Go Ask Your Girlfriend!

“Thank you so much, Heather,” Jimmy’s mom apologized as they stood on the porch. “I know it’s a bit unusual, but obviously, at Jimmy’s age, we couldn’t call any of his old sitters.”

“Don’t worry,” Heather reassured her. “I’m happy to keep an eye on him.”

“We’ve had these tickets for months, but Jack was talking about canceling! When Karen mentioned you were home for the summer, it seemed like a perfect fit. I remembered Jimmy and your younger brother were friends, and how you used to drive them to the mall after you got your driver’s license. You were always so responsible…” She trailed off as the shouting from inside got louder.

“This is bullshit!” Jimmy stomped down the stairs after his father. “I graduated last week. I don’t need a babysitter!”

“After the shit you pulled…” Jimmy’s dad pinched his nose and turned to face his son. “Trust is earned, kiddo. And you’ve lost ours, at least for now.”

“Ugh!” Jimmy threw his hands in the air and stormed off.

“Sorry about that, Heather,” Jimmy’s dad sighed. “He’ll calm down. Here’s some money for delivery. Make yourself at home. We’ll be back around eleven.”

“Take your time,” she smiled, tucking the cash into her hoodie pocket and waving as they climbed in the car. She closed the front door and followed the sound of banging cabinets to the kitchen, where Jimmy was rummaging for snacks.

“Trust is earned,” he muttered in a mocking tone.

“What’s up, Jimmy,” Heather said, trying to keep the amusement from her voice. She’d only been at university for two years, but these teenage dramatics already seemed like the distant past.

“Hey, Heather.” He scowled while devouring a granola bar. “He’s totally overreacting, you know. It was just a party! No reason to treat me like a child.”

“From what I heard, that party got shut down by the cops. I’m not surprised he’s pissed.”

“How’d you hear about it?”

“A few guys from my dorm told me. They came back to town that weekend for a game, heard about a party, and decided to crash it. They were like, ‘you should have seen these high school kids going buck wild!’ I mean, damn, Jimmy,” she teased, “I can’t believe the shy kid I knew from photography class threw a rager!”

“It wasn’t that wild,” he grinned, trying to play it cool, but clearly pleased by her reaction. “A couple of broken windows. Someone puked in the pool. The cops only showed up because the music was too loud.”

“I’m sure,” she laughed. “Look, man, I get this is weird, but I’m just here to make sure you don’t burn the place down or whatever. I’ll order some pizza and watch a movie. You can hang with me or do your own thing. No big deal, okay?”

“Yeah, okay,” he sighed. “Not your fault my dad’s a dick.”

---

A couple of hours later, they were sitting together on the couch, with the remains of a pizza on the coffee table. Jimmy seemed noticeably more relaxed after eating. Heather was only half paying attention to the movie. Her phone kept buzzing with messages.

“Who are you talking to?” Jimmy asked.

“A guy from school.”

“Anyone I know?”

“No,” she chuckled. “You don’t know him.”

“Are you guys dating?”

“Dating?” She raised an eyebrow. “No, we just hang out sometimes.”

“Cool,” he nodded. “Cool, cool, cool.”

A few minutes passed.

“So,” Jimmy asked with studied casualness, “what are you guys talking about?”

“Why do you want to know?”

“I mean, it’s gotta be more interesting than this weird French chick flick.”

“Hey,” she protested, “I like this movie!”

“You’ve seen it before?” He looked baffled. “Why’d you put it on?”

“It makes me happy. I like watching them fall in love.”

Jimmy rolled his eyes, but returned to the movie.

Before long, her phone buzzed again. She read the message, laughed, and typed out a reply. When she looked up, Jimmy was watching her.

“C’mon, tell me what you sent. This movie is boring and I hate subtitles.”

“It’s about to get to the best part.”

“I’m sure they’ll kiss under a rainbow or some shit. What’d you send?”

“You really want to know?”

“Yeah, tell me.”

“Fine. I said I’d give him a blow job next time I see him.”

“Oh! Uh… Cool.” Obviously flustered, he turned away. She tried not to laugh at how red he turned.

The next scene was her favorite. The leading man realized he’d been an idiot and confessed his love for the heroine. She admitted to herself that she loved him as well, and they fell into a passionate embrace.

