As the extreme feminist reeled off her hatred of the patriarchy, I questioned why I was on this date. Little did I know it would end in one of the most erotic pegging stories ever.
I was sitting opposite Michelle. Originally from Germany, she was in her mid-30s and living in New York. We were in a hipster grunge bar in Brooklyn. Not my kind of place at all.
We’d hooked up online through Adult Friend Finder (classic), and I messaged her first based on her erotic kinks, busty but petite frame, and witty responses to my messages.
I have nothing against feminists, but my date was on the extreme end of the spectrum. She wished extreme violence on misogynists and a female-dominated world.
Heavily tattooed, a regular face at various local political protests and with the quintessential lightning blue hair, she was the caricature of a hard-left feminist.
But as the drinks flowed, the more she talked about female superiority, the more my erotic Femdom kinks were being unceremoniously triggered.
A Joke Turns Sour
It was closing time. Our opinions and stories clashed a few times, but we were having fun and Michelle had great banter. We flirtatiously agreed to head back to her place to carry on drinking.
There, her political diatribe continued. It escalated to who has it harder in life: Men or women? Although this girl was politically extreme, she could usually take a joke, and I continued the banter.
“Women have it way easier! Especially in sex!”, I said jokingly, “Do you know how hard it is to be the guy in sex? It’s damn tiring.” But Michelle’s face dropped. This really hit a nerve.
“So,” Michelle said in a pissed-off tone, “Do you just meet up with girls on AFF all the time to get your dick wet? I bet you tell them everything they want to hear, don’t you, asshole?”
I felt like my alcohol-fuelled banter had gone too far. Michelle looked genuinely angry, but also had a grin on her face. I was expecting to be shown the door and go home with a hard-on.
“You probably met me wanting to conquer a feminist pussy for the first time, right?”
“Well, it is quite a sexual achievement!” I laughed, “It’s kind of like wanting the things you can’t have, do you know what I mean?”
“Well, come on then”, Michelle said whilst standing up and finishing her drink. “Follow me into my boudoir. I will warn you though, feminist sex with me isn’t what you might be used to”
I sank my whiskey and coke and started to follow her into the bedroom. As I stood up, I realized how buzzed I was. Fuck, I’m really drunk, I thought to myself.
My First Time in a Feminists Lair
In her bedroom, various artwork surrounded a Gothic, iron-framed bed. The transgender pride flag that was pinned to the wall didn’t fit the overall aesthetic.
She kicked off a chilled-out Spotify playlist and invited me to join her on the bed. We started talking about our kinks and craziest sexual experiences and stories.
Michelle had tried a lot. Orgies, domination, submission, bisexuality, public sex. You name it, she’d done it. But her topics soon turned to anal. More specifically, my experience.
I confessed to Michelle that, up until that night, my anal experience consisted of some fingering with a kinky girlfriend. But it was fun to explore. A deviant look spread across her face.
Michelle pulled out a black velvet bag from her bedside table and poured the contents out over the bed. Cuffs, whips, blindfolds, and a plethora of sex toys fell out in front of me.
I Don’t Tolerate Mansplaining!
“I’m going to show you how a feminist fucks. Do you trust me?” Michelle asked whilst rattling a pair of handcuffs. I was so horny and drunk, I would have agreed to anything. And I did.
Laying on my back, my hands were cuffed behind me. My ankles were then bound to the two posts at the end of Michelle’s bed. My asshole was exposed and I was feeling very vulnerable.
Michelle started with some light, lubed up fingering of my ass to open me up before slowly progressing through her collection of strap on cocks.
After an hour of prep, she settled on wearing her favourite toy to peg me with: An 8 inch, jet black, realistic cock. As soon as she saw I was getting comfortable, the real pegging started.
I felt an incredible urge to go to the toilet, but Michelle told me it would pass. As the tempo of her pegging built, so too did her humiliating dirty talk.
“Guys talk so much about sluts and whores, but look at you now. You’re being anal fucked into submission by a woman wearing a black cock dildo.” She said with a look of disgust on her face.
Just as I was getting used to her pegging, Michelle seemed to go harder. I could feel my ass getting bruised as she pegged me into submission. I involuntarily cried out in pleasure and pain.
Now You Know What Porn Feels Like!
The pegging stopped as Michelle grabbed the remote for the TV in her room and flicked on a late-night hardcore porn channel. The artificial moans of a submissive woman being DPd filled the room.
“I bet you watch porn all the time, don’t you? I bet you get off on the exploitation of women for your sexual pleasure!” Michelle aggressively asked as I nodded in agreement.
“Well, now you know how it feels! The next time you watch porn, you’ll feel a phantom toy in your butt as you watch pornstars getting fucked. When you cum, it won’t be to the pussy on screen, it’ll be to the thought of my dildo pegging you into submission!”
The erotic porn sounds seemed to send her over the edge. The pegging was too intense. I felt like I was going to cum hands-free like a sissy.
