Jaylin Matthews my personal assistant, that is to say my secretary was also my daughter Tera's bestfriend. Ms Matthews worked with me in my home office keeping everything ship shape as it were.
Five-feet seven inches Jaylin's long nut-brown hair was always neatly piled up on her head. Oval wire-framed glasses that rested nicely on her small button nose helped bring out the color of her striking blue eyes.
It was 8:15 Am and I sit in my chair reading my newspaper and drinking coffee. Jaylin was twenty minutes late, the third time this week but I don't worry about it. Its Friday and Ms Matthews knows what to expect when she shows up today.
Rushing down the stairs Jaylin came into the office and came to an abrupt stop when she saw me sitting in my leather chair reading.
"Sorry sir." Jaylin blurted out. "I know I've been late alot this week."
She looked down at her black strappy shoes, her hands dropping to the sides of her tight short business skirt. Under a form fitting but simple gray sweater top two perky nicely shaped breasts stand out.
"We'll handle that in a moment Ms Matthews." I say glancing back at the paper. I see out of the side of my vision that she nodes and goes over to a corner of the room.
Returning to where she had previously been standing Jaylin is now holding a straight eight-foot long two-inch thick rattan cane.
Standing after a moment I go over to Jaylin and take the rattan that she is holding. We've done this often enough, weekly infact to make a routine of it. I place a hand on Jaylin's back and guide her foreward without needing to issue a command.
Reaching forward Jaylin takes her hold of her ankles above the straps of her black pumps, a corkscrew of brown hair breaks free and dangles just above the maroon rug of the home office.
Behind Ms Matthews I take hold of the hem of the tight skirt and pull it up over her hips to the small of her back exposing an inviting sight of two nicely curved thighs and buttocks calling to be caned encased in nearly translucent black thong panties.
I grasp the sides of Jaylin's thong and pull the panties down to just below her hips. Then I take the rattan and rest it in the cleft of her ass returning to my chair to complete the newspaper and my coffee.
From my chair I hear Ms Matthews sigh but say nothing I watch her keep her with her lovely little nose to the floor. She breathes steadily patiently awaiting me to administer her thrashing.
"What do you and Tera have planned for this evening?" I at last ask.
"Clubbing sir." Jaylin says with the slightest hint of fear perhaps anticipation in her sing song sweet voice.
Completing my coffee and paper I get up and reach for the cane, Jaylin noticeably stiffens as I stand behind her with the rod. Her thighs become taught and she grasps more firmly to her ankles almost holding the straps of her shoes.
Taping the rattan on her toned tan ass I then raise it up above my head to only slash down with the full strength of my right arm.
There is a gasp but no other outcry from Jaylin as the stroke connects with her firm bottom cheeks.
The next stroke bounces off the underside of her thighs and these rewards me with a tiny aborted cry. Stroke three quickly follows producing a very girly yelp from the young woman subject to the cane.
Four and five land in succession being met by restrained grunts and gasps I must admit that they were pretty hard the rattan bending around the curves of her thighs I am impressed that Jaylin managed to hold her place.
Jaylin is now openly crying and forcing herself to hold her place she knows that getting up or swearing will only lead to extra strokes and that they will be doubly as hard as what she is all ready getting.
Ridged welts crisscross Jaylin's pert bottom, she flinches and clenches her cheeks together in a vain attempt to conceal her womanly virtues but the inviting pink pussy is well on display for me and as always I feel my own desires rise.
Whimpering waiting for the next cut Jaylin rocks slightly in her place.
Tapping the tip of the cane on the highest peek of her ass I snap it back and am admiralty pleased by the result of my efforts.
"FUCK!" Jaylin cries out.
I note that the last stroke produces a nasty looking purplish weal.
Sobbing and speaking through her perfectly white teeth Jaylin says: "I'm sorry sir" it is said with the profound horrific knowledge that she has added three extra strokes to her dozen.
I give her the next three strokes firmly landing them over her rounded bottom one after the next Jaylin only cries and holds her ankles with a steadfast grip.
We are at last reach the final three of her original caning these I give with precision causing her to cry out loudly at each one.
Completing the original caning I stand and look at my work. Ms Matthews's rear end is expertly marked and I wonder where I shall land her extra three cuts without do to much more damage to her shapely ass.
Sniffling and Jaylin says: "I'm ready for my extra sir"
I see her bite her pink lips and add. "Please, please do it fast... I know I shouldn't have said that naughty word it just hurts sooo much." Jaylin pleads.
Doing as Jaylin wishes I give her the extra strokes at a fast pace, though they are no less hard then the first twelve cuts of the rod they are in truth much harder since I am putting the weight of my whole body into each one. She whimpers and cries even at last begs for it all to end.
I must say that I admire her strength and endurance. Over this past year and half Ms Matthews has become much more able to take her whippings without out to much disruption or protest. I think what made it easier was having the opportunity to witness Tera take a dose of strict discipline from me.
Telling her to stand up and dress herself Jaylin adjusts her skirt wincing as she pulls it over her bruised bottom. It's going to take some effort to not shift and fidget in her chair today.
Sitting in her chair crossing her long legs, the pain of her caning shows clearly on her lovely face. Jaylin opens her note pad and taps her pen she even mangas to broadly smile at me and says: "I bet Tera's in for a good sound whipping for skipping class yesderday."
Now I had no idea that Tera had not attending her college class the other day. Ms Matthews of course knew this when she dropped this fact. I shall attend to my naughty daugtters rear with at much precision as I have her friend Jaylin.
Jaylin despite her pain smiles and we began the workday waiting for Tera to pop her head in to say hello. Ms Matthews was lucky she didn't have an audience for her punishment Tera won't be so lucky.