Tag: SISSY TRAINING

Goddess Wolfe – Mommy Will Spank The Embarrassment Away

After Ms Wolfe’s ‘step’-son left for the Halloween party, She went to go clean his room and found a couple spanking paddles and a cane. Since She had already called him out on liking to dress like a girl, dressed him in Her old maid costume, and given him a lesson in sucking cock, She figured She night as well stay dressed in Her latex, take the toys, and wait for him to return home from the party. Ms Wolfe is taking selfies on Her massage table when Her ‘step’-son returns home from an embarrassing experience at the party. Heartbroken that Her own felt so humiliated, Ms Wolfe offers to help take the embarrassment away by inflicting pleasurably painful spanking sensations. Though first doubtful of engaging in such an activity with his own ‘step’-Mother, he agrees to try… and of course… it helps. ‘Step’-Mommy always does!

SPANKING, TABOO, SISSY TRAINING, FEMDOM, MOMMY ROLEPLAY

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Goddess Emmeline – Mommy Sissy Girl Training POV

With Goddess Emmeline! Mommy never wanted an icky and disappointing boy. You know Mommy really wanted a good GIRL. So now I’m going to turn you into Mommy’s Sissy Girl FOREVER. Oh, you don’t want to be a girl? Too fucking bad. Shut and listen to your Mommy. Obey and do exactly as I say and I’ll teach you how to look, talk and dress like the good girl you were meant to be. Follow all of Mommy’s sissy training and you’ll make Mommy the happiest Mommy in the world!

MOMMY ROLEPLAY, SISSY TRAINING, CROSSDRESSER, FEMDOM, SISSIFICATION

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Goddess Wolfe – But Mom No One Wears Costumes Anymore

Ms Wolfe is not like a regular Mom. She’s like a cool, weird, intuitive, hippy Mom. So, when Her son tells Her he’s about to head to a Halloween party, dressed in his normal “boy” clothes, She just can’t allow it… Of course, Halloween is the one day of the year when it’s most appropriate for all to let their freak flags fly! So, Ms Wolfe is delighted to help Her own dress up in Her old maid costume. As She transforms the boy She birthed into a slutty maid, She is sure to discuss how different it is for boys and girls attending parties… and how this sexy little maid must be prepared to please all the horny boys that approach her…

FEMINIZATION, TABOO, SISSY TRAINING, MAKEUP, SLUT TRAINING

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Mistress Stone – Pov You’re Mommy’s Sissy Little Boy

This is a POV video where I’m your Mommy and you’re my sissy little boy. We’re spending out special, secret tome together. I’ve bought you a pretty new dress that I want you to wear. I’m a nurturing and caring Mommy who loves her good little boy so much. I feed you your bottle with juice in it before giving you your pink pacifier. I then take my tits out for you to suck and nurse on. I love you sucking on my tits. My sweet, pretty boy’s spot is getting hard and Mommy’s spot is getting wet. I talk to you sweetly and then instruct you to cum while sucking on Mommy’s tits. You’re such a good boy

MOMMY ROLEPLAY, FEMDOM POV, SISSY TRAINING, POV, TIT SUCKING / NIPPLE FETISH

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Stacy Sadistic – Mommy Catches Sissy With Gay Porn

When I walked into my daughter’s room, and found her masturbating, you can imagine my surprise. When I saw her watching gay porn, I was shocked! Ok not that shocked, the little sissy had always had a way about her, and I’ve definitely caught her checking out hunky studs before during those fruit of the loom commercials. Being the caring supportive mother that I am, I wanted to make sure she was doing it right. I watched her wank for me a bit, but it wasn’t really working until I figured it out. She’s a little bottom! I needed to play with her hole if I wanted her to truly experience some sissy pleasure. After fingering her for a while, I decided to give her what she’d really been craving: a big hard cock up her ass. She wanted to get it just like those cute little twinks got it in her lil pornos. I wanted to make sure she had a good experience her first time, and break her in properly. I told her the boys can get a little rough, so it was better to practice getting slapped around by her Mommy first so that she knew what to expect. I showed her all the best positions, until finally I had to bust. My cute lil princess was right there and ready. She caught every drop of my hot jizz all over her pretty face.

ANAL, BIG DICKS, CUMSHOTS, SISSY TRAINING, MOMMY ROLEPLAY

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Princess Fierce – step-Mommy’s Dirty Whore

You’ve been stealing step-MOMMY’s panties and bras and I am going to teach you a lesson. You will have no manhood left as I orally and anally plunge your fag holes while you’re mentally stimulated with gay porn. I am going to transform you into my slutty step-DAUGHTER by putting you in my bra and panties and making you watch gay porn as you bounce and ride step-MOMMY’s dildo. I never had a step-SON I always knew deep down you were a girl.

COERCED BI, STEP MOM & STEP SON FANTASY, ANAL MASTURBATION INSTRUCTION, CLIT DICK, FEMINIZATION, GAY HUMILIATION FETISH, GAY JERK OFF INSTRUCTIONS, SISSIFICATION, SISSY, SISSY SLUT, SISSY TRAINING, STEP-MOMMY FANTASY

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Goddess Arielle – Mommy’s Little Whore

You need to get a job and start paying rent if you want to keep living under my roof, but who wants to hire someone like you? Your lazy, barely-legal and your only hobby is getting off to gay porn all day long. Don’t worry, sweetheart. Step-Mommy has the perfect solution! I’m going to help you put all of that porn-watching faggotry to good use. In fact, we are going to take it one step further! You’re going to get all dressed up like a little sissy slut and with Step-Mommy’s help, you are going to be all dolled up and whored out on a street corner. Having your throat and asshole fucked on the regular will have your share of rent paid in no time!

IMPOSED FEM, MOMMY ROLEPLAY, SISSIFICATION, SISSY TRAINING, GAY MASTURBATION INSTRUCTIONS

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Siena Rose – Momma Rose’s Sissy 4k

Momma Rose has just adopted you so she can turn you into her new sissy slut. I make you over and give you the prettiest lingerie, gorgeous dresses and thigh highs. I’ve set up a pretty nursery to keep your youthful sissy self in. I discuss our ground rules and I tell you my expectations. I need you to let my boyfriends use your asshole and destroy your holes. If I chose to have a date with a man I expect you to clean up all of my cum filled holes and to nurse on my cum covered titties as you clean them up. I expect you to use your slutty skills on the streets to make me money so we can maintain our beautiful lifestyle together. There is lots of visual stimulation, outfit changes and explicit narratives in this one as well as several ass closeups while I instruct you to be the best sissy slut for me! This was a custom script and the name is used a couple of times. (Will be re-editing soon to remove those, but def worth watching NOW!)

SISSIFICATION, SISSY TRAINING, FEMDOM POV, SISSY SLUTS, MOMMY ROLEPLAY

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