Tag: sissy boy phone sex

Only The Best Sissy Mom Stories Involve Cummies!


Sissy Mom

There’s something near and dear to my heart about being a Sissy Mom. I have a few sissies in my personal life that I really enjoy getting to spend time with. I cherish every moment I get with them where we snuggle and cuddle, play dress up, and even get a little naughty together.

My favorite experience was with my sweet baby sissy Jasmine, she’s got the prettiest dark black hair, that I just love to run my fingers through. One day she was sitting in my lap, cuddling me when she decided that she wanted to take it just a little bit further. Pulling a cute little pink butt plug out of her diaper, she giggled bashfully asking me if I could teach her how to use it.

Laying her down tenderly on the couch next to me, I carefully undid her diaper, spreading her legs before plopping the plug into her mouth. “Suck on it little one, make it nice and wet,” I said smiling warmly as I guided the plug in and out of her soft pink lips.

“Such a good girl!” I called out motioning for her to bed over as I slowly began pushing the plug nice and deep inside of her. Her cries made me so happy, my pussy growing so wet as I continued playing with her. My hand reached down as I began to stroke her clitting.

“Make cummies for me little one, and I’ll teach you even more!” I cried out as she began to squirt her load into my hand. Next will be learning how to take a real cock!

 

Wet mommy pussy for ABDLS

wet mommy pussyNothing Gives me a wet mommy pussy like Adult diaper lovers. Bring your full Huggies, and adult baby needs. As a Mom four times over and an ABDL fetish mommy, I have plenty of experience. Filthy piss and shit-filled diapers and pull-ups are part of my daily life. And these huge milk jugs are perfect for a lactation specialist feeding frenzy. Come into my world with oversized cribs and highchairs designed for a big baby! Let mommy change you and wipe you clean and give that cock head a nice big kiss. I know many of my ABDLS have a small little peeny and that is completely okay. I also adore big diaper bulges and men who love sitting in a slimy warm gooey diaper for while they herk for mommy Regina. There are many layers to the Adult diaper lifestyle. I know all about pretty little girlies in frills and lace who need to misbehave and get spanked by me. I would love nothing more to show you off to the world. Maybe you have no clue you’re supposed to be mommies, little baby girl. That’s when I take a strong hand and force you over to my diapered and age regression play times. Mommy Regina is the ABDL lactating phone sex Momma for you.lactating phone sex

Sissy Boy Mommy Means Business: Fuck Around and Find Out What I Can Do

sissy boy mommyWith a sissy boy mommy, you cannot fuck around, or you will find out what happens. I am a dome mommy. I am more loving and nurturing, than ball busting with my offspring; however, I have been known to be a ball buster with disobedient sissies. I have a few sissies who see me on a regular basis. All of them friends of my oldest sons and daughter. They love being a sissy boy for a mommy like me. I understand sissies. I know how to make them feel special and not judged. They can play around in my panty drawer, and I can even fuck them with a strapon if that is what they want. I am stern though and I have rules. Break my rules, fuck around with me and you will soon discover what a bad ass sissy boy mommy I can be..sissy boy mommyTrevor is my oldest son’s longest friend. I knew the boy when he was knee high. I knew he was not like other boys. He was always spending time in my room going through my panty drawer. He was not as much interested in smelling my pussy as the other boys. He wanted to wear my panties. As he got older, I could tell he was a sissy. I knew he was a sissy boy before he did. Twenty years later, he recognized what he was and sought advice from his best friend, my son. My son told him to talk to me. Trevor has been coming to me for over two years now. I do not see him regularly, but he is good for once or twice a month. He Venmos me some money, and I give him some sissy training.

sissy boy mommyHe has master dressing for me. I have taught him how to dress for his body type. I even showed him makeup techniques and how to do his hair. I worked with him using dildos to learn how to suck cock and take cock in his sissy hole. Covid hit and we could never get to the glory hole. Then when things were flowing again, he fucked around. Gave me one excuse after another of why he could not go to the glory hole with me. I am a sissy boy mommy. You fuck around with me, and you will find out what I can do. Since Trevor would not go to the glory hole, I brought the glory hole to him. I invited 10 men over with huge cocks. A few different races too. We had a glory hole session in my living room. My sissy boy had to suck 10 cocks, a few times over. He protested but I told him he fucked around with one excuse after another and had to pay the price. He swallowed a gallon of cum. But now he is a full fledge sissy boy. Who wants trained next?

