Leanna Ch. 02


The sensation was overwhelming. The hard cold wooden shaft ran over her naked body and down her back.

"Please, please, please, give it to me. God I want it so bad." The young woman cried out as the shaft circled her ass.

Just as the tip of the rod was pressed into her hole, she sat up in bed with a start.

The scene vanished and she was back in her bedroom. The dream faded away as it always did.

It had been several weeks since Leanna Price spent a night in jail after being arrested for underage drinking and drug use. She had tried to move on; doing everything she could to block the memory of the humiliation she was subjected to that night. She tried to continue her life, as usual, focusing on school and preparing for college next year.

She never spoke to her mother about the details of the ordeal. She was angry enough at Leanna for getting arrested. It could have jeopardized her college scholarship, and was an embarrassment to her personally, as she was a highly regarded lawyer. Leanna didn't dare complicate the issue further.

But despite her attempts to suppress it, Leanna still could not escape the feelings that had been awakened inside her. She knew she should feel horrified and degraded about what happened, but what really shamed her was that she came to realize she liked it. She frequently had dreams like the one she had this morning. It had Reenactments of her begging for more. A deep desire to succumb to the actions inflicted upon her.

Still, though, she did her best to ignore it. Today was an especially important day as it was her last day at Creekview Private High School. She and her friends had turned 18 some time ago, but they felt like only now would they truly be adults.

Leanna got dressed in her uniform like she always did. She was as sexy as ever with dark hair, big brown eyes, and an athletic body. Her style had changed slightly since the incident, however. She now dressed a little more conservatively than she had in the past. She kept her cleavage covered by buttoning up her shirt and wore her skirt a little lower. She also no longer wore a tie as she had lost hers and never bothered to replace it with school being so nearly over. Looking at herself in the mirror she couldn't help but be a bit relieved that this would be the last time she would have to put on her private school uniform.

She arrived at school late that morning, still distracted from the dream she just had. It was one of the most vivid yet. She had hoped they would pass but instead they seemed to be getting more intense as time went by.

"Just forget it," she thought to herself. "I don't enjoy that sort of thing, certainly not from another woman; it was just such an intense and new experience that I'm having trouble letting it go."

She had been trying to convince herself of this for days, but it was getting harder and harder avoid the fact that she was lying to herself. Deep down, she knew that she not only enjoyed being taken in the ass and humiliated, she actually craved for more.

Leanna distractedly opened her locker to put her books away, when she was suddenly jolted back to reality. Inside her locker hung the tie she had been missing. More importantly, there was a small piece of paper pinned to it with a short message.

"As soon as you can't stand it anymore, come find me."

Leanna was dumbfounded. She quickly looked around but the hall was empty. She instantly knew who this was from.

"How could she have found me? How did she even know what school I went to?"

As she asked these questions to herself the answer came almost at once. It was the tie. It dawned on her that she must have lost it at the jail cell. It had the school's emblem and name on it. Her locker was flimsy and old. It would have been easy to break into it and leave a surprise while no one was around.

A flood of memories crashed over her. She suddenly felt the way she did back in the cell. The feelings of helpless vulnerability, the fear of what might happen next at the hands of the large women in prison, these all returned with a vengeance. The emotions swirled in her head until she felt dizzy. Almost on cue, a startling noise came from the distance. It sounded like a hard piece of wood clanging against the floor. It was the same type of wood that was introduced to the inside of her ass back in the cell. The memory instinctively caused her to snap her legs together.

After a moment her anxiety subsided and she realized that the noise was just that of the janitor accidently dropping his mop as he exited a room. Coming to her senses she stuffed the tie and note into her bag and hurried off.

By the end of the day, Leanna started feeling better. Celebrating with her friends and enjoying the end of school festivities drove the unwanted memories from her mind. Rejuvenated, she walked home that afternoon and rationalized the situation. The note wasn't really a threat after all.

"And besides," she reasoned. "Just because she knew where I went to school doesn't mean she knows where I live. It's not as if I plan on going back to that school anytime soon. I should just relax, stop freaking out and forget about the whole thing."

