She Smiled at Her Pt. 01

This story is the first installment of a prequel series based on my ongoing work "Is She Smiling at Me?" It works fine as a stand-alone, I think, though you might have a deeper appreciation for the characters if you have read some of ISSaM first. This story is a work of fiction. Any resemblance to real people is purely coincidental. I love hearing feedback from my readers; please feel free to leave comments or contact me with your thoughts or suggestions.

Please note: This story is a collaborative effort between myself and fellow author Silkee Smooth. It would not have been possible without her writing talent and her thoughtful insight. Don't forget to check out her work.

*****

Liz looked at the door handle and closed her eyes, this was the ritual.

'Breathe in... Center... Breathe out.' She thought to herself. Her excitement built, accompanied by an underlying sense of anxiety; the thrill of danger. She had chosen this, and living the rest of her life in her parents' house safe and sound was not an option.

'Breathe in...' She relaxed, feeling the inner tension dissipate some, 'I want this.'

Elizabeth Crawford, 'Liz,' had known for several years now that she liked boys. This wasn't so much a problem in the modern world; while it would have been a straightforward enough matter to simply find a guy that she was attracted to, that just so happened to also like boys, her life could have been much simpler than it actually was.

Liz liked boys, but she didn't feel like a boy herself. She had always gravitated towards all things feminine. She marveled at the grace with which many women displayed with seemingly no effort at all. Their cat-like movements, their ability to defy gravity and sway seductively in impossibly high heels, their basic mannerisms; all combined to intoxicate her. Liz may have been born as a male, but everything she identified with would have suggested otherwise. She had decided in her last year of school that after graduation, 'Elizabeth' would emerge once and for all; she would begin her life as an adult, and as the young woman that she had always known she was. There would be no returning to the boy she had been pretending to be.

'Breathe in... Center... Breathe out...'

Her breasts had become her compass. When she could no longer wrap them, or otherwise disguise what the hormones had begun changing about her anatomy, then it would finally be time to fully embrace the woman inside her that yearned to be free. She had a noticeable A-cup at the moment, but Liz had determined she would only be satisfied once they had grown into a more desirable D-cup. She had imagined all of the outfits that she couldn't wait to wear, all showcasing her bountiful bosom. She could imagine the presence of such breasts, the mass, the heft... She couldn't wait!

"It's possible that you may see growth up to several years after you begin." Her doctor had told her, "Although most of the breast growth will likely happen in the first year to eighteen months."

Liz had remembered his words, then scrunched up her face. "You may see growth anywhere from an A-cup up to possibly, although unlikely, a C-cup."

"I'd like them to be larger, is there anything I can do to increase my odds?" Liz recalled asking the doctor.

He smiled warmly at the young woman-to-be and nodded, "Breast augmentation surgery. Science has advanced considerably, and it's very possible now to achieve the size desired, while maintaining a very natural look, with minimal scarring. Although, at your size Elizabeth, I'd suggest giving that some additional thought. With your smaller, slender frame, breasts that large might appear... Well... Give it some thought."

For now, Liz just kept her hopes up that the hormones she had begun taking would give her the size she desired. Surgery wasn't something she was keen to consider. Her parents had both been incredibly supportive, although her mother had known for years that Liz had an ongoing interest in presenting as a female. She would often find one of her lipsticks missing from her vanity, only to have it magically reappear the following day, or the many times Liz had been practicing her makeup and failed to clean it off completely; a bit of eyeliner may have given her away, small things like that. Liz's mother knew the day would come and it would be out in the open, but she worried that her husband would take it badly. To everyone's surprise, he'd given Liz a big hug, and admitted he'd had his suspicions for quite a while. Liz would never forget her father looking her in the eye and telling her, "No matter who, or what, you want to be, I will always love and support you."

'Breath in... Center... Breathe out...'

Liz twisted the door handle and stepped outside. The sun warmed her face, and she smiled brightly. Today would be a wonderful day. Shopping at the mall as 'Liz' was still a new enough experience for her, and while she easily presented as a young, beautiful woman, she had not yet developed the effortless confidence she so often saw in other women. This was that bit of danger she had thought of back home. It lurked just below the surface; she feared that she might betray herself. Liz knew that she could out herself far more easily than any casual observer could.

