Penny & Ryan Pt. 04

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Penny, Ryan and Suzy all try anal.
7.4k words
4.7
35.9k
49

Part 4 of the 5 part series

Updated 06/08/2023
Created 03/14/2018
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CaseyBea
CaseyBea
1,354 Followers

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

*****

Ryan, Penny, and Suzy had plenty of room in the big walk-in shower of the master bedroom to soap each others bodies and slide their hands over every square inch of one another's glistening skin.

At one point, when Penny was sliding one hand up and down Suzy's butt crack, and massaging a slippery tit with the other, she wiggled a finger tip around her tiny ass hole, and said, "Have you guys ever done anal?"

"We tried, once," Suzy said, "but it hurt too much." She through for a second, and added, "But I really liked it when you fingered my butt while I was cumming."

"You mean like this?" Penny said, as she gently pushed her soapy middle finger up Suzy's ass.

"Mmm!" Suzy replied, as she wiggled her butt, and pushed back against the finger.

With wet slapping sounds, Penny began to finger-fuck her little ass hole, and Suzy leaned over, put her hands against the wall, and spread her legs.

Ryan took over the job of massaging and squeezing her tits, and Penny knelt down to where she could watch her finger slipping in and out of the tiny pink pucker.

After a little while, Penny added a second finger, which Suzy made no complaint about.

When she added a third, she had to push a good deal harder, and she asked, "Are you still okay?"

"Yeah," Suzy said. "I feel stretched, and it hurts a little, but it feels good at the same time, you know? Don't stop, but no more fingers, okay?"

As Penny finger-fucked her ass, Suzy reached down, and began to finger her own pussy. She quickly had two fingers ramming into her cunt as Penny's three stretched her ass hole. The combination didn't take long to push her over the orgasm edge.

When she caught her breath, she said to Ryan, "Maybe we need to give that another try." She turned and kissed Penny, and added, "With a good coach."

"You up for it, little brother?" Penny asked.

"Heck, yeah!" he said, sliding his hand up and down his hard soapy cock.

"I mean getting, not giving," Penny said.

"What?" he said.

"Turn around and put your hands on the wall," Penny told him.

"I don't know about this!" he protested.

"You just watched Suzy take three fingers, and enjoy it," Penny said. "You think her butt hole is bigger than yours?" She pushed him on the shoulder, and commanded, "Assume the position!"

Suzy laughed, and said, "Just trust the coach; she knows what she's doing."

"Okay," Ryan said as he turned, reached out for the wall, and spread his feet. "But only one finger!"

Penny soaped up both of her hands, and as she slid one of them up and down his butt crack, she wrapped the other around his stiff cock, and began stroking it.

Keeping her wrist tight into his now-slippery crack, she reached between his legs, and began to massage his balls. As she jerked him off, she mashed her cock-hand down into her handful of wet, soapy balls with each down-stoke.

She then slid her hand back up his ass, and while still stroking his cock, she began to wiggle the tip of her middle finger against his tight sphincter.

Well past the point of saying stop, he relaxed as much as he could, and found that he actually enjoyed the stimulation.

Slowly, and with lots of soap for lube, she pushed her fingertip into his ass, up to the first knuckle. She then took it in and out several times.

He found that he actually liked the feeling of the penetration. He wiggled his butt, and said, "Go ahead and push it in deeper. That actually feels kind of good."

By this time, Suzy had gotten down in a crouch so she could see Penny's finger slipping into her boyfriend's ass.

Slowly, Penny pushed her finger deeper and deeper up Ryan's ass hole, past the second knuckle, and them as deep as it would go, with her hand pushed tight into the cheeks of his ass.

She then drew it all the way out, and slid it all the way back in, all the while jerking off his rigid cock.

"Go ahead and fuck me with it!" Ryan told his sister.

Penny happily complied, and began shoving her finger faster and harder up his ass, and coordinated her strokes on his cock with her fucking. Each time she drove the finger deep in to his anus, her hand slid all the way down his cock to his balls.

"Oh, Wow!" was all he could say at the coordinated attack, as he leaned heavily against the wall with his head hanging down between his arms.

"Tell me when you're getting ready to cum," Penny said as she fucked his ass and jerked him off. She had one more trick—that she'd only read about in a porn story—that she wanted to try.

While Penny continued bringing him to the edge, Suzy worked her way around his spread legs until she was crouching in front of him.

With his soap-covered cock inches from her face, she said to Penny, "Jerk him off in my face! I've always wanted to see what that feels like!"

