Penny & Ryan Pt. 01

[Author's note: All characters in this story are 18-years and older.]

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Ryan & Penny

Ryan was at his desk, searching for some songs on his computer, when he heard a rap on his open bedroom door, behind him.

"You busy?" his step-sister, Penny asked, as she walked in.

"Not really," he answered, "What's up?"

"I wanted to show you something," she said, sitting down on his extra chair, and navigating to a video on her phone. She held the phone out to him, and when he took it and saw what was playing on the little screen, his mouth dropped open.

There, in full color, and hi-def sound was a video of him sitting in front of his computer, completely naked, his hard cock in his hand, jerking off while watching a group-sex porn video on the screen in front of him.

"That was last Saturday," she said. "I guess you thought we were all gone to the mall, probably. But I changed my mind, and Mom and Dad dropped me off at the mailbox, and I walked back. I guess you didn't hear me come in, huh?" Her tone was matter-of-fact smug; a tone that he knew all too well.

He could tell that the video had been shot from near the floor, at the edge of his doorway. She had probably been lying on her stomach, out in the hallway to take it.

It wasn't up close and personal, and the view was partially blocked by the arm of the chair, but you could sure see what he was doing, well enough.

As she took the phone back from him, she watched a little more of the video, and said, "Boy, think how embarrassing it would be if this were to end up on YouTube, or something."

"What do you want?" he said resignedly.

It was hardly the first time she had blackmailed him. Although they generally got along pretty well, but at 19 to his 18, she was the older sibling, and she always knew when she had an upper hand and she wasn't afraid to exploit it. Over the years, he had done her chores, "shared" his allowance, and even let her use his car, all to keep from getting in trouble with their parents ... something he seemed to have a knack for doing.

"Three things, actually," she said.

He groaned.

"First," she said, "I want to watch you do it, again."

"What!?" he said. "No way! You didn't get enough video the first time?"

"No camera," she said, setting it on his desk, and covering it with his notebook. "I just want to watch, up close. I thought it was hot as hell to see you doing that."

That was certainly not the direction he expected this to take.

"I don't think I could even get it hard with you sitting there watching me," he said. "It'd be too weird."

He had had plenty of sexual fantasies about his slightly-older step-sister since he reached puberty, but jerking off while she watched him wasn't one of them.

"Maybe you could get hard if you had inspiration," she said. She crossed her arms, grabbed the bottom edge of her t-shirt, and pulled it off over her head in one smooth motion.

Again, his jaw dropped open, as he stared at her naked tits, less than two feet from his face.

"I know you've been sneaking peeks at my boobs since they started growing," she said, cupping them in her two hands. "It's actually a little flattering to know you like them that much." She gently rolled the nubs of her nipples between her fingers and thumbs.

"Come on," she said with a grin, "I showed you mine, you show me yours."

He lifted his butt off the chair, and had his pants and shorts around his ankles in seconds. His stiff erection stood up, fully inspired!

"Stroke it," she said, still massaging her tits.

She needn't have told him; his hand was already on its way there.

After a few slow strokes up and down the shaft, while he just stared at her tits, he took a moment to spit in his hand to use as a lubricant—like he'd done a thousands times since discovering what jerking off was.

As he slid his hand, back and forth, over the head of his hard cock and down to his pubic hair, Penny let out a long sigh, and pulled harder on her nipples. "That is so fucking hot!" she said staring intently at his glistening cock as his hand slid slowly up and down its length.

"Does Greg do this for you?" he asked, referring to her boyfriend, but not taking his eyes off her gorgeous tits and the nipples she was twisting and pulling.

"I never asked him to," she said. "I never knew how hot it was 'til I saw you doing it. After I watched you, I went downstairs in the bathroom, and I fingered myself to a huge orgasm."

He pumped his dick a little harder at that thought, then said, "Why don't you do it now? Take your shorts off and finger yourself while I jerk off for you."

He was definitely getting into the voyeur thing. He would never have guessed that having somebody watch him masturbate would be anything but humiliating, but it was unbelievably arousing.

Penny stood up, pushed her shorts to the floor, and then sat back down, facing him with her legs spread wide apart. She rubbed both hands over her pussy, pressing down on her clit, and squeezing her lips together. Then she spread her lips apart, and used a single finger to rub on her clit. She moaned and closed her eyes at the familiar electric feelings it sent all through her body.

