All femdom clips tagged with "crossdressing"

32028 - SISSY IS THE ONLY WAY

(CUSTOM) Miss Deviant plays the role of a psychiatrist, helping you with your anxiety about sex. During the course of the conversation, she discovers that the reason you're anxious is because being a man is too much stress for you. Because you only have a little dick, you're unable to live up to the expectations of being a man. So to compensate, you seek solace when you wear lingerie. So Miss Deviant decides it's time for you to embrace being a sissy, making you throw out all of your male underwear and replace it with lingerie and telling you that you're only allowed to watch sissy porn from now.

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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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25961 - CUCKED FOR MISTRESS

Have you ever wondered what it would be like to be my cuck? Well, you're about to find out! I'm going to tell you how exactly I will make you my little cuckold. From making you wear panties, a chastity cage, and a butt plug, teasing you to arousal before leaving you in a hotel restaurant to stew in frustration while I go upstairs with my date for the evening. Listen to every delicious detail of my humiliating cruelty as I spell out your life as my cuckold and why I'll be getting more pleasure than you!

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25881 - Maid for the Ladies - with Special Guest Madame Catarina: Part 2

Part 2: Madame Catarina and Lady Victoria Valente take great delight in taunting and teasing the new slave struggle to put the stockings on the Ladies decide he is not feminine enough and requires something else. A rubber doll mask is soon. When the stockings are finally on Lady Victoria Valente selects a maids dress and the slave is soon the slave into it. When satisfied the maid is looking well presented in stockings and dress the Ladies decide he is not feminine enough so a rubber doll mask is fitted and then a wig to create a perfect pretty sissy maid. But the maid needs some finishing touches and is made to wear a pair of white lace gloves and then into a pair of high heels. The maid is not quite finished so Madame Catarina fits a headband and then the maid is complete and the Ladies can begin to cruelly use their new plaything…

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25879 - Maid for the Ladies - with Special Guest Madame Catarina: Part 1

As part of her vacation Madame Catarina has decided to visit her friend Lady Victoria Valente at her Stuttgart dungeon. Lady Victoria has a new cleaning slave and has invited Madame Catarina to inspect his work. Both Ladies are displeased with his work and decide that his work would improve if he were transformed into a sissy maid. Once the slave is fully transformed into a very feminine maid complete with panties, stockings, short dress, high heels, hair and mask the Ladies decide to have some cruel fun with their new plaything.Part 1: The new cleaning slave is busy at work in the dungeon when Madame Catarina and Lady Victoria Valente enter to inspect his work. Both Ladies look stunning in their respective outfits and the slave is treated immediately to a few strokes from Madame Catarina’s riding crop even before his work is inspected. Both Ladies inspect how clean the dungeon is and find dust everywhere and the slave is soon berated for his shoddy work. The ladies then decide it is time for the slave is transformation to begin and to start with he must hide his chained cock between his legs in order to wear his new cotton panties. The slave is soon fitted with a bra to match his knickers and then breasts are duly inserted. The slave is to put on a pair of black stockings much to the amusement of both Ladies. With the slave now in white cotton knickers and bra and black stockings the Ladies need to decide the next stage of the slave is transformation into a sissy maid….

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17673 - Pink Panty Sniffing

Lay down on the floor while I tease you from above with my pink lacy panties. I've been wearing them all day, and they're getting nice and juicy, and smell like my sweet milf pussy.Now I'm going to come up closer and rub my hairy bush right next to your face while sliding a bit of the panty right in my snatch before sliding them off. You can't wait to sniff them for yourself, jerk your cock with them or even slide them on yourself so you can feel them juicy from my pussy right next to your dick.Custom videos and cam shows Skype or Discord are available so email me at morganadelray@yahoo.com

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131239 - Sissy CumDumpster

I have a little sissy homework for my little sissy cocksuckers. I'm going to lead you through step by step instructions that will set you up to find some cocks to suck and fuck for me. You CRAVE to be a little sissy cocksucker for me, to be a good little sissy slut for me, and I'm going to send you down the path to turning you into a little sissy cum dumpster.

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16033 - Sissy CumDumpster

I have a little sissy homework for my little sissy cocksuckers. I'm going to lead you through step by step instructions that will set you up to find some cocks to suck and fuck for me. You CRAVE to be a little sissy cocksucker for me, to be a good little sissy slut for me, and I'm going to send you down the path to turning you into a little sissy cum dumpster.

