Category: Sissy boy mommy

Sissy Maid Son

Sissy maid training

 

I’m really proud of my son’s sissy maid training, she’s really stepped up her sissification almost all on her own.  Sure, I gave him a bit of guidance to point him in the right direction, but I never broke him down mentally like I did with all of my other femboys.  She’s either advanced this far all on her own or she has another sissy mistress helping her along.  It doesn’t matter to me either way because she’s really happy with herself and her sexy little clitty, plus my house has never been cleaner!

My book club meeting was at my place last week and the girls couldn’t stop commenting on how spotless my house was.  I told them all about my new maid and called her in so I could introduce her to the gang.  They all marveled at my sissy son’s marvelous pink hair and sexy maid outfit.  Even Miss know-it-all Janice asked where we found hot heels his size because she has problems finding shoes big enough to fit her giant hobbit feet!  

The gals had a great time bossing my girly boy around and making him wait on them hand and foot.  Their drinks were always fresh and the dishes were always cleared with a quickness.  The club organizer, Yolanda, liked bossing my maid around so much that her fat pussy got really wet and soaked the cushion of her chair.  Of course that had to be cleaned too, but she stayed seated and made my horny helper polish her puss with his mouth as he scrubbed her spot.

I love my girly son, even if he didn’t clean my entire house.  The fact that he does, though, makes me appreciate her even more.  It’s great for me because someone has to clean up all the cum.

 

Jack off with mommy Regina

jack off with mommyMy pussy aches for you to jack off with mommy. I know you are my son and it is wrong in the eyes of many. But look at you all fine and stocky. And don’t think I haven’t put my hands down my jeans and played with my clit while you were stocking you nice big thick dick. It’s not my fault you left the door open and mommy peeped. How am I supposed to deny myself the pleasure of a young cock being pleasured? Oh, how I wish it was my mouth making you cum. I want to taste your cock so bad. I lick my lips as I moan and cum outside our bedroom door. I hurry away. But I am out of breath and my pussy is throbbing for my son! I have an evil plan. I broadcast some Milf and step son porn to his TV in his room. I can hear him trying to turn it down. I struggle fast to get out of my clothes and grab a towel. I run down the hallway and barge into your room and ask if everything is alright?! “Mom… were you watching this, it’s coming from your phone?”
Look at you all nervous but very erect and naked in front of momma! I drop my towel and drop to my knees in front of you. Im fixing to make my own son cum in my mouth like a good cock sucking mommy!

What Are Your Mom Fantasies?

mom fantasiesI love exploring mom fantasies with callers. Guys have so many different kinds, but they all involve eventually getting to fuck mommy. I cannot blame you for wanting mommy. She is the only woman who loves you unconditionally. She is the only woman who will always put your happiness and needs first too. Mommy does not care that you have a small dick. Mommy does not care that you wear her panties. Mommy does not even care if you like to suck cock. I have three boys and they are all vastly different Mommy’s boys. My oldest son is bisexual. He is with more women than men, but he does like a big dick occasionally. He gets that from me. He sometimes sucks his younger brother’s cock. When they were in high school, my middle boy, would convince his older brother to suck his cock. My middle son is not gay. He was just horny and needed his dick sucked. He tried with his sister, but she told him to go beat off and threatened to tell me. I am glad she did not tell me. It might have changed the outcome of our incestuous family lifestyle. My middle boy is the one who convinced his older brother to jack off together with my panties in hopes I would find out. Obviously, his mischievous plan worked because they are my mother fuckers now. My youngest son is from marriage two and he likes to wear panties. He does not suck dick, not yet at least, but he likes my pretty things. He still fucks me, but we play dress up a lot too. For him, I am a sissy mom too. This mommy loves all three of her boys equally. I have a bi boy, a manipulating horny boy and a sissy boy. I am a good mother to all of them. What kind of boy are you for mommy?

Sissy Maid Training

sissy maid trainingAs a Lifestyle Dominatrix, I really enjoy the experience of breaking someone down through humiliation and shame. I discovered this amazing lifestyle through seeking something in my life that would bring pleasure. If you could believe it, I used to be the Church Secretary and waiting hand and foot on the priest. I have finally embraced the real woman that I am. Breaking free for me through the humiliation and shame was one of best choices of my life.

I do currently have two sissies’ currently under my domination. I like to have two at a time, so I see how they play off each other. Sometimes they share great friendship and other times they are sworn enemies vying for my attention. My longer serving sissy came to me a few years ago. He was the priest that I had waited on hand and foot. The power exchange was phenomenal, and he will always be special to me because he was my first. He is moving back to his hometown to take care of his aging parents. He will be greatly missed.

With that said, I am in search of another Sissy that I can break down to serve me and only serve me for my total pleasure. I require those who I dominated that they be seen and not heard. They are not allowed to speak to me until I specifically ask them a direct question. There are lots of erotic times as you are learning your role as a sissy maid, but you will be meeting my every need which includes everything that would be expected of a housewife like cooking and cleaning. My one sissy always begs to be the one who gets to clean the toilet. I can only imagine what he does with the toilet brush.

If this is something that you would enjoy and living in my home 24/7 beckoned by my call, then please respond as stated in the advertisement. There will be an initial 90-day probationary period where it will be determined if you have what it takes to be a sissy boy to me. All your needs including housing, food, and other essentials but you will be at my beckon 24/7 for however I please. Does this excite you? Please reach out and let’s see if you are worthy enough of this opportunity.

