“Yes!” Tracy replied, his heart racing.

  Jack’s response was a wide grin and a hug that swept Tracy off his feet and carried him back to the bedroom. Once her joyous dispy was finished, she was a blur of motion. She all but tore Tracy out of the crushing embrace of his Lady Macbeth gown, leaving Tracy trying to cover himself in just his underwear. She realized her mistake and rushed off with a quiet, “I’ll get my bags now.”

  As soon as she left the room Tracy rushed to cover himself with his silk pajamas. Sure, Jack had seen him in his underwear before, but it was different when they were going to kinda sorta maybe be dating again.

  He still couldn’t believe it. They might get back together! It was a Christmas miracle! Yeah, Jack was a lesbian, but she’d seemed pretty sure about loving him. Maybe she was really bisexual and just hadn’t realized! He’d dress like a girl for her tonight and then they’d get back together, they’d be long distance for a while, but eventually she’d move in with him and in a few years he’d sell the duplex for a down payment, they’d get married, (Jack would wear a suit, obviously) and then she’d carry Tracy across the threshold of their new home in a beautiful wedding gown! Wait, that st bit wasn’t quite-

  Jack barged back into Tracy’s bedroom carrying a suitcase and a giant bck duffel bag, with what seemed to be old newspapers stuck to the bottom. She set the suitcase down by Tracy’s dresser, the implications of which left Tracy blushing, and brought the duffel bag to the middle of the room. When she opened the duffel bag, she revealed a pink, rubbery rod (which Tracy supposed must be a dildo) affixed to some sort of harness.

  “Shit dude, sorry. It must have moved during the drive,” Jack said as she pulled the bag towards her and shifted its contents.

  “Why’d you bring a dildo? Were you pnning on hooking up with girls in town?” Tracy said archly. “I know you’re something of a cad but isn’t a backup pn a bit much even for you?” He didn’t often get to see Jack embarrassed, it was an enjoyable sight, at least while it sted.

  She stood, now holding the apparatus and returned Tracy’s smirk. “This is called a strapon. It’s what I use to fuck my girlfriends.” She winked at him. “If you’re a good girl tonight, maybe you’ll get to try it out.”

  All Tracy could do was blush and look away.

  “Now, let's get back on track. You’re pretty, for a boy, but I can fix you up nice and femme.” After scrounging around in the sack for a moment she pulled out a seemingly pin pair of vender panties. “These are tucking panties. They make it look like you don’t have a dick, trans women wear them. And drag queens probably. To wear them right, slide them up to your knees, then push your balls up until they go inside you, I think, then you pull your dick back and slide them the rest of the way until they’re snug.” She held out the pair, and looked at Tracy expectantly after he took them.

  “Jack, I’m not stripping naked and fiddling with my crotch in front of you,” Tracy said, crossing his arms.

  “It’s nothing I haven’t seen before!” She protested.

  “And st time you saw it you broke up with me. Now turn around.”

  That wasn’t the only reason Tracy didn’t want Jack looking. In truth, he was somewhat ashamed of his body. He wasn’t hairy, or fat, or any of the things guys were typically ashamed of, he just didn’t like how he looked. Maybe some casual crossdressing with his ex would be a nice change of pace.

  After a minute of deeply uncomfortable self-groping involving the use of internal tubes he didn’t even know he had, Tracy had put on the tucking panties. The effect was impressive. While Tracy was, at least to his knowledge, not a very well endowed man, he hadn’t expected the degree of crotch fttening he saw looking down. He looked about as ft as any bikini cd dy, and the panties weren’t nearly as tight as he’d feared. They were certainly tighter than any underwear he’d worn before, but they weren’t painful, and only barely dug into his skin uncomfortably.

  “You can turn around now,” Tracy said with a forced neutrality.

  When Jack did, he was a bit surprised at her ck of reaction. She didn’t seem surprised at how well the underwear worked at all. She just gave him a once over nodded, and went back to digging around in the bag.

  “Good work. Now we can get to the fun part,” She said.

  “And what would the fun part be?” Tracy replied.

  Jack smirked up at him, “Your boobs.”

  Tracy’s heart pounded. Boobs? On his body? How would they look? He hoped they wouldn’t be too big, but he also wanted them to be visible on his form. Boobs would go a long way to fixing his awkward, shapeless body. Wait, how was she going to give him boobs?

