She takes it

"Ok. I'll do it." Tilly says.

"Excellent. I'm sending a car for you now. Wear a dress. No panties. I'll text you more details on your way." Luna hung up before Tilly could say anything. Tilly gulped, she was really doing this.

She ran to her bedroom but in her haste she dropped the key, "Shit." She scrambled to pick it back up. Her hands were shaking as she tried to unlock the cuffs. Finally she got it and took them off then darted into the bedroom. She grabbed one of her more modest dresses and tried to put it on, but her body wouldn't let her. "Shit...Master...may I put on this dress? It's for a job."

The Taskmaster replied, "No. That dress is not appropriate for this job."

Tilly groaned and tossed it aside. She picked out another dress. This one was significantly shorter and showed off way too much cleavage, "Master may I wear this one?"

"Yes."

Thank God. She quickly got dressed and ran to the bathroom to fix her hair and makeup. As soon as she was done she slid into some heels and hurried for the elevator. Her phone dinged just as she made it to the lobby, it was Luna with more instructions. Before Tilly could read them she saw the cab pull up so she hurried inside. Only once the cab was away did she have the chance to read it over.

When she arrived she was supposed to pretend she was interested in buying the place. There was a lockbox out front and Luna provided a code. After letting herself in she was to wander around, making comments about the place. Until she reached the office on the second floor. That's where it was to happen.

The taxi arrived and she found the lockbox without any issue. Just from the outside she could tell this was about to be the nicest home she'd ever been inside. It was huge, truly a mansion. She didn't have to fake her excitement as she started wandering around, although she did have to **** herself to vocalize her thoughts. Luna had told her to take her time, and to remember she was being watched. She never saw any cameras, but she made a point not to look for them too.

Finally though she made it to the office. She walked around a bit before stopping in front of the computer. Now it was time for her to turn on her acting skills, such as they were. She pretended to be curious, she shook the mouse. The screensaver disappeared to reveal porn. Not just any porn, Tilly found herself staring at a woman that looked just like her. She squealed and turned away, taking a few steps towards the exit. Then she stopped. She was supposed to pretend to be intrigued. Slowly she went back to the computer and took a closer look. Upon reexamination she could tell the actress wasn't exactly like her, but the similarities were striking. That must be what Luna meant when she said she couldn't do it herself.

Tilly gulped and sat down in the chair. The video was paused and she hit play. She watched the entire video, pretending to be enraptured by it. Then she restarted it and started rubbing her breast as she watched. Slowly she slid one hand down her body and under her dress. Her dress was short enough she barely had to hike it at all before she was stroking herself. She closed her eyes and pretended this wasn't just about the weirdest thing she'd done. She didn't masturbate often, well not anymore anyway. Oh no, would she even be able to? Would she have to fake it?

As she felt herself getting closer and closer she got more and more stressed. What if the client didn't believe her fake moans? Would she still get paid? The stress turned to frustration and she felt herself reach her peak...and fail to crash over it. She moaned, partly in lust, partly in frustration. She didn't care about the job anymore, she needed to cum. She decided to beg for it, "Master...may I cum?" She whispered.

There was no audible response from the app but she felt it like a dam breaking. She screamed loudly as she came. As she came down from the sigh she swore she heard the sound of a man's moan. She ignored it and stood up, a little embarrassed by her showing. She straightened her dress and hurried downstairs.

She decided to save herself the taxi home and to just walk. Good exercise would make the app happy and she now found heels to be quite comfortable. She was about halfway home when she got a message from Luna.

The client was thrilled apparently. Not only had she earned the money, he'd tipped her generously. Can you believe it, $1500 just for touching herself in a fabulous mansion. Tilly felt a little gross about that but decided the money more than made up for it.

As she walked she pulled up the taskmaster app and saw a notification.

