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Showing 1 - 60 Videos

Sis Helps You Crossdress video from Fiona Dagger

Sis Helps You Crossdress by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera! There is no real sexual action in this video, it's just crossdressing encouragement, but a part 2 will be coming soon where bro and sis mutually masturbate together!) Your big sister walks into your room without knocking, about to ask you if you want to go to the gym with her - but she's shocked to find you wearing a dress and admiring yourself in front of the mirror! At first she gives you the benefit of the doubt and assumes you must have a costume party, but you fumble your excuses and she quickly realizes that you're lying! She tells you it's okay, you can tell her the truth - did you just want to know what wearing a dress felt like? You're so embarrassed but you admit that yes, you just wanted to dress up in cute girl clothes to see how it felt... Your sister tells you not to feel bad about it, and that she's happy you're experimenting - but that the dress you're wearing is really ugly, so how about she lets you try on some of her clothes, which will suit you a lot better! She fetches a few dresses for you to try on, and suggests you start with a cute pink sundress. She's very supportive of how it looks on you, telling you that you look really good, but that she can't help but giggle a little in shock as it's just so strange seeing her little brother dressed like this! The next dress you try on is a sexy, tight bodycon one, so she instructs you on how to roll it onto your body and warns you that it will be very formfitting! The dress feels so nice that you can't help but get an erection, and when your sister turns back around she immediately spots it, as the dress is so tight that she can basically see the outline of your hard cock super clearly! You're embarrassed again but she tells you it's fine, she did kind of guess that this was a sexual thing for you, and she doesn't want to shame you at all - in fact she reiterates that she thinks you look really nice, even saying that maybe in future she'll ask her boyfriend to try wearing a dress for her! She tells you she brought another dress in, but warns you it's very sexy - it's basically a babydoll nightie, with massive slits up each side so it doesn't leave much to the imagination... You put it on and your boner sticks out so much that your sister giggles even more, but she also can't seem to take her eyes away from you! She shyly suggests you try some actual lingerie, and fetches some stockings, and a bra and panties from her room. She teaches you how to put the pale pink, lace top stockings on first, and then tells you to put the red, lacy lingerie on - warning you that the panties are very small and won't cover much at all! Once you've put it all on she can't stop staring at your hard cock, barely constrained by the tiny strip of red fabric, and after giving you lots of compliments and promising that you look really good, she suggests she leave you alone so that you can take care of your boner - and tells you just to wash the lingerie before you give it back to her! As she leaves she keeps glancing at you and at your hard cock, and you wonder if she might even be going to 'take care' of herself as well... TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, taboo , bro sis, brother sister, crossdressing, crossdresser, cross dressing, cross dresser, sissy, sissification, encouragement, lingerie, big sister, little brother

^$7.00 Add to Cart

roommate catches you crossdressing and makes you her bitch - spanking, chastity, numbing cream, tiny condom, anal dildo video from Veggiebabyy

roommate catches you crossdressing and makes you her bitch - spanking, chastity, numbing cream, tiny condom, anal dildo by Veggiebabyy This is a custom video! Contact me if you’d like your own! After catching you (my roommate) dressed in my clothes for the third time recently, I decide it’s time to do something about it. The video starts with you across my lap, where I pull your (well, MY) panties down and spank your bare ass until it’s nice and pink. Wait a second… did you just leak all over my new black pants?? I can’t believe that! Stand up! I can’t have your tiny clit ruining my clothes. I cover your little clitty in numbing cream, then a tiny finger condom, then a cute pink chastity cage. You won’t be making a mess now. Back across my lap, it’s time to give you want you really want. You clearly want to be my girlfriend so badly, and if you want to be my bitch, you’d better learn to cum like one. I pull out a big pink dildo that I found while cleaning recently and slide it deep in your bussy. I pound away until I hear you moan that you’re going to cum. I don’t want you to cum yet, so I push the cock the whole way in your ass, pull the panties back up to keep it in place, and tell you that you only cum when I say so.

^$8.00 Add to Cart

Sissy ass kicking video from Nicolette Bloom

Sissy ass kicking by Nicolette Bloom Tonight is a very special night. Tonight is all about me being turned on and you doing whatever it takes to do that right? Because you already know that it's only right for a sissy to obey their handler right? Good. Tonight I am going to cum while I watch you get your ass kicked!

^$22.00 Add to Cart

Cock Servicing Practice 3 video from SinSpice

Cock Servicing Practice 3 by SinSpice "Cock Servicing Practice 3" - CUSTOM - Buyer Comment: "Looking for a 13m+ CEI video where you tell me to grab my cumming dildo, and instruct and teach me how to suck on it on it like it was real, and make it explode in my mouth, face, or wherever you want. I want you to tell me where to put it, on my desk, on the wall, on the floor, however you want. I would like you to demonstrate with your dildo telling me how to please it, including pointing it at the camera and telling me where to take the cumload. You can make me cum multiple times if you want, such as on the dildo and sucking it off or wiping it over my face or licking it off the floor." Have the automatic squirting dildo cum at approximately 5, 10, and 12.5 mins. #cei #bbc #sissy #sissification #femdom #training #subtraining #bisexual #cock #servicing #redhead #milf #bigboobs #bignaturals #fetish #custom #BTO #cumeating #instructions #teaching #teacher #sophiasinclair #mssinclair #mistress #goddess #sinspice #sinspice2020 #hot #nude #naked #usa #mo #sucking #blowjob #dildo #homemade #amateur #domination #oral #mouth #tongue #cocksucking #cocklover #youlovecock

^$8.00 Add to Cart

CBT Sequal Booty & Pussy Adoration, Nude Tease & Femdom Cum Command! video from Victoria Lotus

