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Showing 61 - 120 Videos

Sissy Tasks video from BlackxRose92

Sissy Tasks by BlackxRose92 Alright sissy, your task today is simple. You're going to clean all of the floors, then get down on your hands and knees, with a toy inside of you, and you're going to clean every inch by hand. While you're filled up, you're going to be scrubbing away, constantly reminded of what being a submissive sissy feels like. This won't just be housecleaning, although the end result will be sparkling floors that you can lick, because this is a delicious lesson on how to be a horny, submissive, housecleaning sissy fuck slut. At every step of the way, you'll feel yourself becoming even hornier as you give yourself completely to the submissive sissy lifestyle. You'll be spending all day on your hands and knees, ass up, face down, cleaning by hand and available to be fucked at any moment. Every inch you clean, is enough inch deeper into becoming the best, horniest, submissive sissy fuck slut that you can be. The whole time that you're cleaning, I'll be able to see your hole filled and fucked, while you just keep scrubbing away, a desperately plugged and so very horny housekeeping submissive sissy slut.

^$8.00 Add to Cart

Sissy In Trouble video from PaintedRose

Sissy In Trouble by PaintedRose You got caught cutting school and stealing a cute little schoolgirls uniform on camera - don't even try to deny it young lady! Keeping secrets, not being good at school, almost going to jail? Shame on you for not telling Dommy sooner! You'll have to be punished. Marched right down to apologize at the school and then you will be homeschooled by FemDommy Rosie! Show me the outfit NOW young lady! You'll have to start focusing better on your lessons and less on the outfits - you must be taught to make your clitty-gasm the sexy way.. afterall, you're my sissy girl. This film is dedicated to Wolfie for her great ideas and friendship! This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

^$12.00 Add to Cart

Sex Demon Pounds You With Your Own Dick video from InfinityWhore

Sex Demon Pounds You With Your Own Dick by InfinityWhore [This was a custom request] You've been dancing with a gorgeous brunette at a nightclub all night and you really think you might have a chance with her, so you bring her back to your apartment. When you arrive, she appears slightly bemused that you've bought her back and admits that no men have had the balls to do that in quite a while. It quickly becomes obvious that something is seriously wrong when she clicks her fingers and appears completely naked with huge black demon horns protruding from her head. She admits that she's a demon with powers sent from Satan himself to mess with human men just like you. However, she clicks her fingers again, dissolving your clothes too, and starts paying attention to the size of your large cock. Perhaps her being a demon isn't quite as devastating as you thought. She tells you that your cock would make a perfect toy for her to play with. It begins to rise to attention hearing her words. A demon girl wants to fuck you! She crawls towards you and starts to gently play with your cock. She licks and sucks softly on your tip, rolling it through her fingers, and repeats again that this would be perfect for her. You're excited to cum in her mouth. Then, out of nowhere, she starts to mutter some strange words and asks Satan for his powers and your cock pops completely off your body and right into her hand. You're absolutely terrified and beg her to reattach it to your body... that's when she tells you to look down and see what she's replaced it with. You glance down and see that you now have a pussy in the place where your cock used to be. She begins to suck and lick on the new dildo that she's created from your cock. Even though you now have a pussy, you can still feel everything that she's doing to you. She begins to humiliate you as she notices your pussy leaking with wetness from the arousal of what she's doing to your cock. She asks if you'd like her to fill you up with your own cock and laughs at the immorality of human beings when you also murmur yes. She slides your own cock inside your newly formed pussy, wearing it like a strap-on only it's magically attached itself to her. She pounds you hard and deep. It feels so strange to be filled up, but you have to admit that it feels good. You start to moan and enjoy yourself as she fucks your pussy. You can't help yourself. She laughs at you and winds you up for thinking that you'd be doing this to her tonight and now you're taking cock like a pathetic little bitch. Every now and then you ask her to return you back to normal, but she giggles that you don't seem to want your cock back, laying there like a slut and taking it in your pussy. She tells you that she wants to breed you like a bitch in heat. The ultimate emasculation. She fucks your pussy so expertly that you can't help but shudder to orgasm. It feels incredible, much different from your usual male orgasms. But, despite that, you're left feeling embarrassed and helpless. You just want your cock back and to go back to normal. Her attitude changes now from playful and cruel to pure evil. She hurls insults and you and tells you that you should be thanking her for just taking your cock and not turning you into dust. You're useless to her now that she's stolen your member and had her fun. She racks her brains for an idea of what to do with you. She can't leave you as you are as you may tell people who she is and what she's done and she can't risk being found out and unable to do the same thing to other men. Maybe she should turn you into a rat... or even a used condom? No, she has the perfect creature. She snaps her fingers once more and you turn into a cockroach right there on the floor in front of her. She looks down at you with a smile and laughs at the fact that all women will run and scream when they see you now until someone inevitably stomps you to death. She encourages you to scurry away quickly before she does exactly that.

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Size Up Your Plug, Size Down Your Chastity, Sissy Slut! video from MissFreudianSlit

Size Up Your Plug, Size Down Your Chastity, Sissy Slut! by MissFreudianSlit I think we take the first real steps towards on your sissification journey.... you love the feeling of panties and I think you should wear them all the time. However, panties is only the beginning. Let's start training that sissyhole for me. Let's start with a very moderate plug, and work our way up. These aren't where we're stopping, but they're a great start. Especially for a sissy! Look how cute - these pretty jeweled princess plugs are going to look so cute inside you. And as we size up your plug, we're going to start sizing down your chastity cage! The cage you've been wearing has been about acclimating you to wearing a cage and letting you cum with a vibrator.... just like a cute sissy slut should. But now I think we should start making it smaller and smaller, til you're in the smallest one I own! You don't need a bunch of length to jerk your cock, you just need some control and a plug. Be a good slut for me!

