"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.

I was six foot, one inch tall that spring and at just under one hundred and seventy pounds I felt myself too thin. Neither Kevin nor I had played organized sports much growing up but I'd swum a lot in the summers. I wasn't in terrible shape.

My hair was a mess – even I recognized that the long, matted, usually uncombed nest of hair that lived on my head and tumbled down onto my shoulders wasn't anywhere close to being in style.

Kevin and I weren't great dressers! To say the least. No shots of us were going to appear in GQ. Hoodies and jeans were our norm.

My cock was largish – I'd measured it enough over the previous couple of years and then compared it 'cock size' numbers I'd found on the internet to know that. In fact it could more fairly be described as very big. So that was an asset but how do you translate that into sexual success if no one will talk to you?

And after you've finished with outward appearance you get to the hard stuff. Why can't you talk to girls? Why do you get so nervous? How do you improve? Where do you learn about kissing?

In the end we finally boiled it down to the following three categories (and subcategories) we'd have to concentrate on. Later we'd penciled in various suggestions on how to do it.

A) Improve our appearance.

1 Body – weightlift? muscles? posture

2 Clothes – Ashley knows about clothes. will she help? cost?

3 Hair -

B) Communication skills – Learn to talk to girls. how?

C) Sexual Techniques

1 Learn to dance – hire a professional? from where? Natalie from strip club?

2 Kissing – who could teach us?

3 Touching, arousing - study sex manuals? practical experience?

4 Lose our virginity – professional call girl?

So we sorta knew what areas we had to attack. We had a starting point. Mind you we weren't that confident of success. But it was better than nothing.

We bought a set of weights and set them up in Kev's basement the day after we'd finalized our plan. Every afternoon thereafter we'd gone down and lifted.

Our second step was to convince my sister to help. Fixing our appearance seemed vital.

2 - Early June 2010 Ashley

"You asked them what?" my sister asked. I could hear that she was pissed off that I hadn't asked her first. I'd hoped she would be.

"You're my sister. Besides I know you're way, way too busy for something like this."

"And they're not?"

I'd caught my sister's two best friends, Caitlyn and Brianna, like her, high school sophomores, alone earlier that afternoon and had asked them to help me. It was an important step in the detailed plan we'd worked out for the transformation of Kevin and I from nerdish, high school social misfits into suave, desirable, sexy college freshmen. Don't they say that clothes make the man?

"Do you think they know more about clothes than I do?" Sis was reacting exactly as I'd surmised. She was vital to the plan and not only because she had a better sense of style than any other girl in the school. It was also vital because we needed her salesmanship to convince our parents to finance the transformation.

I'd known we needed her one hundred percent onside and I'd finally decided that the oblique approach just might work best. Which was why I'd started by approaching her friends first.

Ashley Sommers, sixteen and only a sophomore, my sister, was the most popular girl in the school. And even though she was smart and beautiful, it was her personality that was her greatest selling point. A cheerleader and A student, there had been serious rumblings that spring that she, only going into her junior year, should run for student council president. She's eventually politely demurred but almost everyone thought she would have won if she'd tried.

I'd heard it opined more than once over the years that it was incredible that a girl like her was related to someone as socially incompetent as I. Someone had even asked me once if I'd been adopted.

"It wouldn't be fair to you ... you're too busy Ash. Besides you don't want to spend your time dressing me."

"Gawd, I wish you'd asked me a year ago. You ... you and Kevin look like--" She didn't finish her sentence. But I knew what she was thinking. Having an older brother around who dressed like a bum couldn't have been pleasant for any teenage high school girl.

"I know I'm not the best dresser—"

"You're the about the wor--" she started to say but then stopped before finishing, her inherent niceness not allowing her to finish.

"I just thought I should try to start on a better footing at College. I was looking at the Princeton site the other day and there weren't many students who dressed like--"

"Thank god for that," my sister interrupted as she raised her eyes to the sky. "Now let's go look at your clothes." My sister, when properly motivated, was a take charge kind of person.

"You'll help me?"

