Category Archive: Sissy mom

Sexy Sissy Boy Mommy Regina


sissy boy mommy
The best part about being a sissy boy mommy is the spankings! My boy was being watched by his uncle Steve and I got an unexpected phone call while I was out with the girls! My son had called to tell me that Uncle Steve was very upset with him and to look at my Snapchat! My son was naked wearing my brand new expensive Nylons! Naughty, naughty boy. I made sure to let him know that uncle Steve was going to spank him when I got home to go to mommy’s things! Plus, he shouldn’t wear only nylons and no panties or bras! If your going to be a little sissy fag, you must go all in! I raced home thinking of the spanking that young tight boy ass was going to get. My mommy cunt was soaked and all this mommy slut could think of was how to punish my boy more. My sissy boy son didn’t expect me home so soon. He was in my make-up and wearing my heels just shaking his pink balled little cock like it was 1999! I pulled him by his little weenie right to his Uncle Steve, who looked pleased to spank my young sissy fag! I made my brother steve Strip to his Skivvies and I dropped my little black dress revealing little covering my hot milf body! I told my son as he got spanked that he would be pleasing my cunt and Uncle steve. I might be a sissy mom, but I have needs too. And my little faggot son made me miss a good dick, so i was going to masturbate while he was spanked red like an apple!
sissy mom

phone sex whore stepmom

 

phone sex whore

My stepson hears me be a phone sex whore. This has been my guilty pleasure, but I love that he hears me get so many guys off, and I love that I know he’s jerking his dick. I tease him all the time after a call. I am usually wet and fucking horny, so I go ahead and mess with him for a bit. I haven’t let him get his rocks off with me just yet.

I like to tease boys and want them to beg practically. I have a special place in my heart for boys that are about to become men. I like to help them cross over, so I do admit I like being their first.

I know that from that moment on, they will always compare every girl to me. Quite frankly, no girl will ever even meet the standards I set. My stepson will forever have the longing for my pussy even after I am long gone from the picture because I don’t like to stay in a marriage for long. I like to target my next victim.

Domme Mommy Whore Cuck Queen

Recently I had this little bitch in need of some training. He was going through some hard shit with women. I hear all kinds of stories from my callers, friends, son and my lovers. Honestly I have heard it all. However every time I say that another strange constellation is thrown my way. This young man had quite the story. Sometimes I feel these are made up and they can be quite imaginative. Then, I remember that Jerry Springer show and that should really give me the precursor to expect the extreme.

As I preluded here this little bitch has been put in quite the predicament. He had a a small fucking cock and that damned little thing couldn’t get hard for women. In fact he found himself craving to wear silky underwear. He felt the men’s satin underpants had bulged too much for his clit lump. He came to me in dismay and confusion.

Obviously, the first thing was to get him in some woman’s panties. Oh why not sissy panties. Yes this was the beginning of a transformation of this pathetic lost little man. He was such a big man in the eye’s of his clients and accounts he controlled. But when t came to pleasing women, himself or any kind of pleasure, well he was a bitch. We started sessions and soon got him to become a full fledged sissy.

Mommy whore

Getting knocked up!

wet mommy pussy

A week ago I put up an ad on craigslist “hot sicky loads wanted and needed for pregnancy!” I had 7 big black cocks waiting at my hotel room door the very next morning! I knew I was ovulating from how soaking wet my cunt was. I need a thick cock in me right the fuck now! I had a thick black cock in every hole. my mouth, my tight fucking ass, and my dripping wet cunt all were being forcefully and violently pounded and fucked! my little whore cunt was already on the verge of oozing from my own cum when I got a hot steamy load in the back of my throat that sent me over the edge as I came all over the cock that was pounding my pussy he couldn’t help but the cum deep inside of me! by the end of the day my holes were gapping and filled with so much cum i could’ve bathed in it. I can’t wait to be a slutty mommy and not knowing which got me preggers.

Mommy Polly Makes Sissy Slaves

MILF Phone Sex

Mommy Polly rules the roost of milf phone sex. I’ve decided to delve into the world of training my sweet sons exactly how to serve and service women outside of my usual breeding, PMommy, and ABDL skillset. I know the exactly level of tender, loving care my pussy needs to stay in shape. She needs groomed, cleaned, and played with every single day. Don’t even get me started on when Mommy gets her period. That’s a very special time for my darling boys, as they get to experience what it really means to be a woman. Some of my sons as straight sissy faggots, and there’s nothing to be done about that. I’m making the best of it by training them into my own personal sissy hand maiden slaves.

My little boys start young licking my delicious mommy cunt and sucking on my clitty. They beg me now to play with their pathetic clits, but I only let them cum on their birthdays, if I can be bothered to remember that. My mind is always full of being bred by delicious thick cocks, not on making my sissy slave sons in chastity get off. I will make them cum if they can pay me enough.

My sons started buying me Amazon gift cards, determined to earn my favor. If you expect to cum, you’d best tribute Mommy and remind her how much you’re my favorite. Swallow my cum, slut. Watch Mommy fuck this zucchini. Pay attention on how I like to be fucked, and how a real man would fuck this pussy.

Sissy Training

Sissy Greggies Mommy Whore

mommy whoreLittle sissy bitch Greggie is quite a pathetic whore. Mommy Whore hates it when she has to remind him to do things twice, so when I called his name a second time, I grinned.