Try as she might, the next few days didn't offer any relief. As summer sat in and the nights became warmer, Leanna's dreams intensified. She couldn't shake the desire. The feeling of being held down, the sensation of cold wood against her hot pussy and ass, the fear mixed with arousal. It was all becoming overwhelming. She found she was pleasuring herself nearly every night. Something she rarely used to do.

One hot night she was woken from the most intense dream yet. She couldn't take it anymore. Without fully thinking, she sprang out of bed and dug through her school bag finding the crumpled note.

"Ok," she quietly murmured. "But it's just curiosity, that's all."

Looking at the paper for a moment, she pondered the situation.

"How would I even know how to find you? Get myself arrested again? I can't imagine you'd still be there. Besides, I couldn't let anyone know I was doing this. My god, I can't believe I'm even thinking about this."

"Let's see," she considered. "I can't exactly just roam dark allies randomly asking people if they know a large Latina woman."

Just then it hit her. She and her friends used to buy weed from a dealer named Tino. He would usually hang around downtown behind a disgusting old bar. He was about the only connection she had with the seedier elements of society. If she was going to ask anyone about someone she met in prison, it would have to be him.

Leanna convinced herself that she would talk to him, but just to get information. She couldn't see any harm in that.

The next night Leanna snuck out and went looking for Tino. Not wanting to attract any attention she dressed as inconspicuously as possible. She wore baggy jeans, a T-shirt and a sweatshirt with a hoodie covering her face as much as it could.

It was a bit of a walk to get downtown, but she didn't dare take her mom's car to such a shady part of town. It wasn't so bad during the day when she usually ventured there, but she had heard all kinds of stories about what it was like after the sun went down. Supposedly there were muggers, prostitutes and all manner of drug users and dealers. Based on the people she saw as she hurried through the streets those stories didn't seem far off.

"What am I doing here? This is so dangerous. "

Despite her own warnings, she continued on.

"I just need some quick information then I'll go home." She reassured herself.

Eventually arriving at her destination, Leanna, sure enough, found Tino in an alley off the main street. He was talking to a man with a baseball hat pulled down low to cover his face. They exchanged something and the man slowly walked off. He caught a passing glimpse of Leanna as she crouched down behind a dumpster.

"Tino!" She called out in a loud whisper once the man had gone.

Stepping into view she lowered her hoodie so he could recognize her.

"Hey there Leanna," Tino said in a loud casual voice with no attempt at discretion.

"Shhh," she harshly admonished him. "I need to talk to you about something."

"Yeah, sure. Haven't seen any of you girls lately. Looking for a late night snack?"

He showed no interest in moderating his pitch.

"No, keep your voice down. I'm looking for some information on someone. A Latina woman."

"Gotta be way more specific than that baby face."

"You'd remember her if you saw her. She's big. Close to six feet tall, has a lot of tattoos."

Leanna searched her brain trying to think of more descriptions. Suddenly the name popped into her head.


Tino looked surprised.

"What about Rosa?" he asked in a slightly softer voice.

"I, uh, a friend said she met her once." she nervously lied.

"Really, a good girl like you has a friend who knows Rosa?" Tino asked skeptically.

Leanna just looked down sheepishly.

"I have cash."

The nervous woman pulled a wad of bills from her pocket

"Fine by me," Tino responded taking the money.

"If you really want to know, Rosa works nights around here. "

Leanna was taken aback.

"She's a hooker?"

"Popular one too from what I've seen. Doesn't even have a handler, just works for herself. In fact, she even has a few ladies working for her. A few guys too, I think. "

"So she's like a lady pimp but whore's herself out too?"

"Yeah, something like that I guess," Tino said as he counted the money. "Don't think she's around anymore, though. I hear the police picked her up a while back. She and a couple of her girls."

"Actually that's not true." A voice suddenly came from behind.

The man who Leanna had thought had just left stepped out from around the corner.

"She made a deal," he continued. "Did a little favor for one of the cops while she was locked up. Got released just the next day."

"What are you doing back?" Tino asked with some sign of annoyance at his sudden reappearance.

"Couldn't help but overhear the two of you. What did I hear your name was? Leanna?"

