Milking His Prostate

My husband, Owen, and I recently took turns choosing ways to expand our sexuality.  We each took turns suggesting something to try that the other person "had" to do.  Owen chose first, and he was adamant about making me squirt.  It might be a story for another time, but spoiler alert, it just didn't happen after several sessions of trying.  When it was my turn to choose, he said, "Let me guess, butt stuff?"  Yes, I wanted to milk his prostate.

To this point, I've done limited anal things to him.  I would sometimes rub the external area or occasionally stick a finger in slightly during a blowjob.  He was up for trying anything but was a little concerned about the cleanliness factor.  After showering and doing an internal rinse, he was ready to go.

I did my homework beforehand and had a game plan for what to do.  This was my first attempt at anything like this, but I was comfortable experimenting.  We laid a towel down, and I instructed Owen to "get in the doggy position".  We did a little shifting, spreading his legs apart and getting his bum pointing more upwards.

I got our lube out and popped the cap open.  Owen removes all of his pubic hair, including the hair behind his balls, on his cheeks, and in his bum crack right on down to the hole.  I squirted lube onto his hole and immediately started to massage it in with a finger.  After a little warm-up, I began pushing in slightly to get him used to the feel of my finger.  I could go in about a knuckle before adding more and more lube.  One finger could now explore completely inserted.  I moved my finger in and out, relaxing the area.  A second finger joined in, and he was moaning softly now.  He was totally relaxed.  When I'd completely remove my fingers, his hole stayed open a bit, welcoming me to come back for more.

Now, in search of his prostate, I began to explore his front side from within.  It was instantly discernible, and his reaction was extra confirmation.  I tried all kinds of rubbing techniques and pressure levels, but what got the best response was massaging in circles and changing directions.  With my other hand, I massaged his testicles.  His breathing increased and became more shallow, and his legs started to quiver.  He told me not to stop.

I kept an eye on his cock, rock hard and aimed downwards, with its foreskin retracted.  A thin, mostly clear fluid began to drip out.  It was very stringy and extended from the tip of his cock to the towel below.  As the prostate massage continued, thicker droplets began to emerge, followed by the thinner string.  I changed my technique from circular motions to rocking my fingers back and forth over the length of the bulb.  It was immediately met with louder moans, and considerably more fluid flowing from his cock to the towel below.  I was shocked how much fluid there was.  It just kept coming!

Owen, almost sounding like a plea for help, finally asked, "Stroke me, please".  I released my grip from his balls and stroked his cock with my other fingers still in his ass.  I didn't get more than three strokes in before the leg trembling quickened.  His hole clenched tightly around my fingers while he orgasmed.  A few spurts of cum landed on the towel below, followed by the thin, stringy fluid that remained.

I removed my fingers and he collapsed on the floor.  He said he had no idea his body was capable of such pleasure, and he felt ten pounds lighter!