My Sister's Best Friend - Cover

My Sister's Best Friend

Copyright© 2020 by RickSands

Chapter 7

Erotica Sex Story: Chapter 7 - 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’s sleep was only temporarily broken by Cyn’s arrival, crawling up under the covers and merging with his body but otherwise allowing him to drift back into darkness.

The morning came too quickly, but Cyn made sure Gary gave blessings for its arrival. This time he was able to go slow, pulling one of her thighs over his hip and impaling her on his raging cock, torn between the incredible feel of pushing in and out of Cyn’s tight little hole and kissing and loving the beautiful face of a girl he thought could never be his. Even as he worked at holding back and trying to ensure Cyn’s everlasting happiness, Gary finally had to fall before his rising climax, gripping and stretching out her thighs and rolling her over for a last full minute of intense fucking before he emptied himself into her.

As his shuddering body began to relax and his balls pulsed out the last of their offerings, Gary somehow moaned out his true feelings, even his own ears surprised as he whispered “Oh my god Cyn, I love you so much.” He actually said more than that, mostly about how good it was to cum inside of her, but it was the love comment that gave them both pause.

Gary wasn’t sure how she’d take it, waiting a couple of minutes until his cock calmed and softened and he rolled off her back and to the side of his slim mattress, pulling her in for another kiss, wondering if he’d even really said it. He had, Cyn leaning in to whisper “So you love me, huh? Well, we’ll see. Let’s see how you really feel in a couple of months. Might just be that hot little hole you just told me you love cuming inside of. Yeah, I heard that too. But I have to admit the feel of your cock dancing around inside of me as you fill me up is definitely something worth loving. I’ve wondered what it would be like to be with you, and you definitely didn’t disappoint.”

“Um, nice of you to say that,” said Gary, still a little worried about how Cyn might have fared from that last minute of hard pounding and release, “but if you give me a few more minutes of rest, I’m pretty sure I can do even better next time.” He smiled, hoping Cyn would go down on him again and suck him into another hard-on. Cyn smiled back, saying “Hey, don’t worry about it. I’m happy. I don’t have to wet the bed every time. Besides, your parents are up, and after all the noise we just made we have a lot of explaining to do. Kind of embarrassing, but I guess there’s no way around it.”

Before Gary could say anything more, Cyn pulled away, rolling off the bed and into her dress and out the door in under a minute. If nothing else he had to pee and he quickly followed, arriving at the bathroom door just as Cyn exited. Two minutes later he was very sad to see Cyn and Penny walking out of the front door, each holding a can of cola to act as their breakfast, getting a quick kiss from both and extracting a promise from Cyn to call him that afternoon.

He was still nibbling on some toast and mulling over the joy that had been his just a half hour before when his mother walked up to the table and cleared her throat. Uh-oh. “So, it seems that you and Penny’s friend have been, well, having sex. Are you sure you’re ready for this, Gary? Seriously. She’s not even out of high school. Not only does this set a really bad example for Penny, but what if the girl gets pregnant? And I know this isn’t the first time. Your father and I have come home time after time and known you were having sex with someone. I mean, we could smell it. Really, it just fills the house. Dad was going to wait to say something, but seeing that girl Cyn here and listening to you two go at it, well, I don’t know what to say.”

Except that she had plenty more to say. It took a lot of patience on Gary’s part to get through the next half hour of lecture and parental nagging, but in the end his mother left him alone to live his own life, even if it was under her roof. He had to smile about his parents thinking that all of Penny’s expended pheromones and fully scented secretions filling the house were all due to Cyn coming over and having sex with him. If they only knew.

When Penny arrived back home she had to go through a similar grilling from their mother, though this time Penny having to answer questions about what kind of sexual predator she had brought home to enmesh poor Gary in an ill-conceived relationship. Parents really could be clueless. They were finally given a little privacy when their mother took off to do the grocery shopping and their father had turned in for an afternoon nap. That’s when Penny pulled Gary onto the couch and demanded some information. She already knew, of course, she and Cyn talking it all out just that morning, but she wanted his side of the story.

She laughed at his view of the Mario Kart game and then grimaced as he described what he saw when he and Cyn had walked in on Penny being piled on by Jason and his friends. Penny took time off from questioning him to giving some info of her own, letting Gary know that she really was serious about Keith. “You’ll like him once you get to know him. Yeah, kind of rough, but all with a big dose of caring. You’ll see.”

