Category: Sissy mom

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. 

Mommy and Sissy Son Suck off Client and Become Paid Whores

Mommy sucking dickYou’ve just walked in on your Mommy giving her client a blowjob. You do know Mommy loves being a whore, right? I know that I can do other jobs but I’d rather pay our bills by getting on my knees and sucking as many cocks as possible. How do you think that Mommy is such an expert at making your cock feel good? I have had lots of practice. My client says that he’ll pay extra if you come over here and pleasure his cock as well. You want to be a good slut for Mommy, don’t you? I’ve been on your computer and watched all the sissy porn you like. Wonderful! Come over here and lick that cock up and down. then, take it all in your mouth. You are a natural cock sucker. Why don’t I push that cock between my tits while you suck on the head. He can tittyfuck me while he’s shoving his cock deeper into your throat.

Sissy training phone sex Mommy loves chastity

Sissy training phone sex

Sissy training phone sex Mommy loves chastity.

 There is nothing like keeping my own boy locked up 24/7. 

 I want you thinking about your own mother controlling and denying your right to orgasm. 

It brings me unthinkable happiness to tease my son’s dick with my feet. I love being a Domme mommy to a pathetic and useless boy. I get my pleasures from fucking big dick to men on a rotating basis. I make my son watch as he is so tightly bound he just might cry. And of course, why would I care if he cried? I like rubbing in his face all the men who get to fuck this wet cunt of his mother’s.

I want him to cry in begging for Mommy to release him! Torturing him with my beautiful feet just inches from Mommy’s pussy. Oh, now how my little boy the thrust up and down, humping the air. I laugh and tell him that he isn’t cumming anytime soon! 

Sissy training phone sex Mommy loves chastity.

Let Mommy Regina take control of your Sissy clitty during hot Mommy son phone sex. Mommy will always have your best interest in mind actually gets her own cut off over big fat fucking dick!

Sissy Boy Mommy Has Some Explaining to Do

Sissy Boy Mommy life is pretty much just like having a girl.  We love going to Victoria’s Secret and trying on sissy boy mommypanties together. I use to be upset that all my panties were always missing.  That is until I walked in my room on day and discovered that my little man had gone through all mommy’s dirty undies and was inhaling them. Like a drug going up his nose only it was just the aroma of my dirty, smelly, sex ridden, cum filled panties that my son was inhaling for the smell alone.  My heart was so filled after that day.  I knew what I had to do.

What is that you ask? I had to put him through sissy training.  I wasn’t really sure how to not go all in with it since I do so much different things through my work here on the phones.  So we went on a shopping spree, bought some pretty little dresses to dress him all in.  Pink and purple with some white pretty lace.  Knee high stockings for his little boy legs.  Mary Jane shiny black shoes with a small heel to prance around and twirl around in.   I make him do his makeup to look his absolute best.

Then he has his practice time where he takes orders from mommy.  Being the pathetic cocksucking bitch that he is, he isn’t treated like a girl here because here is where things get dirty, he’s a sissy bitch with a little boy pussy cunt that will get used and abused from this point on.  He’s learned on my dildo’s about sucking cock and I have some of my biggest black cocked friends on the schedule to come by to get their cocks sucked in a few days.  They think it’s by me but I can’t wait until they

From Sissy Slut To Breeding Phone Sex Slut In Minutes!

Breeding phone sex

Why don’t you sit right there and be a good breeding whore for Mommy. All dressed up in your pretty pink ruffles, just waiting to be praised and played with like the good little slut you try so hard to be. Such a good little slut, your make up done just like I’ve instructed, sitting there on your knees. Just wondering what the day has in store for you.

Such a good little sissy ready to do as I wish. Your little clit making you whimper like a dirty little slut with each spoken word. My favorite little slut to tease and torment, to turn into the cutest sweetest little hole for all the big massive cocks to fill.

Turned into a little breeding whore by yours truly.

Your hole continuously filled with that white creamy goodness. Making you whimper and beg for more like the dirty little bitch you can’t help but being.

Come be bred with me, show me what a good little slut you are.

Live phone chat with Big Mama Queenie

Big mama Queenie has seen, heard, and done things you never knew existed, Queenie explored fetishes and hardcore kinks that would make priest in confession blush.

Live phone chat

Live phone chat with big mama Queenie, hear her erotic tales and stories of a Phone sex whore. Queenie enjoys talking to you when you call her, she masturbates hearing your nasty stories of sluts you banged. Tell her all the kinky things you want to do, nothing is too taboo to talk about. Queenie is a pro at sexy talk on Adult phone lines. Big mama Queenie is always a good time fuck and she loves to get you off in your pants. Cream really hard for her so she has another erotic story to tell.

Sissy Learns to Ride Cock from Mommy

Sissy boy mommy Tiana

Mommy loves playing with her little sissy and teaching her how to ride cock. I love getting many men and teaching her how to ride cocks from 6 inches upwards. She has been playing with her tight little fuckhole, inserting a buttplug of various sizes to stretch her out. Now, she can take a cock that is thick. The only thing she needs to learn how to do is take a big, long cock. That little cock slut is a natural. She is able to take every inch of those cocks. Mommy has taught her little sissy well. Well then, there is no reason why only she can have these cocks. Mommy is so horny and all of these men are so hard. I want them to use me just like they’re using my sissy son. I beg them to fill me up with their cum, and they pound my fuckhole just like they fuck my son. This is wonderful mother-daughter bonding.

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.

My Wet mommy pussy gets so sloppy when I am aroused

Wet mommy pussyMy boy loves to Jack Off With Mommy especially when I guide him through masturbation. I drag his hand up and down his cock for him while my tits rest on his thighs.. He is such a good boy his hormones have just been running haywire and he doesn’t know how to approach the pretty girls at school.. Lucky for him  he has got himself a mom with plenty of experience. I take great care of my young ones. I love when his balls swell up against my chin while I have his dick balls deep down my throat.. I suck him off so good his toes curl. My Wet mommy pussy gets so sloppy when I am aroused which is where his older brother comes in..

He fucks me doggystyle and teaches my youngest how to fuck.. When he is old enough I am going to have him bend me over and fuck me just like his older brother.. They are only 3 years apart so it won’t be long before I am getting gangbanged by the two of them.. I masturbate all the time to the fantasy of having their dicks rubbing up against each other stretching my cunt out. My oldest boy has gotten one of his friends to tag team mommies ass but there is still nothing like having two brothers fuck me passionately. all the love we share will make the experience so sensational.. My oldest has bent his brother over and fuck him up the ass but no way will I be a Sissy mom he is going to learn to love pussy just as much as he loves ass play.