Category: Sissy Training

  • Mean Makeup. Mean Girl and the Dweeb (season 2 episode 6)

    Mean Makeup. Mean Girl and the Dweeb (season 2 episode 6)

    You're beneath me, You will always be beneath me… pathetic… but you're gonna thank me cuz I'm gonna guide you and make you into the perfect faggot eventually. Now I'm just gonna put a little makeup on you before school. Don't worry, no one will be able to tell, haha! Just a Step-Little Bronzer… oh and eye shadow… only I can see it… don't worry your faggity self about it. Just a little bright blue… that's it! Oh and some thick coats of mascara will just make your eyes pop. Now let's not forget the lipstick! Don't worry, dweeb, I know I said light pink but I think this dark red lipstick and gloss is gonna look much better on you, haha! Pucker up! Haha!

    Duration: 9 min | Price: $9.99

    Starring: Skyla Novea Tip Skyla Novea Directly

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  • Swallow That Cum. Mean Girl and the Dweeb (season 2 episode 11)

    Swallow That Cum. Mean Girl and the Dweeb (season 2 episode 11)

    I see your back, dweeb. Did your bully take it easy on you today? No??? Awe, come tell your loving step sister all about it… you look so tired. Were you scrubbing toilets and floors all day or was he fucking your throat like a sissy Slut? Why are you just shaking your head, why don't you speak deeeb, your supposed to say "yes miss" when I address you. Oooh, you have his cum in your mouth??? And your not allowed to swallow it until you got home? Until he gives you permission? Awe, that's so hot that he humiliated you like that tonight. Don't worry fag, I'm gonna be a good sister and call him for you right now. Hey, the sissys home and apStep-Parently has a mouth full of some studs cum, haha. I knew it was yours silly, does the dweeb have permission to swallow now??? Ok, I'll pass it on… ok babe, your such a real man, I love when you think of stuff like this! Ok babe, bye. OK fag, he said he wants me to get a quick video of you enjoying that cum with a Big Step-Sissy smile on your face. Ok go ahead and swallow Step-Daddy cum! Good little cum dumpster, now thank your Step-Daddy. Good sissy. Wow, you looked like you enjoyed that a little too much. Maybe we really did turn you gay, haha. Ya know me and Step-Mom never thought it would really work but I kinda wonder now about how much progress we've really made. Here, let's try something, I'll pose for you while you stroke your tiny cock and then I'll let you spill some sissy cum on my legs. Come on dweeb, whip that sissy clit out. Why are you hesitating? This is a huge opportunity for a sissy like you. Ohhh, you think it's a trick??? You think I'm gonna report you to your bully? Well you did give him a pledge and I guess he does kinda own your cock now, haha. Well I'll tell ya what, fag… I'll pose for you while you recite your sissy pledge for Step-Daddy. I'm sure you'll be aching to cum… but just think how hot that is that he's actually inside your head like this. He's got you so whipped that your turning down a hot girl and keeping your balls nice and blue for him! That's so hot, he's such a man. Now let's hear your sissy pledge! Repeat after me, -I'm Step-Step-Daddy's sissy maid and I will always obey him faithfully. -Step-Step-Daddy's superior cock is all I need. -I will ask to be punished if I ever look at pretty girls and get a tiny inferior boner. -if I even catch a glimpse of my sister in panties around the house, I will immediately rush over to my Step-Daddy and put on a thick lubricating coat of shiny pink lipstick and ask him to forgive me and beg to be face fucked. Oh, that's such a good sissy Slut. Now ya know, you did technically see my panties so… you know what that means! Yup, your gonna grab your pink lipstick and head right back over there and drop to your knees. I'm sorry, dweeb, but a pledge is a pledge! Bye fag.

    Duration: 8 min | Price: $8.99

    Starring: Skyla Novea Tip Skyla Novea Directly

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  • Your Bully Wants Dinner. Mean Girl and the Dweeb (season 2 episode 10)

    Your Bully Wants Dinner. Mean Girl and the Dweeb (season 2 episode 10)

