Family Trip 01: Brother and Sister

This is a story I wrote a long time ago and had saved on an old laptop. Rereading it I decided to break what I had written into several parts, so each short installment could focus on just one or two similar sex acts at a time.

This installment is about a bisexual woman who has never been with a man, and her virgin brother on the way to a wedding. All their play in this first part is exploratory, with a focus on fingering and handjobs.

If you're looking for something a bit kinkier please check out my story list for offerings much more exotic than this!

As with everything I write, this story takes place in a happy alternate universe where STD's and birth control are not a concern.

IsabellaEmily

~~

"You don't need two fucking pillows," said Dori. "You're not even using the second one."

"I always sleep with two pillows," said Harry.

"So do I," Dori told him. "I'm used to a body pillow, and I tossed and turned all night last night without it. You're not going to hog the third pillow again tonight."

Dori and her brother Harry were sharing a bed for the second night in a row. After nine hours in the car enroute to a cousin's wedding the day before they'd checked into a motel, opting to share a room in order to save money.

After another nine hours in the car they realized they were going to have to share a room at their grandmother's house for the entire weekend.

They'd counted on having the two upstairs rooms to themselves while their grandmother slept on the first floor, but at the last minute their elderly great aunt had gotten the second upstairs room, and they'd ended up sharing a full-sized bed.

"It's just one night," said Harry. "Live without it."

"Last night was one night," Dori said, reaching under the sheet and pulling the third pillow away from him with a grin. "Tonight, will not be the second night. We'll find a dollar store and buy more pillows tomorrow if you need one so bad."

Harry wanted to argue with her but decided that pressing the issue wasn't worth being asked to explain why he wanted the pillow as a barrier between the two of them.

The truth was he was afraid he'd wake up with a boner and without the pillow to hide it she'd see it. Or even worse she'd feel it. He'd woke up with her leg pressed against him last night, and if she hadn't been asleep, she'd have felt his hard-on pressing against her thigh.

And without the privacy of his own room to jerk off before going to sleep he was almost guaranteed to wake up rock hard.

He rolled onto his side facing the window, hoping that he'd either wake up before Dori or be facing away from her when his morning wood arrived.

"I take it you've given in?" Dori asked with a giggle.

"Yeah," sighed Harry. "Keep the damn pillow. This is already uncomfortable. No point trying to make it anything else."

"Uncomfortable?" asked Dori sarcastically. "What could be uncomfortable about a twenty-three-year-old woman sharing a bed with her little brother?"

"Nothing," laughed Harry. "Except the brother is nineteen and not used to sleeping with his own lesbian sister."

"Be glad that Debbie couldn't make it," said Dori. "She'd be in the bed with me, and you'd be stretched out on the floor listening to her make me moan."

"Bullshit," he grinned. "If I had to listen to you two fool around, I'd get the bed."

She stuck her tongue out at him and reached for the light on the nightstand, and as the room plunged into darkness the image of her sticking her tongue out gave way to a mental image of her using that tongue to lick her girlfriend.

Harry quickly pushed the mental picture aside. He'd been attracted to Debbie since the first time Dori brought her home from college, and he'd often resisted fantasizing about her because he was afraid he'd have a hard time separating sexual thoughts about her from sexual thoughts about his own sister.

The light snapped off and Harry felt Dori moving around as she settled in next to him.

"So, are you used to sleeping with anyone?" asked Dori softly.

"Are you asking about my sex life?" asked Harry slowly.

"We don't have to discuss it," said Dori. "But since I woke up last night with your sex life pressing against my thigh, I figured I was entitled to ask where all it's been."

"Geezus I'm sorry," said Harry, feeling himself blush in the dark room.

"It happens," said Dori with a laugh. "It's not like you can control it. It wasn't the weirdest thing I've woken up to. Don't worry about it."

Harry stared into the darkness, now even more anxious about what would happen in the small bed during the night. The last thing he needed was his sister teasing him in front of others about his hard-on.

"Hey," whispered Dori as if she could read his mind. "I'm just teasing you. It really does happen to all guys in their sleep. It's nothing to be freaked out over."

"I guess," Harry answered. "But my sister rubbing herself against me in the night isn't exactly the wedding hook up story I was hoping for."

"I don't think Aunt Gertrude is a blood relative," Dori said softly. "If you want to sneak down the hall and try for an experienced woman."

