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Chapter 27 by PrincessAriana PrincessAriana

What's next?

Wear a Bra/ Change with the Girls

You're in your room with Megan, the next morning. She had agreed to help you with your life - or as she put it, 'Help you be more girly.' She was on her knees on your bed, putting the finishing touches on your makeup while you sat patiently. She had insisted on helping with your makeup every morning, you think mostly to get back at you for insulting hers. Even on school days, she'd said you had to at least wear 'nude' makeup. Occasionally she would scold you for bad posture and correct it with a push on your back.

"What are you planning to wear to school today?" she asked.

You shrug. "I don't know. I was just going to throw something on. Jeans and a T-shirt probably. I don't dress girly at school."

Megan roll her eyes. "It still matters what you wear. If you're really serious about, uh, how did you put it? 'Learning to not care what people think' or whatever, then you should give it your all, all the time, sissy boy."

You blush and wince a little, prompting a scolding and a posture correction from Megan. You weren't used to being called a sissy yet. Truth be told, you had only said you were one to prove a point and make Megan stop pitying you. You hadn't ever actually considered yourself a sissy, but it was too late now. There was no way you would backtrack without Megan seriously roasting you for it. And it was too good having someone to talk o about everything that was happening with your life. You kind of liked gossiping with the popular girl - even if the gossip was about yourself.

"How am I supposed to 'give it my all' at school? There's no way I'm wearing skirts and dresses and all the stuff I wear at home there. I told you about what happened in the locker room already when I accidentally wore my panties to school." You grimace, remembering how much Megan had laughed.

"Yeah, exactly!" the cheerleader replies, switching from touching-up your makeup to brushing your hair. "The cat's kinda already out of the bag, Aiken. The whole school knows you wear girls' underwear. Plus you'll be changing with the girls now, right? There's no way you can go back to wearing briefs, or Sports Pants or whatever you call them. Nuh-uh. I'm sorry but you have to wear panties full time now if you don't want the girls in there to eat you alive. You'll look like some pervert if you show up to the girls locker room and aren't even wearing girls underwear anymore. Now where do you keep your bras?"

You quickly turn and almost slap your face against the brush. "My b-bras? Why?" Jeff hadn't ever asked about your bras, even though he'd bought them for you. You assumed they were more for decoration, to make your dresser drawers feel more girly, but didn't think anyone expected you to actually wear them. "I don't have... you know... I can't fill them out or anything..." you mumble.

Megan rolls her eyes again, forcing your head back to forward. "Uh yeah, a lot of girls can't, Aiken. Doesn't mean they don't wear bras. You're just an AA cup - nothing to be ashamed of. Did your daddy seriously not know your cup size? You need to make him take you shopping again, and actually get clothes that flatter you this time. Until then, I'll loan you some of my old sports bras to wear. I have a few that should fit you."

"But-!"

"No buts, sissy! Now get changed! When you're done we'll swing by my house on the way to school for the bras. And I'll be checking every day from now on to make sure you're wearing everything you're supposed to be. Got it?"

You had **** but to agree.


You felt so weird walking through the halls wearing panties and a bra under your clothes. You had gotten somewhat used to panties by now, but with the addition of the bra, it was like being back at square one. The material squeezing your chest and the bands wrapped around your shoulders and back felt so cumbersome. You were sure it had to be visible through your clothes as well. Did the slight padding in the cups make it look like you had little boobs under your shirt? Would people sitting behind you in class see your bra straps? You could feel you self-consciousness creeping back up inside you.

You could barely think straight the whole day, and that was before gym.

You rush straight to the locker room before class, but your class the period before had been across the whole school, and there are already tons of girls inside when you slip in. You hold your breath and close your eyes, feeling your heart send powerful waves of nausea through you as you await your fate.

But no one says anything. You stand there shaking for several long seconds, but none of the girls even seem to notice you. You quietly make your way over to a free locker far away from the groups of giggling, chatting girls, and start to change.

You go as quickly as you can, fumbling your zipper down, and practically ripping your shirt off while desperately hoping no one sees. Your panties today - chosen by Megan when she insisted on looking through your panty drawer that morning - are soft pink bikini cut wit a glittery trim. Your bra is a white sports bra with a front zipper between the cups - the word PINK is written in all caps around the lower band, in rainbow letters.

