Jesse has gotten into trouble at school for playing with matches, and Sasha has picked him up from school and driven him home. When he whines about getting in trouble (even though he's thickly diapered and strapped into a car seat), Sasha decides that he needs a more severe punishment than usual. And when Jesse thinks it's a good idea to cuss in front of little Christopher, Sasha pulls out the soap.
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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.
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.
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.
Loni's been chatting with a girl online, and he thinks he's about to score. But when he shows up to meet this internet chat room girl things don't go quite as planned. Kat and William have been plotting to get themselves another adult baby sissy, and Loni has fallen into the trap. Loni downs a special drink when he arrives at the couple's home, and is soon feeling small and compliant.
Little Jeffrey is woken up from his nap by Miss Kat and gets a nice surprise - Kat is feeling a little horny and wants her adult baby boy to nurse on her breasts while she masturbates. While Jeffrey sucks hungrily on Kat's nipples and breasts, she rubs the front of his diaper and teases him about the bulge in his thick disposable diaper. When Jeffrey asks Miss Kat for permission to cum, Kat stops playing with him and denies him an orgasm.
Little Christopher is strapped into bondage mittens and let back into the corner to stand in his punishment shoes but soon agrees to submit to an anal punishment in exchange for being released from the painful punishment shoes. Christopher is stripped down to diapers, then put on hands and knees with diaper pulled down and cute little bottom exposed to Miss Kat. Miss Kat starts off invading Christopher's bottom with her gloved finger but soon moved on to larger intruders!
Christopher has been a naughty little monkey. Instead of doing the homework Miss Kat had assigned to him, he blew it off and played instead! As a punishment Miss Kat decides that Christopher needs to be kept in diapers for the day. But when little Christopher starts to untape his diaper Miss Kat has to escalate his punishment. Instead of being a diaper boy Miss Kat decides that Christopher might start behaving a little better if he's kept as a diapered girl for the day!
Diapered sissy Loni is doing her best to do a good job sucking Will's strap on, and Miss Kat decides that Loni's dress should be taken off so everyone can see her thick disposable diapers. When Loni has proven she can do a good job sucking on the strap on, she's finally allowed to suck on Will's real cock! On all fours with a stiff cock in her mouth, Loni is spanked and fondled through her diaper (but not allowed to cum).
Logan is thrilled to finally have some private time to be a diapered sissy baby with his wife out to a movie with Kat. But when the two women unexpectedly come home early from their day out, Logan gets caught playing in a thick, pink, fluffy cloth diaper in the nursery! After Kat and Lily have a good laugh at Logan's expense, the two women decide to play with this new little baby girl and finish dressing her in pink plastic pants, and a ruffled, pink, little girl dress. Next it's time to feed the baby!
Miss Kat has a big surprise for her diapered sissy baby Loni today. If Loni is a very good girl, she's going to get to get all dressed up for Will and suck his cock! First Miss Kat gets Loni dressed in a thick Abena disposable, puts a cute little girl hair clip on him, dresses Loni in an adorable skirted onesie, then makes her look all grown up with some pretty makeup!
William let Tommy tie him down so that they could have some kinky fun, but he didn't expect to be put into diapers! He complains to Tommy about being his "little diaper bitch," but Tommy convinces William to play along after a few rough slaps. When Tommy rubs the vibrator on William's diapered crotch though, he starts to discover that maybe diapers can be fun after all. Still recalcitrant though, William has to be paddled and punished by Tommy until he'll admit out loud that he's Tommy's "good little diaper bitch."
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.
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.
Therapist Katherine explains to Jeffrey while slipping a pair of pink nursery print plastic panties over his cloth diaper that she thinks it would be more appropriate for his therapy to involve regressing as a little girl rather than a little boy. They decide to start off by dressing little Jeffrey in an adorable pink and white baby dress complete with lots of ruffles and a pinafore. Jeffrey starts to feel more at ease as Katherine buttons up the back of the dress and ties a big bow to hold Jeffrey's pinafore in place.
William has dressed his diapered sissy Rebecca in an adorable pink satin dress with a matching ruffled diaper cover. He can't help but get aroused with his sissy all wrapped up and dressed so cute, so he decides it's time for Rebecca to practice cock sucking. Soon Rebecca is kneeling in front of William's stiff cock and getting a lesson in proper sissy cock sucking. Rebecca isn't as enthusiastic as William would like, however, and it's soon decided that Rebecca needs some extra encouragement.
It's Kitty's birthday, and Miss Karen has a big surprise for adult baby girl Kitty, a new (live) baby doll to play with! Kitty gets to have lots of fun with her new doll, and decides right away that he should be in diapers just like her. Next, Kitty decides that she wants a diapered baby girl doll, but her new doll starts to protest. Lucky for Kitty, Miss Karen gives her a ball gag to use to keep her naughty baby doll from talking back. With her doll properly silenced, Kitty proceeds to dress the doll up in a cute pink baby girl playsuit.
Jeffrey has been more stressed than usual at work lately, and it's starting to affect him in strange ways. For example, he's started grinding his teeth at night and sucking his thumb unconsciously! Fortunately for Jeffrey, his therapist Katherine wants to share with him a controversial therapy technique: regressive therapy. After introducing the idea to Jeffrey, Katherine persuades him to come take a look at her special "exam room" dedicated to regressive therapy.
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.