My current girlfriend is extremely shy about her bottom. The first time I licked her bottom hole she described it as ticklish but I could tell she was not totally ok discussing it. After a while she admitted she had “a bit of a complex” about that part of her body and said she wasn’t comfortable when I licked or touched her “back there” so I obliged. But she does love caresses and kisses on her bottom cheeks.
However without hesitation she will play with my bottom, whether it’s just massage and touching, slowly prepping my anus then taking my temperature rectally, caressing the outside of my hole while sucking my cock, or fingerfucking me deeply as I bend over for her. For a long time though she never brought her mouth near my bottom. I didn’t ask because I thought it would make her upset.
It’s not too frequent, but yes rimming does happen in our bedroom. The only time we do it is after we’ve had a good few drinks after a night out. She still remains quiet but becomes more sexually aggressive and naughty as we have sex. Eventually I’ll feel her hands on my cheeks, which is the moment when I stop whatever I’m doing and let her take the lead. Usually I will let her turn me facedown or sometimes she’ll position us in 69 with her on the bottom. Either way she will caress my ass cheeks, very slowly moving her fingers inward, driving me crazy with anticipation. Eventually I will feel her fingertips touch around my anus before finally teasing the hole itself. The next sensation is her gentle but strong hands spreading my cheeks wide open and then her warm wet tongue on my needy little anus. This is the only time she ever talks, she feels the need to ask “Do you like that?”
The sensation is usually too intense for me to last long, so I will turn us over so I’m on the bottom, before I cum too early. In that position she will relax as I kiss and lick her now soaking wet pussy, and I’ll spend time to bring her to at least one orgasm because I’m worthless once I ejaculate. Her on top facing away also affords me the glorious view of her beautiful ass and soft tight tiny bumhole. So just to be sure it’s ok, I’ll touch around and across her anus with a finger and if I hear her very subtle moaning begin then I know it’s ok. At that point after looking at and playing with her beautiful little pink and purple and brown opening some more, I’ll lean forward and gently place the tip of my tongue in the center of it, then slowly begin exploring it.
Though she does not enjoy rimming when sober and never wants to talk about it, in our semi-drunk state she adores it. The more my tongue and lips move around that most private area of her body, the more she moans and squirms, but never moves her bottom away from my mouth. Her usual reaction is to eventually start stroking me and sucking my cock and often this is how I will orgasm, cumming in her mouth with her asshole gripping the tip of my tongue.
But still we have never, ever talked about this very naughty thing we sometimes do to each other.