"Oh, my God!" Ryan said, staring at her finger squishing over the soft folds of the pussy he only ever dreamt about. "That is so fucking hot!"

As Penny slid a finger between her wet pussy lips, burying it all the way into her cunt hole until her hand flattened against her "landing strip" of pubic hair, she said, "You've never watched Suzy do this?"

"Same thing," he said. "I never asked her to ... but I think I will!"

"You think she'd do it for you?" Penny asked as her hand picked up speed, finger-fucking her pussy hard, making wet slapping sounds.

"I don't know," Ryan said as he watched Penny's hand flying, and picked up his own pace to match her rhythm. "She can be kind of ... you know, adventurous when she's hot."

They both stopped talking, and concentrated on watching the other jerk off, like they'd each done countless times, but always alone.

In his most perverse fantasy, Ryan would never have imagined himself sitting a foot and a half from his beautiful, stark-naked step-sister, jerking off his rock-hard cock while he watched her slam her finger in and out of her wet cunt, and squeeze and pull on one of her nipples at the same time!

Then suddenly, Penny stopped fingering herself, and reached out and grabbed Ryan's wrist, stopping him for jerking.

"What? What's the matter?" he said.

"You're going to cum, if we keep this up," she said. "Me, too."

"Well, yeah! I thought that was the whole point!"

"It is," she said, "but not so fast. I want you to wait."

"Wait? How long?" he asked, thinking this was one of her teases. He wondered if she was suddenly going to turn Evil Mistress on him.

She didn't answer his question, but instead said, "Open up that video you were watching the other day."

"What?" he said. "Pen, I assure you I don't need to watch a video to keep it up for you. Watching you finger-fuck your own pussy is the hottest thing I have ever seen!"

"I like watching you jerking off your cock, too," she said, "but there's something in the video I want to see again. In fact, that's one of the other things I want; for you to make me a copy of that video—or send a link to it, or whatever."

"What's the third thing?" he asked, as he reached for a Kleenex to wipe the pre-cum and spit from his hand before touching his keyboard.

"I'll tell you when we're watching the video," she said.

As Ryan navigated to his porn stash, and typed in the password to the folder, what had been the hardest hard-on he had probably ever had began to soften a bit.

Noticing, Penny reached over, wrapped the fingers that had just been deep in her own pussy around his shaft, and started to slowly stroke it up and down.

"I'll keep this up, while you bring the movie up," she said.

He sucked in a long breath and moaned, "Oh, God!" as he looked down at her hand sliding up and down his cock. He looked at her face, and she grinned. "If this is just some kind of wet dream, I hope I never wake up!" he said.

She just chuckled, and ran her thumb over the slick head of his dick, to smear more pre-cum down its length as a lubricant. She had stroked Greg's cock, before, but just to get him hard ... and while she was sucking on it, of course. She had never though about jerking him off, but she found she liked doing it to her step-brother.

The video started, and she said, "Zoom to that scene you were watching the other day."

"I don't remember," he said.

Keeping her right hand stroking his cock, Penny reached over with her left, and picked up her phone. A bit awkwardly, she finally opened the clip of him jerking off, and showed him.

"Okay," he said, recognizing the scene on his computer. He tapped the fast-forward button, and agreed, "Yeah, that's where the two couples swap partners for the first time. That is a pretty hot scene."

He fast-forwarded through the build-up part of the scene, where the two guys and two girls decide to use the vacation-rental house's hot tub. When one of the girls discovered she had "accidentally" left her bathing suit at home, they all decided to skinny dip in the tub.

When Ryan got to the spot where they had soaked for a while, and were all sitting on the edge of the tub, naked and wet, Penny said, "There! Stop there."

On the screen, the two girls began to kiss, with hungry open mouths, and flicking tongues. As they played with each other's tits, the camera panned back to show the two guys next to each other, watching the show, and slowly stroking their hard cocks.

With a close-up of full red lips sucking on a large dark nipple, the scene did a fade-out, and came back with the girls on the king-size bed. The guys were watching from a wide love-seat chair at the foot of it.

