Her face flaming, Cynny did as ordered, lifting her skirts and bending over the naughty seat, though it shamed her deeply to have to bare her own bottom for punishment. Once she was in position, she fervently wished she had taken to wearing drawers like some of the other girls. But she had never had the luxury of undergarments while living on the street, and she hadn’t thought the three pairs she’d been given along with her new clothes upon arrival at Talcott House were very comfortable, so she usually never bothered wearing any.
Not that wearing drawers would have saved her from a bare bottom spanking, she supposed. If she were wearing a pair, she had no doubt the headmistress would order her to reach back and part the slit of her drawers. But at least the undergarment would’ve hidden some of her private area from Miss Wickersham. Oh, how humiliating it was to know the area between her thighs—her kitty—was on full display to her guardian as she remained bent over the naughty seat, awaiting the firm application of the ruler.
Miss Wickersham moved to Cynny’s side and placed a steadying hand on her lower back. Cynny’s stomach promptly flipped and she couldn’t help but clench her behind in anticipation.
“Young lady, there will be no tensing up during your punishment. If you don’t relax those naughty cheeks of yours, I will do something to force you to relax them. Trust me, little girl, you won’t like it one bit.”
Cynny wondered what the headmistress could be talking about. How could she force her to keep her bottom relaxed? She gulped and made her bottom go soft, even though she knew she would now feel the full sting of each smack of the sturdy implement. At least when she was punished with her clothes on, Miss Wickersham couldn’t tell when her bottom was tensed up. How would she ever survive twenty-two whacks on the bare without accidentally tensing up against the punishing blows? Her heart raced with nervousness.
Thwack! The first stroke fell, and Cynny cried out and felt her center jerk forward against the naughty seat as she involuntarily disobeyed the headmistress’s orders and shamefully clenched her cheeks. Oh no.
“Naughty girl.” Miss Wickersham tapped the ruler along Cynny’s thigh. “I will give you one more chance to keep that bottom soft and pliant for the remaining twenty-one strokes, but rest assured that if you clench up again, I will have no choice but to resort to more extreme measures to insure your cooperation.”
“I’m sorry, ma’am. I-I shall try, but it’s quite difficult.”
“Following rules is not always easy, little girl, but one of my young ladies should have enough restraint to behave herself on most occasions. Now, part your legs a bit wider and we shall continue. I certainly hope you refrain from clenching, lest I am forced to ask Cook to prepare a plug of ginger root for your little hiney hole.”
A what for her what?
Surely Cynny must have misheard Miss Wickersham.
She gasped and peered over her shoulder, preparing to ask the headmistress to repeat herself, but the ruler soon thwacked across her bare cheeks yet again. By some miracle, she managed not to clench during the unexpected blow. She immediately spread her legs a bit further apart as instructed, though she despaired over having her privates even more fully exposed.
Perhaps the added shame was part of her punishment.
Before she had time to ponder this, Miss Wickersham pressed harder on her lower back and brought the ruler down again and again, at least ten times in quick succession. Cynny tried to count the blows in her head, but the pain muddled her mind and left her so unable to focus, she could only concentrate on the fire that had been set ablaze on her bottom.
Then it happened.
Miss Wickersham gave her an especially hard smack, on the tender area of her behind where her thighs curved into her buttocks, and Cynny clenched her bottom.
She gasped loud as dread filled her.
Oh no. No no no.
What if she’d heard the headmistress correctly and the older woman did indeed plan to put ginger root in her bottom hole? Though Cynny couldn’t imagine how ginger root would keep her from clenching, the very idea of anything going in her bottom hole was embarrassing enough to bring tears to her eyes.
Miss Wickersham made a disappointed noise in her throat, followed by a scolding tsk sound that caused Cynny’s trepidation to deepen.
“Stay right there, young lady, and don’t you dare move. I will return shortly. If you so much as reach back and rub your bottom, even for a second, rest assured that I will find out and we will start your punishment over at stroke number one.”
The headmistress then departed the room in a quiet swish of skirts, leaving Cynny to her anxious thoughts. She sniffled and wiped at her fresh fallen tears, feeling absolutely wretched. Her bottom burned and she longed to rub out the throbbing sting, but she feared the moment she reached back to caress the globes of her backside, Miss Wickersham would return and catch her in the act.
Cynny concentrated on taking deep breaths and trying to calm herself. She tried to turn her mind off, because she could hardly stand the immense feelings of shame and guilt that were washing through her, along with the fear over whether or not Miss Wickersham really would insert something into her bottom hole.
But it was no use. Cynny couldn’t stop the tears, and she couldn’t quell the unwanted emotions rolling through her. She supposed she would have to endure. How she wished she’d been better. How she wished she’d been good enough to already have been matched with a papa. Then she wouldn’t be here right now, awaiting further punishment and worrying herself over whether or not her actions would endanger the reputation and financial standing of Talcott House.
Approaching footsteps and the swish of Miss Wickersham’s skirts prompted Cynny to look over her shoulder, dreadful curiosity curling in her stomach.
“Wh-what is that, ma’am?” Cynny asked, her gaze on a shiny cream colored object in the headmistress’s hand.
“This is a plug of ginger root, peeled and prepared for insertion into a naughty little girl’s bottom hole. I find it rather fitting that Cook got to prepare this for you, given the nature of your most recent infraction.”
Shock swirled through Cynny. She swallowed hard, not quite believing.
Did Miss Wickersham truly intend to put that…that thing…into her behind hole?
“Oh, please, ma’am! I’m so sorry!”
“No amount of pleading will sway me, little girl. This freshly carved ginger root is going into your hiney hole, whether you like it or not. Now, be a good girl and reach around to pull your bottom cheeks apart. Be sure to draw them nice and wide for me.”
It took a combination of scolding and encouragement from her guardian before Cynny finally complied and reached around to pull her cheeks wide for the ginger root. Her face burned as she did so, but at least she’d stopped crying. She was too surprised by what was transpiring to possess the energy for tears.
When Miss Wickersham first pressed the cool tip of the carved ginger root to her tight hole, Cynny let out a loud gasp, but the older woman ignored her slight squirming and her noises of protest and pushed the tip of the object inside her, breaching her snug passage.