Tag: crossdresser


Humiliation POV Goddess Dylan: You Live For Your Secret Sissy Time


Goddess Dylan

I know you have your special sissy time. Every night after a long day at work, you come home to your little secret where you dress up. You love this time, you look forward to it all day. No one knows, no one could imagine the wardrobe you have, the makeup you put on, or the slutty high heels you walk around in. And then once you’re dressed up all slutty, you search the internet for things to jerk off to. Sometimes it’s videos of hot girls humiliating you and sometimes you search for guys who want to get off with crossdressing sissy bimbos like you.
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Humiliation POV Miss Raquel Roper: You’ve Always Craved To Be A Feminized Crossdresser


Miss Raquel Roper

There is something within you that has been in your mind for as long as you can remember. But you never really understood it, did you? You know exactly what I’m talking about. Instead of being dressed like a man, here you are in pretty little panties, stockings, heels, a long wig and some make up. Before you knew the proper terminology for your identification, you were just a confused boy, weren’t you? I know you would sneak in your mom or your sister’s closet and steal her clothes and put on her makeup long before you even knew what you were doing.
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Mistress – T – Fetish Fuckery: Gangbang For Xdressed Fag Boy


Taboo Family Fantasy: Mom/Son.

Twisted, hard core "Bi Encouragement".

Custom vid. I’m excited to tell you about our upcoming night out dancing. I’ve decided to dress you up like a sexy lady, slutty dress, panties, stockings, wig, make-up. You will be so passable that men in the bar will treat you like a lady. They’ll flirt with you, buy you drinks & dance with you. You’ll make them really excited but when they figure out you have a penis instead of a vagina they’ll get very rough with you. They don’t treat faggots they way they treat ladies. They’ll drag you into the washroom & have their way with you. Many of them. All running a train on your ass & mouth. They’ll gang-bang you hard…but I know you well enough to know that you’ll actually like it…
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Humiliation POV Princess Alix Lynx: Marry Your Hand Sissy Bride, But The Ring You Wear Will Be Around Your Cock


Princess Alix Lynx

Oh look, it’s my adorable little sissy boy, and I’m wearing your favorite dress, the one with all the cleavage. It’s the least I could do after turning down your marriage proposal. But I can’t believe you honestly expected me to say yes to you. Seriously? I need a real men and well, you’re girly.
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Humiliation POV Alix Lynx: Be My Sissy Maid Of Honor


Porn Star Alix Lynx is so girly and she will make you feel so girly as she turns you from her boyfriend into her sissy maid of honor!

Hey there honey, well I guess you aren’t my honey any more, are you? You see the reason that I cheated on you is you’re simply not man enough for me. I could never be with a man like you. I need a real man and I hate to break this to you, but I’m getting married! To the guy I cheated on you with. Why don’t you let that sink in? Awww poor baby. LOL I’m not sorry, it’s your own fault, you simply were not man enough for me.

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Mistress Nikita/Obeynikita: Spanking The Maidboi




Every slut should learn the proper way to care for my hosiery and there’s really only one way to make sure they pay attention… a good old fashion over the knee spanking when they don’t do it right.
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Humiliation POV Princess Ellie: Feminizing You For The Ball


Princess Ellie

So this event that I’ve wanted to take you to, I didn’t realize it was women only. So I picked out this pretty dress for you. But the dress alone won’t do it. You’re going to need a complete makeover. And I know how badly you want to come with me so go on, take off your suit, and just try this dress on for me. I’ve got everything prepared for you, everything to transform you into a girl. Come on, don’t you wanna make my night?
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Humiliation POV Goddess Kyaa: Edge Your Sissy Stick In Your Panties While I Torture Your Sissy Nipples


Goddess Kyaa

Hey there you little sissy bitch, I want to torture those sissy nipples. I know you’re horny and you want to rub yourself in those sissy panties. Well the only way I’m going to let you, is if you agree to torture your sissy nipples. I’ll even tease you with my cleavage to make the experience more enjoyable but you’re going to have to follow my instructions carefully and torture your sensitive sissy nipples.
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Humiliation POV Goddess Dylan: If You Can’t Walk In Heels, You Can’t Call Yourself A Sissy


Goddess Dylan

Most of you are foreign to walking in heels like a girl because you’re a clunky guy. You don’t know how to be dainty like a girl and how to sway your hips and walk sexy in a pair of heels. But luckily for you, you have me, Goddess Dylan, the most feminine Goddess of all, to show you how to walk in heels, sissy. You don’t want to walk like a man but you also don’t want to walk like some wobbly bambi who doesn’t know how to walk in heels. You don’t want to break your ankles and look like a fool now do you?

