"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 i****t?"
"It won't be i****t 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 c***d 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.
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?" s*s 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 d**gs?"
"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 s*s's face. "How much do you think these shoes cost?"
I pretended to examine them. "Forty bucks."
"Over two hundred," s*s 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!" s*s'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, f******n 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," s*s 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 s*s 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.
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?
The Girls: Shopping for Clothes
My sister was not one to sit on her heels. At four o'clock the next afternoon she, Brianna and Caitlyn were sitting on our living room couch. All three had legal pads dangling on their knees and a pen in hand. Two measuring tapes sat on the coffee table before them. On top of about twenty men's fashion magazines. All three had serious, 'I'm all business' looks on their faces.
Kevin's and my mom were hovering in the background. Meanwhile he and I were standing uncomfortably in front of them. We were both starting to regret our plan.
"We'll have to get your measurements first," my sister announced to the room. "Take off your shirts," she ordered.
"Our shirts?" Kev asked. Ashley ignored him as she handed Brianna one of the tape measures and Caitlyn the other. A minute later, two shirtless eighteen year olds were standing embarrassed in front of the eyes of five women. We were both slouching.
"Stand up straight, chest out, stomach in, shoulders back," my sister ordered. She was not to be trifled with.
"They're not that bad," Caitlyn suddenly announced from her seat on the couch. Both Kev and I looked up. "Their bodies, I mean."
"Have you guys been working out?" Bri demanded as she put the tape around my chest.
"Kevin bought some weights two months ago," Mrs. White chirped in from the back. "He and Will have been down in our basement just about every afternoon."
"Ma," Kev complained. We'd never really told anyone when we'd started our transformation. I was still thin but I had gained six pounds since we'd started.
"Forty-one inches, that's not so bad," Bri said as she lowered the tape down from my chest until it was around my waist. "And look, Will's even got biceps."
"So does Kevin," Caitlyn echoed.
For the next ten minutes Kevin and I were subjected to continuous poking and prodding while five females kept up a running commentary on the state of our bodies. In a way it wasn't much fun. But in another it was pretty darn exciting. It was the closest the two of us had been to members of the opposite sex in our lives. My cock actually woke up and looked around.
And surprisingly to Kev and I, the consensus when it was all over seemed to be that we were much better than expected.
Caitlyn then took a series of pictures. "We need them for reference purposes, when we're checking the fashion magazines, the internet sites," Ash instructed before I could raise a protest.
We were then dismissed, told that the five of them were going to spend the next two or three days preparing a shopping list. It was obvious to both of us that all the women were enjoying the process -- a chance to spend twenty or thirty thousand on a shopping spree, even if it wasn't on themselves, was clearly going to be the highlight of their year.
Later, alone in my room, Kevin said, "They didn't seem to think us that bad. Do you think they were putting us on?"
"Maybe we're not as bad as we thought we were," I answered. First mom had given me a compliment, now Ashley and her friends had, I thought to myself. It made me feel good. I didn't know it then but I do now - no matter how good a plan you have, if you don't get positive feedback you'll never effect change. Mom and Ash's words were as important as the clothes we were going to buy.
"You know Kev, I think your mom was checking me out."
"Bullshit," my best pal answered.
We had been instructed to be ready at ten a.m. on the dot on the following Saturday morning. We were. Surprisingly, Mr. White offered himself as our chauffeur. "I just gotta see this," he said with a smile as he jumped behind the wheel of his wife's Mercedes SUV.
We weren't led to K-Mart. Or Target. Or even J.C. Penny's. Frankly I would have happy in any of those places. But not the girls! Nor the mothers. They had assumed responsibility for the finished product and none of them were prepared to accept anything less than producing the best dressed college freshman of the class of 2011. It had become their mission. All five of the women had pages of notes and cutouts from every male fashion magazine ever produced. They were in shoppers heaven.
From a short term standpoint it turned into one of the worst days of my life. Fifteen different stores. At least. A hundred trips to the dressing room. Clothes that looked perfectly good to my eyes rejected ruthlessly. More changes. Endless discussions about stripes versus solids, checks versus who knows what, wool versus cashmere versus linen. Who knew?
