High School Harem

This is the 6

th

installment of my High School Harem series. Sorry it took so long. For those of you still with me, you have my utmost appreciation. As usual, any and all feedback is welcome.

Now, I am aware that I may have lost some readers due to the direction I'm taking the story, and I apologize if you feel that I've ruined it for you. But this is the direction I'd always planned to take it. It's meant to show that despite how crappy the main character's family treated him, it turns out they're just as screwed up as he is. I mean, his dysfunction has to come from somewhere, right?

For the rest of you who weren't turned away by the direction I'm taking the story, I hope you enjoy. I'm certainly enjoying the writing process, and I enjoy reading you guys' feedback. There's still more to come, after all winter break has to end sometime, and when our main character does get back to school his world is only gonna get crazier.

*****

I'm a fucked up person.

I was at home for winter break. To be honest, it was weird being back home, that's not to say I wasn't having fun though. Hell, within the first 2 days I got a blowjob and sex from one of the most beautiful women I know. That woman was my mother, and that's where the weirdness came in. At first, I thought I could rationalize it, by saying we're just a man and a woman satisfying our needs. And I told myself that wasn't going to feel ashamed or guilty about it, after all, why should a guy feel guilty for satisfying his needs? But no matter how much I tried to convince myself, I still knew how wrong all this was. And the fact that I enjoyed it? Well, like I said, I'm a fucked up person. And my mom, who initiated all this, I wondered how fucked up that made her?

Over the next couple of days my mother and I could hardly be in the same room with one another without our lust and passion taking over; we were insatiable and almost quite literally inseparable. However, all good things must come to an end, temporarily at least. Because then Friday rolled around, the day my older sister would be flying home, and we couldn't very well let her see how we'd been spending the past couple of days. So mom and I both agreed we would need to stop for the time being, until we could figure something out. After all, just because we didn't have a problem with our arrangement, that didn't mean other people wouldn't.

On Friday morning, just before noon, I awoke to my phone ringing. As I stirred from my sleep I immediately noticed mom wasn't in bed with me. Without much time to wonder where she could be, I answered my ringing phone.

"Hey sweetie, good morning." mom's voice greeted me on the other end of the call.

"Oh, hey mom, I was wondering where you went." I replied, wiping the sleep from my eyes with my free hand.

"Something came up at work and I had to go to the school to take care of it." she said with a sigh.

"Is everything alright?" I asked.

"Everything's fine, just loads of paperwork. Though, I won't be home until rather late, so I need you to do me a favor."

"Sure mom, what is it?" I replied without thinking, though I could've guessed what her answer was going to be.

"Well, Ash's flight will land around 2 and I won't be able to make it to the airport to pick her up. So I need you to." mom said.

This was none too thrilling; I hadn't so much as spoken to Ash, my sister, in over a year.

"...Mom, are you sure about this? I mean, you know Ashley is not gonna be thrilled to see me." I asked.

"I know, but I wanted to wait to explain the truth to her in person. So, please just bear with it, for me honey?" mom replied.

"I don't even have a car to drive up there." I said, hoping this excuse would be my last bastion.

"Yeah, you do, sweetie. Did you not see? I left your car keys on the bedside table." mom said.

I glanced to the left and sure enough, there were my keys, right where mom said they were. Damn it, there's no way I'm getting out of this, I thought. While I appreciated finally having my car back, I dreaded having to pick up my sister.

"...okay, I'll do it..." I said, seeing there was no point in arguing.

"Thank you, honey. Just please bear with it until I can get home and I'll explain everything to Ash, I promise." mom said.

By the time our call ended it was just a few minutes past noon. Ashley's flight was due to land at 2, and the drive to the airport would be about 30 minutes, so I would need to shower and be ready to leave by 1:30. I went to the kitchen and fried up some eggs for breakfast. After eating, I put my dishes in the dishwasher then went upstairs to have a shower. When I finished showering I went to my room and got dressed, then I went down to mom's room to make sure none of my clothes were still in there. With all that taken care of I had just a few minutes before I needed to leave.

