A Crossdresser and an Exhibitionist Ch. 02

Lillian's mother was the only other person living with her and she had been out all night on her nurse shift. She didn't return home until well after seven the next morning. Quietly, without disturbing Lillian, and most importantly, none the wiser of her daughter's secret hobby.

Lillian woke the next morning around ten after enjoying a nice session of sleeping in. She shrugged the covers off of her naked body and wandered from her room to the bathroom. There were two within the three-bedroom apartment. One was in the hallway with the bedrooms, the other was a much smaller one without a bathtub in the combination living room/kitchen. Lillian and her mother had their own rooms while the third bedroom was an office for her mother. Her mother being out meant she could enjoy one last bit of nudity to herself as she showered and then was forced to dress for the day. She pulled on a comfortable T-shirt over her soft blue cotton bra and matching panties with a small white ribbon on the front. Over those she slipped on a pair of jean shorts that reached her knees, covering her rounded thighs comfortably and easily.

She wandered into the kitchen where she found a note from her mother about being out of ingredients for breakfast and a few bills on the table, asking her to pick up something for her to eat later. There were quite a few places near the apartment complex so she figured she could get by with walking to most.

Heading out of her apartment she reminisced about the night before, memories making her blush as she stepped onto the elevator. "I wonder... did he go looking for me? He and whoever else knows... Or was it a little secret, just like his dress?" She smiled to herself as the elevator lurched down the building.

She came back about thirty minutes later with some breakfast from a local diner and some groceries for her mother, her ears plugged with a pair of earbuds as she listened to some upbeat music to start her day, unaware that as she rounded to enter the building things would once again get interesting.

Turning the corner, Lillian was caught up in the climax of her song, her eyes closed and body ready for the drop in the music to single out the heavy lyrics before the beat would drop back into place. Nothing on the outside world was registering as she swung to reach the door and found sudden contact with a smaller, warmer frame. the impact made her stumble back with shock while her collision target merely took a step back on stable footing. "Ah hey! Sorry about that" she said, almost at the same time as he cried "Oh, sorry, I-"

As his eyes scanned her, hers did the same, staring with the same shocked and confused face that she had seen on him the entire time she had been in the elevator. Her gaze moved down down to the less than investing attire he wore this time before managing to catch his eyes once more. He was drinking in her entire body, this time actually clothed! She could tell by his expression he had already undressed her with his eyes and was imagining the sight he was more than familiar with instead. She meanwhile couldn't quite imagine him in a dress, not with the one-size-too-big orange tank top, khaki board shorts, and black sandals he was currently wearing.

For a moment, she felt doubt. Would he really recognize her or was he in the habit of studying every girl he came across? Would he even say anything or would he shyly move on and pretend nothing ever happened? She was keen on finding out. If he didn't bring it up then that was that.. she wasn't exactly able to fully bring it up herself, after all. What did one say in a situation like this? Yes it's me, the girl you ran into naked! By the way where is your dress!? Sure... She could have if she was naked again, but right now she was just another girl dressed in clothing that some might say wasn't flattering to her, with a face in the crowd one looked over too quickly.

So you can imagine Lillian's mixture of surprise and relief when the first words out of the androgynous young man's mouth after he finished his inspection were a stammering and breathless "I-It's you..." as he made eye contact with her. Huh, it looked like she made the lasting impression she wanted on him. With his admission of recognizing her, she hurriedly grabbed his hand and pulled him outside the doorway arch and around the corner of the building without a word.

Blocking his escape in a small service alley, she stood with her hands on her hips, looking his scrawny body over. He was maybe an inch or two shorter than her. "I'm glad you actually recognize me, though I should say I'm a bit worried cause it means my hat wasn't really that great at hiding who I was," she grumbled before she looked him over. "You didn't tell anyone right? About what you saw?" Her question came out more nervous than she intended, that confidence from the night before absent. "No, of course not, then you'd have to admit what you were doing, too. Right, stupid me. Sorry. I have to admit... I always knew I'd get caught one day... but not by someone like you." Unaware how that might sound, she added a soft "I mean, what are the odds right? Finding someone who might actually understand me in a way..." she saw his confusion for a moment and sighed. "Don't worry I won't tell anyone if you won't, but... I mean you have to admit, what are the chances, right? Both of us living out our little fantasies." She was about to blush and dive into a personal fantasy when she managed to remember something and stuck her hand out. "I'm Lillian, by the way. Sorry, when I get nervous I talk a lot..." she admitted, her voice taking an a sudden shy undertone.

