Category: Sissy boy phone sex

This Sissy Boy Mommy is Ready for Sissy Maid Training

Sissy Boy Mommy Wants to Cage Up Your Clitty

Your sissy boy mommy is ready to play. Is my sweet girl ready to play dress up with Mommy? I know you like to sneak into Mommy’s bedroom when I’m not there, and try on my sexy panties. We can’t have that can we? I thought it would be better if I got you a couple pairs of your own. And maybe a couple of cute dresses for you to wear around the house when no one’s home. But in exchange for the pretty pink clothes, you have to lock up that clitty for me. Ok, my pretty sissy whore?

sissy boy mommy

Cock Sucking Mom Milks You for Sissy maid Training


When you’re dressed up as my little girl, you won’t have a use for that useless sissy cock. So I’ll put it in a cute pink cage and lock it away for you. Your panties will look so much cuter without that oversized clitty pushing through the top of them or stretching out the front. Mommy knows it’s a big change. So I’m going to make it a little easier by being the cock sucking mommy you know and love. Pretty girlies deserve to have their clits licked and you are one of my prettiest girls. Let mommy make you feel good before I turn you into my princess.


You lay there and relax while I tease your clit and sissy pussy with my tongue. You sound so cute and girly when you moan. And this sissy fuckhole is all lubed up and ready to use. Mommy’s going to push one of her special toys in that sissy ass for you. I’m going to fuck you like that cute sissy slut that you are. I want to see my pretty baby go cummies all over yourself. Come on baby. Don’t you want to taste your own cum? Be a good girl for Mommy.

Wet mommy pussy and boy pussy need fucked on the daily!!!

Wet mommy pussyWet mommy pussy needs to be fucked daily.  I have no qualms in telling you how much of a whore I am. I need my pussy pounded daily.  Your mommy knows how much you love licking this milf slit, too! You don’t care how many creamies I get or if I’m on my period. You’re just a nasty little boy who needs to be between my legs constantly. And if you are anything like my little Eddie, you really understand how much mommy needs to be fucked.  My Eddie is a special case in that area! See, I have a bad habit of staying up late and keeping his friends entertained. 

When my special little guy has friends over they always end up in mommy Regina’s room getting serviced and high! My sweet boi doesn’t mind at all. Because when they have had their fill of mommy pussy, or one of my male friends is there, they just use Eddies Boy pussy! 

Wet mommy pussy and boy pussy need fucked on the daily!!!

Being a Sissy boy mommy has its advantages. Because my sweet little sissy girl confides in me all of the naughty things that happen to her.  It’s my little secret and I enjoy hearing all about it. My sweet boi also gets rewarded for being a good boy and getting the pleasure she deserves. It’s a sexy sissy situation for both of us. As a good mom, I make sure that My sweet angel has that boy pussy filled up whenever I can. Shit, sometimes I send her to try that cock out so mommy knows if its worth fucking and sucking! 

Mommy Regina loves getting fucked, and loves making sure her sissy boy gets fucked too! Mommy son phone sex for sissies and boys who need milf cunt! 

Sissy boy mommy Tina enjoys turning stray boys into sissies

Sissy boy mommy I am a Sissy boy mommy! My boy loves being pegged… He gets so excited when I bring horny men home with Big black cocks to share with him. I found out about his sissy ways one day after catching him prancing the house in my used panties. He wanted his fresh little clit to smell just like momma’s pussy. That’s when we dug deeper into exploring his sexuality! I introduced him to my sex dungeon and all of my toys… He confessed to fondling his asshole using his fingers… But I told him I had something much bigger and better than that. I slipped into my self-thrusting strap-on dildo and had him gag and drool all over my sex toy.

This was only the beginning of Sissy maid training, he was soon dressed in lace daily and left to do all the womanly duties around the house.

This was how he earned his next serving of creamy cum! His behavior depended on his serving, whenever he was a naughty sissy slut. I tease him with my drooling cum filled cunt; while telling him how good it felt to have my pussy stretched. He is to then get down on his knees and I instruct him to give momma a cum clean up. When he is on his best behavior I always make sure to bring home a nice meaty big black cock. His feminized moans always let me know how thankful he is to be able to serve his newest daddy. Being a Sissy mom is the best thing that has ever happened to me!

Jack Off With Mommy and her sweeties full of creamies

Jack Off With MommyJack Off With Mommy as she goes over her week of sexual indulgence. My sweeties are all at home and don’t go back to school until after the new year. Mommy has a sore pussy and ass, but it is the best feeling from my own bebes. My daughters are so happy with the sexy nighties and new real-feel dildos i gifted them. My sons have some sexy silk boxers and I stole some of Daddy’s Viagra for them! Hence the sore whore holes I have now.
My mommy cunt is overflowing with creamies! My daughters have shown me how much they learned by giving expert blowjobs to daddy and brother cock. This P-mommy Milf couldn’t be happier!

Jack off with mommy and her sweeties!!!

