Category: Sissy training phone sex

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.

 

Sissy boy mommy transforms her little son into a princess of cock! 

Sissy boy mommySissy boy mommy is here to make you into a pretty cum loving princess. As I get older, the more I need to turn fem boys into little sluts that can strut. My own love for expensive clothes, heels and lingerie including hose translates into princess cross-dressing. And that’s just the start of what I do to my little boys, who have a need to be sexed up sissy girls. As a mother, I have very good nurturing skills. When my youngest came to me meekly asking if he was ever going to look like the big, beefed up men in a nudie magazine, I held back laughter. 

Sissy boy mommy transforms her little son into a princess of cock! 

“M.m. Mommy, I want to look like him, he’s got lots of muscles and a b. B. b.big  Cock!”  He stutters. My sweet boy with the beautiful long blonde curls and thin body just wants to be a big man. I let him down slowly. “Honey, I think you might look better like one of these girls.” I mewed as I showed him a collection of pretty sissy girls. I then pinched his little boy clitty and asked him if he thought , “would this get any bigger naturally?” My boy lowered his head and looked back up real fast! I c, could, could, look like you mommy?”  

“Well? Do you think you can handle that big mans cock one day, at least in your mouth?” he blushed and said test what he was really looking at in my Vintage nudie magazine, was cock! Well, baby boy we have a lot of training to do, but by the end of the day, I will be on my way to being your sissy mom!” I cooed. 

And I can do the same for you my sweet boy reading this! 

Sissy boy mommy gives you the hole you need

You looked for a Sissy boy mommy because you have been needing a sissy boycunt for you to fuck. After you paid your fee and was over you wanted to watch mommy feed her big guy her mommy tits. “Come suckle on mom” I said as I pulled my big mom jugs out. Once he was suscking on my nipples you got up close and pulled your cock out. I watch as you stroke your dick to my son sucking on my boobs. Your cock is stiff, and you push it right up to my lips.

“Suck my cock and show your boy how to use your mouth” you demand. I got paid already so I was fine sucking your cock. It was sloppy and wet. Some of my spit and your precum dripped on my son’s face. Now you suck on my cock like your mommy showed you” is what came out your mouth as you grabbed his head. Then you pushed his face on your cock. “Open up son and suck him like you did mommies nipples” I instructed as your big cock pushed inside my son’s mouth. After a while of you moaning as my son sucked your dick, you were ready to fuck him.

Sissy boy mommy

It is my job to make my son into the perfect sissy fuck toy for you. That is why I had him bend over and I helped him spread his pussy for you. “Fuck my sissy son” i say as I direct your pdick towards his boypussy. Once your cock felt his hole, you couldn’t help but push deep inside his ass. Your hard cock rammed him as you grunted like a wild animal. “Milk me sissy bitch” you moan and grunt. Finally, I saw your balls tighten up and you started spraying all your cum inside my son. After you gave him every drop, you thank me for providing the sissy hole you needed to milk your cock.

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!

 

Anal sex mommy Regina always keeps it mixed up!

Anal sex mommyI’ll say it until my dying breath, being an anal sex mommy is what I was born to do. It’s time to have a big milky momma give you her shit hole to control. Are you up to the ass fucking challenge! My husband and sons recently dared me to an ass fuck fest, and who am I to resist?

Your hot mommy eagerly accepted the dare, knowing full well that this was what I have been trained for! Mommy Reggie is, after all, the infamous “Big Milky Momma,” and this will be my ultimate ass-capades! The room was filled with anticipation as I dropped my clothes and my hips wiggled with pleasure!

The asshole to be conquered, a timid young man, entered the room, his eyes wide with a mixture of fear and arousal. He could hardly believe that he was going to finally experience the full power and intensity of Big Milky Momma’s unholy lovemaking.

Anal sex mommy always keeps it mixed up!

“Do you accept the challenge, boy?” this sexy woman growled at him, my voice a low, seductive purr. The young man gulped, “Oh, did you think it would be my ass you’re fucking? I have other news for you!” Many men have come in this ass, and they are welcomed to jizz up my butt with that good nutt! But First, an ass virgin is what I REQUIRE! Jack Off With Mommy and fuck my ass or bring me a nice tight ass for my fingers and big momma strap. I’ll have you flat on your back bouncing my leaking mommy milkers all over your cock and balls!

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.

Let Meredith be your Phone sex mommy

Phone sex mommy

I love being a phone sex mommy. Mommy is here and ready to take full advantage of her little sissy boy. She’s going to dress you up like a good little boy, in high heels, a thong, and matching bralette. Do your make up, and make you look super sexy! Once you’re all dolled up, Mommy is going to do a little photo shoot with you. Do lots of poses in various positions, ass up, showing you bussy to the camera.

I want you to tease the camera, do what Mommy tells you to do like a good little sissy slut. 

Now Mommy is going to put the camera right up here on the table. Now we’re going to put you on live stream. Let all the other sissy boys out there see what a good boy you are for me. Dance and prance around in your sexy lingerie. I want you to feel nice and sexy letting everyone on the live stream see you all dolled up.

It’s okay, no one will recognize you, we did your make up so good you don’t even look like yourself anymore. Specially with that nice red curly wig that Mommy put on you, you look so cute in it!

Now I want you to sit on the bed in front of the camera, and bend over, grab some lube, and I want you to lube up your sweet little busy for Mommy. I want to show everyone on the live stream just how far open we can stretch your tight little bussy. Get it all nice and lubed up for Mommy’s big black strap on, this huge 10″ dildo will fit nicely right into your lubed up bussy.

Fuck yes you good little sissy boy, it’s sliding in nice and deep, take it all. Mommy is going to pull this out of your little bussy. I want you to get on your knees in front of mommy and the camera. Good boy, now I want you to lick your sweet bussy juices off mommy’s big strap on dildo. deepthroat it like a good boy, do what mommy says. 

I enjoy sissy training phone sex too. Now pick up your phone and call Mommy Meredith and tell her all the nasty little things you want her to do to you. Be a good boy, call me now. 

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

Horny milf pictures with your breeding whore

Horny milf pictures

I just caught you snooping through my drawers, looking at my dirty horny milf pictures! You are my sons’ friend, so you shouldn’t even be in my room. I think it’s time you be punished. You have been having all kinds of milf fantasy stories, haven’t you? I’m trying to come up with the perfect punishment to fit the crime and I think I found it!

                What I think will torture you the most is a “you can look but not touch” scenario. I tell you to sit in the chair in my bedroom. I get on my bed, strip down and lean against the pillows. I stick one of my legs up in the air behind my head, so you are staring at nothing except my pink mommy pussy. It looks back at you and you are hypnotized by the view.

                I lick a couple fingers to get them nice and wet, so they’ll be able to slide right into my pussy. I fuck my pussy while I rub my clit with another finger. I feel an orgasm sneaking up, but that just makes me go faster. I want my body to explode. I look over at you and see you stroking your cock so fast and hard as well. That’s when I ask if you want to jack off with mommy?