"Of course I'll help you, I'm your sister aren't I?" she answered, an answer that was voiced in a teenage girls exasperated tone. "Now c'mon," she ordered as she pulled me down the hall towards my room.

"Shouldn't we wait for Brianna and Caitlyn?"

"No! I'll do the preliminary scouting today and then tomorrow after school the five of us will have a council of war." Ashley was definitely going to be in charge!

"We will?"

"Yes, and tell Kevin he better be there too. No, I'll tell him myself," she said ominously as she marched past me into my bedroom. Which was pretty messy. It always was but that day I'd made it especially so. Ashley's head had already started shaking back and forth in dismay before she was half way across the room. I simply waited silently in the doorway as she started her inspection.

She opened my cupboard door first. She moved a few hangers back and forth before she slowly backed away. She was still shaking her head. Then she started in on my chest of drawers. Rifled through my t-shirts and sweaters and socks and hoodies before she finally got to my underwear.

"Well," I finally asked, "do you think that at least we have a good base to start from? That you'll be able to come up with something?"

"Yes Will, it's going to be sooooo easy."

I was smiling inside but successfully hid it when I asked back in my most dubious tone, "It will be?"

"Yes my dear Will," and now I heard the sarcasm, something my sweet sister wasn't known for, "once the bonfire has died down we will then proceed to--"

"Bonfire?" I was laughing inside now!

"Do you think that there's one piece of cloth in this sad excuse for a room that should be transported over five hundred miles to one of America's finest institutions of higher learning?"Ashley was firing on all cylinders now!

"What about my sweatshirts?"

"Hoodies," she started, and before continuing she kicked the one I'd purposely left in the middle of my bedroom floor, "are not a fashion statement."

"At least my underwear's okay isn't it?"

"Well it might Will, it might be if said undergarments weren't full of holes and of a sickly gray color." Again I'd cleverly left my worst two pairs of underpants on top of the pile in the drawer. Ones that I'd been planning to throw out.

"Now let's go over to Kevin's," she ordered as she swept back by me and out into the hall. I scurried after.

"Kevin's? Today? We're already finished here? Don't you have to make a list or something?"

Ashley simply continued on her way without answering. I pumped my fist in the air as I rushed after her.

As we walked out the door I asked to her back, "How much do you think I'm going to have to spend anyway? As much as five hundred bucks?" It was another question I'd prepared for my sister. It brought her to a sudden halt.

"Are you on drugs?"

"Less than that then?" I said hopefully.

"I'll never understand how you got accepted into a university of that caliber." Ashley's sarcasm was gone, replaced now by the sad acceptance that her brother was hopeless.

"More?"

"Will, to even get you to the minimum, the very minimum required," and here Ashley's voice emphasized the word minimum, "will cost at least ten thousand dollars and probably cost closer to twenty."

I put my most shocked look on my face. "Twentyyyyyyy thousand?" I screeched. "You're nuts."

For seconds my sister stared at me, her disbelief of her brother's ignorance unhidden. I said nothing. Finally, slowly, her expression turned from hopelessness to determination.

"What do you think I spend on clothes every year," she finally asked.

I pretended to think it over before answering. "A thousand?" I finally offered tentatively. Ashley shook her head. "Higher?" She nodded yes. "Two?" Ash pointed here finger upwards. "Not as much as three?" the finger stayed pointed up. I jumped to five thousand with my next guess. Her finger stayed pointing up.

"That's impossible, no one spends that much."

Exasperation bloomed back into sis's face. "How much do you think these shoes cost?"

I pretended to examine them. "Forty bucks."

"Over two hundred," sis answered. "And my skirt?"

I pretended I knew something about skirts and quickly answered, "I know they're about twenty-five," I said confidently, "I saw one just like that in Target last week."

"You did not see one like this in Target!" Sis's gnashing of her teeth made her hard to understand. "And what about my underwear?" she finally spat out.

"Like your bra and panties?" She nodded yes. "Well I got a six pack of Fruit of the Loom for seven dollars last month. So maybe double that if you include the bra ... so what, fourteen bucks divided by six, probably two, two dollars fifty for both."