The music swelled, and Heather smiled, imagining herself in the heroine’s place, pressing her body against his, feeling his lips on hers.

The leading man’s shirt fell to the floor, and the heroine traced her fingers over his bare chest. He removed her bra, and she gasped as he kissed her neck.

Jimmy kept glancing in Heather’s direction. She crossed her legs, suddenly aware of both how short her skirt was and how long the scene was.

The heroine moaned as the leading man lowered her onto the bed. She arched her back as he moved lower, until only his tousled hair was visible between her thighs.

Jimmy shifted awkwardly, and pulled a pillow into his lap. Heather bit her lip. She didn’t remember the movie being this explicit, and now she felt a little guilty for making that blowjob comment.

The leading man moved behind the heroine as she rolled onto her hands and knees. He thrust forward, and she cried out, gripping the sheets as they started moving together. Her breasts swayed, erect nipples dragging against the silk sheet.

Heather shivered, imagining the sensation, and crossed her arms over her chest. Jimmy met her eyes for a moment, and quickly looked away.

The heroine climaxed, calling the leading man’s name as he moaned and collapsed on top of her. They rolled into a loving kiss as the credits rolled.

“Alright,” Jimmy said calmly. “That movie was pretty good.”

They both dissolved into laughter.

“Oh man,” she said, wiping tears from her eyes. “That was a lot steamier than I remembered.”

“I see why you like it.”

“That’s not why I like it!” She threw a pillow at him, which knocked away the one in his lap. “Looks like you did, though.”

“Yeah, I, uh…” He trailed off as he followed her gaze to the rather obvious erection tenting his shorts. “Ack!” He grabbed for one of the pillows.

“At ease, Jimbo.” She winked. “No need to salute.”

“Sorry! Sorry.” His face had turned bright red with embarrassment. She felt bad for him, honestly. Teenage boys popped a boner if you looked at them funny, and she’d just made him sit next to her through a seriously hot sex scene.

Perhaps it had affected her, too, because she couldn’t help noticing Jimmy had really grown into himself. Last time she’d seen him, he was all elbows and knees, gangly as a colt. Now his shoulders were broader, and he seemed to have filled in a bit. She found herself imagining moving closer, reaching into his shorts to wrap her hand around…

“Do you, um…” She shook her head, banishing the thought. “Do you need to go take care of that?”

“No!” He answered a bit too loudly, then took a breath. “I mean, no, I just need a minute.”

“Suit yourself.” She smiled, hoping he’d see that she wasn’t teasing him. “If it were me, I wouldn’t be able to think straight until I took matters in my own hands, if you know what I mean.”

“It’s fine, it’ll go…” He stopped mid-sentence and looked at her curiously. “What do you mean?”

“You know, tickling my fancy?” Jimmy still looked confused. “Beating around the bush? Buttering my muffin?” She grinned and waggled her eyebrows. “Rubbin’ my nubbin? Flicking the bean?” His expression made her laugh. “C’mon, masturbating, man!”

“Girls masturbate?”

“Um, yeah?” It was her turn to look confused.

“Oh.” He hesitated for a long moment. “How?”

“Jeez, man,” she hesitated. “Ask your girlfriend.”

“I, uh, don’t really have a girlfriend.”

“Fine, whatever you want to call it,” she rolled her eyes. “The girl you’re fooling around with.”

He looked awkward.

“Oh,” she realized. “Nobody? Not even at your big party?”

He shook his head.

“Not even, like, a handy in the pool?”

He cleared his throat.

“Well, shit, I’m sorry about that. But come on, didn’t they cover this kinda stuff in health class?”

“They were more focused on trying to scare us about pregnancy and diseases.”

“Right. But you’ve got the internet. You’ve never watched a girl masturbate in porn?”

“I thought all that stuff was fake.”

“You’re not wrong,” she conceded. “Well, don’t stress. You’re a good-looking guy who’s heading off to university soon. I’m sure you’ll meet a girl you like, and you can ask her stuff like this.”

“Ugh!” Jimmy groaned. “That’s exactly what I’m worried about! I’m gonna look like an idiot. I didn’t even know girls masturbated!” He turned abruptly to face her, accidentally flinging the pillow to the floor. “You gotta help me, Heather!”