^$9.00 Add to Cart

Turning You Into My Girlfriend JOI video from Ashley Aoki

Turning You Into My Girlfriend JOI by Ashley Aoki Custom video. I decide I want you to be my girlfriend, not my boyfriend for the night. I dress you up in matching lingerie and a pretty dress. I tell you to jerk your dick as I teach you how to suck a dick. Non-nude

^$8.00 Add to Cart

Transformed Into Doll & Cucked video from Lettie Lith

Transformed Into Doll & Cucked by Lettie Lith A BTO clip, message to arrange your own | When you can't decide what to wear to the Barbie themed party we're hosting as boyfriend and girlfriend, I suggest a spell I've found which will turn you into a doll. While under the spell you'll feel immense pleasure from being looked at and touched, but will be unable to cum. I'm very excited at the thought of having you as my little doll all night, and promise to turn you back the next day before the spell becomes permanent. However, the next morning I confess I was so horny thinking about the transformation you had undergone, that when a friend started flirting with me it quickly escalated to me fucking him in our bed. I describe the amazing sex and how I had forgotten what it felt like to be treated like a real woman. I also tell you how neglectful you've been as a boyfriend, too focused on us dressing you up in all your cute outfits. I think in order to make everyone happy I'll keep you as my doll and make this guy my new boyfriend. To help you, I use MC to convince you that you've always been an empty headed doll who's only purpose is to love me, your owner, and to be played with.

^$18.00 Add to Cart

sexy redhead Domme pegs her cute caged sissy boyfriend video from Veggiebabyy

sexy redhead Domme pegs her cute caged sissy boyfriend by Veggiebabyy Is there anything cuter than a little sissy boy bent over the couch, tiny cock locked away in chastity, ass in the air just begging to be fucked? I don’t think so. In fact, the only way to make that scene better would be to add one very important thing - a fiery redheaded mommy wielding a big strap-on cock, horny and ready to give that little sissy what she deserves! Watch as I pound away at Layne Love's tight ass from behind while his caged cock drips, til he’s begging for more and eagerly bouncing on my dick like a good little slut

^$16.00 Add to Cart

Dressing Baby Up For Other Men video from Sasha And Baby

Dressing Baby Up For Other Men by Sasha And Baby Sasha has planned an intervention for Baby. Fashion wise, she just isn't cutting it. Nothing she wears is sexy and she would get more dick or even pussy with Sasha's help. We specialize in girl girl customs! What fantasies do you have? No matter how crazy your ideas are, we can probably bring them to life. I'd like to say "we've done it all," but then someone comes up with something new, like a "life jacket bondage fantasy." We did that one too! Great pricing, 24-48 hour delivery. Feel free to message us here or check our website in the watermark of this video.

^$19.00 Add to Cart

Taboo Gender Transformation After Subscription video from Sasha And Baby

Taboo Gender Transformation After Subscription by Sasha And Baby After subscribing to Bebe's content site, the customer feels himself slowly transforms from a man, to a sissy, to a woman. He begins to get wet and horny, he even feels tempted to film right alongside her. We specialize in girl girl customs! What fantasies do you have? No matter how crazy your ideas are, we can probably bring them to life. I'd like to say "we've done it all," but then someone comes up with something new, like a "life jacket bondage fantasy." We did that one too! Great pricing, 24-48 hour delivery. Feel free to message us here or check our website in the watermark of this video.

^$23.00 Add to Cart

Happy Humiliatrix 4 video from Ladyvampira

Happy Humiliatrix 4 by Ladyvampira Is that still considered a small penis or is that already a pussy? Such a pathetic stubby cock is only allowed to wear women's underwear and suck cocks for the dominatrix! The tight slave cunt must also be available and is stretched with the dildos under the guidance of Lady Vampira! The horny latex ass of his FemDom goddess has to shine and is licked to a high gloss by the Sissyslut! But his bitch's mouth is also docilely fucked with the strap-on! / Gilt das noch als Kleiner Penis oder ist das schon eine Muschi? So ein erbärmlicher Stummelschwanz darf nur noch Damenwäsche tragen und für die Domina Schwänze blasen! Die enge Sklavenfotze muss auch verfügbar sein und wird unter Anleitung von Lady Vampira mit den Dildos gedehnt! Der geile Latexarsch seiner FemDom Göttin muss glänzen und wird von der Sissyslut auf Hochglanz geleckt! Doch sein Schlampenmaul wird auch noch mit dem Strap On gefügig gefickt!

^$12.00 Add to Cart

Caught Wearing Wife's Panties Lingerie video from Mrs. Betty Darling

Caught Wearing Wife's Panties Lingerie by Mrs. Betty Darling Your wife walks in and catches you wearing her lingerie. She is shocked and confused and at first teases you about it. She asks if this is what really turns you on. She then has an idea. Why don't you give her a little show and try on some of her panties? She hands you several pairs of them, telling you how to pose while wearing them. Then she has another idea, she's going to masturbate with a pair of her panties and you're going to masturbate while wearing another pair. What do you think about that? She lifts up her dress to reveal no panties and starts to masturbate with them while dirty talking to you about how much it's turning her on to see her husband wear her lingerie.

^$12.00 Add to Cart

Happy Humiliatrix 3 video from Ladyvampira

Happy Humiliatrix 3 by Ladyvampira Mini cock loser had enough exercise and fresh air gardening! But before he goes back to his dungeon, his mistress measures his tiny cock! Is that still considered a small penis or is that already a pussy? Such a stumpy cock has to wear women's underwear and is allowed to swallow divine snot through the funnel gag! His mistress' hot latex ass is part of the tease and denial game, just like the merciless ballbusting in high heels! Open your mouth and swallow ashes, Lady Vampira just wants to smoke a cigarette to humiliate you and you as a human Ashtray will also eat the fag! / Minischwanz Versager hatte genug Ausgang und frische Luft bei der Gartenarbeit! Doch bevor es zurück in seinen Kerker geht, wird sein Minipimmel von der Herrin vermessen! Gilt das noch als Kleiner Penis oder ist das schon eine Muschi? So ein Stummelschwanz muss auch Damenwäsche tragen und darf göttliche Rotze durch den Trichterknebel schlucken! Der geile Latexarsch seiner Herrin gehört zum Tease and Denial Spiel, wie das gnadenlose Ballbusting in High Heels! Maul auf und Asche schlucken, Lady Vampira möchte nur zu deiner Erniedrigung eine Zigarette rauchen und du wirst als Human Ashtray auch die Kippe fressen!

