Chapter 2: Panties and Close Shave

Continued from chapter 1:

“But Dolores,” I reply, ignoring her command to call her “miss.”

“I can't just let you spank me. I’m a grown man of 25 years old. And you were being a nosy busybody, not minding your own business. Are you sure you not the naughty one here?”

I meet her gaze, daring her to challenge me.

“Tell you what, why don’t we let chance and fate decide? I’m on my knees in front of you. For me to trust you with my discipline, I have to know that you can accept the roles being reversed if chance favors me over you.”

"What say you, Miss Maybourne? Will you play my game? If you win, I will give you my unconditional surrender and, with pleasure, take every bit of discipline you think I deserve…”

Her eyebrows shoot up in surprise at my audacious proposal, a slow, wicked grin spreading across her face.

"My, my, aren’t you a bold one? Very well, Ero. I accept your little wager."

Dolores leans forward, cupping my chin and forcing me to meet her piercing gaze in the mirror.

"But let me make one thing abundantly clear—I always win. Fate, chance, whatever you want to call it—it’s on my side."

She releases me abruptly, sitting back with a huff.

"However, I suppose I can indulge your childish desire for a game."

Reaching into a drawer of the nearby side table, Dolores produces a gleaming silver dollar.

"We’ll flip for it, nice and simple."

Chapter 2:

"Dolores, if I may propose an alternative. You seek to take me to task for what you call an unkempt lawn and mild disrespect. If I’m going to be spanked for it, I’d like it to be for something truly naughty—something that you would have **** but to light a fire into my bottom.”

“Here is the game I propose: Allow me to slide my hands up your skirt. Allow me to feel and grope you underneath your skirt. Allow me to have three chances to guess the color of your panties. If I cannot guess within three tries, I will surrender to you.”

“I will consent for you to undress me completely.I will consent for you to ‘trim my hedges,’ so to speak, and remove all pubic hair. I will consent for you to dress me in those panties you are wearing. I will consent for you to bend me over your lap in front of that full-length mirror and spank me with your hand and hairbrush until I am a sobbing wreck—a naughty little boy getting his just desserts.”

“And after I am properly chastised, I consent to you tying me to your bed, or whatever object you wish, and doing to me whatever nasty thing your heart desires. If I cannot guess the color of your panties, I am at your mercy and pleasure for as long as you wish to keep me there.”

“But if I can guess within three tries, I get to do all of these things to you... Dolores, do you agree to my terms?"

She stares at me for a long moment, her expression unreadable. Then, slowly, a smile spreads across her face—equal parts shocked, impressed, and utterly delighted by my brazen proposition.

"Well, well, well... Aren’t you just full of surprises?"

She drawls, uncrossing and recrossing her legs with deliberate slowness.

"You’ve got guts, I'll give you that much. Throwing down a gauntlet like that, offering up your body and dignity so freely…"

She stands abruptly, towering over my kneeling form.

"Guess away, my daring Ero."

Like a horny teenager stumbling upon his mother's underwear drawer, I slide my hands up Dolores's skirt and feel the delicious silk of her panty-bottom and sex. I almost cum right there. I run both hands over the enticing fabric, savoring my small victory. This woman has allowed me to grope her. Even if I lose, this is worth it.

"Dolores," I say with a confidence I don’t quite feel, "are you wearing pink panties today?"

She chuckles richly at my bold move, clearly enjoying the feeling of my hands roaming her silk-clad curves.

"Pink? Oh, you sweet summer child."

She reaches down and smacks my cheek lightly, almost affectionately.

"I assure you, my taste is far more... sophisticated than pastel hues."

Dolores grinds subtly against my touch, her breathing growing slightly heavier.

"Come now, Ero. Surely a strapping young man like yourself can do better than that."

She challenges with a wicked grin.

"You’ve got two more chances to impress me. Choose wisely—your future pleasure (or pain) depends on it."

I redouble my efforts. With one hand sliding over that tight heart-shaped bottom encased in satin, I take the other and place it between her legs. She gasps at my impudence, but she is warm, and she is wet with arousal.

"Black, Dolores. Your panties are red, aren't they?"

She gasps sharply, her breath hitching as my bold hand cups her most intimate area, feeling the damp heat radiating through the delicate fabric.

"Black?" she breathes, a deep flush creeping across her cheeks.

"Clever boy..."

Dolores subtly rocks her hips against my palm, seeking the friction she craves.

"Not quite. You're getting warmer... but still far from the truth and victory."

She reaches down, her fingers wrapping tightly around my wrist, guiding my hand to the lacy edge of her panties.

"Feel for yourself, Ero," she husks, her eyes holding mine in the mirror's reflection, a seductive challenge in them.

“Last chance. Don’t forget what happens if you lose…”

My mouth is dry, and I know my next guess will determine my fate—pleasure or pain. I rub her satin bottom as I try my hardest to make her cum. I slide my hand across the satin covering her sex, feeling the heat and wetness of her arousal. I rub her folds and caress her clitoris.

Her breath becomes ragged, and she whimpers before she aggressively removes my hands and backs away, flushed with arousal but eyes blazing in anger at what I almost made her do.

