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duration 14:16
Step-Mother In Law Takes Charge SIssy Pegging Punishment HD 1080X1920 60fps video from Victoria Lotus
Step-Mother In Law Takes Charge SIssy Pegging Punishment HD 1080X1920 60fps by Victoria Lotus This was a custom video! Feel free to order your very own! Step-Mother in law takes charge You have come to visit your daughter's house and are appalled to see that you sissy step-son in law is not living up to your standards. So as matriarch of the female led ****, it is up to you to set things right. You summon your sissy step-son in law to your room. You make him bend over and pull down his panties and hike up his dress to give him a bare bottom spanking. However his sissy clitty gets hard and you realise that he enjoys it a bit too much. So you decide to change punishment and finger him while he is bent over. This time he cums without your permission and makes you angry. (Main focus of the videos on the pegging portion) Since he likes to cum so much you peg him till he cums again. You comment that he still has a long way to go before he becomes the perfect sissy housewife for your Step-Daughter. You insert a butt plug to remind him to act like a sissy at all times. Camera Angles (Face shown at all times throughout video) Spanking: As if viewer is bent over in front of you. Viewer ass below and out of camera frame so palm can only be seen when raised but not when "connecting" with ass Fingering: Similar angle with hand fingering "below" the camera frame. Angry Pegging: Same as previous video with faster pegging movement. Last 3mins close up of your face with faster pegging movement.
duration 20:39
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
duration 15:51
Pay to Entertain - Star Nine video from Star Nine
Pay to Entertain - Star Nine by Star Nine you want to entertain Mistress Star Nine by doing humiliating slave tasks? I tease you for desiring attention as my crossed legs uncross. you will need your phone for this slave task game by taking blackmail pictures and paying tributes. It's your chance to be a filthy slut for your Findom Goddess. Caressing my nylon legs, I command you to strip but don't get a hard dick because I want to see you tuck that little cock like a mangina. Pull the balls apart and back, cock bending and putting your legs together like a lady. Take those incriminating pictures with your hidden little penis. you want Me to see how well you did hiding your little dick, so pay up like a good pay piggy. Send $100 and then you can email the pic only AFTER you have sent MY money. Dangling high heels off my nylon foot, I explain how my good slaves always have my worn pantyhose on hand. I want you to carefully pull them over your legs. For bonus points, keep that soft cock tucked. Dress up for Me with a pair of stilettos, a bra or a slip and show what a pretty girl you are. you have to pay for Me to see you in your silky nylons. As I'm high heel dangling, it's your cue to get dirty with makeup. Show your Pantyhose Goddess your slutty lips with red lipstick as if you've been giving blowjobs for hours. you need to fill your whore lips with something like a cucumber or a dildo and pretend you're gagging on my nylon feet. Snap a pic and get bonus points for crying! Prove how hard you were sucking and send my money like a good tribute slave. For the final round, think of the dirtiest and most disgusting thing you can do to impress Me. Push your limits to something you don't want anyone to know about and have never done before. Now send. Send your custom video request to star at starbondmedia dot com Includes Goddess Worship, financial domination, sissy training, slave tasks, humiliation KEYWORDS - imposed crossdressing sissification sissy sluts feminization money fetish verbal humiliation tasks female domination pov femdom pov sensual domination submissive/slave training slut training pantyhose domination pantyhose fetish crossed legs fetish dirty talking
duration 17:59
First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play video from Victoria Lotus
