My Sister's Best Friend - Cover

My Sister's Best Friend

Copyright© 2020 by RickSands

Chapter 5

Erotica Sex Story: Chapter 5 - A story of Gary's illicit attempt to spy on his sister and her most beautiful best friend. Much sex and eye opening surprises for Gary, but with him eventually finding love and happiness

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Teenagers   Coercion   Consensual   Reluctant   Heterosexual   Fiction   Sharing   Brother   Sister   Group Sex   Anal Sex   Cream Pie   Oral Sex  

Gary gave Cyn a call the next morning, and he had never been more nervous in his life. He realized he knew too much about her, knew more than any man should ever know about a woman even after a decade of marriage. And here he was calling and asking her for a date. What most tied his stomach into knots was desperately wanting her to say yes, to show some interest in him. He most feared her politely saying no, and for him becoming a rejected loser, having to see her over and over again every time she visited Penny.

He could simply blackmail her, show her the video and tell her that he was going to release it to everybody at the high school if she didn’t become his sex slave, but he knew he couldn’t do something that evil. He still had Penny, had a sister with an unquenchable cunt, and he could always soothe his hurt heart inside her wet pussy. And deep down, if Penny decided he wasn’t worth her time, he probably still wouldn’t do anything with the video. After all, he was a nice guy.

So he dialed, and got voicemail. He realizes he should have texted but left a short message anyway, just a call me kind of thing, and only a minute later she called him back.

“So, Gary. This is a surprise. What’s going on?”

“Um, nothing,” said Gary, trying hard not to stumble over the many words filling his head. “Wondering if you’d like to go out this weekend. You know, go do something.”

Silence filled the void between them, and then Cyn’s voice took on a sharp questioning tone when she threw a question back at him. “Did Penny set you up to this? What’s going on?”

“Nothing,” threw back Gary. “I’m just asking you out. Why the questions? And why about Penny? Yeah, I asked her what you might say and she just told me to ask you myself, so I am.”

This went on for a few minutes, Cyn finally backing down and to Gary’s joy actually saying yes, that she’d be willing to go out. “So, where to? What do you have in mind?”

This is what had stumped Gary. Where could he take a girl like Cyn? He didn’t have much money and neither were of drinking age, and he thought movies a waste of time, where you just sat and ignored the person next to you for two hours. “Do you think it’s too corny to just go bowling and grab something to eat afterwards?”

“No, sounds good. I haven’t bowled in like a dozen years,” she responded, “but that could be fun. When?”

Gary had to cut back on the celebration and sound cool and at ease, saying “How about Saturday, about 5.”

“No, can’t do that. I’m doing something then. I’m free tomorrow. How about that?” “OK. I’ve got tomorrow and Saturday off, so tomorrow about what, maybe around 5? I’ll pick you up.”

And it was that simple. Gary could hardly believe that he was going on a date with a girl like Cyn. It wasn’t just that she was hot looking or was fun and knowing that just being around Cyn would bring life to any experience. It was also his hidden and secret knowledge about her, knowing what she did, could do sexually. Gary’s imagination went overboard for the next few hours, sometimes coming to the surface to ask Penny for dating tips with younger girls like her, then diving deep to dark areas of his mind that only increased his feelings of sexual need and frustration.

That afternoon their parents unexpectedly announced that they’d be having dinner with some friends and that Penny and Gary could help themselves to anything in the freezer. That gave Gary even more time to quiz Penny about everything having to do with Cyn, like food preferences and music downloads and, of course, sex.

“So, why is she so good at sucking guys off?” he questioned, a large slice of microwaved pizza garbling his words.

“Not for me to say,” said Penny, wisely focusing on her salad. “I can tell you two things. First, it goes way back, and if she decides to talk about it, then she must really trust you. And second, it has to do with keeping guys away from anything below the waist, if you know what I mean. You know guys. They just need a place to shoot their wad, and some guys really get off on making a girl suck them off. After that they calm down and either dump a girl off at home, which shows what losers they are, or they open up and look for something other than sex from a girl. It’s a good test of a guy. Oh, and as for Cyn, she’s really nervous about a guy seeing her naked. Not so much her tits as her twat. She’s really self-conscious about it.”

