Cross Dresser Flashing for Nude Day

This is a Nude Day contest story. Please vote.

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Having fun flashing the sexy, pretty neighbor his pantyhose clad cock on Nude Day

James, a cross dresser, had some sexy flashing fun planned for Nude Day. Taking a long sensual and sensuous bubble bath first, wanting to look pretty, feel sexy, and smell divine, he took his time getting ready by shaving, waxing, and trimming every hair from his manly body. Even though he wanted to go all out and dress up, not wanting to scare the woman of his desire off, he didn't dare. Rather, much like baiting and waiting, while hoping to hook a fish on a line, he wanted to give her a fighting chance to flee, before reeling her in and winning her heart.

Deciding not to wear a wig, he had several in all colors with blonde being his favorite and, with his fair complexion, he made for a good blonde. With not a strand of hair out of place, he coiffed his hair to perfection, before keeping it in place with a light but foggy, controlled mist of hairspray. He looked at himself in the mirror. With what he was planning to do, he was excited that today was the day, Nude Day.

"If I say so myself, I have such nice hair," he said turning from side to side, while fluffing his hair with his palms. "If I grew it out and wore my hair longer, I wouldn't have to bother with a wig, just a different hairstyle."

Going through his growing closet of women's clothes, he decided to wear the beautiful silk bathrobe he bought when at Fantasy Fest in Key West, Florida, the with the vibrant colored parrots and flowers. A bit ostentatiously bold, as soon as he saw the colorful bathrobe, he had to have it and bought it on the spot. Saving it for special occasions, such as was today, Nude Day, wearing it always made him remember the fun he had walking the streets dressed as a woman at Fantasy Fest. Never had he felt so free, so accepted, and so guiltlessly alive.

He tweezed his eyebrows just enough to make her wonder, is he or isn't he? Resisting the urge to put on a full face, he put on some cover up to conceal his skin flaws, a feather of blush on his cheeks to give him that healthy glow, and clear gloss on his lips to make him impulsively kissable. To make them pop with shine, he wore just a clear coat of nail polish, instead of lipstick red, his favorite color. Wavering back and forth on what to wear or what not to wear under his bathrobe, finally, instead of wearing nothing at all, he decided just to wear sheer pantyhose beneath his robe, instead of panties.

Choosing his flashing victims carefully and preplanning his flashes, oddly enough, he only flashed on Nude Day. Having flashed on different days over the years with mixed success, he deemed Nude Day as his flashing day. Being that he was a man and a cross dresser, doubly difficult for him to flash without being suspected of exposing himself and arrested for lewd and lascivious behavior, he had to make his flashing appear accidental. With today being Nude Day, he readied himself to do a bit of flashing.

With cross dressing his curse and his salvation, cross dressing was his reason to flash and his unique way of finding the perfect woman. Using Nude Day as his cover and his excuse, should he be questioned for and suspected of flashing, his target was the new neighbor, Jill. She moved in the apartment building a few months ago and she was hot. Introducing himself to her, after running into her in the hall the day she moved in and with both of them making eyes at one another, he suspected she was as attracted to him as he was to her. Only, needing to get it all out in the open, he couldn't tell if she was attracted to him as a man or because, perhaps, she suspected that he was a cross dresser.

Before taking the next step, before being so vulnerable and so exposed, and before putting himself out there with his heart on the line, he needed to know if she'd embrace his need to cross dress or reject him for his perversion. More of a fetish, cross dressing wasn't a perversion to him, of course, as it was to others. Yet, he's already been rejected too many times before to waste any more time, money, effort, and emotions on a relationship that would go nowhere. This time deciding not to withhold his secret of cross dressing, he'd rather be rejected upfront.

Just as it does with anything else, the world of cross dressers and cross dressing is no different; it takes one to know one. Hopefully, in the case of Jill, he suspected she'd be openly accepting of his secret life. Perhaps, she was intimately familiar with a cross dresser, an ex-husband, an ex-boyfriend, a brother, or a friend, perhaps. As a cross dressing man, he gets a lot of that, kinky women who feel safe and comfortable enough with him to enjoy experiencing their fetishes and sexual peccadilloes. Saving himself the time and the embarrassment, while enjoying the excitement of accidental nudity, flashing Jill was his kinky way to find out if she she'd accept him as a cross dressing man or not.