“Please, Michelle, you’re going too hard,” I pleaded. I was met with a rude and humiliating laugh as she slowly pulled the strapon out of my ass with a pop.
“How about you shut the fuck up? Acting like an Alpha male all night now you wanna tap out?” Michelle jeered whilst reaching into her laundry basket. “I don’t tolerate mansplaining, prick!”
Michelle fished out a pair of her dirty pink panties and rudely stuffed them in my mouth. I could taste the sweet but musty scent of her pussy and moaned out through the fabric.
“If my mouth can take it, then so can your ass!” Michelle laughed as she pounded my hole.
My neglected cock bounced pathetically as my asshole was used. I was desperate to masturbate, but after a while, my g-spot being pounded felt immensely better.
“This is what a whore looks like,” Michelle grunted through gritted teeth. “When I’m finished, you’ll never be an Alpha male again. Your wrecked asshole will be a permanent reminder that a woman made you submit.”
The Pathetic, Obedient Type of Man
It felt like forever since Michelle had started to open me up with a beginner dildo, but her energy hadn’t waned. She was pounding into me with more intensity than ever.
“You’ve been the type of man I like in my company tonight: The pathetic, obedient type. I think,” she paused for breath between thrusting into me, “I think you deserve a reward!”
As Michelle pulled out of me, I felt my ass twitch as if it was thirsty sucking out in hunger for the rubber cock that was defiling it. She repositioned herself up the bed and above my face.
Before I could appreciate fresh air as the panties were pulled from my mouth, Michelle plunged the strap on dildo for me to suck. My mouth filled with the taste of lube and my own ass.
“I’d been fucked senseless and my ass ached. Do you know how a cold beer tastes after a long, hard day of work? This is what it felt like.”
It was downright humiliating. But my cock didn’t agree. It was quivering and dribbling pre-cum. Looking back, Michelle aggressively flicked my dick whilst laughing cruelly.
So desperately horny for pussy, I found myself deepthroating the cock just to get closer to Michelle’s crotch. After about five minutes and a lot of throat bruising, she rewarded me.
The strap on was pulled aside and her hairy, meaty pussy was let loose. In seconds, it was firmly planted on my face. I sucked and slurped at it like it was my last meal on earth.
I’d been fucked senseless and my ass ached. Do you know how a cold beer tastes after a long, hard day of work? This is what it felt like. Michelle’s feminist pussy tasted absolutely beautiful!
As I stuck my tongue deep inside her pussy and savoured every inch of it, Michelle shifted so her pretty pink asshole got equal attention. I didn’t discriminate and shifted from pussy to ass.
As I worshipped her holes with my tongue, I noticed Michelle staring down at me with a cruel and mischievous look on her face. What trick has she got up her sleeve next, I thought.
“I have a confession.” Michelle said with a sly smirk, “You’re not the only guy I met off Adult Friend Finder today. I slept with a guy earlier this afternoon. I didn’t get a chance to shower in between. You don’t mind, do you?”
Michelle had chewed up my masculinity and spat it out ages ago with her relentless pegging. With my mouth full of pussy lips, I shook my head to confirm I didn’t mind.
“Good boy,” Michelle said, pulling off my face, prying open my grool-soaked lips and spitting deep inside my mouth. “I think it’s time for you to cum!”
The Only Thing Men Deserve
Her soaked pussy was covered up by the strap on, and it was soon being lubed up again and slid inside my ass. As the pegging resumed, Michelle spat on her hand and slowly wanked me.
“Each thrust in your ass represents every one night stand you’ve had, every woman you’ve used solely for sex. This is the only sex you deserve, you prick! Say it!”, Michelle barked.
“I deserve this! Pegging is how men should be fucked! Women are superior to men!” I moaned out with my voice breaking from her aggressive thrusts from her hips.
Then, I felt my asshole caress the strapon harder than ever. My balls tightened, and I erupted. White ropes of spunk coated my body. It was one of the hardest orgasms I’ve ever had.
The pegging sex had finished and the room was now silent aside from heavy breathing from us both. We were both sticky with anal lube and bodily fluids. But Michelle wasn’t finished.
“Open wide, fucker!” Michelle muttered whilst scooping up the ropes of cum on my body with a look of kinky pleasure on her face.
With my hands still behind my back, I had no choice. I reluctantly opened my mouth and closed my eyes as she fed me my own cum and made me swallow it, despite my gagging.
An Unceremonious End To The First Of My Pegging Stories
As I was uncuffed and led out of the bedroom, I felt utterly humiliated. It was reinforced when Michelle gathered my clothes and threw them at my feet.
“I enjoyed that. Now call yourself a cab, I’m going to sleep.” Michelle muttered.
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My pegging virginity had been lost and I had been taught proper submission. I didn’t even have a chance to wipe off the sticky remains of my orgasm or shower.
Disclaimer: This erotic pegging story is true, but names, dates, and locations of the story may have been changed to protect the identity of those involved. This article may contain affiliate links. If a purchase is made through them, we receive a small commission that goes towards running the site.
