Category: Sissy boy mommy

Sissy boy mommy trained that hole to take lots of Daddy cock

Sissy boy mommySissy boy mommy is just so proud of my little angel. He’s become quite the she!

I remember the day I first caught him playing with my heels and tiara, concocting a little wifey pose – I knew right then he was meant for more than just boy things.

Mommy began his training proper, introducing him to daddy’s thick cock ASAP!

At first, he cried and screamed, but I knew my sweet angel would start to enjoy it eventually. I have a lot of different Daddys around, and they all wanted a piece of that young bussy hole.

It didn’t take long for my little sissy to ask if he could gag on daddy’s cock. As soon as those little lips wrapped around that mushroom head, that was it. He was in his sissy element, or should I say she, lol!

Now this sissy slut can’t get enough, often begging me for it in that high-pitched voice mommy just loves. She’s even only wearing girly outfits that are extra slutty. A Sissy mom is so proud!

I think it’s time Mommy steps up the training, though. My sweet sissy angel has been begging for more and more cum, so I think it’s Daddy gangbang time, and they are all going to cum in that bussy!

Phone Sex Mommy By Day, Sissy Boy Mommy By Night

phone sex mommy

I lay him back on the changing mat, the plastic crinkling loudly under his weight. He’s already whining, his hips twitching with anticipation because he knows exactly where this is going. I don’t rush. I take my time unfastening the tabs, the sound of the adhesive ripping slow and deliberate, echoing in the quiet room. I lean over him, letting my breasts brush against his chest, my nipples hardening against the thin fabric of my robe.

 

“You’ve been such a messy boy,” I purr, my breath hot against his ear. “Do you have any idea how much work it’s going to take to get you clean?”

 

I peel the diaper away, exposing his plump, messy ass to the cool air. He gasps, his legs splaying wide in a position of total surrender. I don’t reach for the wipes immediately. Instead, I let my gaze linger, my tongue wetting my lips as I admire the disaster.

 

“Look at this,” I whisper, my voice dropping an octave. “Just a complete disaster. I think you need a very… thorough cleaning.”

 

I reach down, not with a wipe, but with my bare fingers. I slide a finger through the mess, swirling it slowly, watching his face contort in a delicious mix of shame and arousal. I bring my finger to my lips, tasting the salt and the musk, locking eyes with him the entire time. “Mmm, tastes like trouble,” I moan, letting him see exactly how much I enjoy his filth

Sissy Mom Lays Down The Panty Rules For Good Girls

sissy mom

 

Now that we’ve established that cotton is banned, let’s talk about how you’re actually going to wear your lace. A proper sissy knows that panties aren’t for protection—they’re for provocation. I want you in something so tight it makes you gasp, something that cuts deep into your waist and keeps your cock pressed flat and useless against your belly.

 

I love watching you squirm when I walk past you. I can see the outline of your desperate little nub straining against the silk, trying to find a way out. But here is the rule: you do not touch. Not a finger, not a graze, not even a subconscious rub against the fabric. Every time you feel that itch, every time your cock throbs because I’m standing over you in my heels, you remember that your pleasure belongs to me.

 

I’ll spend an hour just teasing you, sliding my hand over the lace, squeezing your balls through the fabric just hard enough to make you whimper. I’ll whisper all the filthy things I’m going to do to you, describing exactly how I’ll make you beg, only to pull away the moment you start to leak. I want you dripping, I want you aching, and I want you absolutely miserable with need. Watching you vibrate with arousal while I forbid you from touching yourself is the highlight of my day. You’re just a leaking little faucet, and I’m the only one who decides when the valve opens

 

Wet Mommy Pussy Is Your Reward!

wet mommy pussy

We come to the most important part of etiquette: the orgasm. Or rather, the lack thereof. A sissy who cums without permission is a sissy who doesn’t deserve to wear lace. You will stay in a state of permanent, agonizing edge. I want your cock swollen and sensitive, your mind completely clouded by the need for a release that I am denying you.

