The weekly attempts to milk billy's prostate continued with amusement for me and extended pleasure for him. I sent him to my favorite fetish store to buy a butt plug so that he could begin to loosen up his tight little anal sphincter for me. He complied very quickly with my instruction and then began to insert the plug each morning for a set time.
To no one's surprise, I am sure, he reported back that he got an erection every time and dribbled precum that made his undies wet. I trust that he was truthful when telling me that he refrained from touching himself or cumming.
I hadn't given him the benefit of advice on selecting a butt plug preferring to see what he would select. He chose a small black rubber plug that he very soon discovered would not remain tightly inserted in his butt but would slip out at the first opportunity. So he returned to the store and purchased an inflatable plug that he could pump up to fit snugly. I was impressed by his perseverance.
He laid both of them out for me to inspect on the next assignation. I could see that the small rubber plug would be useful for me to use to open him up a little so my fingers could slide into his ass with greater ease. He had to wait for that though as I wanted to put him across my knee.
Billy is a tall man and it must look rather ridiculous when he stretches across my petite lap. He wriggles and squirms most appallingly and I know it is so that his cock can rub against my thighs. So he receives a severe spanking and quite a lot of verbal admonishment. But I enjoy the sight of his bottom waving around so spanking cross the lap continues when really such a bad boy could be punished more effectively in a different position.
When his bottom is nicely pink and my hand tingles with the effort expended it is time to move on to the prostate massage. He kneels on all fours and presents his ass for my attention. I make sure he is aware of the gloves sliding onto my hands and that he hears the sound of the lubricant squirting out of the tube. My fingers begin to circle his tight pink hole and slip slop the lubricant into place. A condom is put on the plug and I begin to gently massage his ass with it. His cock gets to feel a gloved hand teasing the glans and it jerks about releasing precum.
Billy begs to taste my pussy but this week he is in for disappointment. I tease him by stopping the massage and wiggling my butt in his face, he is quite pitiful in the moaning he makes. I return to his ass and let my fingers do some work.I am becoming smoother in my stroking action and it is clear that billy gets a lot of stimulation. Still I cannot generate the emission of semen that we are seeking.
I decide that this time I will do a count down to his orgasm. It is not my intention to make him fail on this occasion but use it as a fact finding mission to know the number I can select that will lead to failure. He is told to kneel up and when I have his eyes linked to mine tell him he can cum if it is done by the time I have counted to thirty. I begin to count and looking eye to eye he begins to wank. One......to ......twenty eight, semen goes everywhere and he is limp with bliss.
I wonder if he is aware of my evil intentions for the future.
To no one's surprise, I am sure, he reported back that he got an erection every time and dribbled precum that made his undies wet. I trust that he was truthful when telling me that he refrained from touching himself or cumming.
I hadn't given him the benefit of advice on selecting a butt plug preferring to see what he would select. He chose a small black rubber plug that he very soon discovered would not remain tightly inserted in his butt but would slip out at the first opportunity. So he returned to the store and purchased an inflatable plug that he could pump up to fit snugly. I was impressed by his perseverance.
He laid both of them out for me to inspect on the next assignation. I could see that the small rubber plug would be useful for me to use to open him up a little so my fingers could slide into his ass with greater ease. He had to wait for that though as I wanted to put him across my knee.
Billy is a tall man and it must look rather ridiculous when he stretches across my petite lap. He wriggles and squirms most appallingly and I know it is so that his cock can rub against my thighs. So he receives a severe spanking and quite a lot of verbal admonishment. But I enjoy the sight of his bottom waving around so spanking cross the lap continues when really such a bad boy could be punished more effectively in a different position.
When his bottom is nicely pink and my hand tingles with the effort expended it is time to move on to the prostate massage. He kneels on all fours and presents his ass for my attention. I make sure he is aware of the gloves sliding onto my hands and that he hears the sound of the lubricant squirting out of the tube. My fingers begin to circle his tight pink hole and slip slop the lubricant into place. A condom is put on the plug and I begin to gently massage his ass with it. His cock gets to feel a gloved hand teasing the glans and it jerks about releasing precum.
Billy begs to taste my pussy but this week he is in for disappointment. I tease him by stopping the massage and wiggling my butt in his face, he is quite pitiful in the moaning he makes. I return to his ass and let my fingers do some work.I am becoming smoother in my stroking action and it is clear that billy gets a lot of stimulation. Still I cannot generate the emission of semen that we are seeking.
I decide that this time I will do a count down to his orgasm. It is not my intention to make him fail on this occasion but use it as a fact finding mission to know the number I can select that will lead to failure. He is told to kneel up and when I have his eyes linked to mine tell him he can cum if it is done by the time I have counted to thirty. I begin to count and looking eye to eye he begins to wank. One......to ......twenty eight, semen goes everywhere and he is limp with bliss.
I wonder if he is aware of my evil intentions for the future.
Jeez! I almost came without touching reading this.
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