Top Sissy Pegging Stories for Enthusiasts

Top Sissy Pegging Stories for Enthusiasts

Here’re the Sissy Pegging Stories for you:)

MAID TO RULE

Standing in front of the master bedroom’s door, I realize it is times like this that are the sole reason the middle-aged couple hired me. I’m a mediocre cook, only passable at cleaning, barely have the patience to tutor the youngest child and am not pretty enough to be a trophy hire, but there is one thing I do that the other maids can’t. (Pegging)

Sissy Pegging Stories

I turn and look into hallway mirror, making sure I’m looking my best. A mistress in a maid’s uniform, I know the impression is half the performance. White thigh highs, five inch stiletto heels and a low cut top only matched by the hemline so high my cock is swinging below it. Satisfied that I’m putting forward the proper image, I open the door and walk in confidently.

“Good evening,” I say, tinging my words with malice. I’ve never been the kind of domme to force the terminology of submission on my submissives nor do I waste much time on formality.

Both the husband and wife look towards me from their bed, apprehension and unease on their faces. Even after months, they haven’t quite gotten comfortable with their roles and rarely react to my presence quickly.

I don’t give them the time to figure out either, quickly grabbing the wife by her long blonde tresses and yanking her towards me, head-first, “Get over here, you goddamned slut,” my voice a harsh bark to back up my actions.

I stare her husband in the eye as I pull her head back, squeeze her cheeks to force her mouth open and kiss her deeply, lewd slurping noises filling the room when our tongues intertwine. I can feel his jealousy and it nourishes me, even as I reach into the pockets of my uniform and produce a set of handcuffs.

I let go of her cheeks and pull her hands down behind her back, snapping the cuffs into place and completing her restraint. My hand reaches elsewhere and grabs a hold of her titflesh, mauling the sensitive globe before forcefully pulling it from its confines in her nightgown.

She moans into my mouth and in response I slap her, hard. “Fucking whore!” I yell at her before jamming my tongue back into her mouth. The husband stirs, vacillating between wanting to intercede and being frozen by my glare. I instinctively know to back away at this point; I’ve enough experience at this to know when I’m close to overplaying my hand.

I let my tongue slide from the wife’s mouth, licking her lips as I break the one-sided kiss and massaging her single exposed breast in my hand before I push her down, face-first, onto the bed.

I keep my eyes on the husband as I explore her curves with my hands, starting from her slender shoulders and ending at her ample hips. It’s then I dig in with my fingers and pull her back to the edge of the bed, then raise the nightgown up over her waist and slide her panties down her legs and from around her feet.

“You married a fucking whore, you know that? I bet you couldn’t count the guys that have run through this bitch and you still put a ring on her.”

Grasping her panties in my hand, I press them to my nose and inhale and then lick my lips for the husband’s benefit. His cock throbs at the sight of me sniffing his wife’s panties and I get another deep breath before balling them up in my hand. I grab her hair once more, pulling on it hard enough to force a cry of pain out and take the opportunity to stuff the panties in her mouth.

She looks up at me, fear on her face, before I throw her head down onto the bed and drive her legs apart, rubbing my dick against her meaty cunt lips. I give one last look at her husband.

Then I thrust forward and make a cuckold of him.

“Oh fuck yeah, this is some good pussy you got here…”

The wife moans into her make-shift gag and I press deeper, forcing her to stretch to accommodate my size. The squish of her juices is loud enough the husband can hear and I see his cock wag up and down as the sound reaches his ears.

Pulling my cock out slowly, I let her cunt lips stretch around the head of my prick before it pistons back into her, letting her scream and moan and cry. I drive harder this time, trying to get the last few inches into her, but it’s to no avail.

Instead I begin a steady pounding, keeping my hand on the back of her head, forcing her face into the sheets as I put my back into fucking her like a ten dollar whore. My thrusts send ripples through her body – especially her big, pale ass – the juicy sounds of pussy cream being speared joined by the sharp slap of flesh on flesh.

The wife has a nice sluthole on her – not tight enough and definitely not deep enough, but still plenty good for a nice hatefuck – and I spend the next few minutes focused on enjoying her. Every few thrusts I give her ass a hard slap with my free hand, until there is a hand-sized, dull red blotch on her cheek.

