This backdoor-pleasure virgin learns the sweet way exactly how erotic anal sex can be.

Fuck a woman in the ass? Why?

Up until recently, I considered myself that rare male who could honestly say he’d never thought seriously about anal sex. It wasn’t ever a possibility with the women I’d gone out with, and to me the idea just seemed… unnecessary. Why an asshole when a perfectly useful and desirable pussy was right there?

Then I met Brandi.

We had a mutual friend, Tim, a loud, monied guy who likes to host lavish parties. He has a place in the country, and I found myself free for the weekend when I received one of his coveted invitations.

“Come on, Johnny!” he bellowed cheerfully over the phone. “It’ll do you good to get away from the goddamn office. Good food, good liquor, good women. I promise — you’ll love it!”

When Tim says, “you’ll love it,” you want to love it. His enthusiasm is unstoppable.

I drove out on Saturday, deep into the rural environs. I stepped out of my car and paused to inhale the scents of pine and wildflowers. After the city, the quiet was soothing. It did feel good to get away.

Tim’s home consists of a main house, a big pool and patio, and outlying bungalows, the whole complex surrounded by untouched forested land. Guests were already on hand when I walked in. Tim bear-hugged me and threw me into the mix. He was grinning like a Roman emperor, directing people toward a buffet and bar. I snagged a cocktail and heard a splash from the pool. I turned around.

A stunning woman in a red bikini was backstroking the length of the pool. Her arms moved in a perfect clockwork, and her long toned legs kicked gracefully. I watched her every move, completely mesmerized. Her bared midriff was tight, with a dime-sized navel, and her firm breasts pushed against red fabric toward the cloudless afternoon sky. Was I being rude? I couldn’t stop myself from staring. Her skin had a coppery hue, with subtle golden undertones, and her long dark hair streamed over her shoulders as she cut an unerring course toward the end of the pool where I stood.

I thought she was beautiful even before she slowly and sensually emerged from the water, limbs dripping, hair sleek and straight. I let myself think for the first time that this weekend might be more than a simple getaway.

Before I could introduce myself, she fixed me with frank, dark eyes and said, “Hi there.”

“Hi. You were in last summer’s Olympics, right? Silvered for the two-hundred-meter freestyle, I believe.”

“I took the bronze,” she replied, running with my joke. “The Russian judge was an asshole.” She smiled one of those smiles that makes a woman look totally alive and aware.

“My name’s John.”

“I’m Brandi.”

We stayed close as the afternoon became evening, and she momentarily excused herself to change into a loose white top and denim skirt. We talked and grew comfortable with each other. I learned that Brandi ran a nonprofit that interacted often with Tim’s businesses. I told her about the legal work I’d done for Tim. But the shoptalk was only a cover. I tried some flirtatious banter, comments that could be tossed aside if they didn’t land. As she responded with an increasing warmth, I grew a bit bolder. She gave me that smile again, and a prickling of desire ran over my flesh. A few dozen people were still present as night settled in.

The food had been terrific, but by now even the vague formalities of eating were done. The get-together took on a Saturnalian vibe. The booze flowed liberally. Most of the guests had drifted onto the broad patio. The stars shone. The pool lights threw watery shadows everywhere.

I noticed two women lying side by side on a chaise longue. They faced each other, engaged in a long slow kiss. A man came up the steps at the pool’s shallow end, naked and grinning, his half-erect cock swinging.

I’d been to Tim’s parties before. They usually went this way after a while. Brandi stood at my elbow. I looked at her sidelong, a little leery of her reaction. Her lovely dark eyes were wide but full of a knowing mirth.

“Does this sort of thing bother you?” I asked.

“What — people enjoying themselves?”

“I mean, a bunch of adults behaving like skinny-dipping fools.”

“No. Does it trouble you, my suddenly prudish man?” Her hand curled around my arm, and she pulled closer to me. I very much liked the feel of her body against mine.

Tim’s roaring laugh came from somewhere inside the main house.

“Our host likes fun,” I said. “He likes happy guests.” It was true. Tim is always generous with his wealth and with the pleasures he can provide others.

“Are you… staying over?” Suddenly, Brandi’s face hovered quite near mine.

“I didn’t tell Tim one way or the other when I arrived. I didn’t arrange to stay overnight in one of the bungalows.” I nodded beyond the patio’s splashing shadows, to the small structures nestled at the edge of the woods.

Brandi’s fingers tightened on my arm. “I did,” she said, close enough to me that I felt the brush of her breath on my cheek.

We kissed. It was a simple lovely contact, and the act finalized what had been steadily building between us. The softness of her lips and firmness of her body enticed me.

More naked people were diving into the pool when we strolled together toward the quaint little outbuilding Tim had earlier assigned to Brandi. I had stayed over at Tim’s country place before and knew the layout. We went inside the bungalow, and Brandi fired up a single kerosene-burning lamp. It was a cozy enclosure, with bare beams crisscrossing a low ceiling. A sliding glass door gave onto a small back porch, beyond which stood the ghostly shapes of crowding trees. The furnishings were faux-rustic and very comfortable.

