A Friend with Many Benefits

Jess could hear her heart pounding as she shut the door to her apartment. Her palms sweating profusely, she locked the door behind her.

Fuck, fuck, fuck, fuck, fuck, fuck, fuckkkkkk I can't believe this is happening.

Jake was waiting for her downstairs in the lobby. Sitting on one of the benches, he tapped his foot anxiously as he scrolled through his phone. He wasn't paying attention to any of the pictures popping up on his Instagram feed. He thought about their history, and all the times something almost happened but she changed her mind last minute.

Not this time, apparently.

He wondered what was different this time.

Jess stepped out of the elevator into the lobby, spotting Jake at the other end of the room. He looked up from his phone upon hearing her footsteps and stood up. Adjusting his sweatshirt, he smiled at her nervously.

"Hey," she smiled demurely.

"Hi."

They embraced in an awkward hug. They hadn't been in the same room since high school.

"How are you?" she asked, trying to fill the silence.

"Good, yeah," he replied, combing his hair out of his face with his fingers. Jess took a small inhale.

Shit, he's got nice hair. And nice hands.

His solid six-foot-one frame was neither lean nor muscular, but he nonetheless hid it underneath the baggy sweats he wore every day. His dark, wavy hair was arguably his best feature, but often kept it hidden under the hood of his sweatshirt. His large, powerful hands were a focal point too. He had a boyish, sheepish quality that was sometimes awkward but undeniably charming.

"Come on, I'll show you up," Jess turned towards the elevator.

Jake eyed her frame as she walked in front of him.

Damn.

His eyes immediately drifted to her skinny jeans, hugging her shapely, long legs. Her hips swayed back and forth as she walked, and she brushed back the long dark hair that fell in her face. Jake and his friends would often talk about how fuckable she was back then, he just never expected anything to happen. Until now.

"Your building is really nice," he said once they were in the elevator. Her hair smelled intoxicatingly sweet of shampoo when she moved her head.

"Thanks!" she smiled. "It's more expensive than my old place, but I think it's worth it."

"Yeah", he nodded. The elevator dinged and opened onto the 7th floor.

"How's school going and everything?" she asked, thinking that awkward small talk was preferred to quiet.

"It's fine," Jake sighed. "Still learning the city. If I'm not in class I'm smoking weed with my cat."

She giggled. "I thought they had catnip for that".

He laughed, relieved the joke broke a bit of the tension.

"You always were a funny one," he smirked back at her.

They reached a door labeled number forty-two.

"This is me," she said, inserting her key into the lock and opening it.

"Can I get you a drink or anything? I have beers in the fridge."

"Um, yeah sure". Jake looked around the small apartment. The walls were that same off-white every apartment in the city was painted. There were scuffs in the paint by the door, but the rest of the walls were covered with charcoal sketches of nude women.

"Do you make these?" he asked while she was rummaging through the fridge.

"Yeah," she laughed nervously, handing him a can. He walked past her to a drawing hung up on the wall behind her, clearly the outline of a woman's buttocks.

"This you?" he raised his eyebrows sheepishly.

Jess shuffled her feet.

"Uh yeah," she laughed. "I draw myself sometimes when I'm feeling insecure."

Jake looked up at the drawing again before looking back at her.

"Well, I gotta say you got nothing to be insecure about," he said, taking a swig of his beer. He hung out with the football players and often adopted their fuckboy swagger.

Jess smiled and looked down at her toes.

"Thank you, I appreciate it."

Jess wasn't really sure why she called him after all those years. Maybe it was loneliness, or maybe it was something more. She always found him attractive, but high school can be cruel about people's love lives. She couldn't be seen going out with a younger guy, let alone a guy like Jake. But still, something always intrigued her about him. She occasionally thought about what it would be like if she submitted to his innocent flirtatious advances.

She shook the thought out of her mind, taking a big sip of her beer. Gathering all the feminine allure she could muster, she moved closer to him.

"I'm really glad you came over tonight," she purred.

Jake raised his eyebrows, smiling.

So, she wasn't kidding on the phone.

"You caught me on a good night," he shrugged, feigning nonchalance. "I didn't have other plans."

She rolled her eyes, taking another drink. Yeah, right.

Jake laughed to himself and took a swig.

"You think you're so funny", she trolled sarcastically.

Jake flashed another sheepish smile, pouring another sip of beer into his open mouth.