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14980 - MHA CROSSPLAY FOR MY BI FRIEND

Ellie calls you over to her house super early in the morning to ask you if you'd like to join her this weekend at the anime convention. She's in her Toga cosplay but you didn't bring anything to wear. Luckily she has you covered! You can borrow her schoolgirl Uraraka, complete with big padded bra and silky satin panties to look like a real cosplay girl. You might be reluctant but Ellie convinces you that you'll have a blast and that guys won't be able to keep their hands off you when posing for photos. Not to mention the 18+ panels and the orgies that tend to happen late at night. Lots of con-goers are heteroflexible, if not just downright gay, so let loose! It's always wild at an anime con. The weebs know how to PARTY! Think about all the DICK you both will share in a hotel room. Your holes will be stuffed full and it'll be a wonderful time made better all because you decided to crossplay!

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14977 - SHOW OFF YOUR SLUTTY SIDE TO THE INTERNET

Today you're going to get dressed in your feminine best in order to take sexy photos and videos. Ellie is going to instruct you on poses and give you ideas for your slutty little shoot. Once done, you're going to go on every website that allows nudity to post your creative works and you must keep your DMs open! You'll get all sorts of dirty DMs sent to your inbox and once you have a collection of messages from random guys, you're going to come back to this vid and masturbate while thinking of what a huge slut you are!

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13642 - BEGINNER SISSY TASK TWO

Your journey into becoming a fruity little sissy bitch continues with this beginner task. You know you want to complete it, not just because you want to make your Mistress happy. No, it's because you want to be the little sissy ass bitch you always wanted to be. So get working hard to become the most feminine sissy out there!

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3835 - Intro to Sissydom: First Task

You’re about to embark on a beautiful new journey. And I’ll be there to guide you on your way. Let a hot brat give you your first sissy task and coach you on what to look for. This is the first step (of many!) to becoming a pretty little princess for me!

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94649 - Whore instructions - English subtitles

I will educate you little bitch to be my whore and you will play by my rules!For this video you will need a few plugs for you ass and mouth and clamps...not for tender little pussys!!

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61893 - Humiliatrix Princess Liz Tricks You into Sissy Servitude

Princess Liz puts you thru a cruel tease and denial session to weaken you into wearing panties for her. Once Liz gets you into panties? It won't be long before she can coax you into a sissy maid dress and turn you into her helpless, fully-feminized sissy servant. Think you can resist your bitchy-bratty owner?

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62453 - Cream Your Sissy Panties for Humiliatrix Miss Kendra

Miss Kendra intends on stripping you of all your masculine pretensions tonite. The first step is for you to prove to Miss Kendra that you truly are her helpless sissy weakling. You will wear the darling sissy emasculation panties Miss Kendra picked out for you. And then? After Miss Kendra teases and shames you into arousal? You are going to spill all your worthless wussy cream into your sissy panties for Kendra. And then your real humiliation begins...

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62826 - Humiliatrix College Intern Tori Plugs and Panties You

Your college intern Tori just learned all your most embarrassing submissive sexual weaknesses. She's gonna spill the truth about your panty proclivities unless you willingly submit to be sissy-trained. You're not in charge anymore, wussy panties. Mean Princess Tori is the boss of you now. Ready to be plugged and pantied?

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62620 - Humiliatrix Miss Tessa Punishes You in Sissy Panties

Tess has decided to send you on a punishment assignment to show you exactly what she thinks of you as a man. Your humiliation begins with a snug pair of pink sissy panties tugged tight around your laughable little package. Strip and put your panties on while Tessa tries to contain her laughter. Once you're properly attired, Tess is going to send you on a public sissy punishment assigment!

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62905 - Panties and Punishment Fucking by Humiliatrix Jaycee

Your gym trainer Jaycee warned you. Act like a little bitch and you're gonna get treated like a little bitch. And then you dumbly decided to get all 'macho man' in front of Jaycee's girlfriends. Well, you're not so tough when kickboxer Jaycee is strapping on a dildo. Are you, little mister sassy mouth? Better put on your wussy panties and apologize. Cuz you're about to get schooled and fucked by a girl.

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