Brandi took my hand and led me toward the iron-framed, quilt-covered bed.

We sat on the edge. My heart quickened, but it was the delicious nervousness of discovery. I liked that we’d had time to chat. I felt I knew this woman, at least enough to recognize her as compassionate and intelligent, as well as extremely attractive.

When we kissed again, it was deeper, a probing of tongues. I put my arms around her. She ground her lips against mine, one hand grazing my cheek, then sliding around to my nape, grasping, her whole arm pulling me with surprising force. She drew me down on top of her, breaking our kiss. Her fast breaths made her breasts rise and fall beneath the loose top. Her teeth caught my lower lip playfully. I ran my fingers into her still slightly damp hair.

“I want you out of your fucking clothes!” she panted.

I was only taken aback for a second. Then she was helpfully tearing off my shirt and slacks. A physically active lifestyle has kept my body trim and toned. When my hard cock sprang into view, she growled with pleasure. She flung away her top, and I beheld her firm remarkable tits. A zipper gave a fast, tiny shriek, and her denim skirt went flying. She wore no panties. Her pussy glistened expectantly beneath a cropped dark triangle.

She spread her taut thighs. When I knelt between them, she seized my cock in her strong fist. The flickering lamplight brought out the richest golden hues from her bare skin. Her body was a drum-tight glory of well-used muscles and pleasing feminine curves.

“Fuck me good, John,” she begged. “Fuck me like I need it!”

Her words were an exciting cross between candor and sexual aggression. I felt a feral grin stretching my face as she guided my cock to her waiting hole.

I braced my hands on the pillows on either side of her head and thrust deep inside.

The clutching slippery heat shot pleasure all through me. My blood raced in my veins. I drove into her depths, drew out, plunged in again. Her athletic thighs clamped my flanks. She reached a hand around to sink her fingers into the flesh of my ass. She obviously didn’t want any slow, subtle buildup, so I pounded her. Fleshy smacks filled the snug room. The iron bedframe squealed. Brandi lifted her hips to meet my every downward lunge. The grip of her pussy was hot and fluid. I felt her trembling all over. She grabbed my ass with her other hand. Her face twisted with the intense exertion of extreme pleasure. I felt sweat dripping off me. Bliss simmered in my balls as they continued to slap her asscheeks.

About halfway toward my own climax, Brandi went into a joyful fit. She thrashed about on the bed’s quilt, breasts heaving, a wild cry tearing from her throat.

I rode her through an evidently drastic climax, slowing my thrusts and finally easing to a stop. I gazed down on her, feeling the satisfaction of any sensible man who has brought a woman to orgasm. Now I was assured she had gotten at least a share of the ecstasy that was her due. My own release wasn’t too far off.

I’d just started to move my fiercely hard cock inside her again when she abruptly wrenched herself away. I sat back and watched her roll over onto her knees, facing the wall. She stuck two fingers in her mouth, looked at me over her shoulder, and smeared the wet fingertips over the smooth pucker of her asshole. Her dark eyes were alight with a passionate fire.

“Put that big, fat cock in my ass!” she commanded. She gripped the headboard’s rail and stuck her gorgeously molded backside out toward me.

I blinked at her, feeling lost.

“What?”

A flicker of our earlier banter-fueled amusement came to her features. “You don’t know what I mean?”

I leaned back a little further. “I’ve just never done that.”

Brandi heard the honesty in my tone. Sympathy flashed across her face. She let go of the railing and turned. “It feels good, John. I don’t apologize for loving anal sex. I like to take a man into me where I feel most vulnerable, where it’s like he’s touching me in my most secret place. It’s a secret I like to share. I’d like to share it with you.”

I sat there on my haunches, clueless as to how to explain that I had never wanted to do a woman that way. This magnificent night felt like it was about to slip away from me. Brandi sensed my hesitation, but seemed to have thought of a solution. “If it’s strange for you,” she said brightly, “maybe you need some unfamiliar circumstances. You know, to take your mind off whatever’s got you so worked up.” She was plainly delighted with her idea. She bounced past me, vaulting off the bed to land by the sliding door. “I’ll go hide, and you come find me!”

With that, she flung the door open and hurled herself out into the night, leaping from the porch like a gazelle and disappearing immediately into the trees.

I stared. I gaped. I couldn’t believe what was happening. But I was still as hard as rock, and I wanted her desperately. After a moment’s hesitation, I went out into the night after her.

The day had been warm, but a stark country coolness had replaced it. I stepped off the porch, wincing as my bare soles touched the ground. The air chilled the sweat on my body. I took a few doubtful steps toward the trees.

What the hell was I doing? I was twenty-eight years old, a successful lawyer, and here I was playing hide-and-go-seek with a woman who wanted my dick up her ass. It was crazy.

Funny thing, though, the thought of doing that to her didn’t seem quite so shocking anymore. Maybe something in her rhapsodic soliloquy about the joys of anal sex had convinced me the act was worth trying. God knew I still wanted to fuck her, one way or the other.

