Chapter 2

Gary was into his second pot of coffee when Penny finally rose and joined the family for breakfast. His father was already gone to work but their mother wasn’t due in her office until 10 and she was able to hang around and grumble about how little housework her children did during the day. Penny ignored them both, getting some toast and staring at her phone in a wordless display of youthful contempt for age and authority.

Gary broke the silence, saying “You look tired Penny. What did you do yesterday?” Penny shot a glare of a glance at Gary but then went back to her phone. Gary didn’t give up. “Or did you spend the day out with Cyn? Right. You said you guys were going to hit the mall or something. Did you meet anybody else? And where did you eat lunch?”

“Not fast food I hope,” interrupted their mother.

This finally got Penny’s attention, looking up from her phone to glance at her mother, then a long stare at Gary before going back to her phone. But she then shrugged and made it seem that it was all no big deal, saying, “Yeah, I was out with Cyn, you know, to check on shoes. And no not fast food. Actually had a really good salad at the Cheese Cake Factory.”

Gary couldn’t let it rest, and finding it hard to hide his grin he pushed on. “That’s a mile down the road from the mall. How did you two get there? And where did you find the money? I’m the one working and I can’t afford that place.”

He could see Penny’s shoulders tighten and without looking up, pretending total interest in whatever she was viewing on her phone she gave out a hard terse answer. “We met a friend of Cyn’s. He drove us there. He even paid. He then drove us back here. That was it. Alright?”

“Yeah, fine. Just wondering,” replied Gary. He rose and turned away to hide the large grin on his face, saying, “Well, I’m off. A full day of work today. Pretty rare. See you guys tonight. Bye mom. Love you sis.”

Work for Gary was simple: count and organize and stock and count again. It was basic warehouse work on the edge of town, out of sight of the people who consumed all the stuff that made American life so wasteful. When he had started the job just before graduating high school, Gary had expected to work part-time for a while before finding a dream job somewhere and moving into his own place and living the good life. Reality turned out to be more cruel than advertised and two years later Gary was still there, working part-time while hoping a little college would boost his place in the world.

The good thing was that his employer recognized his talents and his honesty. Gary never stole, either goods or time, and he always showed up, even when the manager threw in a surprise change of hours. It didn’t take any math or stats to work the devices or computer databases, finding what had come in, knowing where to put it, and keeping an eye on what was going out. Gary probably knew more about the inventory of the warehouse than his manager, though he was smart enough to never say so. Gary was good enough to push for a full-time slot, but after two years he had realized that there was more to life than shunting crap from one place to another. The old timers in the place were overweight and lived for a favorite sports team or video game. Gary had realized there was more to life. He didn’t know what, but figured college was still a better place to pursue the unknown than behind the wheel of a forklift.

Gary was well paid for his time, and much of that only required him to engage half of his brain. The other half could wander around, thinking about a favorite television program, what he needed to do for homework in a college course, or how deep in hell he was going to be tossed for spying on his little sister and her most fuckable friend.

He knew that what he had done was wrong. Worse was what Gary was considering to do with the video mashup of the two girls and the men they had brought into Penny’s room. Gary knew that he should delete the entire thing, perhaps after watching it again a time or two. What kept coming up in his mind was using the video as leverage, as a means of levering open his sister’s legs and forcing her to do as he wished. Any good brother or friend wouldn’t even consider such an action, but there it was, sitting before Gary and enticing him, forcing him to make a choice that would define just what kind of man he grew into. He knew the right answer, but still he sweated it out, sitting on the line and looking at one side and then the other, knowing long before how he would act and ashamed at his pretense.

Thing is, Gary really was a nice guy. Average in height, his youth and good diet only adding to his handsome all-American look. He had friends, a job, a future. One thing missing was what one friend called “a lack of charisma,” or possibly him bing “too nice” and not “forceful or sure of himself.” That was fine in high school, but Gary did wonder if his being “passive” was the reason for being passed up for a raise earlier that year. Or maybe why a girl he had a crush on in high school remained only an acquaintance and not the love of his life.

It had been a simple do or die moment that Gary continued to wake up to and ruminate over in the middle of the night. Gary thought he had done the right thing, followed the rules, but obviously he had missed out on the new edition of rules to make out by. The moment had come when he and a handful of others had gone camping for a long week-end at a lake a two-hour drive up into the mountains. Two large tents, boys in one and girls in the other, and everybody knowing who they were to be paired off with. Gary and Jill knew each other, had gravitated closer and closer and this camping trip was going to settle it all. They had already kissed, Gary even coming to know the feel of Jill’s ample breasts, albeit only through her blouse. Another date or two would have put him over the top and into her pants, but then this opportunity to go camping had come up. Forget the dating and make-out sessions in the car. This promised a long weekend of fun and frolic that would cement the two lovers hip to hip. Gary couldn’t wait.

