Tag: sissy maid training

Wet Mommy Pussy Didn’t Save You? Time For Sissy Maid Training!

wet mommy pussy

I Thought Wet Mommy Pussy Would Save You…

It turns out wet mommy pussy wasn’t enough to spare you from the bullying. Who would have thought it would get worse! Today 3 of your bullies came up to the house. I was handling it again, but there you go walking in early again. I was already getting pinned down with a cock in my mouth and one in my ass. At First, I didn’t even see you walk in. I only noticed when they started picking on you. I swear I tried to say something, but he was pushing his cock so far down my throat that all I could do was moan. 

…But It Turns Out I’m a Sissy Boy Mommy!

Your mommy had to watch you get your first round of sissy maid training. The two boys that weren’t inside of me were pushing you around. Then one of them noticed the tiny tent in your pants. One held you down while the other one pulled your pants down. I never knew your cock was so tiny! And neither did they. They decided to show you a real dick. Then they forced you onto your knees and said they were going to make you their whore just like your mommy. They slapped your face with those sweaty teen cocks before forcing it into your mouth.

You fought it at first. But then I watched you start swallowing those dicks. You were slobbering and choking on their cocks. You even had your hand around it stroking. My sissy boy were salivating and your tiny little dicklet was still rock hard. Then when he came in your mouth, I watched you gulp down his entire load. You almost suck cock as good as Mommy. You didn’t even try and fight it when the second bully pulled out an even bigger cock. I could basically see the hearts in your eyes. It turns out I’m a sissy boy mommy. And now you’ve made some new friends!

Sissy mom Ireland loves all her sweet sissy slut babies!

Sissy mom

One of my favorite things to do with my sissy sluts is to make them look pretty. I am the queen of make up and I take great pride in making sure that my sissy’s face is perfectly slutty. I always choose a bright red lipstick for my baby sissy’s dick sucking lips because let’s face it, a sissy’s lips should always be ready and willing to please a real man. And let me tell you, I am going to make sure that my baby becomes a pro at sucking cock and pleasing men in every way possible.

But being a sissy is not just about looking pretty, it’s also about serving and obeying your mommy. That’s why I make sure that my sissy babies are trained to be the perfect maids. You need to know how to clean and tidy up mommy’s holes! You need to know how to please your mommy. I am always filled up with cum and I need my sissy to be able to clean it all out for me. After all, that’s what good sissy maids are for.

I may sound like a strict mommy, but I promise you, I am also a very loving one. I take great care of all my sissy babies and I make sure to give them the best training possible. And let me tell you, your tongue will love it! I will show you exactly how to please and serve your mommy, making sure that you become the perfect sissy slut.

So, if you’re ready to embrace your sissy side and become the best little sissy for your mommy, then don’t hesitate to give me a call for some sissy boy phone sex. I promise to make all your sissy dreams come true and turn you into the sluttiest, most obedient sissy you can be. I can’t wait to meet all my sweet sissy babies and give them the love and training they deserve.

This Sissy Boy Mommy is Ready for Sissy Maid Training

Sissy Boy Mommy Wants to Cage Up Your Clitty

Your sissy boy mommy is ready to play. Is my sweet girl ready to play dress up with Mommy? I know you like to sneak into Mommy’s bedroom when I’m not there, and try on my sexy panties. We can’t have that can we? I thought it would be better if I got you a couple pairs of your own. And maybe a couple of cute dresses for you to wear around the house when no one’s home. But in exchange for the pretty pink clothes, you have to lock up that clitty for me. Ok, my pretty sissy whore?

sissy boy mommy

Cock Sucking Mom Milks You for Sissy maid Training


When you’re dressed up as my little girl, you won’t have a use for that useless sissy cock. So I’ll put it in a cute pink cage and lock it away for you. Your panties will look so much cuter without that oversized clitty pushing through the top of them or stretching out the front. Mommy knows it’s a big change. So I’m going to make it a little easier by being the cock sucking mommy you know and love. Pretty girlies deserve to have their clits licked and you are one of my prettiest girls. Let mommy make you feel good before I turn you into my princess.


You lay there and relax while I tease your clit and sissy pussy with my tongue. You sound so cute and girly when you moan. And this sissy fuckhole is all lubed up and ready to use. Mommy’s going to push one of her special toys in that sissy ass for you. I’m going to fuck you like that cute sissy slut that you are. I want to see my pretty baby go cummies all over yourself. Come on baby. Don’t you want to taste your own cum? Be a good girl for Mommy.

Sissy boy mommy Tina enjoys turning stray boys into sissies

Sissy boy mommy I am a Sissy boy mommy! My boy loves being pegged… He gets so excited when I bring horny men home with Big black cocks to share with him. I found out about his sissy ways one day after catching him prancing the house in my used panties. He wanted his fresh little clit to smell just like momma’s pussy. That’s when we dug deeper into exploring his sexuality! I introduced him to my sex dungeon and all of my toys… He confessed to fondling his asshole using his fingers… But I told him I had something much bigger and better than that. I slipped into my self-thrusting strap-on dildo and had him gag and drool all over my sex toy.

This was only the beginning of Sissy maid training, he was soon dressed in lace daily and left to do all the womanly duties around the house.

This was how he earned his next serving of creamy cum! His behavior depended on his serving, whenever he was a naughty sissy slut. I tease him with my drooling cum filled cunt; while telling him how good it felt to have my pussy stretched. He is to then get down on his knees and I instruct him to give momma a cum clean up. When he is on his best behavior I always make sure to bring home a nice meaty big black cock. His feminized moans always let me know how thankful he is to be able to serve his newest daddy. Being a Sissy mom is the best thing that has ever happened to me!

