I hate condoms, and thankfully am in a happy monogomous marriage, and can always be condom free!
We never use em for anal either...I'd never come if we did, and frankly as long as the receiver has gone to the bathroom in the last couple hours, it shouldn't really be 'messy' like how you're afraid it will be.
Still, put a towel down, because you'll use massive amounts of lube and that'll gum up, or stain the sheets depending on what you use.
I'd start with a finger, or a smooth, small plug about 1/2" in diameter. Once you get used to allowing something to be shoved up your butt, its easier to relax so that larger things can be inserted.
Lots of lube, take it slow, and if she's feeling actual pain (not just mild discomfort) then you should slow down and re-lube, or simply stop for the session. It may take a couple of attempts.
For the record, my wife can come from anal only, and will come again if I blow my load inside her ass...mainly because the swelling that occurs prior to orgasm drives her over the edge.
We never use em for anal either...I'd never come if we did, and frankly as long as the receiver has gone to the bathroom in the last couple hours, it shouldn't really be 'messy' like how you're afraid it will be.
Still, put a towel down, because you'll use massive amounts of lube and that'll gum up, or stain the sheets depending on what you use.
I'd start with a finger, or a smooth, small plug about 1/2" in diameter. Once you get used to allowing something to be shoved up your butt, its easier to relax so that larger things can be inserted.
Lots of lube, take it slow, and if she's feeling actual pain (not just mild discomfort) then you should slow down and re-lube, or simply stop for the session. It may take a couple of attempts.
For the record, my wife can come from anal only, and will come again if I blow my load inside her ass...mainly because the swelling that occurs prior to orgasm drives her over the edge.
Good luck! Tell her it will be so worth it. 