Chapter 1

“Okay, we need to prove you can be trusted. No, no, that’s not it. We need to give you more incentive,” the older man with the gravelly voice said.

The frizzy-haired brunette looked confused as she took in his features, the greying goatee, the thick body, the trench coat he wore. With the confusion showing on her face, she glanced to the right and said, “Why would I need more incentive to comply?”

Leo glanced over his left shoulder to remind himself of what the twenty-year-old girl was seeing. The sun could be seen shining in through the window, but the lights were on full anyway. Just a few feet away from Leo was Ricky, similarly dressed in black and holding a silver baseball bat ready to strike.

What the baseball bat was ready to strike is what had Jill’s attention. Her eighteen-year-old younger brother was on his knees, his facial features not nearly as distinguishable under the blood and bruises that had already formed on his face.

The siblings shared a small three bedroom house that their parents had purchased for them for use in college. Their parents had decided to move right after Jill graduated, so Jill and Bobby had stayed in the town where she went to college and he finished high school.

The arrangement had worked out pretty good for them until Jill arrived home from classes to find two strange men in her house beating the shit out of Bobby. She had finally gotten them to relent enough so she could find out what was going on. Turns out Bobby had gotten into a gambling habit that she was unaware of, and owed a lot of money to some obviously nasty people.

She had pleaded to find out how it could be possible to repay them without them injuring her brother anymore than he already had been and was disappointed to learn that they accepted no trades on the cash borrowed, only the cash itself. Just when all hope was starting to seem lost to Jill, they informed her that the interest could be pre-paid. That’s when Jill made her mistake.

“I’ll do anything,” she had told them, realizing just a second too late what she had proposed. Both Leo and Ricky perked up at her offer. Before she could feel completely foolish about the offer the look on their faces told her that they were already going to demand her worst nightmares, but that she just quickened the process.

“Alright then, what’s your name sweetie?” the older man asked?

Jill remembered shaking when she answered, the way he called her sweetie. “Jill.”

The man had grinned at her, “I’m Leo, that’s Ricky. So you’re willing to pay your brother’s interest?”

It was her nod that had brought her to this point. Her nod that brought her to the question on why she would need more incentive. It was Ricky who finally answered her question though, bat still primed to resume its beating. “All these dumb cunts try weaseling out of it all the time. Most of the time it’s just girlfriends, and then we have to go find the guy again and really teach him a lesson, ya know? Maybe it’d be different you being his sister and all, but it’s still part of the job.”

Jill focused so much on what Ricky was saying that she hadn’t noticed that Leo had moved to a duffel bag that the men had apparently brought with them before returning with a smaller bag.

“Alright,” Leo barked. “Move to the table. Jeans and panties at your knees then bend over it.”

The look on Jill’s face at the order was one of shock, before the redness took over. She looked over at her brother once more, and Ricky brought the bat a little higher, as if preparing for a swing.

“If you’re worried about what we or your brother are going to see, don’t. It’s part of the price you have to pay and part of seeing how serious you are,” Leo said, slightly less forceful this time, but still with an authoritative air.

She sighed and turned around to head for the table. The look on Jill’s face betrayed a lot of emotion–shame, embarrassment, anger, and sadness primarily amongst them. Jill quickly undid her belt, then her jeans, lowering them down her legs, revealing the black panties she had worn that day. She hated the fact that she was giving these men, and her own brother, a look at her body.

Jill’s body was quite average, not too skinny, not too thick. She was basically your typical girl next door in the body department, and with that same cuteness to her face. Her hands reached into the waistband of the panties and slid them off enough until they fell to her ankles, then she bent over the table.

Leo came over and gave her ass a smack, eliciting a yelp from Jill. She didn’t have a big ass, but bent over it looked pretty good to Leo, and smacked pretty well to him as well. “Spread your ass Jill,” he commanded.

She took a deep breath, steeling herself up for it as she reached back with her hands and spread her ass, revealing all of her charms to the three men in the room with her.

“Would you look at that Bobby,” Ricky said as Jill’s heart fell into her stomach.

“I said look at it,” was spoken with much more authority by Ricky this time. “See, this is all your fault, the fact that we can see your sister’s cunt and asshole, and that we won’t be the only ones to see those today, that’s all because of you, so you might as well get what you asked for.”

Jill couldn’t be more mortified if she tried–she hated the idea of having to show her most intimate places to these men, least of all her own brother. She kept looking forward, not wanting to see the guys as they looked at her. Because of this she missed the black rubbery cylinder like device with a tube and a bulb on the other side that Leo had pulled out. She also missed the lube that was being spread around it, no clue that a custom inflatable butt plug was about to be put inside her ass.

It was only when she felt Leo’s lube covered finger touch her asshole that she realized what was about to go down. “Oh no, please, not my ass,” she thought to herself.

Jill was technically an anal virgin. While she had never had anal, and never been asked to, the last one night stand she had after a party was a guy who had stuck his thumb up her ass while they fucked doggy style. She didn’t like it then, and as his finger pushed inside she wasn’t liking it now.