It All Goes Wrong, Pt. 01

And while he waited for the big week, he practiced, every evening after work and every weekend.

Those sessions, although at times laborious, were fun, and they kept him horny and focused on his fantasy journey.

He spent hours on makeup, watching innumerable videos on YouTube, until he felt his results were about as good as he could get. Andie wouldn't be a beauty, but she would confidently pass for a girl.

Intermixed with those efforts he taught himself to fumble through the art of the manicure, adding short extensions and polishing to perfection. His nails weren't anywhere near as good as the professionally done ones he admired on the women he encountered, but like everything else, he felt confident they'd pass.

He forced himself to wear his high heels around the house for at least an hour, every night and two hours on weekends. After a while his legs and feet stopped hurting and he gained confidence, He also bought a big mirror so he could perfect his walk, swinging his hips like a woman. He had some success at that, but he wasn't really satisfied.

He also forced himself to spend hours, and then a full day in a new corset. Cinching the heavily boned undergarment down to the full four-inch reduction that he'd established as Andie's goal. He finally made it, but it was hell, and he didn't know how Andie would ever survive a whole week tight-laced like that. But it was a rule, and he'd committed to following all of them.

And, he spent hours and hours, on weeknights and weekends dressed as Andie, in dresses and skirts. And he loved it. He even started thinking of himself as Andie the woman. How cool was that?

Despite the difficulties, and the long hours of repetition and experimentation, he found that he enjoyed it all. Every aspect. And it kept him very horny.

With a week to go, he made one more rule for himself. No more whacking off until Andie's first night in the hotel. He wanted his libido on full alert and his balls blue with desire.

That rule was actually the worst, most torturous one to deal with. But he forced himself to comply.

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

Andy came home after his last day in the office excited and nervous. Was he really going to do this? It was such a big step!

But he had it all planed out, and his very hard cock told him that he absolutely had to go through with it.

He stripped off his work clothes and dumped them in the hamper.

From now on, I'm Andie.

The first thing she did was fill the bath tub with oils, suds and very hot water. Climbing in, she laid back, closed her eyes and dreamed happy dreams of the days to come.

After a while though, her hands drifted to her cock, and she only barely stopped herself from violating her rule against self-fulfillment. "Don't you dare violate any of the rules," she scolded herself.

Frustrated, but focused, she climbed out of the tub and took a look in the mirror? "Ready?" she asked the reflection in the mirror. She still looked like a guy, but that would soon change.

She laughed a happy response, but decided that she would take one more step before affecting that change. It was something that she'd debated about for months. But now, excited and feeling courageous, she pulled out a bottle of hair-removal cream and applied it all over.

Of course, she used a delicate version for her crotch and face, but everywhere else she used the regular strength stuff.

As expected, it burned, but she stuck with it and came out of the shower, with smooth and sexy skin, everywhere.

And when she slathered on a vanilla-scented body lotion, all over her silky-soft body, it felt wonderful!

After examining herself, she pulled on a pretty negligee, and moved into the kitchen to make herself dinner.

She hardly slept at all that night, and got up very early to affect her transformation.

Her first step was to cover her smooth body with a wonderful lotion that made her skin feel even more smooth and silky, and smelt delightful.

Then she hid away her cock in its tight little skin-toned gaff and covered it with a pretty pink lace and satin bikini panty.

Before sliding into the corset, she pulled sheer stockings up her smooth legs. They felt fantastic, better than ever. And she followed that by buckling the ankle straps of her tall and sexy spike heels. She'd been walking around, in her man clothes with her toenails painted in a bright pinkish red color for several days. Her strappy shoes showed them off beautifully.

Tightening her corset was difficult and painful, but eventually she got it closed. How will I ever be able to stand this? She asked herself, panting. But per the rules she'd set for herself, she knew she had to persevere.

When she measured her waist, she was delighted to see that she had, indeed reduced her middle to just twenty-seven inches. Unbelievable. She put on her bra with the large and heavy breast forms, before she checked herself in the mirror.

