We'll Do Your Mom First, Then Mine, I Told Kev
Copyright© 2010 by scouries
Chapter 2: Early June 2010 Ashley
Erotica Sex Story: Chapter 2: Early June 2010 Ashley - Two teenage boys, nerdy but horny, realize they need help if they're ever going to get anywhere with women. So they get Will's 16 yo sister and her friends to help in their transformation. But when it comes to their virginity they think first of their mothers...
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Incest Mother Son Sister First Pregnancy Size
“You asked them what?” my sister asked. I could hear that she was pissed off that I hadn’t asked her first. I’d hoped she would be.
“You’re my sister. Besides I know you’re way, way too busy for something like this.”
“And they’re not?”
I’d caught my sister’s two best friends, Caitlyn and Brianna, like her, high school sophomores, alone earlier that afternoon and had asked them to help me. It was an important step in the detailed plan we’d worked out for the transformation of Kevin and I from nerdish, high school social misfits into suave, desirable, sexy college freshmen. Don’t they say that clothes make the man?
“Do you think they know more about clothes than I do?” Sis was reacting exactly as I’d surmised. She was vital to the plan and not only because she had a better sense of style than any other girl in the school. It was also vital because we needed her salesmanship to convince our parents to finance the transformation.
I’d known we needed her one hundred percent onside and I’d finally decided that the oblique approach just might work best. Which was why I’d started by approaching her friends first.
Ashley Sommers, sixteen and only a sophomore, my sister, was the most popular girl in the school. And even though she was smart and beautiful, it was her personality that was her greatest selling point. A cheerleader and A student, there had been serious rumblings that spring that she, only going into her junior year, should run for student council president. She’s eventually politely demurred but almost everyone thought she would have won if she’d tried.
I’d heard it opined more than once over the years that it was incredible that a girl like her was related to someone as socially incompetent as I. Someone had even asked me once if I’d been adopted.
“It wouldn’t be fair to you ... you’re too busy Ash. Besides you don’t want to spend your time dressing me.”
“Gawd, I wish you’d asked me a year ago. You ... you and Kevin look like--” She didn’t finish her sentence. But I knew what she was thinking. Having an older brother around who dressed like a bum couldn’t have been pleasant for any teenage high school girl.
“I know I’m not the best dresser—”
“You’re the about the wor--” she started to say but then stopped before finishing, her inherent niceness not allowing her to finish.
“I just thought I should try to start on a better footing at College. I was looking at the Princeton site the other day and there weren’t many students who dressed like--”
“Thank god for that,” my sister interrupted as she raised her eyes to the sky. “Now let’s go look at your clothes.” My sister, when properly motivated, was a take charge kind of person.
“You’ll help me?”
“Of course I’ll help you, I’m your sister aren’t I?” she answered, an answer that was voiced in a teenage girls exasperated tone. “Now c’mon,” she ordered as she pulled me down the hall towards my room.
“Shouldn’t we wait for Brianna and Caitlyn?”
“No! I’ll do the preliminary scouting today and then tomorrow after school the five of us will have a council of war.” Ashley was definitely going to be in charge!
“We will?”
“Yes, and tell Kevin he better be there too. No, I’ll tell him myself,” she said ominously as she marched past me into my bedroom. Which was pretty messy. It always was but that day I’d made it especially so. Ashley’s head had already started shaking back and forth in dismay before she was half way across the room. I simply waited silently in the doorway as she started her inspection.
She opened my cupboard door first. She moved a few hangers back and forth before she slowly backed away. She was still shaking her head. Then she started in on my chest of drawers. Rifled through my t-shirts and sweaters and socks and hoodies before she finally got to my underwear.
“Well,” I finally asked, “do you think that at least we have a good base to start from? That you’ll be able to come up with something?”
“Yes Will, it’s going to be sooooo easy.”
I was smiling inside but successfully hid it when I asked back in my most dubious tone, “It will be?”
“Yes my dear Will,” and now I heard the sarcasm, something my sweet sister wasn’t known for, “once the bonfire has died down we will then proceed to--”
“Bonfire?” I was laughing inside now!
“Do you think that there’s one piece of cloth in this sad excuse for a room that should be transported over five hundred miles to one of America’s finest institutions of higher learning?”Ashley was firing on all cylinders now!
“What about my sweatshirts?”
“Hoodies,” she started, and before continuing she kicked the one I’d purposely left in the middle of my bedroom floor, “are not a fashion statement.”
“At least my underwear’s okay isn’t it?”
“Well it might Will, it might be if said undergarments weren’t full of holes and of a sickly gray color.” Again I’d cleverly left my worst two pairs of underpants on top of the pile in the drawer. Ones that I’d been planning to throw out.
“Now let’s go over to Kevin’s,” she ordered as she swept back by me and out into the hall. I scurried after.
“Kevin’s? Today? We’re already finished here? Don’t you have to make a list or something?”
Ashley simply continued on her way without answering. I pumped my fist in the air as I rushed after her.
As we walked out the door I asked to her back, “How much do you think I’m going to have to spend anyway? As much as five hundred bucks?” It was another question I’d prepared for my sister. It brought her to a sudden halt.
“Are you on drugs?”
“Less than that then?” I said hopefully.
“I’ll never understand how you got accepted into a university of that caliber.” Ashley’s sarcasm was gone, replaced now by the sad acceptance that her brother was hopeless.
“More?”
“Will, to even get you to the minimum, the very minimum required,” and here Ashley’s voice emphasized the word minimum, “will cost at least ten thousand dollars and probably cost closer to twenty.”
I put my most shocked look on my face. “Twentyyyyyyy thousand?” I screeched. “You’re nuts.”
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