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Rated: 18+ · Interactive · Entertainment · #2303881
A teenage guy's curiosity leads to crossdressing, identity theft, and other nonsense!
This choice: Scenario A  •  Go Back...
Chapter #3

Idle hands are the Devils’ workshop

    by: Kirafair Author IconMail Icon
Harry Smith lay on his bed propped up by a couple pillows while playing a mobile game on his phone. Genshin Impact might not be a very difficult game to master yet it had several redeeming features. For one, the graphical design of the characters were pretty cool to look at. But most important of all, it was free to play.

The sound of a door opening downstairs alerted him that he was no longer home alone. Since his father was away working on an construction project on the other side of the country, his two older sisters were off doing college stuff, his younger sister Andrea was at softball practice, this left only one probable choice. His assumption was confirmed when his Mother shouted loudly

“Harry, can you help me unload the groceries?”

Harry grimaced unhappily. He had just begun a boss fight and it normally took a few minutes to finish. Time his Mother would undoubtedly criticize as not being productive. Harry was in no mood for an argument about how he spent his free time. With a sigh, he shut the app down and headed downstairs. He silently made several trips from the car to the kitchen with double handfuls of bags without seeking to engage his Mom in conversation. Any hope he might be spared from her persistent questions soon vanished.

“What finals did you have today?” she asked while preparing dinner. Harry slumped into a seat at the dining table.

“Just one” he muttered unsuccessfully suppressing the surly tone in his voice “English. Went pretty well I think” he added with a shrug.

Harry was nearing the end of his 11th grade academic year of High School. His school was in Finals week where the student’s day was split into morning or afternoon periods for a specific exam.

His Mother Linda ignored his attitude and carried on “That’s good to hear. So what finals do you have left?”

“Math is my last one tomorrow morning” he said hoping she wouldn’t jump to a subject she had been harping about for a weeks now. He was quickly disappointed

“Okay then. Have you had any luck finding a job for the summer?”

Harry rolled his eyes “Not yet.” Of course his chances of finding said job would go up drastically if he actually made a real effort at finding one. Harry would vastly prefer to just chill out all summer playing games or hanging around with his friends. His parents both worked earning decent money and he had few needs so getting a dumb job for 3 months seemed a massive waste of time.

Linda Smith’s eyes narrowed suspiciously “Oh really? Andrea already has a job lined up babysitting. Sharon is helping with a medical mission in Africa and Hailey is doing a summer research project at the University. Do you plan on playing silly games on your phone until school starts in the Fall?” she said acidly.

Harry bit back a reply and turned away to stare out a nearby window. His parents were always comparing him to his three sisters with him always coming out on the short end. Maybe it would be better to find some menial job just so he wouldn’t have to hear about it for the next few months.

*****
The next day Harry entered the empty Smith household and bounded upstairs to his bedroom. He felt a desire to plop down on the bed and play Genshin but he managed to summon up enough energy to initiate a job search. Still quite annoyed he was forced to do this, Harry made his way to the study and booted up the computer.

Several hours later, his head hung low totally defeated. Harry was regretting his procrastination as his online search efforts had come to naught. Of the employment listings he found, he was either not qualified for or he really didn’t want to do it. Slaving away in the hot sun all day on a landscaping crew sounded like a horrible idea.

If he had bothered to obtain a Lifeguard certification, there were jobs aplenty. That would have been a cool job But in retrospect, maybe not. Harry wasn’t a particularly athletic boy with a slim build and short stature. He could see people at the pool wondering if he needed saving whenever he entered the water.

Harry leaned back in the chair and stared at the monitor. Ironically, either of his older sisters could land a job waitressing in a hot second based on the large number of postings. In fact, there were at least three restaurants within walking distance of his house. Then a very unexpected idea popped into his head.

Growing up as the only boy in the house, Harry occasionally was the victim of teasing or a prank by his sisters. Usually involving them cajoling him into wearing their clothes. Or they physically forced him. Harry usually complained loudly but in truth he liked it. In many ways he envied them. Whether this directly lead to his interest in crossdressing would never be known. As Harry entered his teenage years, his desire to wear their clothes waxed and waned. Both Sharon and Hailey were very conscious of the latest trends and had the cutest clothes. While Andrea was 2 years younger and less into girls fashion, she was tall for her age. Harry immediately recalled how well her gymnastics leotards fit him when he tried them on last year.