"Guess now, sonny Jim. Guess now and receive your comeuppance."

"Dolores," I say, voice trembling. "Are you wearing white panties?"

Panting softly, her chest heaving with barely contained arousal and outrage at my bold ministrations, she smooths down her rumpled skirt with shaking hands, trying to regain some semblance of composure.

"White?" She scoffs, a harsh bark of laughter escaping her lips.

"Oh, you foolish, presumptuous boy. Do you really think a woman of my refinement would settle for something so... pedestrian?"

Dolores stalks toward me, backing me up against the wall. She jabs a finger into my chest, her nail digging in painfully.

"Let me spell it out for you, since apparently subtle hints are wasted on you."

Her voice drips with icy disdain.

"I am wearing a pair of blood-red silk knickers, so dark they're nearly black. The kind that whisper secrets of sin and promise untold pleasures…"

My eyes water, and a single tear runs down my cheek. Why did I have to be so rude? Dolores in defeat is triumphant and terrifying. She is long and willowy, in her coral satin blouse and floral skirt. Grinning wickedly, she reaches under her skirt and slides the panties down her legs, setting them on the table next to me.

The blood-red silk whispers as it lands on the table, silky fabric that will soon be stretched across my bottom as she prepares to give me all the punishment I deserve.

"Well, well, young man,” Dolores lectures me sternly.

"Never in my life have I met someone so naughty and in need of a proper spanking. I don’t know what you were trying to accomplish here, but it looks like you’ve made a right mess of it.”

“You promised me quite a lot if I played your nasty little game and let you grope me, and you lost. Now, it’s time to pay up. What shall I do to you first?"

I swallow hard, trying to keep my voice steady.

"Undress me, Miss Maybourne. Undress me completely."

A wicked smirk plays at the corners of her mouth as she drinks in the sight of my distress, savoring it like the finest wine.

"Aww, is the poor baby going to cry?" she coos mockingly, reaching out to wipe away a tear with her thumb, smearing it across my cheek.

"Don’t worry, pet. By the time I’m done with you, tears will be the least of your concerns."

Dolores turns to retrieve the blood-red panties from the table, holding them up for my inspection.

"First things first—let’s get you out of these pesky clothes, shall we? Can’t have anything interfering with your... punishment."

She steps behind me, her nimble fingers making quick work of the buttons on my shirt.

"I must say, Ero, I’m quite looking forward to seeing what you’re hiding underneath all these layers."

Soon I am naked, a young man in my prime, standing before Dolores. She looks at me like a hungry predator, her eyes roving over my exposed flesh, drinking in every inch of my youthful physique.

"Mmmm, not bad at all, pet," she purrs, wrapping her long fingers around my hardening shaft, giving it a few teasing strokes.

"Such a pretty boy, all naked and **** before me. It's going to be a pleasure breaking you in."

I stand silent, tears of shame streaking down my cheeks. She grins wickedly,

"So, my dear, now that you are naked, what comes next?"

I take a deep breath,

"Please shave me, Miss Maybourne. Please shave my front side and backside until my privates and bottom hole are as bald as the day I was born."

Dolores' eyes light up with delight,

"Oh, I thought you'd never ask!"

She retrieves a vintage shaving kit from a nearby drawer, complete with a gleaming blade and badger hair brush. She gestures for me to lay face down on the large bath towel she's spread on her bed.

I obey, my heart pounding as I position myself on all fours, down on my elbows and knees. I can't help but tremble slightly as she spreads my cheeks, the cool air hitting my exposed flesh. She takes her time, applying the warm shaving cream with slow, sensual strokes, her touch sending shivers down my spine.

"Now, hold still, pet," she coos, picking up the razor.

I can see the blade glinting in the light, and a jolt of fear runs through me. She's got a blade near my sex, and I'm utterly at her mercy. The thought is terrifying, yet there's a dark, thrilling undercurrent that I can't ignore.

She starts at the top of my crack, pulling the skin taut with one hand as she guides the razor with the other. She works slowly, carefully, the razor scraping lightly as it removes the hair. I can feel every inch of the blade, cold and unyielding against my most intimate area. It's terrifying, yet exhilarating, a dance with danger that sends my heart racing.

She directs me to turn over, to lie on my back with my hands above my head and my legs spread wide. I comply, breath quickening into shallow gasps as she spreads warm cream across my chest. Her fingers are both soothing and firm as she begins at the base of my shaft, expertly stretching the delicate skin taut. As the razor glides upward, I feel the cool metal scrape against my skin, sending a thrilling shiver down my spine.

I hold my breath as she works, the fear and arousal mixing in a heady cocktail. She shaves around my penis, her touch sure and steady, then moves down to my balls. I can feel the cool metal against my sac, the razor scraping lightly as she removes the hair. I'm trembling now, the fear and excitement overwhelming.

Finally, she's done. I'm as bald as the day I was born, my skin smooth and sensitive to the touch. Dolores runs her hands over my freshly shaven flesh, a satisfied smile on her face.

"There now, pet," she purrs, "All clean and smooth, just the way I like it."

Setting aside the razor, Dolores circles around to stand in front of me, trailing a sharp-nailed finger down my chest.

Continued in chapter 3...