waterlily3402

  Jack drove Tracy into town carrying what she knew was an air of mostly unearned smugness. Sure, Jack had gotten Tracy to realize that she was a trans woman, but that was more in spite of Jack’s pn than because of it. Still, it was done, and while Tracy was obviously nervous, she also looked just as excited as Jack was.

  Jack examined her date once more, lustfully, yes, but tinged with more than a little pride. Just a few hours earlier Tracy was a man, but now she was already the most beautiful woman Jack had ever seen. Not that Jack could take all the credit, the effect wouldn’t be half as good without Tracy’s lovely makeup, and it would probably be overly generous to herself to say she could have done Tracy’s face up even half as well.

  She knew now that her impulse had been correct. She and Tracy were always meant to be together. Those other girls had been mere reflections of her true love, the passion fading quickly to the purely physical as they got more serious and Jack came to know them better, right up until the girls realized Jack was using them.

  Even the physical component of her old retionships now seemed worthless, Tracy was still pre-hormones and yet was already almost as pretty as… who was her best looking ex? Lacey probably, she had gotten impnts a few months after they started dating and she made them look phenomenal. Tracy looked almost as good as Lacey did pre-impnts, which ain’t bad for a pre-transition doll.

  It was too bad that it took tits so long to grow in. Lacey was by far the bustiest tgirl Jack had ever been with and she’d gone pretty modest with the impnts. Jack’s thoughts wandered back to Tracy; even if she started hormones today it would take something like a year for her breasts to really be noticeable. Maybe Jack could persuade her to get impnts. She could afford to pay for them. Being a big business sellout instead of a noir protagonist came with some perks.

  “Are we close babe?” Jack asked, already knowing the answer; she just wanted to hear Tracy talk.

  “Yeah! Just take a right at the light, it’ll be on the left in like, a block.” Tracy responded perkily, despite her continued fiddling with the hem of her dress. Her voice sounded like sex, sweet and bubbly, but slightly hoarse and husky at the same time, like a good girl gone bad. Jack remembered when Tracy had first learned to voice train, following video tutorials on Youtube and trying to impress Jack with her script reads in girl voice. Impressed wasn’t the way Jack would describe how those nights up in Tracy’s room made her feel, though.

  After pulling in and parking further from the restaurant doors than she really had to, Jack got Tracy’s first night out as a woman started right by opening her door and offering her arm. It was all good fun to dote on Tracy that way, but she also certainly needed the help. She looked like a baby deer with how unsteady she was in her heels, and Jack loved how dependent it made her.

  Tracy looked nervous too though, and clung to Jack for emotional support in addition to the physical needs of her legs. Jack steeled herself; she had to do this right. Tracy’s first night as a woman had to be perfect, lest she fall back into the closet Jack had saved her from. Plus, breaking up with Tracy after this would absolutely destroy their friendship; better to keep Tracy transgender, for both of their sakes.

  “Don’t worry baby, even if someone you know is there, there’s no way they’ll recognize the beautiful girl I have hanging off my arm tonight as the theater kid from high school.” Jack said, lying. Tracy was absolutely recognizable if you actually looked, but most people move away from ski towns like she did, and nobody was likely to look anyways.

  The words comforted Tracy nonetheless, and she chanced a, “Thank you baby,” in her girl voice as the pair walked through the doors.

  The hostess was a nice looking blonde woman. A bit light in the chest area and tall for a woman, but that’s just how Jack…

  Wrong time to be ogling women who looked like Tracy. Fortunately, Tracy herself was distracted by the hostess’s “Enjoy your date, dies,” after leading them to their reservation and didn’t notice Jack’s staring. Still, a mistake she couldn’t afford to repeat.

  Jack couldn’t mess this one up. It was a cruel thing to think, and she knew it, but Tracy was different from her exes. She actually cared about Tracy. More than as a fuckbuddy, or even just as a girlfriend. Jack had, perhaps, been too hard on herself, it wasn’t that she hadn't cared about her girlfriends, it was that she hadn’t cared about them as more than that.

  Done riding the high of being gendered correctly for one of the first times in her life, Tracy grabbed her menu and looked at Jack, meaning it was time to turn her charm back on.

  “I’ve never been to a pce this fancy before, do I have to like, order differently?” Tracy asked, cocking her head adorably.

  “Just leave the ordering to me babe, no need to worry your pretty little head about it. The real important part is the wine. Red or white?”

  “I’m actually pretty fond of rosé.”

