Late Night Truth or Dare Ch. 04

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Candice regained her poise and gripped his hair with her hands, not guiding him, but massaging his scalp as he worshiped her.

She'd always been self-conscious about her small breasts, constantly comparing herself to Ashley and Dee, but that dissipated when she was with Bobby.

He didn't seem to care that her breasts were smaller than her friends—almost non-existent in Candice's mind—and he'd slept with all of them, so he knew what he was missing.

She didn't know how he compared her body to Ashley's, but the fact she still felt worshiped by him eased her jealousy. Who would have thought the way to begin to get over her body issues was to sleep with the same guy as four of her friends?

Candice moaned as Bobby took her left nipple into his mouth while pinching down on her right. She gripped his hair and held his face tight against her chest as he sucked and tweaked.

She'd never had a guy play with her nipple like this. Then again, she hadn't had a guy do much of anything to her before Bobby.

"Kiss me," Candice begged, pulling his head towards her mouth.

Bobby slid up her body, his hard cock, still contained in his underwear, pressed against her engorged groin. She'd calmed down from her orgasm, no longer super sensitive, and she was ready for more.

She always wanted more.

Candice was confused about the stereotype that boys were horny while girls were not. Everyone spewed stats about how often guys thought about sex, but she was constantly thinking about it.

In class, she'd get distracted by daydreams about the hot guys sitting near her. She'd imagine them doing all sorts of naughty things to her, but she never thought one of the hottest guys she knew would be on top of her naked body. Again.

Bobby had always been attractive and utterly out of reach. Not only was he the brother of Sarah, but Ashley had all but called dibs on him by continuously talking about her crush.

None of them thought they'd stand a chance with Bobby, and if anyone was going to get him, it was Ashley and her perfect breasts. It turned out that all they needed to do was make the first move.

Still kissing Candice deeply, Bobby reached down and pushed his boxer briefs as far down as he could before inching them the final portion with his foot. He kicked them to the side, holding his body above Candice's, his erect cock dripping precum as he realized he'd forgotten to bring condoms.

Sensing his hesitation, Candice reached down and grabbed his shaft, pulling him towards her slit.

"You owe me a cunt full of cum. Remember?" Candice whispered in his ear.

"Are you sure? I don't want to risk getting you pregnant."

"It'll be okay."

Bobby knew better. He should have resisted the temptation and asked for a blow job instead, but that was easier thought than accomplished.

He was being drawn inside her. Physically by her hand and subconsciously by an overwhelming desire to fulfill the teenager's perilous wish.

He'd fill her with cum. He'd done it to his sister, Dee, and Bella already. What was another potential pregnancy amongst the five?

"God. You're so tight," Bobby said as his head popped between her lips, "it feels so good to be inside you."

"Go slow. You're nearly too big for me."

Bobby complied, easing himself into Candice, his cock filling her inexperienced canal with his impressive girth. He paused, holding himself inside her as he leaned forward to kiss her.

They swapped spit as Bobby slowly pushed further in. Only slightly at first, but soon he was almost all the way inside. He went slowly, not wanting to rush things, knowing he'd cum too quickly if he fucked her the way he desired.

Candice's fingers scratched along his back, leaving red trails as she went. She wanted more, for him to fuck her harder, but she was scared to ask.

She'd been on top their first time, allowing her to control the situation. Being underneath was different. It was scary. She'd have no recourse if he was too rough.

She trusted him but was still nervous that he wouldn't stop if she asked. She'd heard some guys wouldn't stop. Even so, she wanted to feel him pound inside her.

"Fuck me harder, Bobby," Candice said nervously, "just don't hurt me."

"Let me know if you need me to stop," Bobby replied, easing many of Candice's nerves.

Bobby sat back on his knees, still inside her, as he grabbed her legs and pushed them back until her heels pressed against her ass. She maintained a strict stretching routine for running, so her thighs easily pressed past her chest as he leaned into her.

As her pelvis tilted up, his cock thrust against the roof of her vagina.

"Oh fuck, that's so deep," Candice moaned, "don't stop."

Placing his weight on her legs, Bobby slowly ramped up the intensity. His balls slapped against her ass. The skin of his testicles stuck to where her fluids had run down and coated her crack and cheeks, only to peel free as he withdrew from her.