“Want me to stop? Huh, bitch? No? Of course you wouldn’t, you fucking slut,” I pull her head up and slap her again, “Worthless pieces of fuckmeat always want dick, don’t they?”

She whimpers through her panties while looking up at me, tears running down her face, but an expression of unadulterated lust in her eyes. I cruelly take hold of one of her nipples, first twisting it a full three hundred and sixty degrees then pulling it away from her body, lifting her breast upward in the process. The wife continues whimpering, taking a higher pitch as I first grab her nipple, then transitioning into an outright scream when I wrench it forward.

When I hear her make that noise, it causes my balls to surge with a huge load of cum.

I look back to her husband one more time, staring at him while I pummel his wife’s cunt, the one she swore to give to him and him alone.

My eyes are heavy-lidded, my lip is quivering and I’m slamming into her body like a head-on collision at eighty miles an hour. The wife’s exclamations have taken the pathetic character of a sort of half-sobbing, half-sniveling yet I drill her mercilessly. The husband knows what’s coming and he’s powerless to stop it under the influence of my gaze.

But I decide to flip the script and yank my cock out of her sloppy mess of a cunt with a loud slurp. Then I rise up on the bed and pull her to her knees by her hair. I spit right on her face and slap her with my dick before reaching into her mouth and roughly pulling her panties out, throwing them across the room onto her husband’s chest. With one parting slap, I finally push her mouth under my balls, “Lick me! Get your tongue on this pussy!”

She extends her tongue gingerly, her first licks tepid, weak little strokes of the tip of her tongue, so I pull her face away, spit on her again and scream at her, “I said fucking lick, not tickle! Get your fucking mouth into gear, you whore, and do your fucking job!”

Her mouth opens and she pushes her tongue as far out as it can go. Satisfied, I grab her head with both hands and haul her face back under my pussy, pushing the folds of my pussy onto her tongue, “Come on you filthy slut, tongue it.”

The wife laps at my pussy like a thirsty dog but it isn’t enough for me. I ball my hands in her hair and grind my sex against her open mouth, cooing softly as her face darkens from being denied oxygen to breath. She changes her method in response, slipping her tongue deep and rolling it back in a “come hither” motion.

A wet smack sounds every time her tongue leaves my juicy pussy and her lips attempt to breakaway. It sounds a lot like she’s making out with my honey pot, which I think is sexy and let her know it: “Mmmm yeah… eat it, eat that pussy whore. Get your tongue deep in there…. mmm… that’s it. At your mouth is good forsomethingother than sucking cock.”

I look toward her husband, “Maybe hubby wants a taste?”

He makes a whiny, non-committal noise and I laugh briefly at his expense before his wife’s tongue slides along a particularly erogenous spot in my pussy. I grit my teeth and hiss, throwing my head back and continuing to grind against her mouth for a few more seconds before letting go of her hair and stepping back.

She looks like an absolute mess. Her face is an absolute mess of wetness, smeared about her lips, cheeks and chin, with shiny rivulets leading down her neck to her chest. Her hair has that matted, disheveled look that typically accompanies rough sex. Her skin is bright red with exertion, while her chest is visibly heaving thanks to her heavy breathing and her eyes are glassy with satisfied lust. I put my palm on her face and push her aside, walking across the bed to her husband.

He’s panting like a dog and so I treat him like one. My first action is to get between his legs, spitting on my thick nine inches of girlmeat before letting it flop against his member, only a bit over half my size. He opens his mouth to say something, but my hand covers it in a flash, pushing him flat on his back as I grab his wrists, “No. No talking,” I order him sternly before removing my hand.

The husband nods and, satisfied he will not disobey, I let go of his mouth and reach into my maid’s uniform for the second set of handcuffs, briskly locking his wrists to the bedpost. He tries to pull them away and the cuffs clang against the heavy iron while I smile wickedly. I run my fingers along his jawline, admiring his handsome features before calling for his wife, “Get over here whore!”

His wife approaches on her hands and knees, with the sort of slow meekness one might expect from a child anticipating a punishment. That actually isn’t terribly far off the mark and I grab the back of her neck, “Suck your husband’s cock. Don’t stop until I say,” leavening my words with implied threat.

