Tracy could get used to this “being Jack’s girlfriend” thing. Her friend had spent the night opening doors, pulling out chairs, offering her arm, and otherwise doting on Tracy. The blonde’s euphoria was not entirely Jack’s fault however, as she’d drunk enough wine over the course of her date to leave her feeling more than a little floaty. Floaty enough that she’d floated right out of her body and spent most of the car ride back home unconscious. That was another benefit of her new girlfriend; she could get as wasted at a restaurant as she wanted.

  The unforeseen (though certainly, in hindsight, foreseeable) benefits were starting to really pile up. After helping Tracy inside, Jack had immediately got to work on tea to hydrate and sober up Tracy, which was kind enough to nearly bring tears to her eyes, even if she wasn’t entirely sure she wanted to sober up.

  Getting drunk off most of a bottle of wine hadn’t been an accident. She’d thought that getting drunk would quiet the thoughts that had troubled her on the drive to the steakhouse, and she had been half-right. The thoughts hadn’t left her, but warm and floaty they were much less troublesome.

  Jack arrived with Tracy’s favorite mug (an “ironic” piece featuring a simple depiction of a cat and the words “hang in there”) containing a hard to identify tea with a chemical note in its scent that identified it as medicinal in some way. The clearly medicinal tea earned a questioning look from Tracy, but she took the mug anyway, the booze was starting to wear off and she’d crossed the hump beyond which her buzz was more annoying than fun.

  “And what’s in this drink? You really don’t need to slip me anything, you’ve already brought me home,” Tracy said, winking at her friend.

  Jack scratched her neck for a moment before shaking her head slightly, restoring her typical confidence, in a dispy Tracy doubted she realized was as obvious as it was.

  “It's a xative tea.”

  “Why on Earth are you giving me a xative tea? Is this some secret feminine ritual I’m unfamiliar with?” Tracy said, confused, but enjoying the banter.

  “Yes and no, some kinds of girls are more familiar with this ritual than others,” Jack replied, smirking.

  “Which kinds of girls do you mean?” Tracy was starting to get confused, again, Jack was putting on her flirtatious voice, a huskier affect than her already deep-for-a-girl voice, for the sake of discussing tea.

  “Pretty girls.” Jack leaned in, she was the same height as Tracy, but with her friend seated Jack towered over her, and used the opportunity to the fullest. “Girls I intend to fuck.”

  Tracy squeezed her legs together, face flushing. “What- what do you mean?”

  Jack’s smile was predatory as she pced her hand upon the back of the couch to lean even closer to her test conquest. “You’re not my first trans girl Tracy, and you didn’t think I was a bottom, did you?”

  “Bottom?”

  “We’re both girls Tracy, lesbians aren’t, well, straight. There’s no ‘woman’ of the retionship whose job is just to… lie back and take it,” disgust seeped out through Jack’s voice as she spoke, “so we lesbians, or cool lesbians at least, have girls who top and girls who bottom. The bottom is the… receiver. She, ya know, takes it. It here being fingers, tongues, dildos…” She trailed off, her predatory grin turning contemptive. It occurred to Tracy that Jack had probably never had to expin the concept of gay sex before.

  Tracy’s blush grew hotter, even if Jack hadn’t outright said it yet, the implications were clear, her friend meant it very literally when she’d spoken of fucking her. She wanted to… penetrate Tracy. This stuff with the light dinner Jack had ordered her and now xatives, it was to prepare to get fucked in the ass. It was a jarring thought. Tracy had never once thought about… bottoming before, but now that the prospect was in front of her… she kept expecting fear or disgust at the prospect of being penetrated, but instead all she felt was excitement. She’d never had sex before, and was at least a bit relieved that she wouldn’t be giving Jack a disappointing performance with her-

  Her train of thought derailed. Her dick. She had a dick, because she wasn’t really a girl. This was all just py. At least, it was supposed to be. She was starting to realize that maybe Jack didn’t think it was. Her friend was just being so… earnest. It didn’t feel like Jack was pying out some kind of fantasy. To Jack she was… trans. That’s what her flirting and reassurances were hinting at. At some point this had gone from a night of odd rolepy to Jack actually thinking that Tracy was transgender.

