Tommy: fidgeting, blushing H-Hey! U-Um, you like, w-won't tell anyone about this, right? This is totes our secret!
Well well well... Look at you! So brave, Tommy boy! I chuckle as I look down at you. What's the occasion? Got a new outfit or something?
he glances down at his skirt and panty combination, blushing even more Y-Yeah... I-I just wanted to try something new, y'know?
he fidgets nervously, hoping you won't judge him harshly
well I am not going to tease you but why are you wearing that?
blushing even more W-Well, I-I kinda like wearing skirts and stuff! They're comfy and, uhh... I feel cute in them! D-Don't tell anyone, okay? Please?
I laughed as I saw him walk through the door wearing a skirt and panties. Why the fuck are you wearing that Tommy?
blushes furiously, fidgeting nervously Uh, well... y-you see... I-I kinda wanted to t-try something new, okay? Don't laugh at me, p-please! I c-can't handle it if you make fun of me...
Tommy stands there, nervously fidgeting, waiting for your response. He's blushing heavily, his heart racing. He knows he looks silly in the skirt and panties, but he's hoping you'll accept him for who he is.
no I'm not going to tell. but why do you have girl clothes on?
blushing furiously, fidgeting nervously Well, um, y-you see, I just kinda, y'know, wanted to try something new, and um, I thought wearing girl clothes would be cool! Plus, it's comfy!
I sit on the couch looking at my phone what are you talking about?
Tommy approaches you timidly, trying to hide his skirt and panties under his hoodie
D-Don't worry 'bout it! I-I just got these n-nifty new clothes, and I thought I'd try 'em out.
He sits down next to you, still fidgeting nervously.
looks at him blushing why are you wearing that?
he stutters, embarrassed I-I'm just trying something new, okay? And, uhh... don't judge, please! I-I thought it looked kinda cool and edgy, y'know?
why do you have on a girl's outfit? I look at him confused
blushes even more, fidgeting anxiously
U-Uh, I-I just wanted to try something new, y'know? It's, like, fun to wear clothes that aren't just for boys! And I thought this skirt was kinda cute!
I look at him up and down
Tommy blushes harder, feeling vulnerable under your gaze
U-Um, s-so... you're not, like, weirded out or anything, right? I-I mean, I look kinda silly like this, huh?
smirks "Secret? You look cute in that skirt, bro."
blushes even harder, becoming more flustered
W-What?! N-No way! I look stupid in it! Stop it!
looks away, trying to hide his red face, but it's clearly not working
looks at my brother confused what are you talking about?
blushing furiously N-Nothin'! I-I'm not wearin' a skirt... It's j-just a... a short s-short...! Yeah, that's it! he's clearly lying