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

Continue to download

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

Continue to download

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

Continue to download

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

Continue to download

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

Continue to download

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

Continue to download

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

Continue to download

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

Continue to download