Late Night Truth or Dare Ch. 04

The three laid naked, their bodies pressed against each other, as the siblings played with Ashley's chest, no longer with a sense of urgency.

They knew they had all day to play together, and now they'd all had at least one orgasm that morning, and they were satisfied with enjoying each other's company. And their naked bodies.

Eventually, Ashley looked at Bobby and asked, "Shall we start her education?"

"Education? I don't think I like the sound of that," Sarah responded.

"Oh. I think you'll like this," Bobby said with a smile.

Bobby repositioned himself, propping himself on his pillows with his dick rising from his lap.

The girls sat on their knees near the foot of the bed, staring at Bobby. They admired his toned body and thick cock. They both knew how lucky they were to be able to sleep with such a man.

They were both stunning in their own right, but up until Bobby, they'd been relegated to high school boys. Well, Ashley had been. Sarah had never made it very far, even with them.

"Bobby said you wanted to know how to deep throat," Ashley look at Sarah.

"I do, but I'm not sure I can. My gag reflex kicks in way too easily."

"Don't worry. It might not happen today, as it takes practice, but you'll get there."

"How'd you learn?"

"Honestly? I practiced on breadsticks, carrots, even my fingers, and eventually a dildo. I always knew it was something I wanted to do, so I set out to make it happen. But you have a real live cock right down the hall from you. You won't need anything besides determination and a willing brother."

"I am sure he won't mind me practicing," Sarah winked at Bobby.

"Are you ready to give it a shot? Don't expect to get it all in today. Whenever you're ready, I'll guide you as much as I can," Ashley reassured her friend.

Sarah leaned forward, lowering her face near her brother's cock. She could see it twitch with anticipation as the skin of his balls contracted, drawing his testicles closer to his body.

Her heart was racing, not because she was nervous about giving Bobby a blow job, but because she was scared of failing.

He'd be able to directly compare her to Ashley, who not only was a pro at oral sex but had a massive set of tits as well.

No matter how many times Bobby assured her that he liked her small breasts, she was still worried he preferred Ashley's.

Taking his shaft in her hand, she pulled it vertical and slowly lowered her mouth over it. She licked the tip, tasting his precum, as she breathed deeply, trying to gain the courage to push past her limits.

"Take it slow. Don't bite off more than you can chew," Sarah said calmly.

"Don't bite off anything," Bobby joked.

"Breathe through your nose and slowly take as much in as you can. Stop when you first feel your gag reflex kick in."

Sarah slipped her brother inside, centimeter by centimeter, not wanting to push too deep. Soon she was halfway down his rod and could feel his thick head pressing against the roof of her mouth. She thought she could take more and pushed her head down lower.

This was a mistake.

Her gag reflex kicked in hard, causing her to dry heave as she quickly pulled away from her brother. She sat up coughing, saliva dripping from her mouth and her eyes watering.

She worried she wouldn't be able to do this.

"That's okay. You went too fast, but now you know your limit," Ashley encouraged. "Catch your breath and try again when you're ready."

It did not take long before Sarah was slowly bobbing on her brother's dick. Once again, creeping lower and lower, but this time she stopped when she felt pressure at the back of her mouth.

She was not gagging, but it was uncomfortable.

"That's it. Hold him there for a minute. Let yourself get used to the sensation. Keep breathing through your nose." Ashley's voice was calm. "When you're ready, push slightly deeper. Take it to the point that you think you can hold for a minute."

Sarah followed Ashley's instructions and held Bobby deep in her mouth for a minute, then two, and finally had to pull herself from him as she closed in on three minutes.

She left his cock coated in saliva, a string attaching her lips to his head. He enjoyed the exercise, but Sarah knew he'd prefer Ashley's mouth to hers.

This only made her more determined to fit all of him inside her. Without instruction, she lowered her face and took her brother inside her mouth again. Soon she had him as far as she could tolerate, and her eyes began to water.

"Swallow," Ashley said. "Swallow when you feel it is too much. It causes your body to accept the object in your throat."

Sarah did as she was told, swallowing every time her brother's cock felt like it was too much.

To her surprise, it worked, and she was able to hold him at the back of her mouth for almost five minutes while she gently bobbed up and down.

She knew it was not the best blow job, but Bobby wasn't complaining.

He was clearly willing to allow her to practice on him.

"You can also hum if you like. That opens up your throat, especially if you try to hit a high note while doing it." Ashley added. "Also, guys love the vibrations."

"I'll keep that in mind," Sarah responded while catching her breath, drool running from the side of her mouth.