    Good morning, dweeb. It's Saturday… time for the biggest chore day of the week for sissies. Oh my, that was a very pretty curtsy, haha. You're gonna be cooking for an extra person tonight. I've been blowing your bully so much lately that Step-Mom wanted to meet him. Isn't that cool. You're gonna get an extra chance to thank him for the things he's done to you and helping lose your sense of self-respect. A good sissy needs to be continually beaten down in every way to keep any manly pride from bubbling to the surface. It takes lots of energy for the family to constantly put you down… and it's so nice that your bully is coming over to help lighten the load. He's just gonna love your pretty pink maids outfit. Look Sissy, I've taken the time to write out a Little Step-Sissy pledge that you can entertain us with after dinner. Well, it's more of a sissy pledge to your bully than us, but hey… we're not gonna want to look at you all the time and the more you're over his house cleaning and servicing him, the better. I mean, his appetite for blow jobs is voracious and my jaw is getting sore just trying to keep up with thanking him for humiliating you. You're gonna have to self-sustain your own increasing humiliation by blowing him with your pretty pink mouth, sissy. Now we gotta practice your pledge: Repeat after me, -I'm Step-Step-Daddy's sissy maid and I will always obey him faithfully. -Step-Step-Daddy's superior cock is all I need. -I will ask to be punished if I ever look at pretty girls and get a tiny inferior boner. -if I even catch a glimpse of my step sister in panties around the house, I will immediately rush over to my Step-Daddy and put on a thick lubricating coat of shiny pink lipstick and ask him to forgive me and beg to be face fucked. Haha, that last one is so fitting, don't you think, sissy! Oh, and I do plan on walking around the house in my panties as usual. Maybe I'll have to add temptation just to fuck with you. I'll wear sexy lingerie and pull up my skirt and ask you if you wanna cum on my legs. Oh, I bet that would just drive you crazy huh? This is gonna be so much fun! Now practice your pledge and then start doing my laundry… by hand!

    Duration: 10 min | Price: $10.99

    Starring: Skyla Novea Tip Skyla Novea Directly

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  • Serve Me And My Friends. Mean Girl and the Dweeb (season 2 episode 9)

    Serve Me And My Friends. Mean Girl and the Dweeb (season 2 episode 9)

    The new lesson is that you're gonna bow down to me when I say bow, sissy boy! Look at my big tits that you wish you had, haha. Look at my ass in your face while you're on your knees! DO you see how beautiful I am! This is who you serve, sissy boy! Oh, and not just me, you'll serve all your superiors, wimp. That pretty much means everyone, haha. Oh, my friends are coming over and your gonna be a pathetic lowly sissy for us! Now let's practice your curtsy.

    Duration: 4 min | Price: $5.99

    Starring: Skyla Novea Tip Skyla Novea Directly

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  • Remember To Curtsy. Mean Girl and the Dweeb (season 2 episode 4)

    Remember To Curtsy. Mean Girl and the Dweeb (season 2 episode 4)

    The more of a walking joke we make you, the more you'll come around to being the sissy you need to be. Come to think of it… why didn't you curtesy to me when you entered the kitchen. I specifically remember us agreeing with your bully that you should always curtsy when greeting a superior. We made you practice it 5 Fucking times at the store to show him your appreciation for the suggestion. So don't think you're just gonna brush that off. Let me see it, curtsy for me and thank me for being your superior and for the opportunity to make my breakfast. That was almost cute, dweeb. Ya know what would be even cuter? If you let me do your makeup before school, haha. Awe, I know your just supposed to wear your bra and panties under you clothes to school but I think you could use just a little hint of foundation… maybe a Step-Little Bronzer. Don't worry nobody will even be able to tell. I mean the whole school had already seen the Facebook posts of you prancing around in pink panties and being humiliated at the mall but I guess you could try and act normal at school. Now get started on breakfast and get changed into the matching bra and panty set Step-Mom has laid out for you today.

    Duration: 6 min | Price: $6.99

    Starring: Skyla Novea Tip Skyla Novea Directly

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  • Cruelty Makes Me Cum. Mean Girl and the Dweeb (season 2 episode 12)

    Cruelty Makes Me Cum. Mean Girl and the Dweeb (season 2 episode 12)

    Hey babe, so yea I sent you the video. The sissy perv saw my panties and well… we both know what that means right, haha. Yup he's on his way over with some shiny pink lipstick to lube up your Cock! Well, hey, a pledge is a pledge. The dweeb saw my panties and I made him recite the sissy pledge, word for word so, ya… he's on his way over right now to get face fucked, haha. Why am I moaning??? Well, I'm touching myself cuz it gets me so wet when I think about how you bully him. Please, please can you tell me the stuff you've been doing to him lately??? I mean I want the dirtiest, most humiliating stuff you've done to him! Don't fuckin skip anything… I wanna hear about his sissy maid duties and stuff. Like, what's some of the mean stuff you make him do, babe? I'm so hot I'm almost gonna cum just hearing it all again. Ohh, tell me how you got the wicked idea to make him walk all the way home with your cum in his mouth. Like, did you know how mortified he was gonna be when I saw that? Did you know I was gonna have to play with my pussy when I heard about it, cuz it's so Fucking mean? Yea, well it worked cuz I sent the fag right back over there for more cruelty and I am definitely playing with my pussy. Are you gonna fuck his sissy fag mouth when he gets there, babe? Ohh yes, your gonna use his pretty pink lipstick as lube for your superior cock??? Are you gonna make the fag thank his Step-Daddy? Are you gonna keep the sissy's balls nice and blue while you spray thick ropes of superior cum all over those cum catching lashes? That's so hot. Oohhh yes… make him beg for your cum, Consume your cum, wear your cum… Oh yes I'm cuming… cuming, ohhh Fuck! Oh fuck, ohhhh fuck yes. Ooh that was sooo good. Your such a Fucking man, babe. That was such a good orgasm, oh fuck! Ahhhhh, oh can you send me a video of it later… I mean only if you make him cry like a fag cuz I obviously love that. Ok babe, enjoy, bye.