Young, pretty, and sexy, he already knew her set routine. Easy to flash the ones that were so predictable, every morning, she'd go out for a jog and return home around the same time. Equipped with a very large cock, James hoped that she'd like what he planned on showing her and what she'd surely see. Believe it or not, most women prefer an average sized man, instead of a man so well endowed. Ideally, he'd love to find a woman who accepted him for who he was without him having to pretend who he wasn't. Actively involved in the parties and social functions that cross dressers occasionally have in the course of the year, he needed a woman who'd embraced his need to cross dress and be part of his social world of cross dressing, cross dressers, transsexuals, and gay and lesbian friends.

Attracted to her by her good looks, of course, encouraged by the looks she gave him, and mostly by the clothes or lack of clothing she wore to go jogging, he decided to flash Jill. Besides, whether a cross dresser or not, what man wouldn't want to flash someone who looked like her his cock? Blonde and blue eyed, at 5'5" tall and not much more than a hundred and twenty pounds, every man in the complex was after her. Yet, James, as different and interesting as they were all so similar and boring, hoped that he'd be the one to win her heart by flashing her his cock. It was a convoluted plan but, in his world of cross dressing, it was a plan that he's had some success with before.

She wore short shorts with leg openings wide enough to expose her panty with every running step she took. Then, when she stretched, especially when she leaned forward, the oversized tank top she wore exposed most of her A cup breasts. Where most men he knew preferred larger breasted women, he was attracted to a woman who had tits small enough for him to fit her entire breast in his mouth. Being that he was such a voyeur and because she was always so freely showing all that she had to sow, he couldn't help but wonder and suspect even that she may be an exhibitionist. His perfect match, certainly, for sure, it would take an exhibitionist woman to have sexy fun with and appreciate a cross dressing man.

A Nude Day flash that James enjoyed doing and had perfected over the years with different victims with some success was his doggie flash. When flashing, he wore his lightweight, cotton bathrobe with nothing underneath, except for very sheer, nearly transparent, pantyhose. Exchanging his cotton bathrobe for his colorful silk and nearly transparent robe, the lightweight flutter of the soft, silk material against his nearly exposed cock continually fluffed his prick and harden his cock. His intention was not so much to show her his cock, as it was to show her that he was a cross dresser.

Yeah, sure, to show her that he was a cross dresser, he could have worn woman's panties without flashing his cock at all, but wearing pantyhose accomplished both, exposing his cock to her and showing her that he cross dressed. Besides, being that it was Nude Day today, no doubt, he'd get away with flashing her his cock. No longer shy about anyone knowing his cross dressing secret, he was especially proud of his big prick and hoped that she'd be, too.

For sure, if he was going to flash her his cock, he'd prefer flashing his cock, of course, while wearing nothing at all. Only, should he make a romantic connection, he needed the woman he flashed to know upfront that he was a cross dresser; it wouldn't work otherwise. With no intention of deceiving her, he had no intention of changing his cross dressing lifestyle for any woman. Instead, he was seeking to find a woman who'd accept him and not judge him and be turned off because he enjoyed cross dressing.

Feeling it was better to be honest upfront than wrestling with guilt and trying to explain later, after having already started a romantic relationship, he was tired of making excuses that he didn't want to make and/or lying about what he did in private because he must. Telling the complete truth from the beginning was the best way to begin a love affair with a woman. With all the guilt and angst that tortured his soul in the past, once he started feeling romantically connected to a woman, it was always more difficult to explain later that he was a cross dresser.

Not many women understood cross dressers, but he had a funny feeling that Jill was not the typical woman. He hoped she was sexually uninhibited and didn't mind taking a walk on the wild side with him, as his partner in erotic adventure. All in one fell swoop, so to speak, flashing Jill his big prick and exposing himself as a cross dresser was enough of a surprise. Nonetheless, it was better she found out now that he was a not only a cross dresser but also a man with a big cock, instead of later.