Sweet Phone sex mommy Gets her icing piped in right from her own slutkins. The amazing family sex this winter is going to keep getting hotter! Cum partake of a wild Milf who loves to share her young sluts and boys cocks with you. I know I have some men who love being a daddy dick spinner while eating boy cock. And others well you can slurp my ass and pussy. It is the end of the year, why not go out with family gang bang of extremes? You know I can handle you, baby! So can my sweeties, or I will make them take it!

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Wet mommy pussy tastes so delicious!

Wet mommy pussy

Wet mommy pussy tastes so delicious! I’m horny mommy and proud sissy trainer! I’m here to show you all the fun and wild ways to find ultimate sissy pleasure. Whether you’re in it for the pleasure or for the humiliation, it’s a delicious experience! I’m 100% confident that I can provide you with that, baby!

I pride myself on being an expansive, no-holds-barred teacher in sissy training. I know all the tricks and I’m not afraid to go all out. You need to get the most out of your experience. I love to be creative and make sure that there’s always something new and fun to try out every session. My goal is to help you discover a part of yourself that you never knew existed.

Let this Sissy mom show you how to really use the tools of the trade to properly suck, lick, and fuck until you can’t take it anymore. Not only that, but I also take pleasure in teaching you how to properly take cock like a true sissy, so that you can experience the full range of pleasure that sissy training has to offer.

I can guarantee that you’ll be truly aroused, and perhaps even a bit ashamed of your own debauchery, after you’ve gone through a session with me. With my help, you can feel secure in knowing that you’re making the best of your sissy fantasies and desires.

All in all, I’m here for you, sissy. Say my name and call me to book your next session for some of the hottest sissy training around. Just think of all the amazing cum that will ooze out of your pussy hole after a few hours of my unique style of training. Cum-draining orgasms and fulfillment await. So come on over and let mommy Ireland show you who’s boss. Call for Sissy training phone sex!

 

Mommy phone sex Regina Caters to Men in diapers

Mommy phone sexMommy phone sex for diaper boys who need something a “little” different. Are you wee-wee feeling the need to be squished up in a nice four-tabbed Adult diaper? Or maybe it won’t go squish Becuase it’s truly a lil boys weenier that gets confined to diapers by a mean mommy! Either way, I have the Lil Kings and accessories to boot for your sweet bottom.

Adorable Adult baby diaper lovers cum in all forms. And some never get to cum at all, do they?  ( Looking at you Robbie The Bratty boy! ) Just simp in your widdle diaper at mommies display of ABDL fun playthings. My question is have you been good or bad for mommy a good boy today? Are you ready for mommy’s punishment? Or will you continue to be naughty?

Mommy phone sex can be mean or nurturing for ABDLSLactating phone sex

Mommy Regina Has mommy milk, diapers, and cock cages at the ready for good and bad lill boys

Besides hot big full knockers for Lactating phone sex we have so many ways to play! Mommy Regina will be sure to find out which one is best for you. Don’t worry, Shh baby boy, Mommy won’t tell! Just because I found you cowering behind the playpen in a very sagging dirty diaper isn’t the end of the world.

No matter how much of my milk you take you still love that warm cozy feeling of wetting and shitting yourself. “Oh, Baby why can you not stop playing in your dirty diapers? Nasty lil baby! Mommy knows it’s hard to resist that sweet pecker. But now your hands are all messy and mommy has a big job to do now! 

This is a world where you need a good mommy to help make you clean and dry. Mommy will feed, burp and change your rank ass. Phone sex mommy regina Loves her wittle men so much! Never fear your Mommy for ABDL is here!

 

Huge tits phone sex Mommy Loves Gay Pee-pees

Huge tits phone sex

Huge tits phone sex Mommy Loves Gay Pee-pees!  As a mommy piggy whore I understand why men sometimes love cock. I’m stroking my wet milf pussy to a gay peepee with a dildo in his faggot fuckhole!  I’m such a dirty piggy whore! I love cock and cum so much! I want your gay peepee to blow for cock now! Listen up I have major skills with strap-on fucking and consider myself a peg queen. I would make a mommy sandwich out of you with one of my son’s big cocks. Go ahead and get dressed up with me and a nice big fat tranny cock. I love the stories my men tell me of cock sucking cum eating fags. 

Huge tits phone sex for sissy fag pee pees

Anal sex mommy Regina is a fag hag and I love my gay boys sharing cock with me. Even better when Mommy can dress them up first to be her sissy slave! Men who are exploring taht bi-curious side need a Hot milf to show them even if you have a big fag pole you can still have fun with other big cocks. So get ready to look like a pin-up bitch and get that mouth and ass pussy used up when we have some sexy fun together.

 I want you to feel my strap-on deep inside you. I want to explore every inch of your tight ass.  Let me hear you moan as I fuck you harder and harder. Beg for more. The hottest is you screaming my name as I fuck you into oblivion.

I’m waiting for you to come and explore your bi-curious side with me. Let’s have some amazing fun together. I’m ready to welcome you with open arms right into these big tits.  I’m an experienced Sissy mom and I know just how to drive you crazy with cock. Mommy iswaiting for you to come and explore your pegging side with me. What are you waiting for I’m strapped and ready.