Ryan looked down at her face, right in front of his cock, and at his sister's hand sliding up and down its length, and said with a chuckle, "All you ever had to do was ask; I'd have been happy to oblige."

"I was afraid you'd think it was too weird," she said, smiling up at him.

He laughed, and said, "With my step-sister finger-fucking my ass and jerking me off, I don't think anything could be too weird, anymore!"

At the same time that Penny could feel Ryan's body start to tense up, he said, "Okay, I'm getting ready. Just keep it up, just like that."

He looked down at Suzy, and said, "You want it in your mouth?"

"No," she said. "All over my face! I want to feel your hot cum on my nose, my cheeks, even in my eyes! Squirt your fucking cock right in my face!"

The dirty-talk spurred both Penny and Ryan, and in a few seconds, Penny's finger pounding up his ass, and her hand flying up and down his cock had Ryan saying, "Oh yeah! Here it comes! Here we go!"

At that, Penny jammed her finger deeply into Ryan's ass, held it there, and began to rub her finger tip around on his prostate.

"Oh, Jesus!" Ryan blurted at the new and intense sensation that was like an electric shock right up his cock.

"You okay?" Penny said, not really sure if she was doing it right.

"Shit, yeah!" he said. "Keep doing that!"

He looked down at Suzy, just inches in front of his cock head, and said through gritted teeth, "That pretty face is going to look so fucking hot covered with my cum!"

"Oh, yeah! Do it! Cum all over me!" she said, with her eyes squinted against a possible direct hit in them.

"Ahhhhh!" he let out as the first squirt blasted out of his cock.

He had a hard time keeping his eyes open through the intensity of the orgasm, but he didn't want to miss seeing his girlfriend get her very first facial.

The first powerful spurt hit Suzy square in the nose, and actually went a little up one nostril. She kept her eyes squinted and her mouth closed, and as squirt after squirt kept gushing out, she moved her face around to catch it on her cheeks, her lips and chin, and even her forehead.

The intensity of the orgasm—with his sister's finger grinding into his prostate—was unlike any he'd ever had, with the possible exception of his very first time—which, oddly, was also in the shower ... only he was alone, then.

Considering that he had had two other orgasms in the recent past, Ryan was surprised at how much cum he was watching spurt onto his girlfriend's face.

Finally drained to the point of feeling his balls ache, he moved to the side, disengaging himself from his sister's finger and her hand. He leaned heavily against the wall, and let out a long, "Wow!"

Penny rinsed her hands under the still-running shower, and helped Suzy get to her feet. She looked at her cum-dripping face, and said, "That was fucking hot, seeing you get facialed. Did you like it?"

"Oh, yeah!" she said. "It just felt so ... nasty! Like I'm a little cum-slut!"

"Which you are!" Penny said with a laugh.

"Hey! That's my girlfriend you're talking about there!" Ryan said in mock indignation. Then he chuckled, and added, "And I love her that way!"

Penny then took hold of Ryan, and pulled him near. She put his hand behind his head, and as she moved her own face in close to Suzy's, she guided his, as well.

"You helped make this mess," she said to him, "you can help clean it up."

He needed no further encouragement, and he and Penny began kissing, licking, and lapping Suzy's cum-cover face, sharing their finds with her open and waiting mouth.

After they'd dried each other off, they headed to the kitchen for some snacks and drinks. It was almost 9:30.

As they stood around the island, eating chips and drinking sodas—all still completely naked—Suzy said, "You know, Pen, you seem to be the expert on anal; do you and Greg do that a lot?"

"No," she said, obviously disappointed. "I've tried to get him to do it, but he thinks that anything about the butt hole is just gross. He won't even let me put my finger in him."

Ryan looked a bit surprised, and said, "So, that was your first time when you fingered my butt, just now? You sure made it seem well-practiced!"

"I've thought about it a lot!" she laughed. "That bit at the end—with your prostate—I read about in a bisexual porn story."

"Oh, yeah! That was unreal!" he said. "It makes me get why some guys might want to go bi."

Getting back to her original question, Suzy said to Penny, "So, you've never actually taken a dick up your butt, either? ... although it does sound like you'd like to try?"

"I've used my fingers," she said, "but that's not easy on yourself. And I've used my gildo, too. But, again, that's not the same, I'm sure."

Suzy smiled, and said, "There's one way to find out!"

The two girls laughed, and looked at Ryan.

