Hello, I've been on a stag week. What did I miss?
Oh, hello!
If we're talking as deep as possible rather than just a bit of a rim, I've done this to one girl. I referred to her as "Lizzy" in a previous post. She was the girl I lost my virginity to and even though she had had sexual experiences before me, there were quite a few things she hadn't done, including much in the world of bum play. She said it seemed weird to her. Anyhoo, one day I was giving her a massage and rubbing her back and bottom which she liked, and I found myself planting kisses on the backs of her thighs. As ever she was getting a little wound up and I was holding her cheeks apart to have a good look at her aroused pussy, and without even thinking about it I ran the flat of my tongue over her exposed asshole. She giggled, but didn't tell me not too, so suddenly I was rimming her, and eventually putting my tongue as far up as possible while she squirmed and moaned. Afterwards I asked her "you liked that didn't you, you dirty bitch?" and she just blushed in silence unable to deny it. Better still was one night we were staying in a hotel in York when I brought her to climax with her bent over with my tongue up her arse and my fingers on her clit, then she turned over and spread her legs wide and put her hands in my hair so I could eat her cunt to a second orgasm. Then she dragged me on top and made me take her like an ******.
Well, you did ask.