"In the first place that's disgusting," said Harry, rolling onto his back. "And in the second place, no matter how old she is, she isn't more experienced than the slut that's already in this bed with me."

"That's probably true," conceded Dori. "But wouldn't it be cool to fuck someone who was alive when sex was invented? Imagine the shit she knows."

They both laughed, and Dori turned and hit the screen of her phone on the nightstand. It started to quietly play some soft music.

"I won't leave it on long," she said with a yawn. "It just helps me fall asleep."

"It doesn't bother me," whispered Harry, wondering how many more hours it would be until he could jerk off.

~

He woke up, unsure how long he'd been asleep but sensing that it hadn't been very long. He was still on his back, and his sister's music was still playing softly. He closed his eyes and wondered what had made him wake up. He listened for Dori's gentle breathing, and assured himself that she was asleep next to him.

He wondered for the tenth time if there'd be any cute women at the wedding that he wasn't related to. Not that he could bring one back to his grandmother's house, into a bed he was sharing with his sister.

But if he met a cute bridesmaid with her own hotel room who was interested in a virginal college freshman he certainly wouldn't complain if she was willing to fuck. Or even just to fool around and exchange oral pleasure. Hell, he'd never even had a handjob, so he'd settle for that and consider himself lucky.

He grinned in the dark as he realized that his cock was fully stiff. He usually didn't wake up this hard until closer to dawn, but he hadn't relieved his balls in a few days, so he was probably pent up. He loved the feeling of being totally hard and throbbing, even if he couldn't do anything about it at the moment.

He was wondering if he'd have time while Dori took a shower in the morning, when he felt the blanket shift slightly and with a shock, he felt Dori's hand move over his hip.

"Just fucking great," he thought. "She's touching me in her sleep. Just like last night's kicking."

He was about to take her hand and guide it back to her side of the bed when he felt her fingers push slowly but firmly against his stiff cock through his pajama bottoms.

He was stunned, completely frozen by shock.

His own sister was feeling him up in her sleep, and despite being a bit creeped out by it he couldn't help but feel his cock respond to the heat of her fingers as they moved up and down along his shaft.

He wondered exactly how creepy it would be to pretend to stay asleep and see how long she touched him. Part of him was appalled by the idea, but feeling fingers that belonged to someone else touch him for the first time was almost too intense to pass up. Even if they belonged to his sister.

He resisted the urge to move his hips, concentrating on the gentle pressure as she tapped her fingers against him, causing him to throb to an even stiffer state of arousal.

Just when he didn't think he could stay still any longer, her fingers stopped exploring, and they pressed against him in the dark with neither of them moving. And then her hand moved and wrapped itself around him and squeezed, causing an involuntary groan to come out of his mouth.

Her hand let go of him and she quickly pulled it away.

For a full minute neither of them moved.

Harry was embarrassed at what he'd let happen, and that he'd enjoyed it to the point of making noise. But even as he worried about Dori being angry or ashamed next to him, he felt himself continue to throb with need and he realized his whole body was hot.

Had Dori been touching him in her sleep?

Was she still asleep?

Or had his groan awakened her?

Was she now wide awake in the dark embarrassed and ashamed as he was?

Or was she maybe feeling a bit aroused?

He didn't think that touching him in her sleep would have aroused her, but he couldn't understand or explain his own excitement. Nor could he make sense of the sexual thoughts he was having about Dori at that moment.

Finally, burning with both shame and curiosity Harry couldn't help himself.

"Are you awake?" he whispered quietly.

"I am now," Dori said softly. "What do you want?"

"You were touching me in your sleep," he answered. "It woke me up."

"You were dreaming," she said. "Go back to sleep."

"If I was dreaming you wouldn't have stopped," he said softly, knowing he was crossing a line but unable to stop himself.

She was quiet for so long he thought she's gone back to sleep, and he closed his eyes, willing to pretend that the past several minutes had never happened.

"If you hadn't made noise I wouldn't have stopped," she giggled. "I thought I woke you up and that you'd be mad."

"You were doing it on purpose?" he asked. "Why?"

"Are you mad?" she asked quietly in the dark.

"No," he said. "It just freaked me out is all. Why did you do it?"

"I was just curious," she said. "I felt it against my thigh last night, and I wanted to check it out a bit better, that's all."

