Category: Sissy maid training

Mommy’s Creamy Gangbang!

Jack Off With Mommy

Sometimes a Mommy whore like me just needs a cunt full of cum for her little ones to lick clean! I love being a hot mommy slut who hosts filthy gangbangs in her trailer, My little angels get so excited when I tell them that I’m having a lot of friends over to play with us. My little girl gets all wet when I play with her cunt and wash her in the shower before dolling her up in one of mommy’s slutty lingerie sets. My little boy strokes his cock all day thinking about all the attention he will get from mommy’s p-daddy friends! We can’t wait until our guests arrive to stuff mommy’s thirsty cunt and her angels sweet little holes full of thick p-daddy dick!

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.

 

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.

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.

 

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.

 

I love bar hopping

wet mommy pussy

I live close to downtown, so I have the convenience of going bar-hopping whenever I like. My husband is gone, and I tend to make this wet mommy pussy get action as soon as he checks out.

I enjoy finding the right guy to fill me up and use me for a few hours. Usually, I’m not done. I make my way to a few bars and get my fix before I get back home. Sometimes I take my sweet time and don’t go back home till a couple of days. My offsprings know the deal and know how mommy is. They know mommy has to get her to fix before anything.

I have trained them well and hope to see them all follow in my footsteps. Life is about enjoying yourself, and sex, drug, and magic is all a part of mine.

Sissy Boy Mommy And BBC

sissy boy mommyAs a sissy boy mommy I know all about the wants and desires of men who desire to transform into beautiful women. Women who were once classified as men who need a big black man to bring out the woman in them. I, as a Cis gendered female love BBC and am not shy about my experiences and often share dick with my own sissy sons. SO it cums as no surprise that I am a promoter of transgender rights and sexual experiences. I just had the most beautiful experience with Sissie TJ who is an older Trans woman who gave me some websites for those that are curious questioning and Queer oriented. We talked about my son’s transformation into a full time woman and the love of a big black cock. We talked about things like the Esprit conference and the first transgender surgeon who specializes in trans surgeries. So if your closeted or curious about a big black dick in your back door pussy. And anything in between just know that this mommy is very inclusive! And filthy! Let me help you be the sissy or trans female you were meant to be. Even if its just here with me so you can cum! 

Sissy Boy Mommy Wants to Play

sissy boy mommy

Oh, I just love being a sissy boy mommy. When my son was younger, I walked into my bedroom one day and caught him wearing my panties and jerking off. He was embarrassed for some reason, even though I’d been playing sexually with him and his siblings for a long time. I told him he had no reason to be shy and that if he wanted, I would help him get dressed up in more than just panties. He reluctantly agreed and we went into my closet to find some lingerie and a nice dress for him to put on.

After he was all dressed up, he asked me if I would get my strap-on cock and fuck him. I was SO happy because I’d been hoping that one of my sons would be into that! I told him to bend over and I squirted some lube on his pussy and started to slide inside him. I got so excited that I reached down to touch my pussy and came almost instantly. Do you want to hear more about the things I did with my sissy son? Call me and I’ll tell you how I pimped him out to all of my male friends with enormous cocks.

Sissy Maid Training Mommy

Sissy Maid Training

I’m a slutty, slutty mommy who believes in sissy maid training for my sons to be disciplined for me. It makes me so happy when I have the opportunity to transform my sweet sons into little  sissies who cater to their mother’s every whim. My baby boy’s clitty is absolutely darling, and dressing him up in adorable frilly dresses with matching stockings, panties, and training bras is just too much fun! To make me happy, he said he wanted to do anything, so today he is my little maid and I can play with him however I please.

It’s the most adorable little French maid ensemble I’ve ever seen. He looked exquisite in his short skirt and thigh-high white stockings. I had ordered him to draw me a nice warm bubble bath, and since he was such a good boy, I let him wash my huge milky tits as well. Next, he proceeded to take care of Mommy’s hair. It felt really nice to be pampered by my son in his sissy outfit. Now that he did such a good job of taking care of me, I allowed him to enjoy himself after I had finished drying off. Until he came right in his panties, I rubbed his little peter through his sissy slut panties. Now for step two of Sissy boy phone sex with mommy Regina, Finding a cock to train him on, Mommy does have a nice big strap on to help open up that ass.