Tag: sissy boy phone sex

Anal sex mommy Regina always keeps it mixed up!

Anal sex mommyI’ll say it until my dying breath, being an anal sex mommy is what I was born to do. It’s time to have a big milky momma give you her shit hole to control. Are you up to the ass fucking challenge! My husband and sons recently dared me to an ass fuck fest, and who am I to resist?

Your hot mommy eagerly accepted the dare, knowing full well that this was what I have been trained for! Mommy Reggie is, after all, the infamous “Big Milky Momma,” and this will be my ultimate ass-capades! The room was filled with anticipation as I dropped my clothes and my hips wiggled with pleasure!

The asshole to be conquered, a timid young man, entered the room, his eyes wide with a mixture of fear and arousal. He could hardly believe that he was going to finally experience the full power and intensity of Big Milky Momma’s unholy lovemaking.

Anal sex mommy always keeps it mixed up!

“Do you accept the challenge, boy?” this sexy woman growled at him, my voice a low, seductive purr. The young man gulped, “Oh, did you think it would be my ass you’re fucking? I have other news for you!” Many men have come in this ass, and they are welcomed to jizz up my butt with that good nutt! But First, an ass virgin is what I REQUIRE! Jack Off With Mommy and fuck my ass or bring me a nice tight ass for my fingers and big momma strap. I’ll have you flat on your back bouncing my leaking mommy milkers all over your cock and balls!

Sissy training phone sex mom Valentine trains by affection.

            Sissy training phone sex mom Valentine trains by affection. Now you know that sooner or later I am going to be playing with my sissy son. If for no other reason than to make sure that you have learned all there is to learn from me. Going to whip you into shape. Stretch that pussy out. Give you all you got and then make you go a little further. At the same time going to be giving so much attention.

            To begin with I will come home and find you in my bathroom. All dressed in my lace panties and bra. Well now if I had known that you wanted to be a girl I would have chosen a much more suitable name for you such as Brandy. It is a fine vintage to be sure. Next going to show you how to apply the makeup. The first thing to remember when applying makeup is the coverup goes on first. Then you do the eyeliner. Now this can be any color, but a lot of people use a brown or a black. Give it an exotic look across seas with the tilt of the eyeliner. A little gold glitter and you look sexy.

            With attention to detail, you are going to need to wear clothing that fits you. Going to go to your sisters’ room where she is closer to your size and pick out some pink panties and bra for you.

          Sissy mom likes to play and teach her sissy son for his training. Sissy training phone sex

            Going to show you how to wear the garter belt. As can be seen I like to teach you and your training is really coming along. You need to stop interrupting me all the time and actually listen to mom or the affection is going to be less, and the whip is going to be harder. Pay attention when mom is speaking.

            As soon as we have you in the right bra and panties that are pink lace then I am going to put on my strap on at least as soon as I have stripped down to my bra and panties. Then you are going to be taught how a sissy bitch whore sucks on my dick. Afterall, you do want to please me now don’t you. That is what I thought. Once you have sucked on my cock and listened to the directions, I give you then we will take a break and you can clean my house while you are still dressed up as a little sissy bitch whore.

Let Meredith be your Phone sex mommy

Phone sex mommy

I love being a phone sex mommy. Mommy is here and ready to take full advantage of her little sissy boy. She’s going to dress you up like a good little boy, in high heels, a thong, and matching bralette. Do your make up, and make you look super sexy! Once you’re all dolled up, Mommy is going to do a little photo shoot with you. Do lots of poses in various positions, ass up, showing you bussy to the camera.

I want you to tease the camera, do what Mommy tells you to do like a good little sissy slut. 

Now Mommy is going to put the camera right up here on the table. Now we’re going to put you on live stream. Let all the other sissy boys out there see what a good boy you are for me. Dance and prance around in your sexy lingerie. I want you to feel nice and sexy letting everyone on the live stream see you all dolled up.

It’s okay, no one will recognize you, we did your make up so good you don’t even look like yourself anymore. Specially with that nice red curly wig that Mommy put on you, you look so cute in it!

Now I want you to sit on the bed in front of the camera, and bend over, grab some lube, and I want you to lube up your sweet little busy for Mommy. I want to show everyone on the live stream just how far open we can stretch your tight little bussy. Get it all nice and lubed up for Mommy’s big black strap on, this huge 10″ dildo will fit nicely right into your lubed up bussy.

