A Darkening Soul Ch. 08-13

Chapter 11: An Asshole Gets What He Deserves

One week before spring break, I was going over plans for Emma, Hilary, and I. We were spending the week at Hilary's house. Why spend the money to go to Fort Lauderdale or Cancun when you know you aren't going to step a foot outside?

"Boss, I got a proposal for Lindsey I think you'll want to consider." Lucy was excited about this one.

"What is it?" I didn't raise my eyes from my laptop.

"Brantley Sherwood wants to know how much for the entire spring break." Lucy announced.

"Really?" That statement got my attention. Brantley has the biggest ego of the school. He didn't appear cruel about it, but he did seem to expect everyone to fall to their knees if he passed by. And I know Brantley is loaded, but even he should know 10 days and nights is going to cost him a nice chunk of his inheritance. "$10,000 up front. And if they go anywhere, he is expected to pay for everything, airplane ticket, hotel, food, and everything else."

Two days later, I was in awe as Lucy counted out ten grand. It wasn't the money, but the fact Brantley had that much money at one time. I had Edwin and Stu come with me to make my deposit to the bank.

Spring break came and I for one had a blast. I can also vouch for Emma and Hilary as well. In ten days, we explored all possible combinations three people could have sex, I was hanging from a ceiling fan at one point. All of which resulted in my balls now being the size of peanuts. Heading home Sunday afternoon was especially painful. It took 20 minutes for my eyes to adjust to actual sunlight.

It seemed every student was in high spirits and maybe a little hung over. As I flowed through the sea of people, I heard all sorts of conversations about what everyone did. Almost all was embarrassing. Why tell someone your shame? I laughed with some and merely acknowledged others with a hello until I saw Lindsey. She had several bruises on her arm and a black eye, and that was just what I could see.

Lindsey was turning from her locker and I embraced her. "Tell me everything that fucking asshole did to you."

After her recount of her tale of abuse, I responded. "I love you Lindsey." I didn't call her whore but I did lie. She really needed to hear those four words exactly.

Lindsey had a horrible spring break. Horrible isn't even the word. I texted Emma, Lucy, Shelby, Edwin, and Stu for a meeting in 3rd period. I had Emma get Brantley's class schedule and hall passes for everyone for 6th period from Principal Larsen. I ordered Edwin and Stu to go with Lucy to forcefully grab Brantley and bring him to the football field right before school let out. Everyone was to spread the word that if any student had any ill will toward Brantley Sherwood, which was anyone that met him, to come to the football field after school. Fuck, I was pissed.

As the crowd filtered into the bleachers, Brantley was already tied to our gymnastics team's pommel horse at the fifty yard line.

"Welcome fellow Hilldale High School students." Lucy had the microphone and was in fine form. "We are gathered here on this glorious Monday afternoon to witness, and yes, even participate in the demise of one Brantley Dick, I mean Richard Sherwood." The crowd roared at the use of the nickname. "Look at what this slime did to one of our classmates!" Lucy made a hand gesture to Lindsey. "Despicable! Irreprehensible! And totally unforgivable! Anyone who agrees with me or anyone who just don't like Dick here, line up behind poor Lindsey." Lucy walked over to Brantley and turned off the microphone. "My boss says that you damaged his property so now we get to damage you." Lucy turned the microphone back on and turned to the now long line. "Step right up and grab your ammunition. Take as many eggs as you want. Plenty for everyone."

Shelby and Lindsey went to every store that sold eggs in a five mile radius and bought them out. They arrived right as the final bell for school rang and Stu and Edwin were still unloading them as Lindsey grabbed one and hurled it toward Brantley. She wasn't done. She let out ten days' worth of frustration, unloading egg after egg after egg in Brantley's face and body at point blank range. Three dozen eggs before her tears took over as she was mentally reliving her anguish. She followed all that up by walking up and kicking him right in the testicles. Go Lindsey.

The line was long. Apparently he liked to hit all his old girlfriends. What a major Asshole. The surprise to me was the line even consisted of two female teachers, Mrs. Jones and Miss Anders. It appears that Brantley was relentlessly annoying in his bids for them to consider going out with a student. He should've done what I did. Brantley's face and body had a multitude of cuts and bruises and it was evident swelling was already beginning to form. But his crotch is what took the biggest beating. It was almost as if it was open season and every one was hunting for his one eyed trouser snake. I smiled and left as the fiasco was coming to a close. Nothing like a good flogging to get a person in the mood to fuck their fiancé.

