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Operation Simp Moms

Summary:

When Henry was ten years old, Operation Cobra was designed to bring back the happy endings; now he’s fourteen, Operation Simp Moms’ objective is a little more…devious?

(Sequel to 'Your Mom's Hot').

Notes:

I wasn't meant to upload this today but I'm feeling a lil reckless. Please enjoy what could be the start of a very fun series for me!

Chapter 1: Blueprint

Chapter Text

Henry Swan-Mills is well used to his Ma gazing at his Mom like she has every answer to every question, like, ever. The fact that his Mom - a woman with ‘Evil Queen’ on her CV - has also taken residence in simp city central is….weird. Definitely weird. 

 

“I’m calling it Operation Simp Moms,” Henry tells Isaac, as they walk along Main Street after school. 

“That’s a dumb name,” Isaac replies, mouth full of Snickers. 

“You’re only saying that because my Mom doesn’t pay attention to you anymore,” Henry quips, which shuts his friend up. “Okay soooo you know that we’ve been trying to convince our parents to take us to Forest Fun for forever?”

“The adventure park three hours away from town?” Isaac supplies (providing exposition as if he were still a book character). 

“Why yes, Isaac, that it is indeed the place.” 

Isaac eyes the mischievous grin on Henry’s face with trepidation. “You’re telling me Operation…Simp Moms is gonna get us there?”

“I literally broke a curse as a ten year old. You just have to believe.”

Isaac takes another bite of his Snickers bar.

 

Robin Hood is lingering on the steps of the Town Hall: no fruit basket this time, just flowers. 

“Hullo, Henry,” he says, with a weary smile. They’ve had many a run-in here. It would be kinda stalkery if Robin wasn’t such a “pathetic pinecone” (Emma’s words). 

Henry gestures at the wildflowers bunched in Robin’s hairy hands. “Are those for Mom?” 

“Yes, I picked them myself today. I thought they could brighten up her working space.”

Henry suppresses a sigh. “Sure.”

“It is really quite lovely to see Regina and Emma getting along so well. I saw them holding hands the other day.”

Henry raises an eyebrow. 

“Your mother deserves a good friend like that.”

Henry reckons that his mother could stick a 10ft rainbow flag in the front lawn and Robin still wouldn’t get it, so he just pats the guy on the shoulder and enters the building.

 

His Mom looks up from doodling in a notebook. Doodling. Love has changed Regina Mills more than any curse or realm or villainous personality trait. (Okay, maybe not the latter. The evil thing was intense).

“Hi Mom, how was your day?”

“Wonderful, thank you darling. Emma brought me lunch.” She beams as though Emma hasn’t brought her lunch every day since they started dating (and…before).

Good, Henry thinks, flopping onto the couch, The atmosphere is heavy with simp already. Time to go in. 

Speaking of Ma,” Henry begins, playing with the tassels of a throw pillow, “we were talking the other day about fun things we could do as a whole family…”

Regina puts down her pen. “Go on, I’m listening.”

“And Ma suggested Forest Fun,” he glances up at his Mom,    who is frowning, “because she’s always wanted to go on a zip line and stuff but I said that there was noooo way you would agree to….”

The rest of his sentence proves redundant. Regina has already snapped open her laptop and is typing, presumably ‘Forest Fun tickets’, with a determined ferocity. 

 

Henry should have seen this coming. He remembers the day Hook and Emma became a thing - how his Mom had slammed every kitchen cupboard making dinner and sat at the head of the table with only a scowl for company (he had escaped at the first cupboard slam).

When he asked her, hesitant, what was wrong she had said, “Nothing,” then, “Since when did Emma like men?”

Which made Henry stare at her, understandably confused because he was 90% certain his dad was a man (you could never be too sure in this magical age). 

“Who wears eyeliner,” Regina cleared her throat, “Since when did Emma like men who wear eyeliner.”

 

Now, Henry watches his Mom’s satisfied smile as she retrieves her credit card from her purse, motivated by the single goal of making Emma happy, more fairy godmother than scary sorceress. 

All this to say, the signs were there.

 

[Text Message: Henry]

OSM is a-go.

 

[Isaac]

wut

 

[Henry]

omg u suck at this 


Their dinnertime seating arrangement is this: Regina at the head of the table, Henry to her left, Emma to her right. Emma pulls the chair out for Regina; Regina kisses her cheek in thanks. Henry marvels at the domestic bliss they’ve all stumbled into. 

“I have tickets for us to somewhere special this weekend,” his Mom announces. 

“And Isaac,” Henry reminds her. 

“Yes, and Isaac.” She looks at Emma with tentative, hopeful eyes. “And…your parents.”

Emma misses her mouth, lasagne smashing into the side of her cheek. Regina reacts in an instant, and leans over to swipe at the sauce on the other woman’s face. “Emma,” she says softly, much like she would to a baby Henry. 

“You…you invited my parents?”

Regina sits back against the chair, wiping her finger on a napkin. “I did. I know I haven’t seen them since we…well, became we, but you told Henry that you wanted to do something as a whole family.”

“I did!?” Beneath the table, Henry kicks his Ma’s foot. “I mean, that would be…nice… but…I didn’t want to rush you.”

“Snow and David are important to you. And you’re,” Regina takes Emma’s hands in hers, “Important to me.”


“Henry,” his Ma says, speaking quietly now that Regina is cleaning up the kitchen, “What have you been up to?”

Henry takes a sip of juice. “Nothing.”

Emma folds her arms, studying him. “Superpower, kid, remember? Puberty doesn't protect you.”

“I haven’t done anything that isn’t for the good of our family.”

She wrinkles her nose. “Was it your idea to have Snow and David come too?”

“Er, no. I think Mom just misinterpreted what I meant.”

Great,” she slumps forward onto the table, “Can you at least tell me where we’re going?”

“Nope. Only that Mom thinks you’ve been really wanting to go, so act happy when we arrive.”

Beneath the table, Emma kicks Henry’s foot.

 

[Henry]

told u!!

this weekend!!

mom got us tickets!!

 

[Isaac]

my sugar mommy <333

 

[Henry]

I will take Luca. I mean it.  

 

[Isaac]

sry

[…]

is the mission over then

 

[Henry]

*operation 

 

[Isaac]

is it 

over

 

[Henry]

stick with me young jedi

u shall learn the ways of the universe

 

[Isaac]

k

henry?

 

[Henry]

yh 

 

[Isaac]

can u get ur mom to take a selfie w me at the wknd

for the gram ;)

[…]

for operation simp thing 

[…]

regina i mean

in case u needed clarification 

 

[Henry]

I didn’t 

and no