Category: Sissy training phone sex

My Son, The Sissy

Sissy mom

 

I’m proud as fuck to be a sissy mom and of my ever blossoming soft little son.  She’s full of surprises, constantly kink hopping to help himself figure out exactly who she is sexually.  I think it’s a smart move for any pan sexual.  How do you know what you do and don’t like until you try it?  I think she’s really found his thing, though.  He’s fully embodied her silly little sissy side.

She absolutely has to get my opinion on all of his prissy outfits.  From frilly pink dresses and maid uniforms to leather corsets and fishnets, she loves to try on his wussy wear for me to see what I think.  She’s great at it, too.  My mama’s boy should get paid to model his effeminate ensembles, she makes them fucking work with legs that don’t quit and an ass I would kill for!  

Of course, being a true sissy boy mommy, I have to show her the ropes and teach her what being a girly guy is truly about.  It isn’t all fun and games for my pretty little pantywaist, she gets the same training as everyone else.  There’s no cutting corners, she has to follow all of the rules and listen to everything I say.  But, just like the others, when she’s been a good girl I’m sure to please her little clitty and let it dribble anywhere she wants.

 

These Tits Were Made For Sucking

Jack off With Mommy

Come here baby boy, these tits were made for sucking. Mommy loves her little adult baby. But he knows I’m not like the other mommies. I’m so sweet and nurturing I take care of his every need. I make sure my baby boy always has a clean pamper on his little bottom, and a paci, bottle, or Mommy’s own swollen and milky nipple in his mouth. I make sure he gets dressed up like my little sweet boy, and I take my time using him to take photos and make money off of. So many of Mommy’s other clients love humiliating adult babies, and I sort of get off on it, too!

Anal Sex Mommy

While I dress him up int he cutest little baby boy bonnest and a sexy adult diaper, I make sure my baby has a rattle and his paci too! Let’s not forget that I have to get him ready to make this special movie with me. Mommy has her perverted PDaddy Adult Baby Rape Fantasy having degenerates to come over and film something special where Mommy dresses up and pegs her baby boy. I have to get his little poop chute all ready to take Mommy’s massive strap on! I can only wish I had my own cock to penetrate that innocent little hole with!

He’s going to thank me while I hurt him because I told him to, and his little pee pee is going to be rock hard inside that soft, cozy adult diaper! I’m going to make him so desperate to go pee pee in his diaper so I can make him have a humiliating bathroom pee emergency accident! Mommy is quite the fan of omorashi and wetting, and being able to degrate and humiliate my little adult baby boy Roger Thomas Martin is my favorite thing!

Breeding Phone Sex

 

Sissy Maid Training with Mommy

sissy maid training

It really makes me happy when I get calls for sissy maid training. It’s so much fun to help a sweet sissy like you who loves to be of service to others. I think that’s pretty common for sissies, but usually, it comes in the form of cock sucking or something sexual. But I’m told fairly often that transforming into a feminized maid is a huge dream of sissies everywhere. Their tiny little clitty cocks get so excited when they’re all dressed up in a proper maid outfit with hair, makeup, nails, and of course, a pair of sexy stilettos.

Can you imagine yourself prancing around in your heels with your feather duster? Imagine how cute you’re going to look and how sexy you’ll feel. You will probably even get more than money at the end of your cleaning session if you do a great enough job. Aren’t you excited about that? I wonder what your “bonus” will be? He might let you give him a blow job, but you could get really lucky, and he’ll fuck your pussy really deep and hard. Either way, I know you will be happy with the payment you receive for your cleaning services.

Milky Milf

milf phone sexYou love this milf phone sex whores big milky tits don’t you baby! I get so turned on when you want a drink, my sweet little boy. That relentless greedy sucking and moans make mommy so horny. Even grown men sucking on my milk laden tits gets me aroused. My panties are soaked now and I know that this is wrong, its incest with my little son. That milk spurting out over the sides of your sweet cupid shaped lips as you fondle the other milky tits, I laugh and decide to squirt a little milk down your face! Its time to sit on mommies stomach and put that boy fuck rod right between my milky mammary as mommy pushes them together and let you tits fuck in the milky cream I have lubed up my tits for you. Look at your boy cock fucking mommies titties! Mommys lovers love to titty fuck! Your being a big boy just like the men you watch fuck me! Its time for a mommy phone sex titty fuck full of milk and cock cream!

Suck It Up, Sissy Boy

Sissy boy mommy

 

I am the most hard-core and intense sissy boy mommy by which your wussy ass will ever have the pleasure of being owned.  My sorry little sissy slaves do exactly what I say because they know that if they don’t their asses will regret it in every way imagineable.  I have torture methods for disobedient sissies that would make your fucking head spin.  I might clamp down those puffy nips, hook them up to a few fuck machines and stuff them full of fake black cocks, coming at them from every direction, until they scream out in agony and dribble cum out of their laughable little clitty’s.  To get more out of them, I’ll strap them up to a milker and force load after load of runny sissy splooge out of them that they know I’ll make them drink.  My pathetic little piss ants better do exactly what I say or there will be hell to pay. I’m gonna dress you up like a pretty little whore and make some money off your wussy pussy and that tight little ass of yours, you pathetic sissy bitch.