I could feel that feral grin on my face again as I slipped in among the dark pine trees. I felt terribly exposed. Looking behind, I saw lights inside a couple of the other small bungalows, but already the woods were swallowing me. Starlight dripped silvery shadows onto my bare skin. Where had Brandi gone? How tough was she going to make this game, which I was now determined to win?

After bumping my knee and picking up a minor scratch or two, I stood still and listened. A breeze rustled the leaves. I heard a bird. But I also detected, off to my left, a tiny squeal of girlish laughter.

I moved carefully in that direction. I thought I heard someone’s fast excited breaths just ahead. Pressing quietly against a tree, I reached around either side of the trunk and seized two bare shoulders. Brandi yelped delightedly.

I stepped around the tree and found her in a clear shaft of moonlight. Her nude form was exquisite. In this setting, she looked like some mystical forest creature. Her dark cascading hair hid her face until she tilted her head up at me.

“I guess I’m it,” she said, voice husky with need.

I turned her around to face the tree. “Not yet you aren’t,” I said. Our hide-and-seek wasn’t over. This time I dabbed my fingers with spit and slicked up her waiting nether hole again. She shivered at my touch. She reached up and grabbed a branch in each hand, her sculpted ass thrust out toward me.

First, I swirled my cockhead around her ring. I knew that once I was inside her this way, I would be committing a sex act that was brand-new to me. A final flutter of nervousness went through me, but I told myself I was being an idiot.

I slipped my cockhead inside. Her pucker relaxed, seeming to suck me in. I fed her my inches, a little warily. She moaned, and the deeper I went, the louder she got. When my balls were finally flush against the tight curves of her ass, she cried out into the night, “I like you there, John!”

The angle was a little strange. Her channel had a forceful grip on me. I could feel the flex of unfamiliar interior muscles. But this no longer seemed a bizarre act to me.

I closed my hands around her hips and started stroking into her.

The heat inside her was intense. Her passage wasn’t as silky as her cunt. Yet it had a sort of rugged smoothness to it. I plunged in again and again, going slowly. There still seemed something fragile about the whole undertaking, and I moved cautiously.

But Brandi put that to rest by looking back at me, eyes blazing. “Fuck me harder! Fuck my ass like you mean it!”

I grinned, my fingers tightening over her hipbones. I gave her a merciless thrust, slamming her. She groaned with unmistakable rapture. Dark hair churned back and forth across her golden back as she whipped her head from side to side.

The cool air caressed our bodies, but sweat was streaming anew on me. I saw the sheen of Brandi’s flesh in the light shining through the branches. I was aware of how exposed we were, but that only added to the mounting excitement I was experiencing.

She wanted it hard, so I gave it to her that way. I planted my heels in the bare earth, toes gripping fallen leaves, and I hammered into her luscious little asshole. I drove to her ultimate depths each time. The taut halves of her ass rippled with the impact of my thrusts.

As I went at it, I realized that I now understood in some distant corner of my overheated mind what she had been talking about earlier. It felt like I was reaching her in a special place. I was penetrating to the essence of her. Here she was most vulnerable, and here she had invited me. She trusted me to bring her the specific pleasure she so craved.

I was connected to this beautiful woman, cock to ass, and the act was lovely and true and meaningful.

It was also some fan-fucking-tastic sex! I speared Brandi’s ass as she hung on to that tree for dear life. My cock blazed in and out of her, gripped by that sweet cinching ring. She was bucking back against me, taking me as deep as humanly possible, wanting as much of me as she could get. I accommodated her. I impaled her with every thrust.

Ecstasy was building in me. I meant to blast this woman’s defenseless interior with my hot, salty juice. As I hurtled recklessly toward that release, I felt my body awakening, crackling with carnal electricity. The length of my lunging cock was alive with delight. I had crossed over into a dark exotic land, and now it was time to leave my mark there.

My eyes rolled halfway up into my skull. A language-less cry came from my throat. I heard Brandi’s answering yowl scattering through the pines trees. A bird screeched nearby, and for all I know wolves fled the vicinity.

The deep joy took me and lifted me. When my first liquid jet hit, Brandi writhed like crazy, torquing still more delight from me. I spiked her hard with my cock, delivering my seed to her innermost reaches. I did as she’d told me: I fucked her ass like I meant it. Because I did mean it. The come I was pumping into her was the proof of my sincerity.

Each spurt rocked me. Heat rolled off the two of us in waves. I stayed joined to her vulnerable, but evidently very durable, passage as the last spasms of euphoria shook me. Eventually, my eyes rolled back down. I staggered back, disengaging, and watched my pearly fluid dribbling down the insides of Brandi’s thighs. She still hung onto the branches, knees giving way, her lovely body limp, spent. I heard her raw, soft sighing.

I stepped forward, turned her around, and enfolded her in my arms. Words were going to be useless for a while. She had no more cheerful obscenities for me. She huddled against my chest, and I felt the small kisses she dotted me with there. The night enveloped us and left us our tender moment of understanding and appreciation for this singular sexual act.

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