The drive to the airport took a little longer than 30 minutes so I ended up arriving around 2:15. So as if my sister didn't hate me enough, now I was late. Just wonderful, I thought. As I pulled up to the pick-up area I quickly noticed a girl standing with her luggage, I recognized her immediately, it was no doubt my sister. Here goes, I said with a sigh as I pulled the car up next to her.

"...oh... it's you.." my sister said with disdain upon seeing me.

Yep, that's about the greeting I expected.

"Hello to you too, sis, glad to see you haven't changed." I said sarcastically, to which Ash rolled her eyes in response.

We both shrugged off this little exchange and went about loading her bags into the trunk of my car. We departed the airport without another word and remained that silent the whole car ride home. But, you know, actions speak louder than words anyways, right? The whole car ride home, anytime I glanced over at my sister she would just give me these disgusted looks. I didn't say anything, I just bottled it up and tried to bear with it like mom had asked.

When we finally got to the house and got her bags inside, I went to the living room to watch TV while Ashley unpacked in her old room. After a while Ashley came downstairs to the living room, still looking at me with disdain.

"So, where is mom anyways? She was supposed to be the one picking me up, not

you

." she asked, the last part she said with exaggerated disgust.

It was obvious that she was trying to hurt my feelings, and she succeeded. But once again, I held it in, just telling myself that mom would be home to sort it out eventually.

"Something came up and she had to go into work, she said she'd be back this evening." I answered her.

"What'd you do this time? Kill a girl?" she asked sarcastically.

No, but I'm about to, I thought to myself. It was getting harder and harder to hold it in, but I just continued taking her verbal abuse in stride. Feeling my anger rise, I turned my head back to the TV to ignore her.

"Great, so I'm stuck at home alone with a rapist." she said coldly, turning around to walk back upstairs.

"At least I ain't a goddamned bitch." I said firmly and calm.

I regretted saying it right after the words left my mouth, I'd never called my sister a bitch before and I never thought I would. I knew I should've just let her walk away, but I couldn't help, I just had to go and open my big stupid mouth.

"Go fuck yourself, you pathetic loser, you make me sick." my sister shot back, clearly upset.

And that was it. That's when I finally reached my breaking point, she clearly wanted to piss me off and I was taking the bait.

"I've said it before, but fuck it, let's hear one last time just for the cheap seats. I did NOT rape that fucking girl!" I stood up from the couch and began yelling.

Ashley looked shocked, after all, she'd never so much as seen me raise my voice.

"I am so fucking sick of everyone accusing me of some bullshit that I never did! Fuck! Makes me so goddamned mad! Like I would ever fucking do something so fucked up!" I began pacing around the living room, yelling at the world pretty much.

That last part, it was priceless coming from a guy who'd spent the last few days banging his mom. The problem was, I was just that fucked up. But I wasn't in the mood to dwell on my hypocrisy.

"But nobody cares to hear my side of the story, not my so-called friends or even my own fucking family! You have any idea how bad it feels to know my own family hates me because of some bullshit lies that some cunts decided to make up! Even you, Ashley, my own sister, the one person who I thought for sure would have my back. You go around calling me vile shit like rapist without thinking twice about!" I continued ranting and pacing the room, seething with rage.

Ashley just stood frozen at the foot of the staircase, listening to my rant with a shocked expression on her face. I could see that tears were forming in her eyes, she looked genuinely horrified. Any other time I would've succumbed to my weakness for women's tears and began apologizing profusely, but this time I was just too angry.

"Fuck it! You clearly don't want me here, so I'll just go! I'm done with this fucking family." I grabbed my car keys from the coffee table and stormed out the door.

I got in my car and pulled out of the driveway as fast as I could. I began driving with no particular destination in mind.

I hadn't been driving for very long, my anger hadn't subsided completely but I was able to think rationally. I really shouldn't have blown up like that, I told myself. If anything, I was now mostly angry at myself for yelling at Ashley like that. My sister could never handle being yelled at, anytime someone yelled at her she'd usually always start crying, and it seemed she'd never grown out of that. In fact, I'm sure seeing my sister cry as a child was probably what instilled in me a weakness for tears. Even with her insulting me like she was, she's still my sister and I love her, making her cry is the last thing I ever wanted. I just wished she and I could go back to the way we used to be. Ashley and I used to be so close, practically inseparable, we could talk to each other about anything. But it all changed after that incident, I thought for sure that even if everyone else shunned me after that event, she wouldn't. I thought she'd be the one person to listen to my side and talk to me, but alas, I was wrong.

