Category Archive: Sissy maid training

Sissy Boy Mommy Wants to Play

sissy boy mommy

Oh, I just love being a sissy boy mommy. When my son was younger, I walked into my bedroom one day and caught him wearing my panties and jerking off. He was embarrassed for some reason, even though I’d been playing sexually with him and his siblings for a long time. I told him he had no reason to be shy and that if he wanted, I would help him get dressed up in more than just panties. He reluctantly agreed and we went into my closet to find some lingerie and a nice dress for him to put on.

After he was all dressed up, he asked me if I would get my strap-on cock and fuck him. I was SO happy because I’d been hoping that one of my sons would be into that! I told him to bend over and I squirted some lube on his pussy and started to slide inside him. I got so excited that I reached down to touch my pussy and came almost instantly. Do you want to hear more about the things I did with my sissy son? Call me and I’ll tell you how I pimped him out to all of my male friends with enormous cocks.

Sissy Maid Training Mommy

Sissy Maid Training

I’m a slutty, slutty mommy who believes in sissy maid training for my sons to be disciplined for me. It makes me so happy when I have the opportunity to transform my sweet sons into little  sissies who cater to their mother’s every whim. My baby boy’s clitty is absolutely darling, and dressing him up in adorable frilly dresses with matching stockings, panties, and training bras is just too much fun! To make me happy, he said he wanted to do anything, so today he is my little maid and I can play with him however I please.

It’s the most adorable little French maid ensemble I’ve ever seen. He looked exquisite in his short skirt and thigh-high white stockings. I had ordered him to draw me a nice warm bubble bath, and since he was such a good boy, I let him wash my huge milky tits as well. Next, he proceeded to take care of Mommy’s hair. It felt really nice to be pampered by my son in his sissy outfit. Now that he did such a good job of taking care of me, I allowed him to enjoy himself after I had finished drying off. Until he came right in his panties, I rubbed his little peter through his sissy slut panties. Now for step two of Sissy boy phone sex with mommy Regina, Finding a cock to train him on, Mommy does have a nice big strap on to help open up that ass.

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

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 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!

Wet Mommy Pussy For A Sissy

Wet mommy pussy is an exciting thing for the naughty Sissy girls. Girly Sissy boys love to wear panties and lick a mommy twat. The best is a creampie mess in the honey pot of their mommy owner. I love my sissy son and get excited having her lap up the seed from a big hard bull cock. You know the first time she got the taste of another mans seed in my mommy cunt was when she was a sweet young thing, I trained her early on to enjoy my mommy pussy. My son was always loving to wear lipstick and dress up in mommy’s pretty things. I have managed to really cultivate this lad into such a good sissy slut and am so proud of my sissy son.

Wet mommy pussy

Whenever I am at home with a nice big alpha male cock fucking my mommy hole, my son is listening and trying to watch. He loves the sloppy sloshing sound of my mommy pussy getting penetrated and fucked into a wet frenzy of a mess. My son knows better than to disturb us. He knows that alpha bull dick is not going to want anything to do with his cucky ass. Not unless he comes in the room dressed like a sissy slut and ready to be a little bottom beta whore for that alpha daddy dick.

Pregnant Mom Giving Sissy Maid Training

Sissy Maid Training

 

 

Sometimes a pretty little fag like you needs a mom who can give you the sissy maid training you deserve! A very pregnant mommy who has huge titties filled with milk as a reward for doing so well. I can barely move with this brat inside me. I require the tightest panties and littlest cock cage on underneath as you are washing dishes. I want you to only have a little frilly apron on and come and rub your cage covered clitty on my hand whenever you need to ask a question of mommy. I will give you a drink after the full set of silver utensils is polished to a mirror shine. You can gulp mommy tit juice and rub my belly full of your little sister as you try to hump mommies leg. Then I want you scrubbing the tub and having your pretty ass up in the air as I move your panties to the side and stick your horse tail butt plug deep in you. Pulling and pushing until your tiny cock is bulging and hurting against your chastity. Satisfied I inspect the toilet and discover my sissy maid fag has left some dirt inside. I pull out the switch and demand that you lick the toilet clean with your tongue now! NO more milk until you learn to be a good sissy maid. You are my bitch and mommy Gabby controls you!

Mommy’s Sweet Little Sissy Boy

Sissy boy phone sexWith the house full and everyone stuck at home, it’s a lot harder for secrets to stay hidden from me. And my youngest boy has the sweetest little secret. Apparently, when mommy is away he likes to sneak into my room and dress up like me. Obviously my clothes are too big for him so for panties and bras, he sneaks some out of his sisters’ room. I found this out by waking up earlier than normal and found him in the guest bathroom modeling in front of the mirror. I gave him quite the scare and he quickly confessed everything to me. Apparently he is jealous of his sister being the only ones with pretty things, so I promised that as soon as we could, we would go have a shopping spree of our very own. Just for him so he can get pretty clothes in his own size and stop being a naughty little panty theft.

My Son’s friend cums on mommy

Phone sex mommy Phone sex mommy

The feeling of that long white man meat tapping on my ass was the best feeling ever. I love it when my son’s friend, Benjamin. Makes those clapping noises when he taps the head of his cock onto my ass as if he is knocking on a door. Then he slides his cock up and down the crack of my ass right before he sticks it into this wet mommy cunthole of mine. He pushes himself deep inside of me and just sits inside my pussy. I can feel his cock jumping inside of me. He is barely 18 but can fuck for hours. It’s funny because he can last so long but with me. Only a couple of pumps and he pulls out and cums all over my ass. He massages that sticky cum all into mommy’s ass like lotion. This Milf still has some good pussy! Come try mommy out for yourself.

Sissy Maid Training BBC loving Preggo!

sissy maid training

I recently was told that sissy maid training would be my best profession as I love to humiliate my husband with chocolate cream-filled cock impregnation of my young tight body. I went to a sissy festival with my kind and generous and prissy husband. We all know why he took the role of my hero husband. Not because he felt bad for me but because he wanted kids and his dick craves BBC. It is a win-win situation. I get fucked the way I should be and have sweet mixed fuck tots that can be used however please and my sissy Lala hubby gets to be my new sissy maid and have all the inches of black nigger cock he could ever dream of. The first lesson was on frilly clothes and undergarments. My husband dropped two grand on new pretty clothes and panties and garters. You name it he bought it And today we are going through basic house rules. He will eat (sometimes BBC) as a girly priss pants, He will drink (sometimes Nigger cum) as a delicate feminine lady. He will clean my feet with his tongue and any other body part I wish. And the number one rule is to keep me supplied in BBC baby batter so I can be the cuckolding preggo sissy trainer I was always meant to be. Now excuse me while I milk my tits to make a cum and mommy milk smoothy for my bitch sissy hubby!

Older posts «