CBT Sequal Booty & Pussy Adoration, Nude Tease & Femdom Cum Command! by Victoria Lotus Picking up right where we left off, your MILF Goddess Victoria Lotus is back in sultry lingerie that hugs my thick booty and hourglass curves, ready to escalate your sissy submission! Spin the wheel again for even naughtier femdom tasks – from worshipping my delectable long-legged ass with your tongue in mind-melting booty devotion, to dropping to your knees for pussy worship that leaves you begging for more of my wet, teasing folds. I strip down to full nudity, my green eyes locking on yours as I command every moan and stroke in this amateur BDSM fantasy. Feel the heat build as my flirty smile turns wicked, ending with a dominant cum countdown that demands you explode in total surrender. Who's my devoted pet ready for round two? Unlock and worship now! sissy sequel, femdom worship, lingerie tease, booty worship, pussy worship, nude femdom, wheel spin tasks, MILF domination, BDSM goddess, amateur nudity, ass adoration, pussy tease, dominant JOI, sissy training, findom command, fetish escalation

^$25.00 Add to Cart

Taboo Bimbo Programming Your New Bimbo Name video from Lacey Royce

Taboo Bimbo Programming Your New Bimbo Name by Lacey Royce Mommy is not happy with you. She's upset that you’re doing well in school. She keeps telling you that you’re not smart, and not at all manly. She says that you need to listen to "Daddy" and embrace your true sissy self. She’s committed to her bimbo journey and is taking you with her. The second she places those silly, pink, headphones on your head your mind instantly goes blank and empty. As the days go by, Mommy encourages you to dress up in more and more slutty outfits, teaching you how to walk and talk like a bimbo! She's always praising you when you do something stupid, like not knowing that Africa is a continent… Oops! And now, she's going to give you a new sissy name to help you truly accept your new identity. As you begin to listen to Mommy, learning how to be a slutty bimbo with her, she brings you into her special bimbofication room. She’s going to show you how a good, dumb, bimbo whore sucks a cock… starting with Daddy! As your dumb, bimbo brain fills with Mommy’s helpful teachings you’ll find yourself permanently feminized and bimbofied - there’s no going back!

^$20.00 Add to Cart

Training a New Puppy's Mouth video from Ryley Rails

Training a New Puppy's Mouth by Ryley Rails I have a new puppy to train, Misty T. so I break in her mouth and have her suck my cock, teaching her how to be a good sissy cock sucker! I finish with giving her a big facial for everyone to see!

^$10.00 Add to Cart

Mrs Roses Lingerie Addiction video from Siena Rose

Mrs Roses Lingerie Addiction by Siena Rose Mrs. Rose’s lingerie addiction is her biggest fetish. She’s picked several colors to model for you while you edge and please yourself. Watch her bounce her tits, striptease and sway for you to the music while you get lost in her world for a little while. TAGS: #GODDESS #FEMDOM #MILF #LINGERIE #SISSY #JERKOFFENCOURAGEMENT #LONGNAILS #LOVINGFEMDOM #TITBOUNCE #STRIPTEASE #MUSIC #EDGING #NYLONS #STOCKINGS #THIGHHIGHS #BRA #PANTIES #GARTER #HONEYBIRDETTE #RED #ORANGE #GREEN #BLUE #PURPLE #NIGHTGOWN #BLUEEYES #BRUNETTE #SOFTCORE #BIGTITS #BUBBLEBUTT #CURVY #UPDO #PEARLS #MODEL #TRYON

^$10.00 Add to Cart

Being a Girl ROCKS video from Adora Bell

Being a Girl ROCKS by Adora Bell I totally see why you want to be a Sissy Feminized slut. Being a girl is so much fun! Cute clothes, panties, mani pedis, other female company. But its not just all the fun cute things about being a girl that’s alluring you. You also want it so you can get big fat cocks and more male attention. You want to be filled up in every hole with cum and be a huge slut huh?! I think you’d be really good at getting their cum. We just have to start with shopping!

^$15.00 Add to Cart

Sissy Punishment - Femdom Punishment for Sweet Catch from Laura Ropes with Feminization, Maid Fetish, Sissy Sluts and Spanking video from Laura Ropes

Sissy Punishment - Femdom Punishment for Sweet Catch from Laura Ropes with Feminization, Maid Fetish, Sissy Sluts and Spanking by Laura Ropes SweetCatch, in his awkward attempt to serve me, fumbled and splattered a few drops of my carefully concocted drink. The liquid, a rich crimson reminiscent of the vibrant hues of a summer sunset, flowed over the glass's rim like a tiny cascading waterfall. His actions demanded correction. Donning a stern expression, I decided on a memorable lesson. Taking precise action, I delivered a swift series of chastising swats that left his backside flushed with a fiery scarlet hue. This ensured that the message was unmistakably conveyed and the error not easily repeated.

^$6.00 Add to Cart

Sissy Training: Booty Pic Practice - Clara Dee JOI video from Clara Dee

Sissy Training: Booty Pic Practice - Clara Dee JOI by Clara Dee Let me show you how to take sexy selfies! Go put on your cage, and some cute panties. Now arch your back, purse your lips... great job babe! Ok, a few more poses, and then as a treat, you can cum with your vibrator. KEYWORDS: Sissy, JOI, sissy wife, sissy training, chastity, sissy JOI, chastity JOI, cum countdown, sissy dress up, sissy chastity, Clara Dee JOI, roleplay, feet, soft femdom, sissy chastity, panties, panty wearing, spreading, ass spread, pussy spread, ass spreading, pussy spreading, pussy reveal, blonde, big butt, big ass, round butt, thick, thick thighs, chubby, thick ass, pretty face, MILF, chubby MILF, small tits, natural boobs, booty, butt, ass, jeans, jean shorts, pussy, holes, asshole, tight pussy, pussy reveal JOI, vibrator JOI, cum countdown JOI, thong, caged cum, jerk off instructions, girl next door, shaved pussy, gentle femdom, Length: 13 minutes

^$13.00 Add to Cart

Training My Good Girl Sissy Bitch - 4K - Sissy Nipple Training Schedule And Demonstration, Rules For Chastity, Foot Bitch Motivation, Strap-On Worship video from The Goddess Clue

