This is a sequel to ‘The Happiest Ending - Chapter 1: The Cost of Release’
The door opened with a soft click.
Warm light spilled across the hallway floor, and I blinked as my heels crossed the threshold. The room inside was small and quiet—low golden light, a faint scent of jasmine in the air, and a man sitting comfortably on the massage table, fully dressed, scrolling his phone.
Not Jake.
Definitely not Jake.
He looked up and smiled. Casual. Familiar. As if this were all completely normal.
I stopped.
Behind me, the masseuse—my "trainer"—gave me a gentle push on the lower back.
“Go on, sweetheart,” she whispered, too close to my ear. “He’s been waiting.”
The door shut softly behind us.
The man was already lying face-down on the massage table—bare except for the white towel draped across his hips. His broad back rose and fell slowly with each breath. He didn’t look up.
My heart sank. This wasn’t a prank. No one undresses for a practical joke.
My legs were locked in place by the heels and the panic. The tight pink teddy clung to my hips. The corset cinched me cruelly, high and firm. I couldn’t even remember how to stand naturally anymore. Everything about me was painted, perfumed, polished.
What if Jake really did set this up? What if there’s a camera? What if…
No. This isn’t a joke. There’s a naked man on the table. This is real.
I’m really going to have to touch him.
He’s going to expect me to make him cum.
I swallowed hard.
My trainer walked past me, grabbed a small bottle of massage oil, and handed it to me.
“Start with the shoulders. You’ll ease into it,” she said. “And remember… you’re here to please.”
I stepped forward, hesitant. My hands shook as I poured a little oil into my palm. It was warm—how was it already warm?—and smelled faintly of orange blossom and something deeper, muskier.
I placed my hands on his back.
He didn’t flinch. Didn’t comment. Just let out a long, low sigh of contentment.
Just touch. It’s just a massage. You can do this.
I rubbed slowly, awkwardly, sliding oil over his skin. I tried to remember what she did to me, circles at the shoulders, long downward strokes along the spine, but everything felt unnatural. My fingers were tense. I was hyper-aware of my body, of the teddy sliding between my cheeks, of the stockings pulling at the garter belt with every step I shifted.
“Relax your wrists,” my trainer murmured. She was behind me again. “Let your hands glide. Make him melt.”
I nodded stiffly.
After a minute or two, the man rolled onto his back. The towel stayed in place… for now.
His eyes met mine. He smirked.
“She’s nervous,” he said to my trainer.
“Of course she is. She’s new,” she purred. “But she’s eager.”
I tried to look anywhere but his face. Or the towel. I stared at the wall, the candles, the floor.
This has to be the worst dream I’ve ever had.
Except I’m hard again. God, why am I hard again?
My trainer came up beside me. She reached out and gently pulled the towel down.
He was already half hard. Thick. Heavy. My throat tightened.
“Go on,” she said. “He tipped ahead. He’s expecting full service.”
I shook my head slightly, my voice barely above a whisper. “I… I don’t know how.”
She smiled. Not kindly.
“That’s why I’m here.”
She reached for my hand, coated it in a bit more oil, and wrapped my fingers around his shaft.
Keep reading with a 7-day free trial
Subscribe to Pretty When You Kneel to keep reading this post and get 7 days of free access to the full post archives.