A Gentleman's Guide to Hookin...

By rainbowbrook

1.3M 58K 33.3K

Casual sex is harder than it seems. In order to keep it safe, both emotionally and physically, Jake comes up... More

10 r u l e s
r u l e # 2
r u l e # 3
r u l e # 4
r u l e # 5
r u l e # 6
r u l e # 7
r u l e # 8
r u l e # 9
r u l e # 10
b o n u s r u l e

r u l e # 1

205K 5.7K 4.8K
By rainbowbrook

Rule #1 Choose your partner with caution

Before we talk about the dos, let's cover the don'ts. So here goes:

Don't hook up with stupid people. Scary people. Crazy people. Your exes. Your friends' exes. Your exes' friends. People who are in relationships. People who have a thing for you. People who are emotionally unstable or can easily become too attached. People who tweet about everything. People who you see often and can't escape from. People who don't floss.

See? It's really not easy selecting a partner. So when you do find one, cherish them.

......

Every Sunday evening, Jake's father would carefully search through the reviews on Zagat, pick a restaurant, and take his family out for dinner. He was a businessman too busy to be at home on most nights, but Sundays were special and he made an effort. Although Jake and Emily acted embarrassed to be seen with their parents (they were cool kids, after all, and parents weren't cool accessories), it was something they both secretly looked forward to.

They were allowed to order anything on the menu that sparked their interest, and Jake was always ravenous when he sat down. Everything looked tempting. It wasn't until the table was covered with empty plates and he was ready to puke did he start to wonder, how on earth did I get here? It felt as if an elephant grew in his stomach and he wasn't hungry anymore. He couldn't remember ever being hungry.

That, was how it felt like when he glanced over at what's-her-name--oh yes, Ashley--who was lying naked next to him on the bed, yapping nonstop about some celebrity scandal he couldn't care less about. Jake searched his memory but couldn't remember why he was so eager to have sex with her. Now that it was over and done with, his penis softened and his heart hardened, and Ashley had quickly slid down from a ten to a...six, at most, and that is if she shut up within the next five seconds.

"Do you think I'm fat?" she asked suddenly, twirling a strand of hair around her finger.

Jake could deal with questions concerning favorite positions and hard limits, but reassuring her about her body image was something she should torture her future husband with. "No, your body is perfect."

"Really? I don't like my thighs."

"You girls are too hard on yourselves. For us guys, we can accept anything within this range." Jake spread out both of his arms. "As long as you don't fall too far from norm and land over there"--he pointed across the room--"then it's fine. But honestly, you have a wonderful body."

"Thanks." She smiled as she inspected her nails. The paint on one of them was chipped. "Hey, so, my friend Jennifer is having a party next week. You should come. I can introduce you to everyone."

"Everyone?"

"I'd love for you to meet my friends." She snuggled closer against him, and Jake involuntarily flinched. Not sure if it was because of her words or the physical contact.

"I'm kind of busy next week."

What part of 'I don't want a relationship' don't you get, Ashley? This is sex. And it's over fifteen minutes ago. You should get going.

"I haven't even told you which day it is yet." She pouted.

"Look, Ash." Jake sighed. She seemed so cool before. She even said she just got out of a long-term relationship and the idea of anything serious turned her off. "I respect you, so I have to be honest. I thought we agreed to just have a fun afternoon together and that's all I want."

"You don't have to decide right now," she replied as if they spoke different languages. "It's next Friday, so there's plenty of time to make up your mind."

Jake glanced at the time and wondered what he did wrong to deserve this. He was so careful about not sending the wrong signal. He told her she was hot instead of beautiful (beautiful carries sentimental meaning therefore is a forbidden word), he said repeatedly about how he was not the relationship type, and he even blatantly told her he wanted sex, and only the most meaningless kind.

Yet here he was, trying to get her to leave because she couldn't seem to take a hint.

"My mom is going to come back soon," he said. "So we should probably..."

"I don't mind." She leaned over him and picked up his family photo from the nightstand. She made a small sound of surprise as she looked from his mother's ebony skin to his golden hair and aquamarine eyes. "You don't look anything like your parents." Her eyes widened. "Are you adopted?"

Jake didn't know if he should be offended or laugh, so he laughed. "No. I take after my biological mom, but she left us when I was little. My dad remarried."

Ashley's eyed widened further, this time with sympathy rapidly pouring in, like filling up a bathtub. She glanced again at the photo. "So she isn't your real mom? You poor thing."