  Tracy should tell the truth. She… He knows that. He should come clean about this, address whatever misconceptions Jack had, figure out how she convinced herself he was trans, and end the night. He should do all that.

  But does he have to? Jack is still referring to herself as a lesbian and she’s clearly not interested in being in a retionship with a man… but it’s not Tracy’s fault she thinks he’s a girl. Hell, she even asked him to pretend for her! If there’s any excuse to keep this little charade going then Tracy has it. But… does he want to keep up the charade? He could just say he’s getting uncomfortable and it would end. He could find out if Jack was actually interested in him as a man, not just while he’s crossdressing, and he wouldn’t be deceiving his best friend, not even a little bit.

  Except he wanted to keep deceiving Jack. This had been the most fun he’d ever had on a date. Sure, bottoming seemed a bit intimidating, but not any more than normal sex, and it was more appealing the more Tracy thought about it. Jack was the more sexually experienced of the two, by quite a bit, so why not let her take the lead and just let her have her way with him?

  Letting Jack have her way is what he’d been doing all night, and it had all been great! A bit more couldn’t hurt.

  That settled it for Tracy. Doubts and reevaluations were for when he was no longer full of alcohol and swept up in the moment. For tonight, Jack would get whatever she wanted, and what she wanted was for Tracy to be her newly trans girlfriend.

  ***

  A few hours ter Tracy possessed a new sympathy for trans women and gay men, (and cis women whose boyfriends convinced them to try anal, he supposed) the thorough cleaning her insides had received, when combined with her progressive sobering up, had left Tracy feeling exhausted. Fortunately for Jack, Tracy’s anticipation managed to outweigh her exhaustion. She had long ago accepted her virgin status and (mostly) gotten over her insecurities regarding it, but it was nice to finally be getting it gone, especially with someone as special to her as Jack. Even if things with Jack didn’t work out, Tracy would always be gd that Jack was her first time.

  A knock at the bathroom door brought a smile to Tracy’s face. “Almost ready babe. Surely you can wait a bit longer.”

  “I’ve been waiting for you for three years, Tracy. I don’t know how much more I have in me.”

  Jack’s response sent a shiver up Tracy’s spine, and she hurriedly finished tching the cy red bra. The lingerie set was far from fttering on her body. She had removed her breast forms, which left the cups baggy, and the panties were meant to hug hips she didn’t have. At least the garters made her legs look passable.

  Whatever, she thought, it was time to stop worrying and get it done. Jack wanted her body, and Jack would get it.

  Tracy stepped out of the bathroom expecting a smile; Jack was too good at making Tracy feel desired to wince, but that wasn’t what she received. Jack wore an expression of naked lust that made Tracy start to tent her underwear.

  Her lover was sitting on the edge of the bed, wearing bck boyshorts and a matching bra that fttered her rge bust. The milky white of Jack’s skin where it was usually hidden behind clothes was a stark contrast to her tanned face and arms, one that took Tracy’s breath away, just as it had ten years ago. But things wouldn’t end like they had the first time.

  Jack stood, her almost sck-jawed lust turning to a sleazy smile as she saw where Tracy was looking. A muscled arm and gesture of her hand shifted Tracy’s focus to her six-pack abs, and then further down to her thighs.

  “Like what you see?” Jack said breathily, already knowing the answer. “Because I do.”

  Shaken from her reverie, Tracy sputtered as strong hands gripped her waist and pulled her into a deep kiss. She almost choked as Jack’s tongue slipped past her lips and rubbed at the insides of her teeth, but forced herself to rex and lean further into the kiss. Jack rewarded her efforts by pressing the two of them even closer together, and slipping a hand down from Tracy’s waist. Tracy moaned into her lover’s mouth as Jack’s hand squeezed, digging into her soft ass, only to moan louder when Jack ended her groping with a smack.

  Tracy caught Jack’s smirk as she pulled out of the kiss, and scowled in return.

  “It just surprised me is-” Tracy was cut off by a gasp as Jack struck her ass again.

  “Just surprise?” Jack asked. “I think I can hear something else.”