"Keep going, just like that," Candice begged.

Bobby did not change his stroke, resisting the urge to fuck her harder and faster, knowing that wasn't what she asked for. Instead, he reached one hand down and placed his thumb on her clit, rubbing as his pace held steady.

He gently increased his force as she responded well to the extra stimulation.

Her body started to shiver, and her skin grew goosebumps as Bobby kept fucking her. He knew she was getting close because her face was contorting, looking like she was about to sneeze.

Bobby fixed his eyes on hers, desperate to watch as she came.

"Yes,. Oh yes. Fuck me!" Candice screamed.

Her head flung back as her body tensed and went rigid before arching her back. Bobby did all he could to maintain his rhythm and depth as she began to spasm and flail beneath him.

He couldn't remember such a show during their first encounter, but most of that night was a blur.

Her cunt gripped his cock, begging for him to unleash inside her. He was close, and as soon as her climax subsided, he leaned forward, wrapping his arms around her.

With one arm under her back and one under her head and neck, he fucked hard, not trying to maintain composure, only trying to cum.

His balls were full, and his desire was over the moon. Any trepidation about impregnating her had long left his mind. All he could think about was cumming, and cumming hard.

"Oh fuck. I'm gonna shoot," Bobby said before letting out a loud hybrid of a grunt and moan.

"Fill me up. Fill me with your baby juice."

Candice didn't know where that came from. While she'd wanted to experience what it was like to have a guy ejaculate inside her, she didn't want to get pregnant.

She'd planned to go on birth control in college and wanted to get Plan B if she ever got creamed by Bobby. Now she realized that she might want something different. She might want his baby.

She knew Sarah had taken precautions but wasn't sure if Bella or Dee had fulfilled their promises to Bobby.

There was a discussion to be had and consequences to consider. Having a child seemed like an ordeal, especially during her first year in college. On the other hand, who better to do it with?

Bobby was graduating soon and could support the kid, and she'd be forever tied to Sarah's family. Or maybe this was all lust. She obviously couldn't trust her judgment while Bobby was orgasming inside her.

It'd ruin her track scholarship if she was pregnant, and that was something she couldn't risk.

Bobby's cock jerked as sperm shot forth, filling Candice as she'd begged for. Bobby knew he'd have to talk to her, but it could wait, as he was in heaven.

He wasn't sure if he could return to fucking with a condom. The sensation was so much better when it was skin to skin. It's not that it just made the orgasm better, but the connection was somehow deeper.

The condom created a barrier not just against pregnancy and STDs but against a more profound emotional union. Preventing the bonding you experience when you fully commit to someone.

Was there a stronger commitment than cumming inside a fertile eighteen-year-old?

Bobby collapsed to the side, his slick cock flopping against his stomach, with the last few drops of his cum leaking from the tip. He was exhausted and breathed deeply as he stared at the ceiling.

He was about to reach over and pull Candice against him when he felt her kiss his abs a few inches above his slowly deflating dick.

Candice inched closer to his head before reaching out with her tongue and licking the few drops of sperm left dangling. She gently took him into her mouth, careful not to apply too much pressure to his head as she attempted to clean their combined fluids from him.

It was not enough to keep him hard, but Bobby appreciated the gesture, and it felt good, even if it didn't lead to anything more.

"So, what do you think of the outfits?" Bobby asked.

"I think they would all look good on Sarah," Candice replied with a hint of sadness.

"They all looked good on you."

"Well, I picked the colors that worked best for my skin color."

"I know. I bought those for you," Bobby smiled, knowing Candice hadn't expected the gifts, "I'll give the others to my sister."

"Good, because I don't think I can give up this schoolgirl outfit," Candice joked, hiding how happy she was to now own sexy lingerie. "Thank you."

"That's my favorite as well."

Candice stood, still wearing the minuscule skirt from the schoolgirl uniform. Cum ran down one leg and dripped to the floor from her knee.

Bobby admired her exposed ass as she intentionally swayed her hips as she walked towards the shower.

She stopped and looked over her shoulder, her eyes meeting Bobby's.

"Want to join me?"

*****

Bobby: I left you a gift on your bed.

Sarah: What is it?

Bobby: It's an apology. I want to talk when I get home.

Sarah: Good or bad?