Chapter 12: Okay, So I Can Be Bribed

I rarely go to class anymore. The only one I attend without fail is my journalism class, and that's only because of Emma and Hilary. I mainly walk down the hallways of my school, enjoying the peace and serenity that comes with it. And why not? I work hard for this school to run smoothly; don't I deserve a reprieve from study? Besides, I'm getting straight A's...Thanks to Emma. It's a time for me to plan the next school fundraiser or think about new rules that I need to enforce or just have some time to be alone with my thoughts.

"What the...Whoa!" I was pulled from behind by two pairs of hands into the ladies bathroom and I collapsed into a heap on the floor. "Ah." I cringed as I rubbed my head where it hit the floor.

"You're sure this is the guy Lucy Wells hangs out with?"

"I'm certain he is."

I opened my eyes to see Kristen Petry, a member of the cheerleading squad, and Winnie Hearst, one of the contestants up for prom queen, having a discussion about me as if I wasn't even there. "What the fuck." I exclaimed to the two girls. "What was that for?"

"Sorry, um, what's your name again?" Winnie asked.

This is good news. My anonymity is what I was hoping for when I brought Lucy on board. "Will. Will Harrison. Now what's going on?"

"And you hang out with Lucy Wells, right?" Kristen added.

"I know who she is, yes. Now the next words out of either of your mouths best be the answer to why in the hell am I in the woman's bathroom." I was more than slightly irritated.

"Alright, geez." Winnie rolled her eyes.

Winnie was actually annoyed with my answer. Really? She's the one who grabbed me and threw me to the floor without so much a warning or an apology.

Kristen kneeled down to me and picked up the conversation before Winnie could piss me off more. "Forgive her. She's just nervous. Actually we both are."

"Why be nervous?"

Winnie interrupted. "Do you know how Lindsey is getting a 3.4 GPA right now?"

That would be Emma. Lindsey has always been a blonde airhead, barely making the grades to stay an active member of the cheerleading squad. I didn't want any of the extracurricular activities I was giving her to hurt that. She makes me more money when she has the title of 'captain of the cheerleaders'. But I don't want them to know that, so I lie. "Um, I guess she studies."

"That's funny Will." Kristen chortles. "I don't think I've ever seen Lindsey read a book that wasn't in the Twilight series in her life." Kristen then shakes her head. "We think she has Lucy do something."

"Like what?" I play dumb.

"Well, you know Lucy sells her as dates to guys, so we figure Lindsey gets good grades in return. Lucy is student council president after all."

Like that means she has access to everyone's files. Idiots. They have no idea how much work went into that. "What's your point?" I really didn't care, I just wanted to leave. This conversation was lower my IQ by the second.

Kristen's hand went to my crotch. "We figure if we would just fuck you, you can convince Lucy to help with our grades. We don't want to repeat 12th grade, and we both are very close to having to." She flashed me her 'please feel sorry for me face' as her hand massaged my manhood to full length. "So, what do you say?"

"I would say I can accommodate your request ladies, but why should I?" If this is going to happen, it's going to be by my rules.

"Don't you understand what we're offering?" Kristen removed her hand in shock.

"Most guys would give their left nut to be with the two of us," Winnie snidely added.

"Yes, I know what you're offering, two on one sex for grades. But I've done so much more than that already." The girls looked at me disbelievingly. "Up the offer or enjoy senior year, again. And I recommend a change in temperament." I stood up. "Tell Lucy when you've made a decision." I left. Frankly I would've gone for it if it wasn't for their attitudes, or should I say Winnie's attitude. She definitely felt she would have been doing me a favor if it went her way. Besides, a wham bam, thank you ma'am on the floor of the high school bathroom doesn't sound that appealing. Who knows what diseases are crawling around in that place? I could end up with a birth defect. I chuckled out loud at my own private joke as the bell rang.

A week later and Lucy hasn't said anything about Kristen and Winnie. I have a small twinge of regret at not accepting their offer. I could've fucked Kristen and paddled Winnie's ass. Knocking her ego down a step or two would've made it worth it. Alas, I suppose I will have to settle for Emma, Hilary, Rachel, and Lindsey. Not bad consolation prizes if I say so myself.