Sissy training phone sex with Mommy Penelope

Sissy training phone sex

Sissy training phone sex with sweet Mommy Penelope. Have you been wanting a sissy boy mommy to make you the best slut you can be with Sissy boy phone sex? There’s nothing I want more than a sweet little baby to call my own and treat like the cutest littles sissy slut imaginable!

Come right over here and crawl in Mommy’s lap sweetheart, let me show you just how much fun we can have together. Cuddling and treating you so sweetly, and so nicely while I give you all the love and kisses. That’s how you deserve to be treated, having you so close, rubbing your little sissy clitty.

The only thing I want you to do my little love is to come to make sweet sweet cummies for me while I play with you. Mommy Penelope has laid your pretty little sissy outfit out for you, and I’m ready to show you how good little sissy babies are supposed to be treated.

Sissy boy mommy

Best Big Sissy Boy Sister Ever!

Sissy boy mommy

 

When I decided to start sissy training my son, I didn’t know that being a sissy boy mommy would be so beneficial to the entire family.  I just thought it sounded like something fun to do with my gay little boy!  Ever since I sissified my son, not only did it turn him into a real daddy’s girl, but she’s been the best sister to my other daughters that a mother could ever want!

My femboy is my oldest so, of course, all of her younger siblings look up to her and she is an absolutely perfect big sister-bro.  When they want to dress up and try on her slutty clothes, she always makes sure to give them the least cum stained stuff she has to play with.  When it comes time to put on makeup, their sissy always shares her skankiest color palettes with her younger slutty sisters to be sure to bring out their true inner whores.  I’ve never been able to put on makeup as good as she does, I’m kind of jealous!

The funny part is watching her get turned on as the littler girls get naked and change.  Her girl-cock gets hard every time they all hang out so one, if not all of, her sisters is always happy to lend a hand and let her get her femboy family fuck on!  I love watching them, she works over those young teen holes and mouths just like her father.  Strong and commanding yet sweet and endearing, and always certain to make his fuck toy cum!

I love all of my girls but there’s something about your first born that will always hold a special place in your heart.  She has the perfect attitude as the eldest sibling, the perfect slutty style as my prettiest girl and the perfect cock that makes every pussy or ass it fucks have core quaking orgasms!

 

Sissy Christina Takes Vegas

sissy boy mommyMy dick eating sissy wants to get pimped out in Las Vegas & my Mami friends are so ready to play! Sissy Christina would do anything to have her hot pink snatch obliterated by a big black daddy. While we are away, Christina will be my sissy boy mommy bottom for the weekend. When we get to the strip, Christina will be wearing nothing but a neon green g string and a cheetah print tank top! I need everyone to know this bitch came to Vegas to make secrets and get creampied! When I introduce the ladies to my sissy they are going to want a pussy licking demo to see if she is worthy of getting Mandingo dick. As pedestrians walk by they’ll see 4a flock of big titty Latinas taking turns face fucking a little dick sissy! If her mouth works well, we will pull out our phones and dial up the black studs we use to fill our holes. Men are dogs so I’m sure they’d love their new fuck meat! Sissy Christina will finally get all the attention she desires when their multiple nigger dicks are slapping her in the face! These hung horses don’t have time to wait and will bombard her with all the dick she can take. When we are done with her she won’t be able to sit down for a week! 

Anal Sexy Mommy Gets Her Wet Mommy Pussy Licked All Night

Everyone loves a Cock sucking mommy, but they love an Anal sex mommy even better. It makes every Big black stir in their pants. I use my Huge tits to lure them to me and once they see me bend over, they go wild.  Once they get me alone the first thing, they want me to do is choke on a cock. Then they make sure I use my tits to get titty fucked. Once their big black dicks leak, they want me to bend over and get ready. What they don’t know is i stay ready to be an Anal sex mommy. He rubbed his BBC on my cunt getting it wet and gooey from my juices, then with one hard push he shoved his cock in my ass. He fucked me as he called me a good Anal sex mommy. I felt him stretching my asshole open and I just rubbed my clit. It made me be able to enjoy every inch of his BBC in my ass.

