Initiating anal

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Hi all - so my boyfriend and I moved in together a couple months ago, and we just haven’t had anal sex as much as I would like. I’ve spoken to him about it, and he wants it more frequently too. However, he (who always tops) never feels like he can initiate it, since he doesn’t know if I’m “ready” for sex, and doesn’t want to embarrass/pressure me. That puts the onus on me to always initiate. I understand why he doesn’t want to be the one to ask, but I also don’t want the pressure of always being the one to initiate sex. It also feels weird to just call him into the bedroom with a dildo in my ass and ask him to replace it with his dick. So my question is, does anyone have any suggestions on how to more evenly split the initiating? Or how to initiate in a more sexy way?
 
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My go to with guys is usually if I’m sucking their cock I try to play with their hole too. If they deny that then I know its a no go but if they allow it, I move to rimming. If they allow that, then it just shows they’re ready for it. I know when I’m not feeling up to it, I dont let anyone near my ass.

I would also just say that he should just go for it more often. He should be confortable enough at this point to make that judgement. I would just talk to him about signals and signs for when you are and aren’t ready. Communication is key.
 
We are both versatile and have been for 20 years. I honestly don’t clean out before sex. Of course I’m freshly showered but that’s typically good enough. Occasionally he might get a little on his cock but it’s not the end of the world. The fact that we’ve been together for years may help.
I have serious tummy issues and mal-digestion so sometimes I have a day of diarrhea and am not fit to bottom because my ass is sore and irritated and it could get messy. On these days I just make sure to tell him that I’ve been “sitting” a lot which is our euphemism for, I’m shitting my guts out and can’t bottom.
If he wants to bottom it gives him a heads up but honestly it’s not a necessity if you have a good diet. Typically there’s nothing but lube and cum on our dicks when we pull them out.
My first partner, who taught me how to be versatile, used to say if you make mud pies you might get muddy!! Lol
Have fun and don’t stress. If you want to play send him a playful text saying you’re looking forward to some snuggling tonight. He’ll get the hint.
 
Great advice frim the others posters.

Also, getting frisky doesn't always have to be anal. Your guy could still initiate whenever he wants to and if you feel you're not ready to bottom then you can engage in other fun activities.

When I find myself in such scenarios where I'm not 100% sure I usually just make an excuse that i need to pee before we get hot and heavy. Go to the loo, slide a finger up your ass as far as you can and give yourself a good feel. If all comes out clean and good, then it gives me the peace of mind to relax and enjoy it without worrying too much.

Lastly, like already mentioned here, it's not always sunshine & daisies when it comes to anal sex. If there's a little bit of "something" , it's really not the end of the world.
 
My go to with guys is usually if I’m sucking their cock I try to play with their hole too. If they deny that then I know its a no go but if they allow it, I move to rimming. If they allow that, then it just shows they’re ready for it. I know when I’m not feeling up to it, I dont let anyone near my ass.

I would also just say that he should just go for it more often. He should be confortable enough at this point to make that judgement. I would just talk to him about signals and signs for when you are and aren’t ready. Communication is key.
Just saw your cock and I’d never turn down a fuck from you!
 
Hi all - so my boyfriend and I moved in together a couple months ago, and we just haven’t had anal sex as much as I would like. I’ve spoken to him about it, and he wants it more frequently too. However, he (who always tops) never feels like he can initiate it, since he doesn’t know if I’m “ready” for sex, and doesn’t want to embarrass/pressure me. That puts the onus on me to always initiate. I understand why he doesn’t want to be the one to ask, but I also don’t want the pressure of always being the one to initiate sex. It also feels weird to just call him into the bedroom with a dildo in my ass and ask him to replace it with his dick. So my question is, does anyone have any suggestions on how to more evenly split the initiating? Or how to initiate in a more sexy way?
I just grab the guys cock and tell him I'm hungry for his cum by the time I've given him head and not stopped till he's hard again