We'll Do Your Mom First, Then Mine, I Told Kev

by

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, Incest, Mother, Son, Sister, First, Pregnancy, Size, .

Desc: Erotica Sex Story: Two teenage boys, nerdy but horny, realize they need help if they're ever going to get anywhere with women. So they get Will's 16 yo sister and her friends to help in their transformation. But when it comes to their virginity they think first of their mothers...

"We'll Do Your Mom First", I Told Kev

1 - Late May 2010

"I've decided, we'll do your mom first, then we'll do mine," I told Kevin as I leaned over and clicked a key on his computer. A millisecond later the movie we'd been watching, a movie featuring an impossibly well endowed blond being fucked both anally and vaginally by two uniformed policemen, disappeared from the screen and was replaced by a picture of Kevin's mother.

Both of us had been sitting against the headboard of his bed, with the computer between us, as we stroked our cocks.

"Put the movie back on," my best friend ordered.

"I want to fuck your mom, not some porn star," I answered as I sat up and brought my engorged cock towards the screen and the picture of his mom that filled it.

"You're fucking sick," he said but his hand hadn't stopped moving over his virgin, eighteen year old cock. I hit another key and a second picture of his mom appeared. This one was an 'up her skirt' shot that I'd managed to surreptitiously snap a couple of weeks earlier.

"Where'd you get that?" he demanded as his eyes slid up his mom's legs to the triangle of white panty showing at their juncture. I laughed, then blocked his view as I touched the spot he was staring at with the tip of my cock. The drop of precum that had already formed slid onto the screen.

"You asshole, you'll ruin my computer," he complained as he watched the cum ooze slowly down the screen.

"Maybe I'll impregnate it and father a little notebook," I said, then laughed and shook my cock at him.

"You're a fucking idiot." Kevin was still stroking himself. We both froze when a second later we heard a knock on his bedroom door. It had to be his mom.

"Boys ... boys?" The call, muffled by the door, came seconds later. Kevin, already out of the bed, was struggling to pull on the pair boxer shorts he'd dropped on the floor just minutes earlier.

"Kevin? William?"

I walked towards the door, my cock in hand. Kevin, shaking his head wildly, was looking at me in horror. "Don't!" he cried.

"Mrs. White?" I asked through the door.

"I didn't want to disturb you boys Will, I know you're studying," my friend's mother apologized. "But I was just wondering if you'd like another piece of apple pie and a glass of milk."

"Yes, please, I'd love a piece of your pie ... so would Kev," I answered. My hand was now flying over my cock.

Kevin, across the room, was still shaking his head in despair. His penis, fully erect, shorter perhaps than mine, but still well above average, was sticking out of the slit in his shorts.

"Okay, I'll be right back," Kev's thirty-four year old mom promised. My cock started to spurt as I listened to her words. Thick strands of sperm arched upwards and out before finally landing on the back of the bedroom door.

"You're fucking crazy. Christ, she'll see it, smell it," he croaked as he pulled his jeans up his legs.

"I'd like to put some of this in her hot and hairy little momma's pie," I answered as I trailed a finger through my cum and then held it up in the air.

"Get dressed ... clean it up," he begged as he threw me my boxers.

"She's going to be our first," I insisted as we waited for his mom to return with the goodies.

"You're a fucking pervert," Kevin answered.

"Somebody has to be our first."

"Retard. Have you by any chance ever heard the word incest?"

"It won't be incest when my cock's inside her," I said with a leer as I ran my hand suggestively over the front of my pants.

"She's my mother!"

"That's why I'm going to let you go first."

"What!"

"But when we get to my mom I'll go first."

"Your mom! You are so fucking sick."

"Well who do you want to fuck then?" And of course Kevin had no answer to that one. I pressed on. "C'mon Kev, you read the study ... you know the first two or three weeks we're up there are going to make or break us."

"We have all summer to get ready, to find someone to teach us," he protested.

"So where do we start then? Who on your list do you think you'll be able to get to help us?" I challenged.

"Yeah, but what about my dad? And yours?"

We'd both pulled on t-shirts and shorts and were sitting at the long table that sat under his bedroom window, and which we used as a work desk, when his mother, toting a fully laden tray, finally reappeared. I knew we'd be continuing the conversation later.