“You mean her big lips, right?” said Gary. “You said something about that.”

“Yeah,” continued Penny, “but more than that. You’ll have to get that from her too. Kind of a surprise, but a good one. Who knows, maybe you’ll find out tomorrow, but I doubt it. She usually likes to take it slow.”

The two talked a little more and cleaned up. Gary was coming out of the kitchen when he looked over at Penny, wearing a long thin pullover sweater to ward off the cold of the AC yet also a short pair of shorts, her legs bare from her lower ass cheeks down to the floor. Her back was to him, playing with the TV and remote, her ass dancing to some music her ear buds were plugged into. Without a thought, he walked up behind her, his hands going around to her front and then up and under her sweater and halter top, easily pulling Penny into his embrace as his fingers and palms covered and began playing with her breasts.

“Hey,” said Penny. “I thought we were over this. No more Gary. Save yourself for Cyn. She’s more than you can handle, I promise.” But Penny didn’t duck low and squirm away, her ass actually sticking back and pressing into Gary’s crotch.

Gary said something like “But you smell delicious, and you look so hot, your ass looks so ready,” but he wasn’t thinking about words. With the feel of Penny’s ass dancing against his long hard boner, Gary tripped Penny over a leg, twisting her down and around, her face and chest down onto the living room rug with him on top of her, hands still holding Penny around her tits. She struggled and tried to get up, but as he sat on her ass, it only took seconds to pull his hands free from her chest, then pulling her arms back, stretching out the arms of her sweater and tying them together at her back. It was an easy and elegant way of forcing Penny to submit, forcing her to allow Gary to do with her as he willed. Then Gary reached under the front of her shorts undid the snap, and pulled Penny’s minimal covering down her legs, exposing her welcoming butt crack and the wonders between her legs that now lay open to him.

“No Gary. Not this time. I promise you anything, I’ll do you all next week, but not now.” As he dropped his pants, Gary wondered why she was so reluctant, so different from just a couple of days before. He found out as he pulled Penny’s ass back, pulling her tight butt crack onto his engorged cock, ready to slide his leaking boner into Penny’s equally wet cunt and fuck her into the ground for the next hour. This is when Penny went crazy, finally bucking up and down, back and forth, her arms still tied behind her as she squirmed a dozen different ways to escape from the onslaught of Gary’s penis.

“Damn it Penny, what’s up? What’s so special about now? What’s wrong?”

“Just untie me, Gary. Please. Don’t fuck me now, not yet. I promise I’ll do anything if you just let me go for a minute.”

Penny seemed adamant, wild and concerned, and Gary sat back on her legs, pulling his cock away from her gateway to heaven. “OK, OK. I’m sorry. Stop bucking like a horse and I’ll untie your sweater.”

Gary did as he said, freeing Penny’s arms and allowing her to roll over and sit up, but as she did so he pulled her in, sitting on top of her naked thighs, his leaking cock pressing into her stomach, then asking, “Fine. What’s going on?”

“You asshole. You have no right Gary,” said Penny, pushing herself back and away from him. “Just stop, OK? Let me sit up and I’ll show you.” She pulled the sweater off first, leaving just a turquoise blouse to cover Penny’s breasts, her nipples hard points showing through the thin fabric. Penny then rose up on her knees and reached down between her legs with one hand. Penny reached back, fingers up inside of herself, a look of deep concentration on her face.

For a quick second Gary thought she was playing with herself, but then she gave a deep sigh, one of contentment, then pulling her hand back to show a large colorful ball in her hand. It was larger than a golf ball, smaller than a tennis ball, and shiny with Penny’s own special brand of lubricant coating it. As she put it on the rug, Penny said, “I didn’t want you fucking me while I still had these inside me. Wait a second.” She then stuck her hand back between her legs and a moment later pulled out a second one.

