Category: Cuckolding

  • Tell Me What You Did To Him (Episode 7 of Sissy Cuckold Contest)

    Tell Me What You Did To Him (Episode 7 of Sissy Cuckold Contest)

    How’s it going girl. I’ve been busy working on our little project, hahahaha. How’s your boyfriend doing with the cuckolding on your end. Oh my god really???? That so funny… oh girl, I’m gonna have to start playing with myself as you give me all the details. He’s there now… cleaning… in a French maid outfit??? Hahahaha! Mmmm, um gonna have MY EX send My Slave home with sore balls after cleaning. I’ll have a super ridiculous maid outfit here waiting for him, mmmm. It’s gonna be all he wears from now on! Mmmm, fuck this is gonna make me cum… keep laughing… keep laughing… I'm gonna cum! Astrid Star

    Duration: 5 min | Price: $17.99

    You will be redirected to complete your purchase.

  • Make Up To Serve Us (Episode 6 of Sissy Cuckold Contest)

    Make Up To Serve Us (Episode 6 of Sissy Cuckold Contest)

    Good news wimp, I showed my ex your little cum eating video and he agreed to add a new humiliation task to your cuckold duties. We laughed and laughed about it, he's such a man for being so mean to you… sorry but I couldn't help it, he was fucking my pussy so good and I knew if he kept talking about the cruel stuff he was gonna do to you, it would make me cum so fuckin' hard! I'm gonna have to do your makeup. Yes… makeup. He doesn't want some manly man goin over there to clean… your gonna have to look wimpy, ya know… metro sexual or whatever… so come here. (Wink) You look just precious! I'll tell him your on your way to the store for cleaning supplies. He'll text you if he wants you to pick him up a six pack or anything, hahahaha. Bye pretty boy. Astrid Star

    Duration: 7 min | Price: $17.99

    You will be redirected to complete your purchase.

  • Paycheck Pounding Party (Humilfication Day Episode 6)

    Paycheck Pounding Party (Humilfication Day Episode 6)

    See the full 2 hour video here: Humilification Day (Full Season 1) … Perfect if you're already t**** in a chastity cage! This is the sixth day on this parody of Groundhog Day. I found a folder called “pay pig poundings”! Yea… I found it quite interesting. It seems some deranged loser made a ton of image captions and they all have sexy girls that are pegging a wimp in chastity… and then it dawned on me… you wrote them! You did, didn't you? I'll either let you keep your pants on and let you beg for mercy… or I'll let you take your pants off and stroke your beta boy cock while you beg to be my “pegging party pay pig”! So what's it gonna be, loser? This is about your financial destruction, your asshole destruction and the destruction of any hope you might have had of stroking your cock like a “real man” again. The most you'll ever get, is the chance to jiggle your cage while my strap-on pounds your girly asshole. Oh and that's after you hand me your full paycheck on your knees! No check… no poundings! And you will need poundings, beta boy. You'll crave them… you'll beg for me to pound your fag hole just to drip a few precious drop of precum out of your blue balls. Their almost here, cuckie. Time to apply the ice and shrink you down size and get this steel chastity cage on you. I want all my hot girl friends to come in and see you caged and standing in the corner with your back arched and ass presented for destruction. Hahahaha. Aiden Ashley

    Duration: 14 min | Price: $17.99

    You will be redirected to complete your purchase.

  • Castrated Cuck Conclusion (Humilfication Day Episode 8)

    Castrated Cuck Conclusion (Humilfication Day Episode 8)

    See the full 2 hour video here: Humilification Day (Full Season 1) … Perfect if you're already t**** in a chastity cage! This is the eighth day on this parody of Groundhog Day. I'm on your computer where you keep all your chastity porn??? Hahahaha. I have enough information to blackmail the fuck out of you??? Hahahaha. You're fate is clearly up to me. I really find this all very amusing. Stimulating and amusing. Ohhhh and then I found your folder called “Castrated Cucks” ! Now that was hot! I gotta admit, that stuff was dirty. I mean just soooo fuckin wrong, hahahaha. So I called my hottest sadistic friend over. Oh and I told her about your “castration cuckold” folder and she even agreed to bring her boyfriend over to Fuck me while she's destroying your nuts! I wanna see you hump the air desperately to try and get the “last orgasm of your life” out of your beta balls. I bet you've always wanted to be totally rejected like this huh??? With a couple of hot girls laughing at you… making you a eunuch slave. Should I put on a little show for ya while you still have your nuts? Maybe I should pose with the elastrator like this and blow some sarcastic kisses at you … muah… muah. Awe… did she band your nuts with this pink elastrator??? Did it hurt when she kicked your banded nuts??? Aiden Ashley

    Duration: 14 min | Price: $17.99

    You will be redirected to complete your purchase.