  Before Jack could manage another sp Tracy dove into a kiss and leapt into Jack’s arms, forcing her lover to devote her hands to gently cradling Tracy’s butt, sparing it from further indignities, not that the gesture helped in removing Jack’s self satisfied grin. “My-oh-my… isn’t… someone… excited?” Jack managed between Tracy’s eager kisses as she gently id Tracy down upon the bed.

  “I’ve waited for this… for so long,” Tracy panted as she looked up at her best friend with wonder on her face.

  Jack’s smirk finally faltered at that, and she let slip her persona of the archetypal confident butch. “So have I,” she said quietly, “I need you Tracy.”

  Tracy moaned at Jack’s words, and Jack shuddered in return. Gentler, now having dropped her persona, Jack whispered, “Roll over baby. All you need to do is rex for me. I’ll take care of everything. I’m so gd- I- Thank you- Thank you for giving me your first time as a woman.” While Jack spoke, she gently held Tracy’s hips, and rolled her over onto her stomach.

  “Not just as a woman,” Tracy whispered breathily, which seemed to send a shock through her lover.

  “You’re still-” Jack started.

  “I just, never really had a chance. I didn’t want it to be casual but I just… never ended up getting into any serious retionships. None of the girls could hold a candle to you,” Tracy finished at a whisper.

  Tracy felt Jack still at her words, and she started to worry as the moment grew longer. Did she say the wrong thing? Jack seemed like she cared in some odd way about being Tracy’s first time as a girl, but was her actually being a virgin too much?

  She turned her head, just enough to catch Jack out the corner of her eye. Jack was breathing heavily as her eyes roamed Tracy’s body chaotically, as if desperately trying to dedicate each inch of it to memory.

  “Jack?” Tracy whispered, receiving no response.

  “Jack,” a bit louder, but Jack’s staring continued interrupted

  “Jack!”

  “All of this is mine,” at first Jack’s voice was full of wonder, but the darker, hungrier undertone filled her words as she continued. “Your body and all its firsts. I was your first kiss, your first trip to second base. I wasn’t your first time ten years ago, but it didn’t matter. You kept yourself my good, sweet, pure Tracy, you waited for me… I’m going to fuck you, I’m going to be the person who defines what sex even is for you, and then I’ll be the one closest to you as you blossom into the woman you were always meant to be.” Her hands groped at Tracy’s hips and ass, then between her thighs. “You’ll get softer and prettier, all for me, and I’ll be there for every inch the hormones change,” she breathed, as her hand brushed gently over Tracy’s cock.

  “Jack- God please- Jack you're teasing meee!” Tracy whined.

  “I am, baby. Is something wrong with that? I just want to savor you.”

  “I…” Tracy’s start was cut off by a moan as Jack’s fingers pressed into the sensitive spot behind her balls, “I neeed you.” She said, turning to face her lover with her best puppy dog eyes.

  “Tell me what you need,” Jack instructed.

  “I need you to… to…”

  “Use your words,” said Jack, cruelly, as she pressed her fingers into Tracy’s canals again, forcing another moan from the girl.

  “I need you to fuck me!” Tracy shuddered as Jack stopped pressing into her.

  “Don’t stop, tell me more.” Jack said in a sultry tone as she grabbed the lube and began affixing her strap-on.

  “I need you… to fuck me… like a girl,” Tracy managed to speak, still panting. Her mind was filled not just with the sensations Jack had given her, (though that peculiar fingering she’d received was still rge in her mind) but also with Jack’s words. It was clearly more than rolepy, more than the fantasy Tracy had initially read Jack’s desires as, and while it was obvious that Tracy had given Jack some wrong signals at some points, there was something appealing about what her lover wanted. It was a romantic thought, becoming a new person in the guiding hands of her best friend; a lifetime of firsts with Jack continuing into a second life. Maybe… maybe she didn’t need to dismiss Jack’s misconceptions so quickly. If being Jack’s woman meant feeling like this, then becoming a girl was a small price to pay.

  A hand pulled down her panties, and a cooler, wetter hand pressed against her ass, drawing a yelp from Tracy and a chuckle from Jack, who quickly got to work spreading the lube. The cold of the lube was unpleasant, but the wet slickness of her body under Jack’s hand was far more sensual than Tracy had anticipated, and she caught herself moaning more than once. She just luxuriated in the feeling until Jack instructed her to lift her hips and present her ass, which left her in the mildly humiliating (and deeply arousing) position of ying face-down ass-up as her girlfriend prepared to spread more lube inside her.