And so the shopping experience was partly shopping and partly practice. Liz had to be acutely aware of her movements, her voice, and her mannerisms. In a way, it was like a drug, but almost in reverse. She could simply relax, or she could monitor all of these things that contributed to the whole of her femininity, which would result in something close to a high. Those thoughts would typically cause a stirring in her penis, but with it tucked back behind her legs and held in place with the boyshorts panties she wore today, she felt confident that her anatomy wouldn't betray her.

"Those are cute." Liz heard a voice behind her, soft and sweet, yet at the same time bold and assertive.

Liz turned to see the woman who owned the voice. She was strikingly beautiful, with a pale, alabaster complexion dotted with a spray of freckles. Her brilliant red hair contrasted with the black, form-fitting dress she wore, showing off her slender figure and small chest. Piercing, emerald green eyes met Liz's, broadcasting a sense of unwavering self-confidence. The woman was taller than Liz by more than a little, though to be fair, the 4-inch red suede peep-toe heels she wore aided in that. Sexy. She was sexy. There was really no other word for the presence that the woman projected as she smiled at her.

"The shoes... They're cute." The woman said once again.

Liz snapped back to the moment, realizing that she was holding a pair of flesh-colored platform pumps with a 5-inch heel, looking from the redheaded woman to the shoes in her hand, and then back up at her.

"They're beautiful, but... Wow, I'm not sure about walking in something like these." She giggled.

"It's easier than you think, that heel just looks scary. I'm Alex." She smiled warmly, extending a slender hand adorned with shiny red nails that extended just past her fingertips.

"I'm Elizabeth. Liz." The younger woman answered as she shook hands.

"Do you really think they'd be easy to walk in?" She asked.

Alex grinned, then pointed to her own feet, "These have four-inch heels, and I've been in them all morning. Now with those, there's easily a one-inch platform hidden in the sole of the shoe, so those will actually be easier to manage than these."

"Wait... Have you worn heels before?" She gave Liz a look with an arched eyebrow.

Liz shook her head, "Not yet, I really love these though." Her brown eyes sparkled; eyes that were both beautiful and curiously large.

"Well, Liz, heels take a bit of getting used to. Maybe I can help point you towards something a bit less sexy, something easier for you to learn to walk in." She teased the younger girl. This was part of the process; she wanted to learn more about her without asking, and she knew she could prod a reaction out of her.

"I like these." Liz replied with a bit of an attitude, "I'm sure I'll manage."

Alex crossed her arms in front of her chest and raised a finger to her lips as if she were contemplating an idea.

"I can picture you in those, maybe wearing a charcoal minidress, out on the dance floor." Alex said, letting the words hang in the air before adding, "For a few seconds anyway, before twisting your ankle, and someone calling an ambulance."

She grinned playfully, letting the younger woman know she was joking.

"A charcoal minidress would work with these?" Liz asked, ignoring the jab as her eyes flashed down to the heels in her hands once again.

"Mm-hmm, in fact, I saw one just a bit ago. The last shop I was at had one." Alex answered, "I could show you. If you'd like."

Liz paid for the shoes and chatted with Alex about the various types of outfits she could put together to go with her new shoes. It seemed to Liz that Alex must have been a fashion expert, she appeared to have endless knowledge of such matters. While they waited in line, Liz noticed Alex glancing down to the front of her skirt. Liz tensed a bit when she noticed Alex do it again. Something about the way the older woman was looking at her made her uneasy.

"It's okay, Liz," Alex said softly.

Liz said nothing, but her eyes widened; surely this woman didn't know. How could she?

They walked together through the mall, Alex explaining the art of walking in heels to Liz while making a show of demonstrating in her own shoes. She made it seem effortless, and the confidence Alex exuded began to have an impact on Liz.

"It's simple. Heel, toe, repeat... Just put your front foot directly in line with your back foot; heel, toe, repeat." Alex instructed, taking on a bit of a mentoring tone.

"You have to commit to it, Liz. Don't ever look down in heels, know that you own them, make them your bitch." She giggled.

By that point, Liz's penis had begun responding. Alex had a way about her; she was cocky, but in a warm, friendly way. She would never have imagined meeting someone like her in the mall, yet here she was, listening to this sexy woman give her a little lesson in femininity.

