Studio Freaky presents a hot sissy roleplay full of feminization, humiliation, strap-on dildos, stripper heals, deep pegging, and anal fisting! Stellina Obscura has recently moved in with her boyfriend, Sean Saber. While he spends his weekend gaming with his bros, Stellina is busy making room for her things in his closet. She finds a mysterious box labeled, “Kendra the Slut.” In a jealous rage, she demands to know who this slut is and why all of her skanky clothes and sex toys are in HIS closet. Who is this bitch?! When confronted, Sean embarrassingly admits that the stuff belongs to him. Stellina is taken aback and realizes what he means. Her boyfriend is actually a sissy who loves to dress up and fuck his boi pussy with big dildos. Stellina is not phased by this discovery and tells him that she understands, “Everyone has their secrets.” She disappears into the bedroom while Sean continues to play video games. When she reappears, Sean is in shock at her transformation. She is in full domme attire and strapped with a 13-inch realistic dildo. Now, it’s time for Sean to make his transformation into a sissy slut who is ready for sucking and fucking. Sean strips down and is put into sexy knee-high socks and a garter belt, then slapped with a crop on his nice round ass. Stellina is going to fuck his tight, pink hole and warms up his boi pussy with her fingers. He is made to put on crotchless panties, fake tits, and a lacy bra. She objectifies him by manhandling his tits and grabbing his ass. The final touches to his adorable sissy outfit are a pair of 4-inch pink heels and cotton candy hair. For the last part of his transformation, Stellina finds his makeup collection in Kendra the Slut’s box. She puts makeup on his face, reminding him that he needs to be pretty if he’s going to suck her perfect cock. Sean is now Kendra, and Kendra must suck the little cock she keeps in her secret box. It warms up her throat for Stellina’s huge 13-inch cock. She jams her huge dick down Kendra’s throat. Kendra’s tight boi pussy begins to leak with excitement. Stellina demeans and degrades Kendra’s tiny cock. It might as well be a clit, it's so small. Kendra spreads her legs on the couch and gets her boi pussy fingered and fucked with her secret dildo. Stellina feeds the dirty dildo to Kendra’s cock hungry mouth. Her throat is deep and ready for ass-to-mouth. She is made to clean off all the anal juices off the dildo. When her hole is warmed up, Stellina takes her gigantic 13-inch cock and penetrates Kendra’s hole. She fucks her sissy long and hard while also stuffing her sissy’s mouth so she can be airtight. Kendra is realizing her dream of being a used anal whore, but she still needs to work harder to get the privilege of taking a cum load. So, she gets on her knees to take it doggie-style, taking cock so deep she moans and screams. Her tits are bouncing and her hair is a mess, but she continues to take Mistress Stellina’s cock and push her tight hole to its limit. Mistress sits on the couch and demands that Kendra ride her dick, lowering her hole onto her monstrous cock as deep as possible. Kendra is always ready to obediently suck the huge cock clean with her hungry mouth. In the final segment of deep fucking, Stellina completely dominates her sissy’s hole with her entire fist and forearm. Kendra strokes her tiny dick, which might as well be a clit, until it is milking into her own mouth. After intense, deep fisting, Kendra is finally brought to orgasm. As Mistress Stellina promises, Kendra must eat every drop of cum. Her sissy blows her load into her own mouth and swallows at all. Mistress Stellina catches the stray beads and pushes it all into Kendra’s mouth. No cum is wasted! This cum-dumpster sissy is left happy and satisfied on the floor, sticky with ass juice, lube, and her own cum. We had a great time making this video for you. Thanks for supporting Studio Freaky and make sure to check out our clip store for more amazing videos full of fisting, pegging, Femdom, sissification, feminization, humiliation, CBT, CEI, and more!