^$9.00 Add to Cart

Greed Binge ((pig transformation) video from Enchantress

Greed Binge ((pig transformation) by Enchantress Food has been used as a tool of manipulation for centuries, whether it’s used for the purpose of restricting, resisting, or denying the absoutely necessary human need for consumption. But what about overeating? What about indulgence? Binging on fattening food, on purpose? This file has been created with the intention to equip you with a special tool. A special tool that you can pull out whenever you’re thinking about me. Whenever you feel inclined to serve me. The tool of immense greed. You serve me through food, through stuffing yourself senseless, and watching your body blimp. You serve me through the aggressive disintegration of your own health, watching your muscles practically evaporate. This file features a special “rapid weight gain” induction, where I completely blimp you to almost an immobile state. Once you’re huge, I have my way with you. Teasing your growing fat body with my descriptive, evil words. Do not proceed if you are not comfortable with the idea of your body turning against you, and extensively binging on high calorie foods. Come on baby, eat up for me. Show me how badly you want it. How badly you want to serve me **Gender neutral pronouns**

^$30.00 Add to Cart

Sissy Pajama Party: Pussy Panties video from PaintedRose

Sissy Pajama Party: Pussy Panties by PaintedRose Step-Mom finds her panties in your bedroom while cleaning and asks you to tell her if you're sniffing them, wearing them, or both. You confess the truth and find out you're in so much trouble.. for wearing old dingy stuff instead of pretty girl panties! The punishment is going to the lingerie boutique immediately for a shopping spree where you must try on pretty satin and lace things. This all leads up to a naughty girl sissy lesbian daughter and Mommy pajama party! Thank you Wolfie for sponsoring this video. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

^$14.00 Add to Cart

STEPSIS HELPS YOU GET FEMININE video from Ellie Idol

STEPSIS HELPS YOU GET FEMININE by Ellie Idol Stepsis Ellie wants to help you. She remembers you saying you didn't feel like a man, more in touch with your feminine side. Growing up with only stepsisters will do that sometimes. Since Ellie is only related by marriage, she wants to help you by giving you some cute lingerie to try on. Brand new items just for YOU!! See how much she cares? She wants to make you feel beautiful. It can be difficult coming out sometimes, and you know your stepsis is always going to be supportive. She even got you a little gift to make you cum like a girl. So, strip down and embrace your inner self! Wholesome goodness.

^$7.00 Add to Cart

Mommy's Slutty Femboy video from Ivy Wild

Mommy's Slutty Femboy by Ivy Wild I see you, through the crack of your bedroom door, playing with yourself, dressed in Mommy's lingerie! You naughty little girl! You are such a slut for Mommy, you want to put a show on for me. Mommy loves talking dirty while you fuck your ass! You need to admit to Mommy your naughty desires...You love cum? You filthy slut...Mommy has just the thing for you...she's saved up ALL the cum from Mommy's big bulls...you want to play with it, don't you?

^$10.00 Add to Cart

Sissy Cuckold By Hairy Goddess video from Marley Magdalene

Sissy Cuckold By Hairy Goddess by Marley Magdalene I have lots of pretty lingerie to dress you up in! I'd love to do your make-up too! First I want you to worship my hairy body, imagine yourself in my body, in a different way! Then I'll put you in my lingerie and have my partner fuck you (dirty talk only) while you eat my pussy!

^$5.00 Add to Cart

Happy Humiliatrix video from Ladyvampira

Happy Humiliatrix by Ladyvampira Slave labor awaits the gardener again, but Lady Vampira doesn't just get her slave out of the dungeon! Until the boots are thoroughly cleaned with the tongue, there is no peeing while gardening! The pink sissy lingerie with a butt plug in the ass is particularly humiliating, while the mistress is having a good time at the pool... / Auf den Gärtner wartet wieder Sklavenarbeit, doch Lady Vampira holt ihren Sklaven nicht einfach nur aus dem Verliess! Bevor die Stiefel nicht gründlich mit der Zunge gereinigt sind, gibts keinen Natursekt bei der Gartenarbeit! Besonders demütigend ist die rosa Sissy Damenwäsche mit Buttplug im Arsch, während die Herrin es sich am Pool gut gehen lässt...

^$14.00 Add to Cart

Mom's Pretty Sissy Girl video from PaintedRose

Mom's Pretty Sissy Girl by PaintedRose Wake up everyday and remember who you are. Who is that? You are Step-Mommy's Pretty Sissy Girl. Repeat these positive affirmations with me - You're a pretty girl.. As much as you're a good girl, you know sometimes you're a teensie weensie bit naughty and Mommy likes our special naughty time to make you feel so special! Is that little pretty clitty swollen? Of course it is.. It's naughty time now pretty girl. This film is 2257 compliant and a solo performed roleplay fantasy.

^$12.00 Add to Cart

Sissy Wife Eats Her Cum Out Of Her Panties video from Clara Dee

Sissy Wife Eats Her Cum Out Of Her Panties by Clara Dee Your wife has a present for you: a new pair of purple panties! She makes you put them on and stroke your clit in them, while she tells you about her new bull. She even snaps and few pictures of you and sneakily sends them to him. Then she makes you ruin your orgasm into your panties, and lick it all up, to practice eating cum, for when you suck the bull's dick. Keywords: JOI, CEI, sissy wife, panty wearing, cum in panties, sissy, sissy JOI, good girl, positive femdom, praise, ruined orgasm, CEI, sissy dress up, daddy, Clara Dee JOI, cuck, cuckold, sissy cuckold, sissy training, edging, pussy reveal, spreading, GFE, wife roleplay, jerk off instructions, sissy femdom, gentle femdom, sissy crossdress, feminization, femdom sissy, femdom JOI, cum eating, orgasm control, girl next door, pretty, small tits, big ass, amateur, pussy,

^$14.00 Add to Cart

The GIMP is cumming twice handsfree while stuck in a vacuum pump while fapping a strapon and collecting cum in vial video from Mary Willows

The GIMP is cumming twice handsfree while stuck in a vacuum pump while fapping a strapon and collecting cum in vial by Mary Willows The GIMP is cumming twice handsfree while stuck in a cock pump with static vacuum. Fapping a strapon keeps me busy while being frustrated until I can't take it any longer. Collecting all my creamy love juice in a 10ml vial. You wanna taste ? ;)

^$10.00 Add to Cart

Sissy CEI Boot Domination video from BlackxRose92

Sissy CEI Boot Domination by BlackxRose92 Are you dressed up and ready to play? It's sissy time. Would you like to put on a pair of shoes and show me what a naughty, nasty slut you can be? You're going to eat your cum for me, every drop. If you squirm, I could just put my long red leather gloved hands on your body and encourage you to eat all of your cum, like a horny fucking sissy slut. Suck it, fuck it, and use my boot heel like a greedy sissy cum whore until you're begging to eat your cum. Show me how eager you are to lick my boots clean while you behave like a horny hole. Put your best sissy hole forwards, and show me how horny you can get when you're making a nasty cum puddle and licking it up.

