Chapter 9

As school started and the weeks began passing by, Gary found himself overwhelmed by life, as though he were caught in an open ocean, navigating events and concerns as though they were rolling waves trying to overwhelm and drown him. True, he had Cyn at his side and often on top of him, but life has its way of overwhelming even the luckiest of men. His boss wanted to give him more hours but no benefits even as he took on an extra class at the college. He had to finish applying to a couple of additional universities he hoped to transfer to, was still trying to work out a future life with Cyn, and of course in the back of his mind was the obsession that was Penny.

If anything, work was fine, college could be dealt with, and Cyn was a joy that made life wonderful. Even as he and Cyn danced around the idea of becoming a real couple, of even thinking of announcing it to the world, Gary couldn’t shake the idea of Penny saying one thing about Keith and doing something else entirely over at Simon’s parent’s house. At least Cyn was reporting that Penny was showing up at school, that they even ate lunch together twice a week, but the weekends were something else. Penny often got up early on Saturdays to jog, yet often not returning until toward noon. Gary didn’t think Penny was spending all her time preparing for a marathon.

The thought had crossed Gary’s mind that he was jealous, that some other guys were getting into Penny’s panties even as he forced himself back from making any more moves on her. She continued to talk about Keith as her boyfriend but without a mention of her occasional trysts with Simon, and for a few weeks she did nothing to incite lust in Gary. Even with Cyn forever in his mind Gary of course wanted Penny in the most base and sexual of ways, but he kept himself under control and even when they were alone together, Penny acted like the perfect virginal girl her parents thought she was.

Until a few days after her small and simple sweet-seventeen mid-week birthday party. Just the basics, barbeque in the backyard and cake for dessert, then light talk and all the guests going home. By ten even Gary had crawled into bed, thoughts from the previous day’s lecture in one of his classes filling his head. There were of course visions of Cyn sitting next to him at the short gathering, only giving him a peck on the cheek as she left with another friend. His college class and images of Cyn were battling for space in his brain when Penny opened the door and slipped under the sheets to join him.

“Penny. What’s going on?” Gary whispered, pretending ignorance as his arms reached out to pull her in. He wasn’t really surprised to find that she was naked, and as his upper arm wrapped over her back, somehow slipping down to grasp her panty-clad ass, she snuggled closer and kissed him. Her mouth seemed ravenous, her tongue searching for his, and all Gary could think of was how enticing her perfume was. With Penny reaching down to grasp his suddenly raging boner, Gary had difficulty even remembering what Cyn looked like. But he somehow found strength to put up some token resistance, to use his hands to push against her chest, to feel out her perfect firm breasts and push back, saying “I want you so much Penny, but I really can’t. Cyn is just too important to me.”

Penny paused, leaning in to bite the lobe of his ear, saying “Okay, if you say so, but you know I’m really horny. Keith wouldn’t come to the party and I can’t see him again until next Saturday, so I just thought you could help. Just for tonight, alright? And don’t worry about Cyn. No way I’d tell her about any of our get-togethers. She’d slit my throat. So, don’t worry Romeo. This is just between you and me.”

Gary almost brought up Simon, wondering why she didn’t just sneak out and meet him for a little action in his car, but Gary found himself without control or morals. After giving Gary another kiss, Penny turned away from Gary, facing away from him, but pushing her ass back into his crotch. Then she lifted her leg and reached down and back, grabbing his very hard shaft of flesh and pulling it up into the hot wet slit between her thighs. Gary didn’t help her but he didn’t fight her either, mesmerized by the feel of her hand as she held him and rubbed the head of his cock back and forth through her very wet pussy. Without consciously thinking about what he was doing, Gary reached over to put a hand on Penny’s breast and then gasped as she thrust her ass down and onto him, impaling herself on his cock, easily sucking in the first few inches of his leaking shaft.

Gary was on edge, overcome by the very real lust he felt for Penny, but also angry about how easy it was for her to slip in and use him, taking him over even when she knew how much he wanted to stay true to Cyn. With his cock bathed in the hot moist folds between her legs, her pussy seeming to massage his cock to greater heights of need, all Gary could do is join Penny, fucking her as she fucked him. His cock quickly buried itself inside of her, his balls pressing into her ass, his hands pulling her in at her breasts as her words filled his ears: “Fuck me baby, just fuck me.” Over and over again, a phrase he had never heard from her before, but Gary didn’t care. He would do anything she wanted.

