At this writing I am 35 years old. The story at this point puts me at around 30/31. At that point I was happily working away as a busy Pro Domme. I traveled a bit for work, around Canada and the US. I had some great adventures and everything was going smashingly. Apparently that’s not a real word but I like it anyway.

One day a new client called asking if I would consider a trampling session with a shoejob finish. This was iffy because I did not give handjobs at that time…but rubbing the bottom of my shoe against his cock until he came seemed ‘just’ okay. He sounded nice. He requested regular clothing, no fetish attire and asked if I could just act like a normal woman, not like an in-role Dominatrix. I was used to all sorts of fantasy fulfillment so I said “no problem”.

I’ll never forget how he looked laying on the floor below me, candlelit, sensual music playing, his muscles straining under my weight as I dug my heels into his flesh. He was beautiful. I thought he was years younger than me. Such a nice looking boy.

It was unusually erotic for me. I was very professional in most of my sessions but there was something different about this one. I made a note of it at the time.

He came back to see me several times. He would bring wine. I bought a special glass so I could easily pour it into his mouth while he was laying below me. I would let him stay longer. We would chat. He had excellent manners. I looked forward to our sessions. Too forward. He was a client. I needed to stay professional, but he was different. There was no real Domination, just kinky games between two people who weren’t pretending to be someone else. It was fun and it was hot.

It feels silly now how I struggled with my decision. I didn’t want to cross the line. I took my profession seriously.

Finally, after a session had gone double overtime at no charge I just said it: “I want to fuck you.”

He consented and we had somewhat awkward sex….but it had potential.

I invited him back for a personal evening, no business. We fucked for hours. It was amazing.

Things were complicated at first. I didn’t want to feel like I was getting paid for sex, but he didn’t want me to feel like he was taking advantage of the situation and getting free trampling and shoejobs. He would still book sessions and it was all business. Then when the time was up, we’d have sex. Or if I felt like company I’d call him up and go over to his place. Before I knew it, we were dating and it didn’t make sense to continue charging him.

He will be referred to as “C” as the story continues…

Sexy Trampling