Gary was actually happy to hear this, but had to ask about what had gone down after they had left the party. “I get it, a wonderful man. I’m really happy for you, but what did he say when he walked in on you getting drilled by Jason and friends? I don’t see how he could just let that go.”

Penny again blanched and nodded, saying “Yeah, but he’s the one who actually thought I’d be safer naked and alone in the bedroom than down on the party floor. And the idiot had told Jason to keep an eye on me while he went out for beer. When he thought about it later he admitted to being dumb, and after I showed him how much I loved him he apologized and promised to never again let me out of his sight. I’m even going to meet him tomorrow for lunch, so it’s all good.”

Gary wasn’t so sure. He still didn’t really trust Keith, couldn’t imagine any man alive who would leave a girl like Penny naked and alone in a party full of lust-fueled men, and was sure there was more to the Jason and Keith and Penny thing than he could fathom at that moment.

Penny just wanted to move on and asked for details about what had happened in the park. Gary did his best to minimize the sex, focusing more on how happy he was that Cyn seemed to want him as much as he wanted her. “Just to let you know,” Penny said with eyes narrowed, her voice low, “she’s really into you. Not just for the hunk you are, good looking lady’s man and all, but because you also seem into her, all honest and sincere and shit, not just for the sex. She has a real feeling for you, so don’t blow it.” Gary smiled, happy to hear from Penny just what he wanted, that Cyn really would be sticking around. All he had to do is be wonderful and perfect all the time. Easy.

Then Gary did a stupid thing. He was honest, somehow dropping at the end of a sentence that Cyn had talked about the attack in the park just a year before. He was trying to be supportive, putting out a hand and asking Penny why she had never told him and if she was really over it. Penny grew quiet, said that she was surprised that Cyn had brought it up, but also that she thought Cyn had gone through much worse than she had.

“What do you mean?” asked Gary

Penny took a deep breath and said in a very low voice, “I don’t know if she gave you the whole story Gary. There’s stuff you just can’t trust telling a guy, so I’m not going to say much more. I don’t want to talk about it with you, and I can’t tell you everything, but I can say that most of what she told you is right on. The strange guys and their knives and our asshole boyfriends. Yeah, what do you expect. But what Cyn didn’t tell you is that while she was being face fucked by the one guy, he was having fun with his knife cutting off parts of her clothing. I mean like slipping it under her blouse and bra and cutting it up in strips until she was naked.

“His partner had already made a couple of slices in her pants, making it easier to get to her ass. Even after he had started in on Cyn he kept playing around with his knife and by the time it was all over she had nothing to wear. It sounds like it was nothing, just some clothing, but it was pretty traumatic for her. And don’t forget, she was only a couple of months away from being a virgin. This was all totally new and she wasn’t ready for it. And for me, like she said, our boyfriends had just finished unloading into me and I figured it would be better if the guy slicing off her jeans would finish with me instead. It’s not like I wanted it, but I didn’t want Cyn to have to go through it.”

Penny was shaking as she finished telling the story, and while Gary had another hundred questions he wanted to ask, he knew it was best to nod and hold her hand and stay shut up.

“And don’t say anything about this to Cyn,” said Penny, getting up off the couch and looking down at Gary. “If she brings it up again, good, then maybe she’ll be able to talk it out and push it aside, but for now let it alone. I’m amazed she said this much.” Penny reached out to touch the wall, as though to support herself, swallowed and continued. “So she really deserves a nice guy like you Gary. She really needs you.”

Penny turned to head back to her room but she stopped and turned back to him, speaking in a strained a very serious tone. “You know, if you look closely someday, at her body, you’ll see a bunch of tiny little knife cuts, like along her back or hips, a couple inside her breasts, and one real long slice inside her ass cheek. All healed, almost invisible, but from nicks and cuts from the knives the guys used on her. She was a fucking bloody mess when it was all over. I thought she was next to dead but she wasn’t even aware of the blood until the guys backed off and I showed it to her.” Then Penny went silent and headed for her room, leaving Gary alone, his mind in chaos, unable to comprehend or picture what his most precious love in the world had been forced to participate in.

Cyn didn’t call so Gary called her. He was a little worried, a little overwhelmed by knowing too much about what Cyn and Penny had been through but also selfishly absorbed with how much he wanted to have Cyn alone in his room again. She seemed happy to talk, seemed unconcerned with what had happened over the previous 24 hours, and jumped at Gary’s new idea for a date: a hiking trip. “Your school year is about to begin and I can work another day off into my schedule, so let’s take off this coming Thursday and hike up to a waterfall I know of.”

