Category: Sissy mom

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.

Sissy boy mommy Ireland will make your little clitty bust!

Sissy boy mommySissy boy mommy Ireland will make your little clitty bust! I’ve been around the block a few times and I know a thing or two about how to satisfy your insatiable hunger for cock and cum. I’ll make you moan and beg for more, my sweet boy.

I know what you really want, deep down inside. You want to be sissified, don’t you? You want to be my pretty little princess, all dolled up in frilly dresses and high heels, with your tight little bussy just begging to be abused. I am more than happy to make that fantasy a reality for you.

I’ll take you under my wing and teach you everything you need to know to be a good little whore. I’ll show you how to suck a cock like a pro, how to take it deep in that sweet little throat of yours until you’re gagging and crying for Mommy’s approval. And when it’s time for that bussy to be filled, I’ll make sure your hole is stretched out to take thick hard cock. 

I have a lot of friends who would love to play with that hole. You will make Mommy a lot of money by whoring out your slutty holes. I’ll make you crave cock and cum, and beg for it like a good little slut. And get ready baby because you are going to take cock after cock, because let’s face it, Mommy has bills to pay, don’t I?

So what are you waiting for, my little bitches? Pick up that phone and call me for some hot Sissy maid training. Mommy will make your tongue numb by the loads of cum you will clean out of my juicy pussy and ass. I will mold you into the sluttiest, most obedient whore you can be. And trust me, once we’re done, you’ll be begging for more. So come on, my sissy darlings, let’s get down and dirty together.

 

Cock sucking mommy Polly Wants to play!

Cock sucking mommy

 

Cock sucking mommy Polly needs her little brat boy’s cock. I saw you watching me as I was in the shower. Eyes wide drooling with that massive cock rock hard in your hand stroking it imaging all the things you want to do to me. Well how about you bring that dick to me baby! I want every inch of that cock to stretch my tight little holes out. Im a cock obsessed cum hungry whore and nothing makes my pussy gush with excitement more than a young man with a long massive cock jerking off to the thought of me.

Since I’ve noticed you watching me every time I put on a little show for you. Ill bend over right in front of you in my tiny little skirt with no panties while your on the couch watching tv. To give you a peek of my sweet pearl dripping. Watching me on all fours swallowing the cocks of my new breeders seeing me slobber and drool all over their cocks while they fill each of my holes up.

I cant help but gush just thinking about it. Can you make mommy cream? I want you to breed me baby boy!

Mother in law phone sex

Mother in law phone sex

I know your type. I see the way you look at me. You married my daughter, but what you really want is mother in law phone sex, isn’t it? My daughter is gorgeous, and you know it’s true, but I did teach her everything she knows. So maybe you want to give me a try? You know I’ve been around the block a few times.

                I know you guys are visiting for dinner tonight. Ask your wife, my daughter, to run an errand. Maybe we forgot to buy something important for dinner. Then we can sneak upstairs and do a few things. It wont take long. What is something that my daughter can’t do in the bedroom? Can she put her legs behind her head like this?

                I want you to fuck me with that monster cock, deep within my pussy. Balls deep really. I can do all sorts of positions, but I really want to feel you in my womb. You make me cum like no other man has. My daughter is a lucky girl, but I guess I’m the lucky one at this moment.

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?

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!

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.

Anal sex mommy loves cummies deep inside her brown eye

Anal sex mommyMy life can be summed up by calling me an Anal sex mommy. My ass is perfect for catching big thick creamy loads. As I tell my slutkins, ass play is a natural part of life and it feels so good to be opened up. Do not be shy when you come see mommy regina, I like it up my ass and it’s okay if you do too. But even if you don’t want a finger or tongue up that beautiful asshole, mommies are available for use! 

Although I do love when my brats get tied up to a pole and that as sis creamed with Peanut butter for some very naughty roleplays! I digress, all This sexy Milf wants you to know is that I love butt fucking in every situation.   So come on down and let me show you how much I love a good ass pounding.

Anal sex mommy loves your cum in her shit hole!

Pull aside my black panties and look at mommys tight little ass pucker. You may give it a kiss or just lube it up with my honey. I sure will suck you hard and ride your cock a little before you push in my brown eye.  Mommy wants to hear your moans and feel your pleasure as I slide up and down your shaft. I’ll be sure to cum with you, and then we can do it all over again.

Jack off to my Horny milf pictures and feel yourself slipping in this milfs ass! Doenst that feels so fucking good as i moan and cry out how good your cock feels inside my shit hole. Bend me over an take what you want right now, Mommy Regina is waiting for you. 

Fuck a Milfs ass hole and let loose all that yummy cummy!

mommy Regina is your anal cum dump!

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.