First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play by Victoria Lotus Hi there! This was a custom video so feel free to contact me on my profile to get in touch for ordering your very own. Here is the script: "Hey! As discussed via DM, I'd like a custom to guide me into my first crossdressing experience (thong bra, no other feminine clothing involved). In three sections (don't have to be equally long, you judge): shopping for the lingerie, putting it on and wearing it out and about, and JOI/CEI wearing that lingerie in my hotel room. I think the vid will work best if I can play part during each section, then pause it before moving on to the next (e.g. back to my hotel). The context will be: I am going to a conference and feel free to explore my fetish while I'm away, so can go into a lingerie shop and then wear my new purchases and play. The tone should be encouraging/sexy, not humiliating or too femdom (I'm ok being instructed, just not insulted). I don't want to restrict you with a script, so here's just a list of things I like or would like to try: me wearing a non-vibe glass butt plug or a vibrating one (I'll take both, you choose!), clenching my butt with the vibrating plug to stimulate my prostate, gently rubbing my nipples (I really adore edging like this), subtly flashing my lingerie (e.g. bend over to expose a thong in public), self-facial CEI, moaning when I'm turned on, repeating sexy mantras (e.g. "I'm such a cum slut for you"). I dislike: humiliation, pain, insults, being called a sissy. If possible, I'd only want to stroke my cock at the end to push myself over the edge to cum (not throughout the video). As for you, I'd love for you to wear lingerie too, really show me how to put on the bra and thong properly, put in a butt plug with me, and definitely show off your ass frequently as that's a real turn-on for me. My real name is "Shawn" for inclusion in the video. Do contact me via DM if you need more information!" #Crossdressing #Lingerie #FirstTimeCrossdressing #CrossdresserJourney #ThongBraAdventure #ShoppingForLingerie #CrossdressingConfessions #JOI #CEI #CrossdressingInLingerie #Feminization #CrossdressingFantasy #HotelRoomPlay #NaughtyLingerie #SensualCrossdressing #CrossdressingTransformation #CrossdresserLife #ExploringCrossdressing #CrossdressingDiscovery #CrossdressingExperience
duration 18:59
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?
duration 32:39
Puppy Girl Pegs You video from Krissi
Puppy Girl Pegs You by Krissi ✿ Description ✿ Come and play with me, puppy girl! Today, I'm feeling extra playful and I want to take you on a wild adventure. I'll dress up as a bunny, kitty, and of course, a puppy - and I'll even dress you up too! But don't worry, I'll make sure you look absolutely adorable, because I'm going to feminize you and make you my own little pet. Things might get a little messy, though... I have a habit of spitting and drooling all over the place, and I just can't resist doing it all over you too! Don't worry, you'll love it - and you'll even ask for more. But that's not all, my dear pet. I have a few more tricks up my sleeve. Or should I say, up my skirt? Hehe, I'll peg you and make you feel like my own little submissive, and then we'll get really dirty with some ass to mouth action. You'll be begging for more, I promise! So, are you ready to get wild and playful with me? Let's get this party started and see just how dirty we can get! ✿ Notes ✿ Oh boy, I never thought I'd need to do this for a video but this one is MESSY! This video features ✿ Puppy Girl (me) ✿ Feminization (YOU) ✿ Having you eat your own cum ✿ Getting pegged, and having ass to mouth done to you ✿ Dressing you up ✿ ASMR ✿ I spit and drool CLOSE UP A LOT ✿ A lot of pet play references ✿ Seriously I think this is my cummiest video ever ✿ We use your own cum from my pussy as lube for me to peg you more! This video features and mentions the following themes: TABOO / ROLEPLAY / PUPPY GIRL / PET PLAY / BUNNY GIRL / CAT GIRL / SILLY SLUTS / SUBMISSIVE SLUTS / AHEGAO / PEGGING / FEMINIZATION / COWGIRL / NEKO GIRL / DROOL / SPIT FETISH / NAKE MENTION / ANTHONY / ASS TO MOUTH / DOMINANT FEMALE / GIRLS WITH DICKS / GIRLS WITH PENISES / POV BLOWJOB / VIRTUAL SEX / KRISSI POOKIE
duration 7:15
making you my bf's fucktoy - sissification, anal, imposed bi video from Veggiebabyy