  His question was answered when Jack held up a flesh colored teardrop made of silicone, and then its pair. Colorwise, they matched his pale skin well enough, but he wasn’t really sure how they’d end up looking like boobs.

  “You hold these for a bit while I grab the wipes and tape.”

  She was going to tape them to him? “You’re going to tape them to me?”

  Jack rolled her eyes. “It's a skin safe, double sided adhesive tape. Don’t worry, they won't fall, you’ll be wearing a bra too.”

  Tracy blushed and looked away, but took the silicone boobs.

  When Jack stood back up she had the rest of the equipment, including a white bra with pretty full coverage. Tracy wasn’t familiar with any bras that completely covered the breasts like that, maybe it was vintage, or designed specifically for wearing fake boobs.

  Sticking the boobs to his chest was very uncomfortable, but it gave Tracy a reason to shave his chest, and everything else below the shoulders while he was at it. He liked the feeling of being smooth, but he didn’t usually have a reason to bother. He hadn’t done it in a while, so he probably missed a few spots, but being blonde had its advantages.

  “Ready for your ‘boob job’ Tracy?” Jack said, brandishing the breast forms.

  Tracy blushed. If he was a woman he’d never get a boob job, he thought. They looked so tacky. Well, maybe if he was really ft. There wasn’t actually anything wrong with wanting to be more comfortable with your body, even if there were a lot of pressures in society to conform to the expectations of your sex.

  Actually taping the boobs to himself left an odd tightness in Tracy’s chest. The obvious falseness of them, sitting there like a mockery of a woman’s body, left him breathless, and he closed his eyes as Jack picked up the bra. She seemed to notice how he was feeling, and quieted down for a moment.

  Putting the bra on was far more intimate than Tracy’d anticipated. The boobs were silicone, fake, but in the bra, they looked real enough. As Jack pulled the csps shut, she leaned into him.

  “You’re coming along nicely babe, take a look at yourself.” She whispered.

  Tracy looked down at his chest, and saw his modest bust concealed in the pin, white bra. His head swam and he fell backwards into Jack’s arms. Dizzy, he just id there for a moment as feelings he didn’t understand swirled through him.

  “-orry baby. I’ve got you. Just let yourself feel whatever you’re feeling. There’s-” Tracy was dimly aware of Jack speaking, but she gave him all the permission he needed to let his mind drift off.

  Why was he feeling like this? He’d liked wearing women’s clothes when he was younger, but that was because of the acting. Well that and dresses were just prettier than anything boys got to wear.

  Jack guided him to the bed and sat him down.

  This was different though, he hadn’t even gotten to put on the dress yet. It was the underwear, something he’d never even thought of trying on. He knew there were perverts who liked to dress up as women during sex, but this didn't feel sexual. He wasn’t really sure what it felt like.

  Jack sat behind him and massaged his back.

  It was a good feeling though. He knew that. Like a massage, a kind of relief that fixes things you didn’t even know were bothering you.

  “I understand if this is too much for you. We can stop now if you want. You don’t have to go through with this.”

  No. He needed this night to keep going. He loved how he felt. How the underwear made his body look. How he looked like- How he felt like- How he got to be a girl. Just for tonight, Tracy thought, she got to be a girl for Jack.

  “Tracy? Tracy are you alright?”

  But Jack was worried now. (Worried about her,the butterflies in her stomach reminded her) Tracy was going to have to do something to fix this, assuage her concerns, otherwise she might not let things continue.

  Tracy pivoted, sideways to Jack now, and wrapped her arm around Jack’s shoulder. She turned to look her best friend right in her worried, anxious, searching eyes, and knew what she could do for Jack.

  She twisted her body and all but lunged into a kiss.

  “Thank you. So much. I love you.” Tracy said, gasping, in the moments her lips parted from Jack’s.

  Jack was too surprised to react at first, but soon her hands were wrapped around Tracy’s waist and she was kissing back just as passionately. Soon she got tired of just kissing though, and she grabbed Tracy by her ass and lifted her up into her p. “I knew it. I should have seen it sooner. You were a girl all along. All you needed was a little direction.” She growled.

