My first prostate milking

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.


Initiative in our chastity relationship

I had in interesting discussion on Reddit with TomVanAllen, about one of his old blog:

I replied to him that one of the problems I was having in the past with chastity was the lack of non-humiliating role-models.

I don’t want my husband to turn into a wimp. Submissive in the sense that he obeys me? Fine. Sexy maybe. Submissive in the sense that he is passive? Forget it.

Some evenings, I take control because on that evening, I have a plan in mind. The rest of the time, I want him to court me, to seduce me, to make me advances, to show interest.

He is the one who starts sex maybe 95% of the time, chastity or not.

When I try something, it’s usually after he began. He needs to put me in the mood first. To show me that he is interested.

The reason we do sexual “stuff” (I am still having a little problem really calling what we do “sex” but I am getting there) every evening now, is not just because I have a higher sex drive, but rather because his frustration causes him to try to please me every night.

He is constantly horny. He is more passionate. When he gets home, he jumps into my arms and kisses me as if we were still 19.

That’s why we do sexual stuff every evening.

Pegging isn’t exactly what I envisionned

My wife had announced on Reddit that she would probably peg me on Tuesday evening, but that finally only occurred yesterday evening (Wednesday).

Because it was my first time, it wasn’t a full on pegging: my wife didn’t put the strap-on and instead, I laid on my side while she gently pushed her favorite dildo in my rectum, after having spread some (ice cold) KY on the dildo and on my rectum.

English: I took this photo myself, of my strap...

No, it doesn’t look like this one (Photo credit: Wikipedia)

I tried to relax, as she suggested (after all, I am the one who had introduced her to anal sex in the first place) and I quickly realized that it was a lot like trying to fall asleep: the more you try to relax, the tenser you are.

But the dildo kept progressing inside my colon and my chastity cage kept moving out of excitement. Slowly, tension  (interpreted as pain by the brain) lead to pleasure and softly, my wife began pulling and pushing the dildo which had pleasured her so often in order to cause me pleasurable sensations.

We kept talking during the process and she commented a few times that my CB-6000 was almost trying to explode from the attempted erection. She said something like “Hey little buddy, no erection until October!”, but I don’t remember her exact words as I was feeling pretty intense emotions.

The jolts of pleasures I was feeling weren’t the first one I had felt since I was last locked up: I had discovered that when my sexy wife caresses my body, I seem to feel her touch stronger. This was a little like those touches: pleasurable but far from being strong enough to cause an orgasm.

Considering my deepest fantasy is pretty much so no longer have orgasms, that kinds of suits me.

The next step, I guess, will be for my wife to use a strap-on to see if the feeling is different, but I clearly left her in charge so I have no idea when the next time will be.

And you know what? That’s fine by me. I am starting to really enjoy following my wife’s lead.