Chapter 6 – The One Where They Go Shopping
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Completely unsurprisingly, Tony and I absolutely wanted to go clothes shopping. Obviously we would need outfits for our new bodies, and this gave us both the option to establish ourselves as two people who were definitely actual trans girls who weren’t secretly regular guys pulling a prank. As a tiny added bonus, like a really tiny one, the tiniest, we would get the opportunity to try on new outfits to go along with our new bodies. As it just so happened, on the car ride there I could think of little else. But that was fine; it made sense for me to hyperfixate on such a tiny bonus. Both the other reasons we wanted to go were more out of obligation and maintaining the illusion, the last reason was something I actually wanted. Besides, what guy wouldn’t want to see a pretty girl dress up in cute clothes?

 

So obviously, as Tony, Rachel and I sat on the bus, chattering away, the atmosphere was quite upbeat. What surprised me though, was just how well I was taking to this whole pretending to be a girl thing. Part of me had wondered, in the back of my mind, whether some fundamentally male part of my brain would have shone through and revealed the ruse for what it was. Instead, however, Rachel, Tony and I were talking as normally as ever, except the topic had shifted. Still, I didn’t mind the topic one bit.

 

If I were to be honest with myself, it might have even been a bit refreshing compared to that forced, overly dudebro posturing I had to take on when it was just me and Tony. I hadn’t realized just how exhausting it was until I didn’t need to do it anymore, but part of me was kind of dreading the next time it would be just Tony and me alone together. I’d have to treat him like my ‘bro’ and he’d treat me like his, whereas so long as we were forced to keep up this image as girls I could just talk like a normal human being. Admittedly, I’d have to talk like a normal human being about—girl stuff—but I didn’t really mind that.

 

Casting my gaze upon Tony, our eyes met, and he flashed me a bright smile, then a wink, causing my poor heart to leak right out of me. Why the hell did my best friend have to make such a pretty girl? Turning back to Rachel, he continued. “Yeah, I don’t know, I guess I didn’t realize just how much I needed this until after I had it, you know? Like before I realized I wanted to be a girl, I felt fine with being a guy, not happy, but resigned. It was just how things were. Now though, everything feels so great and exciting and freeing.” Damn, that was a really good speech; did he just spin that off the dome? It was weirdly relatable, too. Turning back to Rachel so as to gauge her reaction, I saw her nodding thoughtfully in response to Tony’s anecdote.

 

“Yeah, that definitely makes sense. I’ve heard that can be a really common experience for trans people,” Rachel mused. Now, I’ve known Tony for a long time, and, girl face or no, I’m quite familiar with his many looks. As such, I was very able to recognize his ‘I’m internally gloating to myself’ grin. And I was also able to recognize the moment it started to fade into one of bewilderment.

 

“W-wait? Really?” he said, voice trembling a little.

 

“Oh yeah, I’ve heard from uhh, from a friend that lots of trans girls are able to tune out their dysphoria before they realize it's there, but as soon as they do realize it's there and that they’re actually more comfortable being women it becomes impossible to ignore.” As Rachel finished speaking I straightened out and turned my gaze to focus on her. I’d only been half listening, but it sounded to me like she was saying trans people could actually not really feel a ton of dysphoria before realizing they were trans? And that couldn’t be right, could it?

 

“I-Impossible to ignore? Really?” Suddenly the ease and confidence Tony had been exuding only moments ago seemed to be evaporating before my very eyes. But like, not impossible impossible, right? And all trans people totally had to feel dysphoria really strongly before they realized, right? I mean, what did Rachel know? She was a cis woman; she couldn’t actually understand what it was like for someone like me—wait a second.

 

“Oh yeah, super impossible, I mean, think about it, the idea of having to be a guy again now just sounds, awful doesn’t it?” Rachel asked. Tony’s face fell.

 

“Uh, y-yeah. It does sound pretty awful,” he murmured, sounding dejected. And damn, he was such a good actor. He really did look absolutely wiped out by the idea of turning back. Personally, I really didn’t want to think about that, I was having too much fun pretending I was a girl, so I did my best not too, lest it actually make me feel bad.

 

“Oh, gosh, Penny, I’m sorry. I shouldn’t have said that. It was probably really unpleasant to think about that, wasn’t it?” She gently lay a hand on Tony’s knee, squeezing it. Tony just nodded with practiced solemnity. “Well, what about you, Heather? Did you have anything you wanted to add? Maybe something to liven the mood? I kind of ruined it.” She gave me a pleading look, and I froze as my brain tried to come up with a convincing lie. It wasn’t working. Instead I just decided to open my mouth and hope the first thing that came out would be convincing.