They found the dress Alex had described, and Liz asked if she would wait while she tried it on, which the older woman happily agreed to.

The door closed to the changing room, and less than ten seconds had passed before she heard Alex's voice, "Are you okay in there Liz? Do you need any help?"

"Oh my god! I'm fine, give me a minute!" Liz laughed back at her through the door.

A short while later, Liz stepped out of the changing room and modeled the dress for Alex, doing a slow pirouette and smiling as she caught a glimpse of herself in one of the full-length mirrors that surrounded the changing room area. She looked hot!

"So? I like it, what do you think?" Liz asked.

"Put the heels on, then let's see," Alex instructed. Her tone felt as if she wasn't asking Liz, more telling her.

"I really don't want to break an ankle, and need you to call that ambulance you talked about before." Liz grimaced, uncertainty creeping into her mind.

"No time like the present Liz, now put those big girl shoes on, and let's give you the once-over," Alex stated firmly.

Liz nodded, slipping the heels onto her petite feet and standing shakily. She felt unsteady as she fought for equilibrium, finally settling into something reminiscent of control. The heels made her taller than she had expected, and she was surprised at the change of perspective. Liz looked down at her shoes, then back at Alex, grinning broadly.

"Own it, girl," Alex said with a nod.

Liz stepped uneasily to the mirror and admired her reflection. Sure, it was still just her, but the dress showed off her shapely legs, and the heels were causing her calf muscles to work overtime. The shoes threw her balance off in a strange new way that made her taut ass stick out a bit further than normal. The outfit, combined with the way that the heels had made slight changes in her posture gave Liz a tingling sensation deep inside herself. She felt an excitement the likes of which she had previously only scratched the surface of. Alex was right; the heels matched so well with the dress! She looked past her reflection and saw Alex smiling, though as she followed the older woman's line of sight, Liz realized that she was staring at her ass. Again, she felt that sense of unease, but she shook it off as her eyes flashed back to her reflection.

"I love it Alex, thank you so much! I wouldn't have been able to figure out such a hot outfit." Liz exclaimed with a brilliant smile.

"It's my pleasure, Liz. That dress looks fantastic on you." Alex nodded her approval, "Are you done shopping? Or...?"

"It depends. Do you think you can help me pick a few other things?" Liz asked hopefully.

"I will if you let me buy you a coffee after we finish," Alex answered, once again checking Liz out, and not seeming to care if she knew it.

The two visited several more shops and Alex made multiple suggestions, a blouse, a skirt, she pointed out various pantyhose, and stockings, then asked if Liz had a preference for hosiery. Liz had been caught off-guard with the question. That didn't make sense; two women just chatting about pantyhose shouldn't be a big deal, but that lingering part of Liz's brain that computed such things as sexual, as sensual, betrayed her.

"I um... Don't really care... Either way, I guess." Liz shrugged, although her penis twitching against the confines of her panties would have suggested otherwise.

"Well, I suppose it does depend on the situation. Let's say you are out on the town, wearing your new heels and dress... Let's say that you were on the prowl, looking for... Um... Well, it doesn't matter, a guy, or a girl, whichever you prefer..." Alex trailed off with a grin.

"I like guys." Liz nodded, now being pulled into Alex's scenario.

"And so you end up dancing, you're really close with a really hot guy, he's got chiseled good looks, smells great, and can dance... You decide you're bringing him back to your place." Alex's voice had changed, it was as if she were narrating a scene taking place in front of her.

"So, there you are, okay? Pantyhose, or stockings?' She asked.

"Um, I guess, oh, I don't know, either is fine!" Liz exclaimed with a giggle. The scenario Alex was describing filled her with nervous excitement.

"Wrong answer, Liz!" Alex grinned, shaking her head.

"You don't want to have some guy you just met destroy your pantyhose, and besides, if he could really dance, they'd be a mess by now anyway, right?" She smiled playfully, letting her eyes stray down to the front of Liz's skirt, then slowly looking back up to meet her gaze.

