Get Fitted

Shopping takes forever. You thought it might be a quick outing, just going store-to-store crossing items off Megan's list, but you way underestimated how long buying girls' clothes takes.

You spend nearly half an hour in the first store alone and only end up buying one pair of bottoms.

But to your surprise, Jeff doesn't seem impatient at all. You find him waiting on a bench outside the store watching something on his phone. When you come over he hops up with a smile. "Where to next?"

You spend the day like that, going to one store after another, trying on clothes and buying them with Jeff's credit card.

After while, you get used to the process. When you find an outfit that actually looks cute, you feel really good and snap a few extra pics to send to Megan.

"omg, YES! That outfit is a MUST! Your body looks fire, slut!" She throws in a bunch of emojis and you smile reading her over-the-top encouragement. You know you should feel weird being told you look good cross-dressing, but you've never had that kind of validation from a popular girl before... or anyone, for that matter.

And since no one can see... You turn and pose in front of the mirrors in the changing room, pouting your lips, winking at yourself, arching your back a little to accentuate your butt, and take a few pics just for you. May as well have some fun while out, right?

The first weird part of the day was your first stop at a women's underwear store. Pink and black stripes and scantily-clad mannequins line the doorway.

You go inside, nervously glancing around to make sure no one is close enough to hear and approach the woman standing behind the checkout counter. She's a tall perky blonde, barely older than you, with her hair tied back in a ponytail. She smiles and says "Hi! Anything I can help you with today?"

You mumble, trying to put your hands in your pockets before you realize your skirt doesn't have any. "Um, I need help... finding a bra. Like one that fits..."

She nods, "Have you ever been fitted for one?"

When you shake your head, she smiles warmly, grabs some measuring tape and says, "Come with me, I'll get you fitted and find you some cute ones to try on." Then she takes you to a fitting room and closes the door.

"Okay, remove your top and anything under. I'll take your measurements and we can try some different styles on you."

You turn with a start, covering yourself defensively. "Remove my-!? C-can't I keep it on? Or at least my sports bra?" You hate the idea of being exposed while cross-dressing. Surely if you took your top off she would realize you were actually a boy.

But the woman shakes her head. "We need to get the most accurate measurements to find the best fit for you. If you're wearing something that already doesn't fit right over your body, we might get the wrong size. There's no need to be embarrassed."

You slowly peel your top off and look in the mirror. The pink sports bra you're left wearing is one Megan loaned to you. It's way too tight around your chest, but the cups look limp and baggy since you can't fill the space intended for Megan's breasts. A pang of self-consciousness wells up in you as the woman nods for you to continue.

You take a deep breath and take your sports bra off. Blushing, you subconsciously cover yourself with your hands and look up at the blonde, wondering what she must think of you.

But she just smiles and says, "There, see, that wasn't so hard, was it? Can you put your arms out for me now, sweetie? I need to take a couple of quick measurements and then we'll be all done!"

You put your arms out to the side and mumble, "Sorry..." as your flat chest is exposed.

The woman chuckles gently, pulling the measuring tape out and wrapping it around the lower part of your ribs and across your back.

"What for, honey? You're beautiful and you'll look so cute once we get you into something more flattering."

You gulp and tense as she moves the tape up, over your nipples, and writes something down in a pocket notebook. "You don't mind that I'm... you know... a guy?"

She smirks, meeting your eyes in the reflection of the mirror. "Honey, you'd be surprised how many boys shop here. Personally, I think its great that more and more of you are starting to wear panties and bras. You look adorable. And come on," she says, flicking your skirt up for a moment, "panties are way more comfortable for the erm, smaller variety, if you know what I mean."

You blush, knowing exactly what she meant, but you take the encouragement anyway. You were getting used to panties, after all. And you had to admit the snugness and softness they offered was kind of nice.

The woman finishes measuring and hands you a little piece of paper with all your numbers on it. You think you're done, and prepare to thank her, but of course it isn't over yet.

She tells you to wait in the changing room and comes back minutes later with armfuls of bras in every shape, style and color. Megan has a field day with the pictures you send her, loving the fact that the shop assistant had to help you through the whole process.

When you're finally truly done, you have a whole drawer's-worth of bras that actually fit you perfectly.

Before you leave, the clerk stops you and says, "Oh sweetie, one last thing. If you haven't already, you should stop by Divine on the second floor. Ask for Jenny. I think you'll like what she has to offer." She beams warmly at you and lets you thank her, then leaves to go back to her shop.

You find your way back to Jeff and hand him your bags, then start towards the second floor. On your way, you glance over at your stepdad and giggle. He looks silly carrying your purse and about a dozen hot pink and purple girly clothing brand bags. But its kind of flattering. He seems to really be enjoying just taking you shopping, and you like that.

You wonder if he'll notice that you're wearing a cute new bra under your top that actually fits right. Deep down, you kind of hope he does.