By sticking the tube up her asshole

"Hey Jessica," Gordon sad with a wicked grin as he held the dollar bill out to her, "I'll give you a dollar if you stick that tube of lipstick up your ass for the rest of your shift."

Jessica blinked in shock at this request, "E-Excuse me?"

"You heard me," Gordon said to her, "You want my dollar, those are my terms."

Jessica frowned. This was insane, absolutely insane! She couldn't do that! She had hardly let anyone finger her before, there was no way she was going to...

Gordon wiggled the dollar in front of her face. Jessica gulped, then grabbed it out of his hand. Dammit, why did she have to love money so much? She stood up and started to make her way to the bathroom. Well, at least she would be able to get a nice settlement out of this when this was all...

Gregory pulled out another five dollar bill and said, "And I'll give you five dollars if you do it in front of us, and not mention this incident to HR or corporate."

Goddammit.

Jessica grabbed the five dollar bill out of his hand, then hiked up her skirt and turned around, pushing the back of her panties to the side so the two businessmen could see her crack.

"Damn, thanks for covering me there," Gordon said, "A gold digger like her probably would pull something like that. Why five dollars though?"

"It's the smallest bill I had in my wallet," Gregory replied with a shrug, "Now hush, you'll miss the show."

Jessica put the cap on her lipstick and looked at the black plastic tube in a brief moment of dread. Reminding herself that six dollars were on the line and she had already taken the money, she bent over and used the hand not holding the lipstick to spread her buttcheeks apart slightly, giving her easier access to her puckered asshole. She ran her tongue along the top of the lipstick tube to get it wet, then took a deep breath, reached behind her, and started to push it in.

"Holy shit, she's actually doing it," Gordon muttered, dumbfounded.

"Told you," Gregory said with a smirk.

Jessica winced as the tube of lipstick entered her rear exit. Thankfully it wasn't very big, so it was going in easily enough, but she was tight enough back there that it still stung a bit. She continued to push it in slowly until the majority of the tube was in her asshole, leaving only the very end sticking out so that she could pull it out later. This had the effect of making it almost look like she was wearing a small black buttplug to work. Without another word, she readjusted her panties to cover her butt again, then pulled her skirt back down and smoothed it out, completely hiding what she had just done.

Gordon whistled at the display, "Wow, I wasn't sure you'd actually do it. You wouldn't mind if I checked your ass again before you left today, would you? Just to be sure you aren't cheating me out of my money."

"I wouldn't dare do that," Jessica said to him honestly, "I always do what I'm paid to."

"Still, I want to make sure you are fully complying to our terms," Gordon countered, disdain evident in his voice, "If you don't, how will I know it really stayed up there all day? I have a hard time believing a gold digger like you would actually honor our agreement."

Jessica pursed her lips, offended at the comment. Sure she was a money-loving gold digger, but she took pride in the fact that she never cheated anyone out of their cash unfairly! Before she realized what she was doing, she said, "If you're really so skeptical, fine! Hell, I'll let you check any time you want today, just to prove I'm really keeping it in there!"

"Really? Thanks!" Gordon said, a big smile growing on his face. Jessica's face paled at what she just said, but taking it back now would make it seem like she was dishonest about her intentions. Right?

"Well, this was fun, but I should probably get back to work," Gregory said with a smile of his own.

"Yeah, me too," Gordon said, "Talk to you later Gregory. And Jessica, I'll be sure to drop by soon and see how you're holding up."

"Y-Yeah, bye," Jessica stammered, witching as the two men walked away. She went back to her desk and put the six dollars in her wallet, then sat back down in her chair. She squirmed in her seat, trying to ignore the feeling of the tube in her butt as she went back to work. She still couldn't believe she agreed to do something so... degrading to herself.

Don't think about it, Jessica, she told herself, It's a little embarrassing, sure, but it's worth it. You're making six whole dollars for doing this! That's... not a lot, sure, but it's something. Just hold out until the end of the day, and everything will be fine.