I suddenly found myself being called to counselor Evans office. He wasn't even my counselor. I debated whether I would even show up or not, but decided the hell with it. You never know what opportunities exist if you don't check all opportunities that come your way. I knocked on the door.

"Come in."

I was surprised it was a woman's voice that came from inside Mr. Evans office. I opened the door and my mouth just hung open. A woman I have never seen before, and believe me, I would have known if I've seen her before, had her body propped up by her arms laying the width of the desk with one leg hanging over the side and the other bent at the knee. She was wearing a red and black corset with black stockings and high heels. She was a walking wet dream. Definitely not Mr. Evans. At least, I hope not.

"Well hello there," she said enticingly. "You must be Will Harrison."

"Indeed I am." I doubt I could've spoken more than those three words.

The woman stood up provocatively and put on a coat. "Would you be interested in coming with me?"

I nodded, still mesmerized.

I followed her to her car, a silver Lexus, and she was surprised I opened the door for her.

"I didn't realize I was in the company of a gentleman." She smiled at me.

I got in the passenger seat. "And what's your name Mademoiselle?" I tried to be smooth, but I doubt I was.

"Lorraine Winthrop." She stated as her car roared to life.

We only drove a couple miles before pulling up to the largest house I've ever seen up close. Suddenly, my stomach was doing backflips at the thought that I was found out by Brantley Sherwood and he was going to exact revenge on me. I was about to send a 911 text to Edwin and Stu when she put a hand on my shoulder. You would have thought I was on an ejector seat at how high I went in the air.

"You're sweet." Lorraine snickered. "Follow me if you think you can handle it." She exited the vehicle and I stared as she walked past the front of the car.

I gave myself a couple seconds to have a few deep breaths and steel myself. Up until this point, I was taken completely off guard and therefore, not in control. I am so much better than this. Lorraine turned to look at me to verify I was coming. I opened the door that instant and got out. Lorraine let out a slight gasp as she noticed my entire demeanor changed. She opened the door and I walked in.

"Nice place." I said nonchalantly as I glanced around.

"You should see the bedroom." Lorraine gave me a wicked smile.

"Lead the way Sexy."

I couldn't help myself. Half way up the stairs, I turned her around and gave her a kiss full of lust.

When we separated, she looked at me inquisitively. "You are quite good at that young man."

I just smiled and sunk to my knees. I wasted no time in exposing her pussy, but I didn't dive right in. I kissed, nibbled, and licked all around. She was soon moving her pelvis to try and get me to make contact with her now wet cunt. It was driving her mad.

"Please," Lorraine whimpered.

"Not until you tell me what this is about." I lightly exhaled on her quim and she quivered. I went right back to teasing her.

"I'm doing this for my daughter." Lorraine panted.

"Which is?" I sent my tongue up her slit, but barely made contact.

"Dear God." Lorraine shivered. "Winnie. I'm doing this for Winnie. She said you could get her to graduate this year but you turned her down. I don't want her to turn out like me, a pregnant teenager with no high school diploma who had to marry an 83 year old man just to survive. Now please, I need to be...Ohhhhhh!"

I drove my tongue as deep as it could go. However, I still took my time. I would only occasionally brush up against her clit as I explored the rest of her pussy. I built her up and then backed off repeatedly, keeping her on the brink.

Lorraine's knees buckled and she finally collapsed on the stairs. "Please let me cum!" She was begging. "I don't care if you help my daughter. Just let me cum!"

I waited a minute longer and then drove two fingers into her depths as I sucked her clit. Lorraine spasmed something intense and let loose a constant howl that reverberated off the walls. My head was trapped as her orgasm didn't even seem close to subsiding. Her cunt just kept gushing her juices and I had no chance to keep up. Lorraine finally relaxed, or I should say loosened her grip enough for me to get oxygen into my lungs. I crawled up beside her and put one arm on her. My fingers were wandering aimlessly over her perfect form as our breathing was coming back to normal.

"Where did you learn that?" Lorraine asked curiously. "I mean most guys do it because they feel obligated. Some won't do it at all. But you, oh my God. You turned that into an art form. You are already the best I've ever had and we haven't fucked yet. So where did you learn that?" Lorraine gazed at me lovingly.

My Principal is what I wanted to say, but I chose to lie again. "The internet."