Training My Good Girl Sissy Bitch - 4K - Sissy Nipple Training Schedule And Demonstration, Rules For Chastity, Foot Bitch Motivation, Strap-On Worship by The Goddess Clue *Custom Request* Sometimes good girls need a strict Mistress to put them in their place. Follow the training regimen I curated for you. This will ensure you make Me happy and make you a good girl. I explain in great detail what I require of you. Your sissy clit must be caged at all times. Your sensitive nipples will be trained to be your main source of pleasure. Hours must be dedicated to worshipping My Goddess cock. First, I will remind you of the basics. Your clitty must be locked in chastity 24/7. No excuses. Goddess despises excuses. The less pleasure you gain from it, the more can be redirected elsewhere. Your denial is vital to your training. Those slutty nipples are now your most arousing zone. You are unworthy to see your Goddess topless but I will tease you with My cleavage and you thank Me for the privilege. When it comes to your nipple play, I have a faux pair of breasts to demonstrate on. I show you My favorite ways to tease, pinch and rub nips. I suggest you watch closely and listen carefully to learn how I wish to train you. As My fingers rub the practice nipples, I explain the schedule I want you to follow. It is easy. All you have to do is obey. Finally, I display My 12 inch strap-on. The purple jelly dick sways between My thighs, captivating you. You will be loyal to your training and to My Goddess cock. As you train your body, you will worship it. Your slutty holes will not be neglected. To solidify all that I've taught you, I prop My feet up once again. You are a foot bitch, always, and My soles are your biggest motivator. Allow the way they make you feel inspire your devotion to your training.

^$26.00 Add to Cart

My cuck is a sissy video from AnittaGirl

My cuck is a sissy by AnittaGirl I sit back comfortably in my red chair, cigarette between my fingers, sipping slowly. I glance at you with a smirk. Good girl, doing exactly as I said and looking so feminine. My voice is soft but commanding. Now go stand across the room. Let me get a good look at you. You obey. I tilt my head slightly, watching every little detail. Turn around... mm, yes, you're improving. Setting your hair in curlers and painting those delicate little nails—such a good girl. I smile, amused. Now curtsy for me… that’s it. And crawl. Crawl over here like the obedient sissy you are. You reach me, kneeling low. Kiss my feet and beg me for a treat. As your lips press against my toes, I begin to speak, casually, as if reminiscing. I had the most incredible night with a real man… strong, dominant… everything you’ll never be. I let out a soft laugh, dragging the story out with cruel delight. And while you're down there, licking like the good little cuck you are—why don’t you lick his cum too? I mock you between every sentence, repeating how weak, soft, and utterly feminine you’ve become. You’ll never be a man. You’re just a pretty little sissy cuck with long, curly hair and no pride left. Finally, I wave my hand dismissively. You may leave now—oh, but not before you bring me a drink. I cross my legs, exhale slowly, and wait. As you know I am a non smoker, I am not smoking the cigarette on the clip.

^$7.00 Add to Cart

Sissy Dress Up Session video from Tabitha Angel

Sissy Dress Up Session by Tabitha Angel You show up to serve Me just as I ordered you to - completely shaved from head to toe. You had to remove every single hair before you showed up, and stripped naked at the feet of Tabitha Angel. You look good like that, submissive and subservient to a proper FemDom. I give you the panties off of My body, and make you wear them for Me. You are going to be My good little sissy toy.

^$5.00 Add to Cart

Panty Sniffer Sissification JOI & Transformation video from Stella Von Savage

Panty Sniffer Sissification JOI & Transformation by Stella Von Savage It's that time again! Your wife is gone, time to raid the laundry for dirty panties while she's away. I have you inspect sniff, taste each pair, wrap them around your cock. Wait... you're enjoying these panties WAY too much. I see how you're looking at them, and I can tell you secretly want to WEAR THEM. I knew it! This is more than just a panty fetish for you. You're a closet sissy, but I'm going to help you embrace your crossdressing sissy side today. You start this half hour thinking that you have a simple panty fetish, but end up being my full blown panty sissy slut! I have you try on different pairs, rub your sissy clit through the panties, pull the panties to the side & jerk while sniffing & tasting another pair, rotate thru a few pairs, licking, sniffing, sucking, tasting, indulging. It's happy half-hour for your sissy cum drink. I give you a countdown, where I make you put your precum-filled pair of panties in your mouth & taste the mixed cum while you blow your load into another pair of her panties. Then you'll clean up all your mess like a good sissy. Will your wife find out?

^$15.00 Add to Cart

Painting Brie's Face 4k video from Ryley Rails

Painting Brie's Face 4k by Ryley Rails Brie is eager for my tgirl cock and cum! She sucks it hard with the reward being a face covered in cum! Then she eats it all up like a good girl! Shot in 4k

^$10.00 Add to Cart

Dress Up and Play video from DestinationKat

Dress Up and Play by DestinationKat I tell you to get dressed up in your most favorite sissy or girly themed outfit. You're going to masturbate for me in it. You're also going to need a dildo or just your fingers. I want you to imagine that you're riding me while you fuck your ass. I talk about all the ways this could happen while showing off and holding the dildo onto myself. Imagine how much fun we could have together. Gentle femdom theme.

^$4.00 Add to Cart

Girl Transformation Complete: Sissy Breeding with Dommy Rose video from PaintedRose

Girl Transformation Complete: Sissy Breeding with Dommy Rose by PaintedRose You tried to resist Dommy when I told you that you'd be better off a girl with your love of girly things but you have now complied with feminization transformation. Since you've gone on the hormones to grow ginormous tits and had your penis converted to a pretty pink pussy - you've been feeling really girly and even turned on by the thoughts of being fucked! Dommy takes off the cage to see how your new pussy has healed and you immediately get swollen and begin to drip from your fully functional new pretty pussy. You look so hot in your matching outfit and It's been a while since you've had an orgasm so I decide that you may rub your pussy through your pantyhose for me. I can sense the need, the need to breed and be filled so full of my strap dick and cum. I am just the Dommy to do it - you are my girl and I am going to be the first one to breed that pretty new pussy and keep you pregnant. This 2257 compliant film is a solo performed adult roleplay fantasy that features, Satin Panties, Feminization, Sissy Training, Sissy Slut, Sissygasm, Girl-Pussy, Clitty, Boy To Girl Transformation, Light humiliation, Chastity and Release, Edging, Step-Mom Taboo Roleplay, Caught Peeping, Panties, Fullback, Bikini, Strapon sex, Cum Control, sissy breeding and impregnation, Orgasm from fucking femdom fetish kink.