What now? I asked myself as I drove aimlessly. I certainly couldn't just go back home. So, what am I supposed to do? I would soon receive the answer to that as my phone began to ring. I took one hand off the steering wheel and reached in my pocket for my phone. Careful to keep my eyes on the road, I checked my phone quickly, it was mom calling. I sort've expected to hear from her as Ashley had no doubt phoned her after I left.

"Hey, mom." I answered the phone.

"Hey, sweetie, I just heard from Ashley. You guys had a little fight?" mom said.

Yep, I was right, Ashley had indeed called her. Though, I don't know that I'd call it a fight, it was mostly just me yelling and storming out of the house like a madman, but whatever.

"Yeah, sorry mom. I didn't mean to lose my cool and yell at her, but I just can't be around her right now." I responded.

There was no need to explain the situation, after all, mom knew better than anyone how the rest of the family has treated me ever since the incident.

"I understand, honey. I promise I'll talk to Ashley when I get home. In the meantime, if you don't wanna go home, why don't you come keep me company at the school. I'll be here a few more hours doing paperwork" mom said.

I mulled over her suggestion. Sitting around waiting for her to do paperwork was sure to be boring, but it was probably better than driving around aimlessly, and was definitely better than going home to put up with my sister.

"Alright, I'll see ya in a bit." I said.

"Good, just come to my office when you get here. Drive safe, honey." mom said before hanging up the phone.

I put the phone in my pocket, pulled the car into nearest parking lot, turned around and resumed driving in the direction of the school. After a while the turn off for the school came up. Who would've thought that in the first week of winter break, I'd be going back to the school? I asked myself as I drove onto campus. I parked my car, got out, and began making my way to mom's office in the administration building. The whole building was empty, as the rest of the staff were all at home with their family, all except mom who took her responsibilities so seriously that she would sacrifice family time just to come do paperwork. Of course, it drove me crazy that she was 'married to the job' as they say, but I also admired that about her. She loved her job, but that didn't mean she didn't also love her family, one thing could be said, she never brought her work home with her. In fact, mom at home and mom at work were almost like two distinct people. At home she was the tender caring mother I knew and loved. At work she was the firm but fair authority figure that I respected. Let's call her two personalities "mom mode" and "headmistress mode".

When I got to mom's office I saw that she was busy at work, the door was open so I just walked in. She was sitting at her desk, staring intently at her computer monitor with her reading glasses resting on the bridge of her nose and her long brunette hair tied back in a bun. She was wearing her typical work attire: knee length black business skirt, a nice white blouse, tan stockings, and black leather pumps. To be honest, she looked like every guy's teacher fantasy.

"Hey, Alan, I've been waiting for you." she said, looking away from her work for just long enough to greet me.

"Hey." I replied.

"Shut the door behind you." she said before I could sit down.

I obliged and shut the door.

"Good, now lock it and close those blinds on the window." she said, looking over the rim of her reading glasses.

I was confused, but once again obliged her without question.

"Now then, come over here and get on your knees." she gestured behind her desk.

I knew then where this going, and while I was no doubt willing, I felt a little hesitant considering where we were. Plus, it had caught me off guard. I thought we'd agreed to stop with this thing of ours for the time being since Ash was back in town and the rest of the family was due in town as well. I'd barely even stepped into mom's office and she was already seducing me; how could I not be surprised?

"You sure, mom, here?" I asked.

"We're at school, which means you call me Headmistress or Ms. Campbell. Now get over here and don't make me tell you again." she said with a completely serious look and tone.

I didn't say anything, I just listened to her and made my way behind her desk as she turned in her chair to face me. There was no doubt that mom was in her headmistress mode, needless to say, I had no idea what to expect from her, but I found myself turned on nonetheless.