Mrs. White was hot! A true MILF! Really she was far too young to be the mother of an eighteen year old. As fifteen year old Michelle Thomas, a neighbor of the Whites, she had ended up the prime baby sitter of Kevin's older half sisters when Mr. White's first wife had died some twenty years ago.

The eight and nine year old girls, bereft after the loss of their mother, had latched onto Michelle immediately and would cling to her desperately at the first sign that she was about to leave. Apparently the then forty-five year old Mr. White had too because just weeks after her sixteenth birthday young Michelle was walking down the aisle to be married. Kevin, "in uterus" at the time, was present at the ceremony.

He was their only child but against all odds the marriage had gone along famously. My parents had moved in two houses down from the Whites when I was three. And so we had become best friends.

Kev and I grew up nerds. Boys who'd been oblivious to the charms of the other sex as we'd studied our way through high school. Until, that is, our cocks started to grow. And spurt.

The two best students in our school, already pre-accepted into Princeton before our senior year had even started, socially incompetent but relatively happy, had suddenly been thrust unprepared into the world of cocks and cum and cunts.

Our senior year had been disastrous – week after week and month after month of uncertainties, rejections and self doubt. If we hadn't had each other I don't know what would have happened.

Hey look, I'm not stupid. It's impossible for a teenager to be ignorant of sex these days. Just turn on your computer! So, on a theoretical basis, we should have been prepared. And we were. We knew all the moving parts of women. We knew exactly what was happening to our bodies. We knew about sperm count. About shaven pussies. We'd studied tables and graphs published on the internet that showed the range of sizes of the human penis. We'd compared the slow but steady progress of our respective penile growth to those tables. We'd seen a hundred movies that demonstrated just about every sexual coupling imaginable. We knew it all.

But until the testosterone starts to flow that's all it is. Theoretical. But then it's not! It's all encompassing as soon as that sexual chemical tap is turned on. An emotional whirlwind that you find you have no way to control. Your thinking brain suddenly becomes trumped by the small reptilian brain that lies deep in the heart of it. A brain that sends blood rushing into your cock at the first sniff of a woman.

But of course neither of us had any ability to communicate with members of the opposite sex. None at all! Our supposed brilliant minds, minds that had easily delivered SAT scores in the top percentile, turned to mush the second an attractive female came within twenty feet of us. Womanless, we became serial masturbators and wet dreamers. Big cocked horny nerds who used their hands as sorry imitations of the real thing.

And so, in desperation, one rainy Friday night in late April, as we had sat commiserating with each other over another dateless weekend, we'd decided that we had to make an action plan. That if we didn't want to be losers the rest of our lives we'd better do something about it.

The first thing we'd done was simply write off the rest of our senior high school year. We knew there was no way to undo the previous four years. Instead we decided to use the four months we had left preparing for the fall and our new lives in faraway Princeton. Where nobody would know us or our high school reputations and where we could start over.

But start over as what? And how does one go about changing? We spent the first few weeks doing research and almost immediately found our first nugget of hope. Our problem turned out to be not that unusual. It turned out to be not only a common affliction but also one that a hell of a lot of men had written about later in their lives.

Again and again we found bios of successful men that reported that they'd suffered through their high school years only to be saved by somehow transforming themselves before they'd arrived at college. But that was the key that they all reported - the first few weeks of your university years offered a door of opportunity that might never reappear. Fuck those weeks up and you were probably fucked for the next four years. Initial impressions were damn hard to change.

So we read what other men had done. And how they'd done it. We found a hundred different suggestions that over the ensuing weeks we tried to distill into a coherent action plan. We finally boiled it down to three jobs:

1) Make an "Honest Assessment" of yourself.

2) Set "Attainable Goals".

3) Write an "Action Plan".

And so we'd both tried. I can tell you that it's not that easy. You're one of maybe two million male high school seniors in the country. Where do you stand in the group? What are the strengths of William Harold Sommers, an eighteen year old high school senior? I knew what I looked like but to tell you the truth had no real idea of how other people saw me.

.... There is more of this story ...

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Story tagged with:
Ma/Fa / Consensual / Heterosexual / Incest / Mother / Son / Sister / First / Pregnancy / Size /