Her entire behavior was different at the moment, one arm meekly across her waist as if trying to hide her curved stomach. A more hunched over and inward stance rather than the proud, open one he saw before. Her feet were together and her eyes were shifting and unsure. She looked uncomfortable yet was trying her best to talk to him right now. She was relieved when he shakily took the newly-introduced Lillian's hand and shook it. His grip was weak and gentle, not at all the usual firmness most would apply to a handshake. It was almost like he was afraid he might break her despite her hand being larger than his. His smile was also clearly forced, the edges of his lips twitching. "Um, I'm... Jaime," he said. Hi-me? Oh, Spanish Jaime! Right, she thought he looked Hispanic...

"I, uh, have to admit, I didn't think I'd see you again... or that if I did you'd not recognize me... or would try to avoid me... I wanted to talk to you again. But there was no way I could have brought it up on my own..." Lillian said, shifting a bit in place.

"Yeah, same... So, what are we going to do now?" Jaime asked. His voice was small and his tone nervous. He was kind of adorable, at least in his own awkward way. Though he looked cuter in the dress than he did now, she had to admit. But one might say that about herself when she was naked... or not. She knew from when she tried to wear a skimpy bikini that most people found it distasteful or unpleasant thanks to her shape. It was probably part of the reason she had this secret hobby she did now. "I promise I won't tell anyone about last night... I-I mean, so long as you don't tell anyone what I was doing, either, of course! Do we just... go our separate ways, or...?"

She jumped forward, frantically shaking her head. "No!" she nearly screamed. As the echo reached her and she saw Jaime give a startled recoil, she clapped her hands over her lips. "I'm sorry, I'm sorry, I just... I really wanted to see you after last night." She directed her gaze upward, suddenly finding the walls of the alley interesting. "It's not often I find someone who's open-minded enough to understand me or into things that most people aren't okay with... The moment I saw you, I thought... well..." she bit her lip. She had to be brave while dressed right now!

"I wanted to see if maybe you and I could get to know each other more... and maybe.. I don't know... watch out for each other? I promise I won't tell, but I mean... you understand me, right? What I was doing." She leaned in, causing the androgynous young man to lean back in turn. "It was the same as you! Going out late and hiding from the world but still trying to be yourself... There isn't any better feeling." She gribbed shirt for a moment, feeling the flooding of desires that usually came with her thoughts of stripping, the same ones that fed into her impulsiveness right now and tempted her to show him what she meant.

"I think it would be nice and really fun to maybe hang out together like that... share in our experiences and watch each other's backs, maybe. I mean, that was what you were doing last night right? You looked so nervous but excited, too. It was your first time going out like that right?" He nodded. "I could kind of tell. It must have been crazy. At least in time you could go out as you want and be yourself during the day, it's harder for me to do that," she said, running her fingers through her long, dark hair now in a blatantly nervous gesture.

"I mean, that's what you were doing, right? Living out your cross dressing fantasy... or are you really trans or something? Do you identify as a girl? We can share stories if you want and talk... If not right now, than would you rather it be as our true selves?" She asked, trying to play to what little she knew about this type of thing. Though she began to look worried as he continued to look nervous and uncomfortable. What if she was wrong? What if he was just... like, he didn't have anything else to wear that night? Or what if it was some kind of dare? That meant she was spilling her guts to someone who might not really understand her and the worry flashed over her face.

"Uh, if not, I get it, and I'm sorry for assuming, I just... well I was really hoping I found someone I can share my other side with. You know?"

