When I (25F, 23 at the time) first started domming, I was mostly looking for chastity and experimenting with trying to peg or do anal stuff with my partner. See if maybe I liked it but I wasn’t sure how enjoyable I’d find it. (For the record, I don’t receive ever on anal so anytime I refer to it, I’m on the top end. Tried it once and hated it)

My first partner (20M at the time) I had talked to was open about wanting anal play in the picture, and since it was on my bucket list, we got into routines of him stretching and getting used to taking bigger and bigger dildos on calls. He became a size queen honestly and kept trying to upgrade the girth after he maxed out how deep he could go.

During this time, it was fun seeing his ambition and how slutty he would get with it. So when things started to move to in person, I felt hesitant but excited to see how it was in person.

When we had eventually met up at a hotel, I had him stretched pretty well with regular online sessions at this point. He prepped in the hotel bathroom, cleaned out, and I lubed him up.

This is where I started to realize I loved the anal play aspect. It was my first time exploring a man down there, and honestly the fucker melted as soon as I figured out how to hook my fingers for the prostate.

Once he was ready, I strapped up, lubed up, and slid myself in. While I don’t have a dick, the resistance could still be felt and seeing him throw his head back did something to me. I fucked him hard in the mattress and it just… felt good to top. There wasn’t physical pleasure but to see someone submit under you and to your “cock” felt amazing.

Needless to say we spent the next few days with me doing most of the penetrating and getting him used to it. Looking back, I was awkward with my thrusting and had no clue how to do it well. It’s not like you usually do it much if you bottom and don’t have the “hardware”. But I picked it up fast and knocked the wind out of him a few times by the end of the trip. He was good about taking it after being so accustomed to bigger sizes where I could use smaller dildos and really go to town without fear of tearing something.

Needless to say I’m hoping to get into more pegging in the future and I don’t think I could be with a guy who doesn’t want to get pegged. 10/10 would do again