About which color of shirt would go best with my eyes. Silk socks or whatever. We were even forced to suffer the indignity of having five women hold up different styles of underwear and discuss their relative merits. Kev and I were too embarrassed to argue. Mr. White didn't stop grinning the whole day.
The women should have driven the clothing salesmen at the stores we visited crazy but in fact the opposite happened. They were delighted to be able to discuss every aspect of male clothing with people who were clearly interested. To a man they ignored Kev and I. And my sister charmed them even as she negotiated lower prices on every item she bought.
At one store, the last one we visited, perhaps our cities most elegant male haberdashery, a store we'd spend almost two hours in, Ashley, with dad's and Mr. White's credit cards in hand, had softly and sweetly insisted on a twenty percent discount on the eleven thousand, two hundred and seventy-three dollars the owner had just rung up. He stared at my sister for about thirty seconds before capitulating, his, "of course Miss Sommers," stunning us all.
Mr. White, a man who'd been a professional salesman and a manager of salesmen at the highest levels all his life actually stood with mouth agape. Then he offered Ashley a job as a summer internship on the ride home.
"I'm going to leadership camp in July sir, with mom, a mother-daughter camp," she replied sweetly. "And then in August I'll be at Caitlyn's cottage for two weeks and after that--"
Bedraggled and beaten Kev and I were finally released some eight hours after our trek had started. But even as we stumbled towards my room, Ashley announced one final order "You're scheduled at the Salon de Paris at four Tuesday afternoon."
I trudged on, hoping that ignoring Ashley would make her go away. Not Kevin. "What Salon?" he asked.
"Renee's agreed to do you Kevin and Monsieur Pierre's doing Will."
Kevin had no idea what Ash was talking about. I guessed but continued to trudge up the stairs. Looking back when I reached the top I saw Kev surrounded by the five women. Brianna had her hands in his long hair and the others all seemed to be talking to him at once.
"We're having our hair cut at some women's hair salon," Kev announced when he arrived in my room five minutes later. He looked beaten.
"I know."
"They were talking about dyes ... and gels ... and other things," he muttered. "We have to do something." Yeah right!
The girls escorted us to the Salon three days later. The two moms tagged along. Mr. White, clearly knowing when enough was enough, wisely chose not to come.
We both had our hair shampooed. Which wasn't that bad given the fact that the two girls who did it were way cute. And of course neither of us had ever had a girl run her hands through our hair before. Other things were done to our heads. I'm not exactly sure what. At one point, while Monsieur Pierre stood poised with scissors in hand, our five ladies, plus three shampoo girls, two dyers, four cutters and six other customers, spent ten minutes discussing what exactly should be done to my hair. It was humiliating.
Unfortunately we had to go to school the next day. Neither of us had worn any of our new clothes on the Monday and Tuesday. Ashley had insisted that we wait until our hair was properly prepared before we trotted out our new duds.
Wednesday, the second last day of our high school career, was brutal. Why hadn't we waited to do all this after school had closed for the year I'd continually asked myself all that morning. A thousand whispered comments, pointed fingers, giggles, smirks, etc., etc. almost drove me home by third period. The only thing that saved us was that Ashley somehow orchestrated things so that a steady stream of girls, mainly sophomores and juniors, just happened to stop at our cafeteria table at lunch time and glowingly compliment us on our 'new looks'.
I knew of course it was Ashley and her friends work but you know what? It felt great! It's surprising how just a few words of compliments can change your view of the world.
Thursday Night Mrs. White's Negligee
"Are you staying over tonight Will?" I heard asked by Kev's mother. She was standing in her son's doorway when I looked up from my computer. I clicked away from the screen I was working on - I definitely didn't want to Mrs. W to see what I'd been doing.
"If it's okay." I answered. Of course it was okay. Kev and I had been staying over at each other's houses since we'd been like five years old. I had my own bed at his place and he had the same at mine.
"Your mom knows?" That was the one rule. Let the mothers know.
"Uh huh," I agreed. She turned to go. "We're going to watch a movie later Mrs. W, maybe in a half an hour if you want to join us," I offered. Kev looked up from his computer screen, a question in his eyes.
"You boys don't want me there. It's pretty late." Shyly said, yet clearly hoping to be argued with. Mr. White was out of town again on another of his never ending business trips and I knew she'd love to have some company.