A devious smile creased his lips “I couldn’t really do this could I?” he muttered aloud. This kicked his cross dressing desires into overgear. He had only a few hours before his Mom would get home to test his idea.

With abandon, he ran into Sharon’s bedroom. Since she was out of the country and wasn’t expected back until Christmas, she would never notice her things were moved around. He quickly stripped and put on a bra and panty set. Stuffing the cups with some pantyhose, he pushed the bra cups into a shape he was satisfied with.

As he was going through Sharon’s vanity table, he found an item that sent his heart beating faster. She had left her driver’s license behind. Obviously she had no need for it in Africa. He studied the wallet sized card for a moment. If this was going to work, he would need to look reasonably like the photo on the front. With his goal established, Harry got to work putting on makeup. Due to his sister’s years of teasing, he was fairly experienced with what needed to be done. Harry had even sneaked into their rooms a few times to practice on his own.

Thirty minutes later he was quite proud of his efforts. The only problem was his hairstyle. It was due for a trim but it was not very long nor very feminine. Harry was beginning to think his hare-brained scheme was about to fall apart when he remembered Hailey had worn hair extensions for a time. All the Smith children had dark brown hair so he was sure they could help him if he could find them. A thorough search of Hailey’s bedroom was successful. It took him awhile to figure out how to clip the extensions in but his mouth dropped open when he saw the result. He looked very much like one of his sisters. Harry tilted his head side to side trying to decide which one.

I think I see a bit of all of them in my face’ he pondered.

After a few moments of enjoying his handiwork, he forgot back to work. Now was the time for the fun part. Harry could barely contain his excitement. To date, he had never put this much effort into cross-dressing. Possibly for fear of being caught but that seemed less of an issue at the moment. He proceeded to raid Sharon’s and Haileys closets. He had more success with Hailey’s shoes but Sharon had a greater number of cute outfits. He settled on a pair of Black ankle boots, a short denim skirt, and a Red sleeveless blouse.

Harry was overtaken not only with the thrill of wearing their clothes but the idea of using Sharon’s identity. He posed in front of a mirror admiring his image.

“Hello, I’m Sharon Smith. I’m applying for the waitress job. I’m 22 years old and about to start Medical School in the Fall. No, I’m not experienced but I’m very willing to learn” he smiled while speaking in a soprano.

He wasn’t sure yet if he could pull this off. But the very idea he was considering it caused his dick to get hard from excitement.

“Fuck it. If Mom finds out, I can always say this was the only job I could find” he muttered.

After retrieving Sharon’s ID, he minced back to the study and uploaded a scan of the license to the job board. After typing in the necessary biographical information, he sent an application for “Sharon Smith” to the three nearby restaurants.

The first was an old fashioned diner. Harry observed the staff wore a short sleeved red dress with Checkered accents.

https://pin.it/1OnufBxGm

The next restaurant was a popular sports bar. Owing to its theme, the staff wore a short dress akin to a cheerleader uniform

https://www.restaurantmagazine.com/wp-co...

Harry believed that Hailey had worked there for a summer a few years back. He didn’t recall her describing that experience fondly.

The third place was an upscale streak house. The waitresses wore a White tuxedo shirt with a Black bow tie and skirt.

https://i.pinimg.com/736x/1d/1b/48/1d1b4...

*****
That night during dinner, his Mom quizzed him about school and his job search. Harry somewhat truthfully told her that he applied to a bunch of places including “any job they had open at a couple nearby restaurants”

Linda Smith happily accepted his statement at face value. “I’m glad to see your keeping all options open. Its better than wasting your time all summer doing nothing and this way you will gain some valuable experience”

Harry wiped his mouth with a napkin “Oh I certainly hope it works out” he agreed readily

Which restaurant requests “Sharon” to stop by for an interview first?

You have the following choices:

*Noteb*
1. The Diner

*Noteb*
2. The Sports Bar

*Noteb*
3. The Steak House / or something else happens

*Noteb* indicates the next chapter needs to be written.
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