making you my bf's fucktoy - sissification, anal, imposed bi by Veggiebabyy I’m your wife, and I just got called in to work, but my boyfriend and I had a big date night planned tonight! You’re going to have to step in for me, and you don’t get a choice in the matter. Before I head out the door, I give you a quick rundown of how to dress, how to treat him, and all the ways he’s going to make you his submissive little sex doll. First, you’ll need to grab a sexy red dress from my closet, plus some cute lingerie that he can tear off of you later. As for makeup, I want you in pink plumping lip gloss, eyeshadow, and mascara. You’ll start the date by going out to dinner. You’re sure to have plenty of people watching as he parades you around on his arm. After dinner comes the important part. You will serve him. You’ll kneel, remove his shoes, kiss his feet, unzip his pants, and immediately take his cock into your mouth. Suck on his balls. Let him fuck his cock the whole way down your throat. Get his cock nice and wet because he’ll be using your drool as lube to fuck your ass. When he’s ready, he’ll flip you over, face down, ass up on the bed. Spread your ass. Present your hole for my boyfriend. Moan like a whore as he fucks you. I want your cocklet dripping alllll over from how wet he makes you. Be a good little fuckhole for him until he’s ready to pull out of your ass and cum in your mouth. Swallow, slut, and then clean his cock with your mouth. Taste your greedy ass on my boyfriend’s thick cock. Then prepare yourself for round 2. :)
duration 27:27
Sis Helps You Crossdress, Part 2 video from Fiona Dagger
Sis Helps You Crossdress, Part 2 by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera!) It's been a couple of days since your sister accidentally walked in on you trying on a dress, and today she's got you a present! She explains that she was out shopping and there was a a sale on at a lingerie store, and she remembered that you said you wanted to try a garter belt and stockings, so she bought you a full set of bra, panties, garter belt and nude stockings to go with them! She tells you she's really happy that you're enjoying yourself experimenting, and says that she thought you looked so good when you tried on her clothes the other day. She asks if you want her to leave so you can try them on, but you tell her you're fine with her staying - and you suggest that she puts on the other set, which she'd bought for herself, so that the two of you can try your new lingerie together! Your sister seems pleased at your suggestion, and the two of you turn around and face away from each other while you get undressed and put on your new items (though of course, you do take a few sneaky peeks at your sister while she's changing...) Once you're both dressed in your new lingerie your sister helps you fasten the stockings to your garter belt, giggling as she notices how sheer your new panties are, and how visible your cock is! She gives you lots of compliments, saying that she really thinks she's going to have to get any future boyfriends to dress up in girls clothing for her, as she thinks it looks so hot! You're enjoying her admiring your body, and feel your cock starting to get hard as she watches you. Your sister notices it and does her best not to stare, but she can't seem to tear her eyes away.... She realizes that the panties she's wearing are actually crotchless, and tries to hide herself with her hands, but you tell her it's fine! She seems embarrassed but admits that she can feel herself getting wet, and that's very conflicting for her - she shouldn't be getting wet over her own little brother's cock! She says she should probably go, as this is all getting a bit weird - but you convince her to sit down on the bed and calm down, assuring her it's fine. You ask her if she really likes seeing you like this, and she tells you it's really turning her on, and in fact she's been thinking about you dressed up like this ever since the other day... You tell her you think she looks really hot too, and that you don't mind that she's turned on over you - your cock is rock hard for her right now, after all! Your sister shyly asks if you'd let her watch you stroke it; admitting that she's been fantasizing about seeing you stroking your cock whilst wearing panties... You slide your hard into your thong and start slowly jerking your cock as your sister stares, then tell her it's fine if she wants to touch herself too... You notice she's making a puddle of wetness on your bed as she opens her legs, revealing