While watching out the window, waiting for her to round the corner in the distance, and run the straight road that ran down and across from their apartment complex, he readied himself by stroking himself to a big, hard erection. The excitement he felt before flashing her his cock was exhilarating. The constant sensation of the flutter of his silk robe and his tight pantyhose fabric brushing against the head of his stiff cock, as if giving his penis a gentle massage, maintained his erection and made him horny. Once he saw her, having already timed her run from where she was now to the apartment complex, knowing exactly how long it took her to run to the apartment complex and how long she stood outside stretching, he waited, watched, and listened, while counting the seconds tick by on his watch.

Tick, tick, tick, tick, with every tick of his watch he became more excited with what he was about to do. Tick, tick, tick, tick, he wondered what her reaction would be to discovering that he was a cross dresser and to seeing his big, stiff prick. Tick, tick, tick, tick, would she reject him because he's a cross dresser? Tick, tick, tick, tick, would she stare at his cock or, once seeing his big prick, would she turn away in horror? Tick, tick, tick, tick, would she reject him from the shock of learning that he enjoyed wearing women's clothes and/or from seeing his big prick or both? The reaction of the flashing victim was an important part of flashing and either way, if she stared or looked away in horror, flashing her would give him plenty of masturbation material later.

Filled with pure adrenaline, raw testosterone fueled his sexual excitement. When he saw her running towards the apartment complex in the distance, he left his apartment and stood poised on the stairs waiting for her to open the outside, front door. He hoped no one else would come in or out and go up or down the stairs, otherwise his flash would be ruined. He didn't need another person interfering with his flash. He's learned through experience that the reactions of his victim were very different with a third party interfering.

He knew she was downstairs, just outside the front door. He could see her shadow against the stairway wall and her reflection in the glass door, as she stretched, before entering the building. Thinking about her making all of these wonderful sounds in bed, he could hear her huffing and puffing from her having finished her run and he heard her moaning and groaning from stretching.

Prepared with his back to her, he held his dog's leash in one hand and his just delivered newspaper in the other, while standing near the top of the stairs, a few steps from the second floor landing. Then, when he heard her open the front door and begin climbing the stairs behind him, it was show time. In readiness of his doggie flash, he climbed the few steps to the second floor landing, while talking to his dog.

"That's a good boy. He's a good dog. No, it's okay. That's just Jill. Easy, boy, easy. Be nice. Don't growl and no barking," he said exaggerating whatever his dog was doing or not doing.

"Hi James. Hi Buster," said Jill approaching behind them.

"Hi Jill," said James turning his head, as she slowly climbed the stairs.

Then, in an act of preplanned, neighborly courtesy, so that his dog didn't snap at or jump on his new neighbor, he scooped up his dog, while accidentally on purpose collecting the hem of his bathrobe in his hand, along with the dog. He had practiced the swift move to make his flash appear accidental. All in one movement, scooping up the dog, lifting up the hem of his bathrobe, and turning to face her, it was such a fluid flash that every woman who witnessed his practiced flash, whether in pained horror or sexual excitement, looked, stared, or turned away in shocked embarrassment. Then, to delay her departure and to make sure she saw what he needed her to see longer...Oops...he dropped his newspaper and watched it spill down the stairs.

Inherently having a good sense of who to flash and who not to flash, whenever he pulled this flash, always his female neighbor would gladly walk back down the few steps to collect the newspaper for him and walk back up the stairs to deliver it to him, all the while ogling his exposed cock. The flash usually worked like a charm. Just as Jill had done, some neighbors would even engage him in conversation, while standing a few steps lower, for a better vantage point for them to stealthily stare at his cock. Yet, Jill was different. He really liked her Important to begin a relationship honestly, admittedly, even though to get her attention, he stacked their fated deck by flashing her, while wearing pantyhose, she accepted him for who he was, a cross dressing flasher with a big prick.

Had it not been Nude Day, he never would have dared, even flashing Jill. Yet, the fact that it was the day of nudity made it easier to flash. Perhaps, Jill doesn't know that today is Nude Day and perhaps, after he tells her, she'll flash him, too.

