I've been tryin to get my girl to take it in the ass for quite awhile now. She had never tried it before nor had I, so I kinda figured ya know just lube her starfish up nice and good and go for the gold. I also wore a condom which I usually don't do, but I mean idk I don't want shit on my dick? Anywho first time we go for it we're both pretty drunk and my dick is big enough to where it hurt her. Like a lot. She was crying by the time I got ~1/2 in and then slipped in further really quickly. It clearly wasn't happening, and now she's hurting and I'm still hard wanting to get off so I end up pretty much jerking off on her tits. Lame.
At this point we realized that this was no ordinary thing, that it would take preparation (H?). So I guess she does research and comes across this video.
Useful advice from a cute girl on buttsex? PERFECT! So I take her advice and start throwin a finger in her butt while fucking to get her used to it. I have to admit, i was nervous that my finger would smell like butthole. But after the first go round with ol fingerbutt it was good, she liked it, my finger did not smell, I was overall pretty psyched.
A little too excited? Next go we're both again kinda drunk, and I overplayed my cards and went for 2 fingers in le poop hole. She's holding back tears but wants me to keep going, which I'm reluctant to do obviously. But she tries to jam my fingers in there real good, and just can't hold it in anymore and stops. Bummer man.
I am definitely discouraged, haven't even gone for the finger again and idk if it'll ever happen (at least with her). I guess I technically had buttsex once tho? Oh well. She licked my butthole once and it tickled and I didn't dislike it.