How about some backdoor action

You savor the feel of Jess’ mouth dancing around your body, while you consider your options. A nice blowjob, topped off with you cumming all over her face would be great viewing later on. Or maybe you could have her bounce up and down on your pole, cowgirl style. Then again, there would be nothing quite like the sight of her fingering herself for the camera.

But the more you think about it, the more you keep coming back to the same thing. The one thing you’ve always wanted to try, but never had the guts to suggest. The one thing Jess has hinted that she has no interest in. You always figured you’d never get the opportunity, but here you have an unprecedented chance. Of course, she might still say no, but this is the best chance you might ever get. You decide that you’d be a fool not to at least try.

“How about...” you say, pausing.

She looks into your eyes. “Anything you like. Just say it,” she coaxes.

“Ok... how about we... film me fucking your ass.”

She stops kissing you, and her jaw drops open. “Oh,” she says. She steps back from you, in shock, her hands absentmindedly rubbing her ass cheeks. “I didn’t expect... I mean, we’ve never... I didn’t even know...”

“That’s ok,” you say to her, disappointedly, “you can back out if you don’t want to do it.” You do your best to look sad.

“No- it’s not that,” she says. “I just wasn’t expecting that, and I don’t know if I can handle it. But I don’t want to back out- I mean, you wouldn’t back out if I had won the bet. A deal’s a deal. Tell you what, I’ll give it a try if you promise to be gentle, and to stop if I say stop.”

Damn. For anal sex you’d have promised her your right arm! You quickly nod your head in agreement.

“Where do you want me?” she asks.

“Just get down on the floor right there, in front of the couch. With your ass pointing toward the camera,” you direct her. “Good- now lean on the couch- rest your head on the pillow. Great. Now just stay there for a moment. I’ll be right back.” You leave her there, with her ass pointed toward the camera, while you run to the bathroom and grab a tube of KY jelly.

You adjust the camera, so it has a clear view of her ass, and her tiny pussy lips sticking out from between her legs. Then you get down on the floor next to her, and start rubbing and squeezing her ass cheeks. You start kissing her cheeks, slowly working your way to the center. Then you bury your face between her ass, and shove your tongue into her pussy. Jess may be nervous about this, but the abundance of juice flowing onto your tongue tells you she’s also turned on by the thought.

You suck her juices for a few moments, and then start licking your way up to her asshole. Your tongue teases her puckered eye, dancing all around it, and then just barely poking inside. She lets out a big sigh. Taking this as a sign of encouragement, you push your tongue in deeper.

“Ooooh!” she moans, pushing her ass back onto your face.

You reach for the KY, taking a glob on your fingers. “Reach back and spread your ass cheeks,” you tell her. She does as instructed, pulling her cheeks wide apart, exposing her ass and pussy to the camera. You take your lubricated fingers, and start rubbing around Jess’ anus. Her asshole twitches when the slick jelly first makes contact, giving you a rise in your crotch. Gently, you spread the lube all around her asshole, and then push one finger deep into her bowels. That finger is joined by a 2nd, and you do your best to stretch her out.

When you are sure that she is well lubricated, you stand up and grab the video camera, so you can film your cock sliding into her. You aim the camera down at your cock, while you spread the KY along your shaft. Then you get on your knees behind Jess, and aim your cock right at her anus. You take a moment to film her body, up to her head, which is turned to the side, eyes clenched shut, bracing for your cock.

“Ok babe. Here it goes. You ready?”