It All Goes Wrong, Pt. 01

It All Goes Wrong, Pt 1

(Crossdressing) Crossdressing fantasy adventure

By ChangeYourPassword

Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story and the fetishes involved, great. If not, please forget the whole thing.

He had been a cross-dresser since he was in his early teens.

Sampling his mother's things when he was home alone. Always carefully putting them back afterwards. Embarrassed and afraid she'd find out.

In high school he pushed those pursuits aside, and focused on his studies, sports and girls, realizing at that time that he wasn't gay, just slightly bent.

But his fetish was always at the back of his mind, and it held him back from ever developing a full relationship with any of the females he dated.

That situation continued all the way through college and when he joined the working world. Outside work, he dated, he partied and played, but he didn't find a woman who he felt comfortable building a relationship with, one with whom he might share his little tale of perversion.

So, he lived alone in a small bungalow, spending his spare weekends fixing the place up.

And on those weekend nights, after a quick shower, he played and practiced with his female persona, before getting himself off in the shower.

Before stripping though, he always examined himself, his clothes, make-up and mannerisms, to rate his ability to pass. Could he, someday, build up the courage to go out in public as his dream-woman?

His wardrobe slowly grew via on-line purchases, and his make-up skills improved as he watched more YouTube instructional videos.

He considered himself lucky in that he wasn't the biggest or most rugged man on the planet. Actually, he was thin, and only average in height, and his face remained thin and boyish despite his age. That meant that finding and fitting the clothes he loved, wasn't difficult, and that makeup could successfully transform him into a her.

Over time, he became convinced that he could, and should take that big step to live his dream.

He started with small little adventures. Just going out for a drive after dark. He upped his game by hitting a drive-thru for a fast-food burger. Then stopping for gas at a Quicky-Mart.

After a few more little adventures, he built the courage to visit a restaurant for a late dinner. Of course, he picked a place far from the neighborhoods where he lived and worked. And, surprisingly enough he had a good time, and no one paid him any undue attention. Although he thought he caught someone at a nearby table checking him out. That was exciting.

And at night, before he fell asleep, he dreamed about scenarios where he would dress always as his fantasy girl. And in some of those situations, he even considered being forced into it. Perhaps by some strong, accepting and loving woman. Ah, fantasies...

After a couple of months of similar little escapades, he began dreaming of a more complete and exciting adventure. And the more he thought about it the more intrigued and aroused he became.

He'd take his annual, two-week vacation, and spend it entirely as a woman. During that time, to make it even more thrilling, he'd spend one entire week, seven days, in the big city. He'd force the issue by driving there, and only pack dresses.

He'd have to spend the entire adventure trip as a female, amongst the strangers, playing at being a tourist. Seeing the sights, eating, drinking and clubbing as a 'she'.

Just the thought of it drove him to a hot shower, and a glorious masturbation session.

The decision made, he excitedly spent the three months leading up to his ultimate adventure, planning and accumulating a wardrobe suitable for the trip.

He also focused many more hours on his looks. Makeup, manicure, hair - all of the needed feminine skills. And as the time passed, the practice worked, and his confidence rose.

As he finalized his vacation plans, his excitement continued to grow, and he spiced things up even more, by establishing steamy challenges and rules for his trip. Of course, every new requirement made him hornier and his libido forced him to stop and get himself off.

Naturally, he'd wear a gaff at all times, to hide his bulge, and sexy panties over the top. He bought pretty and functional corsets. Real ones, stiffly boned to deliver a three-inch reduction. He knew it would be uncomfortable, but he absolutely had to have a nice shape, and besides, the bodily restriction was also a turn-on.

Dresses or skirts, short ones, would be worn throughout. Never pants, jeans or shorts.

Stockings were a must, no pantyhose and no bare legs, ever.

Three-inch, spike heels would be worn at all times. He practiced constantly to make sure he could walk comfortably in them for long periods. He still wound up with sore feet and legs, but that was part of living as a sexy woman, wasn't it?