“What? Help you, how?”

“Teach me about girls so I don’t humiliate myself!”

Heather blushed. Jimmy’s erection was twitching shamelessly in his shorts, but his expression was guileless and hopeful. Once again, her mind drifted easily into imagining Jimmy gasping in her cleavage as she stroked his shaft…

“I, um…” She blinked, trying to clear her mind.

“Come on, please! I really need your help. College girls aren’t gonna want to fool around with a virgin!”

“Wait, wait, wait, slow down.” She stood up and pointed at him. “I am not hooking up with you. You get that, right?”

“Yeah, that’s fine! Just show me some stuff so I don’t get laughed at.”

“Just show you some stuff.” She considered. “Like, how a girl masturbates?”

“Anything, Heather, please!”

She turned away from him. This was crazy. She should tell him to go take a cold shower. Then she could step outside and catch her breath until the embers of arousal in her core cooled down.

On the other hand… He wasn’t wrong. He’d go off to college and meet some girl who liked him, and rub her the wrong way. Literally! Plus, if she showed him a few things, it wasn’t just helping him, it was like doing a favor to all the women he hooked up with in the future. She’d be paying it forward! Hell, it was practically her duty to her fellow women to show this poor clueless boy what was what.

“Okay.” She nodded to herself and glanced at the clock. His parents wouldn’t be home for another couple hours. “Okay,” she repeated.

“What now?”

“Just, like, give me a second.”

She reached under her skirt, and shimmied her panties down. She heard Jimmy take a deep breath as she dropped them on the coffee table.

“Alright, pay attention,” she said as she turned around to face him again. “No touching.”

He nodded as she sat down, facing him.

“And you can’t tell anyone.” He nodded eagerly, but she continued. “I’m serious! You can’t go tell your dumb friends, and you definitely can’t tell my brother!”

“Of course not! I wouldn’t!”

“Okay, then.” She leaned back on the arm of the couch and spread her legs for him.

“Oh, wow,” he murmured.

“Quick anatomy lesson. These are my lips. If I spread them open like this, you can see the opening of my pussy.”

“You’re wet…”

“Yeah. You’re not the only one who got turned on by the movie. When girls get aroused, they get wet, to make it easier for a guy’s cock or a girl’s fingers to slip inside. Don’t ever try to push anything inside a girl if she’s not wet, it’ll just hurt.”

He nodded, staring intently. His cock throbbed, and he absent-mindedly rubbed it through his shorts.

“Now, this is important, look here. Up at the top, where my lips come together? They make a kind of hood to cover this—ah—this little bud here. Do you see it? That’s my clitoris. When I get very turned on, it gets a bit swollen and pokes out. It’s really sensitive. You know how it feels good to rub your cock, like you’re doing right now?”

Jimmy looked guilty and moved his hand away, but nodded.

“It’s okay, I don’t mind, but listen… A girl’s clit is not like your cock. If you try to rub her clit like you touch yourself, it’s too much. You’ll piss her off. You’ve gotta build up to that, make sure she’s ready first.”

“How do I, uh,” Jimmy licked his lips, “know if a girl’s ready?”

“Honestly, you let her tell you or show you. Girls like it when you take your time. Don’t just give her a kiss and jam your hand down her underwear. Talk to her. Ask her how she likes to be touched. Some girls like a lot of kissing. Some will want you to touch their breasts. Others don’t want that at all.”

“What, um…” His hand drifted back to his cock. “What do you like?”

“Hmmm,” she purred, idly caressing her lips. “I like sitting in a guy’s lap, and rubbing against him. Especially if I’m wearing a skirt. Fuck, I love feeling his cock grow, pressing against me. And I like it when a guy touches me like this…” She slowly teased a finger between her lips, just enough to get it wet, and traced a lazy circle around her clit.

“I thought you said,” he whispered, “not to start with the clit?”

“Yeah, but I’m already turned on. If I was sitting in your… I mean, a guy’s lap, rubbing against him, I’d be ready for a bit more direct… stimulation…” She trailed off, slowly rubbing herself as she watched him grind his palm against his erection. She wanted to see him. “Why don’t you pull that out? Show me how you touch yourself.”