^$17.00 Add to Cart

Cock Servicing Practice 4 video from SinSpice

Cock Servicing Practice 4 by SinSpice "Cock Servicing Practice 4" - CUSTOM - A second dildo has been added to this custom clip. Buyer Comment: "Looking for a 13m+ CEI video where you tell me to grab my cumming dildo, and instruct and teach me how to suck on it on it like it was real, and make it explode in my mouth, face, or wherever you want. I want you to tell me where to put it, on my desk, on the wall, on the floor, however you want. I would like you to demonstrate with your dildo telling me how to please it, including pointing it at the camera and telling me where to take the cumload. You can make me cum multiple times if you want, such as on the dildo and sucking it off or wiping it over my face or licking it off the floor." Have the automatic squirting dildo cum at approximately 4.5, 10, and 13.5 mins. #cei #bbc #sissy #sissification #femdom #training #subtraining #bisexual #cock #servicing #redhead #milf #bigboobs #bignaturals #fetish #custom #BTO #cumeating #instructions #teaching #teacher #sophiasinclair #mssinclair #mistress #goddess #sinspice #sinspice2020 #hot #nude #naked #usa #mo #sucking #blowjob #dildo #homemade #amateur #domination #oral #mouth #tongue #cocksucking #cocklover #youlovecock #cumslut #gooner #gooning #obsessed #addicted #craving #sluty #boobs #tits #nipples

^$9.00 Add to Cart

HOTTEST HAND JOB EVER video from Aurora

HOTTEST HAND JOB EVER by Aurora The hottest hand job you will ever see with a massive cumshot!

^$9.00 Add to Cart

Slutty Femboy Anal Training Sissygasm video from Cristy Noir

Slutty Femboy Anal Training Sissygasm by Cristy Noir Riding my huge white dildo in reverse cowgirl like a good little slut while wearing chastity. Getting better at anal training but this 30min ride definitely left my ass all used up like a slut :3 Then i cum in my little cage at the end like a girl :P

^$9.00 Add to Cart

Feminization Mind Fuck Full Immersion video from Claudia Kink

Feminization Mind Fuck Full Immersion by Claudia Kink Welcome to your new room! Well, technically it is your old room but it has seen a huge makeover. Everything is pink now – this is the feminization room, for building and remaking a perfect sissy slut. The other important addition is that it locks from the outside now. You’re going to stay in here while the reprogramming occurs. I’m so excited to turn you into the perfect feminized little sissy. Being surrounded by pink – pink walls, pink ceiling, pink carpet – should help to prime that little brain of yours. Your first lesson is that you are nothing but a hole for me to use. Get down on your knees and suck this strap-on. You aren’t allowed to cum until you can deep throat it…

^$14.00 Add to Cart

Cum Like a Girl - Feminized for a Girls Only JOI video from Kim And Vivi

Cum Like a Girl - Feminized for a Girls Only JOI by Kim And Vivi We show off all the sweet things we put in your Sissy Kit and tell you what to do with them. Including lotion, a razor, nail polish, lip balm, lipstick, a pair of Victoria Secret Panties, and even a collar with your new name on it. Once you're all dressed up, Kim gives you a sensual JOI, teaching you how to touch your pussy, while Vivi follows along. Get prepared for this vid with a pink insertable toy, and some lube

^$19.00 Add to Cart

Mommy Feminizing You video from Meganluv69

Mommy Feminizing You by Meganluv69 She caught you prancing around the house in her favorite panties. She thinks she has a better pair that will fit you better and she wants to see you put them on. She is all for you cross dressing. She even uses her vibrator on your penis and makes you feel as pretty as you look.

^$6.00 Add to Cart

Sissy Dress-Up Spitroast - Clara Dee POV Virtual Sex with Elle Eros video from Clara Dee

Sissy Dress-Up Spitroast - Clara Dee POV Virtual Sex with Elle Eros by Clara Dee It's date night, and your wife Clara has a surprise. Her friend Elle is joining you again! They've prepared some pretty pink lingerie for you, and a cute little dress. Clara does your makeup, and then they have you pose and show off how pretty you look! You're such a pretty little sissy, they can't wait to fuck your holes with their strap-ons. KEYWORDS: Virtual sex, sissy, pegging, strap on, airtight, spitroast, sissy dress up, pussy, Clara Dee POV, pegged, POV pegging, sissification, feminization, roleplay, dildo, strap-on, spreading, pussy spreading, spread pussy, GFE, wife, reality, praise, encouragement, soft femdom, gentle femdom, clit rubbing, boobs, real boobs, real tits, shaved pussy, hairy pussy, girl next door, small tits, small boobs, MILF,

^$13.00 Add to Cart

Condom Cumsicle CEI for my Sissy - Clara Dee JOI video from Clara Dee

Condom Cumsicle CEI for my Sissy - Clara Dee JOI by Clara Dee Hey sweet sissy, I have a delicious summer treat for you! You're going to stroke your clitty and fill up a condom with cum, to make a tasty frozen cumsicle! Add some water, tie it off, and pop it in the freezer. Once it's frozen, come back for round two. You'll suck and lick your tasty treat until it's all gone. Once you've swallowed it all, you can cum again. Keywords: JOI, CEI, sissy, condom, saved load, saved load CEI, dildo, cum countdown, cum twice, Clara Dee JOI, jerk off instructions, cum eating instructions, MILF, chubby, thick, thick thighs, big ass, thick ass, daddy, feet, armpits, asshole, pussy, holes, thong, small tits, blonde, girl next door, shaved pussy, sexy, ass, pussy,

^$16.00 Add to Cart

Pegging POV - Your New Life as a Sissy Wife video from Kim And Vivi

Pegging POV - Your New Life as a Sissy Wife by Kim And Vivi So, you want to experience the married life, but you were never much of a man, do you really think your place is as a husband? I don't think so, not after seeing how eager you are to take cock. In fact, Kim thinks you're better suited to be her full time wife. Just leave all the husband responsibilities to her, like making sure you get your daily dose of dick, and stay absolutely full of cum. You're going to make such a beautiful bride, Vivi will walk you down the aisle, and the two of them will fuck you senseless on your wedding night, right after you vow to be the most perfect Sissy Wife.

