Tag: 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.

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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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.

 

 

Sissy Mom Daphne Needs to Punish Her Naughty Sissy Boy!

Sissy Mom

 

I love being a Sissy Mom for my little bitch boy of a son.

He thinks I have no idea that he’s stealing my panties and heels to play dress-up in his room. I hear him click-clacking his faggot ass across the hardwood floors. 

But when I really knew he was a little Sissy faggot, it was when my huge black dildo went missing! It’s my favorite one with the suction cup on the end, and that realistic pink tip. Yum!

I found it in his room, still suctioned to the wall. My dried pussy juice is still on it, but I saw he has licked some off. That nasty, naughty boy!

When he gets home, I’m going to pound his little sissy asshole wide open as punishment for taking my sex toys!

 

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Sissy Boy Mommy Daphne will turn you into a sissy WHORE!

Sissy Boy Mommy

 

Being a sissy boy mommy is so fun because I can treat you like the little girl I never had! 

You are far too weak and faggy to be a real man, so you might as well just lean into being Mommy’s good little slutty girl. 

 

Try on my panties and thigh-high tights and tell me how perfectly that small little clitty of yours fits. Stuff my bra so you know what it’s like to have huge tits bouncing in your face. 

Don’t be shy now, you pathetic excuse of a man. You look like a beautiful whore, just like me.

I can’t wait to tell all my friends how I get to dress my son up to be my perfect little whore for Mommy’s friends with huge cocks get to play with. 

That’s right, I dressed you up real nice for some BBC to come tear up your hole and fuck you like a little ragdoll.

 

Mommy Whore

 

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Momma Gia plugs the little one’s and shows who’s in charge of this whore house

Sissy training phone sex

When I was a slutty young one I not only know that I wanted to birth a slut at an early age but I used to watch mommy and daddy fuck through their bedroom window. I’d rub my moist pussy and pray that one day I have a daddy that’ll lay me out like that. Well, recently my son’s been doing the same thing and I can’t  blame him, even showing his sissy’s how mommy fucks by improvising on them how all the men run through me. And my little slut whore’s have been getting away with trying to breed, just like I had once done.

But now my offspring’s been very very naughty lately, taking every cock that walks through the door before mommy has a bite. I know I’ve trained my sissy’s well but it’s gotten out of hand, especially since I’ve got another little whore to add to my incestual bunch, she constantly feeding and taking all the attention.

I caught my little sluts being whores sucking, fucking and pouncing on my guests right when they arrive, in front of my eyes. It doesn’t matter how old the man is my little girls will swallow you whole while my little boy sissy faggot sucks on your balls desperately trying to start licking your bunghole. My offspring enjoy eating your fecal cum like candy. Their desire to breed like mommy has gotten out of control, the bigger and the more they blossom their titty’s and shaft expand rapidly. They also are hungry for milk, the need increases.

Lactating phone sex

Sissy training, learning who’s in charge!

Mommy’s rules have been broken though and my little one’s need to be punished. I take control and bend them over to shove shit up their asses and stretch out their tiny tight gaps and remind them who’s in charge of all the daddy dicks that cum through here. While they sit on their little bottoms with plugs up their asses I love to give them some reminder spanks, leaving them bruised and red.

They learned their lesson well and went back to feeding from my new boop some milky jugs. We’d love to have you daddy!

Sissy Boy Mommy Loves Letting Her Sweet Sissy Boy Get Fucked By Strangers

Sissy Boy Mommy

Being a sissy boy mommy is so much fun! I taught my little one how to be the perfect sissy boy since he was very little. He loves stroking his small hairless cock as he blows men with big fat cock while I rub my wet sissy boy mommy pussy. I tell him to be a good sissy and take that fat cock all the way down his throat like a good little slut. I love inviting all the P daddies in the neighborhood over to see him dressed up as a sweet little sissy bitch and suck their cocks. The best part about being a sissy boy mommy is when I get to watch him take cock up his sweet pink boy pussy. He moans so loudly and tells me how good it feels. It makes my pussy so wet and after they are done gaping his tight little hole I give them a boobie job with my huge DDD tits and tell them how sexy it was watching them fuck my faggot sissy boys asshole. When they cum all over my big tits I have my little sissy boy lick all that sticky sweet cum off my fat titties. Just like the sissy whore he is.

