Paying Brother's Debt
Chapter 1

Caution: This Erotica Sex Story contains strong sexual content, including Coercion, NonConsensual, Fiction, Crime, BDSM, MaleDom, Humiliation, Rough, Sadistic, Spanking, Torture, Gang Bang, Group Sex, Anal Sex, Sex Toys,

Desc: Erotica Sex Story: Chapter 1 - Bobby got himself indebted to the wrong people--to keep her little brother from being maimed, or worse killed, Jill submits herself to use and abuse

“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.

The exposed girl whimpered as Leo sawed a finger inside her ass. “Fuck you’re tight,” Leo said almost gleefully. He only fingered her ass for a minute before pulling out and replacing it with the butt plug.

“Take a deep breath sweetie, and try and relax.”

Jill tried her best to follow his advice, but of course it’s one of those things that’s a lot easier said than done. Her breathing quickened when the plug started opening up her tightest hole, and even though the whole process of getting it embedded deep within her ass took less than a minute, for the brunette it felt like an eternity.

She was even more confused as she heard squeezing that sounded not unlike a blood pressure cuff being filled. It only took a few seconds before she started feeling the plug inside her spread itself out, inflating inside her bowels. The discomfort kept on increasing for her, her breathing erratic as she tried to deal with the feeling of it expanding, until finally she yet out a yowl as it was becoming too much.

That’s when Leo stopped.

“Good girl. Most of you bitches just try and hold out, I stop when you finally give up and show me that you’re not liking it, that’s how I know it’s time.”

She couldn’t tell what was happening behind her as Leo was playing with the plug in her ass. Even if Jill had known what an inflatable butt plug was before this day, she wouldn’t have understood how this one was a custom job, with a custom deflator valve that could only be opened with a small key. Leo finished pulling the tube off and moved his hands up underneath her, above her pussy to feel her pubic region. When he felt hair there he withdrew his hand.

“Alright sweetie, here’s the deal. I’m guessing by how you reacted you’ve never had a plug in your ass before. That one is inflatable and is now much larger than when it went in. It’s not impossible to get it out, but it would probably take you a while and be rather painful. Read the instructions on the paper and it will be removed and you’ll pay back your brother’s interest.”

When Leo was done talking he set the piece of paper on the table and gave her ass another smack, causing Jill to yelp louder than before. Ricky too came over and smacked her other cheek on the way out, and she saw both men exit through the back and they left the house.

Jill wanted to get up, and started to do so, but quickly fell to the table. The intrusion in her ass was softening from the sharp pain as he inflated to a very uncomfortable presence, but her movements caused the cruel device to shift, and she had to learn to adjust with it. More ready to take it slow, she started sliding herself back off the table, her arms reaching down to her panties and pants so she could pull them back on.

She went slow–perhaps a lot slower than she had to, but she did it just so she could adjust, and after a few minutes she was finally standing again. She turned to see her brother sitting on the ground, hurting, and still bleeding from a few cuts on her face. Very gingerly Jill made her way to the kitchen sink, wetted a towel with warm water, and made her way over to her brother.

Bending down very slowly she started to apply the towel to his face to clean him up and he started to come around again, apparently having faded for a moment from his own pain.

“I’m so sorry Jill, I never meant for you to...”

“Shhh,” she told him. “I know you didn’t, and we’re gonna have a talk about this.”

“What are you going to do?” he asked as he grabbed the towel and started wiping his own face more.

Jill sighed before replying. “I guess I’m gonna do what the note tells me to. Let’s face it, I’m probably getting fucked tonight.”

Bobby looked upset, or at least Jill thought he did–it was hard to tell with how his face was swollen up.

“We’ll deal with it later, are you going to be okay physically?”

Bobby waved her off. He felt like shit of course, but moreso from the pain of what his sister would probably have to go through for him rather than the physical pain he was in (which was also quite considerable).

Knowing there was no point talking about it with either of their conditions, Jill eased herself back up into standing and returned to the table, picking up the list and looking at it. The more she read it the more she frowned. “Sounds like I’m going to be returned early,” she said. “I’ll need you to keep the front door unlocked for when I get home.”

Without waiting for Bobby’s response she went to her room to change and grab her purse and keys. She had two tasks that she needed to complete before tonight, and figured she should go out first so she could try to relax and calm the nerves before the big event.

Jill quickly peeled off her shirt and bra, but was more slow with the rest of her clothing. She looked at her naked body in the mirror like she hadn’t before. Her small b-cup breasts, the tuft of hair right above her pussy, and she turned around to see the end of the plug spreading her cheeks, easily visible. She knew she was cute, and she never had problems getting guys even though her body type was pretty average. She just knew more people would most likely see it today than ever before, and that made her a little self conscious.

Going to her closet she picked out a yellow flowery sundress she owned. Not something she would ever pick out for herself–it had been a gift. She raised it over her head and let it slide down to cover her body. The dress was like she remembered it, way too flowy, and girly for her. But the instructions said something like it should be worn.

She found flip flops and grabbing her keys, phone, and purse she headed out toward the garage. Bobby was still sitting in the kitchen shaking his head and stressing over the events of the day so far.

“By the way,” Jill said in a very businesslike tone, “I’m going to need you to move your car from the garage while I’m gone.”

With that she was out the door.

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