He finished his swallow of soda, and then shook his head slowly back and forth, and said in mock resignation, "Okay ... if I have to. The things we do for love ..."

"Or lust!" Penny said.

Suzy laughed, and said, "Yeah, I'm sure we're going to have to really twist your arm to get you to fuck your gorgeous sister up her beautiful round ass."

Penny chuckled, and said, "You seem almost as interested in it as me. You going to try it, too?"

She grinned, and said tentatively, "Maybe. But I want to watch you, first."

"To see if it hurts too much or if I like it?"

"That," Suzy answered, "Plus, I want to watch his hard dick spread your tiny little butt hole wide open. I think that's going to be hot!"

"You going to play with my pussy while he fucks my ass?" Penny asked her.

"Oh, yeah!" Suzy said with a chuckle. "My own, too! But, sorry, I'm not going to eat you out ... I wouldn't be able to see the show, with my face under you and my tongue stuck in your cunt."

"I can't believe I'm saying this," Ryan said as he set his empty bottle on the counter. "But can we wait a while to get started? Three orgasms—really great orgasms—in that many hours, has me a little ... spent. I've never even jerked off that much, before.

"How about if we go downstairs, and watch some of the video we just shot for a little while."

The girls laughed, and Penny said, "Poor boy! I'll bet this is a problem you never thought you'd have to put up with."

"Not in my wildest fucking fantasies!" he replied with a laugh.

Cuddling their naked bodies against each other, the girls made themselves comfortable on the pull-out bed, while Ryan set up his laptop to show its video on the big TV.

Ryan fast-forwarded up to the point where he had slid Suzy's pants off, had her shirt open, and had her lying in wait for Penny's surprise entrance.

As Penny walked across the screen, close to the camera, Ryan said, "That is a nice ass, Sis!"

They then watched her kneel down, spread Suzy's legs, and put her face in between them.

"God! That was so awesome, Pen!" Suzy said. "It was a surprise, but it was like the most natural, wonderful feeling at the same time." She slid her hand gently into Penny's crotch, and added, "I love the way you eat my pussy. It's everything I ever imagined it would be, and much much more!"

"Ryan eats you out, doesn't he?" Penny said.

"Yeah, but not like you do," she answered.

"Maybe I should take some lessons," Ryan said.

"No," Suzy replied. "I like the way you do it, too, and I want to savor the differences!"

It occurred to Penny that in all that they'd done, Ryan had never gone down on her. He had teased at it, when he orally signed their agreement that had started this whole thing, but that didn't count, it was so quick.

"If I can talk you into it," Penny said to Ryan, "I'll have to have you show me your talents in that regard."

"I don't know," he said. "That might take a lot of sweet talking ... like, Hey, Bro; eat my pussy!"

They laughed, and then Suzy, asked, "Does Greg eat you?"

Penny sighed, and answered, "Not so much eats me, as laps at me to get me wet. Which, until you had your beautiful little face stuck I my hot, dripping pussy, I actually thought was pretty good. Now, I know better. It's going to be hard to be satisfied with that, again."

By the time they watched the part where the two girls sucked and jerked Ryan off all over their faces, they agreed that the static images from the stationary camera left something to be desired from a porn standpoint. And, although the two girls were ready to start again, Ryan wanted to see how his hand-held phone-video compared to the security-camera-style images.

While Ryan got his phone linked to the TV, the girls were massaging each other's pussies, squeezing one another's tits, and kissing passionately.

When the scene that Ryan had shot of Suzy's very first time licking a pussy came up on the TV, both girls stopped to watch.

All three watched the close ups of Suzy's tongue, lips, and face in Penny's glistening pussy, and then a pan shot up across Penny's tits, and finally to the look of pure pleasure on her face as she lay her head back, and lost herself in the feeling between her legs.

The video then panned out to show Suzy's naked white ass wiggling, and then zoomed in to show the wet folds of her pussy lips, and the as-yet-untouched little bud of her ass hole.

"You could have a future on both sides of the porn camera," Penny said. "That's pretty good stuff with just a phone."

"I wonder where you send in your résumé!" Ryan said with a laugh.

With the sounds of Suzy's licking and of Penny's contented mews coming over the speakers, Penny said, "You could probably sell this as an audio-visual training video on eating pussy! I'd buy a copy for Greg!"

"Was that just beginner's luck?" Ryan asked Suzy.

