Her Best Friend's Brother Ch. 01

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Sex by the pool.
2.8k words
4.5
2.04M
87

Part 1 of the 4 part series

Updated 10/30/2022
Created 12/03/2010
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Allison needed to talk to Carrie, desperately. If ever there was a time for her best friend to lend a shoulder to cry on, it was now. She rang the doorbell to Carrie's house and bit her lip to keep the tears from spilling over. She wanted to be in the sanctuary of her friend's room before she let her emotions go.

Carrie's brother, Jesse, opened the door.

"Is Carrie here?" Allison asked in a shaky voice.

"Nope, she went out of town with mom and dad for the weekend—to see some musical."

Crap. She'd forgotten about that.

Jesse looked her up and down.

She knew she looked like a mess. She felt like a mess. She'd walked over a mile to get here, and it was all for nothing. She could feel the sweat rolling down her back. She'd probably soaked through her thin tank top.

"You want to come in anyway?" Jesse stepped back so she could come inside. The air conditioning wafting out the door felt like heaven.

"Yeah, if you don't mind." She walked into the foyer and stood awkwardly in front of him. She didn't know him well, had only met him a few times. She and Carrie graduated high school two weeks ago, but Jesse was three years older than Carrie. He'd already been away at college when Allison had moved here.

"Are you okay?" he asked.

She nodded. "I'm fine. I just... I had some personal stuff happen today and I was hoping to talk to Carrie about it." She pulled her damp tank top away from her skin and studied Carrie's brother.

His green gaze was focused on her breasts. She glanced down. Her nipples had hardened in the cold air and they thrust out in sharp peaks through her bra and tank top. She resisted the urge to fold her arms over her chest.

Her boyfriend of two years, Rodney, had broken up with her this morning. That was why she needed Carrie. Rodney had told her that they weren't compatible. Compatibility had never been a problem until she'd finally relented to let Rodney have sex with her on graduation night. Then all of a sudden, they weren't compatible. All of a sudden, he didn't think she was attractive enough, he didn't think they had enough sexual chemistry for a long term relationship.

"Do you think I'm attractive?" Allison asked.

Jesse's eyes widened and his gaze was suddenly on her face. "Uh, well, yeah..." He sounded leery, like he thought she was setting a trap for him.

She found him attractive. He was only wearing a pair of green swim trunks. He was wiry, muscled, with defined abs and biceps. His right bicep was circled with a loopy tribal tattoo. Sexy.

She smiled. "I'm not trying to put you on the spot. It's just that I just went though a breakup and I'm feeling a little insecure all of a sudden. That's what I wanted to talk to your sister about."

He nodded and smiled back. Straight white teeth, a square jaw, beard stubble. He must not have shaved this morning. "So you needed Carrie to tell you you're attractive?" His tone was teasing.

Her cheeks heated and she rolled her eyes. "I just needed her to give me the speech. You know, the 'Rodney's a jerk, there are other fish in the sea, you're beautiful and will find someone else way better' speech."

"Ahhh... Well, I don't have a prepared speech. And I don't know Rodney. But if he told you you weren't beautiful, then he's a liar and a jerk."

Her heart melted a little and she looked at him through lowered lashes. "You don't have to go overboard." She pressed a hand to her dark, sweat-dampened hair. It was pulled into a sloppy ponytail. "I'm not exactly looking my best today."

"You look cute." He reached out and tucked a stray strand of hair behind her ear.

Hot and cold clashed in her body and goose bumps spread down the side of her neck, down her arms.

"I was about to jump in the pool out back when you rang the bell. Want to join me? You can tell me all the reasons why Rodney's an ass."

She laughed. "That would probably make me feel better. I don't have a suit though."

"Carrie washed one of her suits last night and left it hanging in the laundry room. You can wear that."

Allison and Carrie had never been able to share clothes. Carrie was tall and willowy, with subtle curves and small breasts. Allison was four inches shorter with an hourglass figure—plump hips and heavy breasts. "I wouldn't fit in one of Carrie's suits."

"It's a two piece and it's stretchy. Try it and see."

She wouldn't be able to get in it. She would look fat, feel fat. Her self esteem couldn't take another blow today.

Jesse was already walking towards the back of the house, so she followed him. But she was frantically trying to think of an excuse so she could leave.

He opened the door to the laundry room, then tossed her a skimpy blue bikini. It was the string kind that tied in the back and behind her neck. The bottom piece tied on each hip.

"Will it work?" he asked.

"Maybe," she said hesitantly. She stepped into the laundry room and closed the door behind her. She shucked her clothes and tied the bikini bottom on. It was skimpy, but it covered what had to be covered. The top was another matter. Her breasts were much too big for the tiny blue triangles.