  Of course she was. “Of course you are,” Jack replied, winking, as she scanned the wine menu for a pricey, but not too pricey, bottle for them to share.

  “A steakhouse with meals more expensive than my grocery bills, do you big city types treat all your dates like this?” Tracy asked, giggling.

  “Only the really pretty ones.” Jack replied, leaning forward to let Tracy take a little peek at her cleavage. Judging by how Tracy blushed and looked down at her p, Tracy had taken it. She smirked, and not just on the inside. Time to press the advantage.

  “Have you been seeing any lucky dies out here recently? Or were you just waiting for me to come back and sweep you off your feet?” Jack asked, winking.

  At that, Tracy blushed furiously and looked away, fiddling with the skirt of her dress.

  “Well I- uh I’ve dated a couple of women since I moved back,” Tracy tried to chuckle, but her voice cracked and it came out a squeak instead, “but nothing like, serious or anything.”

  “Oh, so you were waiting for me then?”

  “Of course not! You’re well, you know gay and-”

  “And you’re a girl. A girl who’s been pining after me since she left. I should have come back to visit sooner.” She should have, Jack realized. She was so caught up in her own world that she hadn’t visited her best friend for years. Maybe she would have even picked up on Tracy’s gender, at least after her first few flings with trans girls. Maybe they’d already be together, sure, but more importantly Tracy would be herself.

  Jack could see the way that the awkwardness was fading away, Tracy was getting more and more comfortable being herself, in public even! Jack had to admit she was shocked at how fast Tracy had realized she was trans. She had been pnning on breaking her egg, sure, but Tracy coming out in under an hour while they were making out was still unexpected. Just went to show how good Jack was at this trans stuff.

  “Pining since before I left, actually. Ever since we broke up. Probably have to come clean about that if we’re gonna get back together.” Tracy said, gncing down at her p shamefully.

  Jack’s heart tightened. If only Tracy had known back then, they wouldn’t have to have been apart, like they were for far too long. That was the part of cisnormativity that was most horrifying to Jack, the not even knowing who you were and the way society conspired to keep you ignorant.

  “I think I’ve been pining for you too for a while, even if it took me a bit to notice it. I-”

  The waitress arrived, Jack ordered the wine and appetizers, and the new couple got swept up in the fun of fine-ish dining.

  ***

  Jack all but carried a very drunk Tracy back to her car. Between most of the bottle of wine she’d ordered (Jack only had a gss since she was driving), and a light dinner of soup and sad, Tracy was pretty far gone. She’d seemed like something had been bothering her too, though Jack couldn’t precisely decipher what. Jack would think that discovering you were transgender and having your first night as a woman would be a joyous experience, but she really wouldn’t know. Nevertheless, Tracy had seemed excited about their night, so Jack was going to keep it going. She could address whatever Tracy was feeling afterwards.

  She looked over at Tracy, who noticed her gaze and giggled. Some of it was certainly the booze, but Tracy looked rexed in a way that Jack had never seen before. Most people wouldn’t have noticed it about Tracy, but she always seemed to have something of a shell separating her from the world. She wasn’t shy or withdrawn like Jack had learned many pretransition women were, but she still separated herself from the world, if only a little, and kept her true self hidden. At some point, back when they were kids, Jack had chalked it up to Tracy having a crush on her, but the shell never left her friend in the, admittedly, short time they’d dated. She realized now what a ridiculous, self centered idea it had been, that she was the cause of what troubled her best friend; she wished she had known then what she did now, and could have helped Tracy a decade ago. But she hadn’t known, and she’d been too busy with her own self discovery to help Tracy’s. Now was different though, now she could make things right.

  ***

  Making things right would, tonight, mean fucking Tracy. The girl of her subconscious dreams deserved to feel like a woman, and Jack knew from experience that fucking a girl through the mattress could be very euphoric, in every sense of the word.

  Guiding Tracy up her steps and through the door, Jack’s mind was occupied by the least sexy part of sex: bottom prep. Tracy (probably) had no experience bottoming, which she’d pnned for, having brought her smallest strap on (in addition to some bigger ones motivated by pure wishful thinking) which meant once she sobered up Jack would have to expin to her how to bottom prep without completely killing the mood. Still, if all went well Jack was going to be her best friends first time as a woman, and the thought of getting to have Tracy like that was starting to leave a mark on her underwear. Maybe she’d brew some tea, get Tracy sobered up a little faster, that couldn’t hurt.