"Of course we do. And there's no school tomorrow so it doesn't matter how late we stay up."
"Really? You're sure? Kev?" Offer accepted!
"It'll probably be thirty minutes before we're ready."
"In the playroom?" I nodded yes. "I'll have time for a bath then. I won't be late," the number one most desired woman on my list announced before scurrying away.
"What movie?" Kev asked after his mom had left.
"Kevin, it's time to move on to some of the other parts of the plan."
"What's mom got to do with it?"
"You know exactly what I'm talking about," I answered as I pulled my t-shirt over my head. "I'm going to go grab a quick shower, get cleaned up," I added, then turned my computer screen toward him and then walked out of the room.
"What's this? Are you crazy?" he asked to my departing back. I'd figured the picture of his mom, or her face anyway, a face I'd just spent the last half hour on, photoshopping it onto the nude body of a porn star, would get him going.
"What are you planning?" he demanded when I reappeared five minutes later clad only in a towel.
"Moi?" I asked as I let the towel fall. I shook my hips.
"You better not do anything," he threatened.
"Go have your shower Kev," I advised as I grabbed the bottle of after shave from the bag I'd brought with me.
"What's that?" he asked when he saw it.
"Ash and the girls recommended I use it. They said that women would like it. It acts as an aphrodisiac."
"They did? An aphrodisiac? What's that? Should I use it too?" Neither of us had ever used anything like it.
"No, Ash said this one would be better for you," I said as I dipped my hand back in my bag and came up another bottle.
"She did? Really?" he asked as he took it from me.
"Yup. And you owe me eighty-three bucks for it."
"What! Are you crazy?"
I thought we just might surprise Mrs. White with our cleaned up, showered, shaved and aphrodisiac aroma'd bodies when she arrived but it was she who instead surprised us.
I actually whistled. Kevin stood for seconds with mouth open in surprise before Mrs. White finally said, "What?"
"You look greaaaaaaaaat Mrs. W.," I said near reverentially, then whistled again.
"It's just my nighttime robe," she stammered out in reply as her face reddened. She'd definitely put on some perfume.
Ashley, or one of the girls, could give you a perfect description of what Kevin's mom was wearing that night. They'd be able to tell you what the material was (silk?), the cut, the color, the style, heck, probably the designer and its approximate price.
I can't. All I can tell you is that she looked great in it. It wasn't particularly revealing in terms of amount of skin we could see. But it was definitely sexy and anyone who saw Kev's mother in it would know without question that it was saved for special occasions.
It was some sort of Chinese kimono type robe in a shimmering, almost translucent ivory color with a subtle pattern woven in. A piece of cloth that seemed to float over her suddenly evident curves. Kevin and I had never seen her in anything remotely resembling it before. You could see her full breasts dancing under the cloth as she walked.
"You look beautiful Mrs. W.," I told her as I offered her my hand and escorted her to the couch.
When she sat down between her son and me on the playroom couch the sashed robe opened slightly and let me see that she had a matching gown under it. A negligee?
We watched a movie together. A 'chick flic' as Kevin derisively described it when it started. A tear jerker about some older babe who, a couple of years after losing her husband, goes on a vacation to Italy and has an affair with a guy twenty years younger than her. Of course I'd picked it for that very reason. Time to get Kevin's mom thinking about younger men.
It wasn't x-rated or anything but it did have a couple of pretty risqué scenes, especially when you're watching it with your mother. One was a shot of the muscular young stud from behind as he walked naked into the shower. Another showed the women topless in bed. Her tits weren't anywhere close to being as nice as Mrs. W's.
Mrs. White was excited. Don't ask me how I knew it but I did. Was it that her body was exuding those pheromone things the sex manuals are always talking about and I'd subconsciously picked up on them?
Or was it the little tremors that I felt when our legs accidently touched?
And had she noticed the almost continuous erection I had through most of the movie even though I'd tried to hide it?
With only fifteen minutes left in the movie I clicked the pause button, excusing myself to go get us some drinks. When I came back into the room I was carrying a tray with three cokes on it. I made sure Kev's mother took the right one.
***
"She's fallen asleep," Kev announced when I got back from the washroom. I'd rushed off to the pisser the second the movie had ended.
