So, Sunday was my first milking. I have been interested in long-term chastity for years and as such, knew that if I ever got my fantasy fulfilled, my prostate would be milked.

I had even bought a prostate massager but it had never been used.

Last week, my first pegged me for the first time and it wasn’t unpleasant at all, so when it was time Sunday evening for the milking, I wasn’t nervous at all.

My wife on the other hand, was on the verge of a nervous breakdown: she was afraid she won’t be able to do it or that she would hurt me or that it would turn her off so much that the whole “chastity thing” would be over again because of her.

I tried to reassure her as much as possible and eventually, I managed to get her in the bathroom where we began to test it. I suggested the bathroom because the ceramic floor is easiest to clean…

Initially, she was finding it very awkward, but slowly, she warmed up to the idea that it was for my health. We had read that the first time, it could take 30 to 60 minutes and that estimate was spot on: the first small drop of semen was released after roughly 40 minutes.

I saw it but I must admit that just like we had read on the Internet, I couldn’t really feel anything: it was entirely without pleasure or release but the prostate massage was rather pleasant itself.

Over the next few minutes, my wife continued the process and emptied, drop by drop a rather large quantity of sperm on the bathroom floor and inside the CB-6000 itself.

It was my first ejaculation since April 4th (even though I was only locked on April 6th), leaving I guess 24 days of accumulation on the floor.

Later, my wife admitted that it wasn’t as bad as she thought it would be, but recommended that we did not perform future milking in the evening to give time for her sex drive to resume in time for the evening.

Still, I think this was an important milestone passed for us.