Training and the Second Time

 A few days after our first meeting, my phone buzzed with a message from Daddy.

Daddy: You were perfect last time, baby girl. But we both know we can make the next one even better.

Check your email.

I opened it to find an Amazon UK gift card for £30 and a link.

The link led to a set of three silicone butt plugs — small, medium, large — sleek black with flared bases and a subtle shimmer. The description called them “beginner-friendly training kit.”

His next message came almost immediately:

Daddy: Start with the smallest one tonight. Wear it for as long as you can every day. Work your way up. When you can comfortably take the medium for a couple of hours, message me. I want you ready for me next time. Be a good girl and train for Daddy.

My stomach flipped — equal parts nerves and excitement.

That night I locked my bedroom door, lubed the smallest plug generously, and after a few shaky attempts… it slipped in.

It felt strange at first — full, foreign, a quiet constant pressure — but not painful. I wore it for twenty minutes while watching TV, then longer the next day.

I scoured YouTube tutorials (on incognito, of course) and lurked on sissy Twitter accounts that gave surprisingly practical advice: breathe, relax the muscles, use more lube than you think you need, walk around the house to get used to it, don’t force it.

Two weeks passed in a secret blur of private rituals.

By the end of the second week, the medium-sized plug slid in with only a soft stretch and a sigh. I could wear it for nearly two hours while doing chores, reading, even a careful walk around the apartment when my roommates were out.

Each time I took it out, I felt a strange little pang of emptiness.

I sent Daddy a photo of the medium plug resting on my palm, my fingers still shiny with lube.

Me: I think I’m ready, Daddy.

Daddy: That’s my good girl. Meet me this Saturday? Same area. I’ll book us a quiet place.

We arranged to meet at a Costa Coffee — neutral, public, safe.

I arrived early, heart racing under my hoodie and jeans. He was already there, sitting at a corner table with two flat whites. When he saw me, his whole face softened.

“You look nervous again,” he teased gently after I sat.

“A little,” I admitted.

He reached across the table and squeezed my hand once, briefly. “We’ll go slow. You’ve done beautifully so far.”

We finished our coffees in comfortable quiet, then walked the short distance to a small, discreet bed and breakfast he’d booked. No grand hotel this time — just a cosy, private room with thick curtains and a surprisingly comfortable bed.

The moment the door closed, he handed me a small gift bag.

“For you.”

Inside: a soft black lace bra and matching panty set, and a brand-new tube of MAC lipstick in a perfect, classic pink — the kind that screams feminine.

“Go get ready for me, baby girl.”

I disappeared into the tiny bathroom.

I showered quickly, shaved again just to be smooth everywhere, slipped into the lingerie (the bra cups were lightly padded — they gave me the tiniest hint of a chest), and carefully applied the lipstick. I blotted, reapplied, checked the mirror.

The girl looking back at me had flushed cheeks and glossy pink lips. She looked… real.

When I stepped out, Daddy was already on the bed in just his boxers, watching me with quiet hunger.

I padded over and sat beside him, knees pressed together, suddenly shy again.

He didn’t speak at first.

He simply reached out, cupped both sides of my face with warm hands, and pulled me into the deepest, slowest kiss yet.

His lips were firm but gentle, tasting faintly of coffee. His beard scratched just enough to make me shiver. One hand slid to the back of my neck, holding me exactly where he wanted me, while the other drifted down my side, tracing the lace edge of the bra.

When he finally pulled back, his thumb brushed over my bottom lip, smearing the pink just a little.

“Look at you,” he murmured, voice rough with want. “All dressed up for Daddy… lipstick still perfect. You trained so well for me, didn’t you?”

I nodded, breathless.

“Show me,” he said softly. “Let me feel how ready you are.”

His hand slipped lower, patient, waiting for me to guide the pace this time.

And for the first time…

I wasn’t scared.

I was ready.