Tag: sissy boy mommy

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!

 

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!

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.

Jack Off with Mommy Christina and my barely legal mini-mes!

Jack Off with Mommy Jack Off with Mommy Christina and my barely legal mini-mes. Since I’ve realized the demand for their bald young slits I have decided to have them home-schooled. That’s right; Mommy gets to play the role of a naughty teacher during the day and a sleazy cum whore by night. My girls love it when they get to put their pencils down and spread their slender legs apart. I always make sure to put the phone on speaker so the girls can hear your perverted thoughts word for word. My 4ft sex doll gives the best Deepthroat blowjobs! I had her tonsils removed to help with her gag reflexes and boy has her cock worshiping skills improved. She stands the perfect height, you don’t even have to bring my Breeding whore to her knees, that is unless you want her to be.

Her bald firm pussy lips, I always prepare with my wet tongue before having her swallow up your big daddy cock, balls deep inside of her dime-sized flustered hole.

She may squeal a bit, but have no mercy! My girl knows that pain is a pleasure… Once you get to thrusting her tight little rigid walls will clench around your cock and self-lubricate. You will see for yourself that I am what my slutty mini-me aspires to be. Don’t worry babe, I will be right there beside her… I do prefer she ride your cock reverse cowgirl so that I can butter her naturally bald lips as you slip in and out of her. Oh honey, and if by chance you are into a rare entry I am a Sissy boy mommy… My boy has a point to prove after all, being the only boy in a house full of girls.

Sissy Boy Mommy Nicolette Enjoys Panty Boys and Sissies

sissy boy mommySissy boy mommy Nicolette loves panty boys. I kind of earned that nick name a few years ago when I caught my middle son’s best friend in my panty drawer. The boy grew up to be a panty wearing sissy boy. Although he is an adult now, he still enjoys visiting me for some special play time. And I never mind his visits.

To this day, Mark still claims that no mature woman has a closet like mine. I am an old school woman. I grew up in the 80s when women loved pantyhose, stockings, thigh highs and sexy little outfits. However, my oldest daughter puts on a thong and calls that lingerie. Nonsense. Lingerie should entice men, feel comfortable on a woman, and leave something to a man’s imagination. Men require a nice visual for erections. I consider it part of foreplay to dress pretty.

So, when Mark discovered my sexy closest, it awakened the sissy boy in him. And I never mind being a sissy mom. When I discovered his love for panties, bras and hosiery, I nurtured it. A good mommy recognizes when a boy needs special encouragement. However, Mark and I bonded when he was a teen boy. Now, our relationship has blossomed into something very special. He lacks a woman like me in his life. His own parents tried to beat the “gay” out of him.

I Love Sissy Boys

Mark appears to me less gay and all sissy. Although he does transform into a pretty sissy when he visits me, he does not demonstrate much interest in glory holes or cock sucking my lovers. He just likes the freedom to dress up and prance around in my sexy undergarments. When he comes over, I let him pick out any outfit he wants to wear, and I help feminize him with a wig and makeup.

Mark would make a lovely Maria. Naturally femme body. Soft curves and skin. High cheek bones. Beautiful features. Sissy training phone sex helped Mark get in touch and nurture his femme side. And I enjoyed being along for the ride. Perhaps you might enjoy my big sissy closest too?

Lenora catches her sissy slut son.

Sissy boy mommy

Lenora Catches Her Son 

Lenora had been a single mom for as long as she could remember. Raising her son, James, had never been an easy task. So, when she stumbled into the living room one night and saw James doing something she’d never expected, she could hardly believe it. There in the half-light of the living room was her son, locked in a passionate embrace with another boy, their mouths closed around each other. She was a Sissy boy mom. 

Mommy Lenora stood there quietly, letting the moment unfold, until she decided that it was time to talk. She walked over and knelt down in front of them, and explained that it was okay, that she had been there once too. James looked sheepish and admitted that he had been exploring his sexuality, that he had just been curious, and it wasn’t anything serious.

But Lenora wasn’t one to leave things at that, she wasn’t content with leaving her son’s sexuality unchecked. So, she began to explain the basics of proper cuck sucking: the pleasures of using one’s hands and tongue. She was determined to make sure that her son could experience the fullest pleasure from his activities.

For the rest of the night, she instructed James as he sucked and fucked his little friend. She helped them apply lube and showed them how to explore each other’s bodies. They both knew that despite their awkward beginning it was the right thing to do.