His sexual need dominated the moment, and only a few minutes into the sexual frenzy, Gary reached down to pull tight on one of Penny’s legs, pulling it back and over his hip as he reached his climax and poured himself into her, his balls and cock pulsing in tandem as his thick liquid seed filled her vaginal depths. It wasn’t a soft and caring and controlled orgasm. Rather it was a violent fuck and uncontrolled unleashing of all of Gary’s needs, pounding into her ass and claiming her pussy as his own, uncaring of what anybody, even his parents or even Cyn might think about him. But then, after it was over, as his balls pulsed out their last drops into her, Gary finally slid back, pulling out of Penny’s overflowing hole even as he bent over to kiss the back of her head. “Are you okay Penny?”

Gary realized that in his eagerness, as his lust overwhelmed him and he laid into Penny’s hot sweet ass and poured himself into her, he hadn’t noticed that she was crying. Not loud weeping, but soft, a few tears being felt on her cheeks as he leaned in to kiss the side of her face. “Did I hurt you?”

“No, you dumbass. You were fine. Kind of nice to feel you really fuck me, you know? Like I’m getting to know the real you. I’ve kind of missed you. Either way you come off as a selfish asshole, always getting what you want. Still, be kind of nice if you could help a girl out.” Here she pulled one of Gary’s hands down from where he was massaging her breasts to the wet slit between her thighs. Gary knew what she wanted and was happy to oblige, feeling out her standard-size and very hard clit and doing all he could to make her happy. Penny leaned in to kiss him, to kiss her own brother, becoming very excited with his finger action, first moving back and forth with his hand, then finally writhing, pushing hard against him, almost fucking his hand as she reached a climax of her own. It was a strained and silent orgasm, a shuddering release that announced itself to Gary with a low moan and Penny pushing his very wet hand away.

They lay together in peace, sharing labored breathing and the occasional feel and touch and soft kiss, two illicit lovers who knew they would soon have to part. Gary thought Penny would leave, roll out of the covers and return to her room, but she instead scooted down, deeper under the covers and took his sticky and cum-covered pole into her mouth. Gary threw a leg over her side, holding her head in close with his knee, slowly fucking the mouth that had started sucking on the first few inches of his cock. It was a wonderful feeling and even though Gary fought against his desire to push it in deeper, to fuck Penny’s face as though he was pounding her cunt into the ground, he was able to hold back and just enjoy her oral loving.

His orgasm rose quickly, Gary telling Penny that he was going to cum in her mouth. He feared she would pull back and have him ejaculate onto his sheets, but she instead pulled herself up even with him, easily arranging herself so that he slipped into her very wet pussy, fucking him for a final few seconds before he lost himself in his second orgasm of the night. Riding him from on top, Penny didn’t stop until he had filled her to overflowing, his balls empty, his cock starting to soften yet again. As she came to accept that Gary had no more to offer her, she lowered herself onto his chest, her head lying next to his, the two yet again happy to simply be with one another.

The following morning Penny acted as though nothing had happened, as though their platonic brother-sister relationship had returned. Gary sighed and realized that such a double standard was going to grind him down and worried about what had made her invade his room, what was going through Penny’s head.

Time passed and another week rolled by. Cyn did turn 18, and though Gary was not invited to her birthday party, she was able to slip out later that night to make sure he got a slice of her birthday cake. She even went down on him for a long loving suck, swallowing all of their shared intimate secretions, making him ready for a long enjoyable second slice. True, she was 18, but she was still her parents’ daughter, so she had to leave him for the care of home, twat full of all his liquid loving.

As fall deepened Keith continued to be Penny’s one true love, except for two additional visits to Gary’s bed. That would have been fine with Gary if Cyn hadn’t also reported that Penny was starting to arrive to school late and had even missed a couple of school days in the middle of October. Knowing how much Cyn disliked Simon, Penny disclosed nothing about her absences, which was itself an indication of where she was disappearing to. Gary didn’t know how she could stand the strain of playing around with Simon behind Keith’s back, but she seemed adamant about not leaving Simon, at least not for the foreseeable future. Of course, he wasn’t sure how much longer he could continue cheating on his one true love. Gary worried about Cyn finding out, but he found himself unable to control himself whenever Penny had his dick in hand and mouth.

Cyn often visited him as well, sometimes studying for an hour with Penny, other times fully accepting of Gary ripping her clothes off and emptying his balls into her within five minutes of her entering the house. His mind was torn, his cock unable to make a decision, and Gary just went with whichever beautiful piece of twat happened to be in front of him. His body was happy, but his mind was a guilt-laden mess and his heart torn. In the end he did the most dishonorable thing and made no choice at all.

