Category: Sissy training phone sex

Wet Mommy Pussy Didn’t Save You? Time For Sissy Maid Training!

wet mommy pussy

I Thought Wet Mommy Pussy Would Save You…

It turns out wet mommy pussy wasn’t enough to spare you from the bullying. Who would have thought it would get worse! Today 3 of your bullies came up to the house. I was handling it again, but there you go walking in early again. I was already getting pinned down with a cock in my mouth and one in my ass. At First, I didn’t even see you walk in. I only noticed when they started picking on you. I swear I tried to say something, but he was pushing his cock so far down my throat that all I could do was moan. 

…But It Turns Out I’m a Sissy Boy Mommy!

Your mommy had to watch you get your first round of sissy maid training. The two boys that weren’t inside of me were pushing you around. Then one of them noticed the tiny tent in your pants. One held you down while the other one pulled your pants down. I never knew your cock was so tiny! And neither did they. They decided to show you a real dick. Then they forced you onto your knees and said they were going to make you their whore just like your mommy. They slapped your face with those sweaty teen cocks before forcing it into your mouth.

You fought it at first. But then I watched you start swallowing those dicks. You were slobbering and choking on their cocks. You even had your hand around it stroking. My sissy boy were salivating and your tiny little dicklet was still rock hard. Then when he came in your mouth, I watched you gulp down his entire load. You almost suck cock as good as Mommy. You didn’t even try and fight it when the second bully pulled out an even bigger cock. I could basically see the hearts in your eyes. It turns out I’m a sissy boy mommy. And now you’ve made some new friends!

Mommy is your Bloody Valentine

Mom with big tits

Mom with big tits Is a period-sex MILF for her dirty boys. My Valentine started off Bloody as you can imagine. Mommy Has some heavy periods, and the first thing my son sees as he awakes is me. Standing over I’m with my robe open, holding onto my stomach.  My tits bounce in his face as I say… “Baby Boy? The cramps are hard this month, I started overnight on my shift.  I’m afraid I might be quite a big mess masturbating in my red river.” I show him my red-laced hands, and he licks each fingerwith a smile. My boy already knows what time it is. Time to clean mommy up and help her cramps before she lays down for her nap. 

He leads me to the bathroom and takes down my panties and starts lapping my cunt and ass. With his teeth he pulls out my tampon. God, it is so hot when he does that! 

Soon I squirt a nice period orgasm in his mouth and follow with a hot stream of Mommy piss!

Having a son so well attuned with my body and willing to clean it up is one of the best things in life. 

The second best thing is that After mommys period is plugged and she has came hard, is giving my boy his period too! Three days at school this week with his period, it really was a good Valentine’s start! Yep, I am a period sissy boy mommy and he has his period every month with me! 

Mom with big tits Is a period-sex MILF for her dirty boys.

As My boy gets naked I bend him over and fill his boy pussy with a nice big syringe of my own blood collected mixed with theater prop blood. It is a sugar and mommys essence blend in his tank! Ha! No matter he walks with a swish! 

When my son gets home from school and I see if the lezzy nurse or his bestie has helped him with his period. I send plenty of tampons, but sometimes he needs to be helped or help a synced up lady! 

The third best thing is after mommy is refreshed and awake after school, she gets cleaned up and has a nice period 69 with her period boy! But that’s not all. Mommy happens to own the biggest dick in the neighborhood. 

Trust me if you like getting fucked in your boy pussy and period sex I have the mom fantasies for you my dear! 

Sissy mom Ireland loves all her sweet sissy slut babies!

Sissy mom

One of my favorite things to do with my sissy sluts is to make them look pretty. I am the queen of make up and I take great pride in making sure that my sissy’s face is perfectly slutty. I always choose a bright red lipstick for my baby sissy’s dick sucking lips because let’s face it, a sissy’s lips should always be ready and willing to please a real man. And let me tell you, I am going to make sure that my baby becomes a pro at sucking cock and pleasing men in every way possible.

