Yes

Before Mr. Weatherby can react, the thin material is in Bree’s shaky hands and she immediately proceeds to put the shirt over her head.

“I did it! I got my shirt! I didn’t lose!” Bree says aloud, only to be greeted by a playful, yet still firm spank on her tight tush.

“Well congratulations to you Ms. Bree, but you forget I still have your jeans and your bra here.” He says while dangling the bra over her head as if she was a child. Not that she did not look that part, her small frame standing in front of this large man, wearing only shoes, socks, and a shirt that comes only down to about an inch or two past her waste, leaving nothing below hidden from view.

“Well, yeah…” Bree’s voice trailed off. “I guess I owe you some penalties then, and one extra since I had to take of my shoes to get my socks back on.” Bree admitted.

“In time, but first, I did manage to catch you, so you know what that means.” Mr. Weatherby replied.

Bree had to think, technically she had gotten her last retrievable piece of clothing before being caught, but the game started when she left Mr. Weatherby’s office, so it should have also ended there right? That was the logic she was going by.

“Yeah I suppose you did catch me, so it’s only fair I hold up my end of the deal.”

With that, Bree dropped down on her butt, started taking off her shoes when Mr. Weatherby interrupted, “Far be it from me to tell you to stop, but what are you doing?”

“Well I said you know what happens if you catch me, and that was what happened last time, and I was naked last time wasn’t I?” Bree said with a nervous smile. She partly couldn’t believe she was willingly offering to get naked and suck Mr. Weatherby’s dick in the aisle of the school library.

“Good enough for me, proceed.”

And with the Bree stripped out of her once prized pieces of clothing.