The blonde lay on her back, with her legs apart as the brunette crawled between then, and lowered he mouth to the glistening lips of her pussy.

She passionately kissed all over the lips, and then pushed her tongue as deeply into the folds as she could. She paid special tongue-attention to her friend's clit, and then she began sucking on it.

The blonde was moaning in ecstasy, and squeezing one tit with one hand, while the other hand rubbed the back of the brunette's head, encouraging her to keep licking and sucking her cunt.

As the video played, Penny continued to stroke Ryan's cock while rubbing her own pussy with her other hand. And as much as he liked this video and the great girl-girl scene that was playing, he completely ignored the actresses on screen and watched only his step-sister's two hands; one sliding up and down his rigid cock, slippery with plenty of the pre-cum that oozed from the top, and her other, rubbing hard and fast across her cunt lips, wet with their own juices.

The girls on screen were now in a 69, and the camera zoomed in close to watch the blonde, on top, gyrate her hips and rub her soaking wet pussy into her friend's face. The brunette then reached up, spread the blonde's cheeks apart, and began rubbing her wet finger over the tiny pucker of her butt hole.

As the guys watched and the blonde moaned in pleasure, the brunette hungrily ate her friend's pussy while gently pushing her finger up her ass.

The tightening of Penny's grip on his dick and the increased speed that both of her hands were traveling told Ryan that his step-sister was really turned on by the hot girl-girl action, which surprised him a little; he thought only guys and lesbians thought that was hot.

As Penny watched the screen, Ryan reached over and gently pushed her hand aside from her pussy, and he began to rub his fingers over it, as fast and hard as she was jerking his cock.

"Oh, yeah!" was all that Penny said, and they both swiveled their chairs around to find a position that gave them each comfortable access to jerk the other off.

With his hand mashing against her sloppy cunt, she let out a low moan, and moved her now-free hand up to squeeze her tit and pull on her nipple, while continuing to jerk him off with the other.

Ryan rubbed and squeezed Penny's clit, and then flattened his hand over her whole pussy, rubbing hard into the wet folds. He then crooked two fingers, and slid them into her juicy cunt hole, and began to finger-fuck her, making erotically wet slaps against her completely soaked and burning pussy.

Penny moaned, "Oh, my fucking God!"

On screen, the girls had switched positions, with the brunette now on top, and the two guys had joined them on the bed.

As the blonde, now on her back, lapped at her friend's pussy, the tall guy, on his knees, moved in above her head. With the camera in close, the short guy took hold of his friend's cock, and guided it to the blonde's mouth. After she had lapped and sucked on the head for a bit, he guided it up to the brunette's cunt hole, and held it in place while his friend rocked forward, spreading the slick wet lips, and penetrating her in one long, slow push.

The brunette let out a very satisfied, "Oh, my God, yes! Fuck me! Fuck my cunt!" She then dove back into eating the blonde's pussy while jamming two fingers up her hungry cunt hole.

Meanwhile, the blonde was lapping at the juicy pussy and cock combination that fucked right above her face. After a dozen or so strokes into the brunette's cunt, the guy pulled out, and his friend directed his pussy-soaked cock to the blonde's mouth where she sucked off her friend's juices mixed her husband's male muskiness, and the saltiness of his pre-cum. The short guy then guided the cock back to his wife's waiting cunt hole.

As his friend drove into his wife's hot pussy, the short guy leaned down, and flicked his tongue over her little ass hole. He then pushed it as deep into the tiny opening as he could, and began driving it in and out.

The brunette moaned and moaned into the blonde's pussy as she lapped at it while getting fucked up the cunt, having her clit sucked, and getting tongue-fucked up the ass, all at the same time.

Both Penny and Ryan were getting close to their orgasms, and the closer they got, the more each picked up the pace of jerking the other off .

In the video, the short guy had moved around to his wife's face, and as he held her head, he fucked her mouth, every once in a while pushing his dick all the way down her throat. All the while she continued to noisily pound away at the blonde's wet cunt with her fingers and hand.

As Ryan jammed his fingers in and out of Penny's soaking wet cunt, she suddenly stopped stroking him, and just gripped his stiff cock tightly. Her whole body tensed and she let out a long, high pitched noise, almost like the air being let out of a balloon.

