Diapered Schoolgirl Penny is stuck in detention writing standards on the board, but the thought of being punished while dressed in diapers and her school uniform is just too much for the naughty little girl to resist! Soon she's got her hands off the chalk and down into her diaper. The thick, crinkly, padding around her crotch makes her so horny, and she just loves the feeling of the diaper squeezed between her legs.
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Diapered schoolgirl Gabriella has gotten herself in trouble for not doing her homework, so she's been grounded to her room for the afternoon. Gabby has no intention of staying inside though, so she sneaks out to the balcony to see if she can climb over the rail (all the while giving us a lovely view of her thick Cushie underneath her school uniform skirt).
Penny has decided, without permission, to cut and dye her hair in protest of being put into Miss Kat's care. Miss Kat bends Penny over a school desk, pulls down her humiliatingly thick cloth diapers and plastic pants, and proceeds to give Penny a lengthy hand spanking. Penny continues to be a bratty little schoolgirl, which only extends her punishment, until her cute little bottom turns a vivid shade of red.
Even though it's against the rules, diapered schoolgirls Kitty and Bailey just can't keep their hands off each other. But when tattle tale Lily tells on them, the two girls find themselves on the receiving end of a spanking from Sasha. So naturally, at the first opportunity, they try to take their revenge on Lily by pinning her down and spanking her diapered butt!
Schoolgirl Kitty finds herself in a strange adult-sized nursery with another young lady. Stephie has been in the nursery for a while now, and she's been kept in diapers and strange, kinky outfits for quite some time. Since Stephie's learned to be compliant for the nursery's owners, Will and Gabe think she'll be a good role model for Kitty now that Kitty's going to be trained to be a good little diaper slave.
Bad schoolgirl Kitty is constantly getting into trouble, and Hunter doesn't know what to do with her. At his wit's end, Hunter calls Gabriella for advice on what to do with the unruly brat. Kitty's attitude changes very quickly when she finds out that she's earned herself a punishment. Hunter takes measures to make sure Kitty uses her cloth diaper and ties her to the changing table so that she doesn't run off.
Kitty stops Christopher and Jesse on their way home from school and convinces them to come "study" with her while Sasha isn't home. They start fooling around, and the boys find out that Kitty is dressed in a diaper. Kitty's strong advances (and willingness to take off her clothes) convince the boys to make out with her.
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.
Diapered, dressed as a schoolgirl, and on his hands and knees, Logan waits obediently for Miss Kat to peg him with her strap on. Kat takes her time with Logan, teasing, spanking, pounding, and playing with him. But when Logan starts to think that he should be allowed to fuck Miss Kat, she decides to put him in his place. Miss Kat tapes Logan back into his diaper and gets out her paddle for the day's lesson.
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.
Bailey can't seem to help getting into trouble at school, and William has decided to enroll her in a new school where Miss Kat is the headmistress! Bailey isn't too sure about this arrangement but reluctantly agrees. Miss Kat sits Bailey down to explain the rules at the new school, and (noticing Bailey's wet training panties) she explains to Bailey that she's going to be put into diapers.
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.
Diapered schoolgirls Bailey, Chrissy, and Penny are tired of little Kitty being teacher's pet, so they've decided it's time to bring her down a notch. The three naughty schoolgirls concoct a plan to gang up on her when the teachers aren't around. While Chrissy keeps watch, Bailey and Penny pin Kitty down, spank her, and tie her hands together with the ribbon from Kitty's hair.
Schoolgirl Bailey has gotten herself into quite a predicament, and she finds herself tied up, taped into a thick disposable diaper, and locked into a playpen. Things are about to get even more complicated when William finds Bailey's phone in her purse and texts a couple of her friends invite them over as well. When William checks Bailey's diaper, he finds that it is soaked and proceeds to change her into a super-thick cloth diaper and humiliating ruffled plastic pants.
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.
Always the instigator, diapered schoolgirl Kitty does her best to tempt her classmates Jesse and Christopher away from their studies. While the teacher is away Kitty convinces the boys to take off their shirts, and then their pants, and soon the three of them have their hands in their diapers and their lips on each other. Naturally Sasha catches them in the act and puts Kitty into the playpen to take a nap. Kitty isn't happy with the situation and throws a tantrum before finally quieting down.
Diapered schoolgirl Kitty doesn't want to pick up her toys, and she's mad at Miss Sasha for keeping her in from recess. When Kitty refuses to pick up after herself she finds herself on her hands and knees (diapered bottom on display) in time out. Even when given another chance, Kitty still doesn't cooperate and finds herself on the receiving end of a spanking! Kitty reluctantly puts her toys away, but then the diapered girl is gets even more tired and cranky.
Diapered schoolgirl Penny is being taught to be a good little girl in Miss Kat's class, but she refuses to behave. When she confesses to being late to class because she was kissing other little girls, Kat decides that maybe writing some standards will help to improve Penny's behavior. Penny starts out writing her standards (thick cloth diapers bulging out from under her school jumper) but soon the temptation to play with the schoolroom toys is too much for her.