"Yeah, I do."

Jess inched closer to him still. She purposefully left the lights dim when she left to grab Jake from the lobby.

Jake put down his beer on the table next to him, leaning back against the wall. From the front, Jess was even sexier. He loved the way her gray-blue eyes looked up at him, and how adorable she looked when she laughed. His eyes traced down her next to her ample chest, the buttons on her white blouse straining to remain closed.

I can't wait to rip that apart that later. The alcohol clearly was already affecting his thoughts.

Jess watched as Jake practically undressed her with his eyes. I knew he still wanted me.

She took another step closer to him. Her heart was beating even faster now.

"Somebody's a little full of himself," she prodded. Jess prided herself on her flirtatious quick wit.

Somebody's about to be full of me. Jake joked to himself.

"What can I say, I'm a pretty cool guy." The scent of her hair grew stronger as she moved closer to him.

"What are we to do about that arrogant attitude?" Jess cheekily crossed her arms. "I think I might need to put you in your place."

Jess took another step closer, putting their bodies mere inches from each other.

"Why don't you try and tame me?" Jake chuckled.

That's enough of that.

Jess uncrossed her arms and grabbed Jake's hoodie strings. Pulling him closer to her, she kissed him.

Whoa.

5 years of sexual tension exploded in a matter of seconds.

We should've done this ages ago.

Jake felt his stomach flutter as she pressed her velvety soft lips to his. He took his hands out of his sweatshirt pocket and grabbed her waist, pulling her closer to him.

Jesus, those hands.

Jess felt a throbbing as he touched her for the first time. She moved her hands from his chest up to his neck, running her fingers through the hair at the back of his head. Jake shuddered at her touch, feeling the goosebumps prick up all over his body.

Jess moved her hands from his hair down around his ear, tracing her fingers along his jawline and then his neck. She could smell the musky scent of his cologne or deodorant. She didn't care what the hell it was. It smelled so fucking sexy.

They kissed for what felt like an eternity. Jess was growing impatient. She needed him. Now.

She moved her hands from around his neck and grabbed his wrists, sliding his hands down from her waist to her ass.

Oh shit. She wants me.

Jake broke away from kissing her, surprised.

"Is that okay?" Jess looked concerned.

Jake simply looked her up and down again. Then, sliding one hand to the small of her back, he cupped her buttocks with the other, squeezing hard.

Jess giggled as she went in to kiss him again. Jake pulled her in so close that every part of them touched. She felt one part of him growing hard.

Perfect.

Jake, sensing she could feel him, pressed into her. He only hoped he would last long enough.

Jess moved her hands down to his hips. Sliding her hands under his sweatshirt, she grabbed his hipbones.

Fuck.

Jake squeaked out a moan. He broke their kiss, instead moving his lips down her jawline, under her ear, and down her neck. Jess couldn't help but breathe heavier. Neck kisses were her weakness. She felt her knees buckle slightly as he brushed his lips over the tender flesh of her neck.

"You like this, don't you?" Jake whispered into her ear, smiling. Jess could only muster a breathless nod.

Jake grabbed her ass harder, moving his hands further and further underneath her. Jess felt his touch mere inches from where she really wanted it. She was done for.

She pushed him off of her and shoved him into the wall behind them. Sliding her hands under his sweatshirt once more, she grabbed the hem of his shirt and helped him pull both layers off. He threw both on the floor beside him.

She drank him in, feeling the heat radiating off his bare skin. His collarbones were sharp and defined, splayed across his broad, solid shoulders. Although his muscles weren't as large as when he played football in high school, he was still as strong.

"Your turn," he smiled down at her, eyeing the buttons on her shirt. Slowly, deliberately, he unbuttoned each button one by one, starting with the one at the center of her sternum, revealing her white satin bra. She stared into his wide, brown eyes as he stared at her body. Sensing her discomfort with being so exposed, he eased the sleeves of the shirt off her shoulders and pulled her into him.

"You're so gorgeous," he whispered.

She wrapped her arms around his neck once more, feeling the warmth of his skin press against hers. The sensation was intoxicating.

"So are you," she whispered back, gazing up at him.

She ran her fingers down the length of his torso, grazing lightly over his nipples. She stopped at the waistband of his sweatpants. The elastic of his American Eagle underwear peaked out the top of his sweatpants.

So sexy.

