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Christopher and Gabriella are fooling around while William is a work, but William comes home early and catches the two in the act. Upset that Christopher is making a move on his wife, William decides to put Christopher in his place. He diapers Christopher and dresses him in a pink sissy dress.
Having hidden the hated diaper taped onto her by Miss Kat, Bailey tries hiding in the classroom to avoid her new teacher. When Bailey complains that it isn't fair for her to not be allowed to take off her diaper by herself, Miss Kat decides that maybe Bailey shouldn't be allowed to be a big girl any longer. Miss Kat starts stripping Bailey out of her school uniform, then bends her over a school desk for a sound hand spanking.
Penny strips out of her leotard and William dresses her in a cute pink schoolgirl blouse with a Peter Pan collar. Penny adjusts her white tights while William buttons up her blouse, and then Penny is locked into a pair of heavy plastic pants. Even though she does her best to keep from getting put into the hated plastic pants Penny eventually finds herself dressed in a short, pink, plaid skirt with her thick diapered bottom peeking out for anyone who cares to see.
Having gotten themselves into trouble for picking on little Kitty, Penny, Bailey, and Chrissy are getting changed into baby clothes for a nap. Despite their protests and attempts to distract William from their punishment, the three naughty girls are stripped out of their school uniforms (down to their diapers) and dressed in embarrassing baby clothes. Once all the girls are changed William locks them in the playpen together for a nap.
In this sequel to "Reluctant Roleplay," Logan has returned to Miss Kat and wants to play with her again. He admits that he enjoyed himself before, and Miss Kat makes him promise to be a good little diapered sissy for her. Miss Kat watches, amused, while Logan strips out of his clothes and starts dressing in his cute little schoolgirl uniform. Miss Kat spreads a diaper out on the floor for him and thoroughly rubs powder all over his crotch.
Naughty little Penny just can't seem to keep her fingers out of her diaper, so William has dressed her in tights and a leotard in an effort to help Penny resist temptation. Penny's too horny to resist though, and she eventually finds a way to get her fingers into her diaper and get herself off. Her treat isn't without consequences however, and William discovers her at the height of her climax.
Adult baby girls Bailey and Penny are good girls at heart, but they think William's been way too mean lately. To make things right, Kat suggests that maybe the girls should put William in diapers and chastity. So when William gets home the girls pounce on him and unleash their diabolical plan for revenge! William goes along with the girls' plan for a while, expecting the girls to have their fun without things getting out of hand.
Christopher thinks he's in for some hot group sex, but things turn out a little differently than he planned. He doesn't know his new flings too well, but his hormones get the best of him when he agrees to be stripped and tied up. Soon things turn a little weird though, as the ladies powder Christopher's crotch and tape him into a thick, embarrassing diaper.
Schoolgirl Bailey has been nothing but trouble for her sexy teacher Miss Kat. When she refuses to do her standards one too many times, Miss Kat has no choice but to call her Daddy to pick her up from school early. While waiting for Daddy to arrive, Bailey is bent over the school desk for a spanking with her teacher's yard stick followed by a hand spanking.
Being put into thick cloth diapers, locking plastic pants, and confined in the playpen has made Bailey one very horny adult baby girl. She knows that Miss Kat does not allow her to touch herself without permission though, so Bailey asks Miss Kat to spank her and play with her so she can relieve the sexual itch that she just can't scratch. Miss Kat takes her down into the dungeon and puts Bailey on all fours on the bondage table for a spanking over her moistened diapers.
William is in the business of training good little boys and girls to be diapered slaves for his clients, and Miss Kat is one of his best clients. When Kat arrives to take a look at her potential new slave, Jesse, she immediately gets to work testing him out, seeing how well he responds to commands, and how quickly re responds to pain. After much poking, prodding, spanking, and groping, Miss Kat decides that she'll take home a new slave today after all.
Little diapered ballerina Kitty is in trouble, and she's been put into the corner wearing her "punishment shoes," 8 inch ballet heels! She's not happy about it, but she grudgingly tries to stand in the corner until William isn't watching. When the coast is clear, she immediately plops down on the floor and takes off the hated shoes. But when Bailey finds Kitty out of the corner and confronts her the two girls start fighting.
Miss Michele wakes up her adult baby girls Bailey and Kitty with a surprise... breast milk! The two girls nurse on Michele's breasts until they get very horny and decide to break out the vibrators. Naughty little Bailey gets a little too into her vibrator and cums without permission from her mommy. Her bliss doesn't last long, however, as she quickly realizes that she's going to be in big trouble for breaking the rules. As punishment, Bailey will have to put on a humiliating school uniform and clean her room.
After a couple of dates, Kat has invited Logan back to her house to play around. Logan is intrigued by Kat's stern, seductive outfit, but he's a little confused by Kat's choice of venue. Kat tells Logan that it might be fun to do a little teacher/student roleplaying. He's a little hesitant at first, but Logan's lust gets the better of him and he agrees to wear a plaid school uniform for Kat. He's shocked and reluctant when Kat gets a diaper out for him to wear, but agrees to wear it when Kat tells him how horny it makes her.
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