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DOLLARS." If anyone had been within fifty yards of us they would have heard her. That's nuts," I said, then turned and started towards Kevin's. 3 - My Mother Ashley had inherited her beauty from my mom. I'd also, and again I'd never told Kevin this, rummaged through my mom's underwear. "Of course you do darling," my mother said as she put an arm around me. "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. For the first two months I can't get a boy to say a word." "You can't? She was crying out my name in ecstasy as my penis spurted inside her. "Kevin, it's time to move on to some of the other parts of the plan." "What's mom got to do with it? 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. " he demanded when I reappeared five minutes later clad only in a towel. " One of his hands, slipping, had grasped his mother's breast. 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. He was still sitting in the same position on the edge of the bed next to his mom when I reappeared thirty seconds later. For minutes I feasted on her, my sucking lips continually darting from one nipple to the other. As his hands and mouth worked I slipped back off the bed and then quickly shucked my shorts. oh fuck," I groaned into her slit as my tongue ran up and down the moist channel. "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 actually apologized for her inattentiveness even as she lectured me on the horrid state of my clothes. "I probably don't really need all those clothes," I started. I ignored him and then when he stumbled a bit I told him, "God Kev, don't touch your mother's tits! Seconds later I'd bent over her and captured her right one between my lips. "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. It had been eighteen years since he'd sucked at his mother's nipples. How'll they ever be able to afford twenty thousand for me? "Oh Ashley, I've tried to get Kevin out to the clothing stores for months, he and your b*****r are impossible." "Most of Will's underwear has holes in it," my s****r confided. White to spend all that was needed to ensure that his son would be as well dressed as any student at Princeton. Later, after sis and I had arrived home, Ashley disappeared into the den where mom and dad were reading. Ashley led them around, holding up various items for them to see as she moved from drawer to cupboard. "Michelle's wearing sexy white lace panties tonight," I told my friend as we started across the room with his mom in our arms. go backwards," I instructed as we neared the playroom door. A second later Kevin White's tongue was inside his mother's vagina! Then I pushed the middle finger of my left hand inside her. 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. By the end of the meal they'd also obtained a carte blanche from Mr. "We can't," Kevin said even as he grabbed his mom's shoulders. White to you," he answered, trying to assert some authority even as his eyes strayed to his mom's legs. "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 ... "I'm just introducing myself," I added as I slid my cockhead up and down her channel. I laughed, then blocked his view as I touched the spot he was staring at with the tip of my cock. "Okay, I'll be right back," Kev's thirty-four year old mom promised. " "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. " "That's why I'm going to let you go first." "What! 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. Who on your list do you think you'll be able to get to help us? But of course neither of us had any ability to communicate with members of the opposite sex. 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. 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. Besides you don't want to spend your time dressing me." "Gawd, I wish you'd asked me a year ago. you and Kevin look like--" She didn't finish her sentence. Having an older b*****r around who dressed like a bum couldn't have been pleasant for any teenage high school girl. "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 b*****r was hopeless. " "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. "What do you think I spend on clothes every year," she finally asked. The drop of precum that had already formed slid onto the screen. My cock started to spurt as I listened to her words. " "But when we get to my mom I'll go first." "Your mom! Womanless, we became serial masturbators and wet dreamers. Someone had even asked me once if I'd been adopted. "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. 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. "I just gotta see this," he said with a smile as he jumped behind the wheel of his wife's Mercedes SUV.
We both froze when a second later we heard a knock on his bedroom door. The first thing we'd done was simply write off the rest of our senior high school year. " she answered, an answer that was voiced in a teenage girls exasperated tone. 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! Ashley's head had already started shaking back and forth in dismay before she was half way across the room. Rifled through my t-shirts and sweaters and socks and hoodies before she finally got to my underwear. " 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! "And look, Will's even got biceps." "So does Kevin," Caitlyn echoed. It was the closest the two of us had been to members of the opposite sex in our lives. And surprisingly to Kev and I, the consensus when it was all over seemed to be that we were much better than expected. "We need them for reference purposes, when we're checking the fashion magazines, the internet sites," Ash instructed before I could raise a protest. "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. 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. "We're having our hair cut at some women's hair salon," Kev announced when he arrived in my room five minutes later. I clicked away from the screen I was working on - I definitely didn't want to Mrs. Like Kevin, I too was growing in my mother's belly when my grandfather walked his daughter down the aisle eight months later. All three had legal pads dangling on their knees and a pen in hand. 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. White, clearly knowing when enough was enough, wisely chose not to come. Which wasn't that bad given the fact that the two girls who did it were way cute. 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. Ashley had insisted that we wait until our hair was properly prepared before we trotted out our new duds. Kev looked up from his computer screen, a question in his eyes. It's pretty late." Shyly said, yet clearly hoping to be argued with. White was out of town again on another of his never ending business trips and I knew she'd love to have some company. And there's no school tomorrow so it doesn't matter how late we stay up." "Really? The matching nightie, once exposed, was décolleté and tightly hugged the full breasts that were clearly braless.
Mom lasted until Thanksgiving weekend when she took him home to meet her parents. By the end of the process my mother ended up thirteenth on Kevin's list. I knew they would have ended up much higher if he hadn't been embarrassed to have my f****y members on his list. However, on my secret list, the list I never showed Kevin, his mother was number one, my mother number two and Ashley number four. At four o'clock the next afternoon she, Brianna and Caitlyn were sitting on our living room couch. Clothes that looked perfectly good to my eyes rejected ruthlessly. Endless discussions about stripes versus solids, checks versus who knows what, wool versus cashmere versus linen. About which color of shirt would go best with my eyes. We were even f***ed to suffer the indignity of having five women hold up different styles of underwear and discuss their relative merits. 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. Neither of us had worn any of our new clothes on the Monday and Tuesday. W, maybe in a half an hour if you want to join us," I offered. Couldn't we just--" He stopped as the outer robe slipped off his mom's shoulders and down her back. "Jeeesus Kev, look at this man," I said as I bared her pink insides. We knew there was no way to undo the previous four years. You're one of maybe two million male high school seniors in the country. What are the strengths of William Harold Sommers, an eighteen year old high school senior? 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 the end we finally boiled it down to the following three categories (and subcategories) we'd have to concentrate on. "Now c'mon," she ordered as she pulled me down the hall towards my room. I simply waited silently in the doorway as she started her inspection. She moved a few hangers back and forth before she slowly backed away. "Well," I finally asked, "do you think that at least we have a good base to start from? " "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? " "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?