"No, wait.. first, take off your clothes." she commanded just as I was about kneel down.

That didn't seem like anything too unexpected, maybe headmistress mom was just like regular mom after all. I obeyed her and began stripping out of my clothes. I pulled my shirt off and dropped it to the floor. I then removed my shoes and began pulling down my pants. I was now stood before mom in just my boxers and socks.

"Underwear too, and socks.. everything." she said.

Okay, I said to myself. I pulled off my socks and dropped them on the floor with my shoes. I then began pulling down my boxers, exposing my semi-erect cock inch by inch.

"mmm... good.." mom said, looking at my exposed manhood.

I didn't get on my knees yet, I just stood there awaiting further instruction. Mom reached her hands under her skirt and lifted off her chair slightly as she began pulling down her panties. When the panties got down past her knees, I could see that they were actually a black lacy thong. I wasn't even aware that my mother owned any sexy underwear. She pulled the thong down the rest of the way and handed it to me. I wasted no time in burying my face in the damp crotch of her thong. I inhaled the strong musky aroma of her aroused pussy, it was so intoxicating that I almost collapsed.

"Put it on." she said.

"What?" I asked, caught off guard, crossdressing was not my thing.

"You heard me, put my thong on." mom said in a more commanding tone.

I never expected something like that from my mom, then again this wasn't exactly my mom. This was a direct order from the headmistress, and despite having never had any interest in crossdressing of any kind, I felt like I had to obey her. Without another word, I held the thong open and stepped into it one leg at a time and pulled it up the rest of the way. It was a little snug, as it hadn't exactly been designed for a dude to wear, so my semi-hard cock fought like hell to escape the crotch of the thin lacy material. I could feel my face and ears begin to burn as mom looked me over, but I have to admit, it did feel pretty erotic. It wasn't something I could see myself doing on a regular basis, but in this particular situation it felt kind of hot.

"Good, now, on your knees, Alan." she said.

Once again, without question, I obeyed her orders and got down on my knees in front of her. She lifted her skirt up and spread her legs revealing her dripping wet pussy and thick bush.

"Now then, eat my pussy." she commanded.

Not that she had to command me, but it did feel pretty hot having her give the orders. I leaned towards her, inching my face ever closer to her crotch, the strong musky scent of her dripping wet snatch getting more intense the closer I got. I buried my nose in the thick patch of fur above her slit and took a giant whiff, I had to stifle a groan the smell was so euphoric. I slowly ran my tongue along her outer lips, getting a good taste of her juices as they leaked from her pussy.

I wasn't the most experienced pussy eater in the world, but I knew a little bit. I used two fingers on one hand to part her lips, I then ran my tongue from her pulsating hole up to her clit. I flicked my tongue across her sensitive clit and mom yelped with pleasure.

"mmm.. fuck.. that's it" she said breathlessly.

With my free hand I began fingering her sopping wet pussy hole with 2 fingers. I ravenously licked and sucked on her clit as moaned and yelped uncontrollably. I was sure she was close to cumming when suddenly I felt mom's hand pushing my head away from her. I drew my head back from her pussy and looked up at her, my face soaked in her juices.

"That was good, Alan." she said.

I didn't exactly know how to respond so I just nodded silently. Mom stood up from her chair, hiked her skirt up and sat on the edge of her desk, she kicked off her heels and then spread her legs.

"Now then, fuck me." she commanded.

"Yes, Headmistress." I said as I stood up without hesitation.

I was still wearing her thong, my rock hard cock had grown to its full length and the thin lacy material was stretched to its limits. I assumed the position between mom's legs and pushed the thong to the side, at last freeing my aching hard on. I lined my cock up with the entrance to her pussy and grabbed mom by the hips as I buried my full length in her tight wet hole.

"ahh.. fuck!" mom yelped as her pussy stretched to accommodate my girth.

I started thrusting slowly at first but soon enough as her pussy got wetter and loosened up even more, I was furiously pumping my cock in and out of her with reckless abandon. I grunted and groaned with every push. The sounds of mom's heavy breathing and constant moaning spurred me on. Mom began viciously rubbing her clit as I pumped into her wet hole.