Tag: SISSY TRAINING

Lildazey – Come sit on mommies big cock

You’ve been such a good boy, mommy wanted to surprise you with a new toy. I know you’ve been saying you wished mommy had a big cock to stretch your little asshole out with, well your wish came true. Come over here and let mommy fuck you while you suck on her big milky tits. I want you to bounce on mommies big thick black cock, she needs to get you ready to be fucked by her big stud friends. Don’t be shy B***.

BBW Domination, BBW Goddess, Big Black Cock, Big Tits, Mom Fantasy, Momma’s Boy, Mommy Domme, Sissification, Sissy Training, Strap-on

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MistressLA – Mommy’s perfect Girl!

You started out as such a beautiful boy. Dark locks, strong chin, beautiful eyes. I was hoping you would have the manly cock to go along with how handsome you were. As you grew I realized you were cursed with your father’s sad little prick. Looking at it makes me sick. So my dear boy, I have begun unbeknownst to you, hormone treatments. I have scheduled and surgery for your transformation. I have already redecorated and room, I have a few other changes in store for you as well. Since you have not become the man I had hoped you would be. I am going to turn you into my perfect sissy slut. Your journey starts now my sweet girl, let’s get ready!

Castration, Castration Fantasy, Coerced Bi, Female Domination, Female Strap-on, Female Training, Mommy Domme, Mommy Fantasy, Sissy Training, Small Penis Humiliation

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Goddess Stella Sol – Mother May I Stroke

Does Mommy make you horny? Yes! Very much. I know you like wearing Mommy’s bras and panties. My little sissy boy can’t help that he get so turned on playing dress up in Mommy’s clothes, and you’ve been found out. It’s time we talk about it openly, but don’t worry. I won’t tell. In fact you have My permission, and I want to play a little game with you called Mother May I?
While I’m doing laundry you sit back and watch Me try on different pairs of dirty panties while I encourage you to stroke. You’ve been sniffing Mommy’s panties, haven’t you? Yes. You like how Mommy’s pussy smells, don’t you. Very much so. Mommy moves so sexy, don’t I? Yes. Dressing up like a girl turns you, right. Yes. Yes. Yes. Only Mommy knows your secrets. Only Mommy can make you the hardest.
Follow along and enjoy how good Mommy is at teasing you. When Mommy says “touch your balls”, you do it. When Mommy says stroke you rub your dick for Her. When Mommy says cum, you stroke harder and faster while I tease the jizz right out of My boy.
Now be a good son and buy this clip because Mommy knows what’s best for you, and your big boy cock that’s all grown up now.

Category: MOMMAS BOY
Related Categories: SISSY TRAINING, MILF, THONG FETISH, EROTIC DANCERS, BIG TITS

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Sissy in Satin – Roxana Rae – New Mommy

Last night your mommy and I had a long conversation about you. She was very worried that your small dick was running your life. She expressed to me your lack of pussy and how your tiny cock hasn’t really grown that much since you were a baby. She told me you should have been born a girl and that she regrets not raising you as one. Maybe then you wouldn’t feel so bad about not getting any pussy. We decided that I will be taking over as your new mommy and that I will be feminizing you from now on. I think your new life as a girl will be more fulfilling and you will no longer have to deal with the pressures of the male role. Now sit down and listen to mommy as I go over your first new lesson as a girl.

Category: MOMMAS BOY
Related Categories: SMALL PENIS HUMILIATION, SISSY TRAINING, FEMINIZATION, SISSY SLUTS, PUSSY CONTROL

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Miss Penny Barber – Mommy Wants You To Try On Your New Undies

I bought these underwear for you and I don’t see why you won’t just try them on in front of me. Oh I see. Well don’t be embarrassed sweetie, It is perfectly natural for a boy your age to get excited over every little thing. Those briefs certainly will not fit over that stiffy of yours though. Is Mommy going to have to stoke you off so you can fit into your new undies?

Category: MOMMAS BOY
Related Categories: TABOO, MILF, PANTY FETISH, SISSY TRAINING, FORCED CROSSDRESSING

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Step Mommy Uses You As A Sissy Whore – dirtyprincess1983

I find out that you have been a little filthy pervert and jerking off to me. You will never be able to have me.. But you can be useful to me in other ways. Im gonna train you to be my little sissy pet. I want you to be a cock sucking whore for me. Im going to use you to earn money. Yu are gonna be my personal little slut.

Femdom, MILF, MILF Fantasy, Mom Fantasy, Sissy, Sissy Training, Slut Training

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Step Mom Whores Out Sissy Son – Vera Price

I need to talk to you for a moment. I understand I am not your birth mother, but that does not mean I don’t demand respect. You have not been pulling your weight around the house and it’s time to put a stop to that. I’ve seen your browsing history. I know you’re a fag. If you are going to be such a slut, I may as well earn a profit from it, right?
That’s why I am placing special ads up on Craigslist, just for you. Maybe if you do a good job I’ll rent your holes out for more than $20. Here’s a big, thick black dildo and a nice heavy buttplug. I expect you to get your practice in, keep those holes nice and loose for Mommy. Who knows, maybe your slutty ass will like being whored out. Now open your mouth for Mommy. I want to watch you slob this cock off just like it’s the real thing.