The drive up was fun, the hike in to the lake easy for the youth, and after a campfire dinner and some group fun, the chosen pairs had gravitated to private spots in the darkness where they could continue making romance. Gary had pulled Jill in with kisses and slow advances down to suck on her breasts, though still through a layer of cloth. That’s when he attempted to roll her over onto him and push down her shorts. Jill seemed fine with his moves, and then she wasn’t, suddenly saying no, telling Gary she needed more time, and he acted the good chivalrous boy and pulled back.

Then Jill suggested they go get their sleeping bags and return to the edge of the meadow to enjoy the stars and darkness together. One of the couples had already taken over the girl’s tent, leading Jill to crashing their party, wishing the pair good luck for a “second cuming” and promising no more interruptions. Gary took this to mean that Jill was ready for some action of her own, but in the meadow she zipped up her bag and lay back, seemingly happy to just count the falling stars and talk about all the animal noises that surrounded them. Gary thought it was a wonderful bonding moment, a time of growing closer to a girl he really cared for, but some hours later he woke up alone, Jill obviously long gone. Cursing himself for falling asleep while holding Jill’s hand, he returned to a darkened campsite, crawling into the boy’s tent only to be grumbled at by the other couple who were trying to get some well earned sleep.

The next morning Gary and Jill and another couple went for a long hike while the last couple remained behind to “toss stones in the lake.” On the hike, Gary’s friend pulled him back and asked what had gone wrong. “Jill kind of hinted that you wimped out. You went to sleep on her? Seriously? I thought you were into her.”

Gary made his excuses, pretended that he and Jill remained tight and ready to roll, but it became painfully obvious that Jill no longer considered Gary a viable candidate for sexual relations or much of anything else. On the drive back she even sat in the back third row with one couple, leaving Gary to sit alone in the middle set of seats. Everybody pretended nothing had happened, but it was over.

It was a crushing moment for Gary, and every time he replayed the weekend over in his mind, his gut fell away and he felt lost, unsure of what more he could have done. He limped through the rest of his senior year, sometimes with a girl at his side, but never a full-time girlfriend with bedroom privileges. He eventually did enter into a serious relationship, six months of ever deepening feelings and even week-end access when they could find some privacy. It looked promising, but they suddenly woke up and mutually agreed to go in different directions. Other much shorter relationships ended the same way, Gary growing weary of the games and deciding to just focus on school and finding a decent job.

Jill remained in the back of his mind, perhaps marring his sense of self, and always making him wonder what he had done wrong. If nothing else, trying harder, being a little more assertive, and of course not falling asleep. We’re not talking kidnapping or rape here, just working on a few lines and a few more moves that could take Gary past the first “no” and hopefully wind up with the necessary “yes.” Friends in high school had far too many tips on what he needed to do, and it all sounded like BS. Yet Gary was serious enough about self-improvement that he had gone to Penny for advice. All she did is roll her eyes and tell him to just be himself, as if that was going to be any help.

So, there he was, the nice guy with a video more powerful than a nuclear warhead in hand, and unsure of whether to destroy it or use it for the greater good that was Gary. On the drive home from work Gary knew what he would do, but he had no idea how to actually carry it out. There was certainly no manual on how to blackmail a younger sister into doing what rightfully should get Gary thrown into jail. Was he really hoping to bone his own sister? Yes, and hopefully get into Cyn’s pants as well. But how? He’d just have to wing it.

After Gary got home toward dinner, he quickly went to his computer and searched to see if his baby sister had done anything more to wet his cock, but the video was all pretty tame. She did spend a lot of time in her room cleaning, including using the rug shampooer, wiping off the area of the bed Cyn was supposed to have reached a climax on, and then organizing things, perhaps in an attempt to keep her mother happy. She tipped the stuffed animal with his web cam over which now pointed to a side wall, but otherwise she didn’t notice anything unusual about the stuffed penguin with a glass eye in it’s neck. Gary could fix that. Now was the time to confront little sis and lay his cards on the table.

He kept it cool and low key through the evening, his parents going to bed earlier than the kids, normal, though Penny quickly followed. Gary had tried to get Penny to sit and talk about what she planned on doing during the summer break, hoping to somehow bring up what he knew she and Cyn had been up to, but she suddenly disappeared into her room. Still unsure and his stomach in knots, Gary pulled her up on the computer’s all seeing eye, though she spent most of her time in chat rooms and watching some online videos, and all with her top on. Then she went to bed.

Now or never. Gary gave her two minutes to settle into the covers before making his move. Wearing only a pair of boxers, he took a deep breath, then as noiselessly as possible slipped into Penny’s dark room and over to her bed, barely having time to lift the covers before she sat up and gave out a “What? What the fuck? Gary? What’s going on?”

Her trust in him allowed Gary the time and space to say, “Yeah. Shh, it’s OK Penny. But we’ve got to talk.” He acted as though it was a normal thing for him to slip under the covers and snuggle close to his sister. She pulled back and against the wall, and in the dim light coming through her window Gary could see Penny was up on one elbow, looking at him with a questioning glare and probably with a growing distrust of men.

