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Only real men wear heels

Summary:

Marco didn't think it was wrong or bad to do what he loves doing, even if that meant crossdressing. It wasn't really hurting anyone, it was just what he did in his free time. But the last thing Marco needed was a demon blackmailing him into playing matchmaker.
Tom's only focus is getting back together with Star. Until it isn't.

Chapter 1: Expect the unexpected

Chapter Text

Marco usually always knew what to do, or at least had some kind of plan. It was his thing, he was the plan guy. He was usually prepared for any problem that came his way. But out of all the bad possible situations he had envisioned in his mind, this was not one of them.

It wasn't really a secret that Marco liked to dress up in pretty dresses and skirts, except that it was. The thought had always been there, like a gentle tug in his head whenever he would see a pretty dress worn by a girl, or a nice skirt with the right top. His head would always whisper how nice it would feel to have it. To feel the material against his thighs.

It didn't take long for Marco to come out and tell Star about these thoughts. And why wouldn’t he? Star is his best friend, his companion, his pal, his, well his everything; in the platonic sense anyway. But it still terrified him to admit it. It wasn't normal to tell a princess from a different dimension that you like their dresses and skirts; especially if you were a guy. When Star didn't say a word, Marco was sure that he had ruined their friendship forever. He was about to turn away and play the whole thing off as a joke, laugh it off like he usually did…

Only to have Star grab his arm and turn him around gently. She was surprisingly soft, telling him how she understood and it was okay. Marco couldn’t keep the grin off his face. Star then proceeded to drag him to her room and make him try on every single one of her outfits.

Since that day, no one other than Star and his parents knew about his hobby. Well… up until now.

"…What the hell?" Tom finally said after several moments of the demon staring wide eyed at Marco in awkward silence. He had just stepped from the dimensional portal he made in the floor, muttering something to himself before looking up to see Marco standing in front of the mirror. This wouldn’t have been so bad if Marco wasn’t in a black lace skirt and in a very feminine cream colored top.

But he was.

Marco himself was frozen on the spot; too scared to even breathe. He was in the process of trying on an outfit that Star had bought him during her recent shopping trip. When Star mentioned she got him something, he worried it would be something extravagant. Instead he was pleasantly surprised when it was actually something normal looking.

Star bought him a cream colored off the shoulder knit top with a strap to keep it from completely slipping off the shoulder, a black pleated skirt with lace trimming that stopped around mid-thigh, and finally thigh high socks that were the same cream color as the knitted top.

For a split second after the initial confusion, Marco could have sworn he saw something in the demon’s glowing red eyes; something hungry, greedy, and carnivorous . But it was gone as soon as it appeared. The hungry look replaced with something more calculating, cocky, and just so Tom that Marco chalked the previous look up to be just his imagination.

"Well well," Tom continued walking until he was in Marco’s room, the portal disappearing as soon as he was fully out. "Isn't this a surprise? If I understand this correctly, male humans don't normally wear female clothes, isn't that right?" The demon’s lips had twisted into a self-satisfied smirk with all the confidence of a cat playing with a caught mouse.

"Go away Tom." Marco growled defensively. He was slowly being backed up against his mirror, the cool, smooth surface chilling his heated skin. Of all the rotten luck why did Tom have to show up now?

"Does Starship know?" Tom asked with a tilt of his head, his eyes seeming to drink in Marco's appearance. Marco rolled his eyes.

"Of course she does, she knows everything about me." He looked Tom square in the eyes and jutted out his chin with sudden defiance as he said, "Just like I know everything about her."

The demon actually growled at Marco, and lunged forward. That’s when Marco remembered, ‘oh yeah anger demon, probably shouldn’t have made him mad.’ He stood stiffly and squeezed his eyes shut as he felt his room temperature warm up drastically; like opening a heated oven door. Marco was prepared for the fireball that would most likely burn him to a crisp…

but it didn't come, or perhaps it did he was actually dead. But he could still feel the smooth material of the skirt on his legs so...? Marco slowly opened his eyes to look at the demon.

Tom had moved in closer, a little bit too close for Marco’s comfort. His room having cooled down some and the fireball that erupted in the demon’s hand was extinguished with a flick of his wrist. Now he was just staring frowning at Marco’s clothes in distaste.

Marco tried to pull back as Tom reached forward, bunching Marco’s top in his fist, and pulling the material closer to him. He stared at it having an internal conflict on whether to burn the material or not.

"Hey! Let go, you're going to stretch it!" Marco complained, not actually daring to grab the demon's wrist. He was considering yelling for Star when Tom finally spoke.

"Take it off."

What?

"What?"

Tom glared at Marco as if he had said something too stupid to comprehend."Take it off, the clothes, I can't see you as the human male you are when you are dressed like a girl.” He sneered tugging the material again, “I have sworn never to harm a female of any species. Now take them off." He yanked the bottom of the top up.

Marco, however was having none of that, "Hey! Knock it off!" He shoved the demon away from him; not enough to actually make him fall over, but enough to put some space between them. Sniffing indignantly, he smoothed out the wrinkles from his shirt. "Star isn't here right now alright?! So go back to the underworld or something, just go away!"

Tom however was staring at Marco, "I don't remember you having this much hair?" He said more to himself, as he reached forward patting Marco's head. Marco had grown taller, but Tom was still a good head taller than him.

Tom pushed the brown locks back until he reached the pontytail holding the rest of his hair. His hand traced the tied back hair, before brushing it over Marco’s shoulder and pulled. Hard.

Marco winced as his head was suddenly jerked to the side, "Hey!" Marco swatted Tom's hand and tossed his hair back over his shoulder. "That hurt! Geez, yes it's real, I asked Star to use her shadow transform spell." He didn't know why he was explaining it to Tom. He shook his head, feeling a headache grow in the back of his skull.

Tom took a step back, "Well whatever, I don't care." He intertwined his hands together and placed them behind his neck, tilting his head back in annoyance. "Is Star really not here?"

"She's not. Now get lost, please ." Marco said. He moved over to sit on his desk chair, glaring up at Tom. Tom didn't need to know that she was taking her usual catnap. And when Star naps, she naps .

Marco chewed on his bottom lip, the gravity of the situation dawning on him. He enjoys dressing as a girl, but as much as he loves dressing up, he doesn't actually want to be a girl. He feels ashamed at that, knowing how wrong it was but loving it anyway. He closed his eyes, feeling conflicted.

He doesn't feel ashamed.

Well, he shouldn't...

but...

Snap!

Marco snapped his eyes open when he heard the snap of a camera. Tom was holding a phone in front of him, his lips curled into a smirk. It wasn't until after the forth or fifth snap that Marco reacted.

"Hey!" Marco jumped up, rushing to the demon, trying to snatch the phone out of his hands, "Stop! Give me that phone! What the heck!" He grew desperate, jumping up when Tom held the phone over his head.

When the phone suddenly burst into flames Marco took a step back, staring at the area in which the phone used to be, "Is it...?" he heard himself say.

"Safe in a place in which only I know? Yes." Tom sat down on Marco's bed, smiling sweetly up at the shocked brunette, "Why don't we make a deal?"