^$14.00 Add to Cart

Eat All Your Cum for My Feet - Sissy JOI Mindfuck Goddess Kyaa in Leather Lingerie video from Goddess Kyaa

Eat All Your Cum for My Feet - Sissy JOI Mindfuck Goddess Kyaa in Leather Lingerie by Goddess Kyaa Worship me in leather lingerie as I tease you from inside the dungeon. I know your weakness is my gorgeous feet, and I know that you are a pathetic sissy. So I take advantage of both, turning you into my stupid horny, sissy slut, while making you rub your pathetic, sissy, clits to my perfect oiled bare feet! I will guide you to sensual yet strict jerk off instruction and humiliate you for being my sissy bitch! Contains: sissy mindfuck, JOI, jerk off instructions, foot fetish, CEI, cum eating instructions, feminization, sissy sluts, sissification, mindfuck legs, ass fetish, humiliation, powerful women, femdom, female domination, Kyaa's Empire, Kyaa Chimera, Goddess Kyaa

^$12.00 Add to Cart

Playtime 69 video from Ryley Rails

Playtime 69 by Ryley Rails When two sexy tgirls get together we decide to play around so we 69, face fuck, gag, lick, and slurp all over each other's cock until I shoot a big load of cum all over Brie's face!

^$15.00 Add to Cart

Effeminate video from Adria Nite

Effeminate by Adria Nite You come back home looking for your roommate. You burst into her room jumping in happiness. You show her your new possession - a magic remote. She laughs at you and tells you not to start that whole magic thing again. You point the remote at her and she laughs even more because nothing happens until she’s right there in front of you naked. She screams at you in shock, covers herself up and snatches the remote out of your hand. After a few failed attempts, she dressed again. You try to get your remote back but she points it at you stating that she’s in charge now. She asks you politely who you’d like to become but ignores everything you say and decides to transform you into a woman. She starts small with just changing your eyes but with every click you look more and more like a woman. There’s no place to protest now - you have to embrace it. She goes over every single detail of your appearance describing what she’s doing as she plays with the remote. For the grand final, she gives you a pussy. That’s when all the hormones start doing their job and you stop just feeling like a woman - you are one. You instantly get horny but she has a solution to that - she lets you try a dildo for the first time. Seeing how wet and turned on you are, she realises she may as well make some money with your help. Will you be good at your new job? Tags in the video: gender transformation, magic transformation, transformation, transformation fetish, transformation fantasy, magic remote, magic control, man to woman, femdom, domination, female domination, magic fantasy, erotic magic, sissy, sissy fantasy, sissification, feminization

^$17.00 Add to Cart

HAPPY BIRTHDAY TO A PUSSYFREE TRUCKER SISSY! NOW MASTURBATE TOGETHER 1080P - ELLIE IDOL video from Ellie Idol

HAPPY BIRTHDAY TO A PUSSYFREE TRUCKER SISSY! NOW MASTURBATE TOGETHER 1080P - ELLIE IDOL by Ellie Idol Happy Birthday to Ellie Idol's little porn addicted pussy free trucker! Here's to another year of rubbing your little clitty while fantasizing about cuckolding scenarios. Have you made your wish? You probably would wish for infinite time to play with your clit in panties. Endless days of mindless masturbation for a freak like you... Ellie's ass and tits are just some of your weaknesses, and she's going to show them off to her b-day cuck! You'll need to pop on your girly panties before you can begin touching yourself. Getting off with Ellie on your birthday is the perfect treat! Heck, she may even invite some hung studs over to fuck tonight while you remain sexless. For now, she has her long and thick dildos to be entertained by. You're going to watch and rub it like a girl while she plows her holes with 9 inches of rubber! Watch her suck and fuck them as you imagine her being bred by real men. They get to fuck on your day of birth and you DON'T, sissy!! Now, celebrate with a b-day orgasm along with Ellie!

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SELF-FACIAL CEI: A Step-by-Step Guide video from AnittaGirl

SELF-FACIAL CEI: A Step-by-Step Guide by AnittaGirl Today, I will teach a sissy how to behave and become the perfect sissy. Like all sissies, she is wet and ready to ejaculate, but it won’t be that easy for her. She will have to wait until I give her permission and instruct her on how to ejaculate onto her own face.

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Fucking In the Great Outdoors w/ Ryley Rails and Brie Lovely video from Ryley Rails

Fucking In the Great Outdoors w/ Ryley Rails and Brie Lovely by Ryley Rails The woods are so much fun to fuck and play it! I drop to my knees when I met Brie Lovely and start slobbering all over her big tgirl cock gagging on it before she slams it into my ass fucking me all over the woods until we both cum with me giving her a huge facial!

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Pegging a sissy slut till the orgasm video from AnittaGirl

Pegging a sissy slut till the orgasm by AnittaGirl This sissy slut asked for a custom video with me making "she" have a strong orgasm but in my count, so as a dominant female i am i made her feel this cock really deep on "her" butt till gets juicy! I can perform this video with a coperformer :) ask me for a custom vid OLD VIDEOS GOT A SPECIAL DISCOUNT

^$4.00 Add to Cart

2 YEARS AFTER SHE FOUND YOUR JOURNAL 1080P - ELLIE IDOL video from Ellie Idol

2 YEARS AFTER SHE FOUND YOUR JOURNAL 1080P - ELLIE IDOL by Ellie Idol It's been a whole 2 years since you committed to being pussy-free! Impressive! Now, to get this out of the way, Ellie lets you know she broke up with her boyfriend. This gives you an exciting opportunity to be her live-in cuckold, if you so desire, of course. Listen up, as there are rules to follow! You'll remain sexless towards women but get fucked by men or do fluffing if she so desires it. You will also have creampie and asshole cleanup duty! All while keeping with the special dress code Ellie has come up for you and only having orgasms when she allows it. Remember your mantras, tasks, and position, and you will be rewarded heavily... Just talking about it makes counselor--no, roommate Ellie playful and horny! Are you ready to cum together?? You have permission! Now, aren't you excited to move in? (Be sure and check out parts 1-4 before watching this video)

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Chicks and Dicks video from Ryley Rails

Chicks and Dicks by Ryley Rails Sharing a big, yummy cock with the sexy slutty Brie Lovely! We suck on a large cock together, taking turns licking up and down his shaft, gagging on it! Then use our sissy cocks and make each other suck on two cocks going back and forth from a yummy big cock to a tasty sissy tgirl cock until we get off!