From the look on her face I knew the plan was working. Slowly, her frustration clear, she spoke, "THE ... BRA ... AND ... PANTIES ... I'M ... WEARING ... COST ... OVER ... SEVENTY ... DOLLARS." If anyone had been within fifty yards of us they would have heard her.

"No way! That's nuts," I said, then turned and started towards Kevin's.

"THEY DO!" she yelled at my back as she started after me. I turned and waited.

"Really?"

"Yes."

"But how can they afford you? How'll they ever be able to afford twenty thousand for me?"

"Do you know how much your father makes as a lawyer every year?" I did but wasn't going to tell her. "Or what mom makes as a University Professor? Do you know what Dad pays for one of his suits?"

""Two, three hundred?"

"Twelve hundred minimum. And he has over twenty. And he has ten pairs of dress shoes.

And they're worth at least two hundred each." Ash was on a roll again. "Do you know what silk ties cost?"

"But still, you wouldn't spend all that money for a guy going to college would you?"

"Do you honestly believe your parents want you to be wandering around Princeton, New Jersey, dressed like a bum and wearing underwear that cost you one dollar a pair?"

"But what about Kevin?" I asked as we turned onto his front walk.

"He lives in a house worth almost a million dollars. His dad's Vice-President of Marketing for a Fortune 500 company." I didn't know how Ashley knew these things but she did.

Mrs. White was always delighted to see my sister. Since neither Kevin nor I had ever brought females around the White's house, Ashley, and her friends, whenever available, had always been welcomed. And my sister had always showed every sign of being as delighted to see Kevin's mother as she was to see her. And so, they spent the next ten minutes together in the kitchen, discussing everything under the sun but the matter at hand while I looked on silently. Female talk. Completely incomprehensible.

After Ashley had finished a piece of chocolate cake and a glass of milk, an offering I'd refused, she announced the purpose of her trip. "I've been retained by Kevin and my brother to assess their wardrobes in light of their impending relocation to university life. To evaluate their present holdings and jettison that which isn't appropriate and recommend what they're going to need to buy. Brianna and Caitlyn are going to help me."

It took a second or two for Kevin's mom to decipher Ashley's words but as soon as she did her face lit up. "Oh Ashley, I've tried to get Kevin out to the clothing stores for months, he and your brother are impossible."

"Most of Will's underwear has holes in it," my sister confided.

"And those awful things with hoods," Mrs. White said with a grimace.

"We're really going to need your help Mrs. White," sis implored. I knew I'd won! Leaving the two women to conspire together I wandered up to my pal's room. Mind you I didn't warn him of the coming visit. They rolled through it ten minutes later. Kevin's wardrobe was as harshly panned as mine had been.

Ashley and I of course were invited to join the Whites for dinner that night. In a concerted, clearly planned effort, my sister and Mrs. White dominated the conversation with a critique of the wardrobes of Kevin and yours truly. By the end of the meal they'd also obtained a carte blanche from Mr. White to spend all that was needed to ensure that his son would be as well dressed as any student at Princeton. He seemed amused by the whole thing.

Later, after sis and I had arrived home, Ashley disappeared into the den where mom and dad were reading. Five minutes later the three marched into my room. Ashley led them around, holding up various items for them to see as she moved from drawer to cupboard. I had to suffer hearing her running commentary on my complete lack of fashion sense for the third time that day. She also made it clear that my parents had to shoulder a large portion of the blame.

"It's bad enough in high school dad, but do you want Will wandering around one of America's greatest universities, a place where he's supposed to make business and social contacts for life, in ten dollar blue jeans with holes in the knee and a stained orange hoodie?" she asked as she held up the offending garment.

Dad, shaking his head, clearly didn't.

"Would you have even gone out with dad if he'd been dressed like that mother?" She asked my mom.

When Ashley finally led dad away to work up a 'Will going to college clothing budget' mom stayed behind. She actually apologized for her inattentiveness even as she lectured me on the horrid state of my clothes.

3 - My Mother

Ashley had inherited her beauty from my mom. Laura Cummings had been an eighteen year coed when she'd met dad, who was a first year law student and four years older than her, at a frat party during October of her frosh year.