“Um, yeah, okay,” he stammered. Quickly, he peeled off his shorts and boxers, then sat back down across from her, leaning on the other arm of the couch. His cock wasn’t bad to look at, she realized, as he wrapped his hand around the base and started slowly stroking the full length of it.

“Once a girl lets you know she’s ready, you can go inside,” she purred, easing her middle finger between her lips.

“How would she let me know?” His voice was husky.

“She might show you, by grabbing your hand. Especially if you’re already rubbing her, she might just push your finger inside. Or she might ask. She might say, ‘please, I need your fingers.’”

Heather shivered under his gaze. He was entranced. His eyes were locked between her legs, completely absorbed by what she was showing him. She felt almost as though he were worshipping her.

“Do you want to touch me?” She gasped, surprised by her escalation.

“Really?” His eyes met hers, equally surprised. He seemed to be checking that it wasn’t a trap.

“Yeah, really. Here, give me your hand. Start by rubbing over… Mmm, yeah, like that. Slow, gentle pressure. You can kinda let your fingers ease between my lips, but don’t go inside just yet.”

Jimmy gawked, one hand wrapped around his cock and the other caressing her lips.

“Okay, now come up a little higher… Yes, now to start, don’t rub my clit directly, try rubbing all around it—ah—like that, yeah, every movement stim—oh!—stimulates her more, and then you can start moving closer—uh—and closer, until you—ah!”

“Do you like that?” Jimmy asked, earnestly.

“Don’t ask a girl if she likes it,” Heather groaned. “That’s a turn-off. Just pay attention. Look at me—ah—right now. Listen to my breathing. See how I arch—oh!—my back when you touch me there? Feel me rolling my hips to meet your fingers?”

“Yeah,” Jimmy gasped.

“That’s how you know—oh, oh, oh!—but you also have to—ah!—know when to back off…” She gently pushed him lower, away from her tingling clit. “Now, I want your fingers. If you turn your hand like this… Yeah, you can slip your first two fingers in. Mmm. Some girls just want one finger. Some want two. Don’t do three or more unless you really know she wants it.”

“Yeah,” he breathed.

“You’ll want to move your fingers in and out… Mmm, yeah, like that. Like having sex… Don’t overdo it. Start slow, but follow her lead. Watch how she—ah—how she responds. See how her body moves with you. If you pay attention, you’ll know…”

Jimmy groaned, stroking himself faster, matching the pace his fingers were pushing into her.

“If you make a kind of come-hither motion with your fingers—ah!—like that! You’ll feel a spot—ah, ah—that’s good, that spot feels good, and if you—uh!—kinda just strum it—oh!—like a guitar. Oh, that’s good, I just need…” She reached down to rub tight circles around her clit. “Ah!—like that, yeah, you’ll… make… me… Oh! Oh! Cum! I’m cumming…”

Heather clamped her thighs shut around Jimmy’s arm, holding him in place as she clenched around his fingers. She didn’t usually cum this easily. There was something about the situation, about having Jimmy’s complete attention. Her body seemed to bloom for him, like it wanted him to see everything she had to offer.

“Holy shit,” Jimmy gasped.

“Oh fuck,” she moaned. Somewhat reluctantly, she opened her legs again, and gave him a nudge to pull out. The sensation made her shiver.

After a moment, when she could focus again, she found Jimmy staring curiously at his fingers. They were glistening wet, and a string of her cream stretched between them as he spread them open.

“Go ahead,” she smiled. “Taste it.”

Grinning, Jimmy eagerly licked his fingers clean.

“How do I taste?”

“Um… it’s like, uh… I have no idea how to describe it?”

“Ha! Yeah. It’s hard to find the right words.”

“Yeah, but, um, how…”

“How do I know what my pussy tastes like?” Heather laughed as he nodded. “Come on, be honest. Have you never tasted your own cum?”

“Um, I guess I got curious once,” he blushed. “I didn’t really like the taste.”

“There you go. Girls get curious, too.”

For a moment, neither of them spoke. The moment stretched, loaded with tension. Jimmy rested on his knees, gripping his throbbing cock, and staring at her with eyes full of lust. She gazed up at him, legs spread, pussy swollen and sensitive.

She should tell him they were done. He would respect it, she knew. No doubt, he’d go to his room and cum while thinking of her. She’d go to the bathroom to clean up, then wait for his parents to come home. And, then, to be honest, probably go home to her room and cum while thinking of him.