  What was Jack talking about? Was this like, some kind of sex rolepy? Whatever, Tracy could py along. She pitched her voice up a bit and spoke from the very top of her throat, like she’d learned when learning her lines for Macbeth. They didn’t let her do it for the actual py, or even rehearsals, but she still remembered the skill.

  “You’re right Jack. Thank you. Thank you for making me a girl!” She moaned, as Jack’s grip tightened on her ass.

  That must have been the right thing to say, because Jack threw her onto the bed, and crawled on top of her, one Jack’s hands remained low though, and slid up Tracy’s thigh to brush against her dick.

  “I wouldn’t want those panties to start hurting, at least not yet,” Jack said, winking, “so let’s take a break and finish this ter. I’ll get you all dolled up for our date, then I’ll treat you to your first time as a woman.”

  Tracy didn’t even have time to be scandalized by Jack’s offer to take her virginity. “A date?!?”

  “Yeah babe, I’m taking you out on a date. You’re my girlfriend tonight.” She said with another wink.

  Tracy couldn’t do that. It was one thing doing this with Jack, but… “What if someone sees me?”

  “I know it can be hard being seen as a woman the first few times, but really, most people won’t be looking close enough to recognize you. Plus, you’d be doing it for me. Don’t you want to be a good girl for me?” Jack said, gently stroking Tracy’s dick through her panties.

  First few times? Tracy still felt like she was missing something, but she couldn’t resist Jack’s… (was feminine still the right word for a woman as butch as Jack?) wiles. She could still negotiate at least.

  “Well then you’d better take me somewhere nice, where I won’t see my coworkers. If I’m going to be your… girlfriend… then I at least expect to be pampered,” Tray managed to say, through the thudding in her chest.

  “I wouldn’t have it any other way,” Jack replied, not missing a beat. She followed her line up with a kiss that left Tracy flustered once again.

  Somehow, despite Jack being the one to awkwardly confess feelings for her, Tracy didn’t feel like she was in control of this situation at all.

  “Now, before I forget,” Jack said, reaching into her duffel bag of mystery once more, “eat these. They’ll be important for… They’ll be important ter.” She handed Tracy a small package of fiber crackers, which Tracy scarfed down with the aid of a few sips of tea.

  She was curious about what on Earth Jack meant, of course, but doubted she'd get a straight answer without fighting for it, and it was hardly the weirdest bit of this whole exercise.

  Jack set the game of grown-up dress-up back on track by revealing a bag full of various makeup products, and proceeded to be confused by the look of disgust on Tracy’s face.

  “Those look used. Did you bring your ex’s makeup too?” Tracy said, accusingly.

  “Uh, yeah. What’s the problem? You’re already wearing her…” Jack cut herself off, “You’re already going to be wearing her dress.”

  “A dress is just clothes, Jack. You can wash a dress. You did wash it, right?” Jack nodded, bashfully, “Makeup though, it gets all over your face, you’re constantly touching it, the bottle, your face, over and over again. It gets dirty, covered in germs. It’s unsanitary to share makeup. Didn’t your mom ever teach you that?” Tracy waited expectantly for an answer while Jack looked to the side and scratched her head.“

  “Probably yeah, I don’t remember though. I don’t really wear makeup.”

  “I know”

  “Maybe you could teach me?”

  “Would you ever wear it if I taught you?”

  “Uh, probably not, no.”

  Tracy sighed and rubbed her forehead. “Well Jack, lucky for you I do know how to use makeup, and have a fair bit of the stuff here, so why don’t you tell me about the look you had in mind and I’ll see what I can do?”

  Jack just stared at her dumbly.

  Tracy waited for a response.

  Then waited a bit more.

  Finally, in a near whisper Jack said, “You know… like… makeup? Like how women do for dates? You put the stuff on and it makes you sexy? I know there’s lipstick and mascara and eyeliner. Or is it called eyeshadow? One of those.” A bit more confidently she added, ”I’m not stupid, I know you’re wearing some makeup now. I’m just, uh, not totally sure how much.”

  Tracy examined Jack, worrying her lip. Jack was cute like this, she looked bashful and even a bit embarrassed. It was another glimpse at Jack without the yer of bravado she usually wore. Jack, as only her best friend got to see her. Jack, as a partner, a girlfriend would get to see her. The warm feeling in Tracy’s chest that had been growing all night burned like a fire, filling her with confidence and determination.

