Fucking My Best Friend in the Ass

Elle 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 tone outside my window. A scene as autumnal as a David Sylvian song. Inside was a different story. Our nude bodies drenched in the glow of hot pink and electric blue. 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 I 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 Elle’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 Elle 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 Elle’s. I’d eaten booty and fucked booty but had never brought the two together.

Brooke’s firm round booty, however, was a missed opportunity. We performed together often in the latter days of my entertainment agency’s decade and a half run. Including the times that she and Elle ate each other’s pussy. Giggling and moaning in playful sapphic pleasure while licking up each other’s sweet girl juices. I also fucked Brooke. 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 Elle’s pussy. And vice versa. Delivering the ultimate corporal punishment to each girl’s naughty bottom. Then having them suck my hot sticky cum out of each other’s tight asshole. Brooke’s life circumstances always seemed to cramp the style of our times together. That’s kind of on me. Not just with her, but with Elle 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.

Regardless, 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 Elle’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. Elle’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.

***

Spring was in the air six months later in mid-April when Elle invited me to join her poolside at her place one afternoon. It wasn’t quite warm enough for swimming with temperatures in the mid-70s, but the weather was perfect for nude sunbathing. One of our many shared interests that we were finally able to pursue together that day with her husband out of town. It was a gorgeous day. Not a cloud in the sky. Only an occasional slight breeze. The grass was already a lush shade of green with the trees well on their way. April is the month when red buckeye blooms. Livening the earth-toned landscape with random explosions of bright red. Various species of bird sang their respective songs. Large bumblebees floated from flower to flower. A male lizard performed push-ups on the fence. Attempting to attract a girl by impressing her with his feat of strength. My friend and I sunned our bare buns side by side. Lying next to her pool. Beach blankets providing a comfortable barrier between our naked bodies and the concrete underneath us. For a moment or two, at least, before we got down to business.

To be fair, Elle got plenty of sun on her buns. Lying on top of me in a sixty-nine. Deep throating my massive cock. Swirling her magic tongue around my head and shaft. Tracing every vein. Massaging every nerve ending in my frenulum. Lubricated with a combination of her saliva and my precum that wouldn’t stop flowing.

My mouth and tongue explored and savored every nanometer of her delicate pink pussy. Licking and sucking her swollen clit and lips. Tongue fucking her love canal. Devouring her sweet girl juices straight from her sugar walls. My attempts to consume every drop were in vain as my efforts only made her wetter and wetter. Drenching my face.

A movement in the distance catches my right eye. I spot what appears to be a woman watching us from the neighboring yard. Peeping at us from behind a large black oak tree.

“I think your neighbor is watching us.”

“Yeah, she often watches me sunbathe nude. She’s never said anything to anyone about it, so I guess she’s into seeing me naked. I don’t really know her, though. She seems really shy.”

“Maybe you should invite her over for a poolside sixty-nine.”

“I’d be into doing a poolside sixty-nine with her. She’s cute and has a hot body.”

Hearing about Elle’s sapphic desires and experiences always gets me even hotter. Because of course it does. Girl on girl is one of my favorite kinks. So is butt stuff. And that’s when I moved to Elle’s equally delicate pink asshole. Circling it with the tip of my tongue lubricated with my saliva and her pussy juices. She followed suit. Guiding my pelvis upward and thrusting her tongue in my ass. The neighbor continued watching as Elle and I had a contest to see who could tongue fuck the other’s butthole the deepest. My face buried in her crack. I pushed my tongue as far inside her tight puckered hole as possible. She did the same to me. Going as long as we could before having to come up for air. She rolled over beside me with a sassy expression on her face.

“I have Astroglide.” she informed me knowing that we only had one use for it since her pussy was always so fucking wet.

“I have some too,” I responded and thereby revealed my intention to revisit what we’d experienced the previous fall, “Let’s give your neighbor girl a show she’ll never forget.”

Elle got on all fours. I got on my knees behind her glorious booty. Slathering her cock hungry booty hole with a generous amount of Astroglide. Sliding one, two, and then three fingers inside her ass. Getting her all warmed up and slippery. I then coated my throbbing hard cock with lube, spread her firm round cheeks wide open, and leaned forward. The combination of being naked in the sun, our hot sixty-nine action, and the neighbor girl spying on us had Elle relaxed and ready to go. Her asshole practically swallowed my manhood whole. She badly wanted me to fuck her in the ass again. And having an audience, someone she was also interested in fucking, had her wasting no time. I leaned forward on her back. Kissing and licking her neck and shoulders. Playing with her nipples. Nibbling on her ear as I described what we were doing in the dirtiest rhetoric imaginable.

“My cock is deep inside your tight warm asshole, Elle.”

“Yes it is. I love you fucking me in the ass with your big hard cock. It feels so fucking good.”

“Your hot neighbor girl is watching me fuck you in the ass.”

“I know. I want her to watch. Maybe I can fuck her in the ass sometime.”

The thought of Elle buttfucking a woman with a strap-on had me going full throttle. Lifting myself off her back. Grabbing her bubble butt. I pumped her rump hard and fast. More Astroglide applied. I held her cheeks wide open. Watching my long swollen cock slide in and out of her tight pink butthole. Her pussy squirting hot juices all over my balls and thighs as she endured one intense orgasm after another. Our moans turned to screams as I got closer to shooting my load. Neighbor girl now just standing out in the open. Watching in shock and awe. I nearly motioned for her to come over and join us. But I thought better of putting her shyness on the spot. Besides, my focus in that moment was on hitting Elle’s backdoor spot. My cock was beginning its pre-ejaculation spasms.

“Cum in my mouth!”

Before I knew it, Elle had pulled her ass off my cock and spun around. She once again deep-throated me. Eyeing neighbor girl as she savored the taste of her asshole on my cock. Wanting the neighbor to see her do ass to mouth with me. I couldn’t hold back any longer. Releasing tidal waves of white hot cum in Elle’s mouth. All over her face and titties. She kissed me with searing passion. We shared the concentrated sweetness of our mingled carnal flavors. Then she turned and walked towards neighbor girl who was still watching us.

“Hey! Would you like to join us for a drink?”