Cyn liked the idea, hiking and waterfalls and picnic lunches, but wasn’t sure about getting her parent’s approval. “I don’t want to keep lying about you being my boyfriend, but I’m not going to come right out and tell them I’m sleeping with you either. I’ll just give them the bare facts and we’ll go from there. I’ll call you tomorrow.”

Gary had to go with this, talking a little more and then feeling incredibly self-conscious he added, “And you know I’m kind of head over heels right now. Yeah, the sex too, no need to joke about that, but I’m seriously going to miss you tonight. My mother wanted to change my sheets and I refused. I really like having your smell on my pillow.”

“Yeah, and on your sheets,” laughed Cyn. “Tell you what. Do you have an hour? Like, can you drive over?” “Yeah,” said Gary, but I don’t think your parents want me at your door just now.” “No way,” agreed Cyn, but stay in your car. There’s an alley behind our house. Pull in there and wait for me.”

Gary did as instructed, but he didn’t need to wait. Cyn was already there, crawling into the backseat, then pulling up her dress and showing that she wasn’t wearing any panties. “I’m all yours cowboy.” Gary was overjoyed. As he scooted into the back seat she was an active participant in pulling his pants down, needlessly giving his raging cock a two minute suck and swallow, making him so throbbing hard it hurt.

Cyn took his entire length into her mouth, slowly descending down to where she was even able to suck in his balls and holding it all in for a few seconds, giving Gary a deep throat special. But then she resurfaced, sucking his tip a few times, then sitting up and saying, “You haven’t taken a shower today, have you? I can’t believe guys. I mean, let’s be blunt here. I can still taste all that you and I did last night and this morning.”

Gary apologized, but Cyn waved it off, scooting back and sticking her ass out one side of the car and saying, “OK. My turn. Just take your time. I’m in no hurry. Just remember, you got yours this morning and I was the one left hanging.”

With that hanging over his head like a double-edged sword, Gary did his best, easing himself into her from behind. Cyn’s head and chest was leaning into the back seat but with her feet on the ground, her ass rising up to meet Gary, providing a hot sweet place for him to bury his cock into. Problem was just popping the fat head of his cock into Cyn’s tight hole was enough to want him to blow his entire load. He tried one trick after another, from pulling fully out for a quick rest to pushing deep into her overheated twat and grinding in with as little movement of his cock as possible, hoping to keep Cyn full and happy while holding off on his own explosive finale.

Gary also tried reaching around to finger Cyn’s twat, her cunt wet and ready for both cock and hands to bring her to a climax, but his fingers again came up against the fat knob at the top of her slit. Gary didn’t want to bring it up, he just wanted to fuck Cyn deep into the night, but he had to say it. “Cyn, you’re so hot and wet, I love fucking you, and I want to finger your clit, help you get off, but what is this? Right there, where my finger is. Does that feel good?”

Cyn’s voice was uneven, obviously in the height of sexual need, and she got right to the point. “That’s my clit you asshole. Don’t stop. Don’t you dare fucking cum in me yet.” She began pushing back on Gary’s crotch, starting up a hard fucking rhythm he was forced to catch up with. It wasn’t easy, a hand down her front to continue rubbing at the huge knob in her slit, and his cock pulling back from her ass before thrusting in and being engulfed by Cyn’s very demanding cunt. Gary gave great thanks to a god he wasn’t sure he believed in when Cyn stifled a scream by biting her own arm, pounding back with her upraised ass before then collapsing into the seat, her knees going to ground, forcing Gary to follow her down to the point of kneeling on the gravel roadway. This added effort actually caused him to lose focus, his cock losing its sense of urgency and his need to blow his balls into Cyn’s hot wet pussy.

When he tried to push her ass further up into the back seat, his cock pulled a little too far back and he disengaged. That’s when Cyn crawled fully into the car and told him to join her. She had him sit on the back seat, then threw a knee over his lap and arranged her twat to impale her hole on Gary’s still throbbing cock. That’s when Cyn took over, pumping up and down on Gary for another five minutes, the car actually squeaking in time to her rhythm, Gary’s numb member happy just to be embedded within her hot wet depths. He was OK until she started rising up high and almost pulling off of him, then down a few inches, pushing her hole back over the fat tip of his cock, then back up and down, over and over again until a series of low guttural grunts, a spasm, her body shuddering and finally collapsing onto him, fully impaling herself on Gary’s cock and groaning into his ear.

