All femdom clips tagged with "crossdresser"

181296 - I punish my sissy slut on the cross

I punish my sissy slut tied to the cross…i whip his balls and his tiny dick and this slut begs for more…i stretch his balls, whip them hard again, his tiny dick wets like a slut and his little nuts end quite red.

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163000 - Education to be a Sissy Rubber Bitch

It is a damned hard road to be properly educated to a true rubber bitch. Especially by Lady Satori and especially if the educational object still have balls and a dick. The need to suffer first before the off of Rubber Transformation can be gone understood. The ultimate degradation in red and pink rubber to ridiculous to be made cock made of course is inevitable!

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27351 - Mistresses Make a Sissy Slut Out Of Their Slave - Crossdressing Femdom First Time

Gorgeous sexy Mistresses Kira and Sofi in latex and high heels wanted to feminize their male slave by turning him into a sissy blonde bitch. First of all, the dominant girls ordered the slave to put on a black dress, then Mistress Kira ordered him to kneel - and put a blonde wig on him. Then came the turn to wear black stockings. After the submissive guy put on everything that the Mistress ordered him, he became almost a girl, but there were still some details missing. Sofi and Kira sat their sissy slut on the sofa, and they themselves sat on the sides and, taking cosmetics in hand, began to apply makeup on the slave's face. Latex Mistresses constantly taunt their bitch and slap him. When the male slave is already fully feminized into a blonde bitch, the Mistresses ordered him to start dancing in front of them like a bitch while they smoke cigarettes and taunt him. The Mistresses then ordered the sissy slut to get on all fours for a spanking.

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117379 - Ride on Goddess' Cock

After my pussy was properly licked and worshiped by my sissy slut, I needed to fuck her ass with my strap-on. Fucking my slut's ass made my pussy so wet, I needed her to lick me up some more. Goddess cums and cums and cums!

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117380 - Worship My Cummy Pussy

After dressing up my sexy tranny slut and having her clean up my kitchen after dinner, I told my sissy slut to lick clean and worship my cummy pussy. Enjoy watching as I cum in my slutty crossdressing slut's mouth and get much pleasure.

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11300 - BECOME MY CHATURBATE SISSY SLUT

I want the world to see and hear that you're my slut so I'm going to dress you up in lingerie to prepare you for your cam session on Chaturbate. Sluts need to be stuffed, so make sure you have a dildo and butt plug ready to go! I'm going to instruct you how to play with yourself and all the things you should do to please your male clientele. You'll end your show with a nice, creamy self-facial!!

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11292 - CUM EATING PERVERT'S PANTY PARADE

Could it be you're parading around in panties right now watching porno, ready to fap? You just dig the way your bulge look in those undies. You feel so naughty being a panty freak! Why don't you moan for me so you can show the whole world how much fun you're having! Isn't it hot that others might discover the secret of a sexual deviant? Cum for me, panty freak! Masturbate like a girl until you cream in those panties. Then clean up with that perv tongue of yours!

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10882 - TURNING YOU INTO MY MONEY MAKING SISSY WHORE

I'm not going to try sex with you after that last pitiful performance you gave me. Instead, I'm going to put you to work! This is how you can make it up to me. I'm going to dress you in women's clothing and you out!

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10681 - PREMATURE EJACULATION TO CLEAVAGE FOR A SISSY CROSSDRESSER

Once again I catch you in my room wearing more of my clothing. You certainly do prefer to dress up like this instead of going out and actually finding a GIRL. You'd rather cum in your panties instead of trying to make love to me. Though the sight of my ass in jeans and my cleavage in a low cut top makes it hard to hold back creaming yourself. I bet if I fucked a guy in the next room over with you listening you'd cum in your lady panties almost instantly. Oh, how I'd love to titty fuck you with my strapon, as I bet YOU'D be the one blowing your load all over! Guess what sissy, time to cum! I bet you'll cum without even touching when I show my big tits kept snug in my pink tank top...

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10571 - GIRLFRIEND FINDS YOUR SISSY PORN & IS TURNED ON TOO

I want to talk to you about what I found on your computer... Sissy porn? I'm not mad, I'm just worried you're gay and won't want to be with me anymore. That's not the case though, is it? Let's act out one of those videos. I want to play a part in your fantasies from now on. I mean, this is really starting to turn me on seeing you all dolled up... Could it be this is BOTH our fantasies?

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10418 - MY NEW SISSY FAGGOT

We have to talk about what happened in the bedroom just now. Your performance was terrible! Were you thinking of another woman? No? You were certainly staring at my lingerie... Why? Are you some kind of sissy or something? Confess to me. You're getting beet red right now! Does this mean you aren't into women? A little bit? You're more interested in wearing their clothes, aren't you? I think you want to do something else for me, don't you sissy faggot? You want to suck a big meaty cock, huh? How about we dress you up in women's clothing and I call my guy friends over for you to blow? Gangbang? I won't let you cum though, as I believe sissy fags don't deserve to cum, only to please their masters!

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9745 - SISSY SLUT FACTORY

SISSY SLUT FACTORY 1080PPlay Video Pimptress Olivia and I have captured another innocent man and turned him sissy inside our very own sissy factory! SHE is now going to be pimped out so we can make lots of money! We decide on the name Britney before we apply her makeup. We make her practice her moaning so our clients will think she's enjoying this! The clip ends with Britney's priceless reaction to the client whipping out his cock.