^$9.00 Add to Cart

You're My Sissy Wife Now - Clara Dee JOI video from Clara Dee

You're My Sissy Wife Now - Clara Dee JOI by Clara Dee Your wife found your lace panties, so you have to confess that you're a sissy. You're relieved to find that she's ok with it. Even into it! She makes you put the panties on, and a little lingerie outfit. She tells you how cute you look, and makes you stroke your sissy clit for her. Since you're such a good little sissy slut, she makes you cum in your hand and lick it all off. It's good practice for when you'll suck a real dick... Keywords: JOI, sissy, sissy JOI, sissy wife, CEI, panty wearing, positive femdom, gentle femdom, praise, GFE, wife, role play, Clara Dee JOI, sissy crossdress, sissy femdom, sissy dress up, feminization, sissification, panties, femdom JOI, cum eating, pretty, cute, girl next door, small tits, big ass, amateur,

^$5.00 Add to Cart

Permanent Sissy Programming video from Lacey Royce

Permanent Sissy Programming by Lacey Royce Do you watch Sissy programming videos but find they don’t *stick* long enough? Do you want to be permanently feminized, not just externally but deep in your subconscious mind? ?Listen with headphones for the best results.? This powerful video features vocal layering, subliminal text and audio, mesmerizing visuals. It contains triggers and suggestions intended to permanently make you more feminine and slutty. Including: Touching yourself, obsession with pink, wearing feminine clothing, vocal changes, viewing your body and body parts as female, sucking cock, eating cum, and playing with your asshole. This video includes intense gender play.

^$25.00 Add to Cart

Sissy's First Breeding video from PaintedRose

Sissy's First Breeding by PaintedRose You are so very close and want to be just like your Step-Mommy-Domme and when she comes to you to tell you that you've been chosen to breed and carry a sissy daughter for her, you know you must do your best for Mommy. Dommy will be by your side every step of the way warming up your sissy pussy for Bull Daddy's taboo fertile seed and getting your womb ready to carry. You belong to Mommy and I am only sharing you with Daddy for the purpose of creating your new little sister. After Dommy pops your cherry, you are placed on all fours facing Mommy for the breeding with her firm but gentle guidance. This video contains feminization, breeding, sissygasm, clitty rub, breeding sissy pussy hole, Panty Sniffing, Bull Cock, Strap On, Dommy Dick. Thank you for this custom film. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you! Sissy Lover Gift of Devotion: DrippyClitty=$10, SissyGasm=$25, Slutty Pussy=$50, Dommy's Slut=$100! Appreciation: SweetSub=$100 SizzlingSub=$500 Super Duper Sub=$1000 TIP + Message to THANK ME for it. You're Welcome Darling.

^$13.00 Add to Cart

GIMP squirting a big hands free load while connected to E-Stim device video from Mary Willows

GIMP squirting a big hands free load while connected to E-Stim device by Mary Willows GIMP squirting a big hands free load while connected to E-Stim device. To watch my favourite porn clips while plugged is one of my biggest hobbies lol. Feeling the horniness build up until I can't take it any longer and need to have a frustrating release.

^$12.00 Add to Cart

11 Bi Slave Gang Bang 6 Fuck Slut video from Ladyvampira

11 Bi Slave Gang Bang 6 Fuck Slut by Ladyvampira Every slave wants to be used and inseminated, so Lady Vampira has the ideal position for it! While a 2-hole mare indulges in the lust of other men in a sling, the rubberdoll underneath can be licked and blown by the sissy slut with rimming and gay blowjobs to a cumshot! Looking at the bi slave gang bang, the TV whore first licks his rosette and then the sperm from his cock, while the mistress stretches and fisting his asshole from behind! Now the blonde sissy bitch is being mercilessly anally fucked by the strict dominatrix! POV Extreme XXL Strap On Pegging! / Jeder Sklave möchte benutzt und besamt werden, daher hat Lady Vampira die ideale Position dafür! Während sich eine 2 Loch Stute im Sling der Lust anderer Männer hingibt, lässt sich die Rubberdoll darunter mit Rimming und Gay Blowjob bis zum Cumshot von der Sissy Slut lecken und blasen! Mit Blick auf das Bi Sklaven Gang Bang leckt die TV Hure ihm erst die Rosette und dann das Sperma vom Schwanz, während ihm die Herrin von hinten das Arschloch dehnt und fistet! Jetzt wird auch die blonde Sissy Bitch von der strengen Domina gnadenlos anal gefickt! POV extremes XXL Strap On Pegging!

^$9.00 Add to Cart

11 Bi Slave Gang Bang 5 Suck Slut video from Ladyvampira

11 Bi Slave Gang Bang 5 Suck Slut by Ladyvampira Every slave wants to be used and inseminated, so Lady Vampira has the ideal position for it! While a 2-hole mare indulges in the lust of other men in a sling, the rubberdoll underneath can be licked and blown by the sissy slut with rimming and gay blowjobs to a cumshot! Looking at the bi slave gang bang, the TV whore first licks his rosette and then the sperm from his cock, while the mistress stretches and fisting his asshole from behind! Now the blonde sissy bitch is being mercilessly anally fucked by the strict dominatrix! POV Extreme XXL Strap On Pegging! / Jeder Sklave möchte benutzt und besamt werden, daher hat Lady Vampira die ideale Position dafür! Während sich eine 2 Loch Stute im Sling der Lust anderer Männer hingibt, lässt sich die Rubberdoll darunter mit Rimming und Gay Blowjob bis zum Cumshot von der Sissy Slut lecken und blasen! Mit Blick auf das Bi Sklaven Gang Bang leckt die TV Hure ihm erst die Rosette und dann das Sperma vom Schwanz, während ihm die Herrin von hinten das Arschloch dehnt und fistet! Jetzt wird auch die blonde Sissy Bitch von der strengen Domina gnadenlos anal gefickt! POV extremes XXL Strap On Pegging!

