Valentine Network

Category: Cross Dressing Encouragement

Million Or Makeover Episode 2

Bisexual Encouragement Bisexual Gay Humiliation Cross Dressing Cross Dressing Encouragement Crossdresser Crossdressing Crossdressing Made To Crossdress Cuckolding Encouraged Feminization Feminization Sissification Sissy Fetish Sissy Training Sock Fetish Socks

Zara gets praise and a warning from the Spacebabe Generals to be more hands on with her Sissy recruitment. Doja and Harley suggest the latest wanna-be influencer as the next contestant on Million or Makeover! Zara arranges a set-up with Ryder to see how weak he can be for a bit of humiliation and destruction. All goes well when Ryder gets a boner for the Sock and Cuck humiliation she shows him. Now Ryders putty in Zara's hands as she books him for total Sissification on her Galactic gameshow! Starring: AI Zara, AI Doja, AI Harley Categories: Sissy Training, Sissification, Feminization, Socks, Sock Fetish, Cuckolding, Latex, Cheerleaders, Bisexual Encouragement, Encouraged Bi, Make Me Bi, Shaving Fetish, Humiliation, Special Effects, Cosplay, AI

Duration: 10 min | Price: $9.99

Starring: Zara Valentine AI, Doja, Harley Tip Zara Valentine AI Directly

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October 6, 2026
Nailing The Role (Episode 2 of Season 1 of Producer of Pretty Lies)

Bisexual Encouragement Cross Dressing Cross Dressing Encouragement Crossdresser Crossdressing Crossdressing Made To Crossdress Sissy Training

Awe, you look so cute down there all smooth and hairless, hahahaha… now keep in mind that I can see through that sheer pink and chiffon robe, sweetie… If you get hard while looking at my perfect feet… I’m gonna have to give YOU pretty toes, hahahaha. Now let’s get your nails done so I can take more videos of you humiliating yourself… I mean, practicing for your role, hahahaha. And, don’t forget… you’ll get a kiss from your favorite celebrity crush! Well, you’ll have pink nails and look stupid and humiliated… but I’m sure you’ll still enjoy it a little, right??? Hahahaha. Starring: Stella Sol Categories: Humiliation, Foot Fetish, Sissy Training, Crossdresser, Feminization, Bi, Fem, Crossdressing, Make Me Bi, Sissification, Leg Fetish, Ass Fetish, Leotard Fetish, Bodysuit, Wimp, Bully, Nerd, Beta Male, Domestic Servitude, House Bitch, Milf, Shoe Fetish, Shoe and Boot Worship, Foot Fetish, Legs, Leg Fetish, Virgin Humiliation.

Starring: Stella Sol Tip Stella Sol Directly

September 16, 2026
Dressed Up And Bullied

Bisexual Encouragement Cross Dressing Encouragement Cuckolding Encouraged Bi Feminization Humiliation Jerk Off Instruction JOI Lingerie Make Me Bi Masturbation Humiliation Mind Fuck Music Video Office Domination Pantyhose Stockings Nylons Silk And Satin Sissy Training Small Penis Humiliation Special Effects SPH Taboo

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

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September 11, 2026
Cupcake Journey

Bisexual Encouragement Cross Dressing Encouragement Cuckolding Encouraged Bi Feminization Humiliation Jerk Off Instruction JOI Latex Lingerie Make Me Bi Masturbation Humiliation Mind Fuck Music Video Pantyhose Stockings Nylons PVC Silk And Satin Sissy Training Special Effects Taboo

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

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September 11, 2026