Category: Sissy maid training

Sissy Boy Phone Sex With Mommy Hunter Makes Those Small Dicks Cream

Sissy boy phone sex Oh, I absolutely adore sissy boy phone sex and  dressing up my sissy boys! It’s the best part of my day, watching them transform into these pathetic little sluts who can’t even please a woman with their tiny, worthless cocks. I have this one sissy who’s especially good at it; he’s always begging me to put him in my panties and let him wear my clothes. He knows how much it turns me on to see him all dressed up in my lingerie, high heels, and makeup. It’s like having my own personal plaything!

And when it comes to sucking cock, well, let’s just say he’s not very good at it. He tries so hard but he’s just not man enough for the job. That’s why I keep a big dildo in my purse for him to practice on. I love watching him struggle with that huge thing in his mouth while I laugh at him. It’s hilarious! And when my black friends come over, they love helping me fuck my sissy boys in the ass. They know how much I enjoy sharing them and how much they deserve to be used like the little sluts they are.

I’m not ashamed to admit that I’m a gold digger either. I love having men cater to my every whim and desire. If they can’t handle being my sissy, then they’re not worth my time. But if they’re willing to submit to me and do everything I say, well, then they might just have a chance. And don’t worry, I’ll make sure they get plenty of chances to please me. I’m a total sex addict, so I need my fix on a regular basis. And when it comes to my sissy boys, they’re always ready and willing to give it to me. They know their place and they love it.

So if you want to be my sissy, you better start practicing your makeup skills and learning how to walk in heels. And don’t even think about complaining about how uncomfortable it is; you’re just going to have to deal with it. Because at the end of the day, you’re nothing but a worthless cock who exists for my pleasure. And if you don’t like it, well, there are plenty of other sissy boys who would love the chance to serve me.

Mommy Dearest: A Taboo Phone Sex Session

Cock sucking mommy

Oh, my little baby—you have no idea what’s in store for you. Your cock sucking mommy has a naughty, little secret, and it involves that delicious-looking cock of yours.

Remember that fateful moment when I sneaked up behind you, pulling your shorts down to reveal your sturdy member? I couldn’t help myself—sucking dick has always been my greatest vice. And your cock, dear baby, was made for my mouth.

I savored the taste of your precum, licking it like a delicious treat. The way you moaned sent shivers down my spine, and I knew I had to have more. More of that glorious meat Exploring down my throat, making me gag on its magnificence.As I stood before you, stripping teasingly slow, you couldn’t help but notice the lust in mommy’s eyes. My black bra revealed my perky nipples, begging to be sucked. But I wanted to play a bit longer.I stroked your craving cock, watching it pulse in my hand. The veins running along its length begged to be worshiped, and worship it I did. Sucking, stroking, taking you deeper with each pass.The lustful look in your eyes only made me hornier, and I craved the taste of your manly essence. I needed to feel you inside me, but first—a little foreplay. Or as mommy likes to call it, cock worship.

Sissy mom Ireland set up a fun playtime for her baby

Sissy momSissy mom Ireland set up a fun playtime for her baby! I know how hard it is for you to make friends, so I decided to throw you the best party ever, filled with all the sissy mommies and their diaper sluts.

First things first, let’s talk about the treats that I have in store for you. These aren’t your typical party snacks, but you know poppers are just way too much fun to pass up. I want you really high and  to get down on your knees and suck on the BBC’s I brought you, like the good little whore you are.

I expect nothing but the best performance from you, or else you’ll face some severe consequences. Just imagine sitting in your own mess for hours on end, wearing nothing but the ugliest diapers I can find. Do you want that, my sweet little sissy? I didn’t think so.

Now, let’s move on to the main event of the night. I’m talking about the big, black cocks that I’ll be providing for you to pleasure. Mommy wants you to serve these men like the Phone sex whore you are, and I expect you to take every inch of them sliding over your diaper and thrusting deep into you. 

But don’t worry, my little sissy, I’ll make sure you’re filled with cummies by the end of the night. And who knows, maybe you’ll even make some new friends along the way. Now, I know you’re probably excited and a little bit nervous, but that’s perfectly normal. Just remember to follow Mommy’s rules, and you’ll have the time of your life. And if you’re a good little sissy, I just might give you some extra special treatment. 

 

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