Category: Sissy boy mommy

Milf chat with Mommy Pearl

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Both of my sons were in for my birthday this weekend. I was so happy to see them together. They took me out to dinner and went we got back, one of them brought me a glass of wine. I was relaxing on the couch when both of them came in the room together with a cake, singing Happy Birthday. “Blow out the candles, Mom.” they laughed. They were both naked and very erect. My older son, Brad,  has a long dick and my younger one, Matt, has a fat juicy dick. They came over to the couch and pulled off my dress before I could say a word. My young one sucked on my nipples like a titty brat. The older went to my pussy and had my panties off before I could protest. I just settled back and let them give me my gift. Total devotion from my boys. Brad buried his face right in my cunt and began to lick it. Matt slid his fat cock between my titties and fucked them, letting me have a taste. It has been so long since I’ve fucked them together. They gave me so much pleasure growing up. Brad flipped me over so he could penetrate me from behind while Matt moved to my mouth so I could suck his cock. They fucked me back and forth like a Mommy sandwich. I was moaning and my pussy was in heaven. They switched places and I felt my younger son really stretch me out. I couldn’t take much more. “Fuck Mommy, please. My sweet boys, I want your cum.” I cried. And they gave it to me all right. One gushed in my pussy while the other one gave me some nice cream for my cake. Mmmm, I can still taste him on my lips. And boy, did we have fun sharing that cake later. What a creamy mess!!! Best birthday ever.

Mommy sucking dick with Daphne

Mommy sucking dick

I know you watch Mommy sucking dick in the hallway mirror. You are supposed to be in bed. Instead you are rubbing your cock while watching mommy sucking this big black cock. You are not being a good boy and you know what Mommy does to Bad Boys. You watch Mommy dominate her her Sissy boys and make them suck big black cocks. You know that Mommy loves have a nice big thick nigger dick in her mouth just as much as she loves having it in her pussy. You also know that Mommy loves watching little sissy fags like you sucking on big cock. You are being such a bad boy, do you need a spanking from Mommy? Mommy will spank your bottom until your little ass is all red. Then Mommy will make you choke on his big black cock getting nice and wet. And he’s going to take that big cock and rub it all over your tender ass, and make you his bitch. No do you want to be a bad boy or do you want to be a good boy and do as you’re told? Mommy loves it when you’re a bad boy.

Mommy Whore Shares Son For Doctor’s Day

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It was time for a check up for the boy. You discover he has on satin panties and ask him about them. Embarrassed he replies that he just loves the way they feel. You admit that he does look rather sexy in them and that they showcase his young cock nicely. You tell him he needs to remove them for the exam. He does and you inspect his parts. You comment that his ass looks a bit stretched and you need to check to make sure everything is ok inside. That is when I notice the bulge in your pants and realize this will not be a routine doctor’s visit.

You use your finger to inspect his ass and decide you need something that can reach deeper to check it out really well. You give me a wink and I know what you have in mind. Since it is Doctor’s Day and you are being so nice, how could I refuse yo this pleasure? Actually, I wouldn’t refuse you anyway. A dirty mommy whore like me gets off on watching her little sissy boy get abused. I watch as you take your cock out of your pants. You use the KY to prepare his ass and your cock. I finger my pussy as I watch you begin to push that bulbous head into his tight little ass. He whimpers, partly in pain, part pleasure. You begin to stroke your cock in and out of his ass. You and he both look like you are in heaven and I finger my sloppy wet pussy even harder. You say that his ass seems to be fine and you need to check his tonsils. You pull out and move to his mouth, proceeding to fuck that sissy mouth with your dirty cock. I watch you and I stroke my clit even harder. I am on the verge of coming when I see you start filling his mouth with your cum. I wait for him to finish swallowing and then sit on his face and ride it to my own orgasm.

What a fun way to celebrate Doctor’s Day! Best of all, the visit was free!