"Isn't that weird?" he asked. "With your own brother?"

"Probably," she said. "But it's not like I get a lot of opportunities to feel a boner. And I'm sure you've been touched before. Just think of it like me accidentally seeing you while you were changing. This was just a braille look. Are you sure you're not upset?"

"I'm okay," he answered. "It surprised me is all. Even for a slut like you."

"Well your girlfriend must be very happy Harry," Dori whispered in the dark room. "I'm sorry I crossed that line. Let's just go to sleep."

"As if I can go to sleep like this," Harry laughed.

"Close your eyes and think of your girlfriend," Dori laughed.

"I don't have a girlfriend to think about," said Harry.

"That sucks," said Dori. "How long since someone's had sex with you?"

"Does my own hand count?" Harry asked with a chuckle.

"Of course not," said Dori. "Hands don't count."

"Then never," said Harry quietly.

"Are you serious?" said Dori, rolling onto her side to face him in the darkness.

"Yeah," said Harry. "How pathetic is it that the most sex I've ever had is my own sister groping me in the dark?"

"It's not pathetic," said Dori. "I feel bad for you, but it's not like there's anything wrong with being a virgin."

"I guess not," said Harry. "Although right now it sure feels like there is. It seems like I'll never be able to feel what sex is like."

"I'm sorry," said Dori. "I didn't mean to get things all worked up down there. You were sleeping so heavy I thought you'd sleep right through it."

"Did your curiosity at least get satisfied?" asked Harry in the dark.

"Oh fuck yes," she giggled. "To the point where I was jealous of your girlfriend, until I found out she doesn't exist."

"Thanks I guess," said Harry. "But don't you prefer girls?"

"I think so," said Dori. "I mean I've only ever had sex with girls. But I've always wondered what it would be like. That's why I felt you. I wanted to know what a boner felt like."

"I'm the opposite," confessed Harry. "I know what it feels like all too well. I want to feel what a woman's body feels like."

"How often do you use your own hand?" asked Dori, after a long pause.

"I don't know if I'm comfortable telling you about that," said Harry.

"I touch myself almost every morning," said Dori. "I even did it this morning while you were taking a shower. There's nothing embarrassing about masturbation Harry."

"I guess I do it every day," Harry admitted, unable to stop thinking about Dori touching herself with the fingers that had recently touched him.

"Did you do it today?" asked Dori.

"I didn't have a chance," Harry said.

"Not even in the shower?" asked Dori.

"The bathroom door wouldn't lock in the shitty motel room," Harry reminded her. "And I was afraid you'd come in and see me."

"I was too busy making myself cum," teased Dori. "Besides I thought it was sort of hot that you might be squirting your cum all over the shower floor I was about to stand on. That's one of the things I was thinking about while I did it."

Harry closed his eyes in the dark and felt his cock throb, ashamed to be having this conversation with his own sister, but even more ashamed of how much it was turning him on.

"You should have told me," he whispered. "I really wanted to, but I was afraid you'd think I was a degenerate. Besides I thought I'd have my own room tonight."

"Me too," said Dori. "I was going to find a place tomorrow and buy a vibrator. You know, to fuck myself with in private."

"You've never done that?" asked Harry. "I thought you lesbians all used sex toys."

"All of us huh?" Dori laughed. "I never have. Debbie is very oral so that's what we always do. I wish she was here now."

"Why?" asked Harry.

"Because feeling you made me wet, and this conversation is turning me on," Dori giggled. "Her mouth and tongue would really be a big help right now."

"I wish she was here too then," said Harry.

"Oh yeah?" asked Dori. "You'd want to watch?"

"Fuck yeah," said Harry. "It would give me a good excuse to jerk off."

"Being horny is a good enough excuse," said Dori softly. "You can if you need to."

"Isn't that weird?" asked Harry.

"You just said you were willing to do it if my girlfriend was here," Dori teased him. "All of the sudden you're too embarrassed to do it if it's just the two of us?"

"That's different,' said Harry. "That's just a fantasy. Besides, in that fantasy you'd be getting off too. It wouldn't be just me."

"So it would be okay if we both got off?" asked Dori.

"I guess, yeah," Harry answered. "But isn't that super creepy? A brother and sister masturbating together in the same bed? What would Debbie think?"

"I'll tell you about Debbie and her brother someday," said Dori. "I think he's the one who gave her the oral fixation."

