Mommy Issues Pt. 01

"Do you know why you're here, Mr Thompson?"

The here in question was Principal Shepard's office, next to the reception of the school. The why was quite simple.

"Because you can't get enough of me?" I asked, grinning.

The Principal smirked ever so slightly in response to my grin, and for a moment I'd made a breakthrough. Until, at least, she leaned back and opened one of her drawers.

"Because," she said, taking a file out of her desk and slamming it down on the table between us, "Your grades are dropping."

Two reasons, then. But I knew she liked me.

Midyear blues it was called, where every student had to buckle up, stop partying, and actually sit down to study. Every student aside from the football team, at least. Coach had promised us that he'd get those grades for us, so long as we kept winning. It seemed like a fair deal, and one we'd upheld the entire season. And besides, I was well on my way to get a scholarship. They didn't give half a shit about my gpa so long as I could throw a ball well. So I wasn't worried.

And like I said, the Principal loved me. She couldn't get enough of me. There was a reason she turned up to every football game, and it sure as hell wasn't to support the team, or represent the school. There was a reason she always called me up to her office, to deal with me, instead of letting one of the old bags yell at me. And there was a reason she always stared at my ass as I left, and came into the changing rooms to congratulate me on a stellar performance while I was half-naked.

And I loved the attention. Who wouldn't? For a teacher, Mrs Shepard was absolutely stunning. She was like one of those models you saw in magazines, or a pornstar. Curly red hair on a beautiful, sharp face and freckles, with pale, white skin, despite the year-round sun. Tall, but not too tall, without any fat on her at all. She always wore light blue dresses, though they did nothing to hide her curves. She was built like an hourglass, with triple D cups and an ass like a beach ball.

Yeah I know, a bit horny. But you couldn't help but be horny around her. It was like she was built for sex. The kind of person who shouldn't be working in a school, having to deal with obnoxious teenagers (me included) but should be getting fucked and worshipped every waking moment.

To anyone else, she would have been the most beautiful person they'd ever seen, and it wasn't even close. To me, however, it was a tie.

I was admittedly a little spoiled for choice. Everybody in the school had eyes for her. But she could only think about me. It was pretty nice.

My name's Alex Thompson, by the way. I figure I should probably introduce myself in between the detailed descriptions of the women in my life (and there's a lot of them). I'm 18, about 6'1, blonde, and the captain of my football team. I'm saying this because these are some of the reasons I found myself in the situation I was in. My dad once said high school is just sex with occasional lessons, and that was about the sum of my experience. Cheerleaders, library girls, milfs at a bar, by this point I was basically fucking anything that moved. What can I say? The ladies loved me. And I loved them back. It meant I got spoiled for choice. It meant I got ambitious. It mostly meant that I wanted to guck my principal at the moment.

Speaking of:

"Busy doing what? Going to parties? Kissing girls?" Principal Shepard knew me too well.

"Please, Mrs S," I replied, "you know I prefer older women."

There was that smirk again.

"I understand." she said, and now the smirk had turned into a full smile as she flashed her perfect white teeth. "But you need to understand that older women prefer intelligence over a brainless sack of muscles."

"Wanna bet?"

I was willing to lay everything on the line that if she had to choose between me and one of those fancy lawyers, she'd be riding me in no time.

She smiled again. "Get going Mr Thompson. You've got quite a few tests to study for if you want to have even a chance of getting a passing grade. Otherwise you'll be seeing me here again this time next week."

"This time next week, then. It's a date." I replied, both of us knowing I had no intention on studying for any of those tests.

I checked the clock as I walked out the office, knowing Principal Shepard's eyes would be focused, as always, on my ass. Too late for football practice. Coach would kill me, but there was no point going now. Oh well.

I'd be home in time for dinner at least, which was good. My dad had been on my ass the past few weeks about how I needed to make time for family, to talk to him and my stepmom.

