Friday

Stockings, Ass, Hold Ups, Panties


Five-feet seven inches, Jaylin’s long nut-brown hair was always neatly piled up on her head. Oval wire-framed glasses rested nicely on her small button nose only helped bring out the color of her striking blue eyes. Ms Matthews worked with me in my home office, keeping everything ship shape as it were. That is to say, Ms. Matthews was my personal assistant, my secretary, also my daughter Tera’s best friend.

It was 8:15 Am, and I sat in my chair reading my newspaper and drinking coffee. Jaylin, was twenty minutes late, the third time this week, but I didn'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 and glance back at my paper. I see out of the side of my vision that she nods 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 rattan cane.

After a moment I go over to Jaylin, and take the rattan she's holding. We’ve done this often, weekly and enough to make a routine of it. I place a hand on Jaylin’s back, guide her forward without needing to issue a command. 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 her 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 black thong panties. I grasp the sides of Jaylin’s thong, and then slowly 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, so I can complete my newspaper and coffee.

From my chair I hear Ms Matthews sigh, yet say nothing. I watch her keep that lovely little nose pointed toward the floor. She breathes steadily, patiently awaiting me to administer her thrashing. “What do you and Tera have planned for this evening?” At last I ask.

“Clubbing, sir.” Jaylin says with the slightest hint of anticipation in her sing-song, sweet voice.

Coffee and paper done, 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 pert, out thrust 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 this rewards me with a tiny aborted cry. Stroke three quickly followed, 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 and 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, now openly crying, forces 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 already getting.

Ridged welts crisscross Jaylin’s tight 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 back and forth 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 have at last reached the final three of her original caning, and these I give with precision, which cause her to cry out loudly.

Completing my job of her original, earned strokes, 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 doing too much more damage to her shapely ass.

Sniffling, Jaylin says: “I’m ready for my extra, sir”

I see her bite her pink lips and she adds. “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 than 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 too much protest. I think what made it easier was having the opportunity to witness, Tera take a dose of strict discipline from me more than a few times.

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.

Carefully sitting, crossing her long tan legs, the pain of her caning clearly shows on her lovely face. Jaylin, opens her note pad, taps her pen, she even manages to broadly smile at meand says: “I bet Tera’s in for a good sound whipping, for skipping class yesterday.”

Now, I had no idea that Tera, had not attended her college class the other day. Ms Matthews of course knew this, when she dropped this fact. I shall attend to my naughty daughter’s rear with at much precision as I have her friend, Jaylin.

Despite her pain, Jaylin smiles and we begin 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.


Roadrunner Books

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