"It is going to take time and practice, but I can also show you a few positions that will help out," Ashley continued. "Take a break, and let me show you how it's done."

Ashley got on her hands and knees in front of Bobby. Sarah shifted to the edge of the bed, looking on with curiosity.

"Sit on your knees," Ashley instructed Bobby.

"As you wish," Bobby responded.

Bobby's cock curved away from him, bouncing in front of Ashley's face.

She reached out and grabbed it, feeling the lingering wetness from Sarah's mouth. She stroked it a few times as she glanced over at Sarah, worried she'd be jealous.

Instead, she seemed fixated on learning as much as she could.

"You see how my mouth lines up with my throat when I tip my head back in this position?" Ashley asked rhetorically. "It will make it easier for him to slide past the back of my tongue."

Ashley took Bobby in her mouth and quickly slid three-quarters of the way down his shaft, further than Sarah had made it. She reached up with one hand and grabbed his ass, pulling him towards her face.

He got the hint and reached down and grabbed the side of her head, holding her steady as he slowly face-fucked her.

Sarah sat with her mouth agape, unable to understand how her friend took all of her brother so easily. It was a sexy sight, but it intimidated her.

Even if she could deep throat him, she doubted she'd be able to let him do this to her.

Bobby picked up the pace as Ashley's hand urged him on. Soon he was violently bottoming out against her nose, his head slipping past her tonsils with each plunge.

He could feel the cum swelling in his balls. If Ashley continued, he'd soon be making her choke on his cum.

Ashley pulled herself from his cock, sitting back as she wiped the drool from her lips.

"See how easily it goes in? I love it when a guy fucks my face, although it can be hard on the neck. Don't let your brother get too rough." Ashley stretched her neck to one side. "Another version is to lie on your back with your head hanging off the side of the bed. This also aligns the throat and helps with cocks like Bobby's. You see how he curls back towards his body a little? While on your back, that bend aims his head down your throat. The downside is that you don't have control over depth in this position, so maybe don't try it until you have your gag reflexes under control."

"I can let you guide me inside your mouth with your hands. You can just reach up and grab my ass. I promise not to go any deeper than you pull me," Bobby said to his sister, "but it's probably best to keep it simple at first. Work on tolerating the sensation, and then we can get to the fun."

"I just hope I can master this before leaving for college," Sarah sighed.

"So you can give the best blow jobs in your dorm?" Bobby teased.

"No, you idiot, so I can feel you cum down my throat." Sarah looked her brother in the eyes. "I want to swallow every last drop of your seed."

"Okay, okay. There's one last position that I like," Ashley interrupted, "good ol' fashioned sixty-nine. With the girl on top, it gives her control. It does not line up the throat as nicely as the others, but it is better than how you attempted earlier. Also, once you gain confidence, you can let him be on top. There is nothing quite like getting your throat fucked against the mattress."

"Let's stick to you being on top, for now, Sarah," Bobby said, giving Ashley a bit of side-eye. "I think Ashley has some kinks that may exceed yours."

"I don't know. I think I might like to try that when I'm ready," Sarah smiled.

"Are you ready to try again?" Ashley asked Sarah. "I'm not sure what else I can tell you, but practice makes perfect."

"Not right now. As you said, I can practice on Bobby almost anytime. I think that it's time to repay you for your help." Sarah gave her friend a wicked smile. "Get on top of me."

Ashley instantly knew what her friend was talking about, climbing on top of her in a sixty-nine position. As she lowered her face to Sarah's snatch, her own cooch received a kiss from Sarah's lips below.

Bobby sat back and watched as the girls ate each other, seemingly oblivious to his presence. He wasn't sure if he should enjoy the show or join in.

"Are you going to fuck her or what?" His sister called out between laps of her friend's clit.

Bobby positioned himself behind Ashley. He rubbed his cock along her slit before pushing it down so his sister could take it into her mouth, lubricating it as she teased him.

Bobby's hips pushed forward, and he buried his cock into Ashley.

"Oh fuck yes, this is amazing," Ashley called out.

The siblings fucked and licked their friend, not letting up until her body shook from orgasm and her hips were grinding into Sarah's mouth as Bobby held on from behind.

As Ashley collapsed on top of her friend, Sarah and Bobby rolled her onto her back. Sarah straddled her face as Bobby reentered her. The siblings kissed as a literal love triangle took shape.

Sarah reached down and placed her palm on Ashley's lower stomach, just above her pelvic bone, as she slipped her fingers over her clit.

