Category: Sissy maid training

Sissy boy mommy has to give her baby lotsa spankings

Your Sissy boy mommy is very disappointed in you slut. It’s time for some tough love and a good old-fashioned spanking. You arrived at my doorstep, I was disappointed to see you dressed in nothing but a pair of slutty panties. Where was the pink frilly school girl dress I had picked out for you? Sissy boy mommy

I immediately took charge, making you go to my room to put on the proper attire. I want my sissy boys to look as pretty as possible. Once dressed to my satisfaction, you are bent over my knee for a good spanking. Gosh, I love it the way I make you squeal and beg. I was really getting into it, raining down hard smacks on your bare bottom until it was bright red and stinging.

But the spanking was just the beginning. As a good Sissy mom, I needed to see how sorry you were for your lack of effort. So, you followed my orders to get on your knees and pleasure me. I lay back on the couch, spread my legs wide, and you went to town. You really put in the effort of making Mommy happy. Eagerly licking my pussy like a good little slut.

But I wasn’t the only one who needed attention. I called over Daddy, who was more than happy to join in on the fun. He pulled out his massive twelve-inch cock and my sissy boy eagerly wrapped his lips around it, didn’t you? Sucking and slurping so good you could be a pro. I could tell you were desperate to cum, but I wasn’t going to let you off that easily. I made you wait, teasing you and denying you until I was good and ready.

Finally, after what felt like an eternity, I gave my sissy boy permission to cum. You let out such a loud moan as when exploded. Daddy followed suit, unloading his own massive load deep in your tight slut hole.

But the lesson wasn’t over yet. I made my sissy boy clean up every last drop of cum, licking and sucking until there was nothing left. Only then were you allowed to stand up and catch your breath. But I could tell you need to learn more. You know you do slut, so call for Sissy boy phone sex.

 

MILF Sissy Trainer

I have a sissy boy I have been training and she has grown to be quite the little good slut.  She calls me every single night and we work on her training.  I insist that she dress up for me very sexy and trashy. She has to email me a picture to make sure her outfit is acceptable to me. I love red lipstick on a sissy and blue eyeshadow. She is such a good girl and always does what I tell her. I also have her stretch her little sissy ass pussy for me with dildos of all sizes. I love it when a sissy is willing to take cock for me. I love getting BBC for them. I dress my little sissy up and take her to a bar to pick up some nice cock. I take the guys home and they run a train on my little sissy. I love watching her get fucked, used, and abused. It is so mother fuking hot to see every hole of hers filled to the max.  I have one guy fucking her little ass pussy while another guy has his cock in her mouth.

milf phone chat

She is getting spit roasted and I sit there and watch. Most times I can’t help it. I have to play with my pussy. It just turns me the fuck on so much. Now on nights when my sissy is lucky I will let her get a taste of my pussy.  I make her lick my pussy until I come then she has to swallow every drop. My sissy is under my total control. I also punish my sissy harshly when she fucks up. It normally involves icy hot for her ass and a nice big paddle. My sissy is careful to be a fucking good one. She knows what will happen if she defies me.

 

Wet mommy pussy will take complete control of her Sissy boy

Wet mommy pussy

It’s your favorite sissy mommy mistress and my Wet mommy pussy will take complete control of you my little Sissy boy! The moment you hear my sexy voice, you know you’re in for a wild ride, and I’m more than ready to take you on the journey of a lifetime.

As a foul-mouthed, unapologetic dominatrix, I pride myself on being in control, especially when it comes to my sissy boys. These submissive little sluts crave my attention, my approval, and most importantly, fucking that tight sissy pussy. You will embrace the fact that you are nothing but a whore for Mommy. 

 I peruse through the desperate pleas for my attention from my adoring sissy fanbase. Their messages, filled with lewd requests and promises of servitude, fuel my insatiable desire to dominate and control. The biggest whore wins. I want to put you to work. You are going to hussle your slutty ass and make Mommy money. 

I know you are willing to serve your Mommy, I mean why else did you call me, right? You know you need me to show you how to open up your legs and serve as a cum whore. Oh, look at your clit just ooze with desperation. You will never deny your Mommy, and you will take every cock raw. 

I take great pride in molding my sissy boys into perfect, submissive pets, ready to please and serve at a moment’s notice. Thus, as the Sissy mom, I make sure to provide them with the proper training they so desperately need. The training You so desperately need!