Fuck yes you good little sissy boy, it’s sliding in nice and deep, take it all. Mommy is going to pull this out of your little bussy. I want you to get on your knees in front of mommy and the camera. Good boy, now I want you to lick your sweet bussy juices off mommy’s big strap on dildo. deepthroat it like a good boy, do what mommy says. 

I enjoy sissy training phone sex too. Now pick up your phone and call Mommy Meredith and tell her all the nasty little things you want her to do to you. Be a good boy, call me now. 

Sissy mom will punish and abuse just to soothe you.

            Sissy mom will punish and abuse just to sooth you. In fact, going to start with getting you all dressed up. Make up and all. You sit over there. Mom is going to break out her make-up. Not the good stuff. At least not yet. As soon as I know you can be a good sissy for your mom then we will discuss getting you your own stuff. Like blush, should be with the color of your skin. The first thing to realize is that as a mommy boy you will be subjectable to my whims. Pleasing me first and foremost.

            Next thing you know you’ll be Sissy boy mommy little bitch in your maid’s costume. Dusting the house. Wiping it all down. At the same time Mommy is going to be watching, filming, and even ordering you to show your little pussy ass. Quickly teaching you how to kiss, how to French kiss the pussy.  Going to have to find you a daddy or just a mommy strap on and introduce you to the ways fucking. Needs to enjoy the dick.

            Holding the dick in my hand. Squeeze you from the base on up. Suck on my tits. All for mommy for otherwise you need to be punished. Paddle the butt. Just to fuck the pussy. Beauty knows no pain no boundaries. To be the best you need to embrace the pain. Be good for mommy for after the punishment and abuse, to be sure going to soothe you. Making you cum with a combination of them all. Just wait and see. I will turn you into a Sissy who cums to pain.  Sissy mom

Sissy boy mommy for all adult diaper lovers!

Sissy boy mommySissy boy mommy for all adult diaper lovers! If you act like a helpless ABDL Bitch, don’t be surprised when I lose my patience with you. Some of you crave to be babied and pampered, but the good bois understand that you deserve to be humiliated for your Diaper fill-ups! And if you’re a humiliation junkie, then calling a Domme ABDL Lover like Mommy Regina is just what my itty bitty baby bois need!

I have just the thing to make your diaper feel full and tight. I have no qualms about pointing out your wee dinkies! Mommys Humiliation and diaper changes are exactly what you need to get your pathetic little pee-pee going, isn’t it? Mommy Regina is here to make your Diaper fantasies come true. Let me take care of all your ABDL needs!

Sissy boy mommy for all Small dicked adult diaper lovers! 

Now I force you to fill your diaper up for me.  You are going to feel the humiliation and pleasure of being fucked by your mommy, and I want you to cum for me. I want you to thank me for humiliating you and making you my little diaper boy.

I want you to imagine that you are on all fours, your padded ass exposed to me, your diaper bulging with your piss and shit! Mommy is ging to cut a hole in your diaper and fuck you with her strap on! My tits are leaking as this Domme Mom Takes Lactating phone sex to extremes for ABDL Bitches like you! I love a nice mess and fucking a full dirty diaper of an baby boi ass slut like you is going to make a hell of a mess.

Drink from my big dripping mommy milkers and stay in a constant Age regression space mixed with ass fucking and Small penis humiliation!  Cum, now wee one, Let me take control and make you my bitch! I will make you my little cum whore and you will become addicted to me. Obey Mommy and give in to your ABDL desires.

Mommy Regina is here to make your Sissy boy phone sex Diaper fantasies come true. Let me take care of all your ABDL needs!

Sissy boy mommy will do your make up.

  Sissy boy mommy          Sissy boy mommy will do your make up. Make you look like a beautiful little sissy and no one will ever be the wise. After all you mommy knows what is best for you. First we will pin all your hair back. Now the reason for this is so that you don’t smudge and smear the make-up when we do the hair. A point often overlooked is a wig should have the hair pinned back or a net cap put on.