With those women who told him that he was exposed or their reaction told him that he was so exposed, he'd apologize profusely, just as he did with Jill. As much as the flashing, it was the reaction received that he needed. No matter, his flash worked without her ever suspecting that she had been purposely flashed.

Such a preplanned and orchestrated flash, it was a perfect flash. If she walked away embarrassed or shocked and didn't bother to help him pickup his newspaper, he knew that she wasn't interested nor was she the woman for him. If she walked back down the stairs to retrieve his newspaper for him, he knew she saw his cock, wanted to see more without him knowing that she was looking, and was interested in what he was showing and all that she saw.

"Oh, dear," he said acting discombobulated, while struggling to hold the dog with one arm.

"That's okay, James. I have it. I'll get the newspaper for you," she said, while looking up at all that James was showing.

With his bathrobe lifted nearly to his waist and the hem tucked beneath the dog, James exposed the full erect length of his pantyhose covered cock to Jill. Already practicing the move in the mirror in his apartment, he knew his new neighbor could clearly see his cock and balls. Had he not waxed off his pubic hair, she'd see that too through the nearly transparent fabric.

"Thank you," he said with a wild smile.

Jill retrieved all the sections of the newspaper. Then, as she put the newspaper sections in order, she slowly climbed the stairs, while never removing her eyes from James' cock. She handed the newspaper to him and, now at eye level with his engorged cock, she stood a few steps down from him, still staring at what he was showing.

"Whew, I'm tired after running," she said leaning lower in front of him, as if stretching on the stairs, and aligning her body in an eye level posture that gave her an even better and closer view of James' package. "Normally, I'm invigorated from my run but, today, I'm a little flushed," she said looking up at James' face, while standing and waving her hand in front of her face, before casually casting her eyes downward for another look at his cock, again.

"Running isn't for me," said James hoping to engage her in conversation to make her stay and stare longer at his exposed prick. Imagining her reaching out to touch him, feel him, fondle him, and stroke him, before taking him in her mouth, he felt his cock pulsate with the length of her stare. "I'd run if I had a partner. Still, I'd rather do other things instead, such as riding a bike to jogging."

"Well, any time you want to go for a run, let me know and we can go together."

"Sure, I'd like that," said James, "but I think I'd slow you down."

"Well, I have to go and take a cold shower," she said walking ahead of James and Buster. "It was nice to see you again, James, all of you, I mean both of you," she said giving him a wide smile, a wink, and a laugh, before staring at his cock, again.

When she turned around to look at him again and said that, James looked down to see where she was looking. He pretended it was then that he realized he was so exposed. If there was an award for flashing his cock accidentally on purpose and pretending he didn't know he was showing, he would have won the Oscar.

"Oh, my God, Jill. I'm so sorry," feigned James, while brushing down his bathrobe. "I'm so embarrassed. Please forgive me. I had no idea I was so exposed. It must have happened when I picked up Buster. With wearing the pantyhose, I didn't even feel a chill," he said with a haughty laugh and a brazen attitude.

"It's okay, James. Don't fret. It's nothing that I haven't seen before and it's nothing for you to be sorry about," she said pausing to make solid eye contact with him. "If anything, you should be proud," she said with a little laugh, before climbing the rest of the steps on her way to her apartment, stopping, and turning. "If you forgive my forwardness," she said looking up and down the stairs to see if anyone was coming and lowering her voice to a hoarse whisper, "you have the biggest cock, I've ever seen in my life. To be honest, I couldn't take my eyes off of it," she said turning red and waving her hand in front of her face. "Sorry, it's been a while, since I've had sex," she laughed. "Only, I didn't know you were a football player."

"Football player? I'm not a football player," said James laughing. "Why in the world would you think that I play football?"

"The pantyhose," she said.

"Oh, that," said James fluffing up and parting his silk robe enough to flash Jill his cock again. "Actually, even if I were a football player, I surely wouldn't be wearing pantyhose in July. I don't know how you women do it. It's so uncomfortably hot," he said laughing. "I hope you're not offended, but I enjoy wearing women's clothes," said James lowering his voice to keep their conversation private. "I'm not so terrible fond of pantyhose, though. Hard to get on, they're even more difficult for me to get them off, without running them and ruining them."