Category: Sissy mom

Sissy Son Dressed Up and Shown Off

Sissy boy mommy

Mommy loves taking care of her beautiful sissy son. I love to dress you up like a little doll and parade you around our family and friends. I remember the first time that I dressed him up. He looked like a dream. I got him a nice, cute blonde wig braided into pigtails. Then, I put on some doll makeup on him to emphasize his features. After that, I got him a school girl outfit to put on. Now my young one looks like the sissy that I have always wanted. She looked perfect and I brought her to the family gathering. Everyone told me about how cute she is and how they wish they had a daughter like her. You are so cute and girly. You even acted like a cute girl, giggling and having fun the whole time. You are the perfect little sissy and I’m going to dress you up everyday so that I can show how feminine you are. 

Mommy Whore Size QUeen

mommy whore
Mommy whore Size Queen Regina Loves Bisexual men!
I love my bisexual sissy whores who love little ass and pussy! One of my favorite new clients is a very fluid man who appreciates superior black cock. And this sissy boy has a nice big fat pole! That’s right baby you can like BBC and still be hung, wink wink! On the bonus side. He’s got a nice sweet young sister that he recently found out was a whore just like he is. It’s a typical: I played with my little sister and molested her a little bit and turned her into a size queen. Oh how this Mommy enjoys a sexy sister that just got out of high school. My pussy is wet because and she’s already getting pounded by BBC.
Not that she hasn’t for a couple years now! But One night her big brother caught her in the act of riding a big donkey dick. She offered to share. Ever since then they have been tag teamed by a black football player. That’s a lot of cum for both of them going on 2 weeks now. I’m sure his big black cock is happy to have some tight sissy ass and young pussy to play with. I know I get so wet for that big Bi cock! I would ride my sexy sissy while he has a mouthfull of BBC! So believe me the sissy mom loves p-men and incest. Layer up our hot sessions by adding some big black cock love.

Girl Time for Christmas

Adult phone lines

My girls and I don’t have any big plans for Christmas, we’re just going to sit around, hang out on some adult phone lines and watch Christmas movies together while we enjoy each other’s creamy cunts.  Nothing crazy, just taking it easy and sleazy this holiday season.  We’ve all had a hell of a year and we’re looking forward to a little slit rubbing rest and relaxation.  We deserve it!

My husband is going to be away on business and my sissy boy son is off somewhere getting his butt stuffed full of cock, so it’s just us girls this year.  We’re looking forward to it, we never get to have a hole pleasing holiday with just us gals, it’s going to be great!  I’ve got it all planned: festive snacks and treats for when we get the munchies between fingering sessions, a long list of Christmas flicks to watch and enjoy while we play with each other’s drippy pussies and tons of lube for all of the sex toys we’re going to try out on each other.  It’ll be great, just you wait!

Don’t tell them but I got each of my girls their very own strap-on, this year.  If all goes as planned, I’ll be showing them how to use their new pussy pounding crotch appendages and we can fuck our way out of Christmas and toward the new year.  With any luck, I’ll be taking one or two of them while we watch “Scrooged,” I love Bill Murray so much!  When the guys get home, they’ll have a hell of a holiday surprise waiting for them.  Their assholes will be tickled pink for sure, I’ll make certain of it! 

 

mommy whore and her girls

addison

I am a mommy whore. I have had quite the life. Everyone who knows me knows I am sexual and a proud Brazilian with greek/Sicilian roots. When I was a young girl, I was always in love with my trainer growing up. I grew up in a sports-loving family, and my parents pushed me to keep the Brazilian in me alive by taking up some Brazilian jiu Jitsu. The trainer was quickly in his late 20s. Lorenzo was delicious half Italian station have Brazilian with a god physique. My teen self swooned and couldn’t get enough practice. Not only did it help keep my parents happy, but it was fantastic to see the progress and my hot body transform into the scorching heat. Now about 20 years have passed along. I have tried a bit of everything to get my abs back. When I heard Lorenzo was back opening up a studio, I had to inquire about one-on-one lessons. He was excited to train me, and now I have hot twin daughters that would be joining. After training, we all stayed and chatted. Lorenzo was not only eyeing the hell out of me, but he was also looking at my girls. He kept saying they were carbon copies. Minutes later, we divulged how my parents never knew how we would hook up. We got a little stoned with my girls and decided to keep story time going and even mixed some hard seltzer that would not intervene with our workouts.

We all got riled up and horny, and Lorenzo kept telling me how hot it was that I was so fertile still and could get knocked up at the drop of a hat. My girls, too, are excited to get knocked up. The topic was great because we ended up making a pregnancy pact. Lorenzo wanted to grow his new coaching studio. He tried to focus on healthy pregnancies that incorporate martial arts and working out physically in the gym studio and sexually. 

The bright idea was quite illuminating because he wanted us all to be his breeding babes. A breeding whore is great, but three is even better, primarily if they are related. In no time, we were all convinced. Plus, I’ve always wanted that cock to cream in me and get me knocked up.breeding whore

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!

 

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!