She takes to my orders with eagerness born of fear, grabbing the base of his dick and bobbing her head up and down rapidly. I watch her for a few seconds, stroking my own cock at the same time before getting down to the business at hand. Using my knees, I force her husband’s legs apart, rubbing the head of my cock against his tight, heavy balls.

He groans, but cuts it off sharply when I look up at him, remembering my words and not wanting to risk my wrath. I reach to his nipple and give it a painful twist anyway, just to remind him I’m in charge and he strains to stay silent, especially when I twist harder.

But he’s good at obeying and so I go back to my original exercise, moving the head of my cock down from his balls, slowly across the perineum and finally to his super-tight hole. I slowly rub myself in circles around his ass, smearing precum all over to help ease my way in.

I could feel him tense up as he felt my stiff prick preparing him for a rough ride, his body squirming away. I run a gentle hand through the top of his crew-cut black hair to calm him. But I juxtapose this act of tenderness with one of brutality when I reach down to grab his wife by her golden locks and cruelly mash her mouth down, his dick bulging her throat out as it blows past her tongue. I hold her down for a few seconds and then let her pull back, only to slam her back down again.

Her husband breaks discipline with an unrepressed bellow, “Oh, fuck!” as his wife’s lips engulf his full length again. She chokes and gags, attempting to pull away, but I keep a firm grip on her head; she doesn’t get much more than an inch or two before I press her back down, which must feel absolutelyamazingto her husband.

“Don’t run from it bitch; you know you’re a cocksucking whore! Suck his fucking dick, get in there!”

A deep blush on her face, neck and upper shoulders has appeared, caused by asphyxiation. Her mouth is filling with spit, her glassy eyes pouring tears as I make her take his dick to the back of her throat. The sloppy noises caused by her gagging and head bouncing are loud enough to bounce off the walls of their bedroom.

The sight and sound of her in such a predicament turns me on to no end and my own wet meat drips with precum while my cunt juices run down the smooth skin of my balls. I could cum just from abusing her like this.

Unfortunately for my orgasm, I know she needs to come up some time before she passes out or throws up. Releasing her hair from my grip, she immediately bounds upwards, gasping and choking, her face a sticky, glistening mess. Spit, precum and tears are all marking their territory on her skin, giving her face a sort of glimmering radiance, a testament to her harlotry.

I spit on her forehead to add my own tribute, then slam her face back down, “Get that fucking dick in your mouth and suck it! Don’t make me make you or you’re not going to like it!”

I watch her scramble to stuff the dick between her lips, eager to please; and to avoid punishment. It made me smile and I reached down to caress her backside before laying into her with a hard slap on her wide ass. She moaned around her husband’s length, burying him in her throat with her eyes shut tight.

“Good girl,” I told her cheerfully.

Satisfied the whore was doing as instructed, I returned my attention to her husband, pressing my girlstick into his back door more insistently. He moaned softly and squirmed and I pulled back slightly to spit on my knob, working it in a bit with my hand before pushing again.

I went harder and he wiggled out of the way, so I reached down to his balls – wet with his wife’s drool – and took a healthy dollop to lube his asshole with. He wormed around a bit as I moistened his butt, but I paid no mind and, once convinced he was prepared, I finally stabbed myself into him.

It was only the spongy head but he cried out, so I slapped him in the face with the back of my hand. I held only a bit inside, letting him adjust to my fun stick before pushing deeper. Whereas the head was soft and pliable, my shaft was definitely not, and so I gave him something to scream about when I sank the next eight inches up his butt.

The husband was tight and hot and felt so good wrapped around me I had to close my eyes and focus to keep from crossing the point of no-return. He hollered, he cried out, he begged, but nothing stopped me as I steadily bore into him.

The only possible relief he had was his wife, still enthusiastically sucking even as he wriggled away from me. I ignored her for the time being, preferring instead to slowly slide back a bit and spit on my shaft again, then push past his taut, quivering entry. He cried out – again – and I slapped him – again – landing a solid blow on his cheek which left an imprint of my hand on his skin. It wasn’t that I was trying to be cruel (well, OK, maybe a little) but I couldn’t permit disobedience, especially not without consequences.

As I burrowed deep once again, my hands naturally found themselves under his legs and I hefted them onto my shoulders, folding his body in half like a cheap plastic lawn chair. That set me up to really get after him, forcing my full length into him and finally bottoming out in a tight, hot boyhole. From the sound that came out of his mouth, he didn’t really like it, but that wasn’t what was important.