Slowly, she slipped her finger underneath the elastic and ran her fingertip across his stomach. She felt Jake's breathing quicken as she touched him, smiling to herself about being such a tease.

Jake smiled, breathlessly. He had no idea he could want a girl so bad. Gently, he used his hand to guide her chin up to face him and went in for another kiss. At first, their lips barely touched, but it felt like electricity. Gradually, he kissed her faster, and harder. Jess moved her hand behind his head, pushing his head into hers. She parted her lips slightly, and he took it as a sign to slip his tongue inside, running it over the back of her bottom teeth. Pulling away, he took her bottom lip in his mouth, sucking it gently. Jess smiled through the kiss. She cheekily bit his bottom lip, letting her teeth graze over it as she pulled away.

God damn.

Jake was hard. So hard. He ached to be inside her, but experience told him he needed to wait. It would be so worth it.

Jess felt a tinge of pride feeling how hard she was making her old friend. Feeling especially cheeky, she ran a hand down his torso once more, moving past his waistband to his lap, cupping him in her hand. Jake inhaled sharply as she ran her fingers over his bulge.

Fuck, I can't take much more of this.

Thinking fast, Jake wrapped his arms around her waist and picked her off the ground. Jess wrapped her legs around him as he went in for another kiss.

No guy has ever done this before!

Still kissing her, Jake carried her over to the corner of the studio where her bed was, throwing her down onto the sheets. Giggling uncontrollably, Jess watched as Jake kicked off his shoes and climbed on top of her. The sight of him above her made her stop laughing instantly.

Holy shit.

For a tall girl, she had never felt so small. Jake grabbed each of her ankles and spread her legs, wedging himself in between them. He hovered above her, supporting himself on his strong arms. He loved the way she looked up at him so demurely.

Jess wrapped her legs around his waist once more as he lowered himself onto her. She loved the way his weight blanketed her so comfortably, but couldn't help but moan as he buried his face in her neck. Slowly, he started planting his kisses lower and lower, moving from her neck, over her collarbones, down her sternum, to the middle of her bra. He slowly shifted to one side, using his free hand to gently cup her breast. He could feel her nipple get hard instantly. Meeting her gaze with his, he slowly pulled down the cup of her bra to reveal her very erect pink nipple. Smiling, he kissed it softly, then took the whole thing in his mouth.

Oh, god.

Jess's eyes rolled back in pleasure as Jake continued to suck on her breast. She could already feel her wetness pooling in her underwear. She arched her back and reached around to unhook her bra. Realizing what she was doing, Jake sat up and helped her unclasp the hooks and slide the straps off her shoulders. Immediately, her supple tits bounced out of the cups.

Am I dreaming?

Leaning back down, he cupped both breasts in his hands, running his fingertips over her nipples.

"You're so much hotter than I could've ever imagined," he smiled quietly.

Jess giggled, pulling his head back up for a kiss. Jake wrapped his hands around her shoulders, slowly beginning to rock himself against her. Jess inhaled, loving the way his bulge felt pressing against her throbbing mound. Jake smiled to himself, already feeling the pulse of her second heartbeat.

Jake rocked into her a second time, and Jess couldn't help but let out a soft moan.

Fuck, this feels good.

Jake nibbled on her earlobe. "You really want me, don't you?"

"Yes, please," Jess whispered, breathlessly.

"How do you want me?"

Jess gazed up at him with the eyes of a vixen.

"I want to be on top of you," she purred. "Riding you. And I want you grabbing me all over and telling me how good it feels while I'm doing it."

Jake raised his eyebrows in surprise. He'd never had a girl be so direct with him before. Of course, he was happy to oblige.

"Ok," Jake smirked. "But only if I can taste you first."

Jess's eyes went wide as she smiled. Jake was already buttoning her jeans, pulling them down with her underwear to reveal her perfectly trimmed cunt. He was already intoxicated by the smell of her sex as he adjusted himself to meet it. Her thighs were so soft and supple on his cheeks, and he grabbed them firmly with both hands, moving her legs on top of his shoulders. He grabbed her ass from underneath her and pulled her towards him.

Just touch me already.

Jess's clit had been throbbing for what felt like hours. When his tongue finally touched her mound, it felt like a shot of ecstasy. She moaned, loudly.

Smiling, Jake got to work, licking her clit up and down. He loved the sweet, tangy taste of her.

"You're so wet for me," said Jake coming up for air. "Good girl."