Bobby: I think you'll like it. Just open the box and read the note.

Bobby walked through the front door, not knowing what to expect. He'd left a box of lingerie as an apology gift to his sister, but without further discussion, it wasn't clear how she'd take it.

She was pissed because he didn't want to sleep with her anymore. He'd cited the risks involved but never explained his true feelings.

He still longed to press his naked body against hers and slip himself inside her as she gazed deep into his eyes. This hadn't changed.

He thought of her as the perfect woman for him, better than any of her friends but social norms consumed his thoughts regarding the ethics and morality of the situation.

He couldn't get past the fear of getting caught and what people would do to them if they knew they were lovers. Specifically, what would happen to Sarah?

No matter how much he resisted, he wanted to see her in the lingerie, even if he couldn't touch, kiss, or fuck her.

"Hey there, stranger, I like your gift," Sarah said as she posed against the door frame leading to the kitchen. Her hands gripped the wall above her head, elongating her already slender body. "Does this mean that you do want me?"

She was wearing the more conservative yet still sexy bodysuit. The white fabric clung against her pale skin with the crotch pulled taut against her cunt. It slipped between her lips as she stretched her arms higher.

She wasn't practiced at seduction and was only imitating what she'd seen in movies, but her efforts disarmed Bobby.

"Sarah," Bobby paused, thinking carefully about how he wanted to respond. "I haven't been able to stop thinking about you since you crawled on top of me, but I don't want to see you get hurt. I'm afraid that if the wrong people find out about us, then our lives will be torn apart. That your reputation will be destroyed. That you'll never find a husband, never have kids, and worst, we'll never get to be together."

"Oh, Bobby, you're so stupid sometimes. No one's going to find out. How would they? If we're careful and only mess around when Mom and Dad are at work, then who'll be the wiser?"

"Your friends already know. Are you sure we can trust them to keep a secret?"

"You trust them enough to risk impregnating them. Doesn't that give you the answer?"

"That's different, that's—"

"Is it? Do you think our relationship would ruin your life more than impregnating four teenage girls?"

"But it wouldn't ruin yours."

"Despite what Mom and Dad think, I can make my own choices. I knew the risks of hooking up with you from the start. It's something that I've been thinking about for a long time, and I did not enter into this lightly. Let me decide what risks I'm willing to take, and I'll let you choose for yourself," Sarah paused. "Am I worth the shame if we get caught?"

"Hell, what's the worst that can happen? Mom and Dad disown us, and we can never return to our hometown? I don't care about coming back here anymore. I'd miss mom, but I'd prefer to be with you."

"So?" Sarah drew out the question, waiting for her brother's response.

Bobby didn't say anything. Instead, he stepped forward and kissed her, pulling her into his arms as they wrapped tightly around her. His hands slipped to her ass, her exposed cheeks firm in his grip as she dug her fingers into his back.

Neither knew why they'd delayed having the conversation.

They hadn't even said much, and all that was needed was for Bobby to realize he wasn't responsible for his sister's actions.

They stumbled up the stairs, not wanting to let go of each other. They somehow made it to Sarah's room before collapsing on her bed with Bobby's clothes already half off.

His face was quickly between her legs, with the snap of the bodysuit's crotch undone and exposing her sex to him.

"We don't have much time," Sarah panted, not wanting him to waste time before fucking her.

"Shut up and let me eat you out," Bobby responded.

"We don't have time. Mom said she'd be home around three today."

"In that case . . . " Bobby responded as he stood and stripped the rest of his clothes.

He crawled onto the bed, looming over his sister as she lay back, the crotch of the bodysuit bunched around her waist, but the rest still tight and sexy on her chest.

Her legs were spread, waiting for Bobby to enter her, waiting for his cock to penetrate her freshly shaven cunt.

"Do you like it?" Sarah asked.

"I do, but I liked it before as well. Either way, it feels amazing around my cock," Bobby said as he slid inside his sister, re-consummating their start-stop relationship.

He was now confident she wouldn't regret sleeping with him, but he was still unsure how they'd make it last after leaving for college in a few weeks.

*****

"Are you still okay with me messing around with your friends?" Bobby asked his sister, who was curled against his chest.

