Tickling his prostate

As I have become more comfortable and confident with my dominant persona the relationship with Billy has broadened and the initial reason for our meetings become long overlooked. I had never successfully milked him and this irked me so I decided it was time to try again.  A text was sent and a time specified for us to reconnect. 

I carried with me a small bag with a vibrating prostate tickler that he had never previously seen, a short length of rope and my favorite leather strap.  The strap wasn't really needed but I like to feel it in my hand and it could always be used to bring him back into line if he misbehaved. Misbehavior was to be expected after so many weeks of work coming between us. 

The room was warm when I entered. As he presented himself naked at my feet both my coat and my dress came off to reveal a short slip and stocking tops. He nestled his head between my thighs and breathed deeply. His hands wandered attempting to lift the slip so more could be seen. I reached for the rope and pulled his hands behind him to quickly secure them. 

Today he was going across my lap for a warming hand spanking. How awkward it is for a tall man to fit across the tiny lap of a petite woman. His stiff cock pushed into my legs and I reached a hand under him to grip it hard. Holding fast I began to spank his cheeks making them pink but not warm. Heavens he does squeal and squirm, you would imagine the spanking was being given by a hefty man.

I grabbed the leather strap and let it fall. It is very satisfactory to hear the sound of it landing on flesh. Despite his yelping I managed to give him a good dozen purely for my pleasure.

Billy was released and told to bend over the chair with his legs spread. I reached for the gloves and lube and he understood what was to follow. I talked to him about how long it had been since I had tried to milk him and my desire to try again. I began slowly, circling the outside of his arse with two fingers, drawing out the time before penetration until his body was writhing for it. 

His arse hole was so tight but as my first finger entered he groaned with pleasure. A second finger spread his hole wider and I felt so much more competent to stimulate him. I touched the tip of his cock and let the precum heighten the sensation. My free hand stroked from the tip of his cock slowly back to the entrance of his arse. With each stroke his sense of bliss deepened. 

I took away my fingers and inserted the tickler. Setting it to vibrate I held it in place and continued to stoke his balls and cock. I can only assume that the pleasure was intense as billy became incoherent. 

Two or three times I halted this process to present a part of my body to him for worship. First to his great displeasure it was just one pussy lip. He got roundly castigated for complaining and replaced his sulky look with one that was more appropriately appreciative. Another time it was a pretty pink nipple, finally it was my clit.

Each break was just long enough that his arse hole tightened up and had to be reopened. Fingers followed by the tickler. Getting closer and closer to cumming. But I continue to be impatient..........milking did not occur this time either. I wrapped a fist around his cock and gave the instruction to fuck my hand.  Well bugger me! Billy fucked back and forth once or twice and then dropped his load.   

When it was finally possible to get sense from him he apologized, I had just taken him too close and ejaculation was impossible to stop.