Jess let out a noise somewhere between a yelp and a squeal. She'd always had a bit of a praise kink. Laughing, Jake continued to tease her with his finger.

"You like when I call you a good girl don't you?"

Jess nodded, biting her lip.

"Use your words."

"Yes, sir," Jess smiled cheekily.

"That's more like it."

Jake slide his thumb from the top of her mound, over her clit, and towards the source of her wetness. He circled his thumb around her opening, looking back up at her. Her eyes met his, and with a simple nod, he entered her for the first time with his fingers.

Her cunt ached for him. She moaned again as he inserted his thumb further inside her.

God this feels so good.

She couldn't wait any longer.

"I need you. Now," she urged.

Smiling, Jake sat back onto his knees as Jess sat up and climbed on top of him. Straddling his hips, she knew she was staining his sweatpants with her wetness. She didn't care in the slightest.

Just like he did to her, she lowered herself down by the arms, burying her face in his neck. She loved the way she could hear him breathing in her ear. She started kissing his skin softly, planting her kisses further up, and placed a few nibbles on his earlobe. Then, she slowly moved south, grazing her lips over his collarbone, his chest, his ribcage, his stomach, and finally the trail of hair that lead from his navel to the waistband of his sweatpants. She felt him twitch underneath her and loved the power she had on top.

Tracing her finger once more under his waistband, she looked back up at him. He had one arm bent behind his head, eyes closed, in apparent agony.

Just how I like them.

She used both hands to pull down his pants, revealing his rock-hard member. She gazed at it longingly. Perfectly pink, she took it in her hand, encircling his shaft with her forefinger and thumb. Her fingertips just touched as they encircled it. She gently stroked the length of his six-inch shaft.

It's perfect.

Jake was breathing even heavier. Her fingers felt like heaven on his engorged cock.

"Oh fuckk," he moaned.

Smiling, Jess moved her hair to the side with one hand and took him in her mouth. She loved the way he filled her, running her tongue over the spongey flesh. She flicked her tongue back and forth over the tip of his beautiful shaft before stroking him some more.

Finally, she couldn't take it anymore.

She tossed her hair back over her shoulder and straddled him again. She took him in her hand and used him to spread her wetness all over herself, taking special care to rub the tip of his shaft on her throbbing clitoris. Then, slowly, she guided him inside her.

"Wait," he interjected. "Shouldn't we use a condom?"

Jess hesitated. She wanted him. Now.

"It's okay, I'm on the pill," she lied. She figured $40 worth of plan B tomorrow was worth this moment of ecstasy.

He nodded, grabbing her hips as she lowered herself onto him.

God almighty.

He felt like heaven inside her. She loved the way he filled her perfectly, and Jake could barely contain his pleasure. They both moaned loudly.

"God, you feel so good," Jake mouthed breathlessly.

Jess threw her head back as she began to bounce up and down on him. She knew she wasn't fit enough to keep this up, but god did it feel good. Fully lowered onto him, she began to rock her hips back and forth, feeling her clit rub on his pubic bone.

"Ohh myy goddd!" her voice vibrated as she bounced up and down.

Jake couldn't believe his luck. He watched as her perfect breasts bounced up and down as she rode him. It was a wonderful sight. He took one hand off her hips and tried rubbing her clit when all of a sudden Jess stopped.

"I want you fucking me now," she lied, simply out of breath.

Jake smiled. She swung her leg off of him and laid on her back and he climbed on top of her.

"I'll only fuck you if you'll be a good girl for me," Jake smirked.

Jess looked back at him with her fuck-me-eyes.

"Yes, sir."

"Good girl."

Jake inserted himself with one firm thrust.

Jess gasped. She wrapped her legs tightly around him as he began to rock in and out of her.

God, he's so much deeper now.

"You're so- deep- inside me," Jess moaned as he fucked her.

"You can take it," he encouraged her. "Be a good girl for me and take all of it."

He pressed himself tightly against her as she wrapped her arms around his shoulders.

Jake hadn't felt more pleasure in his life as he thrust in and out of her. He lowered himself completely onto her and buried his face in her neck. He read somewhere girls liked when you moaned in their ears as you fucked them. He certainly had a hard time being quiet.

"Jake," Jess gasped suddenly. 'Oh my god, I'm gonna cum!"

The feeling in her cunt was building exponentially with each thrust of his hips.