the crotchless part of her panties and her pink, wet pussy peeking through... She starts rubbing her clit shyly as she watches you stroke your cock, with both of you growing more and more confident, and confessing how much it turns you on to see each other like this... She tells you she's getting close, and asks if you really want to see your big sister cum? You tell her you do, and that you'll cum with her as well. She moans at this and tells you she so badly wants to see your cock cumming in those panties, so the two of you keep pleasuring yourself and looking into each others eyes as you make yourself cum really hard! Afterwards, your big sister tells you how much she enjoyed that, and leans in nervously, asking you if you'd like to try kissing her... TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, taboo, bro sis, brother sister, crossdresser, crossdressing encouragement, sissification, sissy, feminization, mutual masturbation, jerk off encouragement, lingerie, fingering
duration 14:17
Your Crossdresser Fantasy video from KSWifey
Your Crossdresser Fantasy by KSWifey "When your neighbor asked, you said yes because you couldn't wait to try on her clothes, but when she surprised you by returning from her trip early...." As an amateur artist, I take a professional approach to my craft and desire to offer the highest quality product possible. I hope you enjoy your experience... XoXo, KS Artist's Profile: Whether this is your first visit or you have returned for more – welcome! It is a pleasure to create erotic art from the comfort of my home and share it with you. As a wife, mom, and MILF, I stay pretty busy, though in the evenings, after the sun sets, it's "lights, camera, action." And while I've created for all kinds of fantasies, I have built a reputation for amateur Cheating Wife, Interracial, Creampie POV, and Taboo roleplay content with my signature ASMR sound! I suppose there is something so hot about a beautiful woman doing someone or something they shouldn't - but after all, isn't that what every dirty man wants – "a lady in the street but a freak in the bed"? That's me. In addition to erotic stories of a FEMDOM Princess having an affair on a hubby with a shrimp dick or a Sister-in-Law with a trimmed pussy hidden beneath her bikini as she fucks with an eager boy's penis, I offer a wildly diverse collection of erotica. Whether you need Strap-On, Boss & Employee, or Toy - I invite you to take a deeper look inside my collection! And yes, in case you are wondering, my cuckold knows what I do at night. It excites me to think of my pet, his cock locked in a chastity device, listening through the door as his bi-sexual Madam aggressively pleasures a younger slut or uses her sex machine to bring herself to a twitching orgasm. You see, I get so creamy over submissive sluts that love grabbing my firm tits and alpha men with massive cocks who are still virgins. Anyway, the Female Supremacy doesn't stop there for my husband because after the 4K turns off, I enjoy licking his asshole and making him tongue my freshly fucked pussy. Trust me, I know all about his enema and nip slip fetish, just like he knows all about my panty fetish. And like you, I also watch Breeding Videos, some of my dirtiest kinks are Tit Worship, Bound, and Lesbian Masturbation. When I close my eyes, I dream about this one party and remember how three PAWG women introduced me to scissoring and ass-eating and how older boys loved to melt ice on my pink nipples - so crazy hot! If you can't tell, I love what I do - but who am I? Well, I'm your ex-girlfriend, best friend's daughter, or lifeguard at the pool in her oh-so-sexy bikini. Will you be my stepdad, handyman, or neighbor? I hope so! Do you crave submission as I command you to provide oral servitude as I make your office domination fantasy real, or do you prefer to dominate me as you make me strip and then watch me riding a dildo? Oh, and while still early, I'm pregnant, and yes, I'm excited for my small titties to get bigger - lactation, anyone? I love squirting my breastmilk out of my pink mommy nipples and making a wet mess! So, in closing, I spend a tremendous amount of time, energy, and creativity on my craft, and should you like what you see and decide to buy a video, please know your support makes a big difference in my life - thank you!