According to the oft repeated family history, my father took about two minutes to fall in love. Mom lasted until Thanksgiving weekend when she took him home to meet her parents. Like Kevin, I too was growing in my mother's belly when my grandfather walked his daughter down the aisle eight months later.

When Kevin and I had sat down and started our planning for our 'rebirth' one of the first tasks we'd posed ourselves was to, 'list in order of preference, the 20 best looking women you know (and who you'd most like to have sex with)'.

But before we'd actually sat down and made our individual lists we'd talked about the characteristics we'd like in our preferred sexual partners. To be honest we started out pretty hopelessly given neither of us had been on a date before or even knew that many girls to even talk to.

So our points of reference were few and far between. Movie stars. Porn stars. Some rock singers. Girls in our class. Teachers. Our mothers. My sister and her friends. And when we made our lists neither of us was able to even get up to twenty.

By the end of the process my mother ended up thirteenth on Kevin's list. Ashley ended up tenth. I knew they would have ended up much higher if he hadn't been embarrassed to have my family members on his list. He didn't list his mom. At least not on his official list.

His mother was number nine on my list. Behind our schools head cheerleader, Lady Gaga, and a movie actress among others. Neither my sister nor my mom appeared on my official list although I did list Ashley's friend Caitlyn number ten.

However, on my secret list, the list I never showed Kevin, his mother was number one, my mother number two and Ashley number four. Which I knew was a bit strange. Which is why I hadn't shown it to him.

And so, when my mom had sat down next to me on my bed after dad and Ashley had disappeared to organize the financial end of the deal, I had already begun to consider her as something else besides a mom. I'd become aware of her breasts. Of her lips. Of her long, silky hair. I'd also, and again I'd never told Kevin this, rummaged through my mom's underwear. Her bras. Her panties. I'd done things with said panties ... bad things while they were wrapped around my cock...

"I probably don't really need all those clothes," I started.

"Of course you do darling," my mother said as she put an arm around me.

"You shouldn't have to pay for me."

"Ashley's right, I never should have let it get this far. Your clothes are an embarrassment. To all of us."

"I can use some of the money I've saved," I offered.

"You will not use one cent of your money." It was delivered in a tone that brooked no argument.

"It'll probably just be a waste anyway. I'm a loser." I'd decided to play the pity card.

"Yeah, like losers get accepted into Princeton," my mother scoffed. I knew my mom, a Professor of Philosophy at our state university, wasn't going to be easily swayed by whining. Still, I figured I'd try a little.

"I can't even get a date. Look at me."

"You're handsome," she protested.

"I'm hopeless."

"It'll be different when you get to university," mom promised, then added, "Ashley's so right about the clothes though, I should have thought of it before." Ashley was getting the credit for my plan.

"I can't even open my mouth when a girl gets within ten feet of me."

Mom laughed but as she did she put her arm around me. "Boys are always slower. You should see my first year classes. For the first two months I can't get a boy to say a word."

"You can't?"

"Then I can't get them to shut up."

"Did you like university? Were you scared when you left home?"

"Everyone is honey," she answered as she tousled my hair. "You'll love it. They'll be the best years of your life."

"Maybe," I said dubiously.

"You're becoming a handsome young man Will," mom said as she lifted the hair falling over my forehead and combed it back with her hand.

"Yeah right."

"You are you know. It's sneaking up on you."

"It's not sneaking up very fast," I complained. But I said it with a smile.

"You know, you're even better looking that your daddy was when I met him."

"No way."

"Uh huh. Taller. Cuter. They'll be falling at your feet the second you get to Princeton."

"Even if they do I won't know what to do with them."

"You know Will, I have a sneaking suspicion you're going to know exactly what to do with them." Mom then leaned over, gave me a quick motherly kiss on my lips and then was up and gone.

I dreamt of mom that night. She was naked. She was crying out my name in ecstasy as my penis spurted inside her.

The idea had been slowly growing in my mind since we'd made our action plan – who better than mom and Mrs. White to teach us about sex? Would it be so wrong to lose our virginity to the two women who loved us most?

5 -The Girls: Shopping for Clothes