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Shop Girl: Matching Sets - Sissy Feminization Training video from PaintedRose

Shop Girl: Matching Sets - Sissy Feminization Training by PaintedRose You see an ad posted for a "Shop Girl" for a luxury panty and lingerie shop just around the corner and apply within. The manager says that the dress code is very strict and that you would have to model the lingerie you are selling among other girly activities. Rosie is firm but decides to give you a one day trial training. Do you have what it takes to be a Shop Girl? This film is solo performed and 2257 compliant and features, Satin Panties, Feminization, Sissy Training, Sissy Slut, Sissygasm, Girl-Pussy, Clitty, Boy To Girl Transformation, Light humiliation, Chastity and Release, Edging, Femdom Roleplay, Caught Peeping, Panties, Fullback, Bikini, Strapon sex, Cum Control, Orgasm from guided masturbation and a Dommy femdom fetish kink. #Sissy #Feminization #Goddess #Panties #Satin #StrapOn #GirlDick #Training #Femdom #Roleplay #POV

^$25.00 Add to Cart

Sissy Strap-On Training video from Claudia Kink

Sissy Strap-On Training by Claudia Kink Look at this big cock. It is the biggest one I own, 12” of thick hard cock. And guess what? You are going to take all of it in your slut hole. You want to be such a good sissy slut for me, don’t you? And you know that sissies like you only exist to be used and fucked and filled. I’m going to stretch you open with this huge hard cock, and fuck you until you’re gaped and ruined, just like a slut should be.

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Your Girlfriend Found a BIGGER Cock - Sissy, SPH, Cucking video from Kim And Vivi

Your Girlfriend Found a BIGGER Cock - Sissy, SPH, Cucking by Kim And Vivi Ever since she caught you in the girls locker room, you've been living in fear of your futa bully. One day when she discovers you have a girlfriend-- a hot one, so of course she sends her some incriminating photos of you. Desperate to secure your relationship, you visit your girlfriend's house, where she has a kinky surprise in store for you. She doesn't seem mad at all, but you'll do anything to stay on her good side. She manipulates you into some sexy lingerie, and as you succumb to her seduction, someone knocks on the door! Quickly, she hides you in her closet. Your futa bully has arrived! Not just to tease and taunt, but to take what is rightfully hers. As she moves in to claim your girlfriend with her dominant presence, a rustle in the closet catches her attention. To her delight and your horror, she discovers you, dressed in your girlfriend's delicate lingerie, the very image of a sissified plaything. Far from being deterred, your futa bully is actually turned on by just how well girls clothes fit you, and her cock hardens at the thought of having you under her control. She likes you as a sissy and decides to make you submit to her in ways you never imagined. If you can't please her, your girlfriend will have to take your place. Inexperienced and nervous, you struggle to service your bully's impressive cock, so your girlfriend demonstrates the art of giving a hand job to a much bigger dick, all while you watch, your own manhood feeling insignificant in comparison. As your girlfriend expertly strokes your bully's cock, you're subjected to the humiliation of both women commenting on the contrast between your sizes. Already feminized, humiliated, and cucked, your final job is to choose a place for your futa bully's hot cum, do you want it all over your bra, aimed right at your panties, or will you spit your tongue out like a good girl, and take it down your throat?

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Tricking You into Losing Your Anal Virginity to Me video from 420sextime

Tricking You into Losing Your Anal Virginity to Me by 420sextime Hey... I wanted to ask you something... Would you be the man who takes my virginity? You would!! Oh my god I knew I could count on you. I'm really scared though, is it ok if we made it a little more even so I'd be comfortable? What if... I take your anal virginity first? Really?? You would let me fuck your ass??? Ok well bend over, and get ready to lose your virginity. But while I have my cock up your ass, there's something I should tell you. You're the third beta bitch boy that I've fucked up the ass this week!!!! Ahahahahaha!!!!!!! Includes: Pegging, anal virginity, humiliation, femdom, brat, mean, mean girl, beta, domination, solo female, anal training, gnd, girl next door, cute, tricked, strapon, strap on, strap-on

^$15.00 Add to Cart

Sissy Wife Date Night Anal JOI - Clara Dee JOI video from Clara Dee

Sissy Wife Date Night Anal JOI - Clara Dee JOI by Clara Dee Let's go out tonight! I'll help you get all dressed up and act like a lady, so you can pick up a big strong man to fuck you. In fact, let's practice what you're going to do to him when you get him home! Grab your dildo and show me how you'd suck him, and how you'd take his throbbing cock in your sissy pussy. You look so pretty with a dick in your ass. KEYWORDS: Sissy, JOI, sissy JOI, sissy wife, anal JOI, sissy dress up, feminization, Clara Dee JOI, high heels, armpits, anal instructions, jerk off instructions, SFW, non nude, sissy instructions, wife, GFE, dildo JOI, sissygasm, MILF, chubby, thick, small tits, blonde, girl next door, cute, pretty,

^$12.00 Add to Cart

The Moment You've Been Dreading video from Kim And Vivi

The Moment You've Been Dreading by Kim And Vivi You thought you were playing it safe, only sending your anonymous sissy pics to your online dommes, but that couldn't be further from the truth. For this video, we didn't need to create a fantasy for you... because the reality is, your photos have already been sent to your friends, family, and yeah, even your job! We've had these incriminating photos for a looonng time, and we're not the only ones. You've been sharing these pics with so many dominant women online just begging to be humiliated and degraded. Well now, we're giving you what you want. You can no longer hide, sissy. It's time to live as a girl full-time, servicing men and embracing your true slut nature. Your secret's out, and there's no going back.

