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First Backdoor Threesome

Category: Anal Sex
25.10.2024
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I’d been to the July 4th parade every year for over ten years, but this was the first time I was alone. My kids had all left, and before that, my wife. Where they went, or why, wasn’t on my mind. What I felt was alone.

When my kids were younger, the parade meant fire trucks, horses, old cars, marching bands, maybe even an army tank or troop carrier. I never used to pay much attention, since I had to keep an eye on the kids.

This year, I watched the ladies, straddling their horses, and let myself imagine I was their stallion. Or the high school band baton twirlers, smiling teens in short pleated dresses, unafraid to kick up their legs. I even had one smile at me as I leered at her body. She kicked extra high, just for me, showing off lots of pure white frills to fill my fantasies. When her eyes met mine, we smiled at one another. She was safe, in the street, with all those eyes watching her. She gave me a wink. I shook my head. “Down, boy,” I said under my breath.

And there were the farm animals, never embarrassed about shitting or pissing right there in front of everybody. I was always watching for an tail lifting, herald of a bowel movement. There was something that stirred in me as I watched the bulbs of manure pop from a horses asshole. I had always liked taking a shit, the feel of it. I wished I had the freedom to be able to do what I felt like doing, when I felt like doing it.

A mare swished her tail, took a couple sideways steps, bumping against the horse beside her. I could tell she was in heat when she winked her large clitoris out then in, the bright pink of her vagina bringing me to attention. What I wouldn’t give to be a stallion, running on the hills, fucking all the mares, filling them with my contribution to the gene pool!

Everything was there, in the parade: the girls, the boys (soldiers in neat uniforms ready to do their duty). And especially the result of their union: all the children. So many cute kids! Cute, as long as they were somebody else’s kids! I laughed as a truck full of lambs rolled by, lots of little kids dressed up as lambs!

That was when I noticed her, across the street. She had laughed, too, at the little lambs. And when I saw her, she saw me. We both smiled, looked away, then looked back. This made us both smile, again. She was in her 30’s, nice body (not so skinny as those high school girls). Her hair was red, not the bright red, but a soft red, short, cute. It looked like she had green eyes.

But what kept my attention most was her smile, and the way her eyes smiled, too. She wasn’t hurt or damaged like so many of the women I had dated. You know, women who are unable to relax, unable to be relaxed with themselves. This redhead looked like she knew exactly who she was, and she knew she liked smiling at me.

I looked up and down the parade for an opening to cross the street. I chose to weave my way through a collection of grade-school kids and their parents carrying an advertisement for a local private academy. I saw that redhead moving, going into a store. Careful not to knock anybody down, I made it across the parade, picked my way through the packed-solid row of kids sitting on the curb, then up to the sidewalk and into the store.

It was a nick-knack store, second-hand stuff that reminded me of my mother’s house. The redhead walked behind the counter, then turned and watched me as I came up. I didn’t respect the line that kept the customers at bay, and walked behind the counter, then behind her. She stayed, didn’t move. I put myself behind her, pressed my body into hers and whispered.

“You have a back room? Someplace more private?”

With my lips tickling her ear, she tilted her head, pressing her ear into my lips. She turned her head towards me, giving me more access to her ear. I slid in my tongue. I felt her body shiver. My hand came up to rest on her buttocks, then carefully scrunched up the material that was her dress, until I had lifted it high enough to get my fingers between her thighs.

She pressed her cheek into my face, jerked as my fingers slid under her thong, becoming slippery as I pressed forward and found her juicy slit.

“Excuse me…”

We both stopped and straightened up. I leaned back, letting the dress fall. We turned to face the elderly lady across the counter.

“Sorry to interrupt you two lovebirds,” she said, grinning. “But could you tell me how much this knob is?”

The redhead smiled, turned to me, gave me a kiss.

“Come back at five,” she said, then added, “sweetheart.”

I smiled back, gave her a pinch on the butt, making sure the old lady could see.

“See you at five, love bug,” I said. I turned to the old lady. “What you doing ’til five?”

The old lady giggled, then caught herself when she saw I was waiting for her answer. She looked from me to the redhead.

“It’s okay with me,” the redhead said, shrugging her shoulders. “But be careful,” she whispered, “he bites!”

The old lady giggled, this time nervous. “No. No, thank you,” she said, took a quick look from one to the other. “No… Oh my, no!” She blushed, then walked away.

“Five it is,” I said.

I turned one last time as I left, and the redhead blew me a kiss.

