Tori was naked on my bed. Face down. Ass up. It was early afternoon but felt like dusk on that cloudy October day. She came over that morning. We’d spent the day licking, sucking, and fucking in every way imaginable. She’d been my cowgirl, missionary, and doggy as I fucked her tight wet pussy deep and hard. The gray skies blended with the orange landscape to deliver a dim sepia glow through the window. A scene as autumnal as a David Sylvian song. The crisp air that caressed our skin was cool. Not cool enough, however, to justify running the heater. This only served to heighten our senses. Our shared anticipation. Hearts racing. The excitement of what we knew was about to happen without speaking a word. Electricity flowed through my body while I squeezed her firm round cheeks. My cock ached with a kinky lust for life as a spread her cheeks open to reveal her pretty pink asshole.
An asshole prepared for what was about to occur. I had devoured it. My face buried in her crack. Between her glorious buns. My tongue circled the entrance to her forbidden love tunnel. Teased every delicate ridge. I licked her back and forth. Then pushed my tongue inside. An orgasm overtook each of us as I savored the warmth and sweetness of her delicious butthole. That an orifice exists ostensibly for utilitarian purposes only can also serve as the center of immense pleasures for both its owner and the individual exploring its nuances is a perfect metaphor for the proverb of life being what one makes it.
“The mind is its own place and in itself can make a heaven of hell or a hell of heaven.”
-John Milton
Or maybe a buttfucking is just a buttfucking,
I fucked her ass with my tongue then lubricated my middle finger in my mouth. Pushed my digit and spit inside her asshole. Her energy lit up every nerve ending in my hand. Smooth like velvet. Just like her pussy sans wave after wave of hot girl juices. I rubbed her clit with my other hand then fingered her pussy and ass simultaneously. Wave after wave of juices released. I was no stranger to pleasuring her ass with my tongue and fingers. This had been a staple of our play dates. Beginning with our second rendezvous when, while eating her pussy, I also ate her ass to her surprise and delight. I’ve long enjoyed eating girl booty. Inspired by all the instances I’ve seen in girl-on-girl porn. I wanted to eat Tori’s hot girl booty the instant I laid eyes on her. And I’ve done so countless times. My tongue going back and forth between her pussy and ass while she’s on top of me in a sixty-nine. Sucking her clit and tongue fucking her delicious soaking wet pussy while fingering her tight warm butthole. And she immediately enjoyed returning the favor with magical expertise.
Despite my enthusiasm for eating ass, I wasn’t that keen about fucking ass. Nor was Tori about being fucked in the ass. Each of us had reservations about the act based on our respective past experiences. To that point, I’d only done it with two girls. The two girlfriends I’d had in my life that I never liked. Why did I date women I didn’t like? Because this world is difficult for a pretty boy to navigate in his best interests. Anyway, both of these girls enjoyed getting buttfucked and I obliged them on occasion. The act itself with each was okay but not worth the effort to me. Both also left me sore due to the combination of my porn star-sized endowment with their excessive tightness. It might’ve been better had I been inspired to prep their backdoors like I did with Tori’s. I’d eaten booty and fucked booty but had never brought the two together.
But my buttfucking technique was on point thanks to my aforementioned anal sex adventures. Eighties music played as I applied a thick coating of Astroglide to Tori’s tight asshole and my raging cock. We trembled with anticipation. A dreamy atmosphere engulfed the world around us. I held her cheeks wide open, placed the head of my cock in the center of her pink hole, and leaned forward. Slowly. Gently. Ramming it in would’ve been painful for each of us. I allowed her the time she needed to relax and gradually open. To accept my entire manhood inside her. This also afforded us the opportunity to savor the moment when my cock entered her ass for the first time. I reached forward and rubbed her shoulders while she slowly pulled me inside her. Deeper and deeper. Neither of us said a word. Yet our bodies spoke volumes. I knew her asshole was velvety soft and smooth thanks to my tongue and fingers. But I had no idea just how soft and smooth she was until that moment. All the way in as she stretched wider and wider. Moaning and sighing with pleasure to assure me that all was well. My precum flowed like crazy inside her magnificent booty as her pussy soaked my balls with warm juices.
