Fond Memories

Formative experience of fingering a man

2 min read

white ipad mini on black textile
white ipad mini on black textile

I remember him, laying on his back, holding his legs in the air. Looking at me with a mixture of excitement and worry.

I lubed up my fingers.

"Wait. Will it hurt... A lot?" He's nervous. He asked me to do this not five minutes before, but in the final moment it truly dawned on him what he had asked for. He had never tried a finger, nevermind anything more. He had only just let me rim his ass for the first time. This was a little fast.

I shook my head. "It won't hurt"


"Just relax, breath"

I abandoned the thought of fingering for a moment to kiss the inside of his thighs. He smelled like a mixture of cigarette smoke and musk. Something I usually hated. But on him it was intoxicating. I looked up at the tattoos on his arm. I can't remember what they looked like, I just remember how he was enthusiastically explaining the process and meaning behind each one earlier that evening. He was so happy, so engaged. And now he's holding his legs up for me, expectant, but scared.

I spent some time working on his inner thighs until I felt him calm a little. He watched as I lubed up my fingers again.

"Ready?" He nodded.

The moaning started immediately.

"How's that?"

"Mmm good"

"Does it hurt?"


He had my full attention. In that moment, he was the only person in the world. I wanted more.

"Can I do two?"

He gasped, and with a quivering breath let out a "No"

It's been a few years and I still wonder what it would have been like to go all the way to pegging that night. It would have been my first time, but I was already intoxicated by the idea.

In this moment, I realised I loved being in control. To give a man pleasure that he's never experienced before. To see the look on his face. Hear his moans. Feel his body move underneath me, reacting to my thrusts. To feel his hole tightening around me.

I obsessively masturbated to the thought of him for what must have been over a week. I was obsessed with the smell he left on my bed, and the way his muscles looked when he tensed up before relaxing into the moment. We only met up once more after that. I don't even remember his name. But the impact he left was substantial.