    Duration: 11 min | Price: $11.99

    Starring: Skyla Novea Tip Skyla Novea Directly

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  • Blackmail Fuckover. The Full Fuckover (season 1 episode 6)

    Blackmail Fuckover. The Full Fuckover (season 1 episode 6)

    I know how much you'd love me to use your hard cock and blue balls against you. Otherwise, why would you have even come into the club where I was feature dancing and ask me for the "Full Fuckover Special"? I've already started recording you and you're gonna start stroking your cock for me, haha. And I'm gonna take full advantage of how stupid you get when your cock is hard for me. I'm gonna get you to beg for the most fucked up stuff to happen to you… And I'm gonna show this video to everybody! I'm gonna make you the biggest laughingstock on the Internet. And your gonna thank me for it! Ooh, looks like that made you start stroking even faster, haha. You like that I'm doing this to you huh? You realize you're totally disposable to me, right? I'm using this video to show my friends that I can chew you up and spit you out, right? Haha! Whoa, slow it down there… You’re not allowed to cum… We haven't even gotten started yet!

    Duration: 7 min | Price: $8.99

    Starring: Adriana Chechik Tip Adriana Chechik Directly

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  • Primp And Pimp. The Full Fuckover (season 1 episode 5)

    Primp And Pimp. The Full Fuckover (season 1 episode 5)

    First, I'm gonna apply some lubricating lipstick on your whore mouth… Then I'm gonna put a little mascara on you. I'll even give you some sexy lingerie to wear… Stocking and heels too! I'll top it all off with a pretty pink bow in your hair and let the guys part your painted lips with their thick veiny cocks! I'm gonna sit in the corner and play with myself while they Encouraged you to your knees, haha.

    Duration: 13 min | Price: $13.99

    Starring: Adriana Chechik Tip Adriana Chechik Directly

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  • Public Humiliation Fuckover. The Full Fuckover (season 1 episode 7)

    Public Humiliation Fuckover. The Full Fuckover (season 1 episode 7)

    (Phone call of doom) Ya so I'm looking to win a bunch of awards again this year. Vegas is gonna be a blast! Who are you goin with? I'm sure you're gonna win your awards, girl. All I know is I'm gonna be running around running around like crazy. That convention is, like, non stop for me. My feet get so tired. It's a good thing I can get losers to rub my feet by snapping my fingers. Oh and I'm making that wimp that asked me for the "Full Fuckover Special" to show up too. Yea, the one I made beg to be my sissy cuckold on that video. I wish I had more time to abuse the bitch, my pussy gets wet when I'm fuckin' someone over like that. Gimme some ideas while I masturbate, I wanna think of stuff I can do to show off my power at the convention… … keep laughing… I’m cuming… keep going, fuck… let’s fuck that slut up! Mmmm, yes…. yesss, ohh, mmmm I’m cuming… I'm the best, mmmm, I’m the best, ahhh, I’m the best! Ahhh, fuck mmmmm…

    Duration: 6 min | Price: $6.99

    Starring: Adriana Chechik Tip Adriana Chechik Directly

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  • Becoming the Punchline. So you Wanna Serve – Season 1 Episode 4

    Becoming the Punchline. So you Wanna Serve – Season 1 Episode 4

    Stroke your cock and repeat admit what you truly desire… I wanna be Collared 24/7. Oh yes goddess raven, I wanna be the punchline of jokes amongst all your hot friends… I wanna wear a ridiculous collar. I wanna wear a pink locking collar. Once I accept you as a devoted servant… You will curtsy and be used and humiliated in front of all my hot friends and your home life will consist of daily edging rituals and failed orgasms to my picture. I’ll give you detailed instructions on how and where to place my picture and post daily humiliation affirmations all around your apartment. Goddess Raven Bay

    Duration: 8 min | Price: $8.99

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