I looked at my watch. It was a little after 2pm. I went home, took a bath, got ready for some play.

I enjoyed a good, natural fuck as much as the next man, but over the years, I’d come to enjoy a little anal play, too. I had a feeling my redhead knew how to handle a man’s asshole. I imagined that she might even know how to finger massage my prostrate. So I voided my rectum (a warm water enema with extra mild soap), stretched myself (an especially giant butt plug that took several weeks for me to accommodate), then I oiled up, inside and out. You might think this was a bit extreme, just for a good fuck with a hot redhead. But I must say that somewhere, in my deepest darkest hidden corners of my imagination, I hoped someday, something bigger than a woman’s finger would find its way into my carefully prepared love nest. And I got excited being ready, being open, to the experience. Besides, there weren’t many women that could resist my asshole, once they knew what good shape I kept it in.

Five o’clock came up fast. I headed back downtown and walked into the little shop at just five minutes to. The redhead was there and smiled when I came in the door.

“We’re closing,” she announced, and the two couples that were wandering around the stacks of stuff wandered towards the front of the shop. I watched her follow them, herding them out the door. She closed and locked it, then turned the sign so that it said CLOSED to the folks outside. She looked at the sign, the side that was facing inside, and smiled.

“I’m OPEN for you,” she said.

She took me by the hand and led me to the back of the store, through a door that went upstairs, through a hallway, to a door on the left. She pulled me inside and closed the door behind us.

It was dark. There was a small light hanging from the ceiling that only lit up a little of the floor underneath. There was a mattress, no bed, just a mattress. She pulled me into the light and started taking off my clothes. She attached her lips to mine and I felt her tongue swirl around as her hands undid my belt.

I worked as fast as I could: her shirt, her dress, her bra, her thong, all while her tongue danced in my mouth. Her hands climbed up, then down my back. She pulled me onto the mattress, slipped off my shoes, my socks, my pants, crawled between my legs and gave my engorged cock a quick suck. She turned onto her back, wiggled underneath me, and tugged me down on top of her.

She rocked her hips up and as I lowered myself onto her smooth skin, I was inside her sopping cunt with one, easy thrust.

She gasped, then groaned, which set me to pounding her hard and fast. She responded, lifting her legs around my waist, letting me go deeper. I nipped at her swollen breasts and sucked at her hardened nipples, rolling them in my mouth, pressing them with my tongue against the back side of my teeth. She began to shake and bounce. Each of my thrusts caused her to cry out.

I was getting where I wanted to be real fast, felt the growing pressure. She dropped her legs, left them splayed wide, and grabbed my butt. She sank her fingernails, carving their initials into my flesh. I felt her fingers grasp and spread my ass cheeks. I felt the skin tighten around my rim. I wanted her fingers inside.

“Yes, yes…,” I groaned.

Then I froze. I had heard something. It was a sound from the corner. I jerked my head to look over my shoulder. I could make out the outline of someone, sitting in a chair. I had heard a man groan, groan like he was jerking himself off in the corner.

“What the fuck!”

The redhead held me tight, didn’t let me get up.

“It’s okay, it’s okay,” she said, trying to keep me inside her, even as my cock shriveled. “It’s my husband,” she whispered. “He likes to watch. Don’t stop. Don’t stop…”

“It’s okay,” she repeated, and rocked her pelvis. She pressed my butt into her. I continued to watch over my shoulder. The husband didn’t move, didn’t make a sound. The redhead kept up with the rubbing: wet, soft, hot. I started to get a hard-on.

“Yes, yes,” the redhead whispered.

Slowly, I turned back to her. I started to rock with her, to press into her. My cock grew, then stiffened enough to pop into her. Soon it had grown back to full size and now filled her.

“That feels so good,” she hissed.

It did feel good, and we rocked together. But I couldn’t get the husband out of my mind. I couldn’t stop thinking about him in the corner, watching me, as I pumped my cock into his wife’s cunt.

Then I became aware of a different feeling, a want, a tickle that needed to be scratched. But the tickle wasn’t coming from my dick. It was coming from my ass. I thought about that man, sitting in the corner. He didn’t want to fuck his own wife, preferred watching another man fuck his own wife. Maybe he wanted something else, something different. I felt my sphincter relax, anticipating.

Even as I moved in and out of the wife, I found myself imagining that I was being penetrated by the husband. I became deliciously aware of the man in the corner. He had a perfect view of his wife’s crotch, and my cock in her cunt. But what I found most exciting was thinking he was looking at my ass, my open and ready butt hole.

