Upsize

I stood there with my pants still down, the shiny bejeweled plug firmly seated in my ass, and looked around the room.

“Fine,” I said. “I will agree to upsize. But only if everyone else tries a small one first. Guys and girls. Let us see who can handle it.”

The group erupted in excited chatter. The girls were surprisingly eager. Mia grinned and pulled out a selection of smaller plugs.

“Deal,” she said. “But you go first with the bigger one.”I bent over the coffee table again, ass up. Mia lubed up a significantly thicker plug and pressed it against my hole. She worked it in slowly, twisting and pushing until the widest part stretched me open. I groaned loudly as it popped inside me. My ass clenched hard around the thick base, pressing firmly against my prostate.

“Fuck, that is big,” I moaned, my cock leaking onto the floor.The girls cheered and took turns gently fucking me with the plug, pushing it in and out while I stroked my cock. The stimulation on my prostate was intense. Every thrust made my cock throb and drip.Then it was their turn. The girls went first. Sarah took a small pink plug and bent over. I helped push it into her tight ass while she moaned. Lena took one next, gasping as it popped inside her. Emma and the others followed, each taking a small plug with varying degrees of pleasure and discomfort.

The guys were more reluctant but the girls pressured them. Jake took a small one, wincing as I pushed it into his ass. Tyler and Chris followed, each of them moaning as their asses were filled for the first time.Now that everyone had something in their ass, the real fun began.Mia made me bend over again. “Time to see how much you can really take.”She switched me to an even bigger plug. This one was thick and heavy. She lubed it generously and worked it into my stretched hole. I groaned deeply as it forced me open wider than before. The pressure on my prostate was overwhelming. My cock was rock hard and leaking steadily.

The girls took turns playing with the plug, fucking me with it while I moaned like a whore. Sarah stroked my cock while Mia pushed the big plug in and out. The combination was too much. I came hard, shooting thick ropes of cum all over the floor while my ass clenched around the massive plug.

The night turned into a full anal training session. Everyone took turns fucking each other with plugs and dildos. The room filled with moans and the sounds of lubed toys sliding in and out of asses. I ended up on my back with the biggest plug buried deep inside me while the girls took turns riding my cock.I had never felt more exposed.Or more satisfied.