 

“Oh yeah, I definitely agree. Looking back, I can’t believe just how long it took me to realize. I was so unwilling to look inside myself and just accept that I was a girl deep down, but now that I’ve done it, I’m so much happier.” Damn, that actually sounded pretty convincing. Hell, if I didn’t know better, I’d almost say I was convinced by it. What do you have to say about that one, Tony? I can come up with really convincing performances too. And, judging from the look on Rachel’s face, she was totally eating everything I had said up. Check and mate.

 

“Well, you both certainly look happier.” Rachel swept her gaze between Tony and I, beaming at the two of us and and wait—we did? “Honestly, both of you could get so mopey sometimes, Will and I had started to worry about the two of you. Seeing you both like this, though, it just all makes so much sense now.” On the one hand, I was relieved; we were really doing it, the prank was going off without a hitch. On the other, really? Were we that convincing? Did we seem that much happier? Honestly, I hadn’t even been thinking about that aspect of it; I was mostly thinking convincing equals act girly, not convincing equals act happy. Then again, girls are associated with giddy-ness and the like, so maybe I was just pulling that off really well. Plus, I was really excited to have this experience, so it would make sense that I’d come off as happier. I relaxed. For a second there I was worried, but clearly everything was both normal and fine.

 

“Thanks!” Tony chirped, casually relaxing into his seat.

 

“And not just happier, I’d say looks-wise in general this was an improvement, though, maybe I’m biased.” Her eyes darted from Tony then to me, fixing me with a half-lidded gaze and a lopsided smirk. I found myself hoping our stop wasn’t coming up because I’d have a hard time getting my legs to work, what with them having become some sort of meat pudding. 

 

“Thanks,” I squeaked, trying and failing to break her gaze as my cheeks flushed bright red. Rachel just chuckled casually, and resumed the conversation as though nothing had ever happened. God, how had I never noticed just how sexy her confidence was? Probably mostly because before her flirtations weren’t aimed at me. I endured the rest of the bus ride trying my best to avoid too much attention from Rachel, or Tony for that matter. He may have been a guy deep down, but that didn’t change what my heart did every time he smiled at me, which was a lot. A lot a lot. More than he probably ever had. Obviously he had some ulterior motive in doing so; what was his plan? I’d get to the bottom of it, and hit back with a plan of my own, no question.

 

Next thing I knew, the bus had stopped, Rachel had motioned us to follow her, and she led us off and away, making a beeline for a nearby department store. We entered the building to find, well, a department store. What did you expect, some kind of flowery description full of clever metaphors? It’s a fucking department store. It sells clothes. You go there, and you buy clothes. That’s it. There’s nothing special about it. Nothing special beyond its core function, that is. And, to be honest, while my experiences in such places had historically been lukewarm at best, downright excruciating at worst, this time around it did feel pretty exciting. The reason why was obvious, I would get to try on all kinds of new clothes to win a prank. Anything could be exciting when it involved totally pranking your roommates into thinking you’re actually a trans girl. Especially things involving indulging in how cool the girl body you got to inhabit along the way was.

 

That did leave a problem, though: winning this bet required a delicate balancing act. If Tony was anything like me, which he definitely was, he was most certainly strategizing for how to pull one over on me and win our bet. He clearly wanted to convince our roommates of his desire to be a girl as strong as mine. Or, rather, he clearly wanted to beat me at convincing our roommates of that desire as badly as I wanted to beat him. Meaning that, if I went too hard into femininity he might feel threatened and double down even harder. And yeah, obviously I could double down right back, but that would just lead to some sort of girly arms-race. And, as fun as that sounded, I didn’t want to overdo it. Obviously if I over-did it, Rachel and Will would realize the truth of the matter. So, I needed to strike a middle ground, and possibly find a way to trick Tony into thinking he was winning the bet. If I got him to relax and feel comfortable with a false lead, I could go in for the kill. He’d never see it coming. That was the difference between me and Tony, he just didn’t have the foresight and awareness that I did.

 

With all that in mind, I formulated my plan; it would take a second shopping trip, but it would all be worth it. First things first, on this trip I would buy only more androgynous or butch clothing, thus lulling Tony into a false sense of security. Then, when he least expected it, wham: I hang out with Rachel and Will without him in the frilliest, girliest clothes I can possibly find after my second, secret shopping trip. As it just so happened, this plan also insured me against any possible judgment from Tony. ‘Cause, obviously, we were still regular bros, and he was probably actually not nearly as into this whole ‘being a girl thing’ as I was. Honestly, I wouldn’t even be surprised if he picked similarly butch styles to myself due to the idea of dressing like a girl causing him discomfort. That would be ideal, honestly, as it would make my own victory that much easier. 