Immediately, Ryan's hand was drenched with her pussy juice as her body spasmed in one orgasm after another.

Still holding his rigid cock, she put her other hand on top of his cunt-fucking hand, and made him pound into her erupting cunt harder and faster, as the juices gushed from her swollen pussy lips.

Finally, she clamped his hand down tight against her soaked pussy, and just held it there while she closed her eyes, leaned her head way back, and sat there panting, trying to recover her breath.

A few moments later, she was recovered enough to open her eyes and look at Ryan. "Your turn," she said.

Never letting go of his cock, she stood and pushed her chair back out of the way. She then dropped to her knees beside him, and began stroking his slippery cock, again.

Less than a foot away from it, she watched his stiff wet cock intently, as she jerked him off.

He gripped the arms of his chair as she pounded her fist up and down his cock. As he felt the familiar signs of his pending orgasm building, he moaned, "Oh, yeah, Pen! That's it, that's it! Jerk off my fucking hard cock!"

Encouraged and turned on by his dirty talk, she jerked him even faster, and he responded by almost groaning, "Oh, fuck, yeah! I'm getting ready, Pen! I'm gonna cum!"

Penny felt his cock pulse in her hand as the first jet of his cum erupted from the top, shooting all the way up to his chin. She continued to jerk him off as squirt after squirt shot out, coating his chest and belly with ropes of his sperm.

He finally had to reach over and stop her hand as the post-orgasm sensitivity in his cock head grew to be too much.

He leaned back in his chair, panting, and moaning, "Oh, God, that was so fucking hot, Pen! I don't think my balls ever made that much cum in my life!"

She pulled her chair back, and sat back down beside him. "Have you ever tasted your cum?" she asked him as she ran her fingers through the thick white juices on his chest.

His first instinct was to lie, and say, of course not, but before he could answer, she said, "I've tasted mine; I like it."

"I ... I guess I have," he answered.

She chuckled, "You guess you have? You're not sure?" She gathered some of the thick juices onto her fingers, and lifted it up. "How about a reminder?"

She raised her soaked fingers to his mouth, and he opened up, taking them in, and sucking and licking them.

She pulled them out with a Pop!, and he said with a laugh, "Oh, yeah, I do like it ... especially off your fingers. Do that again."

As she fed him several more finger-fulls of his cum, which he hungrily sucked off, he reached over, and rubbed his fingers over her wet pussy, slipping two fingers inside, and wiggling them around. When he pulled them out, her mouth was already open, waiting for them.

She lapped and sucked on his fingers, and pressed her tongue between them, spreading them apart to lick inside.

After he fed her a third taste of her own pussy juice, and was inserting his fingers for more, she said, "That reminds about the third thing."

As he gently massaged her pussy, she reached over to the keyboard, and fast-reversed to the scene they had watched. She stopped and froze the frame when she got to the spot where the two girls were in a 69 on the bed, with the brunette's mouth sucking on her friend's wet cunt.

"I want you to talk Suzy into doing that with me," she said.

He laughed at first, but then realized she was serious. "What? Are you kidding me? I can't ask her to do that!" he said.

"You don't think it's hot?" she asked.

"Of course I do," he answered, "but she's not a lesbian or something."

"Neither am I, but I think it would be amazing!" she said. "It's called being bi-curious."

"Yeah, but I don't think she is," he said.

"Have you two ever watched this movie together?" Penny asked.

"Yeah," he said. "So?"

"And how was the sex afterwards?"

"Pretty hot!" he answered. "Like I said, she can get kind of wild when her juices are flowing, so to speak."

"Well, there you go," Penny replied pointing to the girls on the screen. "If she found this disgusting, her juices wouldn't have been flowing, and she'd probably have walked out and left you to do what I filmed you doing the other day."

He wasn't sure if that was a thinly veiled reminder of her threat about sharing the video, or if she was just making a point.

"And what if I ask her, and she thinks that we're both too perverted to be around? I could pretty much kiss my sex life good-bye for a long time ... except for keeping myself company," he said, stroking his now softened dick up and down a couple of times to illustrate.

"If you ask her, and she says no," Penny said, "I'll give you a blow job every day for a week."