Tag: sissy training phone sex

Sissy Teen Son Learns to Ride Cock

Sissy boy mommy

 

I never had a daughter and always wanted my oldest to be a girl. My oldest son is completely masculinized but my younger son still has a very feminine body. He is light, skinny and very pretty. I got him some cute little clothes that I thought would look good on him, but he showed me an outfit that hentai women wear in something called anime. It was a cute little maid costume, so I bought it for him, and he looked incredibly sexy. I then got a bit sad that I would never be able to teach my daughter how to ride a cock. My son then told me that I could teach him how to ride a cock. I got out my dildo with a suction cup at the bottom of it so he could ride that cock with his tight asshole. I lubed it all up for him and slowly lowered his ass onto the dildo. I held the bottom so he could have some control and told him to ride it faster and take it deeper. With a bit more training, he will be an amazing sissy cock rider.

Sissy boy mommy Shenanigans

sissy boy mommy

Sissy boy mom Shenanigans for my youngest son. I get such an ego trip when it comes to my sissy son. He worships me in every way one can. Now, my son has always been soft and effeminate with a skinny dick that never quite grew much hair. He was the hardest for me to wean off my tits and still carries the moniker of mommies titty baby. He is so different from his brother. SPeaking of, I caught my sissy boy sucking off his big brother’s dick yesterday.

At first I was more than a little shocked. Judging by the way he was deep throating and my oldest moans he was doing a great job. I was quite proud that I had taught my son to suck his ass juice off of mommies handy dandy strap-on dildo! I continued to put the laundry away and he never missed a beat sucking his brother’s dick. My oldest has a smug smile on his face. I winked at him and held my finger up, to say I’ll be right back. My cunt was dripping as I ran to get properly dressed and grab my ass fucking ass-essories!

Barging into that bedroom mommy had her strap hanging in her hand and a paddle in the other. It was a sight to behold as I was Mommy mistress dressed in black and ready to make my sissy son into a big brother and mommy sandwich! Caught between his brother’s cock cumming in his mouth and my dick, we made that little boy whore squeal like a pig!

Trust that this mommy takes Sissy boy phone sex to the next level with big brother and you! 

Lactating phone sex and Adult diaper lovers

lactating phone sexWe all know that Lactating phone sex and Adult diaper lovers is a match made in heaven! My huge jugs hold so much mommy milk! Not to mention my Mommy ABDL skills, You can cum to me anyway you need to, my love. I know you love the way a plastic backed diaper crinkles when you move. Plastic pants on top of a nice squishy diaper makes you ache to call your mommy.

No matter whether you’re padded or you’re just in a cloth diaper Don’t be afraid to make big messies for this ABDL loving Mommy! I bet you will be surprised to find out that this Mommy wears pull-ups on occasion and sucks on a sippy cup. Now having four babies will destroy a bladder and while I started out using Always brand incontinence briefs, I soon reverted to using a large overnight pull up. And I’m not ashamed to say that I have shit and pissed in my pull-up on calls with adult diapered men and women.


I do say it’s a nice change of pace for mommy to be babied once in a while. Does that classify me is a switch ABDL? I would say I’m 25% a diaper/pullup wearer and 75% lactating and diaper changing Mommy. I know that men who like diapers and some women 😉  may have medical issues that they have crafted into a nice sexy little fetish. Perhaps it’s what started it all. A back injury leading you to have a nice shitty or pissy accident right in front of the nurses and discovering the pleasure of being changed. Home health Care nurses that are sensual and loving creating that safe space for you are part of that too.
Even if it’s just that you like to be a nurse and jacked off in a nice clean diaper until you have big cummies for mommy there’s no shame here. I am very vocal and open about my love for ABDL Mommy phone sex and I hope that you will come see me my big boy. Mommy Reginas Leaky Huge tits await your mouth!

Sissy boy mommy lover gets fucked

My youngest step son is a big Sissy boy mommy lover. He worships mommy and wants to be just like me. My boyfriend was over and my sissy boy got caught wearing my panties. To our surprise, his round ass looked good with a thong on. I bent him over my knee and spanked and told him he can’t wear my panties without permission.  As I spanked him my boyfriend came over and laughed as he shoved his cock in his mouth calling him a sissy mama’s boy. I just kept spanking him as he sucked my boyfriend’s dick. I moved the thong to the side and told my boyfriend to fuck my sissy boy and show him watch bitches who wear sexy panties. He got behind him and mommy aimed the hard cock to my sissy boy’s pussy and let him get fucked right on my lap.

Sissy boy mommy

My sissy boy took it like a champ because he loves mommy. When he got filled up mommy told him to keep his panties on and get dressed for bed. That made my wet mommy pussy excited and it was my turn to get fucked.

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. 

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!”

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