A Crossdresser & an Exhibitionist

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She had to be nuts, truly and certifiably nuts. This was by far the most risky thing she had done in her nearly year of self-exploration by a long shot. Forget the runs through the park, the local golf course, or the empty mall spillover lot for the holidays. Those were far away from another human soul, unlit and empty, perfectly safe and secure. With her clothes hidden but within reach or a car ready to start up and drive within a few minutes run time, everything was safe and secure. And yet tonight... she was trapped. Trapped in a place that she was intimately familiar with, and very, very exposed.

For the first time she was pushing her limits harder than ever before and taking part in her hobby in a place where plenty of people could know her. The risk was insanely high that someone she knew from her day by day would see her and expose her secret, much like she was exposing herself now.

Lillian crept along the outer edge of the complex’s pool around the back of the building, extremely self-conscious of her massive breasts gently swaying and swinging. It was night but some security lights were keeping the pool lit up enough that no one would try to get a late night dip in without fear of being caught. Lillian wasn’t there for a swim though, she was there for something much more important; something she had hid earlier that day and was praying was still in place. Creeping to the very edge of the pool grounds, she found the pump and reached behind it, wincing at the feel of the machine against her inconvenient breasts. She managed with the tips of her fingers to touch the cool metal object she needed, pulling it out with a cheerful "Yay!" In her hand she held the hidden key to her apartment, pink lanyard attached to one end. She noticed the bounce on her front from the movement of pulling out from the pump, still crouched down as she shuffled backwards. She grimaced, rubbed her breast lightly and sighing.

"Easier when I was dressed,” she muttered as she looked around.

Standing fully now, she would be a true sight should someone come across her in that moment. Lillian, black hair sprawled down her back, smooth hairless skin shimmering in the moonlight and orange glow of the security lights, and soft amber eyes that darted around for any sign of movement, was entirely naked from her toes to her forehead, which only had a black messenger hat atop it. Her curvy body trembled slightly as she stood pigeon toed, fighting to keep her legs from closing tightly together and hands from covering herself. She knew she could get in huge trouble for this but the risk wasn’t comparable to the reward, which to her was far above any punishment. Lillian had been aware of her hobby and need for almost a year now, ever since that fateful night on the beach that turned her life upside down…

For now she had to fight those memories though, and ran as silently as she could, her rounded and pendulous breasts bouncing with each quiet step. Despite her attempt to be light on her feet, other parts of the full-figured girl's body shifted and bounced with her. She loved the feeling herself, but knew that it wasn’t always the most ideal thing to see for others. She was still learning to love her body despite this strange hobby, but every time some part of her curvaceous figure wiggled or jiggled in response to her bare naked movements, she felt pleased to be so plump.

Heading to the stairwell, she was intent on taking the stairs back up to her floor. It was the same way she came down, naked as she was now. She had placed her key for safe keeping that day and left her apartment locked and without clothes, truly trapping herself in this state with only one way to get back in. She had to admit, it was the most thrilling adventure she'd had yet.

However, as she started to the stairs she stopped on the first rounding, hearing someone on the floor above opening the door and chatting with another. The two voices were clear as day as she felt her already pale skin, peppered with freckles on her chest, shoulders, and cheeks, grow so pale the spots might as well be glowing! She darted out of the stairwell and into the first place she could find, pressing a button to open the nearby elevator and diving inside, closing the door behind her. If they had just come down, these people weren’t likely to get on the elevator, and thus this was the best place to hide. Or so she thought as she placed her ear to the wall, waiting and listening to the couple as they disappeared, ready to open the door herself when suddenly she began to move.

“Oh no no no!” She stepped back from the door, terrified. “Where is it going, I didn’t press anything!” She shouted. She didn’t have the sound, collected mind to try and press another button, instead panicking in place as the elevator carried her higher and higher, her hands trembling at her sides as she fought the need to cover. This was it, this was totally it, she was done for! Moving to the side and pressing her bare back and prodigious rear against the elevator wall, she did her best to be unappealing and hoped that whoever opened up the door would let her get past them quickly.

Slowly the elevator came to a stop, and with a chime opened up to reveal a sight almost as curious as herself. Anther person who looked around nervously, not yet noticing her as she got a slow look at them. This was… interesting. A guy was standing outside, wearing a dress! He had a slightly gender-neutral mien over all but it was no doubt to Lillian that he was definitely a guy! The short, unkempt hair, socks, and sneakers that didn't at all match his ill-fitting dress, along with the lack of makeup, made it a sound deduction, though his androgynous facial features and scrawny figure gave her at least some measure of doubt. She stood nervously watching as he got on without really looking, more concerned with the people that might come outside their apartments into the halls before he shut the door and pressed the first floor. Great, she was going back!

Biting her lip, she knew she couldn’t just stand here. She had to get out, but her floor was back up, not down… She had to ride this elevator again. Sure, she could just hope he wouldn’t notice her, and could wait… or she could get off at another floor, but… somehow she felt that this was a once in a life time chance. She was trapped with someone who was in an equally embarrassing situation, clearly doing something that he wouldn’t normally do, judging by his face… Perhaps…. Perhaps she had found someone who might understand her plight? She had to get his attention, and to talk to him just once…

“Um, excuse me?” She questioned, forcing what she hoped was a pleasant, friendly smile despite her red face and heightened nerves. “You mind pressing seven before you get off?” She raised her head to look him in the face with a bold smile, as if nothing was wrong with her own situation. She felt the familiar desire and excitement at knowing she was about to be seen and there was nothing she could do to stop him from looking...