^$9.00 Add to Cart

One of my longest handsfree sissygasm in chastity (can't stop leaking) video from Mary Willows

One of my longest handsfree sissygasm in chastity (can't stop leaking) by Mary Willows One of my longest handsfree orgasm in chastity (can't stop leaking).

^$10.00 Add to Cart

Double ruined handsfree orgasm video from Mary Willows

Double ruined handsfree orgasm by Mary Willows Double handsfree orgasm while I just wear my tight silver cock ring. I am always near to explode while watching my favourite porn clips. Since I am sitting on a butt plug it's a constant pressure on my G-Spot until my wet cock explodes.

^$12.00 Add to Cart

MommyDomme's Sissy Lesbian Lover Training video from PaintedRose

MommyDomme's Sissy Lesbian Lover Training by PaintedRose It's really strange that my lingerie company sent me a maid's uniform by mistake, isn't it Son? I am not so sure it was a mistake because I've noticed some things going on with your behavior lately. You're going to try this on for me, it just happens to be YOUR SIZE! I will be punishing you in all sorts of ways for lying to Mommy. You will clean on your hands and knees in this maid's uniform and when you finish all of the chores, you will begin your training to be my Sissy Lesbian Lover! First things first, you'll wear this clitty cage so that you stay focused while you you do your Cinderella chores. Feminization training for a sissy slut begins with a Dommy Dick Sucking Lesson on your knees young lady. POV, Oral, Strap-On Sex and more surprises! Thank you to Wolfie for sponsoring this very Dommy Film. Rosie's Thank You Gift: Serve Dommy. Sweet Girl= $5, Nice Girl=$10, $25=Good Girl, $50=Very Good Girl, $100=Mommy's Favorite Girl Submissive Servitude DrippyClitty=$10, SissyGasm=$25, Slutty Pussy=$50, Dommy's Slut=$100! TIP + Message to THANK ME for it.

^$15.00 Add to Cart

SISSIFIED TO EARN MONEY FOR THE IDOL YOU LOVE video from Ellie Idol

SISSIFIED TO EARN MONEY FOR THE IDOL YOU LOVE by Ellie Idol Ellie is the one you adore, your absolute favorite. You love her...and she plans to BREAK you. She's going to mold you into her perfect money making sissy cam slut! She's about to give your life meaning. You'll need dick sucking training, so grab your dildo! Also, you'll need to improve your looks and have a feminine appearance so you'll be getting permanent makeup. You've already got that tiny little clitty hanging between your legs. You'll be edging but your orgasm will be ruined and you'll have to eat your cum load by slurping it off that dildo you've been sucking. Oh, and you'll pay dearly for the privilege.

^$16.00 Add to Cart

Handsfree sissygasm in chastity while fapping Strapon video from Mary Willows

Handsfree sissygasm in chastity while fapping Strapon by Mary Willows Being locked usually makes me very inventive. Fapping a strapon keeps me busy while I'm swollen and frustrated. My mind says that I'm masturbating but I feel nothing :( Being locked just means that I have to cum in a different way ;)

^$12.00 Add to Cart

Sissy Slut Faggot Toy For Mommy and Her Big Black Bull video from PaintedRose

Sissy Slut Faggot Toy For Mommy and Her Big Black Bull by PaintedRose Sissy Slut Faggot Toy For Mommy and Her Big Black Bull. You hear loud noises and thumping coming from Mommy's (Step) bedroom and you go to check on her. You see a naked man kissing Mommy, a big black man, and she is kissing him too. You' are staring at his big dark colored penis going in and out of Mommy's private place and... then Mom Sees you watching and get's upset with you. She notices your tiny little pointer and laughs at you. She tells you you're a sissy slut and that you're Mommy and New Bull Daddy's Fuck Toy. Then comes the good part.. Thank you for this custom Audio Story.

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Sissygasm in chastity while riding my butt plug video from Mary Willows

Sissygasm in chastity while riding my butt plug by Mary Willows Sissygasm in chastity while riding my butt plug

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Mary Willows GIMP handsfree E-Stim Orgasm video from Mary Willows

Mary Willows GIMP handsfree E-Stim Orgasm by Mary Willows My alter ego, the GIMP, is connected to e-stim device and watches his favourite porn movies until he can't take it any longer and needs to squirt ;)

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ENCOURAGING MY SEXY SISSY HUSBAND video from Ellie Idol

ENCOURAGING MY SEXY SISSY HUSBAND by Ellie Idol Ellie has a confession now that you're sitting in front of her. She's aware of what you're hiding...that you're a closet sissy. You've got so much sissification porn on your computer and she's a little hurt that you kept this secret. Not because she doesn't approve but because you lost out on so many great experiences with her. You both could have been having fun this whole time!! She requests you open the box sitting next to you which contains a cute outfit for you to wear. Stockings, bra, panties...even a gorgeous wig! You get dressed up and show your true self. She's such a supportive wife... she even shares some prior experiences with exes that will leave you feeling more sure she's the one. You're getting excited down below and after wifey Ellie gives you some lipgloss, she instructs you to masturbate. Touch your clitty for her! She's turned on seeing her sissy spouse. You'll never have to be shy around her. Ever. There's something so hot about being allowed to be your true self. Ellie darling just wants you to have a very nice coming out time with her... A true bonding experience.

