Anal is pretty central to my (32M) play, and I figure I have some stories you heathens might enjoy reading, so here goes.
A few years ago I had started seeing someone off Tinder who I learned early on was interested in exploring ass play. I'm a pretty direct communicator, so I'm usually more than happy to have a conversation about kinks, fetishes, etc., right at the start of a new connection. She said she had tried a bit of ass play and really enjoyed it but she had never built up to full anal sex with anyone. I shared that ass play and anal sex are my biggest turn-ons and that I'd be happy to build her up to her first anal experience (and many more).

Over the course of the first couple of months of our connection, we did a bit more each time, and every step was a joy. She had a pretite build with straight hair all the way down to the small of her back. I'm quite tall on the other hand, so a good bit of contrast in our body types. She had a cute little butt and when I would bend her over to spread her cheeks, my hands would cover almost the entirety of her cheeks.

We started rimming and some very light fingering. I love eating ass for its own sake, but a big plus here was how thoroughly turned on she was by it. Every time I'd slip my tongue in, she'd moan or let out a whispered "fuck." When I'd put a thumb in her ass while fucking her from behind, she'd almost melt into the mattress.

I remember once, just before cumming, I pulled out, pressed the tip of my cock against her asshole, and unloaded between her cheeks. I asked her how she felt about that afterwards, and to my surprise she said she learned that's her favorite way for a guy to cum - up until then, her preference was for facials. I, of course, had some idea of somewhere I could cum that she'd love even more.

We went out of town together for Halloween weekend and stayed at a fairly nondescript AirBnb. For a couple of months, I hand been centering our foreplay around anal - rimming, fingering, and then a steadily bigger range of plugs - so I brought all my toys with me on the trip. After a fun night out and a silly costume contest (in which I placed third, mind you), we went back to the AirBnB and got down to business.

I had her on her knees on the floor next to the bed with her chest on the mattress. I asked her to reach back and spread her cheeks for me. There's something about seeing a partner do that for me that's just exceptionally hot - a physical invitation to do the things I enjoy most, I guess. Rather then get started right away, though, I brought my lips to her left ear, whispered "good girl," gave her earlobe a little bite before kissing down the side of her neck, over her shoulder, and down her spine to her ass. After a moment's pause to let the anticipation seep in, I brought my tongue to her ass.

Between rounds of rolling the tip of my tongue around her asshole and licking across it, I'd slide my tongue in - each time pushing a little deeper. I could tell by her breathing that she was really, really into it. I sat back for a second and asked her if she liked how I fuck her ass with my tongue. All she could manage was a breathy "yes" before I brought one hand to her pussy and another to her ass. With my right hand, I started rubbing her clit, and with my left hand I slipped my tongue into her ass and started to slowly slide it in and out. She, despite the intensity of what she was feeling, followed instructions and kept her cheeks spread nice and wide for me.

Wanting to be a bit more involved in the fun, I took one of my smaller plugs and slipped it into her ass. After seeing her cute little hole tighten back up once she got past the flared base, I put a bit of lube on my cock and started to caress her labia with the tip. It seems she may have been out of patience by this point because she rolled her hips back to take me in. But I was focused on building up, so every so often I'd stop and ask her if she felt ready for a bigger plug. Each time she enthusiastically said yes. And each time, I watch her ass slowly let go of one plug then readily take in a bigger one. After three or four iterations, I stopped and said "I think you're ready for my cock - do you want to try?" and again her enthusiasm was unfaltering.

I pulled the last plug out and put a healthy amount of lube on my cock. This time, without instruction, she reached back and spread her cheeks for me. I wanted to savor the moment a bit longer so I rested the shaft of my cock between her cheeks and started grinding up on her. With each thrust I could feel the little ridges of her asshole as I moved back and forth, and with each thrust I shifted my angle a little and applied a bit more pressure before grinding again. A handful of thrusts later, I stopped the tip of my cock against her ass and started to slowly build pressure. Before long, I could feel her starting to stretch out, and I could feel myself starting to slip in. With a series of "oh my God"s and "oh fuck"s from her, I felt the tip of my cock slide in then the rest of my shaft ever so slowly until I was as deep in her as I could get.

Pausing for a moment, I leaned forward and asked "how are we doing?" and received a whispered "good" in response. So I grabbed hold of her waist and slowly pulled back before beginning with a gentle pace. She felt amazing. As I steadily picked up the pace and depth, she had one hand clutching the sheets and the other between her legs to play with her clit. I moved my hands to her cheeks to spread them for a better view of my cock finally fucking this sweet, filthy-minded, delicate little thing in her tight little ass. When I heard her breath catch the way I know it does when she starts cumming, I knew I could let myself go. With one hand on her ass and the other pulling her hair, I switched to a strong, deep, and consistent pounding right until the last moment before I pushed as deep as I could and collapsed on top of her - my breath on her ear, my hips keeping slow little pulses going as I came in her ass for the very first time.

Safe to say that was her favorite way to make a guy cum after that.