But being a sissy is not just about looking pretty, it’s also about serving and obeying your mommy. That’s why I make sure that my sissy babies are trained to be the perfect maids. You need to know how to clean and tidy up mommy’s holes! You need to know how to please your mommy. I am always filled up with cum and I need my sissy to be able to clean it all out for me. After all, that’s what good sissy maids are for.

I may sound like a strict mommy, but I promise you, I am also a very loving one. I take great care of all my sissy babies and I make sure to give them the best training possible. And let me tell you, your tongue will love it! I will show you exactly how to please and serve your mommy, making sure that you become the perfect sissy slut.

So, if you’re ready to embrace your sissy side and become the best little sissy for your mommy, then don’t hesitate to give me a call for some sissy boy phone sex. I promise to make all your sissy dreams come true and turn you into the sluttiest, most obedient sissy you can be. I can’t wait to meet all my sweet sissy babies and give them the love and training they deserve.

Mommy phone sex with the beautiful mature and sexy Christina

Mommy phone sex I overheard my daughter’s boyfriend jerking his cock with a Mommy phone sex whore. He was moaning out my name and demanding I drop to my knees and catwalk to my girl’s bedroom. I didn’t know whether to be upset or indulge in the moment… Well, my hot cunt decided for me and I found myself stuffing my finger in my cunt while listening to the filthy words that slurred out of his mouth.  He had to of had so much lube on his cock, I could hear the sloshing noises his palm made as he dragged his palm up and down his big dick.

I guess I couldn’t blame him after all I lead him on… Night after night hearing my Breeding whore making Sexy moaning noises while calling him daddy has put some pretty wild thoughts in my head. I intentionally wear no bra whenever I know he’s coming over so he can see my hard nipples poking through my spaghetti-strapped tank top. I pair that with a pair of leggings that outline my perfect shape and always make sure to put a g string underneath so he can see the lining.

When I heard him grunting as he released the Biggest cum shot I had ever witnessed a boy his age shoot, I tapped on the door… I did not give him enough time to get cleaned up. Right after I knocked I entered and found him sitting there with cum all over his hands and the sheets of my girl’s bed. He seemed a bit nervous as I questioned who he was just talking to… After a few minutes of me standing there, he admitted that it is hard to resist such a hot Mom with big tits like myself. I told him I would keep it our naughty secret.

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! 

Anal sex mommy has a sissy slut following in my footsteps

Anal sex mommyAn Anal sex mommy like me has an addiction to being an anal whore… Such an addiction I just so happened to rub off on my son! He loves getting his pussy fisted and I found out for the first time when I walked in on him fucking himself with my dildo. He thought he would be in trouble so I had to promise him that I wouldn’t tell his father. If his father ever found out our son was a sissy he would have probably beat the brakes off of him… Luckily, he didn’t find out until my son was well overage! My boy showed up for our Christmas dinner this year with his cock inverted and a set of double-D implants. My husband’s jaw nearly fell off his face but it was too late to shame our boy for his faggot ways.

Being a Sissy mom has always been such a fun adventure for me.

My boy or shall I say girl and I have taken on many cocks together. I mean, after all, he wanted me to keep his dirty secret and well I used that as an excuse for him to keep mine. I taught him how to suck and fuck, all those tricks my boy does, he got from his mommy. I was the reason for his first anal fuck! One of my tricks was over and well he wanted a piece of my son’s tight ass. I without a doubt put him up for the offer… I got myself an extra wad of cash on top of our original pay. My son had no idea his cunt was paid for and still doesn’t until this day. I sat back and whipped my clitoris as I watched my boy get his mangina stretched by a real cock for the first time!

My Wet mommy pussy was filled with a hot load after he got through popping my boy’s cherry and I must say it was one of mommy’s best fucks ever.

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!

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!

 

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.