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Sissy Bra Slut: Clitty Cunt Fucking video from PaintedRose

Sissy Bra Slut: Clitty Cunt Fucking by PaintedRose You arrive to see Mistress Dommy and you know she is wearing your favorite bra as she loosens her blouse staring you in your eager eyes. You're aching to be put out of your misery and your Dommy lets you get grabby like a mind fucked little cumslut. She immediately makes you jerk your sissy clit into the bra cups and puts it back on while berating your pathetic need to use her favorite bra as a cumrag. You're hard clitty is begging to be used like the frisky sex toy you are. Fuck my perfect pink pussy with your stiff clitty you cunt fucking sissy whore. Your Dommy loves letting you misbehave so you can then be punished. What have you done? You want pictures of your little bitch cum dripping down my legs? You will be punished for this and you will buy your Mistress new pretty things and thank me for it. This film includes; Sissy training, Mind Fuck, Clit Fucking, Cum Drip, Bra Fetish, sissy slut, Femdom, Findom, humiliation. Thank you for this Custom Video. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you! Rosie's Extra Humiliation Tax: Leaky Loser=$10, Jerkaholic=$25, Pussy Free=$50, Chastity=$100! TIP + Message to THANK ME for it.

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Plushie Humping Pervert video from Deity Kinky

Plushie Humping Pervert by Deity Kinky Look, I know its been a while since I let you rub one out. You've been so patient since I asked you to wear that cage and I think it's time you get the chance to cum. Oh, you don't have to worry about taking your cage off either. Also, you'll need this plushie.

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Sissy Girls Get Curls video from PaintedRose

Sissy Girls Get Curls by PaintedRose You arrive at Step-Mom's house after being kicked out by your girlfriend for trying to be manly. I guess it's time for discipline and training. You're so weak for Feminine training with MommyDomme but lack the confidence to be your true self in front of your girlfriend. Mommy now owns your balls and says that you will give your masculinity to her as you are transformed into the ultimate service sissy girl. You;'ll begin your training right now as you weaken from Mommy's lingerie, curls, and her FemDominance over you and your sissy bitch needs. You need girl training, discipline, and fucking sissygasm for servitude. Thank you for this custom video. This film is 2257 compliant and a solo performed roleplay fantasy.

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You Dont Deserve Cunt only Meaty Cock video from Paislee

You Dont Deserve Cunt only Meaty Cock by Paislee I hope you enjoy, check out all my vids

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11. Bi Slave Gang Bang 2 - Showing the sissy whore video from Ladyvampira

11. Bi Slave Gang Bang 2 - Showing the sissy whore by Ladyvampira The sissy whore is shown to the men on a leash with a collar and has to suck every cock hard! Fucking has to be earned, the mistress commands and educates the cock girl together with the rubber doll to become a cock horny whore! The slut has to orally satisfy every guy on her knees, but the sissymaid also has to jerk off with her hands! Dominatrix Lady Vampira lets her whip dance on all slaves and uses the dildo to ensure hot group sex! / Die Sissyhure wird den Männern an der Leine mit Halsband vorgeführt und muss jeden Schwanz hart blasen! Ficken muss man sich verdienen befielt die Herrin und erzieht das Schwanzmädchen zusammen mit der Rubberdoll zur Schwanzgeilen Blasnutte! Auf Knien muss die Schlampe jeden Kerl oral befriedigen, doch mit den Händen muss die Sissymaid auch schön wichsen! Dabei lässt Domina Lady Vampira ihre Gerte auf allen Sklaven tanzen und sorgt mit dem Dildo für geilen Gruppensex!

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11. Bi Slave Gang Bang 1 - Showing the sissy whore video from Ladyvampira

11. Bi Slave Gang Bang 1 - Showing the sissy whore by Ladyvampira The sissy whore is shown to the men on a leash with a collar and has to suck every cock hard! Fucking has to be earned, the mistress commands and educates the cock girl together with the rubber doll to become a cock horny whore! The slut has to orally satisfy every guy on her knees, but the sissymaid also has to jerk off with her hands! Dominatrix Lady Vampira lets her whip dance on all slaves and uses the dildo to ensure hot group sex! / Die Sissyhure wird den Männern an der Leine mit Halsband vorgeführt und muss jeden Schwanz hart blasen! Ficken muss man sich verdienen befielt die Herrin und erzieht das Schwanzmädchen zusammen mit der Rubberdoll zur Schwanzgeilen Blasnutte! Auf Knien muss die Schlampe jeden Kerl oral befriedigen, doch mit den Händen muss die Sissymaid auch schön wichsen! Dabei lässt Domina Lady Vampira ihre Gerte auf allen Sklaven tanzen und sorgt mit dem Dildo für geilen Gruppensex!

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Sissy Cuck Maid: MommyDomme and Bully video from PaintedRose

Sissy Cuck Maid: MommyDomme and Bully by PaintedRose Since Step-Mommy got divorced she acts very confident and bold. She dresses different and has been going on lots of dates. She tells you that she has a new boyfriend and to your surprise, it's your bully! MommyDomme doesn't believe he could ever be a bully because he's so sweet, loving, and takes such good care of all her needs. One day, you're invited into their bedroom and given a costume and a .. pink.. "cock cage". You're ordered to put it on by Mom as she is fucking her boyfriend - the mean bully! Step-Mom degrades and humiliates you for not being man of the house and only suitable for house chores, and sissy cuckold clean up slave duties. This is only the beginning of your new servitude role for Mommy and "Daddy".

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Beta Chip Sissy Chastity Training video from Miss Ivy Ophelia

Beta Chip Sissy Chastity Training by Miss Ivy Ophelia This video is intentionally CENSORED for betas! This censorship is all part of your beta training * You're such a good reprogrammed sissy for Miss Ivy. This drool gag trains your mind to be an obedient girl for Me. It will make you spit and slobber all down your face through these holes. You'll feel so submissive, that's My good girl. Open up and Miss Ivy will take over. Let's tuck you into a pretty matching chastity cage. All gagged, programmed and locked up like My good femme bimbo! Let's tuck your clitty away and tease you. Now your sissy beta chip is kicking in, and only pixelated censorship remains. These pixels will condition you even deeper into your beta submission. Your brain is rewired, no more pussy for you.

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Dont Count Christie Out! Christie Ricci vs Collin Morris video from WORLD WIDE MIXED WRESTLING

Dont Count Christie Out! Christie Ricci vs Collin Morris by WORLD WIDE MIXED WRESTLING Collin Morris, who weighs 300lb, takes on Christie Ricci, who weighs just 145lb. Christie is undefeated, and puts that streak on the line by accepting Collin's challenge. Is Christie insane, or will she shock the world and prove that she is the greatest female wrestler of all time! This is another classic video from World Wide Mixed Wrestling!

