SissyEmily65

“Look, baby, if you have an issue with this you really need to take it up with Daddy! He asked me very clearly how many diapers we’d brought and he did his math and said it wasn’t nearly enough! I guess I didn’t realize it was only equivalent to 2 a day, and he’s right, with the beach and the pool and your usual messes, that isn’t enough! Sooooo, you can hate this shopping trip all you want, but it’s necessary for your comfort, baby!”

A backseat, six and a half hour road trip while his wife Jenny drove their SUV, loaded with bags, on the phone with her girlfriends while Henry struggled to occupy himself by reading his rules, playing with a few barbie dolls, and staring out the window.

A two bedroom condo right on the beach rented by Daddy, specifically because the second bedroom was tiny and decorated for two girls, with a twin bunk bed and Disney princesses everywhere.

A list of rules sent the day before the drive with instructions for Henry to write them down, in pink crayon, so he could study and review them throughout the trip. Rules as simple as #2: Sissy Holly must sunscreen heavily on the beach to protect her pale and delicate skin, #5: Sissy Holly must knock and politely ask permission to enter Mommy and Daddy’s room, or #8: Sissy Holly may not order for herself while out to eat... but also as devious as #13: Sissy Holly must loudly announce needs while in public, including diaper changes, ba-ba refills, or anything else with “Mommy / Daddy, may I?” at full volume. Henry’s least favorite, without question, was #1.

#1: Sissy Holly will not reference “Henry” in any way or behave as if he exists through the entirety of the vacation. Failure to obey this rule will result in extreme punishment.

Having spent most of the car ride memorizing these, he hadn’t stopped thinking about what “extreme punishment” could mean. Over-the-knee spankings were standard. Chastity was constant. Daddy treating his wife like his slutty girlfriend was a given. What else could he do? How much further could Daddy take this whole insane fantasy?

Henry’s mind raced as the older redneck woman behind the counter stared slack-jawed at the beautiful brunette buying a summer’s supply of diapers for the ridiculous, demure sissy standing behind her.

“Mommy?” Henry’s voice betrayed a hint of his repressed male self, causing Jenny to raise an eyebrow and dramatically open her mouth with shock, only to soften slightly as she saw the look of sincere worry in her sissy husband’s eyes.

“Is everything okay, darling?” She’d known some version of this was coming. This was lot, even for a sissy as pathetic as her Henry. It was also a summer she’d been looking forward to since the moment her boyfriend suggested it, and the idea that a sissy’s objections would ruin that was ridiculous. Still... “Tell Mommy, baby.”

“W-What does Daddy mean by ‘extreme punishment,’ Mommy?” Poor Henry’s trembling lips betrayed incoming sobs. “It’s... I’m worried, Mommy! This is all going to be so... so hawwwd to do all summer!”

Jenny cooed as she strapped her husband into the backseat of their SUV.

“Oh honey, we know it will be. That’s why the punishment exists, silly! We wouldn’t punish you so harshly for failing something easy, we’re doing it because we want you, we need you, to be a good girl this summer so we can trust you!” Her eyes sparkled. “Do you really want to know?” Henry nodded feebly.

“If you misbehave this summer, your extreme punishment... will be your return to life as a “man,” not that you’ll ever be one again. But Daddy and I have discussed it, and... this dynamic is all either of us want. And we need you to prove that you can obey, forever. That’s the punishment. If you aren’t a perfect sissy for us... and I know you will be... then Daddy and I will stay together, and you won’t.”