A Crossdresser and an Exhibitionist Ch. 01 – Exhibitionist & Voyeur – Free Sex Story

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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 two months 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 begin 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-to-day life 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 enormous 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 essential. 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. Her only stitch was a black messenger hat atop her head. 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 gigantic 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 two months now, ever since that fateful night on the beach the day after her eighteenth birthday that turned her life upside down…

For now she had to fight those memories though, and ran as silently as she could, her round 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 at all times the most ideal thing to see for others. She was still learning to Love her body through this strange hobby, after all. 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 discover, pressing a button to open the nearby elevator. When it finally slid open after what felt like an eternity, she dove inside, heart pounding during the wait for the door to close 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 wondered 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 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 inconspicuous 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. Another 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 leastsome 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-lifetime 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 figure out her plight? She had to get his attention, to talk to him just once…

“Um, excuse me?” She spoke up, 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…

In truth, she probably could have gotten away with it. Had she just stayed quiet and slinked back to the corner of the elevator until he got off, he might have never noticed her. But where was the fun in that? Her hobby was all about the risk, after all! She had come out here with the intent not to be seen and not to be caught, but she was. Therefore it would be unfair not to reward the person who was out here this time of night with the prize of catching her! Personally, if someone didn’t point out a boy in a dress or a naked girl to her, she’d be pretty upset with them for a long time!

Plus he was no threat. He was dressed oddly and clearly enjoying his own hobby. He looked nervous, so maybe this was one of his first times! Oh, the very idea was so cute! She thought if this was how she looked when she did her first time? Well, not the first first time, she knew how that went. But the first time she was doing it elsewhere, in the park, alone and afraid. Not only that but he had no pockets in that dress, so nothing to hide a phone in, meaning he wasn’t able to take any evidence. There would be no proof, so it was the perfect opportunity to have some fun!

In response to her query though, he jumped nearly twice his height! His response made her squeal and jump back a bit too with a nervous grin, putting her hands to her lips as she hid her expression. “Oh gosh, I didn’t think I’d scare you that badly,” she said, smirking behind her hands as she watched his eyes with her own. Her eyebrows raised as she saw they swept over her body without hesitation. Damn, he wasn’t even pretending not to look! Just staring her over, memorizing every curve, every freckle and every bounce that her bare skin gave with her simple shifting and breathing. It was almost intoxicating to be ogled liked that and not be seen with disgust, but enjoyment… The way his deep brown eyes scanned over every square inch of Lillian’s ocean of exposed skin, no doubt bidding her nude portrait to memory so he could masturbate to it for years to come… It sent a sexual shudder through her body.

After staring at her for what seemed like ages but was likely only a minute, the boy seemed to snap back to reality. Realization of the full situation looked to wash over him, and he blushed and gripped the hem of his knee-length skirt. Did he just remember it was there? Or did he think maybe something under it might be trying to show off? She grinned at that wondered, honestly.

He seemed to remember her request and nodded, looking numb with shock. “Uh, sure.” He pushed her floor and then looked at her face. Pity. He had been enjoying himself, but now he remembered social etiquette. It was at all times interesting to think about how people did that. At least he did sweep his eyes over her nude body one more time after pressing the button before his eyes settled forcibly on her face, so he at least had some healthy, hormonal urges going on. He was cute, she would give him that, dress and all.

He looked to be about her age, and just an inch shorter at 5’3″ at that. He had the kind of scrawny figure of someone who didn’t really get exercise but just had a very active metabolism. The sun-bleached color of his hair and the tanned olive color of his skin led Lillian to think he was Hispanic or Latino. He had an androgynous face with not a hint of facial hair, though the lack of makeup and masculine eyebrows meant he didn’t look fully female if you really scrutinized his details. That said, his hair was full and down to his neck, so with a bit of growing and styling the thick locks could make for a feminine hairstyle. The spaghetti strap Hot pink dress he was wearing also showed that he had a surprisingly elegant neck and shoulders, if one ignored the Adam’s apple that was visible if you looked close enough.

As they reached the first floor no one waited to greet them and she looked to him curiously. He didn’t get off. Instead he remained staring at her until the doors closed again and she found herself heading back up with him. But now he looked to find the floor far more interesting than her, making her pout slightly.

“Hmm, didn’t you need to get off?” She asked as she moved a bit closer, her heart hammering in her chest so loudly she was sure he could hear it in that tiny space. “Weren’t you gonna go and enjoy the town like this? It’s a nice dress, something that would be fitting for a night out.” She smirked and shuffled to the side. She tried to get in front of him, between him and the door. “You know, if someone saw us like this, they might think you stole my outfit,” she teased. The light laugh she gave caused her massive breasts to bounce, which was enough to draw his eyes to the pale protuberances. She blushed, knowing he could tell that her pink, inverted nipples were poking out in obvious arousal.

