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Chapter 5
by
ErosApostasia
What's next?
Chapter 5: “Panties? You naughty boy.”
Continued from chapter 4:
“Are you going to make me ask for it?” I whisper.
She rises slowly from her chair. Then she walks around the desk toward me. Every movement is deliberate. Measured. When she finally stops in front of me, she braces both palms against the desk and leans down until we are eye level.
Her brown eyes search mine carefully.
“I am,” she says softly.
My pulse hammers.
“At least this first time.”
Her voice remains calm and reassuring.
“I need you to say the words because I need to know you truly want this.”
Chapter 5:
She lifts one hand and gently cups my cheek.
The touch is impossibly tender.
“You’ve spent years hiding this part of yourself,” she says. “Letting someone see you like this is scary.”
Her thumb brushes slowly across my skin.
“But you don’t have to hide from me.”
Emotion surges painfully into my throat.
“I want to guide you through this carefully,” she whispers.
Tears begin stinging unexpectedly behind my eyes. The ruler taps softly against her palm. Expectantly. Patiently. I finally break.
“Becky,” I whisper shakily. “Miss Winthrop...”
She waits.
“Please.”
The word catches in my throat.
“Please spank me.”
The humiliation of saying it aloud sends tears spilling free despite my efforts to stop them.
“I need it,” I admit. “I need someone stronger than me sometimes.”
Becky’s entire expression softens.
“Oh, Ero.”
She sets the ruler aside immediately and wipes gently beneath my eyes with her fingertips.
“There’s nothing pathetic about trust,” she says quietly.
Her voice carries no mockery.
Only warmth.
Only care.
“I’ve got you.”
She helps me stand carefully before guiding me toward the large desk against the wall. My knees feel weak. My entire body burns with humiliation and anticipation. I am thirty-eight years old. I run a company.
And yet I tremble beneath the guidance of my twenty-four-year-old secretary as though she has somehow reached directly inside me and found every hidden insecurity I have spent years concealing.
Becky rests one hand against the small of my back.
“Breathe for me,” she says softly.
I obey instinctively.
“There you go.”
Her tone remains soothing.
Grounding.
“Nothing bad is happening,” she murmurs. “You’re safe with me.”
My breath catches as she begins carefully undoing my belt. The metallic sound of the buckle seems deafening in the quiet office. She moves slowly, giving me every opportunity to stop. But I do not.
Instead, I grip the edge of the desk and bow my head.
“You’re doing well,” Becky whispers.
Her encouragement only deepens the emotional ache in my chest. When my trousers slide downward, another wave of embarrassment crashes through me.
Becky pauses. Then a startled little laugh escapes her. I close my eyes immediately. Of course she notices the panties. I had forgotten I was wearing them. Smooth silver satin with delicate ruffled trim.
God. I want the floor to open beneath me.
Becky covers her mouth briefly, trying not to laugh too hard.
“Ero,” she says softly.
Her dark eyes widen, and then a delighted laugh slips past her lips.
“Oooh,” she murmurs teasingly. “Panties, Ero? You naughty boy.”
I groan and bury my face against my folded arms, every muscle in my body tightening with embarrassment as she takes in the sight of me.
There is surprise in her voice. But no cruelty. No disgust.
“You really have been carrying all of this alone, haven’t you?”
My face burns.
“I’m sorry,” I mutter.
“No.”
Her answer comes instantly.
“Don’t apologize.”
She steps closer behind me.
The warmth of her body radiates gently against my back.
“There is absolutely nothing wrong with vulnerability,” she says.
Her hand glides slowly across my satin-clad bottom in a reassuring caress.
“And for what it’s worth,” she adds quietly, “I think trusting someone enough to show them this side of yourself is actually very brave.”
Emotion swells painfully in my chest again. Becky lets her palm rest warmly against my panties for a long moment before speaking once more.
“I’m going to start gently,” she says. “No surprises. No pushing you too far.”
Her voice becomes calm and authoritative again.
“I want you relaxed. I want you listening to me.”
To be continued in chapter 6...

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Discipline and Accountability
Chapter 1
Ero confesses to his new secretary that he needs discipline in his life, and she holds him accountable...
Updated on Jun 11, 2026
by ErosApostasia
Created on May 27, 2026
by ErosApostasia
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