"Hey," Jesse called through the door. "If the suit doesn't work, you could just swim in your underwear."

She could. Her bra covered way more than Carrie's top did. It was multicolored and had a little blue in it, so it sort of matched. She put it back on and stepped out.

His gaze slid over her, lingering on her breasts, her waist, her hips. He seemed to like what he saw, and that made her feel bold.

She grabbed his hand and stepped close to him, the side of her breast grazing his arm. "Let's go swim."

He led her through the patio doors and to the in ground pool. He jumped in, but she walked around to the stairs, letting her hips swing a little more than normal. She locked her gaze on him and slid into the water slowly.

With a few smooth strokes he was by her side. He reached out and pulled her ponytail loose. She splashed him, and they played and flirted for a while. Finally, he pulled her close—her back to his front. They were deep enough that with their feet touching the bottom, the water came to just below her shoulders and to his chest. His hands were at her waist, his fingers lightly rubbing her soft belly.

"Did Rodney tell you you weren't attractive?" he asked.

"Sort of. He said we weren't sexually compatible." Part of her couldn't believe she'd just said that out loud.

"Did you have sex with him?" His fingers were tracing the top edge of the front of her bikini bottom and she was finding it hard to breathe.

"A few times... Three times."

"Was he your first?"

"Yes."

His lips were centimeters from her ear. She could feel his breath on her skin. And his hands... His hands had moved to her bottom. He was cupping her ass.

"Did he make it good for you?"

She bit her lip. She didn't know how to answer that. She and Rodney had been fooling around for over a year, heavy petting, fingering, eventually oral sex. But she'd never agreed to let him push inside her until graduation night. And it had been...awkward. Uncomfortable even. He had shoved himself inside, thrust a few times—bouncing her hard, grunted, and collapsed on top of her. He'd told her the next time would be better, but it wasn't. And neither was the time after that.

"Did he make you come, Allison?" His tongue traced the shell of her ear and she whimpered.

"Sometimes," she whispered. But never when they'd actually had sex. Only ever with his hand, and most of the time he'd complained that she took too long. She hadn't known what to do about that, so sometimes she'd faked it and told him she'd come when she hadn't because she hadn't wanted him to get frustrated with her.

"He should've made you come every time. At least once."

Jesse sucked the bottom of her earlobe into his mouth and lightly raked it with his teeth. His stubble lightly scratched the sensitive skin on her neck. She leaned against him, wanting more.

He kissed her jawline, inching closer to her mouth and she turned to face him, touching her lips to his. The kiss deepened instantly. She opened her mouth for his tongue. A hot, heavy ache settled low in her belly and she pressed her hands against his chest, tracing the lines of his muscles with her fingertips while their tongues tangled.

She felt a flutter at her right hip, felt his hand graze her left thigh. Then her blue bikini bottom floated to the surface of the water. She broke the kiss and pulled back, unable to take her eyes off the bobbing scrap of bright blue material.

Jesse kissed the side of her neck, his lips sliding from just below her ear to the curve of her shoulder. She didn't move away. She didn't think she wanted to, but she wondered if she should. His hands slid up her belly and his fingers traced the underwires of her bra, grazed the undersides of her breasts.

"Jesse," she said. "My... uh..." She gestured to the bikini bottom that had drifted out of reach.

"Have you ever swum naked?" He licked the side of her neck.

"No."

His hands slid to her back and unhooked her bra. The cups floated up, but the straps stayed on her arms. His hands cupped her breasts and he lightly pinched her nipples between his thumbs and forefingers. She groaned and moved her arms, letting the bra float away.

"You have now," he said in her ear.

"Does this count as swimming?" She asked, breathless, as he pulled on her nipples and kneaded her breasts.

"This is better than swimming." He kissed her again, slow and deep. His hands slid over her wet skin, from her breasts to her hips to her ass and back up again. She threaded her fingers in his hair and held him close even after he broke the kiss. They were both breathing hard.

He squeezed her breasts again. "So soft and curvy," he murmured. "Float for me."

"What?"

"Lay back and float. I want to look at you." He didn't give her time to think about it. He just swept her up in his arms and let her go.

Droplets of water rolled down her breasts. She thrust her toes above the surface and stretched out her arms. She'd never been naked outside—at least not since she was a baby when her mother had let her run around the yard in a diaper. She'd never let Rodney, or any other boy, look at her body in the sunlight. But she was letting Jesse. He didn't make her feel self-conscious. He made her feel... sexy.

She floated in front of him for a few minutes while he dribbled water over her breasts. Her nipples tightened even more with each cold drop.

"Stay where you are," he said and swam for the edge of the pool.