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Training My Sissy video from Siena Rose

Training My Sissy by Siena Rose Small dicked Sissies are Mrs. Rose's favorite and everyone loves her big Bad Dragons. You've been watching your Matriarch of Dragons stuff her holes and you want to join in on the fun. Mrs. Rose is more than happy to show you how exactly what she thinks about that little clit you love playing with. Grab your lube and your favorite stuffy while Mrs. Rose prepares you for your first Bad Dragon play session with her. Are you ready to make puddles, Sissy? Good Boy. #FEMDOM #SISSY #STRAP #PEGGING #MILF #GODDESS #BISEXUAL #BETA #BADDRAGON #DILDO #DIRTYTALK #POV #COCKWORSHIP #SUBMISSIVE #SLUT #BOTTOM #REDHEAD #OLDERWOMAN #MOMMYDOMME #KINK #FETISH #SPH

^$11.00 Add to Cart

Brie Lovely's Slut Exam video from Ryley Rails

Brie Lovely's Slut Exam by Ryley Rails It's time for your slut exam! I check on all of Brie Lovely's skills like making out and getting face fucked before she takes my sissy cock deep in her ass until I cum on her face!

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Shore Leave Gets Spicy video from Ryley Rails

Shore Leave Gets Spicy by Ryley Rails I'm on shore leave and so it the captain! I wanna make sure he has a good time so I seduce him kissing him, licking and sucking on his cock. Then I let the captain pound away at my ass and ride his cock until he unloads all of his cum onto me! Shore Leave should always be this fun!

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Anal Night at the Cabin video from Ryley Rails

Anal Night at the Cabin by Ryley Rails I'm excited to see you! I already have a rock-hard cock, but I want you fuck my ass! Tonight, it's about plowing me, making me go ass to mouth multiple times watching as my hard sissy cock flops around! Fuck me till you cream pie my ass then watch as I shoot a big load of sticky cum all over myself!

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Cucked at my feet by a BBC video from Meganluv69

Cucked at my feet by a BBC by Meganluv69 I cuck you at my feet worm with my favorite BBC. It's so powerful and strong something you WILL NEVERR BE. I love to see boys squirm and that's exactly what I plan to do with you worm...

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Sultry Sensual Sissy Slut: Goddess Dommy Rose video from PaintedRose

Sultry Sensual Sissy Slut: Goddess Dommy Rose by PaintedRose Do not fret my sweet and obedient-pet. Your darling Dommy knows just how to cheer you up with a dress up play date. A little lip gloss and sexy outfit is just what you need to stimulate your erotic need to serve sweetly and say pretty please. Be at ease and you will please.. ME on your knees. It turns me on to see you like this and for that I will show you my strap on Dommy dick! I am aching to see your pretty lips kiss, lick, and suck it. You feel that clitty getting so erect and throbbing that you do as Goddess demands to please me and CUM. You love your Goddess Dommy Rose. This film is a solo performed roleplay fantasy filmed with my dripping Dommy strap Dick. This video features #Feminization, #Sissy #Slut #Training, #Goddess #Worship, #Cock #Sucking #Training and A little twist on #Fetish #Cross #Dressing. This is only the beginning. #JustLikeDommy

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Ryley Rails Cumshot Compilation Vol 9 video from Ryley Rails

Ryley Rails Cumshot Compilation Vol 9 by Ryley Rails Wanna see me cum multiple times?! I shoot 5 big loads of cum in this newest cumshot compilation vol. 9! I finger my ass, edge, and stroke my sissy cock until it shoots big loads of cum all over myself!

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Convince Us You're a Girl - POV Pegging video from Kim And Vivi

Convince Us You're a Girl - POV Pegging by Kim And Vivi You wake up in a fiery underworld, surely this must be a mistake, but the Demon Queen disagrees. "All Boys got to Hell." Since you're so scared, she offers you a deal, already stroking her massive cock. If your dick is bigger than hers, you can jerk off, and eat your own cum. But if yours falls short... she'll be facefucking you until you swallow her load. When you reveal your pathetic dick she mocks and humiliates you until suddenly an angel appears. Your dick is so small, she mistakes you for a girl! And all girls go to heaven. The angel turns to you, her voice dripping with pity, "Poor thing, if you can convince us you're a girl I'll bring you up to heaven with me. But first, you must undergo a test of femininity." You'll do everything a good girl would do, from drinking your demon master's cum, to begging for your pussy to be fucked. By the time you get to heave, the angel is so convinced, she fucks your pussy, just like you wanted

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Your Cumming Out Party video from Meganluv69

Your Cumming Out Party by Meganluv69 I am here to help you transition and wank to gay porn. You know deep down that is what you truly want. I am here to cheer you on. Fucking Faggot.

^$8.00 Add to Cart

Extreme Sissy Training - Cross Dressing and POV Pegging - Part 2 video from Stella Von Savage

Extreme Sissy Training - Cross Dressing and POV Pegging - Part 2 by Stella Von Savage Part 2 of my POV Extreme Sissy Training Series: Back for more, my little sissy in training! Today we'll be dressing in another pink lingerie set I've picked out for you. You'll be getting into the most humiliating, sissifying positions: face down ass up, batting your eyes, spreading your cheeks, and your sissy pussy will be puckering for my big cock deep in your ass! You'll be taking my dick like a pro and preparing to be my sissy slut.

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Womanlike video from Adria Nite

Womanlike by Adria Nite You broke up with your girlfriend and she’s getting you a reaction you didn’t expect. You hoped you would just forget about each other and move on. However, your girlfriend is furious about all the years of her life that went to waste and all the effort she’s put in trying to save your relationship. The rage you’ve caused has unlocked her magical powers you had no idea about. She’s waving her hands in the air casting spells that break everything in the room. You try to calm her down but it’s too late. She reveals that her power will grow as she sucks all of your male essence out of you. You don’t understand what that means and you want her to stop but that’s when she tells you that you will be transformed into a woman. She starts draining your essence and the whole room shakes. Your voice suddenly becomes higher pitched. She proceeds to alter your silhouette, your face and hair and puts makeup on your face. She leaves the best part - your dick - for last. You beg her not to touch it - you can be a woman with a cock - but she doesn’t listen. You deserve a full transformation. She gives you a pink pussy with a tight hole and then a sexy, slightly too slutty, outfit. She’s over the moon with her creation. Seeing your face full of concern, she says that there’s a way out of it. A long, difficult one, but she believes. She decides to change your outfit for now to give you an easier start and fucks your pussy to give you a taste of your new reality. Tags in the video: gender transformation, magic transformation, transformation, transformation fetish, transformation fantasy, magic remote, magic control, man to woman, femdom, domination, female domination, magic fantasy, erotic magic, sissy, sissy fantasy, sissification, sissy training, feminization, effeminate, witch, witchcraft

