Tag: crossdresser


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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Humiliation POV Kelle Martina: Be A Sissy Hooker In Public On Halloween


Kelle Martina

You’re a sissy but you can’t go out dressed like a woman every day. Aren’t you lucky that one day a year, people get to dress up as whatever they want. And everyone thinks it’s just a fun costume. You’ve probably never worn any of your girly clothes outside the house before, right? Well what better opportunity than Halloween. On Halloween you can be anything or anyone, including a hooker, LOL! That’s right, you’re not just going to be a sissy, you’re going to be a sissy hooker.

I want you to get dressed up soooo slutty. I’m talking slutty high heels, stockings, a Short mini skirt, a wig, makeup. You should look like a street walking hooker, lol. I want you to be as trampy as you can get away with publicly. Lots of women like to express their more sexual side on Halloween so you should be able to be just as much of a slut. I want you to make sure you have plenty of time to make yourself look perfect before you walk out that door. I know the thought is exciting you. It’s something you’ve always wanted to do. And it’s totally socially acceptable to do.

And no one will know that deep down inside you really are that slutty sissy. We both know that you are that slutty sissy all of the time but you just can’t show it except for one day of the year. Isn’t it going to be so much fun to dress up and go out in public? I’ll bet you’re so excited to show off your sluttiest outfit and your highest heels! LOL! I want you to impress me, I don’t want you to look like a man in a dress, I want men to have to do a double take when they look at you! I want men lusting after you, LOL!

This is going to be your sissy debut! Aren’t you excited? Maybe you’ll even get lucky and some drunk guy will think you’re a girl and he’ll let you suck his cock, LOL! Or maybe he’ll know and he just won’t care because you look so fucking slutty and hot! You’re going to have so much fun being the sluttiest sissy hooker on the street.
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Mistress – T: Turning Hubby Into A Sissy (Part 1-2)



I manipulate my devoted husband into dressing up in women’s clothing to amuse me…I tell him that it will turn me on because I’ve started to like women & I’ve been having a lesbian affair…but then I drop the bomb: that I’ll be pimping him out…

…after convincing my husband to cross dress for me I get out my strap-on & start training him to be a sissy slut. I’ll be pimping him out so he needs to learn to suck cock & take it in the ass like a champ.

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Humiliation POV Goddess Isabel: You Want To Be Perfect And Girly, Just Like Me


Goddess Isabel

While this clip is not a traditional mesmerize clip, it has hyp n0 t!c undertones, it is set to trance like music, and is constructed to brainwash you.

I want to show you how weak and pathetic you are. You have a lot of secrets but this one is a special secret. Im so perfect, and I look like a woman, because I am. You look like a man, but inside you are a girl. You love shiny leggings, nail polish, lipstick, panties, and all of this girly stuff. Dont think. Im here to turn you into my perfect girlfriend. Yes because I want a girlfriend and you can be my perfect girlfriend. Dont you want that too? Of course you do. You will love it.

Look at how perfect and girly I am, you want to be perfect and girly too. You want to be me. Look at my nails, look at my high heels, you want to look like this. I am your Goddess and you love to be like me. I know exactly what you need. I will transform you. From your skin, to your clothes, to your makeup, I will give you a complete makeover and make you so girly, just like me.

Look at how sexy and girly I am as I mindfuck you with my words. Its so easy to brainwash you into my perfect sissy girlfriend. You just look at me and listen to my words and it all comes so easily for you now. Youre going to look so sexy, so amazing and you will love how you feel once youve been transformed. I cant wait to see how sexy you look.

Do you see my high heels? You should also be in very slutty high heels. It will make you feel so sexy and so girly, just like me. Im destroying the man inside of you, leaving you as a desperate sissy slut, only capable of bimbo girly thoughts and dress. You will be my perfect girlfriend. I cant wait to see how you turn out. I know this is your dream and I cant wait for you to realize your dreams and reach your full potential. Worship and obey, worship and obey.
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Humiliation POV Kelle Martina: Sissy Gangbang Cum Dump Bimbo Slut


Kelle Martina

You are such a little sissy arent you? Of course you are, if you werent such a sissy you wouldnt be jerking your cock off to this video right now would you? But the problem is, you are jerking to it. But youre too much of a bitch to give in to these desires of yours to be turned into a little whore, so Im going to make sure you become the sissy slut you truly dream of being. You see because you dont just want to just dress up, you want to suck and fuck huge cocks, lots of them at the same time. You want to be a sissy gangbang whore. That is what you what isnt it? Its what you fantasize about.

So Im going to dress you up in a slutty little outfit. Im going to turn you into the hot little bimbo youve always wanted to be, whether you like it or not. Men are going to find you irresistible. You see Ive told some men about you, about what a fag you are and how much you want to suck cock and well, they cant wait to meet you. Theyre going to make your fantasy a reality. Im going to arrange a gangbang party for my little sissy bitch. Youre going to be the center of everyones attention, lol.

