My Initial Prostate Milking Experience

Up until just two days ago, my KH never considered anything anal-related. We stopped by a “marital aide store” where she bought a mini-bullet vibe and a strapon. On Thursday night, we played around a bit while I was still caged. Having enjoyed some back door play before, this felt good. She applied lubricant, teased me gently, and then we went to sleep.

The next evening was quite different. After making out, biting, slapping my face, and spanking, she instructed me to get on all fours with my head down and stay silent. She removed my cage and I became erect right away. I felt her lube me up as she adjusted the harness. Previously, only a finger or about an inch of this toy had ever been inside my rear end. This piece isn’t small; it’s roughly 8 inches long with a diameter of 1.5 inches, has two slightly flared sections, and features a curved tip. She inserted it slowly. After ten minutes, she pushed it all the way in. It was uncomfortable but left me feeling wonderfully full. Then she began to fuck me, adding more lubricant as needed. She didn’t hold back, varying her speed with both long and short strokes. I had never experienced anything quite like it. Throughout the whole time, she scratched, bit, and smacked my buttocks while calling me a good little bitch. This intense session lasted about an hour—I really did watch the clock.

Afterward, she told me to roll over. As I moved, I noticed the towel beneath me was soaked right where my penis rested. Lying on my back, she removed the dildo from its harness and reinserted it manually. She gave me two minutes to finish, but I only needed about a minute since it had been six days since my last release. When I asked for permission to cum, she said yes but then took the dildo again, pressing firmly into my prostate and holding it there through my peak pleasure moment. Afterward, while keeping the toy in place, she grabbed my shaft and delivered some post-climax torture. It was the most intense orgasm of my life, though I had very little fluid to show for it. I assume everything else was milked out during that first hour. The aftercare/torture phase was wild and brought tears to my eyes. My buttocks are sore this morning, but I can’t wait to do it all over again.

Does anyone here want to share their own experience?