Preggo pussy pounding

preggo phone sexPreggo pussy pounding in front of my sweet and sexy little boy tonight! He came in mommys room wearing panties and holding his pee-pee looking very proud of himself. Daddy chuckled and rolled back on top of me so he could finish dumping his cum in my pussy. I watched you climb up on the bed and told you to suck on mommies big lactating tits as daddy fucked me. That right mommy encourages you to jack your pee-pee and suck my tist while my preggo pussy gopt a nice deep daddy pounding! And when mommy slipped a finger in your butthole and you squealed, daddy laughed as you humped my belly from the side. Oh, how your daddy loves when you come and play with your preggo mommy while he is slow stroking her plump pregnant pussy! Daddy even lifted you up and put your dickie poo in my mouth! Oh how yummies mommies little boy tastes! Pumpies my mouth my sweet boy. ANd when daddy put his finger in your ass you squealed again and mommy took your pink bald balls and duckie poo all the way in her mouth at once! I love when daddy uses your butthole and you fuck mommies mouth with your boy dick! Just think one day you might get to pump mommy’s preggo pussy too!

Dom Sissy boy mommy Regina

sissy boy mommyDo you enjoy having a Dom sissy boy mommy to tame your young lust? You have to know that putting on my bras and panties isn’t what regular boys like to do. Look at you with my stinky sock hanging off your pecker, baby! You’re a dirty son and you love my dirty stinky clothes from my hamper! Did you just lick cum out of my panties! You know that mommy had a date last night right? That is another man’s cum that had dripped out of me onto the cotton part between the legs of my panties! I know you need to be over my lap right now so I can spank the sissy out of you! And as I’m spanking you I’m going to put not one, but two fingers up that ass and fuck that sissy hole and make you cry like the little bitch son you are for me. You want to be a sissy and have mommy sex? Well this Dom mommy is in control of every body function you have! Mommy and her big strap on rules your sweet fairy ass and tells you when you can cummies!

My Son, The Sissy

Sissy mom

 

I’m proud as fuck to be a sissy mom and of my ever blossoming soft little son.  She’s full of surprises, constantly kink hopping to help himself figure out exactly who she is sexually.  I think it’s a smart move for any pan sexual.  How do you know what you do and don’t like until you try it?  I think she’s really found his thing, though.  He’s fully embodied her silly little sissy side.

She absolutely has to get my opinion on all of his prissy outfits.  From frilly pink dresses and maid uniforms to leather corsets and fishnets, she loves to try on his wussy wear for me to see what I think.  She’s great at it, too.  My mama’s boy should get paid to model his effeminate ensembles, she makes them fucking work with legs that don’t quit and an ass I would kill for!  

Of course, being a true sissy boy mommy, I have to show her the ropes and teach her what being a girly guy is truly about.  It isn’t all fun and games for my pretty little pantywaist, she gets the same training as everyone else.  There’s no cutting corners, she has to follow all of the rules and listen to everything I say.  But, just like the others, when she’s been a good girl I’m sure to please her little clitty and let it dribble anywhere she wants.

 

my boy wants the best of both worlds

milf chat

I showed my son how to use a pocket pussy. It was great to get into some milf chat. Boys have an epic imagination, and their mind runs wild. When he told me he was having both sexual fantasies of men and women, I let him know it was okay. My boy can be a sissy who learns to fuck pussies and get fucked in his ass pussy, too. There’s no shame in being fluid, especially in 2022! My boy can be my girl whenever he wants.

I am ready to go out with him and show him how fun being open and ready to try new experiences can be.

Im going to show him how to fuck cunts and ass and get fucked. My strap-on comes in handy for times like this for me.

Sissy Maid Training with Mommy

sissy maid training

It really makes me happy when I get calls for sissy maid training. It’s so much fun to help a sweet sissy like you who loves to be of service to others. I think that’s pretty common for sissies, but usually, it comes in the form of cock sucking or something sexual. But I’m told fairly often that transforming into a feminized maid is a huge dream of sissies everywhere. Their tiny little clitty cocks get so excited when they’re all dressed up in a proper maid outfit with hair, makeup, nails, and of course, a pair of sexy stilettos.

Can you imagine yourself prancing around in your heels with your feather duster? Imagine how cute you’re going to look and how sexy you’ll feel. You will probably even get more than money at the end of your cleaning session if you do a great enough job. Aren’t you excited about that? I wonder what your “bonus” will be? He might let you give him a blow job, but you could get really lucky, and he’ll fuck your pussy really deep and hard. Either way, I know you will be happy with the payment you receive for your cleaning services.

Milky Milf

milf phone sexYou love this milf phone sex whores big milky tits don’t you baby! I get so turned on when you want a drink, my sweet little boy. That relentless greedy sucking and moans make mommy so horny. Even grown men sucking on my milk laden tits gets me aroused. My panties are soaked now and I know that this is wrong, its incest with my little son. That milk spurting out over the sides of your sweet cupid shaped lips as you fondle the other milky tits, I laugh and decide to squirt a little milk down your face! Its time to sit on mommies stomach and put that boy fuck rod right between my milky mammary as mommy pushes them together and let you tits fuck in the milky cream I have lubed up my tits for you. Look at your boy cock fucking mommies titties! Mommys lovers love to titty fuck! Your being a big boy just like the men you watch fuck me! Its time for a mommy phone sex titty fuck full of milk and cock cream!