The only poor thing here is your ignorance, Jake thought, but he was nice and he didn't say things like that. He put on a patient smile. "No, she didn't give birth to me, but she is my real mom."

"You poor thing," she said again. "Is that why you can't handle a meaningful relationship? I mean, the one person who should love you left you. That must make you feel like you don't deserve to be loved or something."

Jake wondered how he could have missed all the signs. A chick this crazy would definitely exhibit certain traits beforehand, yet he was apparently so horny he was willing to overlook everything.

Under normal circumstances he wouldn't lie, but drastic times allowed for drastic measures. "Yeah, Ash. I'm seriously messed up. You should stay away from me because I'm incapable of feelings." He had to bite the inside of his cheeks to refrain from grinning. "I'm going to destroy everything around me."

This fact seemed to excite her. Instead of viewing him as a sunk ship, Ashley turned to him, a loving I'll-fix-you smile plastered as if she was seeing hidden treasures instead. With a sweet sigh, she said, "Don't give up on yourself, Jake. Let's just see where things go."

"Don't take it personally, Ash," he replied, pulling her hand away from his chest, "but it's not going anywhere."

......

Ashley wasn't the only plan gone wrong this month. There was also Stephanie, and just thinking of Stephanie made him want to smack himself on the forehead. He still wasn't sure he made the right decision with her.

They were fooling around, rubbing each other like making dough for pizza, and Jake had just taken off her bra when she blushed.

"I haven't done this before," she whispered.

"That's okay," Jake said, distracted, moving in to bury his face against her breasts. He pulled back. "Wait what?"

This can not happen. He felt like he had been slapped.

Why? Why? Part of him was relieved she told him in time, and part of him wished he never knew.

"You're a virgin?" he croaked.

She nodded once. "Does it matter?"

"It doesn't matter to me, but it's going to matter to you."

"Hey," she said softly. "I know what I'm in for. You don't need to feel responsible afterwards or anything. I just want to get it out of the way, and I want to do it with someone who knows what he's doing."

Jake wished it was as easy as that. No matter how he looked at it, it sounded like a trap. In times like these when his head up there was battling against the one down there, he could hear Angel Jake and Devil Jake talking both at once.

You can't discriminate against virgins, man, Devil Jake said with a cocky grin. He sounded strangely like his best friend Dylan. Don't deny her access to the awesome, magical, not-so-little Jake. It's her basic virginal right.

It's not worth it. Angel Jake shook his head. His voice was that of his other best friend Sean. Five seconds of pleasure is going to cause you a lifetime of regret.

Five seconds? Devil Jake/Dylan gasped. How dare you! And look, man, look! Look at those boobs. You don't say no to boobs like that. You just don't.

Jake, don't do it, the angel warned. You don't know this girl. You can't trust her. During sexual intercourse, her brain will release this chemical called oxytocin and before you know it, she'll be dragging you home to meet her parents. Quick, think of things to turn you off.

Jake was easier to turn on than a touch screen. To try turning him off, however, was significantly harder. He racked his brain for revolting images.

Defective condoms. Baby sonograms. Infected genitals. Dylan...in a pink thong.

There. All better. Jake let out a relieved breath. "Steph, you're great and everything, but I feel uncomfortable going through with this."

Disappointment fell over her face like a veil. "It's really not such a big deal. I'm attracted to you physically and I want to do it with you."

Jake had a whole speech prepared about how she should save it for someone special, how it could be a bazillion times more amazing if she was actually in love, but he didn't want to be a hypocrite. Let's face it, un-special sex can be just as amazing, and he didn't think Stephanie's intentions were all that wrong. He just didn't want to complicate things for himself should she start to have weird thoughts later.

"How about we each take a step back and we can try..." He scratched the back of his neck. "...phone sex?"

She giggled in disbelief. "Phone sex?"

"Yeah, I'll call you tonight," he promised. "I'll make it really special for you. I'll...I'll even write you a poem."

Stephanie was laughing now. "I look forward to that."

He sighed with longing as she put her clothes back on, and after she left, he watched his offspring swirl down the toilet. This wasn't what he planned, but to be fair, those two encounters were actually the better ones.

He tried not to think about his smashed windshield, the tears, the harassing texts, jealous boyfriends threatening to kill him (he really didn't know!!), and the numerous times girls had called him names just because he didn't quite meet their expectations (not during, but after). He just wanted to have a pleasant time without hurting anyone, but damn, it's so hard to come across a decent partner.

If only he could find someone who understood.

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