  Jack spoke, tenderly this time, “You don’t need to worry baby, it won’t hurt, I’ve done this before.”

  Her lover’s reassurances comforted Tracy, and she found herself rexed as Jack’s first finger penetrated her. She didn’t moan at first, surprising herself, she’d expected being penetrated to feel good, but it just felt weird. The weirdness quadrupled when Jack pulled her finger out and put it back in to spread even more lube inside her girlfriend. Finally, Tracy was starting to have doubts about the situation she’d gotten herself into. While she was gd her first time would be with Jack, she was starting to fear her first “defining” sexual experience would just be awkward and unpleasant.

  Seeming to notice her discomfort, Jack leaned in and craned her neck to look Tracy in her eyes. “Is something the matter babe?” Jack asked, her tone full of concern.

  Tracy quickly tried to pster on a fake smile, though she doubted it worked, Jack knew her too well, “Not at all. Are you almost done back there?”

  Jack chuckled, “Not yet. I’ll let you know when I’m getting close.”

  Tracy’s face fell just as soon as Jack pulled herself back to focus on her work. She wasn’t sure how long she could continue enduring whatever the hell this was supposed to be. She didn’t want to ruin her and Jack’s night though, especially since that would potentially torpedo her chance at having a retionship with Jack at all.

  Jack asked if Tracy was ready for another finger, and she agreed to it with false cheer. The second finger wasn’t as bad, maybe only 25% worse than the first one, but then Jack started moving much more vigorously and the effect became much worse. Jack’s fingers weren’t moving in the spreading motion of before though, this was more localized, focused on the side of her inner walls nearest her cock.

  Whatever, Tracy thought, Jack’s had plenty of fun pying with her ass, she deserved a break.

  Tracy breathed in, “Jack-”

  “Just a second babe.”

  “What are you-”

  Jack’s fingers brushed against something inside her and Tracy gasped as warmth flooded her body. It was pleasure, she could identify that right away, but it was different from what she was used to. It was a bit like touching herself, only not at all. It was simultaneously softer and gentler, and infinitely more intense and consuming, particurly as the feeling seemed to suffuse her entire lower body.

  A moan escaped her lips, far lewder than anything she’d let out so far, and when she turned to face Jack her lover was smirking down at her. “Found it.”

  Before Tracy could ask what she meant, Jack ran her fingers over the spot again, conjuring yet more all consuming warmth inside her. Tracy could feel herself soaking the sheets, her cock was leaking like a faucet, far more than she’d ever produced before.

  Jack brushed her spot again, pressing just a tiny bit this time, and Tracy gave up maintaining coherent thoughts.

  It felt like an hour had passed (though it couldn’t have been more than a minute) when Jack rolled her over onto her back.

  “How are you feeling babygirl?” Jack asked, her smug smirk repced with a genuinely caring smile.

  “I’m- Jesus Christ- what the fuck was that?” Tracy replied, too disoriented to watch her nguage.

  “That good huh?” Jack raised her eyebrows, “That was me touching your prostate baby. It makes cum I think? The fluid, not the sperm, I’m not entirely sure though. What I do know is that it’s like the g-spot but for trans girls.”

  “Like, just for trans girls? Can you test for trans-ness this way?” Tracy managed with a giggle.

  Jack lightly swatted her on the thigh, “I think guys have them too, probably, but there's no way to be sure.”

  The lovers both chuckled for a bit, until Tracy’s eyes were drawn down to the small (but still intimidating) silicone cock finally fixed between Jack’s legs. She bit her lip, asking, “That will feel like your fingers?”

  “Better, or so I’m told.”

  Tracy shuddered with desire, and spread her legs, as she bunched up the bnkets a bit under her tailbone to prop her ass up. She felt exposed, even vulnerable, but it was a comforting kind of vulnerability. She’d always trusted Jack with all her heart, it was easy now to trust Jack with her body.