Lorraine let loose a laugh. "Well young man." She stood up. "You've earned the right to have me any way you desire for as long as it takes for you to be satisfied." She gave me her hand and seemingly dragged me to her bedroom. Our clothes disappeared from our bodies as we started to make out. By the time we made it to her bedroom, we were nude and tumbled onto the bed.

"Well?" Lorraine asked almost impatiently.

"Since I did all the work on the steps, I'll let you be on top, but I guarantee we won't finish that way."

"A man with varied tastes." Lorraine straddled me. "I like that."

Lorraine began by slowly going down to the base of my shaft and back up. With each downward thrust, she would pick up speed until she seemed to be a woman possessed. I would buck into her and we soon developed a rhythm. She was good. Almost as good as Rachel.

I was ready to take charge. Without warning, I flipped Lorraine on her back and threw her legs over my shoulders. Using everything Rachel taught me about varying penetration and clit and g-spot stimulation, or in other words how to fuck a woman blind, I did just that. I pounded into her with force. She grunted through gritted teeth with each insertion and her eyes were as wide as saucers unable to break eye contact with me.

Another massive orgasm overtook Lorraine and moments later I joined her, elongating her bliss. I fell next to her and we encompassed each other in our arms.

Lorraine couldn't take her eyes off me. "Where did you come from? You're an expert at everything. I don't think I can let you go now."

"I told your daughter I was experienced, but I don't think she believed me."

Lorraine chuckled. "She thought you were gay after turning her and her friend down."

"No, not gay. I didn't like her attitude." I smiled back. "I actually started to regret it a couple days ago. If I would have thought then what I devised now, I would have said yes."

"And what is that?"

"I would've fucked Kristen and paddled the shit out of your daughter's ass," I said flatly.

Lorraine seemingly choked on air. "You spank your lovers?"

"I am a chameleon. Whatever the woman I am with wants, I do my best to provide. One loves for me to mix it up, letting our mutual love carry our experience. One gets off on punishment and pain, wanting nothing more than to be dominated. And yet another just loves to be loved, enjoying me being tender with her."

Lorraine appeared shocked. "How many girls are you with?"

"I juggle four women, and they all know about each other." Okay, the one that matters, Emma, knows about the other three. No one else needs to know about Rachel.

"Seriously?" Lorraine looked at me incredulously.

"Of course." I suppose I wouldn't believe me either. In fact, if I was in her position, I know I wouldn't.

Lorraine thought hard for a long moment. "Any chance I can get in your little rotation?"

Now it was my turn to be skeptical. "You were serious about not letting go?"

"I tend to get what I want." Lorraine kissed me lasciviously. "You have no idea what you just did to me."

I took a breath and regained my serious composure. If this is happening, it's going to be by my rules. "I think your husband would have a problem with that. And I would have to discuss it with my fiancé."

Lorraine noticed and tried to reclaim dominance. "Engaged at eighteen? You sure she's the one you want?" Lorraine draped a leg over me. "I can be the one. My husband passed two years ago."

Not going to happen. My way or the highway. "Yes, she is." I pushed her away and stood up. "So if you want to be one of my Mistresses, you would have to find your niche." I got dressed. "And I already have a fiancé, a slave, a whore, and someone who worships me. To be in my rotation, you need to offer me something of value." As I left I called out. "Don't worry about your daughter. She'll pass, her friend too." With that, I walked out the door. I doubt Lorraine has ever been treated that way. I bet she always utilized her body to get what she wants. I see Lindsey's future in Lorraine. I have bigger plans.

The next day, I was just about to exit the restroom to rejoin a patiently waiting Emma when I heard Winnie begin to speak to her. "Hey, Emma, what's up?" That seemed awfully cordial.

"Not much, just waiting for Will."

"I just thought you would like to know what, I mean, whom Will was doing last night." So that's the plan. Break Emma and me apart. Idiots. I now know where Winnie gets her stupidity.

"Well, first he had school, then he fucked your mom, then he came home in which I had his favorite dinner prepared, and finally we made love until almost midnight. When were you talking about? I don't think he had time for anything or anyone else." That's my girl.

"He told you?" Winnie sounded stunned. Why does no one believe me when I say there are no secrets between Emma and me?

"Absolutely." I can almost see Emma's smile across her face. Her tone said she knew she defeated a former antagonist. "Oh, and by the way, Will said he was impressed you and Kristen were able to think outside the box and your grades will be updated."