You might want to start a bit slower. Play with her area first... try fingers, a butt plug, a dildo, or anal beads. Yes, use lots of lube.
I've attempted this many times and when it finally "clicked" and worked for me was after getting more comfortable with the feel of it inside and let HER lead. Don't just shove it in. Let her be the one to guide and communicate. If she says go further, let her slide on it. If she says stop, then stop, but don't immediately pull out because doing it too fast could hurt her even more.
Also, try different positions. Her on top, spooning, doggy, whatever. If she's really wanting the anal and you want it, too...just be patient and experiment enough so she's more comfortable with it.
But it feels good. =x
Your all trying too hard. Just get her a little drunk.
my girl hated it cause my dick is so huge
ripped that bitch open
Would not recommend this, ever.It's like ripping off a band-aid. Gotta get it it over with and in as quick as possible.
Lube, fingers. Take it slow over a long period of time til she's ready.
Man, why is it that everyone on the internet has a big dick
anal is for faggots