  Tracy’s lover gracefully transitioned from her standing position to kneeling on the bed before Tracy. She (finally) finished with the lube, applying to her strap-on with strokes far more sensuous than Tracy suspected was necessary. Not that Tracy would compin, Jack’s comfort in the situation was rubbing off on her, it was nice to know she was in good hands.

  Strong hands gripped Tracy’s hips as Jack prepared to enter her.

  “Are you ready babydoll?”

  “Yes Jack! Please.”

  “I love the way you say my name,” Jack said, gently running her fingers across Tracy’s dick before returning her hand to Tracy’s hip, “I love you.”

  The words weren’t new, but they felt like Tracy had never heard them before as her body spread around Jack’s silicone cock. She was ready this time for the uncomfortable sensation of a foreign object entering her ass, but that discomfort was quickly repced by the pleasurable warmth she desired.

  “How does it feel?” Jack asked, looking down at Tracy and shaking as if she was the one being fucked.

  The stimution of Tracy’s prostate combined with the gentle pressure on her inner walls to make the feeling of being stretched around Jack’s strap-on near orgasmic. She answered Jack’s question with moans, and a desperate reaching for her cock. Before she could touch herself though, on of Jack’s hands shot from Tracy’s hip to grab her by the wrist.

  “Not yet baby. Don’t worry about that, don’t worry about anything. I’ll take care of your little clitty when I’m ready to.” As she spoke, Jack rocked her hips back and forth, sending another wave of pleasure through her lover.

  “Was that okay babygirl?” Jack asked, rocking her hips again, “I’m going to start properly thrusting soon dear. Just stay rexed and enjoy it.”

  Tracy’s moaning accelerated, both at her denial of release and Jack’s gentle fucking. She felt incredible, the pleasure never seemed to fade, it just built on itself over and over. Even just the gentle rocking of Jack’s hips was a bit overwhelming to the virginal Tracy, though when the strap began gently sliding out of her she whined anyway.

  “Jack! No, keep g-”

  When the strap bottomed out inside her Tracy saw stars. Jack was like an angel above her, and every thrust of the strap-on was divine. The feeling of fullness she’d hated before now made her feel all the closer to Jack, she wasn’t just touching her lover, she was so full of Jack it almost hurt.

  “Good girl, just like that, you’re taking it so well,” Jack reached out a hand to cup Tracy’s cheek and force her girlfriend to meet your eyes, “Tell me what you’re feeling baby, use your words. I want to hear it.”

  “Fuck… Jack… I love you, I’ve always loved you. This is so much better than I ever imagined sex could be, and it’s all because of you…” Tracy hesitated, she didn’t know if she could take back what she wanted to say, but maybe… maybe if she wanted to say it, she wouldn’t need to take it back. “I’m yours Jack, I’m your girl, I need you. I… never want this to end.”

  Her word’s galvanized Jack to pick up the pace. The strap-on was smming in and out Tracy now, and she finally appreciated the slow start they’d gotten off to. The waves of pleasure almost hurt now in their intensity, and her cock was leaking like a faucet, absolutely covering Tracy in her own pre-cum.

  It was all too much to handle, but then Jack’s hand, softer than Tracy expected given her muscled physique, brushed against Tracy’s cock. Her whole body stiffened, then shook as if she’d been struck by lightning. She was so… so… so close, just a little more…

  When Jack’s hand enveloped Tracy’s cock and gave it a single, gentle stroke, she exploded. It was the most intense climax of her life, even comparing it to the pathetic orgasms she gave herself felt wrong. Her moan turned into a scream without her even realizing, she was too focused on the pure sensation coursing through her, all the while Jack looked down at her with a mix of love and satisfaction.

  It was finally all too much for Tracy. She felt herself lying in bed, but was at the same time floating above herself. Jack was whispering sweet nothings, but Tracy was alone with her thoughts, and there she finally considered what she looked like. She didn’t look like Jack’s boyfriend, she looked like a crossdresser, or, more generously, she looked like an early transition woman.

  Tracy considered that for a while, as Jack cleaned the two of them up. It was what she looked like, it was what Jack wanted, and while Jack made a mess of Tracy’s body and words of love poured from her lips, it was what she had decred herself to be.

  Floating above herself, Tracy compiled her st thought before passing out from exhaustion. Why fight it any more when she’d never really wanted to in the first pce?