Every Friday, Kenny and I have “Anything Goes Night”.

That’s when we cut loose and do whatever we want without worrying about the consequences. We don’t count calories or worry about getting drunk and having to wake up on time the next day. Basically, we give ourselves a night off from reality.

Most of the time, we use our “wild” nights off to stay up late binge-watching TV shows or scaring the crap out of ourselves with our favorite horror movies. Now and then we’ll go to a club to see one of our favorite DJs spin late into the night, or we’ll go to a concert and dance and drink until we’re ready to fall straight into bed when we get home.

But once in awhile, we use our big nights to have no-holds-barred sex. Sometimes we go for kink, sometimes we try to change up the location of our lovemaking, and sometimes we try something new. Last week, we opted for anal.

We’d been gearing up for it slowly, over a number of weeks. Kenny had started months earlier by running his finger around my sphincter, lightly teasing me and warming me up to the idea of backdoor play.

At first I was shocked. But once I could lay there and feel him touch that sensitive part of me without jumping, he began to ease his finger inside with the help of lots of lube. The initial entry into my ass was a little daunting because I was so tense, but I took a deep breath and relaxed, letting his fingertip inside. Once I let go of my nervousness, I realized that it actually felt really good. I liked feeling his finger inside me, and I wanted more. I was suddenly in a rush, but Kenny still took his time, not wanting us to go too fast, too soon. Every few days, he’d inch more of his digit into me as we played until I could take his forefinger right up to the bottom knuckle without any problems.

When I was comfortable with finger-banging, we moved on to butt plugs. We researched them extensively and bought a series of toys, each one larger in size. The smallest was slightly thicker than his finger and the biggest was nearly the size of his dick. And every week we played with a new plug, selecting the next largest in our collection. Having him prepare my ass to take the toy was dirty, good foreplay. By the time the plug was stretching and filling my asshole, I was raring to fuck. In the back of my mind, I knew we were ultimately preparing me to take his dick in my ass, which excited me to no end.

The big event came last Friday, when “Anything Goes” became “Everything Anal.” We’d been prepping for so long that whatever trepidation I’d felt at the beginning of our experiment had disappeared, and now all I felt was excitement and arousal. I remembered every jolt of joy I’d felt as a butt plug was pushed between my cheeks or pulled slowly out of my ass, and all the pleasure I’d experienced as Kenny wiggled a finger into my tight rear entrance. And now, I was ready for the real thing.

The night started like any other evening of lovemaking, with lots of kissing, touching, and caressing. Kenny whispered sweet nothings into my ear as he undressed me, and he told me how sexy he found my new lingerie. I’d bought the set just for that night, to highlight my desires. The panties showed off my ass with a heart-shaped cutout on the butt. We explored every inch of each other’s body as we worked up to the main event.

Kenny fucked my pussy first, to get me really in the mood. Having his cock buried between my thighs only made me want him buried in my ass that much more. It was the perfect precursor.

After I’d had a long, hard climax and felt totally relaxed, Kenny pulled out, lifted my legs up so my knees rested over his shoulders, and began to ease his lubed dick into my butt. Even though we’d been preparing for that night for so long, nothing could have prepared me for how excited I’d feel once my boyfriend’s cockhead was pressing against my sphincter, begging for entrance to my behind.

As Kenny eased more of his cock into my ass, he kept his eyes locked on mine. He kept checking to make sure I was okay and was enjoying myself. Not that he needed to ask — the massive smile on my face, which was making my cheeks ache, definitely gave me away.

He took his time penetrating me, but every inch felt better than the last as he eased his cock into me. Once he was fully enveloped between my cheeks, and once I gave the go-ahead, he started to thrust.

I was open and ready and begged him to pick up the pace. I wasn’t ready for hardcore fucking, but I wanted a little speed, a little force, and Kenny gave me just what I was hoping for. He stroked in and out, in and out, moving faster each time, until he was fucking my ass at a good, steady pace.

It was heaven! I didn’t think I’d like the first time, but it was everything I wanted and more. I already knew that I wanted Kenny’s cock in my ass on the regular. I wanted him to drill my ass even more than I wanted him to do my pussy. Maybe it was because we’d been preparing for the big moment for so long, or maybe I’m just a “butt slut,” as Kenny has taken to calling me, but from that moment on I was a convert.

I begged Kenny to keep going; he’d worked up to the perfect pace, making my arousal skyrocket. As always, he didn’t disappoint. He kept at it, stroking in and out at exactly the speed I craved. The longer he pumped, the more pleasure I felt, until I felt the telltale tingles that signaled an impending orgasm. I wasn’t far from climaxing, and I was desperate to get there. I reached between my legs to find my pussy sloppy-wet, and I stroked my clit erratically as Kenny continued to plunder my behind.

I clenched my cheeks to add more pressure, like I sometimes did with the butt plugs, and Kenny moaned loudly at the sensation. He kept pumping, shortening his thrusts and banging me with a staccato rhythm. It only took ten or twelve strokes like that before I let go and my body shook as my orgasm hit.

Kenny wasn’t far behind, the orgasmic spasms of my asshole no doubt inspiring him. He shot the first load into my ass, then pulled out and fired the rest of his load onto my stomach, letting me see how much he enjoyed our new favorite sexual pastime.

We lay in bed for a while afterward and discussed everything we’d done, our own sexual post-mortem. Kenny asked me if I’d enjoyed myself, and I giggled as I told him yes, though I knew the answer was obvious. And I asked him if he enjoyed himself, too, and he, of course, said he had. Then he asked if I wanted to do it again, and when I said, “Absolutely! Let’s go!” he laughed.

"Not now,” he said, amused. “I meant in general.”

"Oh.” I was, I have to admit, a little disappointed. I was already addicted.

Kenny told me not to worry, he just needed some time to rebound and he’d be ready for another go. “In the meantime, why don’t we get some rest,” he suggested. “Maybe discuss what you want to do next Friday.”

I already knew what I wanted to do — and what I’ll want to do for the next few Fridays at least. But I was willing to play along. After all, I had a feeling our newest Friday activity was soon going to be part of our everyday lives, too.

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