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Chapter 23
by
PrincessAriana
What's next?
Have Dinner Part 2
The first thing Megan says is, "Why am I here?"
The two of you are in your room together, alone. You're both still wearing your party dresses and heels. Jeff and Billy are downstairs, drunk.
"I... just wanted to--"
"To what? Get me alone in your room? You little creep." She sighs heavily and sits in a bean-bag chair on your floor, kicking her heels off and pulling her phone out of her pocketbook. "Whatever."
"I'm not a creep!" Your face is flush and hot. You've never had a conversation with a popular girl before. To be called a creep right away kind of hurt.
She looks you up and down. "Oh, really? Could have fooled me. I guess you just cross-dress for fun, is that it?"
You blush and look down at your heeled feet. "I... well... yeah, I guess. I mean... I enjoy it... some. I feel--" What was the word Mr. Brandt had used earlier? "--pretty..."
Megan tilts her head back and laughs, practically snorting with derision. "Seriously? Oh god, that's hilarious! You seriously want to look pretty? That's adorable. Should I braid your hair for you? We could paint each others nails, maybe. Wanna borrow some of my clothes?"
You keep staring down at your feet, silent. You know she's making fun of you, but you don't know how to respond. It's all new to you, and you're no good at talking to strangers. Especially hot, popular strangers that go to your school.
"Hmm, nothing to say to that, pretty-boy?" she continues. "Look, whatever you do in your own home is your business. But don't bring me into, okay? I don't want anything to do with a sissy boy."
"I-I'm not a sissy!" you blurt out.
"No? Do you shave your legs? Are you wearing a dress?" she gets up and moves closer to you, aggressively putting her hand on your thigh and sliding your dress skirt up. "What do you have on under here, hm?"
You quickly squeak and back up, pushing her hand away.
"Men don't wear panties. Sissies do," she says firmly, smirking down at you.
You look away. "Whatever. I don't care what other people think..." Your feelings don't really match your words.
Megan grins and pulls her phone up, pointing it at you. "Really? Then you wouldn't mind if I took a few pics, right? I would love to show all my friends how cute you are in your little dress!"
You grimace as you hear the shutter sound several times, but do nothing to stop her.
"Hmm, something's missing..." she looks around the room and finds a box of makeup Jeff bought you along with your clothes. "Ah!"
She pulls the box onto the bed with her, and gets close to you, forcing you back until you're literally up against a wall, and she's straddling your legs on her knees, a powder brush in one hand, a mascara wand in the other.
"Y-you're going to put makeup on me?" you ask, heart sinking. Makeup is something you haven't tried yet. Jeff hasn't asked about it yet, so you've been content with getting by without it.
Megan nods. "Mhm. I may as well have some fun tonight. I had to cancel on my friends to come to this lame thing with you." She sneers the last word like its distasteful in her mouth. "Now hold still."
You close your eyes and let Megan put makeup on you. The brushes and powders tickle and feel heavy on your skin. You've never worn makeup before, and had no idea how meticulous it was to put on. Megan goes quiet for a long time brushing even strokes across your cheeks, or drawing pencil thin lines around your eyes. It's way more of a process than you'd imagined, and from your perspective, Megan seems more like an artist than high-school cheerleader.
After a while, Megan starts speaking again. Her fire has died down some, and she suddenly seems a lot more somber.
"Why do you, cross-dress anyway. Is it really a fetish? It has to be more trouble than it's worth." You try shaking your head but she grabs your chin. "Hold still!"
You say, "No, it's not like that... I mean, I just started so I still don't know yet either... It's not like I hate it, just--"
"Wait, what do you mean you 'just started'? Like you just woke up and were like, 'I'm going to wear panties and a dress today, that will be fun'?"
"No, no, Dadd- I mean, Jeff made- I mean, asked me to. I've only been doing it a couple weeks now."
Megan's brush stops for a moment. "Your stepdad... made you?"
"It's just to get me ready for the real world, you know? Like learning to not care what people think of me and doing stuff around the house and stuff. So I'm wearing girly clothes and doing all the cooking and cleaning until mom gets back from her work trip."
"Oh..." Megan's voice softens. "Don't you feel weird doing it, though?"
"Sure," you shrug. "That's sort of the point, though. And it's not really that bad. I mean, I don't have to dress up at school yet or anything like that. Just in private, for Jeff."
"I see..." Megan puts her brushes away and snaps the makeup box closed. "All done..." she hands you a compact mirror. "Um, hey, Aiken..."
You look at yourself in the mirror. You're completely unrecognizable. All your features are softened and your blue eyes pop. Your skin looks perfectly smooth with just a hint of blush. Your lips are cherry red and look somehow more full. Even your eyebrows have been smoothed somehow. You're almost attracted to the girl in your own reflection. "Hmm? Yeah?" you answer, still staring at yourself in disbelief.
"I, um... I'm sorry for being rude earlier. I mean, saying all that stuff about you being a sissy or whatever. I didn't mean it. Let's just... be friends, okay?" she smiles at you, but something about it is hollow, and it makes you uncomfortable. Still, it was better than being called a creep.
"Oh... sure," you say, forcing a smile too. "Thanks."
Mr. Brandt collects Megan a while later, so late at night it's almost morning. They leave and drive home, leaving you to clean up alone since Jeff is passed out on the couch.
You leave your makeup on until you go to bed.
What's next?
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Stepdad Wanted a Girl
So he made you one
Aiken, a young boy in high school, gets feminized by his step dad while his mom is on a business trip.
Updated on Jul 19, 2025
by PrincessAriana
Created on Jul 12, 2025
by PrincessAriana
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