Coaxing Her Out of Her Shell

It all started during the big snowstorm. Even though she lives right next door, apparently Lily and Ryan's houses are in two different sections of the power grid. Over a foot of snow had fallen overnight, alongside high winds, and thanks to the blizzard Ryan's office was closed the next day. He'd taken the morning slowly, making a cup of coffee while playing jazzy music on the living room sound system, then watching the snow continue to fall while he sipped.

By the afternoon he was bored. Sure, he could play any number of video games he owned, and the internet still worked to find something to watch or something to do. But none of that was appealing - Ryan wanted something new, a project maybe. Something interactive, creative, and fun.

His doorbell rang, and he raised an eyebrow. The whole city is shut down. Who on earth would be visiting my house? He opened the door and found on the other side a mousy brunette girl with glasses and a messy wolf cut, huddled in a winter coat - his neighbor, Lily. Ryan had met her briefly when he'd moved in, and waved hi a few times since, but didn't really know her. Lily was a bit of a shut-in, as far as he could tell; she seemed to work from home, and there was no evidence of a social life. Nobody visited her, and she didn't go anywhere.

"Hi Lily," Ryan said. "What can I do for you?"

She looked incredibly sheepish, and it took a few seconds for her to say anything. "I...need your help." Her voice was smokier than Ryan expected - they'd exchanged very few words prior to this - and she sounded downright embarrassed to be asking. "My power is out, and the house is getting really cold. Could I...crash on your couch tonight? The power company said it should be back on tomorrow."

Ryan ushered her inside. "Sure, of course. Not a problem at all." He closed the door behind her, showed her to the living room, and made his way to the kitchen. "Coffee, tea, hot chocolate?" he called out to Lily.

"Tea would be great, thank you!" she said, barely audible from the next room.

Once the tea was ready, Ryan brought it to Lily. She had removed her big coat and boots, leaving her huddled on the couch in a big, oversized hoodie and a loose-fitting pair of jeans - pretty much the only outfit he'd ever seen her in. "Lucky my house isn't without power too, huh?" he said as he handed over the tea.

"Thank you," she said meekly, "and yeah, I guess so. I saw your lights were on and I...well, eventually I decided I could come ask."

"I hope you weren't hesitant because I've been unfriendly!"

"No! No..." Lily looked a little panicked, as if worried she'd said something wrong. "You've always been nice. I just..." She trailed off. She stared into her tea, blushing.

"Well, um...I'm glad you came over. I'm happy to help, really."

Ryan kept himself busy the rest of the afternoon. He and Lily talked some more, but each time she quickly clammed up, seeming to be flustered and overwhelmed by socializing. So, Ryan tried not to overdo it, mostly leaving her alone in the living room watching TV while he puttered about doing overdue chores.

By night time, Ryan was bored of this, so he made a suggestion that he hoped would help ease socializing for her. "Hey," he said as he entered the living room, "I was going to make myself some hot chocolate and sit and watch the snow fall. Would you like some?" Lily just nodded enthusiastically. Ryan held up the bottle in his hand. "And I'm adding Fireball to mine for a little extra warmth and spice. What do you say?" This nod was a little more reserved, but she nodded.

Holding hot mugs of spiked hot chocolate, they sat quietly in the living room with the lights off, watching as fat snowflakes fell lazily to the earth outside. Thankfully, it was no longer last night's blizzard conditions, just a slow accumulation. They sipped their drinks and watched in silence; Ryan didn't want to put too much pressure on her.

About half an hour, they'd both finished their drinks. "More?" Ryan asked, taking her empty mug, and Lily just nodded.

Settled in with new drinks, Lily finally spoke up of her own accord. "Thank you for letting me stay here tonight, Ryan."

"It's not a problem at all. Hell, even if it was, I'd still do it - only a cruel person would let you freeze in your unheated house."

She chuckled, the first time he'd seen her laugh. She seemed ashamed to do so and quickly turned her face away - but she had a nice smile. "I suppose that's true. Still feels like imposing though."

"Well, you aren't. In fact, please feel free to come over whenever you need something. That's what neighbors should be to each other. For that matter, we could just...you know, be friends."

She blushed again,nodded, and hid her face behind her mug.