Makeup would always be heavily applied to give him the sexiest and most feminine looks possible. With enough cosmetics, he was convinced that his face did look like a woman's. Certainly, no ten, but perhaps a six, on the male-applied rating scale.

And properly polished and extended nails on his thin fingers were a requirement. He practiced applying them until he was able to produce a reasonably pretty look.

It was all coming together, and his excitement was keeping him up late at night, fantasizing happy times.

But still nervous, and afraid of the distinct possibility of discovery and humiliation, he decided to perform one last test before he committed to his big adventure. He'd make a trial run in the weeks before his scheduled vacation. For that, he'd spend an entire day and night out as a woman. Away from home, among strangers, living the life of a pretty woman. As pretty as he could make himself, anyway.

Afterwards, if all went well, he'd make his final commitment.

++++++++++++++

Andy now Andie, was packed and ready by six that Saturday morning. She had planned everything carefully, and was prepared to spend the next twenty-four hours away - dressed beautifully as a girl.

Dressing for her test run was exciting in itself. She had staggered out of bed at three, an ungodly hour, but she had hardly slept anyway, so thrilled was she. She'd taken her time, savoring every minute. The corset was, as always, tight and uncomfortable, but it and the breast forms gave her a wonderfully feminine shape.

Her hairless legs felt luxurious in their nylons. She shaved her legs regularly these days, and loved the feel of it.

The dress and shoes she'd selected, with a lot of effort, were the perfect combination of sexy, casual and elegant, in a pretty color that suited her well. And the dress and shoes matched perfectly.

Most of her time that morning, was spent on her makeup. It too had to be perfect if she was to pull this off. It took her well over an hour, with several redos of various aspects before she was satisfied.

She'd polished her nails the evening before, so at least they were ready.

Finally, she donned her very expensive wig, brushing and arranging it to perfectly frame her pretty face. The thing fit like a glove and was securely attached. You get what you pay for, she thought happily.

Admiring herself in the mirror she was very pleased, as well as relieved. This could work!

Heading out so early was the first part of her strategy. She didn't want any of her neighbors to see a woman driving away from his house, in his car.

But as she also wanted to have a hotel room, available just a relatively short drive away, she had actually reserved the room for two nights, Friday and Saturday, even though she would only be there for the second one.

On Friday morning, she had called the place and informed them that due to unforeseen delays she would be checking in, very late, perhaps even the next morning, but she wanted the room available so she would pay for both nights. The desk manager was happy to oblige. The room would be waiting whenever she arrived, even if it was at dawn.

The drive was uneventful, and that was a relief, she had been worried about getting in an accident or being stopped for speeding. Dressed as she was, but with Andy's identification, it would have been a catastrophe.

She arrived at the mid-level hotel a couple hours later, and after parking in the lot, she changed her shoes before she grabbed her roller-bag and headed for the door.

She had worn a pair of moccasin slippers for the drive, shifting to her pretty heels before getting out of the car. She wasn't experienced enough at driving in high heels to risk it for the trip.

The drive for her big vacation stay would be a lot longer, six hours to get to the big, LGBTQ-friendly metropolis where she'd spend her week's adventure. She certainly wasn't confident enough to deal with that distance in heels, so she'd be following the same procedure then.

It was in changing the shoes that she ran into her first problem. Her stiff corset made it difficult for her to bend and reach, while sitting in the cramped space of the car. She finally had to open the car door, and swivel in the seat, showing a lot of leg, and stocking tops, as she slipped off her slippers and buckled the ankle straps of her pumps. The stiff corset forced her to hold her breath throughout the painful process.

Inside the lobby, the sleepy clerk behind the reception desk paid no attention to the small discrepancy in names on her ID. Andie was close enough to Andy. He thanked his parents for providing him with such an amorphous name.

Soon Miss Andie had her key-card and was secure in her room.

There, she collapsed onto the bed, giggling as she breathed a huge sigh of relief. She'd made it!

Twenty minutes later, feeling much calmer, she unpacked her things, touched up her makeup and headed out to walk, and window-shop the few blocks to a nice breakfast place just down the block.