"She has?" I asked innocently.
"Do you think she's okay, I can't seem to wake her."
"It's late. She was probably just tired, maybe we better help her to her room," I suggested.
"Why, do you think something wrong with her?"
I smiled. I watched my friend and saw as realization suddenly dawned. "You didn't put something in her drink did you?"
"You get her arms, I'll get her legs," I answered as I moved over and stood between her legs.
"What was it?" Kevin asked as I put my hands under Mrs. White's legs and slowly pulled then up off the ground.
"Don't let your mom fall," I ordered as I started to pull her up off the couch and towards me. The kimono spilled open as I did and the hem of the matching nightie she wore below rode high up onto her thighs.
"We can't," Kevin said even as he grabbed his mom's shoulders.
"Michelle's wearing sexy white lace panties tonight," I told my friend as we started across the room with his mom in our arms.
"Don't call her that ... she's Mrs. White to you," he answered, trying to assert some authority even as his eyes strayed to his mom's legs. At his angle he couldn't see her panties.
"She dressed up in her sexiest panties for yours truly, I'll bet she was hoping I'd get to see them."
"She did not."
"You go first.... go backwards," I instructed as we neared the playroom door.
"Don't look at her," he ordered as, backing up, he struggled to hold his mom up. My supporting hands had moved up even farther and were now right under her bum.
I ignored him and then when he stumbled a bit I told him, "God Kev, don't touch your mother's tits!" One of his hands, slipping, had grasped his mother's breast.
"I'm not. Fuck, you should have gone first." A minute later, after struggling down the hall to the White's master bedroom, we deposited Kevin's mother in the middle of her king size bed.
"We'll have to take off her robe," I instructed as I undid the sash that held it together. "Lift her shoulders up so I can get it off."
"Do we have to? Couldn't we just--" He stopped as the outer robe slipped off his mom's shoulders and down her back. The matching nightie, once exposed, was décolleté and tightly hugged the full breasts that were clearly braless. Both of us could easily see the dark circles of her areolas and the nipples that protruded up from them. "Will, we can't--"
I ignored him.
"Nooooo." A moaning protest as he watched me slip one of the spaghetti straps of the gown off her shoulder. Then the second. Mrs. W's breasts were perfect.
"What are you going to do?" he asked as I worked the garment down over her hips. She was wearing matching lace, bikini panties. I pulled them slowly down. Mouth agape, he said nothing as I arranged his mother's hands at her sides and spread her knees slightly. Her blond bush stared up at me. He said nothing when I turned and left the room. He was still sitting in the same position on the edge of the bed next to his mom when I reappeared thirty seconds later. Except he had a huge hard on sticking out from his now undone fly. I had my digital camera in my hand.
He came out of it when I took the first picture. "She's my mom." he said. I handed him the camera.
"I want you to film me," I told him as he took the offered camera, then I scrambled up the bed between his mom's legs.
"Film what? You're not going to--"
"My first nipple," I answered as my hand closed around Michelle White's left breast. Seconds later I'd bent over her and captured her right one between my lips. For minutes I feasted on her, my sucking lips continually darting from one nipple to the other.
"She'll wake up," Kev protested in the background. I finally pulled back from the succulent orbs.
"Your turn," I offered as I cupped one of Mrs. White's breasts in my now sweaty palm and squeezed it.
"It's wrong," he protested.
"Touch it."
"No." I took his hand and placed it on his mom's tit. He groaned but he didn't let go. "It's so wrong," he said as his other hand closed on her other breast.
"Put it in your mouth, like you did when you were a baby," I encouraged as I pointed the camera and pushed the record button. He did. It had been eighteen years since he'd sucked at his mother's nipples. As his hands and mouth worked I slipped back off the bed and then quickly shucked my shorts. Then I climbed up back between them, my hard cock bobbing up against my stomach.
"She trims it," I said as my hands slipped up her inner thighs.
"Trims what?" he asked as he looked up from his mom's breast.
"Her blond bush," I said as my left hand slipped over her mound.
"Don't touch it," he ordered, watching intently as I spread the lips of his mom's sex.
"Jeeesus Kev, look at this man," I said as I bared her pink insides.
"What?" He'd forgotten her breasts. "What is it?"