"Wait." She was surprised when his other hand reached out to gently grab Lillian's own. His grasp was just as gentle as before, only enough to catch her attention rather than hold her in place. "No, you're right. I am a... Well, a crossdresser, I guess. Last night was my first time, so I'm a little inexperienced, but... I understand your... your urge. I admit I'm not really good with, uh... people. Or social things. And my brain is screaming at me to run, but I can't deny it be great have someone with me when I do it. Birds of a feather, right? You don't have to watch your back if someone else always has it."

A shy smile came to her face. He was being honest with her! He wasn't going to wash this away and ignore her! Pulling her hand from his, she turned around to face away from him and couldn't help but smile widely. "Yes yes!" She cheered with a few shameless happy jumps, a bit of her side from last night leaking through. Realizing how odd that must have looked to her new partner in crime, Lillian spun back around and grabbed both his hands. She clasped them tightly in hers, looking into his green eyes. "Ah, I mean... Sorry, sorry I just... I knew I was reading you right last night, I'm pretty good at that kinda thing." She said before releasing his hands. "Um, but don't worry, you looked cute and I know the first time is always the craziest. To be honest, this was my first time in the apartment. The others were in a dark park or ball field before. And a beach or two..." she said, blushing as she felt a wash of memories. Realizing her face was heating up, she shook her hair out and bounced slightly in place in such a way that would probably make everything on her body move if she were undressed. "And I totally want to talk more, though! But I do have to take food to my mom and you were just heading out yourself, right?" She nodded to his messenger bag before she pulled her phone out. "Give me your number and we can text and meet up tonight or something? Maybe I can bring you something to wear..." she said before she blushed and smiled. "Or do you have some things yourself? I mean, you looked pretty comfortable in that dress but..... well, sorry, I'm being too nosy."

...And too close. She realized she was nearly chest-to-chest with Jaime and hastily took a step back. He gestured placatingly at her. "Don't worry, I've got plenty I can wear. I've kinda thought about this a lot before doing it so I've got a few... things... in my closet where my sisters can't find them." He reached into the gun metal gray messenger bag slung over his shoulder and retrieved his cell phone, holding it out for her to take.

Lillian awkward played with her long hair. "I'm sorry, I just, when I get thinking about these things, I start to ramble... and I'm really not sure how to talk about this without being all self-indulgent... and we don't have time so I'm sorry for running off, but I'm super happy we got to meet right now." She was starting to retreat into her shell again. She didn't want to do that though, so she had to hurry through this. She got his number quickly and exchanged her own with him before nodding. "Just let me know where and when works for you, we can do it here or go somewhere else... but it needs to be somewhere we can be ourselves, okay?" She explained, pale and freckled cheeks reddening as she tried to get the idea out without getting too worked up. "Let me know, if um, not tonight but another night, though, and we can talk for awhile... I can even give you pointers on how to look even better, too," she said before turning and quickly retreating before she got too into this. Because when she did, things tended to happen, and most of the time they resulted in her wearing less and less clothing. She couldn't risk that in broad daylight like this...

At least... not until she was sure she could trust him enough. But when she did... who knew what she might be willing to do with him?

Lillian wasn't sure what she was doing anymore. As she sat and ate breakfast, she was barely registering the taste and mostly going through the motions. Her face was a consistent shade of red and her feet were tapping under the table. She was nuts, certifiably nuts! She had just agreed to meet up with a stranger who she barely knew and sent out an open invitation, no almost a promise, that she was going to be naked during their meeting! And what, because she met a boy by chance, thought he could be trusted, and wore a dress?! She was out of her mind, 100% and entirely... Why, why, why was she even considering this! Was she that starved for attention? To share her secret? She was getting along just fine on her own...

Okay, calm down. Weigh the pros and cons, girl. Jaime had a secret she knew about as well so she could use it if he tried to harm her. It was like mutually-assured destruction. Plus, she could bring her whistle or her pepper spray out with her... so there was that. She texted him soon after they parted and he said she should choose the place before hand, so she was in control of the situation. She would have someone new to watch her back, both for safety and... well, to enjoy it. An audience to enjoy her nudity as much as she did and to enhance her own enjoyment of being exposed... And she hadn't had an orgasm as hard as last night's in lord knew how long! Okay, maybe the last one was clouding her mind.

