fuck her ass and she got to squirt all over the place. Felt good to be gangster for a while I guess.

>>17146224
i might be one of few girls that actually enjoy anal. but it's stil mostly painfull, so make sure you are not holding back but cum when you are ready. iow, don't try to artificially prolong the act

>>17146193
Why do you want anal sex? To please him? That's not a good answer. Because something tells you that you would find it physically or psychologically pleasurable? Then begin with some experimenting on your own. See what it feels like to have your hole tickled,or to have a finger in it. If neither of those experiences does anything for you, forget it. If you do like the feeling, then suggest he begin with fingers (and lube), to see how you like having him do it. If and only if everything is pleasurable, you can then try more. But if at any point it isn't fun, give up because it's only going to get worse.