Category: Sissy training phone sex

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.

Living Out Your Mom Fantasies With Birdie

Mom fantasies

Come here, sweet boy. Mommy wants you right against her chest so she can feel how eager you are. Here, wrap those warm lips around my nipple. Suck slow and steady, just like that. Drink every drop of my milk while my hand slips inside your pants and wraps around your cock. That’s it. Mommy can feel you getting harder already.

When you call me tonight, you’re going to tell me every single thing you did right today. I want to hear how good you were so I know you’ve earned the treat I’m saving for you. If you’ve been my very best boy, I’ll let you push that thick cock deep inside me and pump every drop of your hot cum straight into my pussy. You love that thought, don’t you? Filling Mommy up until it leaks out around you.

But if you’ve been naughty, you already know what happens. I’ll have a paddle ready. You’ll turn around, drop your pants, and brace yourself on the bed. I’ll make you count every stroke and thank Mommy for teaching you how to behave. My free hand will reach between your legs to massage your balls while your ass turns red and hot. And when I’m finished, you’ll still beg to breed me later because you can’t help yourself.

Now keep sucking, good boy. Get all of Mommy’s milk while you imagine sliding inside me tonight and emptying those heavy balls. I want to hear every filthy detail when you call. Tell me how badly you want to push deep and give me every drop. If you’re good, I might even spread my legs afterward so you can lick my pussy clean after you’ve filled it.

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.

Mommy Whore Becomes Sissy Boy Mommy!

mommy whore

 Today, my daughter and I decided that my son was far too “masculine” for his own good. It was time for a complete overhaul. We spent the afternoon stripping him bare, shaving every single inch of his body until his skin was smooth as silk, and squeezing him into a tiny, frilly pink lace teddy that barely covers his twitching little cock.

We spent hours teasing him, applying heavy mascara, glossy red lipstick, and a pair of towering six-inch heels that make his ass pop perfectly. He looked absolutely pathetic and gorgeous—a total sissy doll. We spent the last hour playing with him, rubbing his nipples raw and reminding him that he’s nothing more than a toy for our amusement.

But the real treat? We invited a massive, thick-cocked friend over to help us “finish” the training. My son is currently trembling in the corner, wearing nothing but lace and makeup, staring in terror and lust at the huge bulge in the guest’s jeans.

The big guy doesn’t care about “son” or “daughter”—he just sees a tight, primed little hole waiting to be stretched. I can’t wait to watch him grab my sissy by the hair, flip him over, and absolutely wreck that tight little ass until he’s leaking cum and sobbing for more.

Stay tuned for the photos of the aftermath! 💄🍑💦

Sissy boy mommy shares with a lot of horny Daddys

Sissy boy mommySissy boy mommy began transforming you into the perfect submissive slut.

From day one, it was all about feminizing you. You look so cute with bows in your hair and dressed in a pink onesie.

Now that you are a big sissy, it’s time you went through your puberty.

Your little clitty has been constantly dripping.

That means you’re ready for Daddy to fuck you. Now, as puberty hits and your little dicklet constantly drips with precum, it’s time for you to graduate to the next level. Daddy’s hungry for that untouched bussy, and Mommy’s here to guide you through it.

I’ve done this countless times before, taking hard, throbbing cock and being an obedient whore. When you follow orders and suck and fuck right, you’ll really make me proud.

It will be amazing watching you come to life as a sissy slut is like a high dose of adrenaline straight to my pussy.

Seeing you blush and tremble as Daddy’s meaty cock approaches your virgin hole is pure ecstasy. Your innocence is a delicious treat, and I savor each moment as I hold your hand, reassuring you that it’s okay, you’re safe with Sissy mom.

 

 

Mommy Makes Sissy Son-in-Law Rue the Day

sissy boy mommy

Everybody knows my fat Mommy pussy is better than any hot young cunt but that pathetic excuse for a son-in-law thought he’d get to fuck my sweet pussy when my sweet daughter picked up an extra shift at the club. He begged, “Anything, Mommy.” As if! What a dumb, cock-hungry slut. I had other plans. I stripped his worthless ass naked, strapped his fat, useless cock in a cage until it turned purple, and painted his lips with my gloss. Then I bent him over the ottoman and fucked his tight, boy-pussy raw with my thickest strap-on.

He squealed like a little bitch with every thrust. I called him my greedy, gaping cumslut, my limp-dick bitch. By the time I finished, his ass was a sloppy, dripping mess and he was crying, thanking me. That’s right, princess. You’ll learn to serve Mommy’s pussy with your throat and your asshole. Not that limp little worm between your legs.

So now Mommy’s got a new princess. Who’s next?