My stepmom, Danielle. The only other person who could compete with Principal Shepard. Describing her was impossible. It was an insult to her. Trying to put her beauty into words just didn't work because no matter how much I exaggerated my words they wouldn't do her justice. I'd try my best, but I couldn't promise anything of it: she had long blonde hair, and the kind of face and lips that were so perfect that you thought she was a statue at first. And in a sense she had to be, there was no way anything other than a manmade sculpture could have such a perfect body. She was slender, almost skinny even, but with the largest, roundest breasts and ass I'd ever seen in my life. In the times we'd gone to the beach together, I'd seen just how large her breasts were as they strained against her bikini, the mounds of her ass completely hiding her g string from sight. Every man on the beach would, unfailingly, stare at her, myself included, though I tried to restrain myself out of respect for dad. Still, it was hard. As was I, most of the time we went out together. It was impossible to choose who was more attractive between her and Principal Shepard. Recently, I'd had my sights set on the Principal, but that was because I knew there was no chance I'd ever get to fuck my stepmom, no matter how many times I'd jerked off to her.

Between the two of them, they'd ruined porn for me. I was a horny guy, I won't deny it. I'm into most things, with a kink for almost everything I've seen. Tits, ass, thighs, feet, anything and everything aroused me. So it was a wonder that between my stepmom and Principal Shepard I wasn't walking around with a boner my entire day.

And dad? Dad was, well, dad. Let's just say all of my genetics had come from my late mom's side of the family tree. Not to blow my own trumpet here, but like i've said, I was tall, blonde, and athletic. I'd always had a good physique, but ever since starting football and hitting puberty, I'd grown into my frame, with veins and striations accompanying my muscles and washboard abs. And below my abs was perhaps my best genetic quality.

Now none of that was really thanks to dad. He was short, skinny, and with a receding hairline. Or, rather, by this point his hairline had already receded.

So how had he bagged a goddess like my stepmom?

The answer was the same as every other middle aged man who had married a supermodel-level girl: money. As I opened the gate to our mansion, it was easy to tell where Dad's positive traits lay. His job had earned him a fair amount of money, more than enough for us to be well off. More: we could afford anything we wanted. I could afford to drop out of school. Not that I wanted to. I still had dreams of going to a nice university and getting my scholarship. And if I was honest with myself I still had a goal to fulfil: bagging Principal Shepard before I left the school.

"I'm home!" I called out to no-one in particular as I opened the front door and pulled off my shoes.

The first person to greet me was dad, as I saw him step down the stairs.

"In time for dinner for once." he said, giving me a brief hug, before heading to the kitchen.

"Yeah, just in time." said Danielle, as she stepped out from the kitchen, dressed only in a robe. She stepped forward to give me a hug, a proper one, unlike dad's, pulling me forward until I could feel her chest press against mine. If I hadn't known better, I'd have said she was doing it on purpose.

"Hey mom." I said, feigning gasping for air ever so slightly, but really trying to get my raging hard-on away from her as quickly as possible. "Good day?"

"The usual." she said, and winked.

The usual. Another day at home doing laundry and cooking dinner. She'd been a stay-at-home mom ever since she'd married dad. I carried on regardless, walking with both of them to the dinner table, where she'd already laid the table and placed the food.

"I'm glad you could make dinner for once." my step-mom said as she handed me a plate. "I made a special mushroom risotto. I think you'll like it."

And soon enough, we were sat down by the table, eating. Strangely enough I didn't feel hungry, maybe because I hadn't exercised for the first day in a long while. Either way, I couldn't get much of the food down, even though it tasted delicious, as always.

"So, champ, good day at school?" my dad asked, shovelling some more of the rice onto his plate.

"Average really. Nothing much happened." I said, carefully skipping over my trip to the Principal's office. Principal Shepard was kind enough to forget to email my parents whenever I met with her, and I saw no reason to have to bother my dad about it either.

"Fair enough. Looks like quite a boring day for all of us, then."

