Category: Sissy mom

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 mom to panty sluts

sissy momI love being a sissy mom to panty sluts that need me. Little Miss princess thought he was keeping a secret from mommy. I knew my sissy son was a faggot long before he even realized it. I think it was in the mist of panty wearing and dildo riding that it dawned on him. One night before I was all the way asleep I remember hearing him moan like a little bitch and cry out mommy. I chucked to myself that It was time to blow his sissy secrets out of the water. But mommy didn’t have to do that. The next morning at the breakfast table he was the last to leave the house. I turned around to get his breakfast. But My sissy boy just started crying. He dumped a box of panties and sex toys on the breakfast table. I recognized each thing as being mine.

I knew where they had gone and was surprised that my femme son was divulging all! Well that settled it, Now I would have to punish this girlie freak of nature. Not that I was not aroused to get the chance! I commanded him to put on a set of bra and panties. I stuck the biggest dildo to the chair. In front of big open windows I made my sissy boy ride that dildo. When I thought I had heard enough of the screaming and begging, I put on my strap-on. The dildo from the chair was then sucked clean! He slurped it like a good slut while I fucked my lil fagot sons mouth! Doing it again and again so maybe the neighbors would see what sissy boy Mommy Regina raised! I am sure my neighbors enjoyed the sissy slut show. I will have to go tell them when next showtime is! 

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

Mom fantasies and now real life for you baby boy

Mom fantasies

I am the sexy mom that inhabits all of your Mom fantasies baby! You know every boy has a mom fantasy, luck for you I will make yours cum true! You know mommy is nothing but a dirty slut! Tell me how you want me baby and I will happily comply mommy wants to be the only apple of your eye, I spread my legs wide and offer you this wet mommy cunt. cum on baby fill me with you nut.

You know how I like it, and that I need it rough. So, pound me hard baby I know you are frustrated. Your little vanilla girlfriend won’t do anything mommy does. She is boring and a dead lay. So, fuck mommy right the animalistic way. Ill fuck you back and make you cum. Baby boy mommy wants you to use this whore hole then slip that large cock deep in my ass. You know you want to, there is no way you can pass it up.

Your mommy is nasty ill push my ass back I want you to breed me and fill me with you seed. Mommy is everything you could possibly need. My ass is so tight and its yours to use and abuse. Make my ass milk you baby use it, it is yours. After you cum in mommy’s round perfect ass cum eat out this cream pie, eat it all up fast. I’m dripping with cum out of both my whore holes mommy is a cum dumpster for you, you know how it is! Mommy son goals!

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! 

wet mommy pussy is ready

wet mommy pussy

Having boys can be quite a challenge. It gets complicated when my boys are older and want to hang out with women other than mommy. My boys are my pride and joy, and I love being there for them. Ever since girls have gotten their attention, momma has a jealous streak. I know that boys will be boys, and I have to loosen up and let them have fun. Besides, I once was a girl who wanted validation from men and to fuck so much. I did everything I could to get attention from guys. We know boys get weak, but I want to make my boys the best fuckers ever. They have gotten the best tips from momma. They know how to eat my wet mommy pussy.

Sissy training phone sex With Mommy

Sissy training phone sexYour mommy has a task for you baby. She wants to do Sissy training phone sex and for you to put on this cute little blue dress that she has on. I’ll take it off nice and slow for you, that way you can see all of your mommy’s body.

Good job sweetie! Oh, no, you can’t be talking that deep baby. You’re just a little girl! Train your voice more for mommy. Now mommy is going to cage your little cock and it’s going to stay on all day. A caged sissy, that’s what you are.

Mommy’s little pussyboy. Let’s get you your favorite wig now, baby. Oh! Aww, you’re already getting hard from this. My little sissy is so pathetic. It hurts? That’s because your caged baby. Now let mommy put on your favorite wig.

Look at how pretty my baby is for mommy! What a good boy. Try not to make a mess on mommy’s dress, honey. I know that you’re leaking pre-cum outside your cage. If it gets on the floor you have to lick it up. Hehe, I love training sissies.

They’re all so helpless and adorable. As your mommy I will make sure that you get the best training out there, and I will fulfill many desires from my sissy little girls. You’ll be a good girl for mommy, won’t you?

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.

Sissy Training Mommy

sissy training phone sex

Watch as I get filled with his big black cock. Look how good he stretches my wanting milf pussy as I ride him. Doesn’t big daddy’s black rod look so yummy? It’s glistening wet from mommy’s glazed twat! We are about to train you on how to be a good cock sucking sissy boy for mommy. You never had bbc before but if you love mommy you’d suck big papa off for me. Make you will do a good job and lick up all Mama’s sugar off his stick! Make sure your get all the cream off of his big black nuts too baby boy! Dark meat is so juicy, isn’t it?

Wait until it fills your tummy up! It’s time to show papa what a good sissy boy mom I am.

Mommy is gonna spread your cheeks and let this big dick daddy stuff your hole! Are you ready, baby? Just relax and let mama and papa take care of their cock hungry sissy slut!