The view was impressively perfect. She thought her body was beautiful. Shapely, sexy and feminine. So alluring that it made her cock try to swell uncomfortably, down between her legs.

If only she could bend and breath. For a moment she considered loosening the thing, but she refused to break her vacation adventure rules.

She slid the corset's garters under her panties, and the gaff, before securing them to the tops of her stockings. A sexy lady didn't want to be bothered with them if she needed to gain access to her sex.

Next came the dress. It too fit her perfectly, showing off her shape. Tight at the waist, and across her breasts and the skirt was very short to show off her legs in their tall heels.

Again, an examination confirmed that at least from the neck down she was a sexy looking woman. There was no hint that there was a man's body hidden beneath the finery.

Now for her face. She'd been practicing with the makeup for so long now that she was sure she'd be just as successful with that aspect of her conversion.

As she worked her way through the process, just as she'd intended, she applied everything just a little heavier than her norm, going for an evening-out look, even though she'd be wearing it all day.

When she finished and ran her quality control check she acknowledged that she did look a bit overdone. Almost slutty. But once again the ache in her crotch confirmed that it was all good.

Finally, she brushed out her wig and fit it to her head. As it was one of the best money could buy, it looked beautiful and completed her look unbelievably well. She looked gorgeous.

When she stepped back and examined everything, she was truly pleased. She licked her sexy pinkish-red lips and said out load, "don't fool yourself, dearie. You look as good as you can, perhaps a six in comparison to a real girl." Or maybe a seven...

But that's good enough for me.

Her last step was to apply the fiddly nail extensions. As with everything else, she'd practiced the procedure many times over the past months, and had arrived at a passible skill level. It still took her a very long time to get them right, especially since she had applied the longest extension she'd ever worn.

She had expected it to be challenging, that's why she'd put that phase off until last. She certainly didn't want to damage the things while she was dressing, and she didn't want to have to deal with their cumbersomeness while she was applying her makeup.

At last, she was ready. And just in time, as dawn was starting to break and she had to be gone before her neighbors got up and out.

She quickly packed away her makeup and loaded her big suitcase into the trunk of her car.

Then she locked up the house, and hit the road.

A pretty woman on her way to the city for a week's vacation.

How cool is this?

But she only got a couple of blocks toward the freeway before she had to stop and painfully remove her heels. Too excited, she had forgotten to change into her moccasins, for the drive. She wasn't violating her rules, she had known that for the long drive, she could kill herself in her sexy heels.

She cursed as she found it almost impossible to twist and bend in her insane corset to undo the tiny buckles with her long nails. It took her forever! But at last, she succeeded, and settled in for the drive.

The corset remained uncomfortable for the first hour, but eventually her body seemed to get used to its restrictions and the drive passed with the only trouble coming from crappy drivers.

Andie focused on her driving as the miles ticked by. Anxious to get to her destination and careful to avoid any incident.

Two-thirds of the way along, she had to stop for gas, and dressed as she was, it was yet another challenge, although a small one. She figured she'd just quickly pump and go. No issues.

As she pulled up to the pump, she was feeling worried about being propositioned by some horny lecher hanging around the place. She wasn't up for that. Trying to prepare for that eventuality, she had whiled away the hours on the road, planning for how she'd handle a situation like that. How to tell a guy to get lost. She figured that every woman had similar routines for those situations.

Of course, she had to struggle to slip out of her flats and into her tall heels before she could step out to refuel. And the hours seated in her insanely tight and rigid corset left her stiff and pained when she stood up, tall in her sexy shoes.

And the thought of climbing back into the car seat, and removing her heels again was not something to look forward to.

But rules were rules. And suffering as she lived with them added to her excitement. She knew it was perverse, but it was also part of her kinky fantasies.

Glancing around the crowded station, she noticed several people staring at her. She tried to read their minds, to gauge their opinion, and was pleased that none of them seemed to be perturbed by the sight of her. In fact, a couple of them appeared fascinated - a men and a woman.