duration 21:02
Mom Caught You Cross Dressing video from Fiona Dagger
Mom Caught You Cross Dressing by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera!) Your mom is supposed to be out at work, so you get a nasty shock when she walks in on you when you're all dressed up in your girly lingerie! She screams in shock and immediately begins demanding to know what you're doing - and when she spots some of her own and your sister's clothing items on your bed she snatches them up and starts yelling at you for stealing them! After a while she calms down slightly and starts intensely quizzing you on why you're doing this and whether it's some of of disgusting fetish thing... She tells you that you look like a stupid little slut, and remarks on how uncomfortable it looks seeing your genitals barely contained by that tiny pair of panties! You end up admitting to your mother that yes, it's a sex thing, and some of these items were a gift from your ex girlfriend, some of them you've bought for yourself... And yes, you're very sorry, but some of them you stole from your mother and sister's wardrobes... Your mother asks if your ex girlfriend liked seeing you like this and you tell her that she did, and that the two of you would have a lot of fun while you were dressed up like this. Your mother then gasps as she spots your growing erection! She starts berating you for being a pervert and enjoying your mother seeing you like this, then asks if you enjoy the humiliation aspect of being dressed so silly and slutty, and having people laugh at you? She reluctantly admits that you do look quite good, in a ridiculous way... You can see her getting flustered, and she goes to leave the room saying she'll leave you to it, but then she stops and turns back around... She shyly asks - since you don't seem to mind people watching, and in fact you say you enjoy it - could she perhaps... see how you pleasure yourself when you're dressed like that? You slowly start stroking your cock in your lacy little knickers, and your mother watches in intense fascination. Soon you notice her subtly fidgeting and rubbing her thighs together, so you suggest to her that she go ahead and touch herself too... She's taken aback but considers it, and decides that since you're doing it, why shouldn't she... She hikes up her skirt and begins playing with herself as she watches you stroke your cock; encouraging you and telling you how good you look, even though it's all so strange... You warn your mother that you're close to cumming, and she panics for a moment trying to work out if she's ready to see her own son cumming, but then she decides to go for it! The two of you keep pleasuring yourselves until you cum together, with your mother watching closely as you spurt cum everywhere! Then she seems to realise what she's just done and begs you not to mention this to anyone, saying you'll both just forget this ever happened - but that you're not to steal any more clothes from her or your sister! TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, taboo, mom son, mother son, mommy son, mommy roleplay, glasses, strict, mutual masturbation, jerk off encouragement, humiliation, cross dressing, sissy sluts, sissification, crossdressing, crossdresser, cross dresser, feminization, gender play
duration 14:47
Cum With Me! Sissy Sexuality Training & Mutual Orgasm Instructions with Goddess Kyaa video from Goddess Kyaa
Cum With Me! Sissy Sexuality Training & Mutual Orgasm Instructions with Goddess Kyaa by Goddess Kyaa Take your sissy sexuality training to the next level with this hot new video. I will get you dressed up like a pretty whore then make you bounce on a big cock while you say slutty mantras for me. Then you will edge yourself to orgasm while watching me buzz my clit with my wand. I will play with my gorgeous DD tits while I tell you exactly how to moan. Make it to the end of my training session and you get to cum with me!With a bonus extra full nude body worship after my orgasm to lock in your total mindfuck. Worship your perfect Sex Goddess, slut! My lingerie is a matching set with a white base and tiny little red hearts. My lips are red and my pretty gold nails with matching jewelry look so pretty! Of course, you can never be me... but you can learn to be the hottest little sissy slut you can be by watching me! Follow my instructions to become MY good whore! Worship my divine pussy and tits as I vibrate my clit to a thigh twitching, toe curling orgasm. Remember, you only get to cum when I cum! Ride that dildo til my pussy is creamy! To complete these instructions you will need a slutty outfit, lingerie with stockings and heels, a fat dildo with a suction cup base and a chair or other surface where you can suction it to be able to ride it. Contains: feminization, masturbation, POV, slut training, anal instruction, dress up, sensual domination, cock tease, lingerie, big tits, milkers, breast worship, pussy worship, pussy pleasure, vibrators, ass worship, ass shaking, humping, feet, foot fetish, legs, ass fetish, humiliation, powerful women, femdom, female domination, Kyaa's Empire, Kyaa Chimera, Goddess Kyaa
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