Gary didn’t care, he was at the edge, and he began pounding up into Cyn’s ass, holding her up with his hands while fucking her from below. He quickly came to a climax and blew his wad, his balls holding back until the last second, then seeming to explode, his cock erupting and pouring it all out into Cyn in a dozen hard streams of cum. It was a wonderful release of all the tension and lust that had been building up all through the day. As he flooded Cyn’s interior, he kept bucking up into her, and Cyn showed her own interest by raising her hips up off of his lap and fucking him back. In the end they just sat there, chest to chest, long loving kisses and moans of pleasure, Cyn whispering out “Two wins for me. This is definitely worth a couple of worried parents”.

Cyn finally pulled all the way off of Gary, moving over to sit at his side, then bending low to suck in Gary’s much softer and very sticky cock. Gary relaxed into the seat, pushing his hips up and out, fighting the impulse to force her mouth deeper into his crotch, moaning out again how wonderful she was. Cyn was there a few minutes, her lips and tongue kissing every inch of his shorter and softer length. At one point she again took his entire cock into her mouth and down her throat, sucking in his ball sac for a few seconds and giving him a pleasure few men had known. She finally pulled back with a cough, then leaning her head into his shoulder, taking a couple of deep breaths and loud swallows before saying, “Yeah, you taste a lot better fresh out of my cunt. I’d advise more showers and maybe I’ll allow you more late night visits.”

All Gary could think of was to say “My god I love you Cyn. I’ll always love you.” Followed by Cyn saying, “Yeah? After what I just did, you better.” As they crawled out from the back seat, Gary pulled Cyn into his chest and said, “Are you sure you can’t spend the week at our place? Like tell your parents its one last girl’s weekend before school starts up?”

Cyn shook her head, saying “Well, maybe, I’ll give it a try, but you know if we’re going to do this I’ll have to pretend to be dating someone other than you. Maybe I can pretend something with a boy at school. We’ll see. At least I get to see you this Thursday, right? Be sure Penny calls and pretends to talk with my mom about going. Make her think it’s a girl’s thing.”

Gary walked her back around the block, saw her off to her front porch and returned to his car. As he pulled himself into the driver’s seat, he became more aware of how wet his pants were, his crotch and thighs wet as through from a spilled coke. He thought back, to how wet his sheets were from that morning, to Cyn pounding down on his lap just a half hour before, and realized he might not want to ever wash these jeans ever again.

Thursday couldn’t come quickly enough for Gary. Somehow little things kept rising up and getting in the way of meeting and enjoying and finally emptying himself into Cyn, just like all those stupid little things they throw at you in a Mario Kart game. He was able to catch her for lunch on Tuesday, really just something at a coffee shop, her mother expecting her home within an hour. At least Thursday was still on, Gary doing his best to plan for everything the long hot hike would entail. And just as importantly Penny was there, both to give Gary tips on what Cyn was like as a girl and would like from him as a possible boyfriend. Gary also held some hope in the back of his mind that his little sister would still provide some grudging access to that most wonderful and unquenchable realm between her legs.

Penny had been happy with her Monday lunch with Keith, the long lunch doing a lot to make her think she had a real boyfriend on her hands. Gary was able to use his hidden spy-cam to listen in on her talking with Cyn, laying on her bed and discussing all the minute little stuff guys pay no attention to but that girls love to dwell on. Keith’s car, his shirt, his cologne, the shape of his hands, of what he wants to do with his life. Sure, worth two minutes of quick review, but the girls seemed to go on forever. Oddly there was no after-lunch sex, Penny seeming to think that holding Keith off for a week would be good for their relationship. Gary had to roll his eyes, thinking girls were crazy and hoping Cyn wasn’t trying to play that same game with him.

After seeing Cyn for that quick lunch on Tuesday, Gary was both head over heels in love and frustrated beyond all comprehension, torn between masturbating to ease the ache in his balls and trying to save himself in case he got lucky somewhere along the hike. Fortunately, his mother had a work assignment that required some in-office hands-on supervision and his own work didn’t need him for the rest of that afternoon, so Gary and Penny got to spend the entire rest of the afternoon alone with one another. Following her past coquettish behavior, Penny didn’t come right out and ask for Gary to do anything, but wearing only a pair of panties and thin tee while playing on her phone in the living room gave her message to Gary loud and clear.

The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.

Close
 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.