24 Floors.

Maybe I had hoped my new found femininity would cure my hatred for shopping. If anything, it only made it worse. I didn't know how you could make so many clothes with so many different fabrics. When I bought clothes, it was simple. Medium t-shirts, size 30 jeans, and I was good to go until the next season. For some reason I had assumed it would be just as simple with the female section, and I was met with a shocking surprise.
"You would think the clothes would at least be cheaper than guys, considering how much less durable they are." I grumbled, sheepishly handing him the thin cotton blouse I'd accidentally ripped while trying on. We'd only been to the first shop so far, and I'd already learned how different the women's clothing section was compared to the men's.
1. Every employee came to ask you for help. This may have been for 1 of 2 reasons:
A. Maybe this one was more because Jack and I looked more lost in here than we would have in a house of mirrors, or
B. It was so much easier for a guy to shop. I didn't have to find my size in every brand and I could tell what fit me from the rack. Here, I had to choose multiple sizes of everything and trying them on in a fitting room, which took significantly longer. It was nearing lunch time and we hadn't even been through half of the store - however, we'd be much further behind if not for the help of a few dedicated store employees and even another customer.
2. I couldn't buy everything in the same place. This store was only to buy casual clothes. Jack insisted we had to buy nicer things somewhere different and undergarments at yet another store.
3. Nothing fit me correctly. If it was pants, they were too tight. If it was shirts, I didn't have the cleavage necessary for it.
Jack started to catch on to #3 on our third trip to the dressing room. Each time, I had gone in with the maximum amount allowed (10 items, at this particular store) and overall I had only been satisfied with two shirts that easily could have belonged in the guys' section. "You know, tugging on it like that isn't going to change the way it fits." Jack called from his seat as he watched me trying and fix the shirt I tried on. I really liked it; the only problem was I was flat-chested and had no curves.
By this point, I was close to tears and I really didn't want to deal with Jack stating the obvious. "Fuck off." I stomped back to the changing room.
"No good?" A muffled voice asked, disappointed. The people here were totally amazing. They were willing to help as soon as we explained the situation, which Jack and I hadn't expected. Just the opposite: we thought we would be spending the day with no help, wandering around stores and hoping we got lucky.
"She's still getting used to it, I think. Clothes work differently here, and it’s all happening a bit fast." Jack sighed. "We'll take these two shirts though and try our luck somewhere else after lunch. Thank you so much for all of your help. I don't know what we would have done without you!"
I avoided looking in the mirror until I was fully dressed in my own clothes. I'd seen girls wear similar jeans and my shirt was a unisex school tee, but I couldn't help but think I looked too male. I wanted something different. I wanted to be pretty in that conventional way popular girls were.
I would never look like them.
A knock on my door shocked me out of the incoming panic attack. "Jay? You almost done in there? I've paid for the stuff you wanted and we can go wherever you want for lunch when you're done."
"C-Coming." My breath hitched in my throat.
I could feel Jack pause outside. "Can I come in?" He asked after a moment.
I unlocked the door and he let himself in. He sat on the small chair in the closet-sized area and looked me over. "Have you tried tucking?"
My face went warm, teary eyes replaced by embarrassed cheeks. Truth be told, I had considered it, but in all honesty I had no idea how to do it correctly and I was a bit scared to try. "No..."
"You don't know how to, do you?" My lack of response was answer enough for him. "I can teach you!"
I gawked at him. I probably would have been less surprised if he’d told me he had a third nipple. "Dare I ask why you know how to tuck?"
He waved a hand dismissively. "Foreplay, role play, you know. Also, I have this really nice pair of jeans that only fit right when I tuck. I think some of these jeans will fit a lot better if you do it. As for the tit problem? We'll solve it after lunch and then maybe we can come back here if you liked the clothes here. What do you think?" Now, I actually started crying. "Shit, oh my god what did I do? Tell me what you want Jay."
I shook my head. No, no. That's not why I'm crying. "Thank you, Jack."
His grin made me feel even better. "Let's get some food, kid."
We ended up at Jack's favorite restaurant, Taco Bell, simply because there was nowhere better to go. I wasn't objected to some nachos, anyways. We ate almost silently, both too hungry to focus on anything but our food. "Oh!" Jack exclaimed through his last mouthful of taco. "By the way, I talked to Rian. We were talking about all of the hate you've been getting and we thought, if you're up for it, you could come record a Full Frontal episode with us. Maybe they'll get to know you better and won't be so harsh."
