You take the pain but the stimulation proves to be too much.

“One.” You announce, wishing to show no fear and wanting to get your chastisement over with as quickly as possible.

Diego leaves the cane firm against your ass for a few seconds before slowly removing it, creating a terrible void. Next comes a cruel swishing sound followed by a thunderous crack as the rattan explodes across your bare ass.

A slight grunt slips through your clenched teeth. The pain is far greater than you thought it would be. Besides your ass being lit-up, the **** of being jerked forward from the blow causes your cock to be cruelly yanked down as it presses hard against the unyielding oak. Without thinking your heels hit the ground as you rock backward trying to gain some relief for your abused and swollen manhood.

“The position you're in is meant to increase the torment of men who lack the ability to control themselves.” The Caribbean witch lectures you. “Unfortunately, for men so endowed as yourself, it is especially cruel.”

You feel the cane return affirm against your ass, this time a few millimeters below what must be a large welt from the first stroke. “Back to position, Mr. Danton.” Diego commands, “And start from the beginning.“

Pushing up with the cane your boss guides you back into position as you go on your toes and raise your ass high once again.

“One.” You state as the stoke lands above the first and then the next below. This witch is either stronger than she seems or is very skilled with the cane, probably both. You give out faint gasps with each lash, but remain in position.

The fourth lands right over where the place of the first strike and stings like hell. A guttural “fuck!” slips from your lips as your head jerks up and your heels once again drop to the ground.

“In my country.” Diego pontificates, “the maximum stokes a man can receive is twenty-four. This is only for the worst criminals, for such an amount could hospitalize the condemned and certainly would leave life long scars.” You feel Diego's hand caress your searing ass as she inspects the damage. “We begin again, Mr. Danton.”

The sudden switch from such brutality to Diego's gentle touch sends shivers through your body, as if a spell has been cast on you. Waves of pulsating desire throb through your cock which quivers towards an orgasm. There is no doubt in your mind you can take the pain, but you are beginning to fear your manhood will surrender.

“Back to position, Mr. Danton.” Your boss orders. “Consider yourself lucky that I am now **** to let up a bit on your punishment. Not out of any concern for you, but for the need for a fully functional employee this day.”

“One.” You proclaim, resolved not to give again.

This strike lands solely on your right cheek. Since far less of the cane hits flesh it's mercifully less painful. It does cause you slide to the left of the chair, further abusing your pulsating cock. The second is to your left ass cheek, forcing you to slide back to the middle.

When the third lands again on your right cheek you realize Diego's sadistic game. “Damn her” you think as with each stroke your ass dances back and forth across the chair, dragging your enraged cock with it. The pain might be less but the stimulation is far greater. She is forcing you to masturbate.

Diego continues this relentless pattern. With the fifth stroke your breathing becomes heavy. By the seventh you being to groan as your aching cock is brought ever closer to sexual defeat.

After the ninth kiss of the cane you know you will not last. Clenching down on the chair's seat your knuckles go white as you try to muster the last of your failing strength to avoid the inevitable end. With all your focus on your cock you forget to count and then fail to hear Diego's insistence that you continue.

“Mr. Danton!” Your boss finally gets your attention. “I do not like repeating myself especially when I am showing such leniency.” The cane again presses hard against your sore ass. “You will receive an additional two strokes bringing the new total to fourteen.”

“No.” You cannot help but gasp.

“Then we will make it sixteen.” The witch will allow no quarter. “Get going Mr. Danton, less the count starts at one again.”

“Ten.” You are able to gasp out.

“Thwack” the bitch hits you hard on the side of your right ass, right on top of a particular large welt, causing your cock to slide hard and far across the wood.

You manage to say “eleven” which brings a similar treatment to the left cheek. You groan and press your weapon hard against the wood while mentally trying to clamp down on your muscle, desperately trying not to explode, as a bit of cum begins to seep out.

Your heart racing, your breath sporadic, again you take too long trying to muster your will.

“You're now at eighteen. Mr. Danton.” Diego announces.

“Twelve” you stammer, knowing full well this witch has won the battle.

As the cane bites hard into the center of your ass. First there is a grunt from the pain, followed by the vain struggle trying to resist the inevitable, before a groaning hiss of “noo” as you explode.

Wave after of wave of pent up frustration surges through your cock as streams of cum jet forth splatting are over the chair, yourself and floor. You can't help but to hump the chair as the intensity of the orgasm overtakes you.

Ejaculating in front of Diego is bad enough, that this witch has caused the most intense orgasm of your life by beating you with a cane is shameful. Collapsing over the chair, your feet now flat on the ground, you try to regain your breath as cum still drips from your now semi-erect defeated cock.