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Goddess Harley – Taped Up and Pimped Out


When I saw you at the bar I know I could get you back here and Duct Tape you to that chair. You’ll notice that your wearing sexy lingerie, LOL! I have a little agreement with the guys that live here. I provide real life faggot sex dolls for them to abuse. I think it hilarious that guys at that bar think they can get with me. Just make sure you open up your asshole real wide for then cuz I get paid more if you satisfy more guys.
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Mistress Nikita/Obeynikita: Barbi, Fuck My Heels




Barbi is such a slut for shoes, especially my 6 inch stiletto heels. I like to have them licked before I go to bed each night. This time I decide to allow my bimbo sissy sex doll some release since she’s been such a good gurl. I unlock my cock and let the bitch fuck my nylons and heels until she cums all over them. As you might have already guessed, she has to lick up every last drop and suck her cum out of my sheer black stockings.
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Humiliation POV Goddess Valora: Goddess Valora’s Degrading Sissy Test (October 22nd 2017)


So you think you have what it takes to be a sissy, do you even know what that entails? It’s a lot more than what you probably think. So I’m going to put you through a sissy test to see if you truly are a sissy. For this test you’re going to need a plate. I want you to pause the video and jerk off onto a plate. And then come back to see if you pass the test, lol.
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Humiliation POV Princess Kaelin:Confused, Broken Little Clitty Sissies Have To Finger Their Man Pussies


Princess Kaelin

Hello my little sissy bitch, I know how much you long to please me. I know that deep down in that little sissy heart of yours you desperately want to make me happy. And all you have to do to make me happy is to be the sluttiest little sissy you can be. LOL! Do you think you can do that for me?

I know that you rub that sissy clitty all the time. You’ve accepted that little thing will never be a cock. You were just born with a little clitty. There may have been a time when you were disillusioned and thought you were a man, but now you’re completely broken for me. You’ve accepted your life of being humiliated by me, because you know a little sissy bitch like you would never have a chance with someone like me. And therefore you may as well not be a man at all.

Now I want you to start fingering that man pussy for me. Little sissies have to finger their man pussies. You need anal stimulation along with rubbing your clitty in order to get off. Because that is the only way a little sissy slut like you should ever get off. So rub your little clitty like a good girl, I know what a horny little slut you are. Show me how desperate you are to cum. I want to hear you moaning like the bitch that you are as you are, all dressed up like a slut getting off to femdom internet porn! LOL! How pathetic are you?

Now bend over and spread your man pussy and put a finger inside. Fuck that man pussy, show me what a good little whore you are. The thing that sucks about being a sissy is that you’re not good enough to be a man or a woman. You’re just a pathetic confused fuck. All you have is me, humiliating you. You know that me making you fuck your little man pussy is the best you’re going to get. So you should fucking thank me.

Start fucking that man pussy deeper and harder slut. Show me what a good girl you are for me. Now rub that clitty while you fuck that man pussy. Put another finger in, really stretch yourself out. You like that don’t you? Of course you do because deep down you truly are a little sissy bitch. You Need it in the ass. You need me to help you fulfill your sick, perverted desires. Fuck it harder, hit your prostate. Your little clitty is so hard because you love it in the ass. You love fucking your man pussy you little slut. Now add a third finger. You’re a pathetic little sissy bitch, fucking your ass, rubbing your clitty, it’s so humiliating but you love it. And it’s what you deserve. I’m going to help that little clitty squirt. Get right to the edge, whore, as I bring you to an explosive orgasm.
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Humiliation POV Kelle Martina: Little Panty Boner Boy


Kelle Martina

Oh look, it’s a little panty boner boy. You love wearing panties, don’t you? But most of all you love seeing girls in their cute panties while you wear yours and touch yourself. Looking at me in my panties makes your panty boner all stiff. I’m wearing a little, black cotton thong, what kind of panties are you wearing? How did you get like this little sissy boy? How did it start? Your little panty obsession.

I’ll bet you’d love to sniff my panties while you rub yourself in your own little panties. I like you wearing girly panties, that way it shows exactly what kind of little sissy you are. You are a little sissy boner boy! LOL! You only wear panties any more under you boy clothes. And every day you rub your little boner in your panties. So rub that boner in your little sissy panties. Rub it little boner boy as I tease you in my panties.