"Her clitoris, look, right here," I said as I gently nudged the little bud with my finger.
"She'll wake up," he said as I dipped my head and then lightly put the tip of my tongue on her bright pink protrusion. "Are you sure that's her clit?"
"Oh fuck... oh fuck... oh fuck," I groaned into her slit as my tongue ran up and down the moist channel.
"What? What is it?"
"Look how pink she is inside. You have to taste it Kev."
"What's it like?" I moved back. A second later Kevin White's tongue was inside his mother's vagina!
"It's my turn," I ordered two minutes later, but Kev ignored me until I forcefully pulled his head back. It was my cocks turn.
"What are you going to do? You're not going to put it inside mom are you?" Kev asked as I moved in.
"Not today," I answered as I brought my straining, engorged erection right up to the now glistening lips of his mom's vagina. "I'm just introducing myself," I added as I slid my cockhead up and down her channel.
Then I pushed the middle finger of my left hand inside her . "What's it feel like?" he asked. In his excitement Kev was actually panting.
"Fuck, she's tight ... but wet ... Christ really wet Kev," I told my friend as I slipped a second finger inside.
"She is? Are they supposed to be?"
"But it's so tight. I don't think my cock will ever fit in here. Oh my gawd she just squeezed my fingers."
"She did? Let me try now, it's my turn," Kev demanded. I slowly pulled my fingers out of his mother. Then brought them to my face and smelled them. Then I held them under Kev's nose. His hand was slowly palming his cock.
I held the camera and stared filming once Kevin had positioned himself between Mrs. W's legs. Excited, he actually slipped the bulb that was his cockhead completely inside his mom. Then quickly pulled it out. Then, after looking at me, as if to get my okay, he pushed it in again.
"Push it in all the way," I encouraged. And then I filmed him as he pushed every inch of his long cock deep inside his mom. She groaned in her sleep.
"It's tight Will, it's squeezing me too," my friend groaned as he slowly pulled it all the way out.
"Do it again," I told him. He immediately obeyed. "Again," I ordered.
"Oh fuck, I'm going to cum," he stammered even before he'd bottomed out the third time.
"Jesus, take it out, don't cum in her," I ordered. The first thick creamy strand of cum exploded from the end of his penis scant milliseconds after he'd pulled out. Scrambling to his feet, and still spurting, he raced to his mother's bathroom.
When he finally came out of the bathroom minutes later he found me cock deep in his mom. I'd told myself I'd just try it out. And then, once in, I'd been afraid to move. It was better than good.
"Take it out," he told me when he saw what I was doing. Knowing that if I didn't I'd cum in her I pulled it out.
"I'm going to fuck her tits," I told my friend as my cock slipped free.
"What if she wakes?" They were just words, we were both long past any worry about his mom waking.
There are things you do in life you'll never forget no matter how long you live. Sliding my penis, still sticky with cunt juice, back and forth between Mrs. White's breasts is one of those things. I didn't last long. But it didn't matter because it felt so fucking good.
The two of us washed Kevin's mom after I'd finished. Cleaned every strand and every drop of the sperm I'd spurted out. I'd gently washed her lips, removing that last drop of cum I'd squeezed out and down onto them. And when we'd finished we replaced her panties and negligee and placed her under her sheet.
***
"Do you think we're going to go to hell?" Kevin's voice. It had echoed up from his bed a half hour later. Neither of us had fallen asleep.
"She belongs to us now Kev," I answered.
"But what about dad?"
"He's old. He's away so much. Your mother needs us."
"He can't find out," came back from Kev. It was a plea to the gods as much as instructions to me.
"They hardly ever have sex. You felt how wet she was, how ready. Even when she's sleeping."
"Still--"
"Your dad uses viagara."
"He does?" How--"
"I saw it in his medicine cabinet. He needs us as much as your mom does. If we don't do it he'll lose her to somebody else."
"But--"
"When we're at the cottage we'll do it. We're going to have more than two weeks alone with her. We're going to make her happy Kev. We're going to fuck your mom."
"At the cottage? Both of us? Without d**gging her?"
"Then when we get home, in August when your parents are in Paris, then we're going to do my mom. We've got to learn everything before we leave for school."
"I thought the plan called for us to hire call girls or prostitutes."