"You can say that again." my stepmom said in between bites. "Today was downright boring."

That evening wasn't any different. I had a bunch of studying to do for the next day. Not that I did any of it, but the fact that I had a school day the next day meant I couldn't really fully relax. I tried everything, taking a nap, playing some games, even jacking off in the bathroom. But nothing worked. I just wasn't in the right mood for it. But maybe it wasn't the fact that I had school the next day. Maybe it was Principal Shepard. I always felt in a funky mood after meeting her. Jacking off just didn't do anything for me, but I didn't have the time to get a girl to come round, or to leave the house. It was a Thursday, after all. But sleep didn't come either

So, resigned to my fate, I got up and headed downstairs. When in doubt, the best thing to so, I'd found, was to watch a movie. I headed to the flatscreen tv, opening the cupboard beside it for the dvds. Yeah, I know, old school. Antique, even, you might say. That was just my dad. He wasn't fond of modern technology. Netflix was a lost term on him.

I spent a few minutes looking through the films before settling on one. Tropic Thunder. Why not. We hadn't watched it in a while anyway. I took the dvd out, and pressed the player to let me put the disc in. It was then that I noticed something strange. There was already a disc in there. But unlike the movies it was fully blank, with only the date "10/25" written on it in marker. The 25th of September. Today's date.

Normally I wouldn't have cared. Normally I wouldn't have given it a second thought, tossing it to the side to put in the movie. But for some reason

Oh well, curiosity killed the cat, but satisfaction brought it back. I pushed the disc back into the tv, and waited for the screen to turn on.

What I saw next completely floored me. It was porn. A naked woman getting aggressively fucked in both holes by two men. No. It wasn't porn. It wasn't a porn-star.

"Mom." I whispered, disbelievingly.

It was her. It was my stepmom, fully naked. The film was already halfway through playing. Well, it wasn't a film. It was a tape.

A sex tape. From today it seemed. But it wasn't dad in the picture. It wasn't even one person. She was getting fucked, up the pussy and ass, by two burly men.

I blinked in disbelief. This scene couldn't be happening. I had to be hallucinating, or dreaming. But it was real. Starkly, shockingly, real. And I couldn't break my gaze from my stepmom's beautiful pink nipples and her perfectly shaved pussy. If I'd thought she was beautiful before, now I thought she was perfection itself.

"FUCK!" one of the men yelled as he drilled inside her.

I was slack-jawed, my mouth dry, as the scene shifted. Now, the man who had been fucking her ass pulled out, a few strings of lube or spit or whatever substance hanging from her ass onto his thick cock, before walking round and shoving the entire length of his rod down her throat without a second thought. Thank god the volume was low. Even as it was, the sound of moans, and of my stepmom gagging, was faintly evident.

But soon the moans were growing louder. I heard the faint sound "take it slut" as the man fucking her mouth pulled away and the other put a hairy, sweaty, foot directly on her cheek and nose, right on her face, pushing her head into the couch. My stepmom made a disgusted face, similar to when you're hit by a foul smell, presumably because of the smell of his foot so close to her nostrils. But she didn't tell him to stop. In fact, I could hear her, though her voice was muffled by his foot, shouting.

"More!" came her voice. "MORE!"

This continued for god knows how long. Time seemed to fly as I watched. It could have been seconds, it could have been hours. Eventually, they stopped with a grunt, both of them sitting down on the sofa. Standing up, my mom smacked them on the asses as if they were naughty children, hard enough that there were red marks where her hands had been.

Then, she leaned down, until she was kneeling in front of them.

"I know what you like." she said with a sneer.

As they leaned back and put their feet in the air, she spat into each hand, and, reaching down, began to rub their assholes, just like she used to rub sun cream into my back.

As she did so, she reached forward to their outstretched feet and began lapping at them with her tongue, until she was fully sucking their toes, first one's foot, then another, swapping between each one every few minutes.