The girl just stood there not wanting to confirm her identity.

"We should have a chat." said the man.

"Go on Tino."

"Yeah whatever. You guys are scaring away business anyway."

Tino pocketed his money and rushed off.

"Rosa said you'd come looking for her eventually," the man spoke.

"Y-you know her?" Leanna asked, nervously.

"I work for her, yeah. We've all been keeping our eyes out for you. I'm surprised you came this quickly. She must have really given you a taste of something good."

Leanna blushed.

"I just wanted to find out..."

"Yeah, yeah," He interrupted. "The thing is, she wants to do more than talk."

Just then Leanna noticed another man approaching her from behind. Before she could react she felt a blow to her head and everything when black.

Her eyes slowly opened. Her head still soar she gently sat up to take stock of her surroundings. It was a dimly lit room with only a single light bulb on the ceiling. She was on a cot with a small bare mattress. As her eyes came into better focus she saw with more detail that the room was practically empty. The floors and walls were concrete and there was a large door that appeared to be bolted shut.

As her mind tried to come to terms with the situation she rested her hand on her aching forehead. It was then that she realized something else about her surroundings. She was wearing completely different clothes. Gone were her blue jeans and t-shirt. Instead, she was dressed in far less modest attire. This was nothing like anything she would wear on her own accord. Her legs were bare except for a pair of tightly laced, leather knee-high boots. Her arms were adorned with long black gloves. Two large metal bracelets clung to her wrists. Black silk panties barely covered her lower privates while a strapless leather corset was firmly fastened around her chest and torso. Her breasts nearly spilled out over the top as they were squeezed by the garment. She also felt a collar fastened around her neck.

"This can't really be happening," Leanna thought to herself as reality set in. "I'm in some kind of dungeon! I knew it was a mistake to go downtown at night."

Her head was starting to feel a little better now, and she stood up. The first thing she did was try the door. It was sealed shut as she had feared. Not sure what to do next she looked around. There was cool air coming from what appeared to be a small vent above the door. Shivering a bit in the small amount of clothing she was wearing, the frightened girl crossed her arms and stood helplessly trying to figure out her next move.

As she scanned the room, an old dirty mirror on the wall caught her eye. It was so covered with dirt and dust she could barely see into it. Vigorously wiping a spot clean with the palm of her hand she was shocked by what she saw in the reflection. Her long brown hair was pulled tightly back and tied in a bun. She had on heavy black mascara and lipstick.

"I can't believe this," she thought to herself. "What is happening? How long have I been here? What's going to happen?" Questions swirled in her mind.

After a moment, resigned to the situation, Leanna went back and sat on the bed. With her back to the wall, she pulled her legs up to her chest and wrapped her arms around them trying to fend off the chill air. She may not be dressed like it, but inside she felt just like that scared school girl back in the jail.

After several minutes a noise came from the door. It was the clanging sound of the metal bolt being unlocked. The heavy door creaked open and a large muscular man entered. Leanna quickly got to her feet.

As he advanced she took a frightened step back. The man held a long metal chain with a clip at one end. Frozen in fear the terrified girl stood still as he grabbed her collar and attached the chain to it.

"W-what's happening?" Leanna nervously asked.

Without saying a word the man walked out the door. With a strong pull, Leanna was yanked forward forcing her to stumble after him.

She was led through a dark hallway and up a short flight of stairs to another metal door. It opened revealing a slightly more brightly lit room which made Leanna wince at the sudden change in illumination. Looking at the man as if for some sort of instructions on how to proceed, he simply stood firm like a statue.

"Well don't just stand there," a familiar voice suddenly spoke. "Come in and let me take a look at you."

Leanna caught her breath at the sight of the woman sitting on a large throne.

"I know my little princess hasn't forgotten Rosa."

The sight of the woman who had shattered her world only a few weeks ago sent a chill down Leanna's spine. Just the reminder of what she had done to her in that prison cell, the sensations she had introduced her to, filled her with fear. At the same time, there was also a creeping sense of anticipation.

"Sorry for knocking you out, but we can't have people knowing the location of my little sanctum here."

"What exactly is this place?" Leanna thought to herself.