Anal sex mommy

He didn’t stop until my asshole was full of thick cum. After I got home, I made my sissy son clean my cummy asshole and finish me off by licking my wet mommy pussy all night.

Sissy Maid Training For Sissy Mommy Boy

Mommy was giving her son some sissy maid training.

Sissy maid training

When my boyfriend with a big black cock came over. He dragged mud on my floor from his boots and right away my sissy boy showed how he has been trained right and came out in his made outfit ready to clean. He bent over, exposing his crotchless sissy panties as he licked the mud of those boots. I pulled my great big mommy tits out and my boyfriend started sucking them. I signaled for my sissy boy to come over. I told him to be a good sissy slut for mommy and suck new daddy’s dick. He came over and I guided my boyfriend’s cock deep into my sissy boy’s mouth. Watching my son sucking his new daddy’s cock gave me a wet mommy pussy. I started fingering my cunt hard while watching but I wanted more. I pulled my son’s face off his new daddy’s cock and rubbed my ass on it. My boyfriend’s big black cock was wet and sloppy, he pushed it into my asshole. My sissy boy watches me be an Anal sex mommy. He loved watching mommy get fucked in her asshole by a big black cock. I grabbed my sissy boys face and pushed into my cunt as i got my asshole fucked. I came so hard my pussy squirted all over. That is when my boyfriend started filling my asshole with cum. My sissy maid son spent the rest of the night cleaning our cummy mess up.

Woken up to be a Sissy boy mommy

“You asleep?” I got woken up by my son shaking my bare tit with a firm grip, his frilly dress showing him in a frankly adorably pretty light that had me excited for being a Sissy boy mommy from the word go. I knew he had something fun in mind, so I pushed myself up immediately to give him a bright smile. Did he want me to suck the cock of my little boy? Did he want to suck some cock and needed me to go find some? Was he touching my tit because he wanted to fuck it, I’d love to give him a titfuck with my great tiny tits. They’re good for squeezing, for rocking, and I have more than enough free space to suck while I’m at it. A lot of thoughts raced through my head all at once, but it was him that gave me answers. He climbed up onto the bed and lifted his dress, revealing his precum dribbling dick and sparkling pink panties. He pulled the blanket down and got up onto my chest. I wondered if he wanted a Cock sucking mommy as I looked to the side at my most recent client resting peacefully after a night of heavy fucking. Then I glanced back to take in my cute boy – the bow in his hair is just a really nice touch – and gripped his hips. I couldn’t protest the situation, that’d wake my client, I couldn’t scold him, that’d wake my client, and I couldn’t physically stop it as that’d wake my client. As far as I was concerned for the sake of my professionalism I had to lay here and take my son’s feminine yet huge dick pumping into my thicker lips and accepting my tongue as a gift. Somehow, that was hot as absolute fuck. I couldn’t think of a hotter situation than having him fucking away at my face, his meat setting tingly fire up and down my cheeks and forcing me to hold in my client waking moans. I sucked knowingly, waiting for him to blow his load and coat my tongue with thick white cream, and held him close while doing my best to keep my body still. My heart wanted to beat out of my chest at the sight of him enjoying himself so much with my slutty Mommy whore body. It made me soaked. I also wondered if I could get him to suck my bedmate off while I sucked him off, like a really sissy boy should.

Caught My Sissy Nephew Sucking Cock

I walked into my nephew sucking a cock. When they saw I was there they didn’t stop.

Sissy boy phone sex

His friend’s big black cock was ramming into my nephew’s mouth. It made my pussy twitch, and I grabbed my nephew’s head. Shoving it down, making him choke on his friend’s BBC. I pulled my big mommy tits out and made his friend nibble and suck on them it made me want to just get fucked. I pulled my panties down and told them to fuck me. As my nephew’s friend rubbed his cock on my wet mommy pussy hole my nephew was licking his asshole. It made his cock twitch inside me. I yelled for my nephew to lick his ass more and when he did, his friend pounded my cunt hard. I rubbed on my clit bouncing my pussy back on his young BBC. When I started cumming on his cock I felt him tighten up and then I knew he was about to fill me up with nut. My nephew noticed he was giving me a big creampie and pulled his friend’s cock out my cunt. He wanted to taste his friend’s nut. Since he wanted it so bad, I made him clean my cummy cunt like a good sissy maid.