My first opportunity to slide my fingers into the arse of a man for the purpose of stimulating an emission from his prostate took place very early in the morning one day last year. I joined the crowds of people traveling in to the city to begin work. My needy submissive male, I'll call him billy, wanted his prostate milked in his office before the days work began.
Knowing that to all the other occupants of the office building I would be a professional attending a breakfast meeting made the choice of clothes much easier. A smart wool skirt that curves suggestively across my bottom and a formal shirt. As I didn't feel any need to wear lingerie that made concessions to male taste my stockings were black opaque and the panties fully covered my tush. Master wanted me to wear a black leather jacket but the weather was awful and so that assertive look was replaced with a classic coat.
Billy had been given instructions on the purchases he had to make, the cleansing that had to be done to his genitalia and how he should greet me when I arrived. I was certain that he would follow them and in that I was not disappointed. I entered a warm office that was surprisingly large. Space had been cleared so that billy could spread a rug on the floor which he had topped with a towel. Hesitantly he indicated the box containing all the accoutrements and then began to take the items out one by one and show me before laying them out on his desk. I was pleased to see how much care he had taken.
We were ready to begin, I washed my hands and he stripped hurriedly to be on his knees on my return. It was time for him to request the milking. I didn't feel he had expressed enough sincerity and demanded he try again. Then he showed more feeling. He revealed that he had been incapable of maintaining sexual abstinence and that earned him his first spanking. I watched as my hand prints turned his buttocks red.
I had billy position himself on all fours with his arse high in the air. It felt good to run my hands over his back and then add a few more quick slaps. As I pulled on the gloves I told him what I wanted, told him that his hands must never go near his cock and told him to please me. Even though he had ensured his cleanliness I took a baby wipe and slowly slid it around and down his cock. Then with a fresh one his balls were swiped. His arsehole felt the last one I pulled out.
Did I tell you his cock was fully erect? A little oversight, it stood to attention desperately straining for the touch of fingers.
My fingers were lubed. I began with my index finger. Sliding it slowly but firmly in that puckered hole. Gently I circled my finger, then withdrew it to send my middle finger in its place. As my right hand was fully occupied with billy's arse it was my left that teased his cock. I stroked until he began to buck and jerk when I took my hand away and told him to relax and breathe through the need to orgasm. He suffered and I watched as pre-cum drained from his cock.
I began again to tease his cock and continue the gentle stroking in his arse. He reached out to touch me and his hand wandered up my thigh. I allowed him to feel my stocking tops and then pushed his hand away and spanked him a few times. Once more he came close to orgasm and we stopped as more pre-cum dripped to the floor.
I took off those gloves and carefully replaced them. With a handy piece of rope I tied up his balls which it was clear he really wanted. Then I lubed up again to slide two fingers into his arse and resume the milking activity. This time when his hand wandered up my leg I let him stroke his fingers against my pussy through my panties. Although his orgasm was being denied I was feeling very hot and wanted that pleasure for myself. As I came I bit his bottom.
His wandering hands couldn't continue. His hands were secured behind his back and they stayed there until I was almost ready to leave. Some teasing time for him as I lifted my skirt to show him my panties and then sit and stroke my pussy that was still aroused. A good opportunity to talk about what we were doing and how important it was to please me.
I stood smoothed my skirt back down over my legs and the milking restarted. It was quite amusing to watch his cock and listen to his groans. It was very enjoyable to pull of the rope tie and play with his balls. It became tiring to continue stroking his arse.
We were not successful at milking billy's prostate. I made him suffer for as long as I could but our time ran out. He was given two minutes to wank himself and I watched as he did so. He came when I stepped behind him to whisper in his ear.
We will continue to practice the prostate milking on a regular basis until we are successful and the requirements will increase for billy so that I am amused.
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