 

When you’ve been a good little slut—when you’ve worn the right lace, kept your mouth shut, and endured my torment without a peep—I might decide to be “loving.” I’ll pull you close, my nails digging into your shoulders, and finally let you feel the warmth of my skin. I’ll kiss you deeply, tasting your desperation, while my hand finally slides under that expensive lace to wrap around your throbbing shaft.

 

I’ll stroke you slowly, teasing you right to the brink, making you moan and sob into my neck. And just as you’re about to blow, just as your toes are curling and your breath is hitching, I’ll squeeze tight and stop. I’ll look you in the eyes with a wicked smirk and tell you that you haven’t earned it yet.

 

You’ll collapse at my feet, shaking and spent without ever having reached the finish line. That’s the beauty of being my sissy. You live for the tease, you thrive on the denial, and you love me all the more for the way I break you. Now, go put on the red lace thong and wait for me in the bedroom. Be quick, or I’ll find a reason to put you back in those granny panties for a week

Sissy Mom Nicolette Trains a New Sissy Boy for the Glory Hole

sissy momI enjoy being a sissy mom. None of my sons act like sissies. But I talk to them all the time. I have helped a few sissies in my personal life too. My daughter works with a sissy. My oldest son ‘s best friend dabbles in the lifestyle too. But this week I met a sissy who knows my husband. And my husband asked me if I would help this guy. Why not? I love to play with sissies.

My husband knows I never mind helping sissies. And I’ve worked with all types of sissies as well as talked to them too. But some like to just dress up and serve mommy. Others like cock training. And some want to be mommy’s little cuckold sissy or even her daughter. I’ve trained a variety of sissies. But my husband’s sissy lawyer friend lives a duplicitous life. Hence why he needs a phone sex mommy.

So, he came over Friday night to play.  And I put on my strap on, and we worked on this sissy learning to suck cock. I know how to suck the chrome off a doorknob so I can teach a man how to give a good blow job. My husband ‘s friend wanted me to train him and then take him to a glory hole. So, we spent a few hours working on his cock sucking skills. Quick study. But he admitted he sucks on his wife’s dildo while she’s at work.

Any Sissy Boy Can Feel Safe to Explore Those Urges for Cock with Me

Honestly, I didn’t need to work that hard. Perhaps he has been practicing on his wife’s dildo though a lot longer than he admitted. A born natural cocksucker. So, I went online and looked for the closest glory hole. Apps exist that will show you where some of them are located. I found a great adult bookstore with glory holes in the back. That’s where I took my new sissy.

We enjoyed it. And my new sissy became the belle of the glory hole. Everybody that came into the bookstore apparently wanted their dick sucked. So, my sissy didn’t have any competition. And I watched him like a proud mommy. I don’t judge. Everybody knows I’m a safe space for sissy exploration. My new sissy spent the day guzzling random cocks. Swallowing load after load too.

And I can help any man be the best sissy. Honestly, I love being a sissy boy mommy.

Sissy Mom Lays Down Panty Rules!

sissy mom

Listen to your sissy mom, you pathetic little disappointments. If you’re going to spend your days scrubbing my floors and pretending to be a girl, the least you can do is look the part. I’ve been checking your drawers, and some of you are still clinging to those hideous, cotton granny panties. Let me be crystal clear: if I find a single pair of full-coverage, beige, “comfort-fit” rags on your hips, I will treat you like the disgusting little pig you are.

 

Granny panties are for women who have given up on life, not for sissies who are desperate for my attention. When I pull those oversized rags off your shaking thighs, I’m not just tossing them in the trash—I’m using them to wipe the filth off my boots before I make you kneel. You don’t get “comfort” in this house. You get lace, you get silk, and you get strings that dig into your soft little hips.

 

If I catch you slipping back into your masculine habits, the punishment will be immediate. I’ll strip you bare, slap that pathetic little cock until it’s bright red, and force you to wear a pair of sheer, neon-pink thongs that leave absolutely nothing to the imagination. You’ll spend the rest of the day shivering in the hallway, your tiny ass cheeks exposed to the draft, knowing that I can see every single flaw of your failed masculinity. You aren’t a man anymore; you’re just my little dress-up doll, and dolls don’t get to choose their underwear. Now, get on your knees and apologize for your lack of taste.