  • Maidization Full Season 1

    Maidization Full Season 1

    48 minutes. Includes 5 episodes. Episode 1:  Party Wimp Clean Up. Well, well well… you’ve certainly cleaned up well after the mess me and your friends made of you during the party. It’s a good thing I glued the wig to your head… Ya know, with all those kicks to the balls you took… geez, your head was bobbing up and down like crazy every time we ruthlessly kicked you in the nuts, hahaha. The house is in a real mess and my boyfriend made a mess of the bedroom so… that’s why I’ve dressed you up in a maid’s outfit. Episode 2: Cucked and Dolled Up. I'm back from shopping… I cuckolded you, making you buy me lingerie and stuff… Then making you help me get ready for my dates. I’ve realized how much I love fucking you over… Now I’m going all the way. I’m going to turn you into a permanent sex doll. We’re going to start off with hormones and corset training. Then we’re going to get your ears and nipples pierced and get you a tramp-stamp tattoo. Episode 3: Publicly Paraded. Awe, Did the pretty girls at the lingerie store giggle when they saw you walking around the store? Now go try on your new lingerie and put on a pair of high heels and a thick coat of lipstick. let’s practice walking in heels… seductively. Hahaha. Episode 4: Lingerie And Lipstick. Do ya think my lips will turn him on and get him super-excited? Do you think my date’s going to like the new lingerie you paid for? Get over here and help me put on my super-high heels. I want you to suffer and look at the feet that made you a sissy… a shaved and permanently pierced sissy girl, hahaha. Episode 5: Cleanup Cuck. You're totally cucked and totally fucked. I’ll even bring my lovers home and make you serve us drinks. Then I’ll make you my fluffer, helping get my lover rock hard and ready, and then, when you’re done, you can be the clean-up cuck. Don’t forget, 24/7 in lingerie for a week. In complete denial of course. Let’s see what that does to you, sissy. You're manhood is fuckin destroyed! Hahaha.

    Duration: 48 min | Price: $34.99

    You will be redirected to complete your purchase.

  • Dressed Up And Bullied

    Dressed Up And Bullied

    Get bombarded with mind melting visuals of pantyhose and silk and satin as you listen to her laugh and talk to you about the new job she set you up with. She saw your internet history and made sure you're now sissified and working for a big bully! The girls all want you to twirl and show them all the pretty clothes that you'll be wearing from now on. Oh and she might have set you up by slipping you penis shrinking supplements, oops! And now she expects you to jerk off and thank her. At the end you'll be humping her satin skirt with your ruined one inch nub. NOTE: This was created to work equally as well as a cuckolding clip where she is your wife… or a Taboo clip where she is your Step-Mom. AI Pixatrix

    Duration: 13 min | Price: $12.99

    You will be redirected to complete your purchase.

  • Cupcake Journey

    Cupcake Journey

    You started out confessing a fascination with her pink outfits. She offered put you in them PERMANENTLY. You refused at first but her step-Step-Sisters gave you a whole new wardrobe anyway! It escalated from miniskirts and fuzzy pink sweaters to nothing but ridiculous PINK POODLE outfits! After weeks of humiliation they decided to redo your bedroom and wardrobe to turn you into their full time sissy clown! You couldn't refuse because you secretly NEEDED this! Your journey of discovery meets the point of no return with a trip to the salon to become a permanent pink cupcake girl! You return home with tattooed makeup and piercings forever and the thrill of having to introduce yourself as a cupcake wherever you go from now on! AI Pixatrix NOTE: This was created to work equally as well as a cuckolding clip where she is your wife… or a Taboo clip where she is your Step-Mom.

    Duration: 8 min | Price: $16.99

    You will be redirected to complete your purchase.

  • Ai Salon Sucker

    Ai Salon Sucker

    Gee, we don't usually get requests for humiliating haircuts. I'm going to need you to basically sign your stupid life away. Can I do whatever I want to you? I mean, I'm pretty enough, right? So you'll let me really fuck you up, right? Pixie Cut, Lipstick Earrings, Nipple Piercings, Tramp Stamp and more! Ai Actress: Pixatrix Valentine

    Duration: 7 min | Price: $6.99

    You will be redirected to complete your purchase.

  • Cucked And Clowned

    Cucked And Clowned

    I know u don’t like me working here but it’s the best Cabaret in town. And my boss is really great. He put on a great **** stage show… don’t be jealous. … Huh??? You would? You’d make a bet like that? … What would happen if you lose to him? … … Oh, I see… so uh, if he wins, you’ll be his clown? … hehe… a fuckin clown? … … I’d love to see the that actually. Did it feel weird to see your own girlfriend trot up on stage with the silver platter of gorilla glue that he used to put that red nose on ya? … mmm, he wanted me to be the showgirl that kissed him and handed him the glue. Mmm, so sorry, babe. Oh, here’s last months clown now! … isn’t he just precious? … … not an ounce of resistance left in him, … haha. .. … … we call him Chuckles! He was a boyfriend of mine too! He thought he was man enough to march up on that stage and volunteer to be ****d… and he thought he’d be able to resist. … … but now he’s a gay little clown… a cucked clown! And I know it makes your little clown dick hard when you watch him cover me in his thick creamy loads, right Bozo? Ai Actress: Pixatrix Valentine

    Duration: 13 min | Price: $12.99

    You will be redirected to complete your purchase.

  • Sissy For Alphas

    Sissy For Alphas

    You're gonna need to be a sissy for an Alpha Couple after watching this mesmerizing video. You'll be the sissy that needs to come over and do chores for the pretty girl that you have a crush on even though her boyfriend insists you dress up as the most ridiculous sissy ever! LOL And best of all, you got mind fucked by a hot AI girl from Valentine Network! Hilarious! AI Pixatrix Valentine

    Duration: 5 min | Price: $14.99

    You will be redirected to complete your purchase.