(In this post, Lady and cagedmonkey tandem post on the same subject. These are not conversations, per se, simply viewpoints from the female and male perspective.)

Lady: Cagedmonkey has been denied orgasm for a couple of weeks now so I thought it might be fun to milk him. I haven’t ever milked him properly with an internal prostate massage so it was my mission to get it done! I have milked him a little bit with an external massage before but it wasn’t anything to write home about.

The other night I cuffed my boy to the coffee table on his belly. I got out the bottle of lube and the anal-t vibrating prostate massager. Since I really had no idea what I was doing, specifically, I played around a bit with angle and depth and that sort of thing. So with one hand I was adjusting the massager and the other I used to massage and push on his perineum so his prostate got as much stimulation as possible. At times I could tell I was hitting something just right because he would let out a pretty good moan. I did this for about 45 mins and while he was dripping precum pretty well I wasn’t getting that good amount of fluid that I wanted and have heard so much about!

That’s when, with the massager against the palm of one hand, I pushed up on his perineum with my fingers of the same hand and grabbed his cock and stroked a little with my other hand. I only stroked a few times (medium speed) and he only spasmed once and out came a huge squirt of what looked like milky water! Then of course I had to do it again so I stroked him another couple times and he dripped out a few more big drops of the milky fluid. Oh, not to mention, the very loud moan each time as well. I know he didn’t orgasm, he lacked the spasms for that and what came out was not thick like cum usually is. It really was just a thin milky colored, water-like fluid. It was hard to even show him how much after since it just made the towel wet.

It was a pretty neat experience but can be discouraging when it takes so long. I bet if we do it more and hubby is able to relax a bit more it can happen faster. I guess we’ll just have to practice more! 🙂

cagedmonkey: I will admit, the idea of being milked by My Lady is very exciting. The possibility of her extracting the cum from my full swollen balls without allowing me the pleasure of a full orgasm involves a level of control that is off the charts. And to be honest, I want to be controlled like that.

ML has attempted to milk me in the past, with varying degrees of success; most of these attempts resulted in either a ruined or minimized orgasm. This was probably her most successful go at it. ML had me strapped down and unable to resist, and she used my helplessness to her advantage by taking her time and being patient.

ML has learned how to use the prostate massager very well. She was hitting all of the right spots; I was feeling flash after flash of pressure overload sensations, the signal that my milking was imminent. It was a little difficult for me to relax and let go because I was afraid I might end up peeing, but I think if she had continued with stimulating those sensitive spots I wouldn’t have been able to hold back any more.

After who knows how much time I spent on strapped to the table, my ass being penetrated and my prostate massaged, throat hoarse from near-constant moaning, ML began to stroke the cock in rhythm with her thrusting. I got closer and closer to orgasm until just at the last moment she stopped her stroking…. and I felt the “cum” shoot out from me! I could feel soft spasming in both my cock and asshole; I wasn’t quite sure if I had cum at first. But afterwards – when I was still horny and wanting to cum – it was obvious that I hadn’t. Some of the building pressure in my balls was relieved, but the need to cum was still there.

I’m not sure if we accomplished the classic definition of “milking,” but whatever we ended up doing was pretty intense! Overall, it was fun and something I am definitely interested in trying again!