I started in on him in earnest, the meat-packing sounding off loud and clear. His wife hadn’t stopped sucking him off, but he must’ve gone partially soft in her mouth because she held her lips around the base.

Even so, he was gritting his teeth and holding his eyes shut tight, making strained breathing noises with every slam of my hips into his backside. His balls were bouncing up and down as I tore his backdoor off its hinges, beads of sweat appearing on both our bodies. Missionary position wasn’t too bad for this sort of work, especially since it allowed me to see the pained look on his face. It’s a huge turn-on to turn a guy out.

“You like that, don’t you little sissy? Too bad I’m gonna dry out soon… then it’s gonna really hurt,” it was a leading statement and he knew it, but whimpered anyway, “I suppose I could use your wife’s drool to get you wet –”

“YES! DO IT!” he cried out, deciding to break my rules before I broke his ass.

“Mmmm… I dunno, you’re –nnnngh! – ass is pretty nice… so tight and so –unf! – hot! I can’t just stop –mmmyeah– on a dime in something this good…hhhnnngh! You’re gonna have to –mmmm– beg me, like a good boy.”

“Please! It hurts so much!”

“You can beg better than that…”

His face contorted into an expression I couldn’t quite read and he let loose animalistic cry. I pulled back gingerly. I didn’t want to risk seriously hurting him for real and wiped some spit off his wife’s face in a clandestine fashion, hastily applying it to the length of my shaft that was outside him before I resumed. Fortunately, he didn’t notice, his scream giving way to a low whimper, “I’m begging you, please, please, please, spit on it, I can’t take any more…”

I audibly spit again, this time spreading it around his hole, still keeping a deliberate pace with my re-entry. His butthole was clenched up tight and I could feel it squeezing on every inch. I spit on it again, then put my hips back into it, lifting his leg that had fallen back onto my shoulder. My balls were churning and the home stretch was in sight.

“Do you wanna feel me cum?”

“Yes!”

“Where? Do you want it up your – mmmf! – butt like a good little sissy boy?” Or – nnnghf! – do you want it – unnngh! – all over your face like a slut? Maybe you’d like if – unnnf! – pulled right out and sprayed it on your – hnnngh! – whore wife instead?”

“My ass, please, cum in my ass!”

I smiled. His wife’s head was back to bobbing up and down. Apparently being ruthless stretched and told his wife was a prostitute gave the husband’s dick the encouragement it needed to get fully hard while he was being sodomized. I only cared insofar as it gave his wife’s mouth something to do while I had my fun. And on that note, I leaned over, putting my hands on his shoulders, with his legs pressed against my chest .

I threw my full body into pummeling his hole, withdrawing mentally into the zone where only my pleasure matters; I couldn’t hear his cries, feel his feeble attempt to hold me back nor see his face in agony. It was all me and the sensation of plundering the body under me like a pirate on unpatrolled seas.

My girlstick thickened, my balls grew into tight orbs and my breathing became ragged. I dug my nails into his shoulders. My hips smacked into his wife’s head.

Finally, I gritted my teeth and closed my eyes, throwing everything into using my cock like a piston until I hilted in his ass and he squeezed tight on my base. The cum didn’t immediately shoot, my orgasm first jolted through my body like a lightning strike, and I screamed.

A few heartbeats later the massive load of nut-honey I’d been building up burst off inside him, drowning his guts and spilling from around the edges, running down his ass is stark white rivulets. I pulled back and thrust forward one more time, a second series of cumshots dribbling out weakly as my length began to retract on its own.

I opened my eyes slowly and raised up. His wife’s mouth was still working, even though her lips were coated in his cum. Judging from the fact that it was dripping from her nose as well, I guessed he’d cum something fierce and she’d been too slow to swallow it all.

My dick slipped out on its own, wilted down to its usual seven inch flaccid length and I stood on my knees, fishing the key to the cuffs from my pocket and undoing the wife’s restraints. The husband was still breathing heavily with his head laid to one side; I wasn’t sure he wasn’t asleep. At any rate, my work here was done and I backed off the bed, grabbing a moist-wipe to clean myself off before straightening out my maid’s uniform and walking out the room.

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