Imagine how youre going to feel when I parade you in to a room full of men and show you off in your slutty little outfit for the first time. Youll be nervous, scared but so excited. Especially once you see all of their huge cocks. We both know what this is what you really want. So I want you to just let go, and become the sissy whore gangbang fag of your fantasies. Just give in to it. Youre going to be so vulnerable to whoever wants to fuck you in the ass or the mouth. Youre going to be a little cum dump. Im going to make sure of it.

Theyre going to humiliate, fuck and jizz all over my sissy bitch. Imagine all those huge cocks going in and out of all your holes. And Im going to look at you right in the eyes and laugh in your face. Theyre going to treat you like a little fuck doll because thats exactly what you are. Im going to fuck your world up, and youre going to love it. And while theyre pounding you and dumping loads on you, theyre going to be calling you names. I can see how hard your little sissy clitty is your panties right now just thinking about all of this. Youre going to be a cum covered sissy slut. LOL! Youre a total sissy cum dump, thats exactly what you are. You dont get to cum until youre covered in jizz. And youll say, Thank you Mistress for turning me into the sissy cum dump Ive always wanted to be.
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Humiliation POV Princess Brianna: Only Sissy Losers And Women Wear Panties


Princess Brianna

Hey pantyboy, I know youre sitting there in your panties already watching me. You just love wearing panties. It makes your sissy dick so fucking hard. Look at these sexy pink panties I have to show you. Dont you wish you had these on? I know you love the pink ones with the hearts! LOL! You just love the way panties feel against your skin. But more importantly is that you know you belong in panties. Pathetic little sissy bitch losers with small dick dont belong in real mens underwear.

You love feeling sexy and girly. Your cock just throbs every time you put on a pair of panties. Youre not a man, youre a fucking girl. And I can prove it to you. Ill bet that you go panty shopping, dont you? I knew it. And you know that men dont go shopping for panties, dont you? Only sissy losers and women wear panties. I wonder what kind are you favorites? Do you like silk or cotton, full back or thongs? It doesnt really matter to me, you look like an idiot either way, LOL!

And do you know why else you belong in panties? Because your little tiny sissy clitty fits just perfectly in them. Its like they were made for you. A real mans cock wouldnt even begin to fit inside a pair of panties. I think its so gay that you wear panties, LOL! You love wearing them. Look how hard your little dick is right now inside of them. Youre a pantyboy. Admit it. Admit youre not a real man.

But the funniest thing of all to me is that you get turned on when I humiliate you for wearing panties. You put them on and then you jerk in them while I humiliate you. Wow, youre so fucking pathetic. Tell me how much you love wearing panties loser, confess to me.

Look how cute my panties are. Ill bet youd love to sniff them, to lick them, and then to wear them. Oh god I know that would make you so fucking hard. But that will Never happen loser! But we can play dress up and wear panties together, wouldnt you like that loser? Ill bet you wear your panties all the time, when you go out with friends, when you go to work, everywhere. You love your little secret. It keeps your little cock hard all the time.
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Subby Hubby: Daisy Ducati & Raven Bay Crossdress/Pizza Boy Gets Cuckold (Pt 4 Sissy Crossdress)


Subby Hubby: Daisy Ducati & Raven Bay Crossdress/Pizza Boy Gets Cuckold (Pt 4 Sissy Crossdress)

Goddess Raven Bay and Daisy Ducati now have the pizza boy completely cross dressed in a red sexy glitter dress and add some final touches of lipstick he is now there sissy slut they make him strut his stuff and even dance for them now he will go out and seduce men and bring the studs back to the girls, after they have had their fun with their new cuckold sissy pizza boy the ladies decide they want to fuck, so they bend him over and get ready to strap up and fuck his man pussy.
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Mistress T: Be My Sissy Crossdresser


Mistress T: Be My Sissy Crossdresser

Custom vid (no name mentioned) of me, Mistress T, talking about “the rules” of what I require from a sissy, cross dressing slave. “Recently I have opened a special social club that caters to cross dressers and the men who admire them. I will need you at the club as a sissy and be prepared to pleasure men (or women) as I see fit. You will need to wear full makeup & ladies attire. I’m sure you know what most of these men want: first and foremost a good blowjob. Do you know how to give a good blowjob? I hope so because that’s important in this role. Also we get couples who need a submissive.” I guide you in a MASTURBATION INSTRUCTION explaining your role at the club, in particular all the sissy cock sucking & cum eating you’ll be doing.
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Sissy Extreme Chastity Tease


Format: MMP4
Duration: 9 minutes
Size: 280.29 MB
Resolution: 1280×720

*** UNIQUE CHASTITY! *** Cock piercing locks to piercing behind balls, locking cock in a downward position making an erection painful & impossible. My sissy comes into the clinic to have her transformation monitored. We discuss male urges & I unveil my reasoning for piercing that is now healed. I bring out a lock & key explaining to my sissy that arousal will become so painful I will now gain complete control over all male urges. I lock his/her cock to a ring between the scrotum & anus (perineum) then sensually tease him to demonstrate how painful erections will now be. This is a very sexy tease & denial vid with extreme chastity.
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