  “Don’t worry,” Tracy said, giving Jack a little peck on the cheek, “I know what you mean. You stay out here for a bit while I get all made up for you. I want my new look to be a surprise…” She trailed off with a giggle.

  ***

  Actually doing a full face of makeup was harder than Tracy thought it would be, but she enjoyed the challenge. She was noticing something else though, as she worked on her face, she liked this. She already knew she liked wearing makeup, of course, but that was different. It was a “natural” look, just to touch up her best features or smooth out some fws. This though, a full face of date night makeup, complete with a bit of contouring, was more of a statement. It wasn’t something a man did, Tracy thought, with an excitement that seemed to go beyond just breaking a taboo.

  On some level she had wished for an opportunity like this, it's why she had bought this kind of makeup in the first pce in addition to her daily routine, but doing now, for a date with Jack was making some things clearer. There were things she’d been grappling with that she’d never even known to confront. Here now, performing femininity in a way far more intimate than she’d ever had to on stage, Tracy felt comfortable, more comfortable, maybe, than she felt in day to day life…

  Well, no reason to keep Jack waiting. Tracy left the bathroom, cd in just underwear and a full face of date night makeup, feeling every bit of the implication of those facts. She also felt Jacks stare. While initially her friends face had lit up brightly, that was quickly repced by hunger as Jack’s eyes traced her up and down. For the first time in this night of partial nudity, Tracy felt exposed.

  She hurried to the bed, feeling Jack’s eyes on her ass the whole way, and grabbed the dress. It was going to be her outfit for the night, and while she was certainly gd for the opportunity to wear a dress again after so long, she was a bit disappointed that she wasn’t more drawn to the garment. This wasn’t like the pretty gowns that had captured her imagination in theater. It was pin, just a red, A line midi dress with a bit more coverage at the bust than she usually saw in the style and some ruffling in the skirt and shoulders. It was hardly casual, but far from truly formal. It looked like any other dress you’d see a woman wearing for a nicer date, but that was the issue Tracy wasn’t really a woman. There was no way she could pull this off with her body. Back in school, on the stage, things were different, a big, fancy dress covered her. It hid her body and repced it with its own beauty, but this was meant to ftter someone, to compliment their body rather than hide it. On Tracy, it would just exaggerate her maleness and that would… hurt? Why would it hurt? Whatever, she was getting increasingly insecure over her best friend’s leering, and it would be better than being naked.

  Tracy stepped into the dress and waited for Jack to zip it up. The moment had a finality to it. Seeing Tracy like this would break whatever spell had befallen Jack, and that would be it. No more magical night. Tracy turned, looking down at her feet and bracing herself mentally for what was to come.

  She was therefore left entirely unprepared for Jack pcing a finger under her chin and lifting her face to meet her eyes. The tears that were welling in Tracy’s eyes were cut off by Jack’s, “You’re beautiful,” and a gentle kiss. Which Jack followed by guiding Tracy right back to the bathroom.

  Tracy just looked down at the counter for a while, still afraid of ruining the magic for herself, while Jack released her hair from its ponytail and began brushing. Well, she thought, there was no use avoiding it. She looked up.

  Tracy was stunned. She hadn’t given herself and Jack the credit they deserved. The dress she was so terrified would look ugly and shapeless hugged curves she hadn’t even had that morning elegantly. Rather than ruining the illusion of Tracy’s womanhood, the dress completed it. All she could do was stand dumbly, examining the dress in the mirror. How the ruffles hid her shoulder, how it clung tightly to her waist but fred out enough to cover her ck of hips, it even emphasized her bust despite not revealing any cleavage that would give away the false breasts.

  It was like the dress was made for her. Made to make Tracy specifically feel beautiful and warm and giddy, in ways even the gowns of her past hadn’t. That didn’t make sense though, Tracy wasn’t really a woman, why would Jack’s ex have a dress that fttered Tracy like that?

  Jack’s ex must… must have been… trans… then… That would be the only way. It would also expin how the hell Jack knew about tucking panties and breast forms and god knows what else. And, Tracy thought, she brought them for me. Said she loved me, even though she’s gay. The expnation stared Tracy in the face.

  Did Jack think Tracy was transgender? Was she right?