Schoolgirl Bailey has been having accidents at school, and Kat has been called to come pick her up more times than is acceptable. Kat brings Bailey home in her car seat (still wearing her wet training panties) and explains that Bailey is going to be kept in diapers until she can prove that she can stay dry. Miss Kat changes Bailey out of her school uniform and into an adorable purple baby dress and thick Molecare disposable diapers.
Bailey is so cute sitting there on the rocking horse. When Kat gets on behind her they start touching each others thick Cushie diapers. Once they begin getting very horny (by discovering each others diapers) they get off Horatio and head to the crib. Where they discover they are both wearing matching diapers. Before long, naughty fingers are exploring naughty places, and the two horny diapered schoolgirls can't keep their hands off each other. School uniform jumpers come off and bottoms get playfully spanked.
Little Kitty is being a good girl for Miss Sasha. Kitty's been put into very thick cloth diapers and a pair of heavy, locking plastic pants. A pair of leather mitts over her hands make sure that Kitty has no chance of pleasuring herself at all. After Kitty licks Miss Sasha's pussy to two lovely orgasms, Sasha decides Kitty still doesn't get to cum. When Kitty sees the vibrator plugged into the wall nearby, she decides to clumsily turn it on and try to rub herself to a diapered orgasm.
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.
Miss Kat's nursery school is full of well-behaved little sissies for a reason, she deals with misbehavior swiftly and effectively! Sissy Rebecca's mistress has sent her to Miss Kat's nursery school to learn how to be a good little girl, but Rebecca can't seem to keep from wetting the thick, humiliating Classy Comfort disposable diapers she's been sent to school in. Kat sends Rebecca to time out for some time to think about why she can't seem to remember to use the potty like a big girl.
Kitty's was sent her to school with a thick Bambino diaper on under her plaid school uniform jumper. She had several accidents during the school day and feels like a very naughty girl for wetting herself with all her classmates around her. When she gets home from school she takes the opportunity to examine her soaked diaper more closely. She knows that she's not allowed to take off her diaper without permission, but that doesn't mean she can't still have a little fun with her vibrator.
Diapered schoolgirls Bailey, Chrissy, and Kitty are playing in the nursery, and Chrissy decides to draw a picture... of her and Bailey teasing baby girl Kitty! Bailey and Chrissy decide to make art into reality, and they pounce on poor little Kitty! Despite the fact that all three schoolgirls are taped into super-thick Bambino disposables (that are constantly peeking out from under their school uniform skirts), the two older girls hold Kitty down, give her a spanking, and tell her to suck her thumb.
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.
Adult schoolgirls Bailey and Kitty look absolutely adorable in their authentic blue plaid schoolgirl uniforms, white knee high socks, black Mary Janes, and thick ABU Cushies peeking out from behind their plaid skirts! But while they're playing, Bailey suddenly becomes very quiet. Kitty wants to know what's wrong and figures it out right away. Bailey has wet her diaper! Kitty tells Bailey not to be embarrassed and that seeing Bailey in wet diapers is actually making her very horny!
Bailey is supposed to be taking a nap in the crib at adult baby nursery school, but she decides to be naughty and play with the vibrator she's hidden in the crib. While she's got one hand in her diaper and has her eyes closed in concentration, Kitty comes into the nursery to wake Bailey up from her nap. Caught in the act, Bailey is furious with Kitty for walking in on her and decides to punish the diapered schoolgirl herself. First she drags poor little Kitty to bend over a school desk and starts with a stinging spanking on her diapered bottom.
Katherine is having a wonderful time playing in the secret nursery she found in the house of her client, Mr. Watkins. Having already dressed up like a little schoolgirl in training panties, she's starting to feel more adventurous and decides to try on some of the diapers she found earlier. She climbs up onto the adult sized changing table and tapes herself into a Molecare disposable diaper with a liner tucked into the middle to make it extra thick. With the diaper taped up between her legs, forcing them apart a little, she feels very little and adorable.
It's another school day for sissy schoolgirl Loni, and William is getting her ready for nursery school with Miss Kat. It's a very special nursery school just for sissies, and Miss Kat is very strict with her little sissy girls. Loni wants to wear her big girl panties to school, but Daddy puts her in thick disposable diapers for nursery school because she's been having accidents. While little Loni is on her way to school though, she has an accident and knows that she'll be in trouble with Miss Kat when she gets to school.
Katherine is a business-like real estate broker who is helping Mr. Watkins to sell his home. When she forgets her cell phone one evening (and misses Mr. Watkins' message that he will be delayed), Katherine lets herself in the home and begins to take a look around. She is shocked to discover a room in the home decorated just like a little girl's room but proportioned for an adult. Katherine is intrigued by the assortment of toys and clothes in the room and decides that it wouldn't hurt anything to try just a few things.
Schoolgirl Kitty concentrates intently on her math tables until ... uh oh ... she has a big accident in her training panties. She tries to hide it, but it's gotten her legs, socks, and the seat of her desk all wet. Inevitably her teacher, Mr. Tommy, finds out about her wetting and puts the protesting schoolgirl back into humiliating baby diapers for the rest of the school day. To "encourage" Kitty from having accidents in the future, he also gives her a firm paddle spanking over his knee and stands her in the corner, school jumper tucked into her exposed diapers.