"We'll Do Your Mom First," I Said

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"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.

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.

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