"It'll be better with women we love and who love us."
"But your mom and dad are ... more in love ... you're dad's younger," Kevin stammered out into the darkness.
"I think they're having problems," I answered.
Ashley Saturday
"So who are you guys taking to the prom anyway?" Looking up I saw the three girls in my doorway. It was two days after Kevin and I had d**gged his mother.
"We're not going," Kevin answered after he realized I wasn't going to say a word.
"That's stupid," Ashley announced as she stepped inside. Her friends followed.
"Especially after all the work we did," Caitlyn added.
"Yeah, what are you guys going to do? Stay home and look at dirty movies on your computers?" Brianna contributed. Then all three started to natter. Sixteen year old girls can be more than irritating. I was prepared to wait them out but Kev folded.
"We don't have dates."
"Duh! You have to ask someone, that's how it works," Caitlyn said in a voice that easily conveyed her distain for not only us but the whole of the male race.
Again Kevin couldn't refuse the bait. "It's too late. I mean who'd go with us? Everyone's already got a date. Crikey, it's next week. Everyone thinks we're losers." Ashley smiled as she heard his words, recognizing the look I knew immediately she had something up her sleeve.
"I talked to Monica today, she told me there are four or five girls that don't have dates that would love to go with you."
"Monica Evans? You talked to Monica Evans?" Kev asked. Her name certainly got our attention. Monica Evans was the head cheerleader, the best looking girl in the senior class, and the odds on favorite to be named Prom Queen. She was one of the recurring main players in both of our wet dreams.
Watching Ashley I knew that if I didn't act immediately we were going to end up going to the prom with who knew what. "Hey, you're not going Ash," I quickly interjected, trying to forestall hearing who she'd plotted to set us up with.
"Sophomores can't go to the Senior Prom Will," Caitlyn informed me.
"Unless they go with a senior," I corrected.
"Here are the names Monica gave me," Ash said, clearly trying to get back to her game plan.
"Ash could be Kevin's date," I said.
"Who can?" Brianna asked. I'd also got Kevin's attention.
Ashley immediately realized I was trying to escape her manipulations. "I have a boyfriend Will. Besides, someone going to Princeton certainly would never even consider going to his senior prom with a mere sophomore. It wouldn't be appropriate."
"I'd go with you Ash." Kev said enthusiastically. I figured my suggestion and his offer would send the girls packing in retreat.
"And what about Will?" my sister asked. She clearly wasn't ready to throw in the towel yet.
"Well, I could double date with you," I offered with a smug smile.
"If you're going to double date with us you'd need to have a date you idiot." We all probably would have laughed off the whole thing if I hadn't said what I said next. Kev and I would have escaped whatever girls Ashley had planned for us and we'd have not gone to the dance. But the troublemaker in me let it slip out.
"No, you're probably right Ash, girls your age really aren't old enough for a senior prom." Immediately the faces of all three clouded up. But before any of them could say a word, Kev, clearly inspired, and who definitely had liked the idea of dating my sister, came up with the one killer comment that sealed the deal.
"I hear Karen Miller's going, but of course she's more mature than most sophomores."
"She's what?" Caitlyn almost shrieked.
"She's a slut," Brianna said with scorn. My sister, silent, sat fuming and looked like she was going to explode. Karen Miller was Ashley's one contender for the crown of the best looking and most popular sophomore in the school.
"She's going with that jerk Billy," Ash finally hissed through gnashed teeth.
"Still," I said. I could see the decision as it formed in my sister's eyes.
"You're going to be my date Kevin," she announced.
"I am?" Kevin couldn't keep the happiness out of his voice.
"And Will, I personally am going to get you a date from this list whether you like it or not," she threatened.
"I told you I'd double date with you," I answered amicably.
"And I tried to explain that double dating would require that you acquire a date." Her words were delivered fairly aggressively.
"No, I meant I'll double date with both Brianna and Caitlyn. If they'll go with me."
"You can't take two dates to the prom."
"Why not?" I asked as I looked at Bri and Caitlyn.
And so, after arguments back and forth, it was decided. The five of us would attend the prom. Notwithstanding who their dates were, the girls, once they'd accepted, were obviously delighted.
Going to the senior prom, even if it meant going with Kev and I, was a coup.