He also continued to watch Penny and sometimes Cyn through his hidden eye. Not so oddly Penny never put a piece of tape over the camera lens on her computer, sometimes covering it with a piece of clothing but other times seeming to give him a show meant to tease him. She seemed completely unaware of his hidden web-cam on the shelf, but sometimes turned her computer screen to view her playing with herself, sometimes just a finger, sometimes her ben-wa balls, and once with a larger than your average banana.

Then came a night when he came home from a very long day of school followed by work and checked his computer to watch Penny’s bedroom antics only to find Cyn masturbating in Penny’s room. Penny was there, sitting on the bed as Cyn applied the suction cup of some bluish phallic shape to a book on the floor, then rode the dildo for a good ten minutes, all with the computer screen pointed directly at her. It ended with Cyn reaching an orgasm, Penny helping Cyn off the dildo with a comment about how her liquid release ruined the book. Of course then Penny took a ride, both girls obviously aware of how visible it all was to Gary’s spy eye.

That should have been it, more than enough video to fill Gary’s dreams for the next week, but the girls weren’t done. After cleaning up, Penny brought out some special equipment meant just to trim and smooth the thick gardens between their legs. The following hour was spent with the two helping the other maintain and control and artfully shape the furry bush that framed their feminine delights. Gary was mesmerized, watching the two trim and shave and talk about things men weren’t ever supposed to know of. There was a mention of getting a wax job, but to Gary they already sported the most deliciously sexy looking twats he had ever seen.

He noticed that Penny had her upper groin area trimmed as low as it could go, clean shaven all the way down to the upper edge of her lips, leaving only a thin edge of fur on her minimal labia. Cyn was more accepting of her pubic garden, something Gary was quite happy with. Cyn trimmed and shaped her upper patch of hair, a beautiful V-shaped patch of thick red forest riding well below her belly button. She also left a bit more around her labia than Penny, her pussy trimmed and under control but with a delicate covering of reddish fur hiding the thick labia that took up so much space between her thighs.

He knew he was being played with, tortured by the girls. Penny sometimes asked if he had seen enough, finding it funny to know what kind of an effect she had on her big brother. Cyn had never said a word, but he knew Penny had given Cyn fair warning of Gary’s power over her computer eye. If Cyn wanted to bring it up then he’d be fine with it and love her all the more. If Cyn was just being played by Penny in order to tease her brother, then he didn’t mind that either. As long as Cyn never showed up in any video with another man on her tail, and as long as she continued finding ways to have him empty his balls inside her, then she could play with all the plastic cock she wanted. If anything, between the girls riding it out with the dildo and then spreading each other’s legs for a trim, Gary was left overwhelmed by sexual desire and aware of how intimate his knowledge of the girls had become.

It all came to a head, so to speak, just before Halloween. Two huge events rolled over Gary, and he couldn’t hide from himself or keep up the charade in front of Cyn for another day.

The first was Penny sliding into his bed late on a Saturday night. Gary was frustrated at having to work half the day and being unable to see Cyn, so having Penny slip under his covers startled him wide awake. His cock was instantly hard, his hand pulling her ass in even as his mind was forcing his mouth to tell Penny to get out. Then he listened.

“It’s okay Gary. I just wanted someone to hold. I hope you don’t mind.” Gary was torn, happy to pull Penny closer for only a supportive hug even while a more petty part of himself was cursing her for not forcing him into fucking her. He mentioned that maybe she should call Keith, but Penny said, “Keith is busy and can’t see me until tomorrow, and I’m not sure I want sex anyway. Could you just hold me? Keith will want a quick fuck before we do anything, he always does, but right now I’d just like you to hold me.”

Gary probed, asked if something was wrong, told her he loved her like a sister and would always be there for her, all the while pulling her close, kissing her hair, and perhaps not at all subtly grinding his crotch back and forth against the inside of her thighs. She said little, only that she was trying to figure out her relationship with Keith, but then, acting on the inevitable, reached down and began giving Gary a hand job.

He told her no, that she didn’t have to, but she just whispered “bullshit, you’re wetter than I am” and kept up the motion. Penny knew just what to do, when to let go and turn her back on him, pushing her ass back and without a word inviting Gary to push his straining cock into her always wet and welcoming folds. He tried to hold off, but Penny reached down and back, rubbing the tip of his cock back and forth within her slit. All of his pretend morality was pushed aside and Gary slid up, pulling back on Penny’s hips and impaling her on his straining rod. Within a minute he was pounding his balls into her, demanding just another inch of depth into Penny’s pussy when his cock exploded, the contents of his balls being safely unleashed into her. He had to finish it, rolling fully over onto her back and fucking his way as deep into her cunt as he could before finally feeling empty and complete, collapsing down onto Penny’s silent form. He knew it was wrong, he always felt it was wrong, but it always felt so wonderful to empty himself inside of her.