Cons... Well, she could get arrested, raped, her picture taken, her reputation ruined, lose her future scholarships, get kicked out of school. She shook her head. No, those were all risks she took before. She was going to take them with or without his help... So what was the real risk of having him along? He seemed nice, wasn't going to hurt her. What was the harm? She got all the same risks but with a new reward... a pair of eyes to watch her! Besides, she was bigger than him even without counting the inch or two of height she had on him. Why fear danger from a scrawny guy she could sit on?

Biting her lip, she leaned back and covered her face with her hands. "I'm still nuts..."

She spent the rest of the day preparing, planning her route and her idea. It would be a place she knew, one she had been before. One she had scouted plenty of times and would work out in her favor since it had ways of getting out and calling for help should things go bad with him. She went out of her way that day to make sure it was still in the clear and then spent the rest of that hot and lazy Saturday on herself. Shaving everything down again to be smooth from neck to toes, prepping her long black hair so it was clean and full, and even applying some makeup to try and look her best. She even rubbed some lotions to get her body nice and appealing, and added some body glitter to her chest and face after she showered. Just enough, nothing gaudy.

Around 7pm that night her text went out to him. "Meeting place chosen, meet me at 11pm tonight. If you need a ride I can give one. I have a car of my own and we can meet at 10:30 downstairs by the elevator. You can change in the car or when we get there if it'll make you feel better." She groaned to herself and ran her fingers down her body. Her mom had woken up from her mid-day sleep and gone to her night shift already so Lillian was naked in her apartment after preparing. She decided maybe she could add a bit of a glow to her body with some gentle prep down below with her fingers before they got started, but decided against it. She wanted a clear head, at least at first, and would just get horny soon enough anyway. Jaime's response text said that while he had a driver's license, he didn't have a car of his own, so he'd meet Lillian in the apartment complex parking lot.

When the time came to meet she took a deep breath and left her apartment. The door locked behind her and she slipped the keys into her purse. A trip down the stairwell and out the side door and it was just a hop, a skip, and a jump to their chosen meeting spot. She waited by her car in the middle of the parking lot, her fingers tapping the side as she took a steady breath. Wanting to save her exhibitionism for their actual adventure, she'd donned a simple white t-shirt, gray gym shorts, and plain undergarments.

They'd be lost soon enough so she figured dressing up wasn't necessary. But her hair had a slight wavy look to it now and she had her hat off this time around. Her lisp were painted a soft pink and she had on make up just to accent her face and not disguise it too much. She was already eager to strip from how antsy she was getting...

It was just when she was getting worried she'd get stood up that she saw a figure walking out of the building, looking around, and then making a beeline for her car upon spotting her. She'd sent him a picture of her car ahead of time. She would be driving a simple dark blue 2007 Camry. Nothing fancy or expensive. Her mom got it for a really good deal years ago from a patient's family who cut her a deal at a dealership they owned. It got her around and she was happy with it most of the time.

Still, she had to worry about him being able to sneak out so easily. She had the advantage of being an only child and her single mother being out, but what was his family situation? He mentioned sisters, at least. She was tempted to ask via text earlier but didn't want to seem too eager, needy, or pushy.

As he came into view in the dark she saw the figure lift a phone up. At first she thought it was for light but then she saw the list of text messages on the screen. He was proving it was him via their messages. Cute, but what other Latino her age in a dress would be approaching her car at this hour?

Speaking of, as he came further into view, Lillian could see that Jaime had put more effort into passing this time. Maybe the other night was simply an impromptu test run that he rushed before he lost the nerve? This time rather than the awkward dress he was wearing a light blue spaghetti strap ruffle top and a pink layered ruffle skirt that reached his knees. Some white kneesocks and black Mary Janes just in his size confirmed his claim that he'd been preparing for doing this. A glance at his face and Lillian could tell that he'd applied some light makeup. He also looked to be wearing a wig, too.