Jack was nearing town while listening to some very uncharacteristic music. Various musical soundtracks had been bring off of her speaker since the drive had begun. Tracy curated the pylist for her when they were in high school, and she’d always liked to put it on after break-ups to remind her of simpler times. Today, though, she couldn’t waste time reminiscing; she had work to do.

  In the messy back seat of her car, sitting atop all sorts of paperwork, reports, and newspapers, was a bck duffel bag full of various feminine items of crucial importance to Jack's pn, many of which items left behind in her closet by various girlfriends. One of Kacey’s sets of tucking panties, Lacy’s breast forms from before she got impnts, a lingerie set Jack had been pnning to give Stacy for Christmas, as well as several outfits for Tracy and various sex toys. The core of her pn was simple; Tracy had feminine mannerisms, wore feminine clothes, and used to crossdress.. It was the only expnation. Jack ughed to herself, reminiscing about when Tracy would borrow her dresses to py princess. He was definitely trans. He had to be. She had to be? No, Jack thought, it was probably best to respect his pronouns for now.

  She’d done occasional forced feminization rolepy with Lacy, but there was no way to transte that to real life. The options left were either pushing him to confront his identity, or try to trick him into realizing it himself. She figured she’d have more luck with the second; Tracy was very non-confrontational, so she anticipated little resistance to her scheme. Getting Tracy to put on a dress was not, historically, a tall order.

  The details of the pn began to come to her, not that she really needed a pn for this. All she’d have to do is ask him out, and then convince him to crossdress for old times’ sake. It shouldn’t be too hard, Tracy loved crossdressing, and the sweet boy she remembered would take any opportunity to wear a dress. Then, once he’s all dolled up she treats him just like her girlfriend. Jack assumed that this would be enough for Tracy’s “egg” to hatch.

  She tried not to think of all the ways this could go wrong. What if Tracy had a girlfriend? (Or what if h—) What if he wasn’t into her anymore? (What if he’s not—) What if he had a bad reaction to Jack helping him find himself? (What if he’s not trans?)

  That was the big one. What if Jack was wrong? What if there wasn’t some clean solution to this psychosexual fixation she had on her male best friend? Was she just stringing herself along, being unknowing puppeteered by some fetish she was too ashamed to even admit she—

  Her phone’s automated voice decred, “Destination is on your right,” in a voice seemingly synthesized to be as annoying as possible, and she parked at the address Tracy had texted her while she was getting ticketed during her earlier traffic stop.

  Shit. She’d gotten deep into her thoughts and failed to pn out the trans-ing of her best friend. Well, it was too te now. Now she’d have to face the music. It was really time to see Tracy again.

  As she walked to the left door of the duplex Jack thought of when she must have fallen in love. Watching Tracy on stage as Lady Macbeth in one of their school’s gender swapped productions of Shakespeare came to mind. She was so radiant, so confident. A far cry from the timid boy she was normally. For those hours Tracy was a beautiful actress, and those moments were fixed in her mind forever. Jack knocked on the door and waited. She hoped she could keep it together when Tracy opened the door. He was just so pretty; far more so than her exes (not that she’d tell them that). She couldn’t wait to see what estrogen would do to him; if Lacy was anything to go by then he’d be a knockout within the year.

  The door opened and a man was there. He was smiling pleasantly, and his hair was pretty long, but he was a man, and not even a very handsome one. Jack’s stomach dropped, and she was at an uncharacteristic loss for words.

  “Jack!” Tracy squealed, leaping forward into her arms for a hug. “I missed you so much! You have to tell me all about LA and being a private detective. Is it super exciting?”

  Jack couldn’t respond. She hadn’t even considered this scenario. She’d come back, and the spell had been broken. Tracy wasn’t some avatar of transfeminity, he was just a man. The same man she’d broken up with years ago, because even if she loved him as a friend, she couldn’t be more than that.

  She muttered out a reply about it being nice to see him too, but her heart wasn’t in it. This had all been a mistake; break-ups lead to bad decisions, who knew?