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9729 - FORCED TO BE MY BIMBO DOLL

After one full year of chastity, you're pretty desperate to be unlocked so you can play with your dick. How badly you must be aching to cum, hm? Well in order to earn your release you must do something for ME. I want you to be my bimbo doll. Of course you agree, and I begin to show you your wardrobe, describing in detail how each item will feel when it's on your body. The high heels and corset in particular will be uncomfortable, my bimbo-to-be! Just for giggles, I add pegs to your nipples, underneath your bra. I begin applying makeup to your face and fill you in on our day of public humiliation plans. Now it's time for you to cum! I tease you with my body and count you down--except last second I DENY you. Instead of allowing you to cum, I decide I want to extend your chastity.

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9677 - MEET REGINA

Mandy and I try to teach Ray a thing or two about sucking cock. Frankly, he sucks at sucking cock. Perhaps a makeover will do the trick? We dress him in a pink lace panties and bra set, a red dress, and whore-ish stockings. We complete the look with high heels and a wig. We try again, and Ray--er uh, REGINA is much better. Perhaps "she" needed to FEEL the part as well? We take turns pounding "her" throat, making "her" gag on our cocks! We even put "her" to the test of sucking both of ours at the same time!! Regina succeeds with no problem! "She" even asks to suck YOUR cock next! What a sissy WHORE Regina is! Would you let "her" suck you? Gross. Probably not, huh? LOL

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8926 - Sissy Slut Training #02

My pathetic fat slave keeps going on about how much he'd like to be a woman so I took pity on him and decided to give him another sissy slut training session:She's sitting on the floor in front of me wearing a pair of skinny jeans, high heel boots, corset, silicone breastforms and a wig. Knowing how much she adores my perfect size 7 feet I let her kiss my boots and lick my spit off them. Then I put some red lipstick on her, after all, sissies DO need makeup! I let her kiss my boots some more and apply nail polish to her nails to make her look a bit more feminine. Doesn't she look cute? Hahahaha. I briefly leave the room and return wearing a strap-on with a very realistic latex dildo, time to see how much of a slut she really is. I take a seat and let her blow me, her lipstick smearing all over the strap-on... I occasionally spit on the fake penis and into her mouth to make sure she has an extra incentive to keep sucking my dick. As always, while greedy at first she soon starts to gag on the dildo which is simply unacceptable and calls for punishment...I gag her with my dirty socks and give her a few good slaps before making her get up and pulling down her pants. I don't think her pantyhose will provide much protection from my whip... Indeed, she immediately starts moaning and moving around! Alternating between whipping her ass and kicking it with my boots she will now pay the price for not doing a better job getting me off!

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8920 - Fucking My Sissy Bitch!

My pathetic slave always begs me to let him have my old makeup so he can play dress-up at home, he just loves being a sissy! Well, since a sissy should be able to handle cock I am giving her another lesson in taking it into her mouth and ass!She enters the room wearing skinny jeans and a corset that’s about 10 sizes too small, her fat gut spilling out everywhere... Can sissies get pregnant? She sure looks like it, bwahaha! To make her look even more ridiculous she has to wear an open-mouth gag that looks like a pair of red lips, it’s so hard not to bust out in laughter! Come on girl, get on your knees and show me those lips! Let me fuck your face with my strap-on… But try not to choke again! Ugh, she’s just terrible at this!Fine, let’s forget about the blow-job before she pukes all over the place. Time to work on her ass, maybe she’ll handle that better… I handcuff her and pull her pants down, aww, that little sissy-dick is all shriveled up, maybe she doesn’t like cock after all? Not my problem… I warm her ass up with my wooden paddle. Right from the start she starts to breathe heavily, let’s gag this bitch with a ball-gag before she makes too much noise.I make her get on her knees and spread her legs. Time to take it up the ass! Ugh, how am I supposed to penetrate her with her boots and jeans in the way? I need her to spread her legs further! Next time she better be wearing a skirt! I remove her boots and jeans, I am determined to fuck her good and nothing is gonna stop me tonight! Yes bitch, take it, let me fuck you like the whore you are! Holding her by her corset I am fucking her doggy style! At least she seems to be better at taking at in her ass than her mouth but all that moaning annoyed me so I punish her with a few more strokes from my rubber flogger and paddle. We’ll make a good slut out of her yet!

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8974 - Fun with my Sissy Slut

I really went all out to turn my slave into a sissy slut! I made him dress up in a red corset, stockings, high-heel boots, a wig and even applied makeup and fake fingernails. Doesn't she look lovely? But what good is a sissy who can't satisfy a man? Time for some sissy slut training!I am sitting on my bed and playing with my very realistic looking strap-on dildo when I order her to come over… I let her give me a good handjob and then show her how to suck my dick, take it deeper into your greedy little mouth!Next we need to practice taking it up the ass. Bend over my little bitch and let me fuck you! Do you like it? The way you’re moaning it would certainly appear so, hahaha. Once I’m out of breath I lay down on my bed again and make my little bitch massage and suck my dick some more.

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7353 - SISSY FOR ELLIE

I'm looking rather sexy in my shiny skirt and top. I'm wearing an itty bitty black thong to cover my pussy. On my legs I have black sheer stockings with black pumps. You're instantly turned on. Though the truth is, instead of fucking me, you'd rather be wearing my outfit! I have some sissy assignments for you in this clip. I will be telling you how to live as a sissy for Ellie.

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