 

Flock of Sissies

Sissy boy mommy

 

I fucking love being a sissy boy mommy!  I have a whole flock of sissies at my beck and call just waiting for me to give them some depraved attention.  They love being my wimpy little whores and dressing up sheerly for my enjoyment.  I make them dress themselves in front of me in some mismatched slutty panties and old lingerie while I describe to them how every piece of clothing they put on will be torn off of them.  I slap some shiny pink lipstick on their thin lips to make their milquetoast mouths look like a target for all the thick cocks I’m going to make them take.  Their mushy maw’s and wussy pussies get stretched and abused by anyone and everyone that I choose.  They gladly do whatever fucked up things I ask and I can tell they like it because, when I laugh in their pathetic little faces, their little clitty’s get so hard!  They don’t get to touch them, though, not unless I say they can.  They’re my sissies, they belong to me.

 

Sissy Boy Mommy Play

sissy boy mommyThis sissy boy mommy is on the Rag for Christmas and My son already knows what’s up! Mommy needs her pussy cleaned up and her cramps relieved by his mouth. And you know every time I change my Tampon, he needs his boy pussy plugged up too. But it’s more than that. I always have to pee and he drinks it with such gusto! Drinking mommys pussy juice is more than my cum and mommy Honey for him. I push his little face deep in my cunt and grind so he gets every last drop! I had my best milf friends over today. And I explained that my son was a little different than most and he needed to have his period right along with me. My friends were delighted that I took the time to properly train him. But they wanted to show off their way of taking care of their needs. One was was more interested in the new strap-on I had bought for our Christmas day activities, And wanted to fuck him like the little whore in heat he was. I was so wet at the thought of another woman fucking my son with her mommy whore dick that I just had to let her be the first to strap fuck my little sissy slave son! I had one request, to suck my son off as she had him on his back and he ate my pussy! So as I brought him in the big bathroom for his changing, one of the mommies showed him how she changed her extra super tampon with a hairy milf pussy and the other strapped up to fuck his boy pussy. Mommy and her friends would love to do some sissy training phone sex with you, two mommies are better than one!

Mommie’s Creampie For Christmas

Mommy son phone sex

Mommy knows you have been sneaking in and watching as she gets fucked by a big black cock. This year for Christmas mommy has decided to give you a good creampie. I will bring my boyfriend over and you will be ion the room. I’m going to make you suck on his big black cock and big balls so you can get him nice and hard for mommy. When he sticks his cock deep inside mommy, I want you face right by his balls so you can get a good view of that big dick going in and out of mommy. I want you sucking his balls making sure they get nice and full for me. When he is ready to fill me up, I will make sure I take every drop in my hot wet cunt. I want to give you a mouth full of gooey nut for you suck and eat out of mommy. Merry Christmas baby I hope you love your creampie. 

Mom with big tits for Xmas

mom with big titsAll he wants for Christmas is a mom with big tits. I told him Santa Mommy is checking her list to see who is naughty or nice. The naughty boys are the ones in the panty drawer and shoe collection jacking it like a crazed maniac, behind mommy’s back. The nice boys are the ones with cocks over 8 inches who fuck mommy just right! Deep, hard and right in front of her sons! I even classify some of my raunchy P-men who love to play with my offspring as Nice boys, wink wink!
There might be room for more “nice” boys on my list. The ones who let mommy dress them up so pretty and use her mommy dick on them, so we can both get off. Or the extra naughty boys who get a bit more of mommy and her man friends than they can handle! You know my cock sucking little faggot boys who cant get enough BBC or boy butts in their life! With all the naughty John boys and Robbies out there they need a lump of something in beautiful faggot buttholes. But don’t you worry boys this Santa mommy whore knows just what each boy or P-man needs and I have a Sleigh full of pussy and ass for you all.

Sissy Mom Candice

sissy mom

A sissy mom Knows how to take care of that wee penis. Or shall I say clit? My own son is not extremely small for a man, rather just an average Joe. He has always dressed up in mommies pretty playthings and asked to be used as a girl during our incest play times! It has never failed that my sweet dumpling wanted to be ass fucked by his sister with mommies super duper strap-on! I have to say he is my Pretty boy whom I can’t get enough of. I sucked his panty clad “Clit” and his freaky sister pushed deep in that boy’s pussy. My son makes such sweet moans of pleasure that I have to reach down and finger my own milf pussy! This is what I love about double teaming him with my daughter! We use up that sissy hole and get clitty juice and then invite our Bulls over. Soon, my son will be sucking cock and taking a real dick up his ass. Until then he must be satisfied with eating mommy and sisters cream pies out! Wouldn’t you like to dress up and be my fluffer? Mommy is waiting for her sissy boy!