  As Tracy led Jack inside, she resigned herself to the idea that her pnning was all pointless. She’d just do her work and catch up with her bestie. Tracy guided her to the kitchen where he filled a measuring cup with water and put it in the microwave.

  “Tea, really? Isn’t that like, disloyal to your coffee shop?” Jack asked. Despite everything it still brought her some joy when Tracy giggled.

  “I see your point, but wouldn’t it be more disloyal to drink coffee from somepce else?” He replied, smiling. “I’m being a most virtuous barista by sticking to tea outside of work hours. Plus it keeps my caffeine intake down. Believe me, waking up as early as I do, it can be tempting to down some espresso every few hours, but that's probably bad for your heart or something.” Jack found herself easing more and more into the flow of conversation. Chatting with Tracy was a bit like riding a bike that way. “I know where you’re coming from, sometimes I have to stay up overnight for work, and I always spend the next day drinking coffee by the gallon. It makes you feel like shit all week.”

  Tracy perked up a bit at the mention of her job, and she began regaling him with lightly exaggerated tales of her PI work. She did have some stories worth telling, but without some generous cutting and tightening of the narrative, they were far too long to keep someone’s attention.

  Jack’d told the stories often enough to do it almost on autopilot. It was a blessing while drunk, but less so here, since the reason she so often told the stories drunk was to pick up chicks. In the version of meeting Tracy she’d imagined, right now Jack would have her arm around his shoulder on the couch, reeling him in and seducing him. This was reminding her of her stupid fucking pn, just like this whole trip was going to. Jack quickly wound up the tale of accidentally discovering a coworker’s infidelity while simply checking a bar’s nightly traffic and resolved to ask Tracy about his job; it would give her a chance to gather herself.

  Before she could ask though, he squinted at her. “Are you alright? You’re looking pretty down.”

  “Oh ya know, just break-up stuff. Sometimes it takes a bit to hit you,” she replied, boriously.

  Tracy brought Jack to the couch and sat them both down, leaning into her to give her a somewhat awkward sitting hug. Jack eagerly returned the embrace with closed eyes. Even if Tracy was just going to be her friend, he was still a kind and comforting soul, and she counted herself lucky to know him.

  When she opened her eyes, and looked at Tracy, his eyes still closed in a sweet and respectful hug, her heart began to race. His skin was too smooth, the red in his cheeks was too regur. He was wearing makeup, and now that she was looking she could see more. His lips were a few shades too pink, and those deep bck eyeshes were either fake or mascara. She was right after all. Sure, Tracy would be a bit of a fixer upper before she’d get pretty, much more so than Jack had imagined in her, in hindsight, definitely lust-addled fantasies. But Jack came prepared for that.

  Tracy, startled by Jack’s sudden change in mood, broke off the hug and leaned slightly away from Jack as she stood up.

  “Tracy, I’d like to apologize for showing up here all mopey. I’m not going to let some stupid retionship drama drag this reunion down. I’ve really missed you Tracy, and I want this to be just like old times.” Jack said.

  Tracy replied in a calm, practiced, tone “Are you sure you’re feeling alright? I want to hang out too, but you’re acting-”

  Jack cut him off, “You know what could cheer me up? Seeing some of your old stage outfits. I know you kept them.”

  Tracy seemed a bit hesitant, like he wanted to ask more about what was up with her, but relented and headed off to his room, while Jack followed close behind.

  Off in the corner of Tracy’s closet, hidden behind several heavy coats, were the dresses he’d worn in the various Shakespeare productions that their high school drama club had put on. Their school wasn’t very big, and only got its theater budget from donations, which meant that some of the kids did their own costumes. In the name of Shakespearean accuracy (kind of) the roles of women were pyed by boys, but since there were only a couple boys in drama, the majority of roles, the roles of men, had to be pyed by girls.

