physically cannot talk about trans girl miles without having trans girl gwen 😔 because it's really about meeting That One Person who opens the door to everything else. gwen and miles start dating and miles realise that gwen is...super unconventional. he expected it and doesn't hold her to traditional relationship dynamics but she's been begging him to try on some of her clothes. it's not like he's against it--he's got healthy respect for different lifestyles and he's plenty curious--but he's been performing for his masculinity for so long he's apprehensive about doing anything to defy it

gwen gets her way in the end, and miles finds that dressing up in her clothes doesn't feel bad. in fact, he feels rather cute! it helps that gwen's clothes aren't super feminine, and she has an alt style that he loves. seeing that miles enjoys it, gwen begins suggesting more...feminine clothing. and a little make up to help him look cuter. it all escalates from here because, as it turns out, gwen loves fucking miles when he's all dolled up for her. gwen calling him a good girl as she nails his skirt-cladded ass has him weak in the knees, heart fluttering with something unknown

the bedroom isn't enough any more so they've decided to go on a little date while miles's dressed up. he's not at all confident so he puts hours in front of the mirror, applying, wiping, and reapplying make up and agonising over outfits until gwen has had enough and drags him out the door. he's got an oversized hoodie over his fit, much to gwen's exasperation, but they have a good time walking around. miles's taken aback when he's addressed as "miss" "girl" and "lady". miles has worried about looking unflattering but not much for passing (or did he?) so he thinks they're just being polite, but the comments boosts his confidence so he sheds his hoodie midday. he's convinced of that line of thinking until a small group of guys begin catcalling them. miles's immediate response is to be protective of gwen but when she lashes out first, telling them to back off from her girlfriend that he finally catches on. they make a few more lewd comments and miles has to drag gwen away before the situation turns nasty. after the incident, miles becomes a lot more aware of how strangers treat him as they walk around the city, buying treats and shopping around. it's nice to be perceived as a girl. it makes miles feel warm inside, like he's somehow satisfied, and that some part of him is fulfilled, but...

he mulls on it after the date. there's really only two people he could talk about it to. gwen and hobie. he calls them over, asks them questions that they readily answer. it's a murky topic, and while gwen does have some dysphoria and received her revelation earlier than miles, she's no authority on it. she convinces him it won't change their relationship if he wants to try it out. hobie is all in for it, and encourages miles to explore her gender. just between them for now. why not?

it's really nice, miles decides. they use her preferred pronouns in private but pav and margo catch on and start using it too even when she's not trying to pass. soon her little social circle are in the know and...she thinks she really really really like being a girl.

• miles ends up being even fussier than gwen and margo, because her fashion sensibility hasn't changed. her enjoyment of conventional looks mean that there's a lot of personal upkeep.
• her parents support her wholeheartedly but fear her socially transitioning while still in vision because of possible bullying...
• and just because i love migmi, miguel is a weirdo who accidentally refers to miles with her preferred pronouns before she's even out publicly because he spies on her so much 😔💔 miguel blamed it on beter and the guy gets chewed out by gwen for accidentally outting miles to spider society's number one asshat. thankfully he's normal about it! even if he does tries to offer to a private one on one session to design miles a more feminine suit...