Tag: sissy training 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 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! 

Jack Off With Mommy Reggie

jack off with mommy You know what time it is! Jack off with Mommy Reggie and see just what dirty fantasy we can conceive. My own darling sons can vouch for my expertise. I have one son whose big cock I can’t get enough of and the others whose little clit I love to tease. Both mommies boys satisfy me in ways that a boyfriend or husband can never. A mother and son’s sexual relations are always heightened by the fact that they came out of my vagina.

Those cute little dicks slid right through my birth canal. It’s a shame that more men do not get to fuck that hole that they were born out of. Knowing that your son worships your big fat titties and round ass gets so exhilarating. I never asked to be this way it was a natural foundation of mommy phone sex seducing.

mommy phone sex seducing

 A very fertile ground for me to consume and be injected with loads of hot son cum. Even though both of my boys penises are very different and so are their attitudes and actions I love them the same. Well my little dick son be able to fuck me until I cry and Giggle, no. But he has other kinks that I can accelerate. Such as being a sissy prissy little baby in floozy dresses and diapers. 

Or made a humiliating sissy slave to clean mommy out after a good two man fucking. In essence I have two daughters who are very willing to participate in these training exercises. Both girls becoming accustomed to lust for big cock and sissifying the little bitty fem boys! Momma is here for you. Come snuggle or fuck or use my wet mommy pussy. Just be aware sometimes Mommy uses her boys to make her own self very fucking satisfied!

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

A deep dive into my wet mommy pussy

wet mommy pussy

Last year when I was trying to fit in with my new stepdaughters, I had allowed them to have a Halloween bash in early October. I know, weird a Halloween bash in early October, but hey, weirder parties I’ve hosted.

Coming into teen girls’ lives is quite complex and a little complicate,d but as soon as they heard the words booze, they went ballistic. They suddenlyy thought about all the weed and alcohol I would allow them to indulge in and were happy as clams.

It was a night to remember. I had fun with a few horny teen boys. They all wanted to party with the excellent step mom. Diving deep in my wet mommy pussy was all it took to get my party going, making me one nasty slut.

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! 

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.

Sexy Mommy Does Sissy Training Phone Sex

Sexy Mommy Does Sissy Training Phone Sex

Your 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?

 

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!