  That is how Jack came to spend several weekends a year during high school watching her best friend, (and briefly, boyfriend) dressed as a woman, being kissed by dies in men’s clothing. Jack was increasingly realizing that her fixation on Tracy must have been brewing for about a decade, which, on the one hand she was gd to know, and on the other hand was somewhat disturbing. Nevertheless, she managed to snap herself back to reality as Tracy held up two old, slightly wrinkled dresses. The one in his left hand, his Miranda costume in The Tempest freshman year, looked comically tiny next to Tracy’s adult body, but the other one, his Lady Macbeth dress, looked like it might still fit him.

  He reverently hung the Miranda dress back up, then turned back to Jack, making a face and posing with the lovely green and blue Lady Macbeth gown. “Like what you see?” He said with a smirk, breaking into a fit of giggles immediately afterward.

  “I do. I would totally uh-” she took a moment to recall the py, “make like a spirit and unsex you right here.”

  Tracy’s giggling intensified, “You remembered!”

  “How could I forget? You were amazing up on that stage! You make for a pretty beautiful actress you know.”

  Tracy flushed at the compliment and took on a pensive look, nodding his head back and forth. “Just a second.”

  He hurried to the bathroom just in time to miss Jack’s smirk. This was going almost as well as she’d hoped it would.

  After a few minutes of Tracy awkwardly grunting in the bathroom, he finally called Jack in to ce him up.

  Now that he had it on, the dress was clearly too small. Jack couldn’t quite ce it up and the bodice seemed to be choking the life out of Tracy as she tried. Tracy was taking their failure harder than Jack, as much as she really did want to see him wearing it again, and after a few minutes of pain tears were starting to collect in his eyes.

  “Tracy, dude, are you alright?” She asked, only half faking her concern.

  “Yeah yeah, it's just… I haven’t gotten to wear anything like this in years, and I guess…” He trailed off and a sob wracked his body. “It hurts to know I never will again.”

  It was Jack’s turn to offer a comforting hug, and she brought Tracy in close to cry into her shoulder.

  “You’re my best friend Tracy, I love you, and I’ll stick with you no matter what. I’m sorry that the dress doesn’t fit you anymore, but you can wear dresses again if you want. I won’t judge you. I’ve seen you wearing them dozens of times.” She calmed her voice, this next part was important, and she didn’t want to mess it up. “I bet one of the dresses in my bag would fit you, if you wanted to wear one of course.”

  Tracy pulled “his” head out of Jack’s shoulder and gave her a puzzled look. “You brought dresses?”

  “Oh, uh, yeah I did. You never know when like, something formal is gonna happen, like a dinner or a dance or something y’know.” She hadn’t been prepared for friction here of all pces.

  The tears had stopped flowing and Tracy was looking at her with a face of utter confusion. “Jack, I haven’t seen you wear a dress since, like, puberty. You didn’t wear a dress to prom. Do you even own any dresses?”

  Jack turned away to awkwardly scratch at the back of her head. “They’re, uh, my ex’s.”

  “The ex who just broke up with you?”

  “No! Or, well, maybe. Yeah.”

  “And why did you bring your ex’s dresses with you on a work trip??”

  “Because…” Jack didn’t want to respond. She couldn’t respond. But Tracy had such a cute, confused look on her his face… She had to say it. “Because I thought you’d look cute in them.”

  The silence that followed her half-confession hung over the two of them for several seconds. Tracy was seemingly stunned into silence and Jack couldn’t bear to turn her head to see her best friend and apparent crush’s expression.

  Tracy managed to gather his composure first, and he managed to utter a quiet “Really?”

  That was all Jack needed, she turned and looked her friend in the eyes, to make sure he she knew how Jack felt. “Really. Tracy, you’re a beautiful, kind person, and you’ve always been there for me. You’ve always made my life brighter and being away from you for so long has made me come to terms with some things. I… I think I love you Tracy, more than just as a friend, but well, there’s always been something coming between us. So, Tracy, if you feel at all the same way I do, could we, just for tonight, try something. Something that might feel weird, and uncomfortable. Could you try it for me?”

  Tracy nodded along rapidly, opening and closing her his mouth, as if struggling for air. “Yes, anything. Whatever you want!”

  Jack swallowed. It was the moment of truth now. No going back, not that she could take back any of this. “Tonight, Tracy, could you be a girl for me?”