“Better now?” Penny asked, a bit of humor in her voice. Gary held her close, pushing his cock into her, saying “You didn’t have to do that Penny. Really. You shouldn’t have done that.” Penny whispered back, “Yeah, I know. Last time, I promise.” Gary smiled. She had said that a number of times before.

Then she was quiet, and as Gary rolled off of her, onto his side and wishing for a long night’s sleep, Penny rolled over to face him, pulling Gary into a hug and whispering, “Do you love me Gary? I mean, sure, like a brother, but you love me, right?”

Gary could only do a quick search through his muddled mind for an acceptable answer, wondering where Penny was going with her thoughts, finally sticking with what seemed the only answer he could give his most beautiful and fuckable sister. “Of course I love you. I always will. Not like Cyn, but still just as close and important. I’ll always love you.”

Penny was silent for a long minute, Gary wishing desperately for sleep but knowing Penny had something more on her mind. He finally realized it was up to him to ask. “What’s wrong Penny? Like last time? Is it Keith? You said you’ll see him tomorrow. Don’t tell me it’s Simon again. What happened?”

Gary was only throwing stones into the dark but he seemed to hit on something. Penny held him closer, her head tight to his chest, murmuring “Yeah, something like that.” He urged her to tell him, pulling her up, kissing her hair, again enjoying the smell of her perfume, and forcing himself to listen to her talk. It took a lot of back and forth, Gary sometimes having to prod Penny to speak, alternating between kissing and touching and massaging her as he urged her to talk, but in soft hushed tones she finally admitted to him what he and Cyn had both feared.

“Keith is OK, and I really like him, but you know Simon really gets me. I know you think he’s just a controlling asshole, and you’re right, but until last night I really thought he was everything I’d ever want. I know I told you that he and I left each other when he got married a year ago, but we’ve kept seeing each other. I mean, his wife got pregnant, had a kid, but we still couldn’t get enough of each other. I thought Keith would end all this, become my boyfriend and that would be it, but I just couldn’t let go of Simon. Like almost every week, but not just for sex. For a long time he was making plans for us to take off together after I finished high school, just like you and Cyn. That’s the way it was until a little while ago.”

This is where Penny went silent for a few minutes and Gary had to prod her, remind her that she had to finish the story. “I had gone over to Simon’s last week, his parents’, and we did what we normally do. Sex, talk, made a grilled cheese, and I expected us to play around a little more before he took off back to work and his wife. But then he wants me to drive over to a friend’s place with him, and while visiting there he talks me into having sex with his friend. We smoked a little, and then he held me from behind while sitting behind me on the couch, and then his friend pulled my pants off and then pulled me into doing a kind of lap job. We wound up on the living room rug, for a couple of hours at least. It wasn’t so bad but I really thought Simon was over all that group sex stuff, that he would be happy with just me. I guess not.

“What really gets me is that it was kind of a turn on for me, and he knew it. He said he loves me, that he just enjoyed watching me fuck other men, knew how much I liked it, and in a way he’s right. It was fun, having sex with another guy, but always with Simon there, and even with the other guy it seemed really intimate and like I was doing it for him. But then last night kind of changed everything... “ And Penny went silent and Gary thought that was it, worried about her but also embarrassed about his hard on, his cock getting hard from listening to Penny recounting the many ways Simon had her fuck his one very lucky friend.

Penny suddenly started talking again, droning on, emotionless, detailing what Simon and his friends had done with her just the night before. “There was school yesterday, but I cut class. I mean, I went over to Simon’s and we played around, just him and me, and then he talked me into joining him and another guy for lunch, and you know where that went. Then Simon decides he wants to go to another friend’s place where they were going to have a Halloween party. So, he drops me off here but picks me up again about 6. Remember? I just told mom I was going out, maybe see Cyn, be back soon, blah, blah. Whatever would make her get off my back.

“The party didn’t begin until later, but me and a couple of his friends wound up in the back bedroom for a couple of hours. Simon was with us for a while, but not all the time. I didn’t even know when the party really got started until I had to take a bathroom break. There I was in nothing but a pair of panties, walking around and looking for Simon in the middle of all these people. I knew some of them, mostly the guys. They probably thought I was like Lady Guinevere or something, guys patting my ass and all the girls with their eyes bugging out. Simon finally found me and we headed back to the bedroom.