"Of course. You know I'm not the jealous type. Plus, I love those girls and want to share as much as I can with them," Sarah responded without hesitation. "Why?"

"Oh, just because Ashley should be here in a few minutes."

Sarah had snuck into Bobby's bed after her parents had left for work, but she wasn't aiming to have sex.

She'd woken up alone and desiring skin-to-skin contact. Inevitably her brother ended up inside her, which she didn't complain about as it wasn't a poor way to start the day.

Now they were naked in each other's arms, neither of them in a hurry to separate.

"Should I leave?" Sarah wondered aloud, hoping the answer was "no."

"Of course not. I asked her to come to help you out."

Sarah looked at her brother with confusion.

"You'll see," he answered.

"Oh, I will, will I?" Sarah joked as she climbed on top of her brother and kissed him.

She could feel he'd recovered from their earlier escapades as she ground against him.

"You two couldn't wait to get started without me?" Ashley asked as she stood in the doorway and watched the two siblings rub against each other.

Sarah rolled off her brother to see her friend wearing a baggy t-shirt and loose pajama pants like she'd just gotten out of bed.

Ashley was staring at Sarah and Bobby, her hand down the front of her pants, her masturbatory efforts clear through the cotton fabric.

"Don't stop on my behalf. It was just getting good," Ashley joked.

"I'm glad to see you dressed up for the occasion," Sarah chirped back.

"Why bother? I figured I'd end up naked like you two."

"Then what are you waiting for?"

Ashley pulled off her shirt and pants, revealing a lack of bra and underwear, before jumping into the bed.

Bobby had invited her for a specific purpose but it was quickly forgotten as passion took over when all three intertwined their bodies.

No one cared where their passions took them. Each of them sucking, fondling, and thrusting into various body parts. It took several minutes before any of them knew what was happening.

When the dust settled, Bobby was on his side with his head between Sarah's legs. His tongue pressed against her clit as he fucked her with his thumb.

He'd said he was indifferent to her choice in pubic hair, and visually he was. But in this position, he quickly learned the benefits of working on a clean canvas.

There was no hair sticking between his teeth and interrupting his task. Sarah ground against his face in response to his efforts, but her usual moans of pleasure were absent.

Bobby's cock was deep inside Ashley's mouth with her sucking inching him closer to orgasm, but his own oral efforts kept his climax at bay.

He was amazed about how much concentration it took to cum, even when a skilled practitioner such as Ashley was servicing him.

He knew she could make him cum whether he wanted to or not. He was just surprised about how much easier it was to hold off when you had something else to focus on.

It was the gift and curse of sixty-nine.

Ashley's tongue swirled around his tip as she pulled him from her mouth, catching her breath before plunging him back into the depths of her throat.

She too was distracted. Only giving part of her attention to blowing Bobby, as Sarah's face was between her legs.

Sarah's tongue deftly maneuvered around Ashley's clit as she penetrated her with two fingers. Sarah had always been the best at eating pussy amongst the girls but Ashley didn't know if it was because of desire or inherent talent. Maybe she was the best at translating what got her off when going down on the other girls.

The three of them were on their sides in an oral sex daisy chain. Each satisfied the next as they were pleased by their predecessor. A triangle of oral stimulation that wouldn't stop until at least one of them came.

All three tried to get their target off, wanting to end the cycle not by cumming themselves but by providing the orgasm.

Ashley was the first to crack.

"Oh god, yes, yes, yes!" she said as she pulled her face from Bobby's dick.

"Keep going, Sarah, make me cum. I'm going to cum."

Bobby took this as a sign to stop eating out his sister, moving instead to suck on Ashley's massive tits.

Now flat on her back, Ashley continued to call out as Sarah worked between her legs while Bobby's mouth sucked on one nipple as his hand gripped and massaged the other plentiful breast.

The stimulation was too much for her to take as she let out a deafening scream that was sure to catch the attention of the neighbors.

"Fuck guys. That was amazing. We should do this more often," Ashley said, still out of breath.

"Any time you want," Sarah said as she slid up her friend's body, sucking Ashley's free nipple into her mouth.

The siblings each worshiped one of Ashley's gorgeous tits.

"I'm going to miss you guys at college," Ashley mused.

"You can visit either of us any time you want," Sarah replied.

"Yeah, but not both of you at the same time."