Every movement she made caused a corresponding anatomical reaction to Lillian’s breasts. In turn, each jiggle caused the crossdressing young man to reflexively look at her huge, bare breasts, then snap back up to her face. His mouth was moving, but no sound was coming out. When he finally made noise, it was just a pitiful “I, uh… Yeah…”

She laughed again, aware of how it made her body move, from her curved stomach with its own slightly rounded shape up to her breasts which were massive and proud, bare for him to admire. But she had long since come to terms with the fact that it was beyond her control. Her body wanted to move and behave how it chose and it was always going to do its own thing. Though when she was exposed like this it got so much more Free reign it was hard to deny, nor stop, the self-conscious arousal that filled her, even if she wanted to. Still, she was doing better than him! Words were clearly failing him and she almost wanted to ask if it was because of what he wore, or what she didn’t

When he gave up and directed his gaze forward to the elevator door, she tried to peek around him. For all her nudity, she had yet to fully see a guy naked, so she wanted to see if she could get a read on his figure under that ill-fitting dress. As her soft amber eyes drew to his abdomen, she could swear she saw something slightly tenting his dress… If it was what she thought it was, then it was clear that it was because of her! Or… wait, was it because of him being seen? Oh, it’d be wonderful if it was both! She felt even more gratified when, thinking she wasn’t looking, the young man reached down to adjust his bulge.

“Well, be sure to head back down when we get to my floor, okay? I don’t want to make you forget what you need,” she said. It was barely after her sentence was finished that she heard the elevator chime and the doors open to her floor. She had taken enough risks for one night. She needed to get off (double-entendre intended). Walking through the elevator door, Lillian whirled around to face him with her arms clasped behind her back, leaning forward a bit. The action caused her massive watermelons to give a mighty swing, something that drew his gaze to those huge, pale funbags. She smiled and winked at him. “Enjoy yourself tonight!” she cheered. There were so many different ways to take that, of course.

As she reached around in front of him and pressed the first floor button for him, she looked into his eyes and gave a more genuine smile, even accompanied with a flush to her cheeks. “Thanks for looking. Makes a girl feel like she’s actually pretty once in a while,” she said in a husky and throaty voice, one that even surprised herself. Putting on airs to tease him was easy, but admitting something like that, she was feeling suddenly vulnerable. She leaned back out of the elevator, waving in such a way that she knew sent her huge boobs jiggling. It was the sight she left him with as the doors slid closed, cutting off his sight of her naked body.

After the doors closed, Lillian let out a heavy sigh, nearly falling to her knees as she leaned her Hot flesh against the cold doors of the elevator. “Oh, ehm, geee! What was I thinking! I totally exposed myself to a boy in my own apartment complex! There is no efficient way he won’t see me again! Oh god, what if he tells his friends or brothers… What if they go looking for me another night…”

One of Lillian’s hands moved to her abdomen, pressing into the softness of her tummy. “But I can not just not do this again after all that. But… ahhhh, I’m so nuts!” She laughed, amused by her own shenanigans. “But damn… it felt good! He looked at me so much… To think little, curvy me is something worth looking at and even adjusting yourself over… ” She ran her hands over her breasts, shuddering a bit at her fingers on her sensitive skin. Her nipples had been hard and ready the entire time, something she idly wondered if the crossdressing boy had noticed. That, and if he could smell the arousal she felt. Her legs did a good job of hiding the moisture thanks to their curved shape and lack of ‘thigh gap.’ But that elevator was pretty cramped…

Walking back to her apartment now, she didn’t run into anyone else and unlocked her door, heading straight to her room and falling back on her bed, legs spread and fingers touching along her thighs. “Hmmm, and he was so cute, too… wearing a dress and all, my my…” she moaned out and whimpered. “I wonder… if I can use that for a nice topic of conversation…” She bit her lip, then laughed. “No no no, I can not hope to face him again. What would he even say!?” She rolled onto her front, soft breasts flattening against her bedsheets.. “Damn… I want to know…”

It was a Friday night, so she could sleep in on Saturday morning. Her mother was the only other person living with her and she had been out all night. Mama DioGuardi wouldn’t be returning home until well after seven the next morning. She’d slip in quietly, without disturbing Lillian, and what was most important, none the wiser of her daughter‘s continued hobby.

Or the Masturbation session she was about to indulge in.

Lillian spread her legs, hands finding her sopping wet Pussy. Much like the entire rest of her body hair, she’d shaved her puss bare as well. In her eyes, it made her all the more exposed to the air and eyes. She started gently stroking her Pussy, but after the stimulation of tonight, she realized it wasn’t going to take all that long to get off. Once she found a good position to play with her clit with her thumb and play with her lips with her other four fingers, she moved her Free hand to her breast. Compared to the dexterity to finger herself with one hand, the strength to lift one of her mammoth mammaries and suck on the little pink erect nipple required more effort. But it was worth it! And she could rub the sensitive underside of her breast while she did it, so plenty payout for the effort! Lillian couldn’t cum from breast stimulation alone, but it certainly helped when used as a side dish during Masturbation!

Just as Lillian thought, after the extreme exposure play of the night, she was Cumming in mere minutes. Multiple times! Were she not so caught up in her climax, the naked girl would’ve been worried the neighbors would hear her muffled screams and assume there was a murder! The exhibitionist was nearly crying by the time she had her fifth climax, which petered out as she collapsed from exhaustion. Whew, good day… Now she sleeps.

-o-

Lillian DioGuardi had long realized she was an exhibitionist. A chance encounter causes her to meet Jaime Lopez, who happens to be a crossdresser. Realizing their “hobbies” might be of mutual benefit should the two team up, Lillian wants to explore their interests together. Him crossdressing, her exposing her nude body. He agrees, and the two begin a very odd friendship. Could a relationship built solely on a mutual convenience blossom into Love? This unconventional Love story slowly unfolds over the years, detailing the ups and downs of their Love and kinks, all stemming from a fateful encounter and an elaborate dance between a crossdresser and an exhibitionist.

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