Or, she could let him do it here. She imagined writhing on the couch, rubbing her clit as he knelt over her, gasping and stroking his cock. His cum would arc through the air, falling on her thighs and pussy. She imagined his expression as she eagerly rubbed it into her skin, and then sucked her fingers clean.

Or she could finish what she’d started. Teaching him how to treat a woman. After all, the job wasn’t done. It’d be a bit rude to send him off without showing him how to slide his cock into her dripping wet pussy, to feel him thrust inside…

“Do you want to keep…” she started to say.

“Can we keep…” he said at the same time, and they both stopped. A crooked smile spread across his face as he realized what she was about ask.

“Oh fuck, Jimmy, come here,” she gasped, and pulled him down on top of her. He made a surprised sound that was choked off as her tongue pushed between his lips. He awkwardly wrapped his arms around her and settled his weight between her thighs. She moaned as his cock pressed against her, hard as steel against her swollen lips, eager to part around him. She squirmed, trying to position him…

Abruptly, she pulled back from the kiss, holding a hand against his shoulder.

“You. Cannot. Tell. Anyone.”

“Yeah, yeah, no problem,” he agreed.

“Okay,” she gasped. “Okay, let’s do this. If you get a girl good and excited, she’ll be eager for you. Like me right now. I want to feel you inside me so fucking hard…”

Jimmy leaned forward eagerly, but she kept holding him away just a bit.

“If she’s as wet as me, you can just… put yourself against her opening… like this… and then—oh!—Fuck, Jimmy, I was gonna tell you when, but you’re already inside!”

He groaned, staring into her eyes, and shifted as if to start fucking her.

“No! No, wait, just—oh—just wait a minute. Give me a minute to adjust. I—ah—love the feeling when a guy first enters me, let me savor it. Oh my god, I can feel you throbbing inside me…”

Slowly, she rolled her hips, encouraging him to start moving with her.

“Yeah, like that, start slow. Oh, fuck. Don’t just start railing a girl, you—ah!—gotta build up to that, even when she’s as turned on as me. Oh god-damn, yeah, yeah, move with me, I—mmm…”

She pulled him back into a kiss, moaning into his mouth as he followed her lead and started thrusting into her. Quickly, she escalated the pace. Every thrust, every time he bottomed out, she saw a flare of color out of the corner of her eyes.

He broke the kiss, and buried his face in her shoulder, fucking her harder and faster. She wrapped her legs around him, and held on as he moved with increasing urgency.

She wanted to tell him more. To get on top and ride him. She wanted him to get behind her. She wanted to show him when to pull her hair. When to push his thumb into her ass. She wanted him to cum.

She wanted him to cum!

“Jimmy!” She gasped into his ear. “Are you—ah!—close?”

“Yeah,” he groaned. “Can I?”

“Yes! Oh, yes! I want you to—ah!—Cum in me!”

He moaned and went rigid on top of her. She gasped at the feeling of his cock twitching, and the spreading warmth inside. After a long moment, he relaxed, and she ran her fingers through his hair, breathing softly in his ear.

“Fucking hell, Jimmy,” she sighed. “I think you’re gonna do alright with the ladies.”

He tried to give her a kiss as he climbed off her, but she squeaked, shoving a hand between her legs as his cum leaked out. He handed her a tissue box, and she wiped up as he watched, fascinated. Mercifully, it had only dripped on the inside of her skirt, not the couch. That would have been hard to explain to his parents.

Jimmy pulled on his shorts and followed her into the kitchen. She poured them each a glass of water. When she passed his over, his eyes sparkled with a mixture of gratitude and awe.

“Well,” she laughed, “don’t you look like the cat who caught the canary?”

“Kinda feels that way.” He grinned, and took a sip of water. “You know, I was just thinking. Like, you’re home for a few weeks, right?”

“That’s true.”

“And I don’t leave for a few weeks.”

“Go on,” she smiled, knowing where he was going with this.

“So, maybe you could show me some more stuff.”

“Don’t get cocky, kid,” she laughed. “Girls like a bit of confidence, but too much can be off-putting.”

“Is that a no?”

“I mean,” She bit her lip. “I suppose there’s a bit more I could teach you…”