A ten-minute extended version of “Everybody Wants to Rule the World” floated through the brisk autumn air when I went fully inside her. My pelvis pressed tights against her bubble butt. I felt like I’d reached ten inches at this point. Okay, maybe not. But probably nine as I’m wont to achieve with her. We shared an orgasm over the sheer excitement of this new chapter in our friendship. I maintained the slow burn approach by thrusting slowly and gently. Only halfway in and out at first. Her asshole was so fucking tight. Clamping down hard on my shaft. Puckered as I slid in and out of her. Not wanting to let go of me. I added more Astroglide the instant I felt the slightest bit dry. I took longer and harder thrusts as she stretched further. It wasn’t long before I went from trying to get inside her to trying not to slip out of her. Fucking my best friend in the ass. And she fucked me back. Thrusting her booty back and forth. Riding my cock with her butthole. Hot for every inch deep inside her. Still communicating exclusively in body language. Booty language. She had been such an amazing friend from the start. Generous and nurturing in every way. And I repaid the favor in the most libertine fashion possible by fucking her in the ass. Showering her with dominance over her, protection from outside dangers, and ecstasy when I filled her warm tunnel full of white hot cum.
We took a quick break before going at it again in her pussy. Even tighter and wetter than earlier despite our marathon fuck session. Or because of it. Driven by the excitement of what had happened moments earlier. I had fucked my best friend in the ass. My cock went deep inside her tight butthole. It wasn’t quite as phenomenal as her pussy. Tori’s pussy is queen. But it was fucking amazing nonetheless. I was now addicted to fucking both of her warm love holes. Each its own unique temple of comfort and ecstasy. We finished off our play date by taking turns riding each other on top. I wrestled her down at the end for the victory. Holding her underneath me. Thrusting my aching and throbbing cock in and out of her sugar walls with reckless abandon. She squirted hot girl juices all over my balls and thighs as I exploded one last time deep inside her.
“I absolutely loved you fucking me in the ass, Stefan. My heart was beating so fast. Your cock felt so good deep in my butthole. It was because you were so gentle and went slow and easy. I should have tried it sooner. I loved being fucked in the ass by my best friend and the best lover I’ve ever had. It was very intimate. I felt really close to you. You made it special. It really did feel so exciting for my best friend to buttfuck me. I’m glad you fucked me in the ass.”
-Tori (paraphrased from text messages with her enthusiastic consent)
A new dimension was added to our friendship that day. We don’t call it a friendship with benefits. We are beautiful and confident people with high energy and zero shame. The pursuit of sexual pleasures together is a cornerstone of our friendship that goes without saying. It was clear from the start that we were meant to fuck the shit out of each other. A shared pursuit of hedonism. That day brought me closer to fully embracing the libertinism that has always burned deep within me. Something that I long struggled to let run wild and free due to the guilt trips I allowed others to send on me. A recurring theme in my memoir that I published the same week that I first buttfucked Tori. She features prominently throughout the final third of the book. A book that, in hindsight, is a testament to how I can never aim high enough. I’ve never been afraid to go above and beyond. To push the envelope further than most others would even dream. But I could’ve and should’ve pushed it much further. I’m better than most people, and I work at it constantly. If I can fuck a beautiful woman in the ass on a whim, then I can do anything.
I don’t have a professional-quality photo of Tori’s ass, so Brandi’s firm round booty is standing in as this post’s featured image. Brandi was one of my strippers during the final years of my agency and also appears frequently in my memoir’s back third. Including the times that she and Tori ate each other’s pussy. I also fucked Brandi. But not in the ass. I could’ve though. She confessed her love of buttfucking during a conversation on the highway late one night. I should’ve fucked her in the ass while she ate Tori’s pussy. And vice versa. Her life circumstances always seemed to cramp the style of our times together. That’s kind of on me. Not just with Brandi, but with Tori and everyone and everything else. All the times I let perfectionism get in my way. The time and energy I threw away on being considerate of people who weren’t worth the trouble. I know now how costly those mistakes have been.
That’s why I’m writing about fucking Tori in the ass five years to the month after the fact. Besides it being a totally hot fucking slice of creative nonfiction perfect for my website. It’s an event that occurred on the eve of both the end of my stripping career as knew it to that point and the world around me turning upside down in many ways. In that time, I subjected myself to a five-year plan so brutal that even Joseph Stalin would be put off by its harshness.
“Damn, that’s harsh.”
-Joseph Stalin (probably)
And I’m improved by the experience. Leaner and meaner than ever. My self-esteem and confidence in my abilities sky high. Problems in the past were far from being all my fault. But I could’ve dealt with them more effectively. But later is better than never. I’m still often overwhelmed by the sheer volume of mediocrity that surrounds me in every direction. But that’s no excuse. Not when I possess the gift of will to power. Nor when I’m capable of fucking hot women – even in the ass – at my leisure. And no, I no longer care about hurting the feelings of anyone who will never know such pleasures. Don’t like it? Then go fuck yourself in the ass. That’s life, and I’m also shut out from experiencing many things available to most people. I get finally get that, and now I’m ready to bend the world over and fuck her in the ass.
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