I know you want to wear my panties, you little panty freak. That thought gets you so excited, doesn’t it you little panty boner boy? Right now you’re rubbing yourself just like a girl through your little panties. And that’s exactly what I want. Rub yourself for me little panty boner boy! LOL! Rub it and stare at my ass. I’m going to make you cum right in those panties. Nothing else excites you more. It feels good to have a pair of nice, soft, girly panties against your cock. You hate boy underwear, they’re so ugly and uncomfortable. Panties are pretty and soft and make you feel like a little sissy panty boner boy. And that’s what you want. You want to be a good little panty boner boy for me.

Now I want you to rub yourself faster and say, “I’m a little panty boner boy”. LOL! Say it over and over as you rub that dick in your panties. I want you to say it until you cum and stain those girly sissy panties. I want to make sure you don’t forget what you are! Cum in your panties you little panty boner boy!
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Humiliation POV Goddess Sahrye: Sissy Damsel In Distress Self Bondage



Goddess Sahrye

So I hear that I’m the bondage queen of your dreams. That’s right, in case you didn’t know, I’ve done many bondage scenes. With real men of course. But you don’t want to see me in bondage, you want to be just like me, don’t you? You want to be a bondage princess. So I’m going to teach you all of the self bondage techniques that I know. Do you have all of the items you need to be a damsel in distress? LOL! Do you have your high heels and your pantyhose? Do you have your gags? All the fundamentals of a bondage girl. Because you know boys don’t get tied up in bondage, only girls. And that’s what you are, isn’t that right?

So in order to play the role, you have to look the part. Rule number one of a bondage queen is that her heels never ever come off. So I’m going to teach you how to lock your heels on. Good girl. Next I’m going to teach you how to tie up your legs, we have to make sure you can’t run away. Doesn’t that feel good? You love the sensation of being bound. You’re a pretty girl with your legs all taped up. But you’re not a real damsel if your hands are free. So I’m going to show you how to put your handcuffs on and make sure your arms are secured tightly behind your back.

Doesn’t it feel good to be my little bondage princess. Now that your hands are behind your back and your legs are nice and secure and your heels aren’t going anywhere in your tight little mini skirt with those pink panties peeking through, I want to see you struggle.

You know what comes next don’t you? Take those cuffed hands behind your back (I’ll show you how), grab a pair of panties and shove them in your mouth. Gag yourself sissy. Good girl. Now I don’t want you to spit that out so we’re going to make sure it’s nice and secure with a ball gag. How do those panties taste? Well aren’t you the perfect damsel princess? Look at you, you’re a faggot little sissy loser who’s trying to impress me by being in bondage for me, the internet’s most popular bondage queen. You must feel so pathetic. You’re my bitch. I’m going to leave you here just like this, gagged and bound. Struggling and drooling in your high heels and your pantyhose and your sissy girl clothes. I’ll bet you’d love it if I took pictures and posted it all over my social media accounts.
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Mistress Nikita/Obeynikita: Candi Cums – WMV


fuck hole cum-dumps… I mean really (not just on video!).

I make Candi suck my Barbi doll for a while and then I strap up to fuck Candi’s ass-pussy so she’s got a cock in both holes. Once I’ve had enough, I instruct Barbi to milk Candi from behind while I finger her gaping sex pot. The slut gets so hot and bothered she can’t control herself — she sprays her warm load all over Barbi’s bedspread without permission! Barbi is such a cum whore now she immediately coats her fingers in Candi’s cum so she can suck it off. Then I feed the slut a little more sissy goop with the same gloved finger I stuffed up Candi’s fuck hole.
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Humiliation POV: Dumb Braindead Airheaded Sissy Bimbo Brainwashing


This is a 40 minute long, intense brainwashing clip that takes you on a journey so deep, you will never return. There is no way to reverse this as it has been designed to effect you permanently. So don’t resist as resisting will only make the effects stronger. You are trapped in this reality and your mind is completely empty making it easy for my words to penetrate your subconscious. Good girls like to listen and obey.

