Frustrating masturbation / ruining

I read a story many years ago (probably in Penthouse Variations in the pre-internet era) about a keyholder who had her sub lay down naked on the bed and tied his ankles/feet to the bedposts. Leather handcuffs were then attached to his wrists and a leather collar was fixed so that his head was tied to the headboard.

A long rope then went from the handcuff chain up thru an eye hook in the ceiling above the bed.

His chastity was then unlocked and he was given a tube of lube and allowed to jerk off. His KH held the other end of the rope, standing at the foot of the bed.

The catch was that the soles of his bare feet were tickled while he jerked off. If he laughed or made any noise at all, she would immediately pull on the rope, which raised his hands out of reach of his penis. Feathers, makeup brushes, and her fingers were all used as tickling implements, and she delighted in upping the tickling intensity just as his orgasm was approaching, which of course resulted in his hands being pulled off his cock.

The third time he laughed, the rope stayed pulled up and the "game" was over. His cage went back on and she then straddled his face and he had to lick her to 3 orgasms to get a chance to play again the following week.

 

Another way to add frustration is to place two feathers in his hands to tickle his cock, and allow him only that stimulation before yanking his hands away.

 

If you like tickling, they make a keyless chuck for the Dremel rotary tool. Thus, you can clamp the quill of a nice stiff feather in the Dremel and switch it on to rotate at 35,000 rpm. Imagine a lovely feather at that speed spinning in between the toes, or burrowing into the belly button.

You can also hammer a finish nail into the handle of a soft makeup brush and then use the nail to clamp the brush in the Dremel. The spinning brush would be good for the soles of the feet, sides, and maybe even the cock/balls.

A fun way to play is as follows:

She takes a bamboo BBQ skewer with a pointed tip. Sub is secure with his bare feet strapped in bondage to limit wriggling and prevent escape. She then uses the skewer to "write" letters of the alphabet on his bare feet (one at a time), and he has to determine what word the series of letters spells. This is not easy when laughing hysterically, since he has to remember the letters consecutively in his head to eventually spell the word she is writing.

For every word he correctly interpets, his bare cock is ticked with a feather for one minute.

For every word he cannot interpet, his bare feet get tickled without mercy for 5 minutes with some of the Dremel attachments.

The game last an hour. He has to get 12 words correct to get an orgasm at the end of the game. If he gets less than 12 words correct, he gets tickled all over his body for another hour and then locked back in chastity and gets to try again next week.