Category: SISSY SLUTS
Related Categories: MAKE ME BI, TABOO, BIG TITS, SISSY TRAINING, FEMINIZATION

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Mommy Embarrasses Sissy Son – Vera Price

Honey, I have had it with you stealing my panties. I’ve noticed them going missing and had just assumed you were being… gross. That is, until I saw you wearing them when you left your door cracked open last night. You thought I’d gone to bed already, but nope. I went to get a glass of water and saw…. That. If you want to be a sissy, that’s fine, but not in my clothes. Here’s some panties, a nice pink bra, and some lipstick. Put it on. You’re going to jerk off in your little getup and then you are going to eat your cum. That’s right, in front of me. Come on, we don’t have all night.

Category: SISSY TRAINING
Related Categories: TABOO, CUM EATING INSTRUCTION, MILF, MOMMAS BOY, JERK OFF INSTRUCTION

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Hot Juls Fetishes – Domme Mommy Teaches Cuckold Son To Suck Cock – Goddess Juls

CONTINUING “DOMME MOMMY” ADVENTURES……You are quietly sitting behind your mommy’s bedroom door, playing with your small “willy” and listening to her have sex with one of her lovers. You hear your mom’s loud moaning, she is saying to fuck her harder, and it makes you so hard…You love when your mommy has one of her boyfriends come over so you can hide and listen to their “sex”. You are just a curious cuckold son. You are excited seeing your mom being pleased by different men, but what you are most excited about is her STUD boyfriends.
The moaning stop and she walks out the bedroom discovering you hiding behind her door with your penis out, erect and stroking it. “OMG! what are you doing here? I told you the rules. When mommy has one of her special guests you need to be in your room with earplugs. Instead you are being a dirty little boy jerking of to your mommy having sex”. After scolding you about your naughty behavior, your mommy calms down and talks calmly about your sexual fantasies. She discovers that it turns your on that mommy has a boyfriend with big cock, and you have dreams about bisexual experiences. Being a loving mother she is, she decides to invite you in the bedroom and teach you how to suck her boyfriend’s cock…”He doesn’t mind!”. There’s no one better than your own mommy to teach you proper way to please a man. You ill do whatever your mommy says because she is your everything.
In the next scene , you are on your knees with her boyfriend’s cock right in front of you (POV virtual blowjob). “Oh you are drooling honey, don’t be nervous, i know you want mommy to teach you how to suck dick, especially my boyfriend’s dick”. Mommy grabs cock and slowly teases you, telling you all about how juicy his cock is and what a good little cuckold son you will become once you know how to please her lovers. She makes you suck his cock but she is too greedy to let you get his creamy cum shot first. After she finishes her boyfriend herself and gets a huge load in her mouth she turns around and says those magic words: “Come here , sweetie, try my lover’s cum. Have you ever tried a snowball? Let me spit it in your mouth….Put your lips on mommy’s lips….”
In the final scene you are fed lover’s load, but mommy sees you have a huge hard on. She knows how much you loved it. Without hesitation, she tell you to drop your pants down and stroke in front of her and her lover. She tease you with her sexy lingerie, her hot ass and of course the dirtiest talk you have ever heard your DOMME MOMMY say. Now, are you ready to please “your mommy”?

Category: CUCKOLDING
Related Categories: MOMMAS BOY, MALE CUM SWALLOWERS, TABOO, BISEXUAL ENCOURAGEMENT, SISSY TRAINING
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Hot Juls Fetishes – Cuckold Son In The Closet – Goddess Juls

You want to be mommy’s sissy cuckold son…You love when your domme mommy brings different men in the house and fucks them while you are hiding in the closet, playing with your little cock. It turns you on seeing your hot mommy being filled up by lots of different partners. You love it so much that now you are dreaming of cleaning your mommy’s used pussy after she has sex.
The scene starts with me (your domme mommy) getting ready to go on the date. I am applying my make up and talking to you at the same time, telling you all about my hot dates and how you became my submissive sissy cuckold son. “You know your mommy is pretty promiscuous and horny. After your daddy left you’ve been seeing different men in this house. How do you think i make money? Yes, some men pay with to have sex with them. I know you’ve been hiding in the closets and spying on me while i am in my bedroom being pleased by another man. You need to step this up and become my sissy clean up boy. I pay for everything in this house, so it’s time for you to serve mommy.”
In the next scene i am telling you to hide in the closet because one of my lovers is about to come in to have sex with me. I walk you over to the closet and tell you to sit there and not make a peep. “If you are a good boy for mommy, i will let you slurp up your first load! I know you are a sissy boy and i know you love watching me fuck”
In the next scene you are quietly sitting in the closet (POV cuckold view). You hear the knock on the door , some conversation then you see your mommy get down doggy style and start fucking. Then she lays on her back, moaning and enjoying another cock. (Virtual POV fucking). You can’t believe you are watching your hot mom having sex while you are in the same room, listening to her moaning, the smell of her pussy lingering in the room and you can barely keep it together in your pants.
In the final scene my lover pays me and leaves. I walk over to my son hiding in the closet and show him a delicious condom that he is going to devour. After he does everything i command him to do i will allow him to play with his cuckold sissy dick and eat his own cum for mommy.

Category: CUCKOLDING
Related Categories: MALE CUM SWALLOWERS, MOMMAS BOY, CUM EATING INSTRUCTION, SISSY TRAINING, TABOO

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