Sissy Boy Phone Sex Got Gunner Speed Strapped By Momma

Sissy Boy Phone Sex

My Hands Rushed all over Gunners Silky panties. His Cock so hard the imprint was prominent in those sissy boy panties. I led him to my bedroom, my finger tangled in his panties, leading him. This reminded me of a sexy Sissy Boy Phone Sex call. ( Don’t forget to read part 1 first click Here)

Pushing him back on my bed, I licked my way down his hard body. Nipping and Licking his abs. I ran my fat wet tongue over his cock inside those panties. Licking the silk, saturating, the fabric getting it soaked with saliva.

I reached into my nightstand, grabbing my strap-on. He watched with wide eyes, never stopping his stare. I Fastened it around my waist, and interlocked the 6 inch Rubber Dick. ” You want to know what it feels like to get fucked?” I shook the cock at him.

” Im Nervous” He said trembling.

A wicked smile came over me as I slid his panties down. ” Don’t worry baby, Momma is gonna take care of you… Trust me”  Rubbing my hands against his garters and stockings. I stood between his legs, looking down at him. Taking that fat stiff dick in my hand, I Jerked him slow and put my head down between his ass cheeks. Giving him a nice little slick rim job, and spitting on his little brown eye.

I tapped the head of that rubber dick against him, pushing against him trying to break that little ass open. Spitting on his cock so I could stroke him while I fucked his little ass. “Open up for me, deep breaths” Once his breathing stopped rushing, he opened just enough for me to slide in deep. I slid hard, steady rhythm. My hand massaged his prick, and he moaned so pretty.

I humped and bucked my hips. My Pussy Lips pressed against that harness as I fucked Gunner. Jacking that young cock off. Sinker deeper and deeper, inch by fucking rubber inch. His chest became so tense as I encouraged him to cum Hard For me. Never Ceasing my beat. i Slung my long rubber cock to that beautiful Sissy boy, and he made the most beautiful noise when he came. Blasting off his rocket rod and shooting his spunk all over my tits. I was covered in his white candy rain. Yum, turning out that cute little bitch boy was sexy as fuck.

I was a Horny Sissy Boy Mommy Saturday Night

Sissy Boy Mommy

Saturday Night I was dressed up as a hot little fucking witch. We have a Halloween Costume party every year and all my sons friends come over. We even offer a 200$ Cash prize for the best Costume. I never thought I would be a Sissy Boy Mommy after the party though.

So, My Youngest Sons Friend, Gunner came Dressed ad Ed Gein posing as his Mother. If you’ve watched the show on netflix, you know what I’m talking about. He had on the frumpy Blue dress, the wig and old lady heels, but the resemblance was uncanny. He even had the hose on. I fell in love with the show and Ed Geins story, so I was a little Biased. Gunner won the contest.

All Night I couldn’t take my eyes off of him though. Gunner is a strapping young boy, athletic. He works on cars. He is just one of those manly boys. I would have never thought he would come dressed in drag. I also never would have thought looking at him would turn me on as much as it did.

Gunner drank at our party and he knows the rules, you drink- you stay.

After The party was over most of the boys who were drinking were outside at the bonfire getting rowdy. They all like to pile up in the pool house, and some scatter in here in the main house too. I always wake up to a Few laid out around in my living room.

Alone in the house, I had just hung up with my husband and took off My Costume. I put on My Robe, tits perfectly set showing my cleavage. Tying it around me and walked into the kitchen to pour myself some wine. In walks Gunner.

” You Like it Momma B, I mean I did win” He boasted.

” Oh yes! I Love it! Let me get you that money before I forget” I recanted.

” Momma B, do you wear these too? Because I’m not gonna lie, I Like the way they make me feel” Gunner said, looking back over his shoulder and raising his skirt to reveal, they weren’t hose. He was wearing nude thigh high stockings and a garter, with white silky panties.

Looking down at his cock, I got so excited. He was hard inside those panties. I didn’t say a word, my hand just reached out and rubbed the form of his cock through the silk. My fingertips traced the shape of his cock, and Gunners strapping, young cock grew in my hands. A Grower and a show ‘er, I thought.

I knew I would have to have him that night….

second part coming soon.