Tag: SISSY TRAINING

Painted Rose – Swimsuit Shopping w/ Step-Mom SPH JOI

After finding you that you have only a tiny dicklette, Mom takes you shopping for a new swimsuit. Obviously you can’t wear trunks anymore. She talks extensively with the sales girl about your tiny little penis-clit. You are quite embarrassed as Mom picked out a tiny micro thong for you. You should be humiliated for even thinking you could impress the shop girl. You must face the fact that you will always have to jerk off to your Mommy or use your two fingers. You try humping Step-mom to prove you can do it but there isn’t even a wet spot. What a disappointment.

FEMDOM, MILF, MOMMY ROLEPLAY, SISSY TRAINING, SPH

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Countess Jezebeth – Step Mommys Sissy Girl in Panties

Did you really think I wasn’t going to notice all my panties missing? You better tell me exactly what you were going to do with those, young man. You better feel ashamed of yourself right now. Tell me or you’re getting a spanking. You know what, I have something else in mind. How about you put those panties on for step-mommy! Come on, amuse me. Show me that you’re sorry. I want to see what a stupid little sissy bitch you are. From this point on you’re no longer my boy, you’re my girl now. That’s right, turn around and show me that tight sissy ass in those lacy pink panties. You’re such a little slut for step-mommy, let’s see how far we can take you, panty bitch. keywords: roleplay, step-mommy, panty thief, panty sissy, sissification.

SISSY TRAINING, MOMMY ROLEPLAY, FEMINIZATION, PANTY FETISH, FEMDOM, SFW

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Opaline4u – Step Mom Turns you into a Sissy

Your stepmother always knew your secret. She knows that you spend a lot of time thinking about cocks and that you love wearing sexy lingerie. She always dreamed of having a girl, to dress like a doll and now she starts training you as a perfect Sissy. She even brought some toys to play with you. A remote-controlled butt plug for your ass and her favorite toy..a big black cock.

SISSY TRAINING, FEMINIZATION, MOMMY ROLEPLAY, JERK OFF INSTRUCTION, TABOO

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Miss Madison Stone – Becoming Stepmom Sissy StepSon

Come here stepson I need to speak to you about something….. Do you have anything you would like to tell your stepmom? I saw some things on your computer, do you have anything to confess to me? You tell me just baseball but I found some kinky things when you went out today and forgot to lock your computer. I found some stepmommy / stepson things. Have you been fantasizing about me? Don’t lie to me! Now if you’ve been fantasizing about me I want you to get down on your knees and kiss my feet. Has my beauty been too much for you? Have you been jealous hearing stepmommy in the bedroom getting fucked every night? Have you been masturbating listening to me getting fucked? Didn’t I tell you to keep your headset on when my boyfriend is over? You’ve been a bad boy and deserve a spanking over my knees. I have a long spoon to spank your ass with and it needs some discipline. Have you been thinking about my pussy? Have you even seen one before, you’re still a virgin aren’t you? Well you don’t need any other girls, just me. Is my pussy everything you imagined? Wanna sniff it? Come here and take a sniff, but no licking…. only my boyfriend gets to do that and he’ll be doing that later tonight. There is be no masturbating when he comes over because I’m putting you in chastity. You know I never told you my fantasy but I’ve always wished you were a girl. Soooo I want you to put on this sissy outfit and pull down your panties for more spankings.

TABOO, MOMMY ROLEPLAY, MILF, SISSY TRAINING, SISSY SLUTS

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Lucy Skye – Mommy Edges the Sissy

I found out that you’ve been wearing my panties and prancing around like a sissy faggot…. As your mommy, I decide to punish you by making you stroke and stroke, over and over, while staring at me and smelling my panties. You’re probably wondering, “well.. what’s so bad about that???”… Well, since you’re a perverted little sissy I’m not going to let you cum 🙂 Nope. You have to edge forever, sniffing my lingerie and evening making you rub your dick while wearing them. I might even make you do some humiliating things like sucking a dick for me. How much of a slut should mommy turn you into?

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

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Painted Rose – Mom’s Bull / Your Bully: Sissy Cuck So

Mom (Stepmom) has a new boyfriend and they have been sneaking around. Mom decides to tell you and when she tells you it’s your old bully from school you can’t believe it! How could she? Mom’s a hot and horny cougar MILF and he use to make your life miserable and now Mom wants you to be friends? You agree to try for Mom. He comes over to take YOUR MOM on a date. What the hell, his dick is hard in his pants! So disrespectful. Mom asks if he needs taken care of! She tells you to watch so that maybe you will start wanting a girlfriend. No way! After a bit of her blowing him, Mom notices how hard you are. Mom guesses that you like Big Daddy Dick. Mom tells you to watch how a real man takes charge and face fucks her. You’re stroking. This dude pops a LONG and BEAUTIFUL Multiple cumshot in your moms mouth and a HUGE pile on her tits. Mom tells you to get a taste for this dick by eating the cum off of her tits! Mom says they will consider training you as their Sissy if you do good in Cuck Training! This is a Custom Video.

BULLS, CUCKOLDING, MILF, MOMMY ROLEPLAY ,SISSY TRAINING

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Miss Amellia – Step-Mommy Humiliates Sissy Boy

I am really tired of finding out that you’ve been stealing my panties . I thought you were just masturbating with them ,but .. well , last night , when I was going down to the kitchen I noticed your door was open .. and you were quite clearly in my panties .. Like ,to me if you’re just masturbating with my panties would at least means that you’re straight .. but this just yelps : sissy ! So , since you wanna be a girl so badly .. I’ve got some goodies for you and you’re gonna do that on my terms ! I’m not pleased I raised a faggot either…

MOMMY ROLEPLAY, CEI, JOI, SISSY SLUTS, SISSY TRAINING, SFW

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