"Really?" asked Harry, his eyes wide and his cock throbbing in the dark.

His hand was on his stomach, as he desperately fought the urge to push it into his pajama pants and stroke himself.

"If you really don't want to that's okay," said Dori. "But if you do want to, I'm sort of pent up too and think it would be really hot if we both came."

"Are you sure?" asked Harry, unable to disguise his hope.

"Go ahead," whispered Dori, her voice catching. "I'm touching myself."

"Fuck," groaned Harry, unable to keep his hand from pushing through the elastic band of his pants and gripping his cock.

He squeezed it as hard as he could, feeling the tip flex out a bead of precum against the cotton fabric it was straining against.

"Are you doing it?" Dori panted. "Are you hard again?"

"I've been hard this whole time," Harry said. "I can't help it."

"Does it feel good?" asked Dori. "Are you totally hard?"

"It's throbbing," said Harry. "It's really hard."

"Can I see?" asked Dori. "Just a look?"

"If you want to," said Harry, feeling his cock jump in his hand at the thought of her looking at him like this.

Dori grabbed her phone and thumbed the flashlight on, and Harry pushed the blankets down so she could see the way his cock and fist were tenting his pants.

"Can you take it out for me?" she whispered.

Without a word he pushed his pants down, and as the elastic pushed over his cock it bent down along his thigh, until it was suddenly free and popped back up.

"Wow!" Dori panted as it sprung up into view.

She stared at the stiff erection, fascinated by the blue veins that were even more visible in the bright white light of her phone.

Suddenly desperate to do it in front of her, Harry grabbed himself again, and started to slowly pull his hand up and down along the shaft.

Dori put the phone on the bed with the light aimed at the ceiling, and the entire bed was dimly lit in the soft white light. Harry glanced at her and saw that she was staring at his cock as she pushed her hand back into her own gym shorts.

"You made me so wet," she moaned. "Fuck that looks so fucking sexy."

"Can I see?" Harry asked, his arousal making him bold.

Dori pushed her shorts down her legs and kicked them off, settling back besides him with her hand between her legs.

She looked over at Harry and their eyes locked.

"I can't believe we're doing this," Harry said.

"Remember," she said with a wink, "hands don't count."

He stared at her arm moving as she touched herself, stroking himself slowly as she watched him.

"Looking at you makes me so horny," Dori whispered with a giggle. "Isn't this hot?"

"It is," he agreed with a grin. "Even though I can't really see any of your good stuff."

She reached over and grabbed his wrist and pulled his hand to her body as she slid next to him. She pushed his hand against her inner thigh as she fumbled to turn the phone light off, and then pulled Harry onto his side as she pressed against him.

"Feel my good stuff then," she whispered.

His hand settled against her, and she shuddered at the heat as he pressed against her slick crease. He moved his hand up and down, and then used his fingers to probe along her soft lips, and she grabbed his arm and rolled her hips.

"Oh fuck," she whispered in the pitch-black room.

"Is this okay?" he asked softly, his fingers probing and touching her everywhere he could.

"It's beautiful," she gasped. "Do you want to make me cum?"

He didn't answer, instead he pushed two fingers up into her wet heat, and then pushed them along her lips until he found her clit. He pulled at her lips and started to move his wet fingers along either side of her stiff bud, stroking her in the same rhythm of her rocking hips.

"How do you know to do it that way?" she whimpered.

"I read a lot," he said, fascinated by how it felt to get his fingers slippery with her arousal and then drag them over her tiny stiff clit.

"Just like that," she gasped. "Just like that and I'll go off for you."

He started to move his fingers faster and she dug her nails into his arm.

"Slower," she begged. "Like you just were. A nice slow touch and I won't be able to hold back."

He resumed his earlier stroking speed, loving the feeling of her hot body against his. He wanted to feel her breasts and taste between her legs and move his hands all over every inch of her skin, but he realized that she was too close to the edge for him to try anything but what she was letting him do.

He resolved to just enjoy this for what it was and to savor it as much as he could in case he never got a chance to do any more, deciding that he could enjoy her pleasure as much as his own.

He didn't have long to savor it though, because after just two more minutes of quietly moaning in his hear while rocking up and down with his fingers, she seemed to press closer to him and dug her fingers into his arm so hard he was sure he'd be bruised.