Painful Anal with My Boyfriend — Rare but Deeply Intimate

We don’t film anal videos often, and here’s why — it’s painful. Not in a fake, acted way, but really intense and challenging. I love anal sex, but my tight little ass doesn’t take his big, hard dick easily.

In this video, we took our time. Lots of lube. Lots of breathing. The first thrusts were uncomfortable, sharp — my body resisting every inch. But as he went slow, shallow, and careful, the pain started to melt into pleasure.

There’s something raw and honest in this experience. I moaned not just from arousal, but from real sensation. It’s hard to describe how pain can shift into something satisfying, but when it happens — it’s unforgettable.

We don’t do this often. That’s what makes this scene special. Intimate, real, and completely unscripted.