There had better be a good reason my pathetic diaper boy was playing hide and go seek. I had sent him off to get a fresh pamper, some powder, and his wipes. He had made quite a little messy in his last diaper. However, my little bitch had been gone for too long! I caught him in the hallway jacking his pathetic little clit. I slapped him hard on his bare bottom and dragged him by his ear back to the bedroom. Bending him over, I spanked him real fucking good! Then, I called his BBC Daddy to come in, and force that thick chocolate monster down his throat! I’m going to change you now, baby. I hope you enjoy a fresh, clean pamper while you suck on your cum filled ba-ba!

If you’re a good boy you can have these heavy milky tits to suck on while I stroke that tiny clitty! Come her baby, all you need is a sissy boy mommy to make you all better!sissy boy mom

Domme Mommy Phone sex Vacation W/Stepson

mommy phone sex

Your mommy phone sex lover had a  marvelous mini vacation with my step son! It was supposed to be me and my husband but he got called to work. Oh, No! That meant I got to use, I mean … invite my step son to go with me to a couples retreat. I sure did want to see what my new step sons cock looked like. He was so shy as we hit the nudist beach, a nice normal dick, one that made me want to jump the incest train already! Had me thinking my girls would love to break him in as well. But first the massage tables as I reached for his hand. Everyone assumed he was my much younger lover. No idea how much younger and that made me hump the massage bed as I was getting my muscles limbered up. The hot tub was next and I made my move, jumping in my step lads lap and french kissing him as I jerked him fully hard! I needed pussy attention, so I climbed out of the hot tub and spread my legs and demanded him to eat my cougar pussy. Such a shy Lad! He went to work slurping and eating as best he could. By the time we got to the room I was throwing him on the bed and straddling his cock. “Make mommy Cum, I ordered, I pumped my wet mommy pussy up and down and milked that boy cock deep in my cunt! But I had other plans, plans he had no idea his daddy liked certain things. My pegger 3000 was long and hard as I swatted that ass and made me get on all fours for me. It was time to ride my boys ass as I jerked him hard and fast. This milf is always in control! The sperm puddle on the pillow shows that! This Domme mommy always gets what she wants! 

Cum To Your Sissy Boy Mommy!

sissy boy mommyIt’s a special time of year for this sissy boy mommy! See, I have men who have lost their panty wearing ways and they are coming back to their sissy life! Such and exhilarating and pussy dripping time for me. I love men in panties, and just because you haven’t worn them in a long time does not mean it’s never too late to put them back on baby boy.
Take my Sissy Greggie, he called mommy up to tell her he likes panties but hasn’t worn then in so long. I made him march right over to that panty drawer, I knew he had a stash! He picked out the softest pretty yellow pair and my shy sissy went from demure to dancing around the living room in those perfect panties. I tell you a pair of panties can change your whole day! ❤


Mommy was so excited as Greggie thanked her and asked if that sweet little clitty could make a wet spot in those yellow undies! I said yes baby, and we went on about how Greggie the sissy would wear frilly pantaloons and give her squirties yo me all the time. We even talked about diapers and cum eating too! I enjoy all mommy son phone sex sessions but Greggie made mommy cum so hard as this sissy boi begged to have mommy cum filled and eat her sweet mommy cream pie one day! 🍑

Sissy Boy Mommy For The Holidays

sissy boy mommy

I love having you as my sweet sissy and being your sissy boy mommy. Especially around the holidays it’s fun, because I get to dress you up in pretty Mrs. Santa and elf outfits. You look so cute, on your knees by the tree sucking the cocks of mommy’s boyfriends. they love coming over and having your mouth on their big dick. And you know my one friend loves when you bend over and spread your ass cheeks all the way apart so he can slide his massive cock in your pretty lil sissy pussy. It always makes him feel so good. Mommy is so proud of you for being a good slut. That means you’re going to get a really good present this year. I can’t tell you what it is, but let’s just say you’ll be really excited for it. I’ll tell you when you call mommy, but here’s a hint – it’s long, chocolatey, and it’s probably going to leave a big, juicy mess all over your face. If you’re interested in finding out what I got you, then just give mommy a call right now.  You are totally gonna make a mess in your panties and I’m going to have the best time watching you!

PMomma Polly’s Menagerie

Breeding Phone Sex

Momma will do anything to make a dollar. You see, I’m still in my breeding prime, and this juicy milf pussy could be yours for the taking. I can always make more brats, which is why for the right price, I’ll gift you one for a hefty donation. As you can see, I have sixteen lovelies to choose from. Yes, you heard me right. Momma Polly is prone to triplets, and those little redhead girls are my twins. The blonde boys, with the thicc teen girl are the quadruplets. I have a harem of innocents for you to choose from, so step up and tell me what you like.
If you prefer submissive house slaves, I might recommend my young Brynn, or perhaps her brothers, Blair and Synner. Those are some vivacious young cocks with attention to detail, and her sweet, flowering pussy is prime for breeding. No, you don’t want submissive sweetlings? You’d prefer a brat with some bite?
Momma Polly might suggest one of the twins, Arizona or Arya. Perhaps you’d like both? These young ginger goddesses are at the perfect age for picking. They’re little firecrackers, but have proved to be passionate little lovers beneath the sheets. Either or will please you, but together is better. Are you a nasty PDaddy who would love a visit to my little angelic harem? I have someone for you Daddy, I can guarantee it. If the twins aren’t your style, or you’d like a mild cockslave boy to ride you, Momma Polly can provide your desires; for a price.

Jack Off With Mommy

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