That was a relief and it sent a thrill down her spine, and made her cock swell.

Enjoying a deep breath and a short stretch, she stepped up to the pump, paid and began the fueling process.

She was waiting for her tank to fill, focusing on her task, ignoring everyone else, when she realized she had to pee. And that was an event she hadn't planned for. How could she have been so stupid?

She'd have to use the ladies' room, and probably be exposed to a room full of inquisitive women. Shit!

She'd never entered a women's rest room before. Never had to. But she had no choice; she'd have to take that chance, now.

After filling her tank, she walked carefully into the building and headed for the lady's room. It was weird just to pass the men's and use the other door.

It was another tense time for her. She had to focus on her walking as the tall heels remained a challenge. And it was only the second time she'd ever actually used a women's rest room.

Inside, she found several women at the sinks, washing their hands, and staring into the mirror. They all seemed to look at her critically as she walked past to find an empty stall.

Within the little cubicle, she stripped down her underthings and sat like a lady.

When she exited, with everything back in place, she stepped up to a sink next to another girl.

She glanced over, and snorted. "Awfully well dressed for the freeway."

Andie smiled sheepishly and mumbled, "I have a hot date when I get there."

The woman chuckled. "Well, he'll probably want to screw you on the spot."

Andie was surprised by the comment, it was something she was used to, amongst guys. But she didn't expect to hear it from a woman in the restroom.

Feeling devilish, though, she answered with a wry smile. "She will." And then walked out, feeling very good about herself.

Relieved in more ways than one, she made it back to her car, and after changing her shoes, drove away.

Back on the freeway, she breathed a huge sigh of relief and settled in for the rest of the trip. There was nothing that could stop her now. She hoped...

Eventually she started seeing the road signs that indicated she only had a dozen more miles to go. By then she was feeling both exhausted by the drive, and excited by the days ahead.

It had indeed been a long and tedious trip, and if it weren't for her excitement, she would have wound up frustrated and angry - so many shitty drivers on the roads.

She had been amused, when early on, as she cruised along, she realized that the truckers who passed, all got a good look down at her and that because of her short skirt, they were seeing a lot of leg, stocking tops and even quite possibly a flash of bare thigh.

At first, she was embarrassed, but after a few overly-friendly waves and a couple of honks from appreciate and lascivious truckers, she actually started to enjoy herself. It was a compliment, and she always laughed, wondering what they'd think if they found out her secret.

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

She finished the six-hour drive without incident and arrived in the big city just in time for lunch.

Navigating along the city streets was yet another nerve-wracking experience. The traffic was congested and moved fitfully from block to block, and traffic light to traffic light, so she had to drive slowly and carefully for a few more miles.

At last, she completed the battle through the downtown streets to the parking garage she had found in her research. She pulled in and felt herself lucky to find an open slot on the second floor of the huge structure.

She had booked a room in a small boutique hotel, in the heart of downtown. The location was perfect, but the place was small. It had a tiny bistro, but it didn't have a parking facility. The garage though, was only a few blocks away.

Still in her car, she changed shoes, finding that the previous practice had made it a bit easier. Her body was indeed becoming used to the corset.

Standing next to her car, she called the hotel, hoping that her room was ready, but of course, it wasn't. She was too early.

She had kind of expected that, so she grabbed her roller bag, wrapped her big purse around the thing's handle and began working her way down the sidewalk, past several shops, until she came to a nice restaurant where she could have lunch and while away some time.

The people there, again examined her, but none of them commented on her looks, her dress or pointed her out as a guy in drag.

Finished with her meal, and a nice glass of Chablis, she called the hotel again to see if the hotel was finally ready for her.

"Almost. In an hour." The desk manager told her.

Sighing, anxious to get into her room and freshen-up, she ordered another glass of wine.

Close to the appointed time, she paid and started out for the short walk to the hotel.

