We arrived at the resort in the early evening, with just enough light left to get a glimpse of some of the buildings and facilities. After check-in we were taken on a short tour and then shown to our room. It was spacious and well appointed, with large glass windows looking out onto the private beach.
I slid the glass doors open to bring in the scent of the ocean and listen to the waves crash onto the shore. It was warm and humid, but pleasant. I opened my suitcase and retrieved a bottle of wine and a bottle of scotch. Searching through the small kitchen I found glasses and poured one of each, a double shot for him. Handing him a glass, we stepped out onto the patio to enjoy the sunset.
"Drink up, you'll need this," I said, pulling my necklace out from underneath my shirt. He was used to seeing this necklace, but not with a second larger key hanging from it.
With a cocky chuckle he commented, "so, what's this about?" eyeing the keys. I grinned at him without reply, sipping my wine then turning my attention to the pink and purple hues hanging over the ocean as the sun bid us goodnight.
It got dark quickly, and we moved inside. "Did you pack properly?" I asked.
I was pleased to see that he had followed my instructions to pack one bag with his clothes, and another with toiletries and his assortment of toys and leather.
"It's time for you to strip now," I said.
He complied with a smile, but his face soon began to show concern as I gathered up those clothes and placed them in his luggage, removing my necklace. His eyes got wide as I placed the suitcase in a wardrobe cabinet, closed the door, and locked it. "You will get these back when I say you can," I told him.
He looked down into his empty glass and back up at me. "One more, please Mistress," he asked. I allowed him to pour himself another drink but took it from him. I sat on the edge of a chair and lifted my skirt, revealing my bare pussy. "You can only drink that after you've drank me. And you can not touch yourself anywhere at any time."
He got on his knees and lifted my legs over his shoulders, burying his face in me. His lips and tongue went to work and soon his face was wet with cum. "You're almost ready," I told him. "Kneel across the chair."
He knew what was going to happen, but the first strike of the paddle still made his body jolt. I started with small light swats but quickly worked up to hard stinging licks. Once his ass was fully reddened and burning I allowed him to have his drink, which he downed in one shot.
Walking to his bag that had not been locked away, I retrieved a cockring and collar. I reached into my bag and pulled out a leather and metal leash, attaching it to the ring on his collar. Handing them to him, he knew what to do, shaking his head with excited anticipation and fright at what he was about to be subjected to. I retrieved a smaller bag and was ready to go.
"I'm going to parade you through this place naked and well spanked, on display for everyone to see," I told him, tugging the leash and leading him out of the room into a breezeway.
He had fantasized about being stripped and displayed publicly, but now that it was becoming reality he felt overwhelmed by the mix of excitement and fear.