She'd done a ton of research, on-line, and now knew the area well. So, after her meal, she again strolled the several blocks to the area's large, open-air shopping mall. Her timing was perfect, the stores were just opening when she arrived.

She spent the rest of the day, window shopping and people watching. Of course, she focused on the other women. In part to determine if they gave any indication they detected something wrong with his Andie. But also dreaming about spending time with one of them, as a pseudo-lesbian couple. That would be the ultimate experience!

While she was eating her lunch, she realized that she hadn't actually made a purchase. She'd visited plenty of stores, scanning all of the women's fashions, but although several things, clothes, jewelry and makeup had caught her eye, she hadn't yet bought anything.

That just seemed wrong, so she gave herself one special challenge. She'd purchase a pair of shoes. Pretty ones, with heels taller and sexier than the pair she was wearing.

After a leisurely meal, accompanied by a very nice Chablis, she began her quest. She passed several women's shoe stores before she found one that looked well stocked with pretty and sexy shoes, not just the casual, comfortable and sporty footwear that were so popular with the women she'd been observing.

Examining the inventory on display, she became increasingly excited. They were so pretty, and sexy, and the heels so high!

Finally, she had selected a couple of pairs she didn't think she could live without. She just had to have them!

As the saleswoman helped her, she became so turned-on she was afraid her bent-back cock might burst out from between her legs, tearing through the gaff and her pretty panties. The thought and the picture of it in her head, made her giggle, and drew a confused look from the staff member.

"I'm just so delighted by these shoes," she explained, self-consciously.

The woman nodded, "I understand, they're beautiful, but awfully tall. Have you worn ones like this before?"

"No, not yet, anyway. But I'll learn to walk in these."

"Just be careful, okay? No broken ankles." She said, but added a chuckle.

Andie laughed, but she did start worrying what would happen if she did fall off her heels and had to go to the emergency room. That would certainly ruin everything.

She paid and left the store, happy, but also subdued, and a lot poorer.

But her worries evaporated just a block later, as she came upon a jewelry store with a nice display window.

As she inspected the jewelry, a thought struck her. She didn't have a ring. She knew first hand, that decent guys always checked a woman's ring finger to determine if she was married or available. And without something on that finger, there was the potential for some guy to try and pick her up. And she didn't want that.

It only took her twenty minutes to find a ring she thought suitable. It could pass for an engagement ring or just a decoration, one that a woman would understand existed just to discourage.

The salesman seemed to understand as well, but he made no comment. He was just happy to get the sizable commission on the piece.

Andie walked out satisfied, but unable to do any more shopping as she had blown her entire budget on the shoes and the ring.

It was getting late, anyway, and her feet hurt - how feminine was that - so she headed back toward the hotel.

"God, that was fun," she mumbled to herself as she neared the building. By then her feet were indeed killing her. She just wasn't used to that much walking, outside in heels. And her squished and very excited cock hurt, too.

As soon as she got back to her room, she stripped down, and jumped into the shower to give herself the orgasm she so badly needed.

After a nap she spent more than an hour reworking her makeup and dressing for dinner.

The restaurant she had chosen was elegant and dimly lit, and she settled into a small table to enjoy herself and celebrate the success of her little adventure.

The meal was excellent and she realized that a couple of the men, seated at tables around her, were watching; checking her out. It both excited and frightened her. She appreciated the compliment and the affirmation that she did look like a real girl, but she certainly had no interest in them. She made a point of showing off her new ring, to discourage any advances.

After dinner, feeling brave, she drove the short way to a gay bar that she'd located during her research of the area. As she pulled into the lot, she reminded herself that this was just another experiment. She had no intentions of hooking up with anyone. That was not part of the plan. And she didn't have the courage to even think about sex with another girl.

But it was an attractive dream.

The place was cozy and populated equally with men and women.

She thought it was nice, not having to worry about getting hit on by some horny guy. But some of the women were equally as scarry. Andy would have called them dykes.