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Phone Sex Mommy Nicolette is a Sissy Mom Too

phone sex mommyI want to be your phone sex mommy! You can be any age you want too! As a P mommy, I have played with sons of all ages.  And I have sons of all kinds. Currently, I have a school boy who thinks he is a school girl! Naughty little boy who likes to wear mommy’s panties.  He had an accident at school yesterday that tore his jeans during recess. The whole school saw that he was in women’s panties and laughed at him. They called him a sissy. He ended up in the principal’s office. I had to go bail him out of jail. I have told him time and time again, he can wear my panties at home, but never at school. School age boys and girls can be very cruel. The principal suggested I get him counseling. Like the principal never stole a pair of his mother’s underwear before. Every guy goes it. Doesn’t mean they are gay or even a sissy. Some boys  just like to feel close to mommy’s pussy. Some like the feel of the silk on their little dicks. Some realize they have little dicks that get lost in boxers so prefer the tight fit of mommy’s panties on their junk. I asked my son when we got home, why he disobeys me by wearing my panties to school? He told me he thought he might be a sissy. I asked him how he even knew about such things at his age, and his response was from you on the phone! He has been listening to me be a sissy mom for all my phone sissies. Luckily, my boy toy husband is very open minded. When I told him that his son thinks he is a sissy, he didn’t shame him or even punish him. He just pulled out his cock and ordered his sissy son to suck daddy’s big dick. Sissy school is in session at my house!

Sissy needs some Mommy Love

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Oh, Michael, you poor sissy. Someone really needs to teach you how to dress properly. That frock you’re wearing looks like you stole it from your granny’s closet. It’s so frumpy and pathetic, kinda like you. I train sissy boys and it looks like you need some lessons. If you’re gonna be a sissy, be frilly or be sexy. Flaunt that shit. But those awful dresses have to go. I see that I need to take you by the hand and give you some guidance.

Taking you shopping was fun but your sense of fashion sucks. I was helping you out of a tight dress when I saw your penis. OMG. I had to laugh. It was the tiniest little thing I’ve ever seen. How can you pee out of a button? I really get it now. You’re not a sissy because you want to be. You’re a sissy because you have no other choice. There’s no way you can ever please a woman with that nub. It would be like jerking off my clit. Please keep it tucked in your panties where no one has to look at it, much less touch it. At least in your fluffy penis pouch, it looks like you have more cock.

sissy maid training

I was feeling so mean after we finished shopping that I made Michael be my pay piggy and buy me steak and lobster for lunch, while she received a cold tuna sandwich and lukewarm tea.  Such a pathetic loser should have to pay for everything. Finally, I ordered him to put on his new princess outfit and handed him a sign to carry.

PLEASE TEASE ME ! GIGGLE AT ME ! LAUGH AT ME ! OUT ME, HUMILIATE ME & PUNISH ME AS I DESERVE !

And I laughed and laughed as people stared and pointed at the pansy fairy faggot…..

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Sissy Mom Nicolette: Springtime is for Sissies

sissy mom springI’m a Springtime sissy mom. What does that mean? It means that as the temperature gets warmer and the flowers begin to bloom, I start to clean house. But in my house, that means something different than just putting winter clothes away. It means getting sissy boys ready for the new season. My friend Gloria has a son who we think was born in the wrong body. He is no man. When he was knee high, he was wearing mommy’s panties and playing dress up in her clothes. I would come over and he would be prancing about in high heels wanting us to join his tea party. Gloria just laughed it off as his experimental stage, but I knew he was a sissy boy even then. My best friend has resisted my pleas to just make him a full fledged sissy. We had lunch the other day, and I begged her to bring him over for my springtime cleaning ritual. She finally agreed. Springtime is for sissies!

sissy boy phone sex springWhen they arrived, I slapped a collar on Derek and informed him his new name was Denise. He appeared scared and aroused simultaneously. Every woman can use a sissy in her life. They make excellent maids, bitches and fluffers. It is when they are in that girl not ever going to be a man stage that they are annoying little whiny ass fuckers. They need a dominant mommy to convert them to full fledged sissy and become their master. They need my springtime ritual. Denise was held down while I fisted her back door pussy. I wanted to pop her sissy cherry while Gloria rubbed her little clit stick with the vibrator. A sissy’s first cum is special. Just as special as a sissy’s first fuck. I let her mommy take her tight virgin ass with a strapon while I fucked her pretty little mouth with mine. Tag teaming a sissy is so much fun. After a sissy’s first fuck, comes dressing the sissy. I had a pretty pink frilly springtime dress laid out with a white bonnet and some white sandals. Gloria couldn’t believe the transformation. Thanks to my sissy springtime ritual, she now has a full time sissy who will cook and clean for her, plus pamper and amuse her; even procure cock for her and clean up her cream pies. A sissy is a dominant mommy’s best accessory. Are you ready for your conversion? Sissy boy phone sex awaits you.

