A very special lady

Wow, what a date. I was still an asshole virgin, and never thought I'd end it. I had been having darkly exciting thoughts, about having a girlfriend strap on a dildo, and bust my back door cherry, but working up the nerve to actually ask that? And here was an absolute knock out, female enough for me, who wanted to break me open with a real cock. I nodded, eager for her to take me up the ass.

She smiled, and told me to turn over. On my hands and knees, I felt her pull my cheeks apart, then the electrifying sensation as she applied her hot, wet tongue to my asshole. I growled with pleasure, the feel of her tongue teasing and running over the tight rim was nothing short of mind blowing. She brought a finger into play, and I could feel it push in to the first knuckle. I worked on relaxing the tight muscle ring, as she continued to lick and finger my asshole for a good long time. I could feel myself starting to relax more.

"Turn over Dennis, I slipped a valium into your drink, just something to relax you and make your virgin breaking a little easier," she whispered.

"Yeah, I'm ready for it Chantel" I whispered.

She smiled as slid a large pillow under my hips. I was lifted up, with my ass free of any obstruction, and I felt well greased fingers sliding slippery lube over my tight rim, then a finger worming its way in, spreading it around the tight walls. Chantel slid a coating of lube up her stiff cock, the lube making her erection gleam in the dim light.

"Grab behind your knees, and pull them towards your chest."

I did so, feeling my asshole spread apart slightly, ready for her cock. She got into position, her legs straddling the pillow, pushing another, smaller pillow under my ass to raise it up for the right level, setting my ass up for cornholing. I could feel her lubed up cock head pressing against me.

"Now, just relax baby, you'll love it" Chantel whispered huskily, "I'll bust your cherry gently."