You will learn whore, Whether it’s teaching you how to properly apply makeup, helping you pick out the perfect pair of panties, or simply offering advice on how to navigate their newfound femininity, I am here for my sissy boys every step of the way.

Mommy is going to stretch out your bussy wider than you can imagine. You will be on your hands and knees while Mommy’s huge cock rams into your hungry hole. I love it when I make you squeal while I am deep inside you.

Listen, sissy whore, I see you. I know you spend most of your days pretending to be a “Man”, but come on we both know that’s a lie. You don’t fit in because you haven’t let that hole play enough. Mommy will get you the connections you need to make me proud. Just imagine all the cock you are going to take for your Mommy.

If you’re feeling lost, confused, or simply curious about your own femininity, don’t hesitate to reach out. Mommy Ireland is always here, ready to take your call and lead you down a path of passion, power, and utter debauchery. Call so Mommy can train you with Sissy boy phone sex!

 

Mommy’s Little Perverted Phone Sex Toy

Hey there, my little man. Mommy’s here and ready to show you how a real woman can make you feel. You’re so lucky to have me guide you through this. stroke that cock like a good boy while Mommy tells you what to do.

Your eyes might deceive you, but my mommy senses tell me you’re about to hit puberty, and I’m here to welcome you to manhood. Picture Mommy’s soft, full breasts pressing against your face as you stroke your big boy cock. Can you feel it? Good.

Now, imagine that same cock sandwiched between them, sliding against my cleavage as I provide you a glimpse of what the real world has to offer. You’re so young, yet so eager to please. I love that about you.

Mommy’s pussy is dripping wet, and that tight little asshole of mine is begging for your attention. Pound me in either one; I’m your filthy MILF whore. I love the way you think about your momma when you touch yourself. It’s so taboo and naughty, but hey, I won’t judge. In fact, I encourage it. Share your most secret, dark fantasies with Mommy.

I’m here for you, sweetie. To teach you, to show you, and fulfill your every desire. So, keep stroking, let Mommy do the work, and together, we’ll reach the promised land.

And remember, I’m your phone sex momma, always ready to cater to your every MILF fantasy.

Sissy training phone sex mom Valentine trains by affection.

            Sissy training phone sex mom Valentine trains by affection. Now you know that sooner or later I am going to be playing with my sissy son. If for no other reason than to make sure that you have learned all there is to learn from me. Going to whip you into shape. Stretch that pussy out. Give you all you got and then make you go a little further. At the same time going to be giving so much attention.

            To begin with I will come home and find you in my bathroom. All dressed in my lace panties and bra. Well now if I had known that you wanted to be a girl I would have chosen a much more suitable name for you such as Brandy. It is a fine vintage to be sure. Next going to show you how to apply the makeup. The first thing to remember when applying makeup is the coverup goes on first. Then you do the eyeliner. Now this can be any color, but a lot of people use a brown or a black. Give it an exotic look across seas with the tilt of the eyeliner. A little gold glitter and you look sexy.

            With attention to detail, you are going to need to wear clothing that fits you. Going to go to your sisters’ room where she is closer to your size and pick out some pink panties and bra for you.

          Sissy mom likes to play and teach her sissy son for his training. Sissy training phone sex

            Going to show you how to wear the garter belt. As can be seen I like to teach you and your training is really coming along. You need to stop interrupting me all the time and actually listen to mom or the affection is going to be less, and the whip is going to be harder. Pay attention when mom is speaking.

            As soon as we have you in the right bra and panties that are pink lace then I am going to put on my strap on at least as soon as I have stripped down to my bra and panties. Then you are going to be taught how a sissy bitch whore sucks on my dick. Afterall, you do want to please me now don’t you. That is what I thought. Once you have sucked on my cock and listened to the directions, I give you then we will take a break and you can clean my house while you are still dressed up as a little sissy bitch whore.

Sissy mom will punish and abuse just to soothe you.

            Sissy mom will punish and abuse just to sooth you. In fact, going to start with getting you all dressed up. Make up and all. You sit over there. Mom is going to break out her make-up. Not the good stuff. At least not yet. As soon as I know you can be a good sissy for your mom then we will discuss getting you your own stuff. Like blush, should be with the color of your skin. The first thing to realize is that as a mommy boy you will be subjectable to my whims. Pleasing me first and foremost.