This Mommy Loves Sissy

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All the other girls here are so mean to our company sissy. They love to publicly humiliate him just because he likes to wear cute little frilly dresses and diapees. He has such a tiny cock, he is already humiliated. It’s really more of a large clit than a cock. He spends his time with Mistress Levi. She owns him. Occasionally however, she loans him out to us other girls. When its my turn to have our little sissy, I show him plenty of Mommy’s loving attention.

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At my house, Sweet Baby Sissy has his own little crib set up. I have special onesies for him to wear and I give him his juice in a bottle or a sippy cup. I make sure his bottom is clean and use baby powder on his bum, so he always smells nice and fresh. I even lotion down his skin, so that it stays nice and soft. He even has his own special teddy here that he loves to cuddle. He is such a good boy when this Mommy is sissy-sitting. He never gives me a lick of trouble, unlike my own rebellious ones.

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Sissy loves his Mistress. He loves being dominated and humiliated. But sometimes, he has to come visit Mommy Meredith and get my own special type of Sissy treatment.

An Ode to Mommy Pearl

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There was an old lady named Pearl
who took all the boys for a whirl.
Her pussy, they claimed
put young girls to shame
Cause all the boys got some.

She liked big dick a lot
even a crusty old cock
She took them to bed
and gave them some head.
The lads all loved this old slut.

She loves tight young ass
she’s a naughty lass
But the boys will never complain.

She still fucks them all
and licks their sweaty balls
She’s a lady through and through.
And she’ll never stop
until she makes them pop.
That’s what a good Mommy should do.

Mommy’s Frat Boy

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I pushed the vibrator deeper into my pussy. It felt so damn good. You’d think I’d be satiated after all of the cock I got last night but when I woke up this morning and felt his cum still oozing from my battered cunt, I got all turned on again. He is my best friend’s son. We went to college together and she made me his godmother when he was born. I never expected to be his FAIRY godmother.
I hadn’t seen him in several years while he was away at med school. He was an awkward geeky boy with crooked teeth and glasses. I never even thought about his cock even though I love it young. But when I visited Linda yesterday, I almost fell over when he came through the door. The geek was gone along with the braces and bad skin. He flashed a sexy white smile at me and hugged me. “Nice tits.” he whispered, making me laugh.
Linda had an appt and invited me to stay until she got back. He and I got busy getting to know each other again. We talked and laughed until he looked at me all serious. “I’ve always wanted to fuck you, Pearl.” He reached for me and I didn’t say no. His cock was thick. When he pushed it deep into my deprived pussy, I was a goner, a shameless begging whore. He made me cum twice before he stopped. “Let’s go back to your place.” he moaned. He ate my pussy like a starving man. I sucked his cock and licked him clear to his asshole. Then he was back inside of me, driving me wild. His pistoning hips churned my insides into butter and I was more than ready for his cream. When he finally allowed himself to cum, it was like a scream of pain and bliss.
I awoke to find him gone with a note that said, “I’ll be back tonight, Pearl. I took your panties with me. Tonight, I will show you yet another side of me that I think you’ll love.”
So, it looks like a have a brand new sissy boy on my hands. A mommy can never have too many. I can barely wait to hear his secret. Just in case, I have a big black strap-on lubed and ready for him. It’ll be my pleasure to take that ass cherry.

He Looks Hot In My Pretty Panties

mommy son phone sex I walk into the bathroom and stop dead in my tracks. Standing in front of the mirror is my oldest son with his hands wrapped around a rather large erection. What makes me pause for a moment is realizing he is stroking his cock while wearing a pair of my panties. It is not just any panties either. They are a pair of my favorites. They are a cute little pair of thongs that are purple with pink designs on them.  He looks rather embarrassed to have gotten caught. I don’t want to embarrass him further, but I have to ask what he is doing in my panties. He confesses he loves the way the soft fabric feels on his skin. I guess I can understand that as that is one reason this is one of my favorite pair.
 What confuses me further is that seeing him in my panties is actually making me excited. He looks so hot with his manly cock coming out the top of these girly panties. He is already dripping pre-cum from the tip. Not being able to hold back any longer, I drop to my knees and begin bathing his dick with my tongue and licking up all that sweet juice that is trickling out the top. I tell him how hot he is and how much I adore his cock. Before we leave the bathroom, he gives  me one of the best fucks I had gotten in a while. He fucked my hot pussy with all the vigor and stamina that only youth have, filling my cunt with his baby making seed.  I tell ya, if wearing my panties gets him that worked up, he can wear them every day!