God, that was disgusting. I couldn't imagine ever doing something like that. And yet she was sucking their toes with vigour as she rubbed her spit into their assholes, sometimes going so far as to push a finger slightly in, before pulling it out with a pop.

And now the men were moaning, moaning like girls as they stood up again and frantically masturbated over her.

I looked down briefly to see that I had a tent in my pants. I'd quite literally never been harder. In spite of myself, I started rubbing myself through my pants. It took every bit of my willpower to not pull out my dick immediately and start stroking.

Those moans had turned into full on grunts as their breaths deepened and they began to cum. They were at it for nearly a minute, and by the time they were done they had absolutely painted my stepmom. She was covered in white, both her tits and face. She was still gorgeous as ever, but her hair was a mess and her makeup was smeared. But it was her reaction that surprised me the most.

As they groaned, enjoying a post-orgasmic glow, she looked up with a twinkle of fury in her eye.

"Again." she sneered.

But she was met with shaking heads and waving hands.

"No." one of them said. "We've done it three times already, give us a moment to rest."

"Again!" she said, this time more forcefully

Leaning forward, she closed her teeth around the now limp cock of the closest one, tugging at it like a dog. He began to whimper, begging her to stop as she bit down. By the time she let go, the teeth marks on his dick were evident.

"You want some as well?" she turned to the other man, still kneeling, as he began to beg and plead.

Annoyed, she slapped his dick and stood up as they both collapsed back onto the couch.

"Fucking come on you pussies!" she screamed at them. But they were done. Spent. Completely drained. She'd defeated them.

The last thing I saw was my stepmom shaking her head in disappointment or disgust, lube, spit and cum all hanging from her tits in a sticky mess as the lens focused on her sweaty body, as she went to turn off the camera.

"Alex?"

My hand went to the remote and the tv was switched off in an instant. I'd never been that fast, not even in any of my best games.

I turned round just as my stepmom stepped into view from the door, still wrapped in her robe, rubbing her eyes, half asleep. God, even like this she was gorgeous. It was unfair. But my mind was racing and my heart was pounding. I'd just seen what was below that robe. And more. I'd seen everything.

"You okay? I thought I'd heard something."

I smile slightly, trying to disguise my shaking. "Sorry mom. I couldn't sleep."

"Well try again, silly," she said, standing up on her tiptoes to kiss my forehead. "You've got school tomorrow again."

Should I be disgusted, knowing where those lips had been earlier today? I left the tv room, leaving her behind to do god knows what. Did she know I'd seen her tape? Did she think I knew? What would she say?

As I walked up the steps, I kept replaying the scene over and over in my head. Her getting double penetrated. Her getting spit-roasted. Her getting her face stepped on. Her sucking their toes and cleaning their asses. And more.

But what really stuck with me was the ending. When both men had come and were lying on the sofa exhausted.

"Fucking come on, you pussies!"

She'd completely overwhelmed them. No matter how much they'd tried to dominate her, or get her to submit, she'd fucked all three of them into a sopping, begging state. Pleading for her not to go on.

God, she was filthy.

Did dad know about this? Surely not. I'd never even thought it was possible. I'd never thought that she could do this. And she'd said her day was "downright boring". That bitch. It was so wrong. It was fucked up on so many levels. I should tell dad. I should scream at her.

And yet.

And yet I couldn't help but feel that Dad deserved this. He wasn't handsome, or strong. He certainly couldn't be good at fucking. The more I thought about it, the more I justified it in my head. I mean, my stepmom was a goddess. She deserved to be well fucked, not to be wasted around dad.

She deserved a real man.

Was I that man?

It was then that I realised. I'd just seen everything. I'd just seen her fucked in every hole raw, and doing filthy things, things I couldn't have ever imagined her doing. And yet I wanted to see more. No, I wanted to be there. I wanted to be the one to put her in her place. None of those men had been able to last, to really fuck her as a man should. I shivered as I reached my room.

I wanted to fuck my stepmom.