Middle school student second year. 14 years old

Enjo kōsai is a Japanese term for a transactional relationship in which older men provide money or luxury gifts to younger women in exchange for companionship or sexual favors. Participants can range from schoolgirls to housewives. The most common English translations are ‘compensated dating’ or ‘subsidized dating.’
( From Wikipedia )

When I saw her ad on social media, I didn't hesitate and responded right away. We quickly exchanged contact details and arranged to meet up.
She was a cute girl with a fairly ordinary look—long black hair, average height, a pleasant face, and her school uniform on. Just a typical schoolgirl. Her name was Miyabi Ikeda. She was 14 and in her second year of middle school. At first she seemed a bit nervous, but once we introduced ourselves and started talking, she gradually opened up.
I took her out for drinks and then dinner. We talked about everything and nothing, and the evening was genuinely fun. Afterward we went to a love hotel.

She seemed a little nervous, though it was obvious this wasn’t her first time doing something like this. Once she was naked on the bed I spread her legs and began playing with her tiny hole. She got wet fast—clearly already in the mood—so I climbed on top of her, pulled her body against mine, and prepared for the main event.
She sat up, reached for a condom on the nightstand, tore the packet open with her teeth, and rolled it onto me.

“I told you,” -she said, “it has to be with a rubber…”

No matter how much I tried, I couldn’t talk her out of it. So I guided my cock to the entrance of her middleschooler's pussy and pushed inside. She started moaning the second I was in. At first I moved slowly; her cunt was incredibly tight and gripped me hard, but the sensation was incredible.
Then I picked up the pace and fucked her properly. Her moans filled the room. I wanted to watch the pleasure on her face, but she kept covering it and turning away. So I flipped her over onto all fours and kept going, gripping her waist tightly as I drove into her until I came, completely filling the condom.

Afterward I sat beside her, catching my breath. She lay face-down, still completely naked, scrolling through her phone. Looking at her, I couldn’t help thinking how much I’d love to grab that flat little ass and bury myself deep inside her again. Maybe next time I’ll have better luck convincing her to let me go raw. It’s worth a shot.