Tag: sissy boy 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.

Suck It Up, Sissy Boy

Sissy boy mommy

 

I am the most hard-core and intense sissy boy mommy by which your wussy ass will ever have the pleasure of being owned.  My sorry little sissy slaves do exactly what I say because they know that if they don’t their asses will regret it in every way imagineable.  I have torture methods for disobedient sissies that would make your fucking head spin.  I might clamp down those puffy nips, hook them up to a few fuck machines and stuff them full of fake black cocks, coming at them from every direction, until they scream out in agony and dribble cum out of their laughable little clitty’s.  To get more out of them, I’ll strap them up to a milker and force load after load of runny sissy splooge out of them that they know I’ll make them drink.  My pathetic little piss ants better do exactly what I say or there will be hell to pay. I’m gonna dress you up like a pretty little whore and make some money off your wussy pussy and that tight little ass of yours, you pathetic sissy bitch.

 

Flock of Sissies

Sissy boy mommy

 

I fucking love being a sissy boy mommy!  I have a whole flock of sissies at my beck and call just waiting for me to give them some depraved attention.  They love being my wimpy little whores and dressing up sheerly for my enjoyment.  I make them dress themselves in front of me in some mismatched slutty panties and old lingerie while I describe to them how every piece of clothing they put on will be torn off of them.  I slap some shiny pink lipstick on their thin lips to make their milquetoast mouths look like a target for all the thick cocks I’m going to make them take.  Their mushy maw’s and wussy pussies get stretched and abused by anyone and everyone that I choose.  They gladly do whatever fucked up things I ask and I can tell they like it because, when I laugh in their pathetic little faces, their little clitty’s get so hard!  They don’t get to touch them, though, not unless I say they can.  They’re my sissies, they belong to me.

 

Phone sex Mommy Advice

phone sex mommyWhen he called this phone sex mommy it was for advice. He was in his 20’s, successful and living with his first girlfriend. She was much older than him and had taken his virginity. My caller was anxious that he couldn’t keep up with a woman much more experienced and older. When pressed he confessed that he had asked her about her fantasies. And that had led them to a MMF threesome. You guessed it she wanted to use her young boyfriend to service cock while they both got fucked. Turns out they had already attempted this once and my poor young guy was under the impression she just wanted to be fucked by two men, and have him possibly watch as she got hers! But he was sucking and fluffing that cock for him, in an almost forced way. And now after this affair of two men and a Milf he was curious what she really wanted from him. That prompted his call to this sissy boy mommy. She wanted him to be fucked by a BBC and used as a cum catcher for a bull cock. I giggled as I knew where this was going. This young man who had only been with this Older woman, was about to be turned into a sissy for his Ladies pleasure! Of course I encouraged him to go through with it, because a bisexual man is so fucking hot! Don’t you think so, too?

Sissy Boy Mommy Play

sissy boy mommyThis sissy boy mommy is on the Rag for Christmas and My son already knows what’s up! Mommy needs her pussy cleaned up and her cramps relieved by his mouth. And you know every time I change my Tampon, he needs his boy pussy plugged up too. But it’s more than that. I always have to pee and he drinks it with such gusto! Drinking mommys pussy juice is more than my cum and mommy Honey for him. I push his little face deep in my cunt and grind so he gets every last drop! I had my best milf friends over today. And I explained that my son was a little different than most and he needed to have his period right along with me. My friends were delighted that I took the time to properly train him. But they wanted to show off their way of taking care of their needs. One was was more interested in the new strap-on I had bought for our Christmas day activities, And wanted to fuck him like the little whore in heat he was. I was so wet at the thought of another woman fucking my son with her mommy whore dick that I just had to let her be the first to strap fuck my little sissy slave son! I had one request, to suck my son off as she had him on his back and he ate my pussy! So as I brought him in the big bathroom for his changing, one of the mommies showed him how she changed her extra super tampon with a hairy milf pussy and the other strapped up to fuck his boy pussy. Mommy and her friends would love to do some sissy training phone sex with you, two mommies are better than one!