“So, why do you have these in you?” asked Gary. He almost asked if they were a kind of birth control, but in an instant he knew. “It’s for fun, like a dildo, right?”

“Yeah,” said Penny, holding the two noisy and jangly balls in her hands, then saying “but it’s good for muscle control too. I didn’t want to show you because it’s really none of your business. I don’t watch you jack off, so you leave me and my balls alone. But now that you’re here, let’s try something. But you’ve got to go slow, like really careful, OK?”

“Yeah,” agreed Gary, not sure to just what he was agreeing. “So, what?”

“Here. Just let me put them back in, just where they always belong.” As though performing a magic trick, Penny slipped first one and then the other ball up into her vagina, then waving her ass and allowing Gary to hear their sexual magic in motion. “OK, now slip inside me, but real slow, and not too deep,” explained Penny. “I want to see what it’s like to be fucked by a live cock with both of my ben-wa balls inside me. This should be good.”

Penny laid back, tossing her top over to join her sweater, naked before Gary, her legs open and up in the air, welcoming him in to share in her sexual treat. Gary crawled up between her legs, a hand down to cup Penny’s ass, another hand on the rug to support his weight as his cock felt it’s way past her thighs, into her slit, and then easily slipping into her very wet pussy.

“Slow Gary. I can feel you pushing on them.” “Yeah,” replied Gary. I feel them. I can’t go very far in,” said Gary. “That’s OK,” murmured Penny, her arms pulling Gary’s chest into hers. “You feel good, just keep going in and out, like you just did.”

Gary pulled back, the hood of his cock pulling out, suctioning out an ounce of Penny’s overflowing secretions before pushing back in, a few inches up inside her and pushing on her beloved balls. Gary finally pushed both hands down to cup her ass cheeks, resting his weight on his arms, pushing Penny down into the rug as he began a rhythmic fuck of her vaginal gate.

It was wonderful for Gary, the muscles that held her hole closed giving the head of his cock a better sucking than any mouth any girl had ever provided. In and out, a hundred times, and though it all Gary could feel the balls rolling around inside his sister. Penny held him tight, then wrapped her legs around his torso, fucking him back, actually forcing Gary to push even deeper into her twat, his cock and her balls laying havoc to her pussy.

It went on like this for a while, first fucking Gary hard, then her legs kicking out as Penny spasmed as she let out a high pitched shriek, his sister lost in a sexual extravaganza Gary was only partially aware of. Just as Gary was coming to realize his own limits, a rising climax sure to take him over whether Penny wanted it or not, she began bucking hard, pulling back and releasing Gary’s cock from the tight hold of her cunt, then pushing her hips up and enveloping a good half of his length. Back and forth, Penny letting forth a rising wail, a long high note that broke in a scream like an ocean wave on the cliffs, her feet rising up and pounding down on Gary’s back as she pulled him into a tight embrace.

Gary was himself close to the edge, and as Penny slowed the wild gyrations with her hips, shuddering to a stop and moaning out “Oh fuck I needed that,” he took back control and began a final few dozen thrusts into her. Penny was wet, his pulling back out of her hole filling the living room with a wet sucking sound, as though her pussy didn’t want to release him. But he returned, pushing back into her hole over and over again, until finally Gary reached his own climax.

Pushing in as deep as he dared, his pole pushed aside her balls as his cock erupted, his own pair of balls pulsing hard and long in an attempt to flood Penny with all the seed and cum of a dozen young men. Penny’s legs rose again, pulling Gary’s torso in tight, causing his cock to go deep, his balls to press hard against her ass as he groaned out his delight. They lay like that for a minute, each moaning in pleasure, alone at the height of ecstasy, then coming down and sharing smiles and kisses, moving their naked bodies together as their sweat and cum was shared between them.

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