Category: Sissy boy mommy

improvise when horny

Sometimes you have to improvise when you are hot and horny. A hot mommy like me loves to put her youngins to bed and find the nearest vibrator. Unfortunately, it was out of juice, and I couldn’t get my mind out of wanting juicy big cocks. All I could think about was being a slut for a nice hard cock, and since my vibrator wasn’t working for me, I had to go and grab the next best thing, a big juicy plump cucumber.

My wet cunts began to get all drenched. How could I say no to that yummy feeling? I was so wet that I began to slip it in, and deep down inside, it went. My cunt was so sticky icky damp, and ready for the climax. Dont you want to jack off with mommy too?

 

jack off with mommy

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.

Phone sex Mommy and Me period play


phone sex mommyMy boy knows that this is my phone sex mommy time of the month. I get up early after starting my period overnight. I know that my son has to be on time for school and we need a little extra time for him to help me clean up. It’s a monthly ritual that I am very much enjoy with my handsome boy. I wake him up and let him know that Mama has started. Follow me into the bathroom he grabs a super plus tampax. First thing is first Mommy needs her pussy cleaned up. “That’s right use that tongue to get mommy off to help her with her cramps. And then pull my tampon out with your teeth and clean me up!’ I shudder out. It’s such a bonding experience for my son to help me with my monthly cycle.
And it isn’t my fault that I always have to take a pee after I get my tampon out.  That Oragasm from his tongue on my mommy hole and clit didnt help my bladder either.  “Drink up baby Mama knows how much you love cleaning her up!” I giggle. 
And now it’s time for my boy to have his period. Using a little bit of mommy’s flow and a nice big tampon with a little bit of lube on the end; I give my boy his period. Now, some period panties for him and off to school he goes. And I just love hearing his stories about how the nurse helps him clean up when he needs it! You know my boy is so good at helping clean up her hairy milf pussy too. It seems we all have synced. That’s a very good thing for this mommy phone sex messy cycles! Today when my son came home I was happily humping my strap-on tied to the kitchen chair. Oh what a fucking bloody mess it was too but it felt so good and mommy was just so horny.
I make my boy  clean my mess up with his mouth, including this pussy! “Do you know what I have planned for you?” I tease him.  “Do you see those towels laid out on the bed? Well go on and lay on your back so mommy can take your tampon out and fuck you!”

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 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

Sissy Maid Training From Anal Sex Mommy

Since i am knocked up now I need much more help, i make my sissy boy do so many things for me. Prefect for Sissy maid training, he made sure to pick up after me and clean my messes even shave my Wet mommy pussy. 

Sissy maid training

One night I was so horny that two of my favorite bulls to come over and fuck me. They took turns fucking my mouth and cunt hole. I squirted a few times and they still had not busted yet. I decided to use my sissy boy, he will be perfect for a good bull nut milking. I called him and he was still wearing the sissy panties I gave him. I told him to help mommy out and milk her friends. Like a good sissy whore, he got on all fours and started sucking cock as I guided the other big black cock in his boy pussy. I’m an Anal sex mommy so I love watching a dick go deep in an asshole. He got fucked as mommy watched making sure he did a good job. One after the other my bull friends started cumming. My sissy boy tried to swallow every drop. All I could see was the cum dripping out of his sissy gapping asshole. Mommy made sure her sissy boy cleaned their cocks with his mouth before they went home. After that she went to sleep with her sissy son cleaning her cunt.

Wet mommy pussy

Wet mommy pussyWet mommy pussy what should I do?  I cuddle my strong little boy deep within my cunt. With your hands between my legs feeling all of mommy’s warm wet pussy. It’s only natural for you to get a hard-on with these large breasts in your face motor boating mommy. Mommy starts to rub that large meat stick in between your legs grabbing that big bag of yours. As you start nibbling on my erect nipples. I commenced stroking your dick until you start to precum. Mommy’s wet pussy will make you feel really good. I lift up my skirt and sit on your face mommy’s wet pussy dripping all over. Mommy’s swirling her little hips all over you until she busts all over your face. Wet mommy pussy is always the best.

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!