As if reading her mind Rosa explained. "This is sort of my secret hideout. Sometimes I bring clients here, but a lot of the time I just keep it for my own little activities I like to indulge in. I thought it would be a good place for the two of us to get together. Nice, isn't it?"

Leanna said nothing.

"Anyway, we both know why you're here, don't we?"

Again, Leanna just stood silently.

"Well let me just make sure we're both on the same page. About a month ago I gave you something you didn't know you wanted. And now that I so generously gave you a taste, which you didn't thank me for by the way, you had to come find me to beg for more. Just like a little slut."

Embarrassed Leanna just stared down at her feet. She hated to admit it, but that was a fairly accurate assessment.

"Now here's the thing, it would be no big deal to me to oblige you, but what would be my reason for doing so? I know you had a couple hundred dollars with you, and it's mine now, but I'm going to need you to do some work as well. Why do you think I dressed you so nicely?"

"Ok, just please don't hurt me." Leanna softly begged, slowly acquiescing to the circumstances.

"Oh I'm definitely going to hurt you, and you're going to beg me to keep hurting you, but like I said, you're going to earn it first."

"Let me introduce you to two of my top men. You met Daryl earlier tonight."

Rosa motioned towards a man standing in the corner that Leanna recognized as the person she was speaking to in the ally.

"And the guy with the chain is Ty. He was responsible for that unfortunate headache I'm sure you're feeling. They're my loyal assistants and I always like to give all my employees a treat now and then. It's been a while, hasn't it boys?"

Daryl smiled and Ty just gave a solemn nod.

"I bet they'd love for a pretty thing like you to give them a little pleasure. So before I deal with you, you'll have to deal with them."

Realizing that she couldn't back out now even if she wanted to, Leanna surrendered to the fact that she would have to obey Rosa's orders.

"You ever give head before?" Rosa asked.

Leanna shook her head.

"I don't believe you," Rosa said with a sleigh smile. "Regardless, now's as good a time as any."

Ty stepped in front of the cowering girl and pointed to the ground indicating for her to take her position.

Kneeling down on the cold hard floor Leanna meekly looked up at the hulking man. Her eyes widened as he unzipped his pants and revealed the largest penis she had ever seen. It was long and looked practically as thick as her wrists.

"Oh my god, I can't believe I'm doing this." Leanna thought to herself.

She parted her lips as the man slowly slid his cock into her mouth. She instinctively winced at the first taste of the veined appendage. Grabbing the hair behind her head he pushed into her throat hard, then began to move back and forth. Gagging a bit at first, Leanna put her hands around the shaft and started bobbing back and forth in unison with his pushes. The bracelets around her wrists chimed with the jerking motions.

After a few moments, Daryl came over and took one hand. With her lips still around the first man, he placed her hand on his own exposed cock. She stroked it until it became as hard as the first. Withdrawing she turned her head to allow the new man to enter her waiting mouth. One hand remained stroking Ty while she gave attention to the new shaft between her lips.

Again after a moment, she turned to the first cock while still stroking the other. Back and forth she alternated between the two men. As the rhythm went faster and faster she, found herself starting to become aroused, even getting a bit wet down below. Eventually, a warm substance shot inside her mouth. Trying at first to pull free, her head was held firmly in place giving her no option but to let the cum fill the back of her throat until she was forced to swallow.

Feeling the dick soften, her head was released and she turned to the other cock. After a brief moment, it too sprayed. This time her head was quickly pulled back allowing cum to be released all over her pretty face. The fluid ran off her chin down to the exposed top of her breasts and on down to her bare thighs.

The two men pulled Leanna to her feet.

"That was fun to watch," Said Rosa as she casually got up from her throne and stood imposingly in front of her.

"I know my men enjoyed it."

Rosa gently lifted Leanna's chin so that she could look her in the eyes. After examining her briefly the towering woman gave a long lick to the side of the smaller girl's squirming face, lapping up some of the remaining cum.

"Mmm, you're as tasty as ever."

The powerful woman took the chain around her prisoner's neck and led her across the room. Leanna tried to whip off her face with her hands as she followed.

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