"Now, we have a hundred things to do to organize," Ashley announced once the decision had been made.
"We do?" Kev asked. Bri and Caitlyn quickly started to list them: Hair, gown, corsages, shoes, tux, limo, nails, tickets, etc., etc.
"And we'll have to arrange getting invited to the right parties," s*s added.
"What parties?" Kevin asked. I wasn't sure I wanted to know.
"We'll tell you later, we don't have time right now," Ash answered. Seconds later the three had swept out of my room in a sea of excited chatter.
Natalie's Dance Lessens
At about ten-thirty that night Kevin called. He had one question. "Can you dance?" Fuck! Of course neither of us could.
It was however one of the items we'd highlighted on our 'get ready for Princeton' list. Item C 1: Learn to dance.
Next to that item on my master list I'd written in pencil: hire a professional? from where? Later on I'd added: Natalie from strip club?
Natalie was a sweet young girl. A sweet stripper? Yes she was. At least that was my impression from our one fleeting previous encounter. Well, it wasn't that fleeting I suppose. She'd given both Kevin and I two lap dances each when we'd visited the 'Lady Pussycat' emporium of drinks and dances some four weeks earlier. Using fake ID's, we'd talked our way into the club on one of our dateless Fridays just weeks after we'd started our planning sessions. We justified it as being an important, fact finding, part of our research.
And Natalie had talked to us the whole time she'd danced for us. Perched on a stool between first Kevin's legs and then mine she'd somehow managed to put the two nervous high schoolers at ease. And she hadn't treated us like k**s even though we quickly admitted under her questioning that we were high school seniors. And she didn't rush away the second she'd finished.
She'd just finished her second year of university. She was beautiful. First 'live' tits we'd ever seen. And could she dance! This we'd observed when she'd been up on stage. When we finally worked up enough courage to ask one of the girls to dance for us, we'd chosen her.
And so, when I'd got home from the club that night, I'd written her name on my list as a potential dance instructor.
Which was why, when I'd hung up my call with Kevin the night we'd agreed to go to the prom, I put on some jeans, grabbed my wallet and after borrowing mom's car, set out for the club. Not sure how I'd be received I decided not to tell Kev my plan.
"Hey you," she said as she sidled up to me. There was a friendly smile on her face. I figured there was no way she'd remember me.
"Will? It's Will right?" Then she ran a hand through my hair and said, "hey, your new look is cool, you look great."
"It is? I do? You remember me?"
"You're like by far the cutest guy in the club." I blushed even while wondering if this was some stripper come-on line. "I mean it," she added as she saw the question in my eyes. "You shoulda seen the last guy I had to dance for. He was like two seventy and I don't think he'd washed in a week. At least fifty years old. Garlic on his breath. Yuck!"
I had never really considered the travails of a dancer in a nude club before. "I guess you have to dance with anyone who asks you, don't you?"
"Unless a cute guy like you asks me first." She could see the momentary indecision in my eyes and so quickly added, "Please. I really need a break. I've just got to talk to someone normal. I won't even charge you," she lured as she took my hand and tried to pull me to my feet.
"In a booth?" She nodded as I followed her towards the back room. "Do you want a drink first?"I asked. She nodded her yes. "And don't worry, I'll pay for your time," I added.
Two minutes later I was sitting in a booth in the back corner of the private lap dance room. It was very dark. Natalie was perched on the stool she'd placed between my legs.
"How come you're not out with your girlfriend?" she asked between sips of her drink.
"That's sorta why I'm here?" The music started up.
"It is?" Natalie asked as she started to undo the buttons on her blouse.
"You don't have to do that," I said as my eyes darted to her cleavage.
"You don't want to see them?" Natalie asked as she undid the last button. Her blouse, hanging open, drew my eyes. Of course I wanted to see them! And she knew it.
"We're losers," I finally blurted out.
"Who are?" Natalie asked as she slowly pulled her blouse apart. Her nipples were erect.
And so I told Natalie the sad story of the life of myself and my friend Kevin. Of our dateless weekends. Of our plan to change ourselves. And as I told her the story my eyes danced back and forth between her face and her nipples.
"You're a virgin? Really?" she interrupted at one point. I nodded. "No w