I had taken to listening to Jack and Alex's radio show during the day when there was nothing else to do. It was inappropriate and funny and everything I'd expect from a show hosted by those two. It had a decent following and personally, it would have been a great idea, if not for one problem. "What does Alex think?"
"Alex can suck a dick, honestly. He needs whatever stick's up his ass out and get over himself or he's gonna be down a boyfriend quite soon."
Biting my lip, I stared at my empty bowl. "I feel like I'm fucking everything up for you. Your fans, your boyfriend...they hate me."
I looked up just to see him roll his eyes. "The fans are just jealous, I promise. My exes got the same kind of thing when they were with me. And Alex? I don't know what's going on with him, honestly. He's never acted like this before. I've tried talking with him about it but he won't open up, either. It's his problem, whatever it is, and it probably would have come out sooner or later even if you weren't here." He didn't let me counter him before clapping his hands and jumping up. "Now, how about we take care of this boob situation?"
I doubled over in a fit of laughter when half of the restaurant stared at us, trying to figure out what "boob situation" was code for.
***
Victoria's Secret was possibly the last place I wanted to go, but Jack insisted. This place, he knew he could navigate without the help of shop employees. "Is this another role play thing?" I asked when he told me we didn't need assistance. The look on his face was more than enough of an answer for me.
"So, you'll probably want some of those boy panty things, at least until you get more comfortable. They're the easiest to tuck with. Go for the more spandex-type material, too. Once you figure things out, you can experiment more, but we'll just stick with basics right now. Pick out a few pairs in different sizes and styles and meet me at the fitting rooms in ten minutes. I'll look for bras." I waited for Jack to disappear inside the expanse of bras before even looking in the direction of the underwear tables. This was becoming too surreal for me. Deep down, this was exactly what I wanted. I could feel it. However, maybe Jack was right when he said it was all happening so fast.
I went for simple black to start with, finding a bunch of pairs that fit Jack's criteria and I would also like.
I met Jack with about ten pairs of underwear, mostly because I had no idea how girls' sizing worked so about 6 of them were in different sizes. Jack, on the other hand, had about twenty different bras in various bright colors held in a basket. I was beginning to see where our styles differed. "So, most of these are B cups. They aren't too big but they'll give you enough to work with. Lucky for you, I'm an excellent stuffer. I ordered some nice ones last night online, and I think they'll be at the venue or something later today." He seemed so proud of the statement, and a warm feeling exploded inside me. "I think we should start with the underwear first, because that might take some time." I nodded in agreement, and headed into a room. Jack stopped the door from shutting with his hand. "Can I come in?" He was quick to explain when he saw my look of horror. I wasn't ashamed of my body, but dysphoria wasn't making me exactly proud of it, either. "I'll face the wall and everything, I just think it might be a bit awkward for everyone involved if I have to tell you through the door how to push your dick down. It took me enough convincing for them to let us come into the dressing room in the first place."
I took a step back from the door. "Fair point."
"You know, this feels kind of backwards." Jack said, setting the bras on the floor and taking his position facing the wall. "I feel like I should be the one putting you in the corner. I'm the adult here, and I missed out on giving you time-outs."
"Oh my god, shut up." I slapped his back. I couldn't help but think how people would take this conversation if they were listening to it from outside a Victoria's Secret dressing room. "People are going to think we're fucking in here!"
He laughed. "Let 'em!"
I dropped nine pairs of underwear on top of the bras and dropped my pants. "Let's just get this over with, dude."
Jack was surprisingly good at teaching, even though he couldn't see how I was reacting. Within about ten minutes, I knew which pairs worked and didn't, and I was ready to move on to bras. Amazingly, this took even less time than the underwear. "How the fuck did you guess my exact size?" I questioned, looking myself over in the mirror. For the first time this week, I felt confident. You could tell that I didn't have boobs, but I knew Jack would help me fix that later. All that mattered was that I had a bra that fit and it was amazing.
"Alex is the first boy I've been with." He shrugged, turning his head to see me. "Perfect! You like it?"
"I love it." I cooed, unable to stop looking at myself. Could I pay for this without taking it off? "I need it."
He grinned and ruffled my hair. "Why don't you take your time trying out the rest of them? I'll wait outside for you, and when you're done we can choose which ones you want."
Half an hour later, we left the store with two bags. Jack insisted on buying me a week's worth of "necessities," as he called them. Now that we had our armor, we could go back and face the dragon of this morning.
And the second time around was definitely more successful than the first.