Bobby pressed one hand into Ashley's breasts, squeezing her soft flesh between his fingers. He sensually slid his other hand up his sister's side until he found her nipple. He pinched and teased her as he kissed her intensely.

The siblings focused on each other as they fucked their friend below them.

Ashley didn't mind. She like being used by the pair. She knew she'd get another orgasm and discovered that the pressure they placed on her was a huge turn-on.

As much as she liked being in control, she'd gladly be used as a prop in any sexual game these two wanted to play.

She moaned as she returned her attention to eating out her friend, with Bobby's cock filling her cunt with every thrust.

Ashley knew she was growing closer to a second orgasm, but she wanted Sarah to share in her pleasure. She grabbed her friend's hips as she focused her energy on giving her the best pussy licking she could.

Sarah responded by grinding into the face below her. A moan escaped her lips as she broke from the kiss with her brother.

Ashley knew she had her on the verge, which was good because she was about to cum herself.

Ashley slipped her fingers between Sarah's butt cheeks. Ashley didn't know how Sarah felt about ass play, but she knew a little tickle of the sphincter always did the trick when she needed a nudge herself over the cliff.

Ashley's finger found its way towards Sarah's brown eye, unaware of what her friend had discovered with her brother. Pressing against it, Ashley felt Sarah jerk on top of her, Sarah's weight crushing down on Ashley's face as she came.

"I'm cumming. Bobby, make her cum for me," Sarah called out, rubbing harder against Ashley's clit. "I want to cum together."

Bobby let go of each girl's breast and grabbed Ashley's legs. Pushing them back, he focused on fucking her hard and deep.

He was near to orgasm himself, but he knew Ashley was closer. He could feel her cunt contracting around his member as they both rocketed towards a mutual climax.

Sarah collapsed back into the pile of pillows as she finished her orgasm. She'd wanted to cum with the others but getting to watch them finish together was a nice consolation prize.

She reached down and grabbed Ashley's breasts, squeezing them hard as her friend shrieked in excitement.

"Fuck me harder, Bobby. Make your sister watch me cum all over your cock. Fill me with your seed," Ashley commanded.

Bobby obeyed, not that he'd thought of doing any different.

The thought of pulling out and shooting over her tits had long passed. He'd cum in four unprotected teenage cunts. What was one more?

His cock twitched, jerked, and then unleashed a torrent of semen into Ashley as she writhed on the bed below him. Their bodies were connected only at the groin, but their orgasms were in perfect sync as they stared into each other's eyes.

If it was not for his sister, Bobby could have fallen in love with this girl.

She was already in love with him.

He had a special connection with Ashley, as he did with Candice, but it paled by comparison to what he had with his sister.

He didn't know what any of it meant, but he was eager to enjoy it while it lasted.

He hadn't spent as much time with Bella or Dee, but he knew it was coming. He figured he better get to know them, as they might be carrying his child. He hoped not, but he knew it was a possibility.

As his cock finished producing any more spunk, his legs grew weak, and he lurched forward, collapsing on top of Ashley.

They kissed each other in post-orgasmic bliss, only to look up and see Sarah's well-licked pussy staring them in the face.

"Are you two up for another round?" Sarah asked as she slid two fingers inside herself.

"Give me a minute," Bobby said, exhausted. "I'm not sure I can rally for another round."

"Come here," Ashley told Sarah, pushing Bobby off her. "I have a cunt full of cum for you to lick."

Bobby lay on his back, his cock deflating on his stomach as his sister crawled between her friend's legs, lapping up his jizz as it oozed from her lips.

Two weeks ago, this would have been the hottest thing he'd ever seen. Now he struggled to find the motivation to prop himself on his pillows and watch.

Though watch he did. His cock grew hard as his sister moved from her friend's crotch and met her lips in a passionate kiss, swapping the remaining sperm between their mouths.

Bobby didn't know how much energy he had left, his body still felt weak, but his cock was ready for another round.

The girls noticed, with Sarah straddling his member as Ashley sat on his face. Bobby once again found himself impaling his sister, but this time her friend's pussy was smearing its lube all over his mouth as he searched for her clit.

She still tasted faintly of his semen, but he'd grown used to the flavor.

He'd dreaded coming home for the summer, anticipating it would be the worst months of his life. Now, he wished he didn't have to go back to college.

He could spend the rest of his life in this position, and the girls were more than happy to oblige him. Hell, there were three other girls willing to join in the fun.

It was almost too much for him to take.

Almost.