Lenora catches her sissy slut son.

Sissy boy mommy

Lenora Catches Her Son 

Lenora had been a single mom for as long as she could remember. Raising her son, James, had never been an easy task. So, when she stumbled into the living room one night and saw James doing something she’d never expected, she could hardly believe it. There in the half-light of the living room was her son, locked in a passionate embrace with another boy, their mouths closed around each other. She was a Sissy boy mom. 

Mommy Lenora stood there quietly, letting the moment unfold, until she decided that it was time to talk. She walked over and knelt down in front of them, and explained that it was okay, that she had been there once too. James looked sheepish and admitted that he had been exploring his sexuality, that he had just been curious, and it wasn’t anything serious.

But Lenora wasn’t one to leave things at that, she wasn’t content with leaving her son’s sexuality unchecked. So, she began to explain the basics of proper cuck sucking: the pleasures of using one’s hands and tongue. She was determined to make sure that her son could experience the fullest pleasure from his activities.

For the rest of the night, she instructed James as he sucked and fucked his little friend. She helped them apply lube and showed them how to explore each other’s bodies. They both knew that despite their awkward beginning it was the right thing to do.

Mommy Lenora Transforms you into a Sissy Maid!

Sissy maid training

Mommy Lenora Punishes You

You are fucking pathetic. What kind of son are you? You act much more like a whiny little bitch than the boy you are. Mommy has the perfect punishment for you though Sissy maid training. You want to act like a girl. I am going to treat you like one. 

Put on that little French maid uniform, and a pair of heels. Yes, that is right there are no panties with the uniform. Do not worry your little asshole will not be exposed. I have a pink plug to fill it with. Good little sissy boy slid that right in there for me. Tell me how does that feel? Good and heavy in that sissy pussy of yours huh? Now time to get down on those hands and knees and scrub the floor. I want to see that pink little plug twerk as you clean Mommy’s floor. If you miss a spot, I will make you lick it clean. 

Sissy Maid Training is a prerogative of mine.

Sissy Maid Training is a prerogative of mine.  You need to learn how to be a good sissy for your Mommy and man. Sissy maids are awesome! You are a sissy boy and I have been training you to become a good sissy boy. You have progressed as you know how to dress and how to get a man to fuck you in your sissy boy pussy.

You now get to train on how to be a good sissy maid. That is right. You need to see to your man and Mommy’s needs around the house too. You need the right little maid costume, short. Want to see that little sissy pussy of yours when you bend over to do the dusting, scrubbing the floors, that pussy should be readily assessable.

Your man comes home and seeing you cleaning. Little maid outfit looking so cute. Lifting the skirt up just a little, you feel cock rubbing along your pussy. Don’t stop cleaning as he presses deeper into you. That’s it. Take all of him into you. He buries himself in you. Pounding you, tighten that pussy around that cock. Beg him to fill your pussy up. You want and need him to fill you up. Just like that. Cum with him.

Sissy maid training

Lenora Catches Her Son In Drag

Sissy boy phone sex

Lenora Catches Her Son In Drag 

I had spent the weekend away from the house and decided to surprise the kids to see what they were up to. When I showed up however I was the surprised one. My house was completely silent and for a while I figured no one was home. Heading to my bedroom I opened the door to find myself right in the middle of a Sissy by phone sex fantasy. 

There was my son dressed up in my pink lace teddy, matching lace thong and a pair of my thigh high stockings. He even had the boobs stuffed. What the fuck!!!!! I started to yell what are you doing right now are you fucking kidding me. He turned around, but that just made it so much worse. He had my fucking 9 inch pink dildo shoved deep into his little boy pussy. How dare he violate my shit. Boy do I have a plan for him. 

Sissy boy mommy Christina transformed another sissy

Sissy boy mommyI love being a Sissy boy mommy; being able to train young men and teach them how to be perfect dolls! A Drag Queen that struts like Beyonce with lips like Angelina Jolie. I love watching sexy feminine boys perform live at drag shows in custom fits that they made at home. Its such an adventure to see these things; such creative minds like theirs can create. Especially, because momma manages to make a few friends.. A sexy milf and a young tranny whore tag team is everything an older man dreams of..

He gets the best of all worlds. A Sissy mom trains their sluts to be prim and proper! Nylons, garters and any sorts of pantyhose is a must.. its how you create a mysterious look that gets men wondering.. The more attention you have of theirs, the more fun we will have.. Draining those deprived cocks of the unforgettable sex they have never experienced; until today. A nice facial contour and 24hr outlast lipstick, we don’t want your lips to smudge when you are deepthroating.. Lets make sure you look like a Total: Hot slut. At all times! I am a sexy Mom with big tits and curvaceous well kept body; the definition of a MILF. I will teach you all my tricks, Sissy boy.

Lenora Scores a New Slutty Sissy Maid!

Sissy maid training

Lenora Needs Her House Cleaned

Who says that cleaning and household chores are a woman’s job. This is the main reason that I love having a great little slave. My house needs to be cleaned and I know just what to do! A Sissy maid training session.

Come right in and strip down from those man clothes you are not a man. Throw on this little french maids outfit for me. Obviously, this is not your full uniform what would be the fun in that little sissy. I grab a butt plug tail with a feather duster for the tail. Bend over bitch while I slide this inside of you. 

Perfect now, we are going to start with some dusting, Clench that fucking duster tight so it does not fall out. Bend those fucking knees and dust the tables. Feel that toy as it rocks back and forth in that tight little fuck hole of yours.