            Next thing you know you’ll be Sissy boy mommy little bitch in your maid’s costume. Dusting the house. Wiping it all down. At the same time Mommy is going to be watching, filming, and even ordering you to show your little pussy ass. Quickly teaching you how to kiss, how to French kiss the pussy.  Going to have to find you a daddy or just a mommy strap on and introduce you to the ways fucking. Needs to enjoy the dick.

            Holding the dick in my hand. Squeeze you from the base on up. Suck on my tits. All for mommy for otherwise you need to be punished. Paddle the butt. Just to fuck the pussy. Beauty knows no pain no boundaries. To be the best you need to embrace the pain. Be good for mommy for after the punishment and abuse, to be sure going to soothe you. Making you cum with a combination of them all. Just wait and see. I will turn you into a Sissy who cums to pain.  Sissy mom

Sissy maid training dust that sculpture, fluff the skirt.

            Sissy maid training dust that sculpture, fluff the skirt. Do exactly as you have been trained to do. Make me proud. Now I showed you how to dust a sculpture. After all you need to dust it before you clean. Make sure that it is all clean. Show me what you have learned. As soon as you have washed the sculpture remember to fluff the skirt.

            In fact, fluff it up. Show a little skin. Run a hand down the stockings. In the long run you need to forget the panties. May like them but when you are fluffing the skirt you will be exposing your pussy. You need to expose the pussy.

            All in all, you need your training in capturing not one but numerous different men. Those sculpted bodies. Lick the length of them. From the tips of their toes, up to those cocks, rock solid asses, all the way up to the top of their head.

            All of sudden it will all fall into place and before you know it, those men will be lining up around the block to see you clean their sculptures and fluff your skirt. Going to open you up. Make the finally cum and you in the end will cum out of your pussy too.

            Make your Sissy mom proud.Sissy maid training

Sissy boy mommy will do your make up.

  Sissy boy mommy          Sissy boy mommy will do your make up. Make you look like a beautiful little sissy and no one will ever be the wise. After all you mommy knows what is best for you. First we will pin all your hair back. Now the reason for this is so that you don’t smudge and smear the make-up when we do the hair. A point often overlooked is a wig should have the hair pinned back or a net cap put on.

            Giving you charcoal eyes. This is thick eyeliner around the entire eye. Smudge it ever so little. As can be seen it draws attention to how high your cheek bones are, how wide your eyes. Next is the lipstick. Ruby reds, magenta, bright colors will draw attention to the full mouth.

            Smack your lips together and say ahh. Another key point when you are out to eat be sure to get dick shaped objects to slowly put into your mouth. Be a good sissy boy and eat it slowly. Dab your lips. Hence keeping the lipstick.

            Most notably in your handbag you need to carry some lipstick (same shade), some extra eyes shadow, and of course the lip liner. Wherever you go these are essentials. Now before I let you go out. Your Mommy wants to have Sissy boy phone sex and peg you after you suck on my strap.

            All in all, I want to make sure that you are ready to go out on your date. Make me proud.

Sissy boy mommy Ireland will make your little clitty bust!

Sissy boy mommySissy boy mommy Ireland will make your little clitty bust! I’ve been around the block a few times and I know a thing or two about how to satisfy your insatiable hunger for cock and cum. I’ll make you moan and beg for more, my sweet boy.

I know what you really want, deep down inside. You want to be sissified, don’t you? You want to be my pretty little princess, all dolled up in frilly dresses and high heels, with your tight little bussy just begging to be abused. I am more than happy to make that fantasy a reality for you.

I’ll take you under my wing and teach you everything you need to know to be a good little whore. I’ll show you how to suck a cock like a pro, how to take it deep in that sweet little throat of yours until you’re gagging and crying for Mommy’s approval. And when it’s time for that bussy to be filled, I’ll make sure your hole is stretched out to take thick hard cock. 

I have a lot of friends who would love to play with that hole. You will make Mommy a lot of money by whoring out your slutty holes. I’ll make you crave cock and cum, and beg for it like a good little slut. And get ready baby because you are going to take cock after cock, because let’s face it, Mommy has bills to pay, don’t I?

So what are you waiting for, my little bitches? Pick up that phone and call me for some hot Sissy maid training. Mommy will make your tongue numb by the loads of cum you will clean out of my juicy pussy and ass. I will mold you into the sluttiest, most obedient whore you can be. And trust me, once we’re done, you’ll be begging for more. So come on, my sissy darlings, let’s get down and dirty together.

 

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!