 

Sissy boy mommy Ireland is going to pimp out your pussy!

Sissy boy mommy

Sissy boy mommy Ireland is going to pimp out your pussy!  I’m your mommy and I’m here to make sure you’re the most perfect sissy slut you can be. I’m going to dress you in the softest, silkiest, lacy panties and ensure your little clitty is tightly caged. Everyone will gasp when they see how cute my sissy slut looks in her pink dress and pretty face as if I had created my own little China doll.

I want you to adapt to the role perfectly, so I’m going to teach you everything there is to know about being a sissy breeding whore. There’s no need to worry, I’m here to take you each step of the way. First, I will take you to a group of select men of my choosing, they will be ready and waiting for you. You will have to take on one cock at a time. Show each man what a filthy little whore you are! They will fuck your face so hard, all that pretty little make up will be smudged. I think you would look absolutely adorable!

I’m sure you’ll become an expert slut in no time. After all, I’m not just teaching you how to be my little sissy slut, I’m teaching you how to be everyone’s sissy slut. Once you’re fully trained, you’ll be able to take orders from any man. If it’s humiliation, BDSM, or forced feminization men love, your sissy slutty training will turn you into a sex toy they can’t resist.

Most sissies complain about how hard it is to be the perfect slut. That’s where I come in. I will keep you on track with daily sissy lessons. We’ll role play, talk about the kinds of humiliating attire and spicy punishments that make them weak in the knees. Before long, you’ll just have to show off what you learn and they’ll be obsessed. So, are you ready to answer your mommy’s call and become the best sissy slut you can be? I think so!

Wet mommy pussy needs a sissy mouth cleaning

 I love a having a sissy boyson, “clean my Wet mommy pussy”. “It is a cummy mess” I say to my sissy boy as I spread my legs. “Open your mouth mommy wants to feed you” is what I moan out as I grab you by the hair. Once my sissy son’s face was between my legs, I squeezed my pussy hole. “Can you feel mommy trying to squeeze all the semen into your mouth?” I ask. Then your sissy tongue starts trying to scoop all the cum out of mommy’s cunt.

Wet mommy pussy

“You are hungry tonight sissy son slut”. While you licked mommy clean her boyfriend walks in. “Don’t wiggle your ass too hard sissy bitch, I might just fuck it”. After mom’s boyfriend says that you wiggle that ass like a bitch in heat. “Mommies sissy whore needs dick” I say as I giggle while fucking your mouth.  All of the sudden you scream into my pussy, and I look up. “Oh, you’re getting a big cock now” I say while laughing.

After that it didn’t take much before I started squirting into your mouth. Therefore, mommy’s boyfriend started pounding you harder and harder. Your sissy moans sounded like an animal getting fucked. “Please fill me up” you scream out. After hearing that mommy’s boyfriend started pumping all his semen inside you. It is always such a sight to see when your sissy cunt starts leaking all over for the semen overflow pumped inside you.

Sissy Boy Mommy Nicolette Loves Playing with Femboys

sissy boy mommyI find being a sissy boy mommy rewarding. None of my sons grew up to be sissy boys. However, they all have friends who enjoy feminization and other sissy boy things. And guess what? I enjoy encouraging these boys to be themselves. Nothing wrong with wearing mommy’s panties and sucking cock if that is what you want.

Instead of one of my sons bringing me a sissy boy this time, my husband did. His best friend from college is a lowkey sissy boy, but his wife will not indulge that side of him. Sadly, I hear that from my callers too. Well, that is why I am open to helping sissy boys like Tyler. I can be any boy’s sissy mom on or off the phone. Tyler’s wife even gave her permission for us to have some fantasy playtime. So, we ran with it.

Tyler saw my sissy wardrobe and he looked like Charlie when he first entered Willy Wonka’s candy factory. I mean this boy looked amazed. His eyes were as wide as the sky. I encouraged him to feel everything and wear what he wanted. He put on this lace catsuit I own and blossomed into a pretty girl. Do you know what happens to sissy boys when they put on something sexy like that? They transform. And they crave cock.

Sissy Training Mommy Helps You Suck Cock

Now that Tyler looked more like a Taylor, I needed to find some cock. I love my husband, but he never wants a male sucking his cock. I doubted he would want his BFF sucking his rod wearing his wife’s sexy garments, LOL. So, I took Tyler to a local glory hole. Usually, this cock sucking mommy is the one on her knees waiting for random cocks to peek through the holes.

Not that day. My pretty sissy boy blossomed in her feminine outfit and sucked cocks for hours at that seedy glory hole. I beamed in pride watching Tyler finally get some dick. I even helped him set up a Grinder account. Since his wife gave us permission, I am going to make sure Tyler gets all the cock he wants when he gets sissy time.

Maybe your wife is not as open minded as Tyler’s wife. But that does not matter. We can still enjoy some discreet sissy phone sex.