My face was comfortable in the pile of pillows. My bottom was in the air with both holes exposed. I heard him pump the lube and make an attempt to warm it with his breath. He slathered it on me and the metal plug.
“Relax,” he said.
It was my first time. I felt pressure against my ass. I cried out and tightened up. The feeling wasn’t bad, but I wanted to go slow.
“Unnhhh… I feel it,” I said.
“You’re going to feel it. Relax and it’ll be easier,” he said.
The pressure didn’t go away. I couldn’t take my mind off of it. He stood up and opened the door. He flagged down a girl named Jamie. I didn’t know Jamie, but Jamie knew him. He leaned my head back down.
“Let’s try again” He started moving the tip of the plug in small circles around my hole. That felt like a much better way to warm-up. When he began to ease the plug in, I felt Jamie’s tongue in my pussy. She caught my cunt by surprise. Her tongue flicked and played on my clit.
“Bite it, and I’ll cum” I was working very hard not to climax.
“Bite it,” he said.
Jamie bit down on my clit. He popped the plug into my asshole and held it there while my juice leaked out of me. Mostly, Jamie got it in the face.
When the plug was finally in, I didn’t mind so much. It felt odd, heavy. I felt a little horny.
“See, it wasn’t that bad.” he said.
I looked up at him inquired casually…
“Can Jamie be there when we take it out?”