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BRITISH INVASION - Janelle Sinclaire vs Scott Colton video from WORLD WIDE MIXED WRESTLING

BRITISH INVASION - Janelle Sinclaire vs Scott Colton by WORLD WIDE MIXED WRESTLING Scott Colton came all the way from jolly old England to wrestle the ultra sexy female wrestler Janelle Sinclaire in a best of 3! This is another classic video from World Wide Mixed Wrestling!

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THE HUNG STUD IS A SECRET SISSY video from Ellie Idol

THE HUNG STUD IS A SECRET SISSY by Ellie Idol You're an absolute stud of a man. Not only are you tall, handsome, and well-built...but you've got a GIANT cock! Women are constantly throwing themselves at you but little do they know, you're a sissy! Ellie is here to have some fun with you by dressing you up and giving you her strap-on dildo, which surprisingly is smaller than your massive dick! Ellie goes to town on your holes while letting you in on her exciting new plans to use you for fun!!

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Sleeper in the Summer Rain - Summer Rains vs Horsepower video from WORLD WIDE MIXED WRESTLING

Sleeper in the Summer Rain - Summer Rains vs Horsepower by WORLD WIDE MIXED WRESTLING Summer Rains challenges Horsepower to a best of 5 Sleeper match. Horsepower, who thinks Sleepers are for sissies, eventually accepts, given that he has a serious grudge with the sexy yet technically talented pro, Summer. After watching this match, you are certain to become a Summer Rains fan! This is another classic video from World Wide Mixed Wrestling!

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Cuckold For Femdom Wife Life video from BlackxRose92

Cuckold For Femdom Wife Life by BlackxRose92 Viewer's Husband That Has Returned From Sissy Boot Camp Attire: Please wear lingerie as this will take place right before you spend the rest of night getting fucked Instructions: The viewer has just returned home from Sissy Boot Camp and you tell him that he looks well trained. Go over the husband's new routine and expectations as a sissy husband. He's to be in chastity at all times, including at work. He will also be required to wear a buttplug. You already made arrangements at his job to direct deposit his entire paycheck into your bank account and his lunch breaks will be spent giving his alpha male boss a blow job so that he can remain employed. You remind him of the previous rules that you set in the first video, such as banning him from the bedroom, he's banished to the spare room, he's to wear skimpy sissy outfits that you will pick for him to wear on a daily basis and he's to switch into them immediately after coming home and showering. You tell him that dinner is to be promptly made within an hour of the viewer getting home for you and any bull or stallion you have coming over to fuck you that evening. Afterwards, he is to come into the bedroom and get you prepped for your pounding; he will also be on clean up duty as well. Tell the viewer that there will be no backtalking, telling you no, or resisting. While you are getting fucked, the viewer is not allowed to wear headphones and he must listen to all of your moans and noises while he performs his sissy duties around the house. You will end the video by saying that your alpha is already here ready to ravage your pussy so he is to come in the bedroom right now to get you prepped for "tonight's festivities". Something to that effect

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The Property 3 video from Ladyvampira

The Property 3 by Ladyvampira Property is kept in a cage and ignored. But it has to practice again to be feminine and fuckable for other ladies and clients! The day toilet can watch through the open doors as the slave crawls out of the cage at my feet, cock in his mouth. Sucking toes, blowing a dildo, licking feet, the slave cunt has to be able to do all of that! The slut is not spared verbal humiliation, because the pink lingerie is not embarrassing enough! He'll take off his knickers and stuff his mouth with them to sit on the rubber cock and ride it as the mistress commands! But instead of deflowering his whore's ass as ordered, the fat pig prefers to provoke a punishment! The whiplashes almost make him cry and then Lady Vampira smashes his useless balls to a pulp with barefoot ballbusting! / Das Eigentum wird im Käfig gehalten und nicht weiter beachtet. Doch es muss wieder üben, für andere Damen und Freier feminin und fickbar zu sein! Die Tagestoilette kann durch die offenen Türen dabei zusehen wie der Sklave aus dem Käfig kriecht, zu meinen Füßen, mit dem Schwanz im Maul. Zehen lutschen, Dildo blasen, Füße lecken, all das muss die Sklavenfotze können! Verbale Demütigung bleibt der Schlampe auch nicht erspart, denn die rosa Damenwäsche ist noch nicht peinlich genug! Er wird seinen Schlüpfer ausziehen und sich das Maul damit stopfen, um sich auf den Gummischwanz zu setzen und ihn abzureiten, so wie es die Herrin befielt! Doch statt seinen Nuttenarsch wie befohlen zu entjungfern, provoziert die fette Sau lieber eine Strafe! Die Peitschenschläge bringen ihn fast zum weinen und dann matscht Lady Vampira seine nutzlosen Eier mit Barfuss Ballbusting zu Brei!

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BLACK KHARMA - Kharma vs Poker video from WORLD WIDE MIXED WRESTLING

BLACK KHARMA - Kharma vs Poker by WORLD WIDE MIXED WRESTLING What happens when you have an overconfident and skilled BLACK male pro wrestler fight an overconfident and skilled WHITE female pro wrestler in the squared circle? BLACK KHARMA! Enjoy this spectacular back and forth mixed pro wrestling match filled with a wide range of spectacular pro moves and an exciting ending! Both of these wrestlers were flown in to the World Wide Mixed Wrestling Studios for this match! As a special stipulation, Kharma insisted that she wrestle in a bikini and barefoot! This is a must have video for pro mixed wrestling enthusiasts!

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MALE DESTRUCTION, BRIT STYLE - Goldie vs Female Destroyer video from WORLD WIDE MIXED WRESTLING

MALE DESTRUCTION, BRIT STYLE - Goldie vs Female Destroyer by WORLD WIDE MIXED WRESTLING Goldie comes into the ring insulting the Female Destroyer. She recently defeated him, and now he wants a rematch. He proposes a Best of 5 that Goldie accepts. Will Goldie humiliate the Female Destroyer again? This is another classic video from World Wide Mixed Wrestling!