By the time she drained the second mug of Fireball hot chocolate, Lily's face was flushed and she finally seemed to be relaxing a bit. They started talking about video games - they had a few favorites in common - and then tech in general. It turned out Lily was a programmer, working for a company halfway around the world, and thus had no issues working from home. Ryan told her in turn about his own job - not tech exactly, but procurement and management for his company's IT department. "I'm the guy who translates between IT and people who have no idea what IT guys are talking about."

That got a full laugh out of Lily, and she didn't hide her face this time.

By bedtime, conversation was finally flowing. Ryan learned that Lily was 25, about five years younger than him, and had inherited the house she lived in from an uncle who passed away shortly after she finished college. She lived alone, as he suspected, and didn't really have any friends, as he suspected. She wanted to, though - Ryan felt like they reached a tipping point when she quietly confessed that she was lonely, and wanted to get out in the world and experience life as a young woman, but that she was debilitatingly scared to do so.

"Would you like some help?" Ryan asked bluntly.

"What?"

"Would you like me to help you? I could invite you out, check in, offer advice. I could be your first friend and help you with your project to find more."

A grin reflexively spread across Lily's face, and she looked away. "Y-yeah. That would be nice," she whispered.

"Okay then," Ryan said decisively. "That's what we'll do. Once the city is functioning again, I'll invite you out, and we'll start getting you acclimated to the wild world of...well, social events," he finished anticlimactically. That drew another laugh.

Ryan realized what time it was and stood. "Unfortunately, it's getting late. I laid out a towel for you in the bathroom in case you want to shower, and there are blankets and pillows there on the coffee table. Anything else you need tonight?"

Lily emphatically shook her head. "No, thank you, you've been more than helpful enough. I'll um...yeah, I guess I'll shower in a few minutes." After her drinks, she looked flushed, clearly a bit drunk. She stood quickly, and in her state she stumbled a bit.

Ryan wasn't far from her, so he took a step and reached out an arm, holding her by the shoulders while she steadied herself. "T-thank you," she whispered, mousy Lily reemerging. "Sorry."

"You're fine, Lily. No worries. You good?" She was a little stiff under his arm, but did not move away.

"Y-yeah...thank you." Without looking at him, she fled the room.

Ryan spent a few minutes cleaning up in the kitchen, then made his way to his bedroom. To do so, he passed by the bathroom. Surprisingly, despite hearing water running, the door was ajar.

Ryan didn't want to peep, but it was hard to completely suppress the urge. As he passed, he glanced over. Lily had stripped out of her hoodie and jeans and stood in a pair of black boyshort panties and a white sports bra - an unsurprisingly humdrum set of underwear given her fashion sense. She was leaning on the bathroom counter, staring at herself in the mirror, as though contemplating something. Ryan's eyes were drawn to her ass - it was small, but round and perky. Yum.

Ryan started to speed past, but as he did Lily turned. As his eyes were already at hip-height, her rotation caused them to land directly on her crotch; there, a total surprise, was the unmistakable bulge of a small cock. Wait, Lily's trans? Then, reflexively, Ryan tore his eyes away and met Lily's startled gaze. "Sorry!" they both barked simultaneously. Ryan fled, and Lily slammed the door shut.

The next morning was awkward. Neither really looked the other in the face, and both maintained a very polite, stiff demeanor as they shared coffee and breakfast. By the time Ryan got home from work, he had a text from Lily - her house had power again, and she'd gone home.

Nonetheless, Ryan made good on his promise to help. A few weeks later, went bowling - a perfectly mundane, pleasant friend date. A couple weeks after that, Ryan had some friends over, and invited Lily. She still wore her big hoodie, and she was quiet, but she talked some and looked heartened to be included.

As their friendship blossomed, and Lily started to be a little less reserved, Ryan couldn't stop thinking about what he'd seen in the bathroom that first night. Her cute little butt, her flat tummy, the slight swell of her small breasts beneath her bra...and the bulge between her legs.

Ryan had no problem with trans people. He knew a couple other trans people, and was confused and saddened by they way some people seemed to hate them. But he'd never seen a trans woman in such an intimate way before. Not to mention, he'd never had that kind of awkward voyeuristic moment with any woman in his life.

Ryan wondered if Lily thought about it too. She'd seemed apologetic that night, which he supposed was fair, given that she'd left the door open. She also didn't seem to hold the incident against him, only being awkward about it the next morning - well, more awkward than usual, anyway. He had no idea what she was into, who she was into, but she was quite cute. Maybe...? But first and foremost, Ryan was her friend.