A block down, she stopped to peek into the display window of a shop, a woman's boutique that seemed to specialize in stylish and sexy clothes and lingerie. The more she looked, the more tempted she was to go in and check out the merchandise. What girl wouldn't?

And just then everything went to hell!

Fully focused on the pretty things behind the glass, and her fantasies of wearing them, she didn't even hear the panel van as it pulled up to the curb behind her.

When two guys opened the side door, and jumped out she noticed the reflection in the window, but by then it was too late.

One of them gave her a shove, while the other grabbed at her purse.

She yelped as she crashed into the glass. Luckily it didn't shatter, but in the process, she lost her grip on her suitcase handle and out of the corner of her eye she saw a guy pulling on the strap that she'd wrapped around the handle.

She was turning, and reaching out when the one who'd pushed her cursed, and yelled, "just grab the whole damn thing and let's get out of here!"

He gave her another push, and she again crashed into the glass behind her, before he grabbed his accomplice, hustled him with her suitcase in hand, with her purse still attached, throwing it into the open door of the van. The two of them then jumped in after it, and the door slammed shut as the vehicle sped away.

Stunned and hurting, Andie just stood there and watched as the bastards disappeared down the block.

When a woman came running out of the shop's door, cursing and asking if she was okay, she snapped out of it, and answered absently. "I'm okay, I guess. But those fuckers just stole all my things!"

And then it started to dawn on her how screwed she really was. Those thieves not only took her ID, her money, and her car keys. They also took her phone and all of her clothes, and she was now stuck in a strange city with absolutely nothing!

And she was a guy in drag!

Andie stood there stunned. Unable to think, unsure of what to do.

The woman from the shop, afraid that the girl in front of her had been hurt, or was at the very least in shock, grabbed her hand and led her into the store, all the while mumbling reassurances mixed with questions.

Andie just followed along, answering the best she could. She hadn't been hurt. Her name was Andie and she had just arrived in town.

She learned that the helpful and concerned store owner's name was Keira and she was almost a shocked as Andie was.

"I've never seen anything like that. I've heard of it happening, but not around here. I'm so very sorry." Keira said. She was clearly concerned and even embarrassed.

Andie, appreciating the support took a deep breath and dedicated a moment to examine her host.

Keira, was pretty, and a little older. Probably in her mid-thirties. She did have a shapely body and she was certainly well dressed. She ran a boutique, after all.

Andie was surprised by how attracted she was to the solicitous woman.

But then thoughts of her situation returned. What the hell am I going to do now?

"I need to do something." Andie mumbled, but she wasn't sure what.

"Of course, you do. You need to call the police, although I'm not sure what good that will do. They've been defunded and hardly ever show their faces around here. And you probably need to call about your credit cards." Keira said.

While Andie was still feeling stunned and unsure, Keira was all about taking action.

Keira, kindly, escorted her through the store, and into the back-office area, where she could use the store's land-line. The woman also cranked up a computer so she could use the browser to find the phone number's she needed to call - her bank, in particular.

All of the important numbers were in the lost phone, she couldn't remember any of them.

First Andie called the police to report the mugging. But that led nowhere. After hearing the details, they wouldn't even send anyone over. That was actually s small relief. She hadn't wanted to have to deal with the police, and admit that she was really a guy.

After that Keira left her alone to continue making calls in private. She had to go back to deal with her customers.

Alone in the office Andy called his bank and explained to the manager what had happened - mugged and his wallet and phone stolen. The guy was sympathetic, but careful. It took Andy a long time to convince the bureaucrat that he was, indeed himself, and then more time to get him to issue new credit and debit cards.

Andy then spent another hour dealing with the same challenges to get the DMV to issue him a replacement driver's license.

An hour later when she called the hotel, and made the mistake of informing them about her situation. They too were solicitous, but in the end, they explained that they couldn't allow her access to a room without ID and a valid credit card. Shit, shit, shit!

Keira had been in and out, while Andie spent her time on the phone. She had a store to run. But she happened to be present to overhear the call to the hotel.

"What are you going to do?" she asked.