Liz looked down to where Alex's eyes had drifted, suddenly worried sick that somehow a bulge had formed there, but she could find no sign of anything that would have given her away. Why was Alex now so obviously checking her out? 'She must be a lesbian,' Liz reasoned. Alex was doing this to signal her interest; that had to be the answer.

She hadn't considered this kind of situation. If Alex was trying to hook up with her, she had the small problem of needing to have that uncomfortable chat; 'Um, Alex, I wasn't actually born a female...' While she could imagine how a guy might take that news, she had no idea how a woman would respond. It might be worse. It might be much worse. Besides, Liz liked boys.

"I know," Alex said quietly as they drank their coffee.

Liz snapped back to reality and looked at Alex curiously.

"You know... What?" She asked, a lump forming in her throat.

"Liz... I know." Alex said with an assuring tone, standing and reaching into her purse. She dug out a small card and handed it to Liz with a warm smile. The card read 'Alexandra Kelly' with her number printed below.

"I really enjoyed meeting you today, Liz. I had fun shopping and talking. I hope you'll call me, and we can do this again." She extended her arms welcomingly.

Liz stood and hugged the older woman. She smelled incredible, her perfume intimate, needing proximity to be detected, and her small breasts were soft as they pressed into Liz's. Alex gave Liz a quick peck on the cheek, and as she turned to leave, she added; "Oh, and next time we go shopping, wear that dress you bought today... And the heels."

Liz watched as Alex walked out of the coffee shop. She had never met anyone quite like her; there was a part of her that wanted to be Alex, her unapologetic confidence was intoxicating. She resolved right away that she would definitely call her to go shopping again, though the instruction to wear that outfit and heels gave her pause. And what about that cryptic message Alex had delivered before handing over her card? Was the redhead beauty telling her that she knew she was trans? The notion seemed impossible, and she dismissed the thought with a shake of her head. Liz figured she would need to explain to Alex about her gender situation; one way or another, it was obvious Alex had a sexual attraction to Liz, and she owed it to her to explain that she wasn't entirely what she appeared to be.

But first, she needed to get home and start practicing walking in her new heels.

*****

"Hey, daddy!" Liz called to her father sitting on a recliner as she came through the door carrying her shopping bags.

"Hey, sweetheart," Her dad smiled up at her over the book he'd been reading, "How was shopping?"

"Amazing!" Liz grinned brightly, unable to contain her excitement as she kicked off her shoes.

"Really?" Her father chuckled at his daughter's brimming enthusiasm.

"Hmm-mhm," She affirmed as she crossed the room, bending to kiss her dad on the cheek.

"I think I made a new friend. Another customer in one of the stores asked if she could give me some fashion tips and we ended up shopping together all day!"

"Well, that's great honey!" He smiled up at her, enjoying his daughter's happiness.

"Okay, I'm going to go try on clothes!"

"Okay." He chuckled again, but Liz was already down the hall to her bedroom.

Liz was giddy. She had just had the best day and she couldn't remember the last time she felt so... What did she feel? She was thrilled, ecstatic really, bursting with joy, pride, and energy. A medley of wonderful, bright, happy emotions flooded through her, lifting her spirits so high she thought she might levitate right off the floor. She threw her bags down on her bed and sat, cross-legged on the mattress, giggling as she rifled through her purchases.

Finding her new dress and shoes, she quickly stripped down to her bra and panties, pausing as she caught a glimpse of herself in the full-length mirror in the corner of her room. Liz looked herself up and down, thankful for being blessed with such a slight, petite frame. She felt proud of the subtle, feminine lines of her body, her slender legs, the curvature of her hips and her taut little ass, her flat stomach... When her eyes drifted up to her small breasts she caught herself frowning slightly, but she pushed the negativity out of her head. 'One step in a long journey,' Liz thought. Nothing would bring her down today.

Her excitement returned in full force as she pulled on the dress, sitting on the edge of her bed to slip her new heels on. She rose carefully on shaky legs, finding her balance and taking a step forward. And then another. 'Heel, toe...' Liz told herself, repeating the words like a mantra as she walked back and forth in front of the mirror. As she moved around her room, she could feel herself growing more and more steady, and her confidence swelled. She watched her gait transform before eyes from an awkward, halting step into a sexy stride. Her penis expressed its enthusiasm, straining against her panties as it twitched and swelled.