He took it so well
I hadn't topped in years because it was dysphoric, but I want to give this (cis) guy I'm dating as much as I can. We're developing a D/s dynamic and I just wanna take care of as many of his needs as possible. Last night we were dry humping through clothes. I was wearing my packer. We were eventually positioned so he could feel the full length of my packer along his taint and asshole and he went crazy for it. Neither of us had prepped for it or even really talked about me topping, and he'd never bottomed, so we put a pin in it to revisit later.
"Later" was today.
He was grinding on my packer so hard I started to get worried about it's structural integrity lol; it's a nice one and the silicone isn't really meant for that much friction, ya know? I suggested I put my strap on so it would be easier for him to grind on, but soon our horny brains took over and he wanted me inside him and I wanted to be inside him - but first he needed warming up. This was his first ass play, besides by himself, and he hadn't done much. I went as slow and gentle as possible and his needy hole sucked my index finger in quickly. He begged for a second finger, and then a third. He was frustrated I couldn't go deeper so we moved onto the strap. Oh. My. God. He took it so easily, so readily, like he'd been doing this for years. I still tried to go slow and he still required some acclimation, but soon he was using my harness to pull me in, further and faster. Again he was frustrated I couldn't go deeper with my 6" strap but still overwhelmed with it all. He made such beautiful faces and sounds for me. We tried different positions and he loved it all.
Next time we see each other, we'll go to the adult shop and he can choose whatever dildo he wants, my lil' size queen 🖤