Men love silly bimbos. Intelligence is not attractive to real men. Real guys love braindead bimbos who are too stupid to think twice before dropping to their knees and getting their pretty faces fucked by big hard cocks. Being dumb is fun. Good girls giggle every time they have a sissy thought, giggling is so arousing. Every time you giggle you become more of a mindless airheaded bimbo. Remember the dumber you are the more guys will want to fuck you. Where most people have a functioning brain in their heads, all you have is a big ball of fluffy pink cotton candy. Cotton candy cannot think so there is no reason for you to try to use your pink cotton candy brain to think. Good girls want to shut of their minds completely and be overtaken by my words and thoughts of giggling and dressing sexy and sucking big cocks. Good girls love to be stupid and mindless. All you want to do is giggle and suck big hard cocks and eat as much cum as you can. Every drop of cum you swallow makes you a tiny bit dumber. So you can imagine how you will feel after sucking a dozen cocks and swallowing all of their loads. Your mind is empty other than giggling and sucking cocks in your sluttiest outfits. You are a slut and sluts are dumb. You are cock dumb. You want to be a brainless bimbo whore. You want to be a faggot feminine fuck toy for men to play with. This is all being implanted in your subconscious and there is nothing you can do about it and it will never go away. Even if your conscious mind starts to forget the seeds have been planted to so deep into your subconscious that they can never be removed. You are a brainwashed sissified bimbo. (This small description barely does justice to what you will hear and feel when you watch and listen.)
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Humiliation POV Kelle Martina: Mind Melting Sissy Re-Education (Effects)


Kelle Martina

What you need is to be completely re-educated. I know that deep down inside, you’re a sissy. A sissy is a man who’s been reduced to a feminine place. Chastised, dressed up, completely erased of any maleness. But remaining male, remaining humiliated in that state, not fully transitioning over. And what I want from you, is for you to go deeper. Listen to my voice, relax your mind, let yourself be completely taken over by feminine energy. Listen and focus on the pretty sissy bow on my bra.

Focus little sissy, don’t look away as I sway back and forth. Your mind completely melting away, becoming my good little sissy. Know that your maleness is repulsive to me, I want you pretty, I want you feminine. Now think about your male clothing, they’re so boring, and the fabrics are so rough. They’re not silky and lacy. Now I want you to think of your dream sissy closet. All the soft fabrics, the pretty colors, the panties, the stockings, short tight skirts, high heels. So pretty, just imagine all the beautiful sissy clothes that feel so good against your body. You’re displeased with your body right now, it’s not feminine. You want the sexy curves of a female. You want all of those things, the pretty clothes, the curvy body, all atop those sexy high heels.

You want to be sex on legs in the highest heels you can walk in, swaying your hips back and forth. You want that with every fiber of your being. You can feel it in between your legs when you touch it. You want to be fucked and penetrated and used like the slutty sissy that you are. You want to please a man properly. You want to please, you want to be a submissive, beautiful female. You want to toss out your ugly male wardrobe and begin building your new beautiful sissy wardrobe filled with sexy clothes. I’m going to turn you from a good boy to a good sissy. You wanna go all the way. You want to completely transform into the sexy sissy of your dreams. You can feel your mind changing, imagining this life that you can create. I’m giving you the sissy life that you want, that you deserve. You can do it, you will do it, for me.
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Humiliation POV Princess Lacey:Leave Your House Sissy, Leave Your Old Self Behind


Princess Lacey

Well sissy, this has been going on for far too long, and you know exactly what I’m talking about. You get all dressed up like a slutty sissy, for what? To sit around your apartment all by yourself? Not anymore. I’m going to put an end to that. I know you’re dressed up right now as you’re watching this because you truly are a sissy. So it’s time to be your true self, out in the real world. I want you out there strutting around like a sissy all over town. I want you exposed to everyone.

You are going to do exactly as I say, you are my sissy after all. So I want you to put on your sexiest, most feminine outfit. I want you dressed from head to toe, from your heels to your wig, makeup, stockings, panties, a short mini skirt, you know the look you just love. Get really slutty and girly for me.

Now that you’re looking like my pretty sissy, I want you to go stand in front of the mirror and take a good look at yourself. That’s who you are. Just look at yourself, there’s no denying it. Now I want you to say, “I am a pretty sissy and I’m ready to let the world know exactly who I am.” Take that in.

Get ready, you’re going to leave your house and leave your old self behind. When you open that door and step outside dressed like a sissy, you will feel so liberated. And you will thank me for this. You’ve been sitting alone, dressed up for years now. Those days are over. I want you out there. I want this done today. I know you feel ashamed, but don’t. Don’t give a fuck what anyone else thinks, just be who you are. It will be such a relief. It’s a different world now, you don’t need to be ashamed anymore. You need this so badly. This is who you really are. And while you’re out I want you to go shopping for something sexy dressed as your sissy self, your real self. And when you come home, you’ll be on your knees thanking me, after your first experience out in the world. Fucking liberate yourself, expose yourself to the whole fucking world.
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