He stopped for a second. "Did you know that Jess has an older sister, Lanie?"
"I didn't know that. What's that got to do with anything?"
"Well, it just so happens that Lanie Harper is one of Hannah's best friends. It's been freaking torture having her around my house all the time. Wait until you meet Lanie; she's like a wet dream come to life. Jess is cute, but Lanie is like...
walking sex
. I don't know how else to describe her. She's got enormous tits, and this ass...it's like she took so much that Jess got shortchanged. But I know that Jess and Lanie are as tight as sisters can be. If you treat Jess right, I guarantee it will get back to Hannah." AJ groaned in frustration as he missed on the 9.
Jeremy was warming to the idea, but it seemed a little cruel. "I don't feel right using Jess just to tease Hannah."
Again, AJ shrugged. "Hannah is a flirt and a tease, and Jess is like her in a lot of ways. I know they've both pitted guys against each other. To me, turnabout is fair play."
"Alright," Jeremy said, "let's do it." Nine ball, corner pocket.
Jeremy spent the early part of the next week setting up his plan to get Jess to go out with him. Since his first day as a transfer student, Jeremy hadn't really learned that much about her. He knew she was a gymnast and trained a lot. She didn't really have curves, but he was pretty sure you could bounce a quarter off her butt. They'd shared a couple of classes in the fall semester, but now they only had a government class together, last period.
As confident as AJ was that Jess wanted him to ask her out, Jeremy wasn't entirely convinced. He tried to project how he felt when he was around a girl he liked, such as Hannah. He remembered the stuttering and the embarrassment; he realized that this gave the girl the power. He wondered if he could reverse that somehow.
He decided to run an experiment to see if she would get nervous around him. So, in the one class they shared, he spent an inordinate amount of time watching her, waiting for her to look his direction. About halfway through the class, his plan came together. Mrs. Novak was droning on about the relative merits of socialist vs capitalist economies, which had just about put everyone to sleep. As Jeremy watched, Jess gave a big yawn and stretch, and then started looking around the room. He was prepared when her eyes met his; he was staring at her with a knowing smile on his face. Just as she gave him a return smile, he winked. It was subtle, but noticeable, how her eyes enlarged. Her head snapped forward, and as he continued watching her, he could see a little color creeping up her neck and at the tips of her ears. It was kind of cute. She didn't look his direction for the rest of the period, and she seemed in a hurry as she gathered her things to leave.
Jeremy considered his test a huge success, so he felt better about asking her out. Even though he'd had "girlfriends" before, this felt different. He thought maybe he ought to rely on a little better advice than that of his equally-inexperienced friends on how to get things moving. That night, he approached his dad and asked to talk with him. Normally his dad gave him pretty good advice; this time he laughed and pulled out his wallet, pressed some cash into Jeremy's hand and told him to man up. All in all, it wasn't particularly helpful, but at least he wasn't paying for the date now.
The next day, he caught up to Jess walking with her friends after lunch and called her name to get her attention. Despite rehearsing this moment, his throat was so tight and dry he could barely talk. "Jess?" He vaguely approximated her name, but it probably sounded more like an off-key trumpet. Her girlfriends were snickering and Jeremy was about to call the whole thing off, but Jess shushed her friends. It was just the relief he needed. Clearing his throat, he took a deep breath and said, "I was wondering, if you're not busy, if you'd like to go to a movie with me on Friday?"
"It's about time you asked me out. I've been waiting since the first day you walked into Mrs. Walker's class. Yes, I'd love to catch a movie with you." They talked for a few minutes and made plans. Just before she left, she pulled his head down and kissed his cheek. He couldn't believe it! He just stared at her, and she gave him a big smile, winked, and hurried off to rejoin her friends.
It was such a relief, he floated through the afternoon. In fact, he was still floating when he walked in the door at home. His mother took one look at his face, smiled, and asked, "What's her name?" When he told her the story, she laughed at the part where his voice broke, but told him that it was a rite of passage and she was proud of him. One thing still confused him, though, so he asked. "Mom, when I asked Jess out, she said she'd been waiting for me to ask her out forever. How was I supposed to know?"