^$17.00 Add to Cart

Seamless Sissy Slut - Perfectly Pink Pantyhose Punishment video from PaintedRose

Seamless Sissy Slut - Perfectly Pink Pantyhose Punishment by PaintedRose You've been found out wearing my favorite pair of seamless pantyhose. You will be punished for ruining them by wearing them and replacing them! You like wearing them don't you? I can see that you do and now I understand. I should have seen it all along - you're a girl and a very sexy slut too aren't you? Yes you are. Because I said so. You are not in trouble anymore but you must be sissified into Dommy's sissy slut. Play with your clitty wearing my pussy scented hosiery right now - what drippy girl you are. This film features, Satin Panties, Feminization, Sissy Training, Sissy Slut, Sissygasm, Girl-Pussy, Clitty, Boy To Girl Transformation, Light humiliation, Seamless pantyhose, Edging, StepMom Taboo Roleplay, Caught Peeping, Panties, Fullback, Bikini, Strapon sex, Cum Control, Orgasm from fucking femdom fetish kink. #Feminization #Sissy #SissySlut #Sissification #Femdom #MommyDomme #MILF #Taboo #StepMom #Roleplay #Semaless #Pantyhose

^$13.00 Add to Cart

Ryley Gets Face Fucked video from Ryley Rails

Ryley Gets Face Fucked by Ryley Rails I need my face fucked! Please shove your big cock in my mouth and down my throat! Make me gag spitting drooling all over your cock eager for more! Fuck my face until you shoot your load down my throat!

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A YEAR AFTER SHE FOUND YOUR JOURNAL 1080P - ELLIE IDOL video from Ellie Idol

A YEAR AFTER SHE FOUND YOUR JOURNAL 1080P - ELLIE IDOL by Ellie Idol Your counselor has invited you over for another private session, and you were instructed to let yourself in. From her bedroom door, you can hear her having sex with her man while you wait patiently. She comes out looking a little disheveled but satisfied. Can you believe it's been an entire year of you being pussy-free? No dating, no fucking, only rubbing your clitty, well this is what's best for the women of planet earth! Leave the sex for REAL men, like Ellie's man. He's got the talent and the equipment! She's so proud of her work with you, and although you're paying her for your sessions, it truly feels like charity work for the rest of the world. There is only rubbing your clit if you want to cum, no intercourse, and what better time to do it than at therapy? Slip your girly lil panties on and get ready for some pleasure! The two of you are going to rub one out together. Before you begin, Elle says she suspects you have a secret obsession of big cock. Is that true? The way you talk about the porn you watch gave it away. You LOVE hung dicks! You're not jealous of the men, you're envious of the women!! Perhaps Ellie can help you take the steps you need to be a cock-sucking dick-fucking sissy with a small lil clitoris-penis. The idea of you getting with a guy is pretty hot! She proceeds to tell you about her first experience with a guy who's packing, so listen closely to this size queen and do as she instructs... It's time to explore your gay fantasies by using her story and your imagination!!

^$16.00 Add to Cart

1.5 YEARS AFTER SHE FOUND YOUR JOURNAL 1080P - ELLIE IDOL video from Ellie Idol

1.5 YEARS AFTER SHE FOUND YOUR JOURNAL 1080P - ELLIE IDOL by Ellie Idol It's been a year and a half since your commitment to being pussy-free! Today, you'll have new mantras to recite as you masturbate with Ellie once you strip down naked and get a mirror ready. It's time to fully be in alignment with who you are inside and out! Be sure to watch parts 1, 2, and 3 before you begin this for the FULL experience! Part 5 (the final video in this series) will be released late September, so don't miss the exciting conclusion!

^$15.00 Add to Cart

Beta Sissy BBC Worship Instructions video from SinSpice

Beta Sissy BBC Worship Instructions by SinSpice “Beta Sissy BBC Worship Instructions” - CUSTOM - Buyer Comment: “10 minute video with the BBC dildo. Instructions for beta sissies how to worship BBC and give good oral, exploring the head/shaft/veins/balls/anatomy together.” #beta #sissy #bbc #worship #instructions #custom #clip #sissification #sophiasinclair #mistress #femdom #bisexual #blowjob #dildo #amateur #sinspice #mssinclair #homemade #pregnant #goddess #cocksucker #cravingcock #bigblackcock

^$8.00 Add to Cart

Matching Panties and Titty Clitty - Taboo Sissy video from PaintedRose

Matching Panties and Titty Clitty - Taboo Sissy by PaintedRose I've been waiting for you young lady! Never keep sweet Dommy waiting and especially when I have a surprise for you! Ohhhhh you want to know what it is don't you. Perhaps if you give me a smoochie, I will give you a gift. Yum. It's matching panties and SATIN Flower panties too! You've been such a good girl and deserve a special reward. Try yours on and model them please? Pretty pussy please? Gosh you look so gorgeous - want to have a sissygasm with me? This film features, Satin Panties, Feminization, Sissy Training, Sissy Slut, Sissygasm, Girl-Pussy, Clitty, Boy To Girl Transformation, Light domination, Slut practice, Edging, Step-Mom Taboo Roleplay, Satin, Panties, Fullback, Bikini, Cum Control, Orgasm from step-mommy, good girl. #Sissy #Feminization #MommyDomme #Femdom #Panties #Satin #GoodGirl #POV #Loving #StepMom #Taboo

^$13.00 Add to Cart

Ryley Rails JOI Sissy Training video from Ryley Rails

Ryley Rails JOI Sissy Training by Ryley Rails It's time for more sissy training with Ryley Rails. Get ready to edge your cock and jerk off along while I smack my cock and balls in your face. I tease you until shooting a big load of cum and playing in it! Come on, let's play together!

^$15.00 Add to Cart