You've just started pulling your gym shorts up when a girl opens a locker only a few down from yours and says, "Oh hey Aiken!"

Startled, you turn and find a girl from your gymnastics team smiling at you. Or is she smirking? Meeky, you stutter out, "O-oh, hi, Ashland..."

Ashland is a tall blonde girl with a ton of freckles. You don't know much about her beyond that - you keep to yourself at gymnastics practice. You're surprised she's even talking to you.

"Cute bra!" she says - and to your complete surprise, she strips right in front of you without blinking an eye. The girl's ample breasts bounce out as she shrugs out of her baby blue bra and reaches into her locker for her athletic wear.

You stare dumbly, watching her bare breasts sway as she bends over and tugs her pants down to her ankles, apparently totally okay with you seeing her white thong. Maybe changing with the girls wasn't the worst thing in the world after all!

But then you realize with horror that something is straining against your panties. Your small bulge has started to become an erect rod. If any of the girls see... If Ashland sees, you'd be ruined. They would kick you out of the locker room for being a pervert.

You turn away from the girl quickly, averting your eyes from her body, and desperately try to make your boner disappear. You clench your fists and think about baseball, nature, polynomial functions - anything to turn your stiffy into a softy.

"You're doin' really well at gym. I'm so bad at doin' all the stretches Coach assigns for us to do at home, but you've gotten like way more limber than when we started. I need like an app to remind me to just stop watching Tik-Toks and like actually stretch but like I'm too lazy to even set that up, so like-"

Ashland chats away, unaware of your battle to turn your hard-on into a hard-gone. You manage to pull your shorts up, but that does little to hide your embarrassing protrusion. All you can do is wait, nodding along with Ashland and pretending like you aren't pitching a pants tent.

"Uh, Aiken, are you even listening?"

You jolt upright, and stiffly turn towards the girl, ready to be chewed out. "S-sorry..." you mutter, humiliated.

But Ashland just shrugs. "Whatever. All I said was you're wearing the wrong gym shorts. Those are the guys' shorts. Here, just wear my spares and roll them up if they're too big." She shoves a pair of girls gym uniform shorts into your hand and adds, "Oh, and do this with your shirt. It's way cuter," and ties the bottom of your shirt into a knot on one side so that part of your midriff is exposed.

"Th-thanks..." is all you can say as Ashland walks out to gym class. You're way too embarrassed to react properly. You look down, and to your relief, discover that your erection has subsided. You let out a sigh and quickly switch into the new shorts - which are significantly shorter than the basketball-style uniform shorts you wore before. Much more of your thighs are exposed now, giving you a much leggier look.

When you walk out onto the gym floor for class, you think you catch Lucas staring and blushing, but he quickly turns his head when you look his way.

When you get home after school, you run upstairs like always and put your home clothes on. You decide a nice cute summer dress would be comfortable, slide into some heels, touch-up your makeup, and throw your hair into a ponytail to start cleaning and cooking.

You're vacuuming the living room when Jeff gets home. You stop the loud vacuum and smile when he comes inside. "Hey! Welcome home!"

"W-wow!" he says, looking you up and down. "Damn..." He drops his suitcase on the floor and stares.

You rub your face and look down at yourself. "What? Is there something on me?"

Your step-dad shakes his head. "No, it's just... look you really se- I mean, _pretty _right now. Are you trying to butter me up for something?" He grins playfully.

"Actually..." you say, remembering what Megan had said that morning, "I do need to go to the mall sometime for new clothes. Could you take me shopping this weekend?"

Jeff looks at you skeptically. "What kind of clothes? You aren't trying to buy yourself boxers again, are you?"

"No, no, nothing like that, I just need... um... you know..." you lower your voice, suddenly finding yourself a little self-conscious again. "I need some bras that fit me better... and some more flattering outfits..."

Jeff's eyes widen a little, looking over your body blankly as if lost in his thoughts. He nods and says, "O-oh... yeah. Definitely." His mouth grows into a big smile. "I will absolutely take you in that case!"

What's next?

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