His mother said, "I'm going to share a little secret with you. If you can grasp it, it'll give you an advantage over all the other guys. Here it is:
A lot of times you won't know
. Every girl is different. Some will be super aggressive and ask you out if they're interested, and others will flirt with you so obviously that you can't help but know. But for a lot of girls, the game is almost as important as the date. They want you to notice them, to pay enough attention to see subtle hints they're dropping, to pursue them. They can't even articulate it at your age, but what they really want is for you to show them your passion. If you asked them now they'd deny it, because they don't understand, but in her heart the average girl stores up fuel for a fire and is just waiting for a man to bring enough heat to set it aflame. If it was me, I'd have waited however long it took for you to build up to show me your passion. It just wasn't meant to be if that spark never arrives." Then she chuckled and said, "That's a lot of power, so use it wisely. But my advice is to practice with Jess. Something tells me she's a little different than your previous girlfriends and it probably won't last forever, but it might set the tone for all the other girlfriends you find down the road."
Jeremy thanked his mother and retired to his room to contemplate her advice. Because he really wanted this date to go right, later that evening, he again approached his dad.
"Jeremy my boy, don't overthink it. Your mom told me what she told you, and that's good advice for sure. It doesn't sound like she really gave you any clues on how to express your passion, though. In my experience, there are two things that impress girls more than anything else: self-confidence, and the ability to make them laugh. When you tell a joke to a girl on a date, so long as it's not a dirty joke that embarrasses her, she's going to see that you want her to have a good time, that you're paying attention to her, that you remember things she's said or her opinions, and that you're confident enough to let her see behind the tough-guy image that all us knuckle-draggers maintain. Don't force it and tell a bunch of jokes just to get them into the conversation. Don't be an arrogant, conceited jerk. Just relax, be yourself, and you'll know when the timing is right. Keep in mind, there's a reason that she's on a date with you in the first place. Oh, and two more things: don't show up to a first date late or empty handed. It doesn't have to be much, but it does have to be something that lets her know you've been thinking about her."
Between his Mom's and Dad's advice, he felt as prepared as he could be. Friday evening, he stopped by a flower shop on the way to pick up Jess. His intention was to bring her a red rose, because a) he didn't know much about flowers and b) everyone knows girls like roses. But then he saw something called a peppermint carnation, and was awed. He'd never seen one before; the silky white petals streaked with red really were reminiscent of peppermint candies. They were a little cheaper than the roses, so he decided to get three and headed over to meet his date.
In his paranoia about not finding the address and being late, Jeremy had left the house with lots of time to spare. Fortunately, he had no trouble finding her house. But that meant he was a good 20 minutes ahead of schedule. He considered driving around the block a few times; instead, he decided to see if Jess was running early too.
He checked his look in the side mirror, and then headed for the house. He knocked on the door, and heard footsteps approaching. As the door opened, Jeremy was met by an older version of Jess.
"You must be Jeremy! Welcome, come on in. I'm Jess's mom, Tracy." She smiled warmly and swung the door open wide. "You're a little early and she's not quite ready. Why don't you have a seat and I'll bring you some lemonade? Lanie, dear, would you take Jeremy into the living room?"
He turned and immediately understood exactly what AJ had been talking about. Lanie still lived at home while taking classes at the community college. She must have taken after her father's side, because she was not the tight-bodied pixie-like creature her mother and sister were. She was taller, for one, but also had an exaggerated set of womanly curves. To a teenage boy, it's difficult to gage the differences between one set of tits and another, what with hormones making him just want any tits to play with, but Lanie was truly exceptional. Her boobs were easily the largest that he'd ever seen on a real, live girl. Her t-shirt was trying its best to provide some semblance of modesty, but it was losing the fight. Every movement, every breath was a calculated risk of exposure, as far as Jeremy was concerned.
As she turned and led him to the living room, Jeremy was having an internal debate about whether her tits or ass were her best feature. His cock told him that it was a moot point and to just enjoy the show. Whether intentionally or caused by the volume of her bust, she had a sway in her walk that Jeremy found sexy as hell. Suddenly, he was very uncomfortable and needed a distraction before anyone noticed the swelling in his pants.
As he sank into an awkward position on the coach, Lanie sat in a rocker across from him with her legs tucked beneath her. She hadn't said anything so far, and she didn't start then. With her hair pulled back into a ponytail, he could see that she had dark green eyes that were fixed on him with a look he couldn't quite decipher. Even though they'd only been there for a minute, he was already trying to adjust his seating position. He would have sworn there was a bit of a twinkle in Lanie's eyes and the ghost of a smile playing on her lips, like she was enjoying his nervousness. Just at the point when the silence would be awkward, Mrs. Harper returned with the lemonade and a plate of cookies.
"So, Jeremy, what's on the agenda for tonight?" she asked.