"Where are you going?"

He didn't answer, but in a minute he was back with an inflated floating pool chair.

She stood up in the pool and reached for him.

"Get on this," he said.

Instead she wrapped her hand around his erection through his swim trunks. "You should be naked too."

He lifted her onto the chair, then yanked his shorts down and tossed them away. He grabbed her ankles and pulled her over so she floated between him and the edge of the pool. His hands slid from her feet to her knees, which he pushed apart as he sank down in the water. Then he kissed her, just above the knee.

He looked up at her, his face so close to her naked crotch that she could feel his breath. She swallowed hard as she watched him run his tongue up the inside of her thigh.

"Are you wet?" he asked.

"We're in a pool."

He smiled at her and pressed a finger into her slit. "That's not pool water."

She moaned, loud and long, as he dipped his fingers into her juices and spread them over her clit.

He teased her, easing first one, then two fingers inside. She gasped and tensed as he cupped his hand, putting pressure on her clit with the base of his palm while his fingers rubbed inside.

"Don't stop," she moaned.

He eased his fingers out.

"No, no, please. Oh, god, don't stop."

He thrust them back in and she squealed. She squirmed on the slippery floating chair and threw her arms out to her sides and behind her to grip the edge of the pool with her hands. It felt so good, her head was spinning. Rodney had never finger fucked her like this. She couldn't stop begging. Each time he pulled out of her she gasped, "Please, don't stop."

He plunged in hard, rubbing circles on her clit and she opened her mouth in a silent scream as wave after hot, delicious wave of ecstasy rolled through her. She went limp on the chair, her hands floating in the water, her breasts heaving with each deep breath she took.

She finally raised her head and looked at Jesse who stood between her legs in front of the chair. His cheeks were flushed and he was breathing hard.

"I want to fuck you," he said, his voice strained.

"I want you to."

He pulled her off the chair and she gasped as the cold water hit her body. He pulled her through the water to the stairs and they climbed out.

"Meet me by the lounge chairs," he said, gesturing to the group of padded reclining pool chairs that sat in the shade of the pool house. Then he disappeared into the house.

He was back in less than a minute with a condom in his hand. He lay down on the chair and covered himself. Then he reached out to her. "Straddle me."

She stepped over him, but hesitated, unsure what to do.

He put his hands on her hips and guided her down. "Hold on to me and take me inside you," he instructed.

She wrapped her fingers around his shaft and he sucked in a breath. Holding the base of his penis, she rubbed herself with him, letting her juices coat his tip. He made a strangled sound and she smiled.

"This feels good," she breathed. "You're so hard and hot."

He thrust his hips forward, nudging her and she moaned when he grazed her clit. He reached up and grabbed her breasts, squeezing her nipples and tugging her down towards him. "Take me inside you," he growled before latching onto a nipple and sucking hard.

She shifted her hips and sank down on him. She threw her head back and cried out at the full feeling. He stretched her, but she liked the sensation.

His hands locked on her hips and guided her movements, up and down, gradually faster. She was sitting upright now, riding him hard, and her breasts bounced with every movement. His hands urged her to go faster, harder, and his hips thrust to match her rhythm. She watched Jesse's face. His brow was furrowed and his jaw was clenched. He stared at her breasts and his eyes looked glazed.

This didn't feel like the sex she'd had with Rodney. The sensations ripping through her body made her feel high, and she couldn't stop the grunts and pants exploding from her throat. She thought she felt another orgasm building and she closed her eyes to concentrate on the feeling.

Jesse slid one hand over her belly and his thumb burrowed down until he found her clit, hard, swollen and throbbing. One touch was all it took to send her over. She screamed and clenched her inner muscles hard around his shaft.

He came too, thrusting and shuddering beneath her.

She curled up on top of him, still holding him inside her. He wrapped his arms around her and pressed a kiss to the top of her head. They stayed like that for a long time, until he finally led her into the house where she called her parents and told them she'd decided to spend the weekend at Carrie's. She didn't have any clothes, but Jesse assured her she wouldn't need them.

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12 Comments
AnonymousAnonymousover 8 years ago
To the first anonymous comment

The story said she didn't know him well, she had only met him a few times. So she didn't just meet him

dirtylittlewhore7213dirtylittlewhore7213over 8 years ago
AWESOME!!!

Totally loved it!!!!

AnonymousAnonymousover 8 years ago

No build up, she's fucking him when she's just met him?

AnonymousAnonymousabout 9 years ago

I liked this story but they jumped in to sex to fast, there was no build up. But other than that it was good.

youngblood019youngblood019almost 13 years ago
wow

it's excellent! a true teenage dream:)

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