Gary just wanted to just snuggle and talk in low tones about how incredibly hot and sexy he thought she was, eventually pushing his boner into her and making use of all the joys she had shared with the two men just the day before. But that had to wait. First he had to lay out the ultimatum. “Listen, Penny, I know what you and Cyn did yesterday. You know, with the two guys, Jason and Keith. I’m kind of shocked, I really didn’t think you went in for that. Seriously, I didn’t even know you weren’t a virgin, I’m that clueless. And Cyn. Shit. Talk about a turn-on.”

Gary had barely gotten those words out before Penny bolted straight up, hitting his shoulder with an ineffectual fist as she whispered, “You fuck! Who told? Do you know Jason? Did he call you or something? It’s none of your business Gary, so get the fuck out. Get away.” Penny was obviously panicked, shaking, and probably worried about just who else knew what she did in her bedroom when nobody else was around.

“No, no, nothing like that,” said Gary, trying to sound calm. “Just listen, would you?” Penny quieted, but remained sitting upright, tense and staring knives through the dark at her older brother.

That’s when Gary sat up next to her, looking over into her darkened face and described everything that had gone on. He talked for maybe five minutes, bringing up some special points of the afternoon, like how easy it was for her pussy to envelop Keith’s fat cock, Cyn forcing Penny to eat out her cream-filled hole, Cyn’s wetting of her bed when she enjoyed her own special orgasm while underneath Keith, and of course Jason ending it all by relieving his bladder into Penny’s vaginal depths. Gary held Penny’s hand, could feel her shaking, and could certainly hear the anger in her voice as she said, “That’s private,” “You have no right,” and “How the fuck did you know?”

Gary didn’t want to give it all away, but he had to admit some, give some proof, and he opted with the easiest and best version of only partial truth. “It was your computer. I’ve been able to check you out through your computer camera lens for the past month. It’s all motion activated, saved online for me to check it out when I have time. Nothing special. Just looking in on you. Yeah, spying. Mostly it was to check out Cyn, see what she was like when you two were alone. Didn’t think I’d be given access to a full on orgy in your bedroom though. Shit Penny. How often do you do that? Was it for money or what?”

Penny slid down into the bed, turning her back on him and facing the wall as she said, “You’re a real pervert Gary. You shouldn’t do that. I bet it’s illegal too.” This is when Gary slid down behind her, on his side, one arm over her shoulder, his crotch and obvious erection pressing into her panty-clad ass. “Yeah, I agree. Pretty low life shit. But you didn’t answer my question. Seriously, do you do this a lot? And not for money I hope. You don’t solicit guys at the mall and bring them home, do you?”

Penny remained rigid as she continued to face the wall, tense and terse in her answer, but at least she acknowledged him. “No, nothing like that. This was really like the first time anything like this ever happened. We just happened to meet Cyn’s old boyfriend, like from way over a year ago, and he took us out to lunch. We only came back here because Cyn had said she’d give him something to remind him of their time together if he took us somewhere nice. We just thought she’d have to blow him in the car. It kind of got out of hand.”

She turned in the bed, removing her ass from Gary’s roving cock and faced him, saying “You’ve got this on video? Like you’re going to post it on your web page or something? You’re not going to show it to anybody, are you? Don’t do that Gary, please?”

“It’s OK Penny,” said Gary, and without thinking he leaned in and kissed her lightly on the lips. “I’m not a monster. That’s why I’m here. I just wanted to talk to you about it, maybe get some ideas from you.” And with hardly a pause, Gary rolled into Penny, rolled over and on top of her, his knees and hips taking up the space between her legs as he bent down to give her another kiss. This time Penny turned her face away, saying nothing, but obviously understanding everything.

Gary didn’t try to hurry it, relishing the feel of Penny’s half-naked body lying under his. He kissed her cheek, went lower to kiss her neck, then slid down to push up her shirt so that he could tongue and suck in her breasts, delirious in the simple joy of sucking up mouthfuls of her soft womanly flesh while tonguing and nibbling on each of her nipples. Then back up, his head above hers, Gary reaching down to arrange his impatient boner to slip under Penny’s panties and press into her furry slit. Penny had a hand on his head but otherwise didn’t help Gary in any way, but she also didn’t need to. As he pulled the edge of her panties to the side and pushed deeper within her thighs, Gary’s raging boner could feel her wetness, felt her warm liquid lips as his cock moved in to nestle within her labia, moving back and forth a few times through the warm wetness men intuitively seek from a woman. Gary then pushed down, angled the tip of his cock down, pulled up on Penny’s ass with one hand and pushed in and beyond all boundaries of decency to make her his own.

It was as though Gary’s cock had been enveloped by a hot wet towel, sucked into a hot liquid fleshy realm Gary never had the thought to dream of until then. It was everything he could want, and with each push of his cock into her, each inch buried within Penny’s pussy, Gary moaned and knew he would never be able to stop. She was tight enough, but warm and wet, slick with hot juices his cock found easy to push into, almost as though her cunt was sucking his cock deeper with little effort on his part. Within a minute Gary’s cock was pushed deep within her, his balls pressed tight against her ass, and without a thought Gary whispered out, “Penny, my god Penny, you’re so hot, so fucking wet. Those guys were right. You feel so good.”