            Giving you charcoal eyes. This is thick eyeliner around the entire eye. Smudge it ever so little. As can be seen it draws attention to how high your cheek bones are, how wide your eyes. Next is the lipstick. Ruby reds, magenta, bright colors will draw attention to the full mouth.

            Smack your lips together and say ahh. Another key point when you are out to eat be sure to get dick shaped objects to slowly put into your mouth. Be a good sissy boy and eat it slowly. Dab your lips. Hence keeping the lipstick.

            Most notably in your handbag you need to carry some lipstick (same shade), some extra eyes shadow, and of course the lip liner. Wherever you go these are essentials. Now before I let you go out. Your Mommy wants to have Sissy boy phone sex and peg you after you suck on my strap.

            All in all, I want to make sure that you are ready to go out on your date. Make me proud.

Cock sucking mommy Son shows her whose really in charge

Nothing makes me happier than being a Cock sucking mommy. Yesterday I decided to treat one of my sons after school. He came home from track practice all sweaty and hot. He came into my room and caught me playing with my pretty little pearl while I was watching porn. I saw his eyes widen and the bulge in his shorts grew I could see the lust inside of him growing and without a second thought He came over to me and began to rub on my titties while stroking his ten inch cock.

Next thing I knew he had me bent over on the bed as he rubbed the tip of his cock up and down my pussy making me gush and cream. The moan I released once he slid inside of me was like a breath of fresh air. I relished in every deep long stroke it sent vibrations all over my body. the thrill alone made me never want him to stop.

He fucked me passionately and deeply on my marriage bed for hours filling each and every one of my holes to the brim with cum. I love that my sweet boy knows how to please his dear mommy. I taught him everything i knew and last night he showed me he knew so much more.

Phone Sex Whore Nicolette Enjoys Sissy Boys Too

phone sex whoreI love being a phone sex whore. My husband built me an office space and it has a beautiful desk, and old-fashioned phone and a closet of sexy lingerie. I am old school, I guess. Perhaps it is because of the generation I grew up in, or maybe it is the reaction I get from my sons and my boy toy husband when they see me in old-fashioned lingerie. Likely, it is a combination of both.

Garter belts, stockings, thigh highs, teddies, baby doll nighties and bra and panty sets galore in my office closet. For some boys, the feel of my sexy lingerie sparks something inside them. And I think that is part of the reason I show off so much of my sexy lingerie. I enjoy being a sissy mom. Although none of my sons show any sissy inclinations, I have allowed several of their friends over the years play in my lingerie closet.

My youngest son has this femboy friend who comes over often. He is not the typical boy. I have caught him several times playing with my lingerie and dirty panties. He is not jacking off in my items. Rather he is trying them on and exploring his sexual identity. As a mature woman, I know a sissy boy when I meet one. Last night Chris came over to spend the night. And I caught him in my office closet. So, I confronted him. However, in a nice, non-threatening way.

I Love Being a Sissy Mommy to Sissy Boys Too

When I asked him what he liked about my undergarments, he just let loose. So, I gave him a sissy makeover. Even though he is a young teen boy, I think he knows he is not the typical macho boy. And I assured him that was fine with me. He wants me to be his sissy boy mommy and I told him I would be honored.

My son got a little upset because I hijacked his gamer friend. His father played video games with him while I played dress up with the young boy. He has naturally feminine features. Appears to lack any masculine features or an alpha boy personality. So, he is perfect to be my next sissy boy project. Do you think you might need a sissy mommy too?

Sucking Dick for Mommy Whore Eva is What You Love

Would you say that you crave to suck cock with a Mommy whore like me? Perhaps you would be like one of my regulars and just be a total cock sucking ham and record yourself being a good cock sucker.


Ultimately, many of my callers, all perfectly sane and successful professionals have sucked dick. There really is no reason to shy from this craving and innate desire to feel a pulsing penis in your mouth.


As I ave been in the Phone Sex Business for over a decade. In fact I have encountered many types of men on my lines. Some of the best ones are men that just want to please their mother. In such a way that they get to be a cuckold to her (or me). Of course this is really exciting.


Finally there is just really something sexy about a man. It’s that he is not afraid to discuss his sexual fixations with me.

Even if he is one that would not exactly go out and do what we discussed. The brain is quite complex especially the sexual desires and cravings when the horn comes on.

Mommy Whore

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.