"It might be the first time I'd done it," she answered as she rubbed a finger gently through Penny's pussy lips, "but it wasn't the first time I'd though about it." She turned and kissed Penny on the lips, then added, "The beginner's luck was that my first time was with you!"

When they got to the selfie shot of Ryan tongue-fucking his sister's butt hole, Penny said, "Okay, I need some real fucking!" She took hold of Ryan's well-rested and ready-for-action erection, and added, "And by that I mean your hard cock up my tight little ass!"

Ryan hit the pause button on his phone, and set it down, not needing to be asked twice. The scene that froze on the screen was of the pink handprints that Ryan had slapped onto Penny's naked ass.

Penny rolled away from Suzy, and stretched over to open an end-table drawer. She reached in and took out a bottle of K-Y lube.

Ryan chuckled, and said, "Well, don't you come all prepared?"

"Like a regular fucking Girl Scout!" she replied.

Ryan laughed, and said, "Those are the best kind!"

"I want to try it, au naturel, though," Penny said. "This will be just-in-case."

"Okay," Penny then said as she got on all fours on the bed, with her ass toward the other two. "Ryan, you tongue-fuck my butt hole, like you did before, but with lots of spit; get it nice and wet as deep down as you can.

"Suzy, while he's doing that, you suck on his cock. Same thing; get it really wet with lots of spit. If you can get some pre-cum oozing out, that would be great, too."

"Put a little thought into this, have you?" Ryan said with a chuckle as he leaned over and spread his sister's gorgeous ass cheeks with his hands. He lapped around the puckered little hole, and then he pushed his tongue as deep in as he could.

Penny let out a soft, "Mmm," at the sensation, and then an "Oh, yeah," as he started to bob his head up and down, tongue-fucking her backdoor.

Suzy wiggled herself between Ryan's legs, and began sucking, lapping, and stroking his cock.

Ryan quickly had a humping rhythm going where he was fucking his girlfriend's mouth with his cock, while doing the same to his sister's ass hole, with his tongue.

After a short while, Penny said, "Okay, one last spit, and then let's see if you can shove that thing into me."

Suzy gave his cock a slobbery lap, and crawled up onto the bed next to Penny's ass.

Ryan left one last pool of saliva on Penny's sphincter, and got on his knees behind her.

Suzy took hold of his cock, and as he leaned forward, she placed the head up against Penny's little rosebud.

Just before he began his first push, Penny said, "Is anyone filming this? You guys have a bird's eye view, but I'd like to see my ass hole get stretched open, too."

"Shoot!" Ryan said and reached for his phone. In a few seconds, they were ready to go, again.

With Suzy making sure the head of his cock stayed on target, Ryan leaned into his sister, mashing the fleshy head of his dick up against her. With more force than he thought he'd need to spread the little hole, he wondered if it wasn't hurting her.

"You okay, Pen?" he asked, still leaning into her.

"Yeah," she answered with a little groan, with her face in the pillow. "Just keep pushing like that; I'm trying to relax my butt muscles. When the head goes in, though, stop so I can get used to it."

With Suzy's hands spreading her cheeks apart—and her face just inches from ground-zero—Suzy let out an "Oh, yeah!" when Penny's tight little ass hole finally enlarged, and Ryan's cock head disappeared from view, inside of her.

"Oh, man!" Ryan said at the tight grip that now held his cock.

"You okay?" Suzy asked as she gently massaged Penny's cheeks, and stared, fascinated, at her boyfriend's hard cock impaled in the expanded little hole.

"Yeah," Penny said from the pillow. "I like the stretched feeling, like you said about my fingers."

"You ready for more?" Ryan asked.

"Actually, let's just do that a few times," she answered. "I kind of like the feeling when it popped inside of me. Fuck just your head in and out."

With Suzy holding his cock, he eased his head out, and then with his girlfriend keeping him on target, he rocked forward, again. It went in much easier the second time, and then easier, yet, the third time, as Penny was able to relax more, and her little hole got used to the size.

As he gradually picked up the speed of his shallow fucking, Penny said, contentedly, "Oh, yeah! I was right; I do like my ass getting fucked!"

"Let us know when you want more," Suzy said, now stroking Ryan's cock, as well as guiding it.

"Spit it up, again, and let's do it," Penny replied.

With the head still inside Penny's tight ass hole, Suzy spit on Ryan's cock, and spread it around. Then, she had him back out, and she put her face into Penny's ass crack, and tongued the little hole, leaving a good pool of spit behind.

CaseyBea
CaseyBea
1,354 Followers