She found it difficult, but she did succeed in making a couple of acquaintances; women who were friendly and attractive. Ultimately, she wound up turning down one girl's offer to go back to her place, for a late-night drink and some fun. The offer did excite her, but she wasn't ready for anything like that. She had no idea how to deal with explaining that she had a cock. Would the girl be interested or freak out at the prospect. Best to leave that alone.

Well after midnight, she staggered back into her room feeling proud, relieved, sexy and happy, not to mention drunk. After locking the door, she simply stripped off her dress and shoes, and climbed into bed still in her gaff, corset, stockings, wig and makeup.

She knew she only had about three hours to rest before her alarm would wake her and she'd have to get back up and head home. She had to get back home before sunrise to again dodge the neighbors.

She safely arrived there before breakfast, Sunday morning, having slept, and then checked out insanely early. After her busy day, it was difficult, but necessary.

All was quiet as he parked in the garage, walked through his door, closed it carefully and then breathed a huge sigh of relief.

But then he started giggling, and after a minute or two, it turned into a laugh. From there it became almost hysterical, as he danced around his living room, overcome with emotion.

"I did it!" he said to no one, as he began to calm down.

He'd spent the entire time frightened but mostly excited.

He'd been scared to death that he'd be discovered. But he'd also spent that time thrilled to be living his dream.

And now, home, mission completed, he was relieved, ecstatic and feeling horny as all hell.

Cutting short his celebration, he stripped off all of Andie's clothes and again jumped into the shower to reward himself.

He was absolutely overjoyed at the success of Andie's day-out, but he was exhausted and sore from both the shoes and the corset, so clean and emptied, he crawled into his bed, naked, to catch up on his lost sleep.

It took him a while to wind-down enough to actually fall asleep. He was still reviewing the success of his little game, and how horny he still was, when he finally drifted off.

+++++++++++++++++

The time leading up to his vacation was glorious. Work flew by, as he finished the important projects and shelved the lesser tasks to await his return.

Reviewing his successful try-out adventure, he determined that Andie's shoe-shopping challenge had been one of the many highlights of that fun day, so he decided to include several more challenges in his plans for the big event. And the more of those he added to his plan, the hornier and more enthusiastic he became. And the challenges, and challenging rules he developed got even kinkier and more exciting. He'd fulfill many of the fantasies he'd dreamed of over the years. Why the hell not?

First, he decided that Andie would wear ultra-sexy, four-inch spike heels for the duration. Her feet would get sore, he was sure, but she'd look and feel so good it would be worth it.

He also wanted her to have longer nails, polished and pretty. They'd look so sexy and alluring. He'd need more practice of that skill.

He had loved the way the corset had felt, hugging her so tightly, restricting her so firmly, forcing her to stand so elegantly. He'd order a more severe set of corsetry. And she'd wear them all day and all night, except for one hour per day for bathing. It might be miserable, but it would be so very erotic.

That was another thing, he'd require. No showers, only baths. Heavily scented bubble -baths.

And as to her wardrobe - he'd ensure that her dresses and skirts were very short to show off her legs, and perhaps even her stocking tops.

That mandate made him laugh; heaven forbid if Andie were to flash some poor slob. Although, she wouldn't mind showing off to some pretty lipstick-lesbian.

While he was shopping for bras, sexy ones, with a little padding, it occurred to him that Andie should have a larger chest. He ordered breast forms, that would give her D-cups. Of course, then he had to go back and adjust the orders for several of her dresses, to make sure they'd accommodate her new chest.

Finally, he decided that Andie should have a more luxurious mane. He searched and then ordered a new wig that was fuller, longer and a brighter, lighter blonde than the one she already had. And this one was literally the best money could buy. They bragged that it was as close to a real head of hair as could be produced, and that it wouldn't come off in a hurricane.

Over the next couple of months all of the things he'd ordered for Andie's big adventure arrived in the mail. And each delivery was like Christmas all over again. It cost him a fortune, but he'd thrown any consideration about budget out the window. Everything he added to his collection could be worn again for more fun, later.