Even though I had never been with a man, could only imagine what it would be like, I often fantasized about a cock up my ass, penetrating, massaging. I had even bought a rubbery dildo, a huge fake dick, and pumped it inside me, slid that big rod in and out, all the way in, feeling it against my prostrate, wondering if I could have an orgasm from a man fucking me.

I began to shake as my body reacted to what I decided. I wanted that man in the corner, that man in the shadows, the husband of the woman I was fucking, I wanted him ramming his cock in my ass.

I guided the redhead to close her legs, my cock still deep into her cunt. This forced my dick to rub harder against her clit. A few thrusts and she had no objection. But it also let me straddle her. My legs outside hers, I widened my stance. I spread myself, for him. I was making an offer.

I slid my dick in and out of her clenched crotch. She was happy. I angled my thrusts, letting my butt wiggle from side to side. I imitated the mare in the parade, trying to entice the stallion.

I heard a chair leg squeak against the floor, a couple steps. He must be right there, right behind me, watching my swaying asshole. I arched my butt up and gave a “I want it” moan. I enjoyed feeling like a harlot and hoped he didn’t think I was too over-the-top.

I heard a belt buckle, then the sound of pants sliding down to the floor. I didn’t look back, but just cocked my ear. I heard the soft scraping of elastic sliding down a leg. I even imagined I could hear that elastic as it passed over the hair on his leg.

I heard him get down on his knees. He steadied himself by putting a hand on my butt. It felt deliciously big, calloused.

“Yes… yes…,” I encouraged him.

I looked down at the redhead. She gave me a big smile and nodded. She was in. Maybe this had been the plan all along. I didn’t have time to think.

His hand slid softly across my butt, to the center, and down my crack. He let his fingers slide as they came to the oil. When his fingers found my soft, open asshole, he slid two fingers quickly inside. I gasped.

“God!” he said, as his fingers easily sank their full length.

I pressed back into his fingers. He pulled them out, put his hands on my back, and leaned forward. I felt the head of his dick, searching, pressing, but not finding. I tilted my hips, moving my asshole down to meet him.

“Oh God!” he gasped as my well-stretched hole let his engorged rod slide deep inside. “Oh my God!” he said. I relaxed as I let him fill me. It felt so much better than that dildo. He bumped my ass with his body. He was all in.

“Yesssss…,” I hissed, pushing back into him.

As he started to pull out, I groaned with pleasure. The redhead pulled me down for a kiss. Our mouths danced as I imitated with my tongue what her husband’s dick was doing to my asshole.

Soon we found a rhythm, pounding into me, as we both became more confident, unafraid. I pushed back into his thrusts, then let them push me forward. As he thrust harder, his balls started swinging and crashing into mine. At the end of his thrust, as I was pushed forward, I let my cock crash into his wife. He was in control, he set the pace. I followed him. His wife followed me.

The husband’s pace became more frantic. I knew how he felt and I knew exactly what he wanted. I squeezed my ass around his cock.

“Oh, God, YES!” he grunted.

He become a piston, pounding me harder and harder. He straightened up, grabbed my thighs, pulling me into him. I knew he was close as he arched his back. His new angle triggered my prostrate, which needed no further encouragement. When the husband gave out a groan, I let myself go past the point of no return. He gurgled as his orgasm crashed over him. He gave one quick thrust and held it. I felt him twitch. I spasmed into my orgasm, causing my asshole to clench his dick. We both groaned with pleasure as he tried to press deeper into my contractions. Below me, the redhead exploded, her body pulsing and bouncing. She lifted us both with her pelvic thrusts, causing another wave of pleasure to shoot from my dick.

At the height of our pleasure, we froze together, a mass of muscle spasms. We floated there, all three of us, in a gigantic orgasmic fog.

The husband was the first to move. My sphincter reacted with a pulse that squeezed out his limp dick. Another pulse and I felt some of his cum ooze out and slide down towards my balls. He rolled to one side and landed next to his wife. I rolled to the other side. We lay there. I put my hand on that lovely redhead’s abs. Her husband put his hand on mine, then she put her hand on top of both of ours. She turned her head to me.

“Next time, I get it in the ass,” she whispered.

“I heard that,” the husband said. “You don’t get to decide. We’ll let…”

He propped himself up on his elbow and looked over his wife’s beautiful bare breasts to me.

“What’s your name?” he asked.

“John,” I said.

“We’ll let John decide.”

“Okay,” the redhead said, giving me a wink.

I looked from one to the other… and let my imagination run wild.

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