1080 HD Raven never wanted Marcello. She always wanted to have two daughters. Instead of a second Step-Daughter, Marcello came into her life. That’s ok. Raven will turn Marcello into the girl she’s always wanted. Thankfully, Raven has the help of her Step-Daughter, Kimber. Kimber has always wanted a step-sister. She’s happy to help her Step-Mom make Marcello into the step-sister she never had. Marcello’s gender re-training will start now. Kimber and Raven have already locked Marcello into a pink chastity.

The step-mother and Step-Daughter are ready to help prepare Marcello for his new life as a girl. To continue his training, he will be shipped away to Raven’s step-sister’s house. Raven’s step-sister runs a home for sissies, where to earn their keep they are whored out on dates. In preparation, generously, Kimber and Raven are going to help Marcello learn how to take very big cocks. Because Marcello does not have the proper number of fuck holes for a girl, they will have to train her ass to function for men like a cunt.

First, the step-mother and Step-Daughter play dress up with Marcello, who will now be referred to as “Marcy.” Kimber is very excited to share her clothes with her new step-sister, Marcy. Kimber’s clothes are very provocative, but Kimber tells Marcy that men like provocative clothing on girls. In his new role as a sissy slut, his function will be to please men and do things that they like. Learning to wear revealing clothing for men is just a start.

Kimber and Raven are really pleased with Marcy’s transformation. They’ve spent enough time on Marcy’s new look, now, it’s time to train her to get fucked like a girl. Kimber and Raven spit-roast Marcy. She must learn how to suck cock while getting fucked from behind. This kind of sexual multitasking is foundational for a slut’s training. Raven begins the ass fucking with a large dildo.

Marcy’s new step-sister has an extra-large sized dildo, even bigger than her Step-Mom’s! Kimber thrusts the enormous dildo deep into her step-sister’s “pussy.” Marcy cries out. It’s too big! But Kimber and Raven insist that Marcy must learn to take it. She will thank them for the good solid training once she is earning her keep as a whore. Good whores do as they’re told. Marcy must learn to be a good whore. With Marcy flat on her back, Kimber fucks her ass while Raven fucks her throat. Her pink chastity is in full view. Marcy is well on her way to becoming an excellent sissy slut. (17:34 long)

Jane is back from the Sissy contest with bad news.   The judges said her chastity tube was too big.  They thought that her butt plug was too small.  Jane is humiliated as the girls inspect her chastity tube and butt plug.  They start her cock sucking training with a small gherkin.  Astro shoves the gherkin down Jane's throat.  They need to get rid of her gag reflex.  Next they move to working out and stretching her ass.  The girls start off first with a small gherkin up her asshole.  Jane is humiliated.  Jane has this distressed look on her face as she is breached with the gherkin.  They move on to the much larger cucumber.  Jane bucks against her ties.  Jane is upset her ass hole is being stretched out with a cucumber.  Pretty soon the girls are reaming Jane's ass hole out.  Her hole is getting so big!  Astro then takes the cucumber and start thrusting it harder and deeper into her.  Lola feeds Jane a gherkin while Astro fucks her hole with a cucumber.  Jane bites into the gherkin while she watches her hole being stretched out from Astro’s thrusting.  Jane is being stretched!  Jane is given snack while Astro fucks her ass.  Eat your cucumber Jane!  Jane is completely humiliated.  Astro bangs Jane’s ass from behind in a deep grudge fuck.   This clip also has highlight video at the end as well. (19:34 long)

1080 HD Brianna has been training her step-son, Danielle, to become a sissy. She has selected romantic fiction for Danielle’s reading material. Appropriate literature is part of Danielle’s mental development, as he grows into an ideal sissy for his step-mother. Brianna calls Danielle into the room. Danielle has been dressed, head to toe in complete sissy garb. She wears a pink satin corset and pink garters to hold up her stockings. And of course, Brianna’s step-son has a pretty chastity to match the outfit. Brianna observes her step-son’s stride in high heels as she approaches. Danielle kneels beside Step-Mommy, and Step-Mommy pulls back her step-son’s wig to inspect the makeup application. Danielle has neglected to apply lipstick. Step-Mommy corrects Danielle and reminds her that lipstick is very important for a good girl to wear. Brianna moves on to inspecting her step-son’s chastity. Danielle complains to her step-mother that she has been in chastity for a very long time. Brianna makes her step-son thank her for keeping her in the device. It’s for her own good. Danielle understands that Step-Mommy knows best, but doesn’t like that she must wear head to toe pink. She is especially frustrated with the pink stockings, which are sometimes itchy.  Brianna is disappointed that her step-son has not yet learned to appreciate stockings. Brianna encourages her step-son to appreciate the softness of Step-Mommy’s stockings by massaging her feet. Danielle massages her step-mother’s feet. Brianna encourages her step-son to inhale the smell of her feet and kiss them. She reminds her step-son that training is necessary, because Danielle will be sent to her aunt, Alexandra for the summer. She wants Danielle to perform well at her aunt’s parties. Danielle complains. She hates spending summer with Aunt Alexandra. Alexandra spanks her, and it hurts. Brianna brushes aside Danielle’s complaints and starts to read to her from the romance novel. The novel helps mentally groom Danielle to be attracted to men. Danielle will appreciate the preparation once his step-mother and aunt start sending her out on dates. Danielle brings up the spanking again and complains to her step-mother that one-time Aunty Alexandra bent her over her knee and spanked her very hard. Danielle was upset and couldn’t sit for days. Brianna tells Danielle that she just needs to get used to receiving a hard spanking. Brianna pulls her step-son over her knee. She begins to strike her sissified step-son’s bottom one hundred times, compassionately, to prepare her for more extreme punishments from her aunt. (8:08 long)

Kenzie flips through a publication while her sissy is fucked by machine. The sissy has been strapped into a stockade and is completely helpless as its ass is pounded by the motorized dildo. Kenzie ignores the sissy’s whimpers as she reclines on a pink chaise. Cali drops by to visit. She’s equally interested in the magazine Kenzie’s been leafing through and joins her friend on the chaise for a cuddle. The friends chat about the publication and talk about nail salons, completely ignoring the sissy in training. Kenzie shows Cali how she’s been wearing the sissy’s chastity key for two months as part of its training as well. Cali thinks it’s great! To impress her friend and show off what a slut her locked up sissy has become, Kenzie turns up the sd on the fucking machine. The sissy complains that the adjustment hurts, but the Princesses just laugh. It’s chastity rocks and bobs between its legs as it gets pounded by the machine. Cali shows it some training material from the magazine while it gets fucked. The Princesses gang up and taunt the helpless sissy. They play with and vary the sd of the huge cock breaching its tight asshole. Kenzie shoves her fist into the sissy’s mouth and makes it gag on its own taste. Cali takes the controller and cranks the machine up to maximum sd. She finds a blonde wig and puts it on the sissy’s head. Cali makes the sissy kiss her shoes while wearing the blonde wig and getting fucked. Kenzie leaves to get ready for her nail appointment and asks Cali to supervise the sissy for her. Once Kenzie leaves the room Cali cranks the machine way up. The sissy starts to cry out and make a fuss, but Cali tells it very firmly to shut the fuck up. (14:13 long)