I'd had anal sex before (with a girlfriend who found vaginal intercourse uncomfortable and actually preferred anal), but it was another girlfriend's anal initiation that really stands out in my memory. I would often finger her asshole as I ate her out or when we fucked. She always seemed to dig it, but I was still surprised how readily she agreed when I suggested we give anal a try. She grabbed some moisturizing lotion to use as lube (which I guess isn't recommended, but we didn't know any better, and no harm seems to have come of it). I began to go down on her -- thinking an orgasm might relax her and make the next part easier -- but she was excited to get to it. She slurped at my dick, finding me rock hard already -- I was excited to get to it, too -- then turned away, presenting her ass.

I lubed her hole with lotion, dipped a finger in, then two, nothing new for us. Then I smoothed some lotion onto my cock and placed the head at her asshole. Leaning into her gently, I slid in with ease. She gasped as my cock stretched her, not a gasp of pain but of pleasure. I withdrew slightly, then slowly slid all the way into her. "Oh my god," she breathed, pushing herself back onto me. We had started with her on hands and knees, me kneeling behind, but gradually wound up with us both kneeling upright and pumping together. I reached around and squeezed her breasts with one hand.

Her nipples were harder than I'd ever felt them. With my other hand I reached down to play with her pussy. I couldn't believe how stimulated she was. Her clit was engorged beyond anything I'd seen before, sticking out like a tiny penis. I dipped my fingers into her sopping slit and stroked her rock-hard clit between a slippery thumb and finger, jacking it off like a little cock as I pumped in and out of her ass. She had always been the most orgasmic sex partner of my experience, but I'd never felt her cum before quite as powerfully as she did then, and we came together, me shooting off deep inside as her sphincter muscle spasmed around my cock.

Collapsing to the bed, breathless, we remained spooned together as I slowly melted inside her. She said she felt incredibly full with my cock up her ass and enjoyed her first time so much she suggested anal again when next we got together. Sadly the repeat performance wasn't anywhere near as magical for either of us. We never tried anal again after that and broke up before long (for other reasons), but I still remember my ex's anal initiation as the #1 highlight of my sex life.