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Husband's Bimbofication video from MissMilaRose

Husband's Bimbofication by MissMilaRose Your wife has been promoted and is now leading a bimbofication project... but she needs a volunteer. You! Get ready to be transformed into a complete BIMBO!! *** STUDIO PRODUCTION *** Tags: MissMilaRose, Mila Rose, Girl Next Door, Petite, All Natural, Brunette, Bimbofication, Feminization, Sissification, POV, Dirty Talk, Roleplay, Non Nude, Amateur

^$24.00 Add to Cart

Your First Anal Dildo Sissy Task video from Marigoddess

Your First Anal Dildo Sissy Task by Marigoddess I've been training you to be a good slutty sissy for Me. I think you're finally ready for your very first sissy anal dildo. I'm upgrading you from a butt plug to a dildo, but don't get ahead of yourself. I know you fantasize about big huge rock hard cock exploring your depths, however I want you to be realistic. A pretty girly pink average sized dildo is the practical purchase you'll be making for Me. Sure you could shop online for a new sex toy, but it will be so much more risky, thrilling, and adrenaline-inducing to do so in-person at an adult boutique. Be a good sissy and complete My slutty task. Follow My instructions, and be sure to snap a few pictures as proof of your bravery and obedience.

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Step-Mommy Does Your Makeup - POV BJ video from Lettie Lith

Step-Mommy Does Your Makeup - POV BJ by Lettie Lith You're sat watching Step-Mommy do her makeup when she tells you she's noticed how much you like doing that. She offers to do your makeup, gently talking you through her makeover of you, applying plenty of pretty pink eyeshadow and lip gloss. When she's done, Step-Mommy realises how excited you've become and tells you that you deserve a reward for being such a good babydoll, letting her turn you into her pretty girl. She tells you to lie back and relax, taking your hard cock in her mouth. Step-Mommy tells you what a good girl you are, taking you deep into her throat and telling you to cum in her mouth.

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My Roommate Is A Secret Cockstealer video from Lacey Royce

My Roommate Is A Secret Cockstealer by Lacey Royce Lacey arrives home gleefully holding her latest trophy. She is admiring it, when she realizes her roommate Scarlet is masturbating on the living room couch. Instead of leaving, she immediately starts asking questions. She wants to know what is on the laptop that her roommate is looking at. When she finally gets a peek.. she's surprised to find Penectomy porn! Of course, she's surprised, because she's fairly sure that no one knows her secret. She digs further and asks if her roommate has heard the news story about the woman. Turns out, Scarlet has the news story up and has been reading it while she masturbated! Lacey decides this is her moment and begins asking lots of questions about chopping off her cock for real. She teases, getting more and more worked up talking about actually going through with it. Lacey reveals her secret.. her last trophy, the last cock she took from some helpless man. She promises that she wouldn't do anything without her roommate's permission, she only steals the cocks of strangers. But if Scarlet wants to consent.. she would be happy to oblige. Lacey pulls out her cock, and examines it, touching it and talking more about what it would really mean to give up her cock. She explains she makes dildos out of them, and what an honor that would be to have her cock become a toy for pleasure. They make a bargain. Lacey agrees to give her roommate one last night of pleasure and the biggest orgasm ever and then in return, after that, she must surrender her cock. Things move to the bedroom. Lacey slowly seduces, the last trophy lying on the bed as she strips, sucks, and teases Scarlet's hard cock, including a long tit job before climbing on top and riding until Scarlet can't hold back anymore and has to cum. Then it's done, it's too late for regrets. Lacey will exact her end of the bargain. With surgical precision, she slowly separates the cock from the balls and removes it. All while her roommate watches, fully awake and aware. *Notes - This video was a very special custom. It uses female pronouns for the POV roommate, named Scarlet. All penectomy fans will enjoy this video but it may have extra appeal for anyone who uses female pronouns and fantasizes about penectomy.

^$25.00 Add to Cart

Step-Mom's Bully Cuck Cum Slave video from PaintedRose

Step-Mom's Bully Cuck Cum Slave by PaintedRose You arrive home to find Step-Mom Fucking One of your bully friends - not just one but all of them. How could she? Ohhhh - maybe that's why they stopped picking on you. You're informed that she's been taking bully creampies for weeks and has come to resent you for it so much that she knows now that you deserve to be bullied and humiliated. Here is your loser lesson! Your other buddy is recording this big dick orgy for everyone to see when Step-Mom tells you how she's been making your girlfriend eat their creampies out of her pussy while Step-Dad fucks her tight pussy with no condom. We are getting impregnated tonight by bully cum while you watch us take load after load to the mouth, tits, and pussy while we verbally degrade you for the loser you are. Your girlfriend is my bitch and so are you now as I tell Step-Dad to spit in your butthole before he fucks it to break you in the easy way. Don't worry - he's not as big as your friends. Keep eating load after load of big bull dick drippy cum loads. Filthy endings are perfect for the ultimate humiliation - Fuck You Loser. Thank you for this custom film.

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Under FemDom Control 1 video from Ladyvampira

Under FemDom Control 1 by Ladyvampira Your nipples are like femdom control knobs that a dominatrix simply knows how to master! Kneeling under me, I sit sublimely on you, but then I want to control your lust and then I have to stuff your mouth with the funnel again! The hourglass stands in the way of your whining, because that's how long you'll endure my anal games and drink my pee as a reward! / Deine Nippel sind wie sind wie FemDom Control Knöpfe, die eine Domina einfach zu beherrschen weiss! Kniend unter mir, sitze ich erhaben auf dir, doch dann will ich deine Lust kontrollieren und schon muss ich dir wieder das Maul mit dem Trichter stopfen! Deinem Jammern entgegen steht die Sanduhr, denn solange wirst du meine Analspiele ertragen und zur Belohnung meinen Natursekt trinken!

^$14.00 Add to Cart

COMING OUT AS TRANS TO YOUR BEST FRIEND video from Ellie Idol

COMING OUT AS TRANS TO YOUR BEST FRIEND by Ellie Idol You sit your best friend Ellie down for very important news: you're coming out to her as trans! Ellie always felt you were feminine and even feels this could bring your friendship to a newer level of closeness. You're one of the girls after all! She suggests trying out new outfits to match your inside better. What safer place to do it than here? She wants to help you discover your true self and embrace your new life with comfort and confidence. You'll only find LOVE and SUPPORT here.

^$7.00 Add to Cart