 

Confident in my plan, I set off with Tony and Rachel into the women’s department, then split off from them both toward the more alternative looking styles. Fortunately, I didn’t look at all out of place in that section, as Rachel had loaned Tony and I a set of somewhat ill-fitting girl clothes each and she was definitely a proper punk-babe. Forcing myself to avoid things like the cute edgy skirts and crop tops, I stuck to the classics: skinny jeans, muscle-tanks, blazers, button ups, jumpsuits. 

 

Honestly, the clothes definitely worked for me. I looked good in them, good enough to have me posing and winking at myself in the mirror. The problem was, though, the girl body I’d been given had way too much of a bubbly, fluffy energy to her to look nearly as badass as my choices would suggest. I’d tried making a series of serious and aloof faces, but just wound up giggling at the fact that this was how I looked. Obviously just because it was so funny. It was such a good prank and Rachel was totally eating it up; I was so excited to keep it going.

 

Settling on my choices, and giving one last long look at the more femme options, I shrugged, and set off to reunite with Rachel and Tony, who had stuck together and tried to insist I do the same. For my plan to work, though, it was necessary for me to split away. Deeper into the women’s section, where the more catch-all clothes were, I found Rachel, casually examining a pair of jeans with a look in her eye that suggested she was considering the best way to steal them. I cleared my throat and she turned about to me, then motioned me to open my bag. I did so, and she peered inside, then raised her eyebrows. “All done?” 

 

“Yep!” I grinned brightly at her surprise. I was willing to take a bit of confusion early on if it would pay dividends later. “I’m happy with all of my choices, don’t want anything else.”

 

“Hmm, didn’t really think that’s what you’d go with,” she mused.

 

“Oh? And what were you thinking?” I asked, trying to keep from giggling at the brilliance of my plan. It was bulletproof, really. Tony would never suspect a thing and the winner of best at being a girl would be me.

 

“”More something along the lines of what Penny chose,” she said casually. I couldn’t help but wonder what that meant. My best guess was that, what with Tony being a guy who probably felt awkward leaning too hard into being a girl, and what with him probably not being super familiar with women’s fashion, he had probably picked some outfits which were either pretty boring, or kind of ugly. I was about to ask Rachel to elaborate, when something seemed to grab her attention in the direction of the changing room. “Oh, there she is now.” Rachel nodded toward Tony, and I followed her gaze, ready to see what kind of awkward outfit he’d come up with. 

 

I was greeted with an absolutely stunning sight. Tony was dressed in this gorgeous looking pale blue sundress that hugged his curves tightly and left his tanned shoulders bare. Its front was dotted with large, fashionable buttons, and the skirt stopped just below his knee. His hair was fixed with a little bow, and a dark, woody red—faux—leather purse hung across his body from his right shoulder. His smile was absolutely radiant, and as he stopped before Rachel and me, playing with the hem of his skirt as he swished side to side, a peculiar, unwelcome feeling rose within me. 

 

And okay, yeah, fine, he fucking nailed that outfit. But that didn’t mean anything, Rachel had probably picked it out for him and he was probably smiling too wide because he thought the whole thing was hilarious; there was no way he’d actually be caught dead in it, though, right? Rachel elicited a low whistle. “Wow,” she breathed. Hey, what about me? my brain seemed to scream. “You know, Penny, I wasn’t so sure at first. I thought it was a little too, I dunno, plain-looking? But you were right. You wear the hell out of that thing. I’m sorry for ever doubting your keen fashion sense.” She stuck her tongue out a little, and Tony giggled, doing a little twirl as the skirt swished with him. That unwelcome feeling surging stronger than ever. Rachel couldn’t be serious, could she? Tony had actually chosen that dress? He wanted that to be his aesthetic going forward? But wouldn’t that mean I…? I…. “Doesn’t she look amazing, Heathe—hey, what’s wrong?” 

 

“I—I think I want to try on a few more outfits.”

 

Gosh, I wonder what that was about? I mean, what red-blood cisgender heterosexual man wouldn't want to wear cute dresses? I hope you're enjoying the story so far! If you're aching for more now rather than later then guess what? You can read all of this story on my Patreon right now for as little as $2 a month. You'll also get a bunch of other stuff. Like, for example, patron exclusive bonus chapters (and smut), audio readings of some of my steamier works, access to my official discord server and (and I can't stress enough how valuable this last one is) Pictures. Of. My. Cat. Ziggy. There's a bunch of other cool stuff over there, but we'd be here all day if I listed it all.

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