Wet Mommy Pussy Required: Sissy Boy Mommy

wet mommy pussy

 

They had been perfect for my wet mommy pussy. Their submission was absolute, and their holes were primed. As a reward for their hard work, I decided to give them the ultimate pleasure. I laid them side-by-side on the bed, their legs spread wide.

 

I produced a massive, thick strap-on, slick with lubricant. I pushed it deep into Leo’s ass, hearing him gasp as I hammered into him, the plastic cock slamming against his prostate. While I fucked Leo, I forced Marcus to lean over and suck the strap-on’s base, his tongue swirling around the junction. I swapped them, plunging deep into Marcus’s tight pussy-hole, making him scream with pleasure. I fucked them both relentlessly, my hips slamming against their soft, sissy bodies. Finally, I let them touch themselves, “Jack off with mommy!” i screamed as their hands blurred and they jerked their small cocks. On my command, they both erupted, thick ropes of cum spraying across their lace aprons, sobbing in pure, sexual ecstasy.

Sissy Mom Pimps out her pathetic little Sissy Son!

Sissy Mom

Being a Sissy Mom is easy with a faggy little son like you!

I love when I catch my boys stealing my dirty panties and bras, thinking I don’t notice them missing after the gym!

Sniffing Mommy’s sweaty dirty bras and panties every night before you put them on.

Don’t you look so cute in mommy’s panties, you almost look like a real girl!

 Guess since you want to be like your sister so bad, I should treat you like your whore sisters.

I pimp out their tight little holes for men to fuck raw, and yours will be next!

I know Mommy’s firsts with the big black cocks would pay extra to fuck your tight little bussy, baby.

If you wanted to be a nasty little whore like us, all you had to do was speak up!

Your little Sissy hole will make me so much money!

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Wet Mommy Pussy Drips When Sissy Maid Training Gets Dirty

wet mommy pussy

 

Now for the part that gives me such a wet mommy pussy…the labor. I dressed them in tiny, sheer maid uniforms—white aprons barely covering their rounded asses and lace headbands perched on their wigs. They spent their days scrubbing floors on their hands and knees, their fake tits bouncing under the thin fabric.

 

When they weren’t cleaning, they were my slaves. I tethered them to the bedposts with leather cuffs, leaving them naked and exposed. I spent the afternoon playing with them, using a ribbed dildo to stretch their tight assholes. I shoved the toy deep inside one, making him moan as I pumped it in and out, while I used my fingers to stretch the other’s hole wide. I forced them to lick my toes and worship my feet, treating them like the filth they were. They learned that their only purpose was to serve my whims and keep their holes open and ready for whatever I decided to shove inside them.

Sissy Mom Sets ‘Em Straight?

sissy mom

My little guys were far too masculine for my liking. It was time to strip that arrogance away. I started by shaving every inch of their bodies, leaving their skin smooth and sensitive. I forced them into frilly pink panties and tight corsets that pinched their waists, molding them into the sissies I desired.

“Kneel,” I commanded, my voice cold. They dropped instantly. I made them dress in lace stockings and high heels, forcing them to walk in circles until their calves burned. I spent hours drilling them on their new identities, making them repeat, “I am Mother’s little sissy slut,” while I slapped their reddened cheeks. To ensure they understood their place, I used a heavy strap on their asses, leaving deep red welts across their soft skin. By the end of the first week, the rambunctious puppies were gone; only my obedient, trembling sissies remained.

Now came the labor. I dressed them in tiny, sheer maid uniforms—white aprons barely covering their rounded asses and lace headbands perched on their wigs. They spent their days scrubbing floors on their hands and knees, their tits bouncing under the thin fabric.

When they weren’t cleaning, they were my slaves. I tethered them to the bedposts with leather cuffs, leaving them naked and exposed. I spent the afternoon playing with them, using a ribbed dildo to stretch their tight assholes. I shoved the toy deep inside Leo, making him moan as I pumped it in and out, while I used my fingers to stretch Marcus’s hole wide. I forced them to lick my toes and worship my feet, treating them like the filth they were. They learned that their only purpose was to serve my whims and keep their holes open and ready for whatever I decided to shove inside them.