Daily Quest #1 Earn at least $100 Complete - Reward Increased likelihood of additional jobs in same line of work

Daily Quest #5 Go Above and Beyond on any other quest Complete (Earned 15x Quest #1) - Reward Receive only 3 daily quests tomorrow

Tilly went fought to keep her mouth shut. She wanted to complain to Taskmaster. It seemed to know what she was thinking anyway, but only ever punished her for speaking it aloud. A reward? Increase chance of additional what, sex work? How is that a reward?

The second reward...she supposed it meant tomorrow would be easier...but still felt like a disappointment. Oh well...no use complaining. She still had one more quest to finish, this mystery date. The date that she knew absolutely nothing about. Maybe she'd earned a little goodwill with the app.

"Taskmaster...Master," She began, "Can you tell me about my date tonight?"

"Yes." Taskmaster replied.

Tilly waited but Taskmaster said nothing else. Tilly tried her best to keep her tone polite, "Who am I meeting? Where? When? What is this person like?"

"Your date's name is Sam. You are meeting at Urban Impressions Galley, 45 Main Street at 6pm. Sam has many characteristics which have been identified as compatible with you." Taskmaster said.

Tilly sighed, that didn't really help. She checked the time, she had enough to get home and take her time getting ready. She'd take a taxi there to avoid being sweaty for her date. She knew Taskmaster would expect that. At least she had some funds now. This job had given her enough to have a little safety net.

After arriving home she spent her time getting ready. Another shower, she made sure to shave while she was in there. She did her hair and makeup, put on a very sexy dress. Again it was way more than she was used to revealing but since her body was so fit now she was a little bit less self conscious about showing it off. She put on some black heels to go with it and went downstairs to catch her taxi.

On the way there she looked up the Gallery. The first thing she noticed was the hours of operation...8-5. So it was closed? That didn't make any sense. Her phone buzzed soon after. She didn't recognize the number but they were already in her phone as Sam Johnson. Hey looking forward to tonight. The sign says closed but I left the door unlocked so just come on in when you get here.

Tilly sighed, she was going to be alone with some guy all night? This was sounding sketchy. She hoped it wasn't a repeat of Alex. Taskmaster had assured her she was never in danger but that did little to reassure her. Well, she knew she couldn't back out now. Not without a punishment. She replied, On my way now, 10 minutes.

Soon the taxi arrived. She paid and stepped out and looked at the gallery entrance. She'd never been here, she wasn't really the target demographic for buying fine art after all. It just seemed too fancy for her. She looked down at herself, well at least she looked the part. The app might have done lots of bad things to her, but the replacement wardrobe she'd been given was all high end clothes despite their skimpy coverage.

Ok, here goes, Tilly thought. She walked towards the door and pulled it open. Inside was a large open space with a small reception desk. Art covered the walls. Some small pieces while others were massive. She looked around in awe for a moment, it was gorgeous. One piece in particular attracted her attention and she found herself walking towards it. She was so engrossed that she failed to notice the sound of footsteps approaching.

"That's one of my favorites too," A voice said behind her. Tilly jumped and spun around, "It really makes me feel calm whenever I stare at it. Local artist, extremely talented."

Tilly stared, this was her date? "Uh ya, it's beautiful." Tilly managed to say.

"And so are you, wow, that dress! It's so nice to meet you in person, I'm Sam." Sam was not at all who Tilly expected. It turns out that Sam is not short for Samuel...but rather Samantha. Taskmaster had set her up with a woman. She had short hair dyed pink and blue and wore a pantsuit. She was attractive sure, but she was a woman...why had Taskmaster set her up with her...because she'd had a bad experience with a man? That was a pretty poor reason.

Tilly did her best to hide her surprise, obviously Sam expected Tilly to be interested in women, the app had been flirting on her behalf. The app would also certainly punish her if she just ran away from this. Tilly offered her hand, "Nice to meet you too. Tilly."

"How about I give you the guided tour? If you like this piece I have some that will really blow your mind. Come with me." Sam said cheerfully. Tilly nodded and started walking along side her.