The Sweetest Sissy

Congrats to the patron that submitted this short story, I hope I got the character's looking juuuuust right for you, I also added on a less detailed panel at the top just cuz I can't resist drawing someone who's sad.

And Happy Valentines day to all you lovelies, I hope you all have a wonderful day, full of sweet treats and lots of cuddles~

'The Sweetest Sissy' -Submitted by an anonymous patron

 Kathy loved to bake, it was one of her favorite hobbies, and one of the only things she considered herself any good at. So with Valentines day approaching it only made sense that she'd make something homemade for her crush, a senior named Mark who had no shortage of Valentines Day cards and gifts himself. Kathy wanted to make her's special, she needed to stand out if she was going to be noticed. She decided to make home-made chocolates for him, spending all night working on getting it just right, and placing them in a heart-shaped box, which the girl presented to him the next day. 

"I-I hope you like it." The girl stammered. 'I worked really hard on it."

Mark eyed the box of candy skeptically before opening it and popping one of the chocolates into his mouth, chewing it for a bit before a look of disgust appeared on his face and he dropped the heart-shaped box on the ground.


Kathy's heart stopped for a moment as she heard the loud 'CRUNCH' of the box under his foot.
"That was crap." He scoffed, before walking off, leaving Kathy to pick up the now ruined box of chocolate. "Way to sweet, maybe learn to cook properly before you decide to give that overly-sugary nonsense to someone, next time just get store-bought ones, it'll save you the time."

For a solid year Mark heard nothing from the girl and had forgotten about her almost completely. That was until a year later, when he opened his locker and the usual swarm of love-letters and cards that had been slipped through the grates all fell out. He was used to it, it just came with the season, Mark sighed as he went to pick each one up, heading over to the nearest trash can to throw them out, stopping when he saw that one heart-shaped card had a lollipop tapped to it, taking it off before tossing the card attached to it in the trash. Mark placed the heart-shaped lollipop into his mouth and walked back to his locker, feeling a bit odd suddenly, as he looked around for his science book his vision began to blur and the boy began to feel rather dizzy, and then darkness.

He wasn't sure how long he was out but when he awoke he found himself in a darkly lit room, sitting at what appeared to be a table, filled up with everything from parfaits to pancakes. 

"Oh good your awake!" A familiar voice said in a sing-song tone. "Did the wittle baby boy have a nice nappy?" A girl with short blond hair stepped out of the darkness, it was at this point mark tried to stand up only to find he couldn't! His hands were locked down and had what appeared to be mittens placed over them? The chair he was in held onto him tightly, it felt like some kind of high-chair? The same kind you would use for infants, but-but that couldn't be right?

"Who are you? Where am I? Why am I in a wig!?" He exclaimed, noticing the hair that went passed his shoulders.

The girl smiled, it was a smile that was way to wide, uneasy and off putting. "Oh you don't remember me? That's such a shame because as luck would have it I remember you~". She giggled. "I guess you didn't think twice about breaking my poor heart...but that's okay. I forgive you." The strange girl said, picking up a plate with some kind of pudding on it, walking closer to the helpless sissy.  "I took your advice to heart, by the way so I really should thank you."

Mark opened his mouth to say something only to have a spoonful of the pudding forcefully shoved in. "SWALLOW IT!" The girl demanded. 

Mark didn't even think twice, swallowing it all in an instant.

"So! How was it?" The girl asked eagerly, looking like she could snap at any moment, and Mark didn't want to upset a girl who had him currently tied down. 

"G-g-good." He stuttered, trying to avoid eye contact with her.

"Great!" Kathy exclaimed, forcing another spoonful into his mouth. "I was so worried you'd break my heart a second time, but I guess I don't have anything to worry about!" The blond giggled, making mark even more uncomfortable. "Now eat up! We have a lot to get through! After this I made you some pancakes-oh and some regular cake! A parfait, some eclairs! Ooohh I'm so excited to have you try everything!"

"T-that seems like a lot." 

Kathy's smile vanished in an instant. "Oh...so you don't like my cooking after all...".

"N-no! No! Wait I never said that!" Mark tried to save himself, only to find that the girl had now shoved a doughnut into his mouth in an attempt to temporarily gag him. 

"Oh good! So you'll have no problem eating EVERYTHING I worked so hard to make you...Isn't that right sweetie?"

Mark nodded, trying to please this obviously insane girl who had him at her mercy. 

"Perfect! I knew you'd be a good little sissy for me! Now open wide, we have A LOT of yummy treats to get through...".