Chapter 10

In some ways Gary’s declaration of love for Cyn had changed nothing. Cyn continued living with her parents and going to school while Gary juggled work and college. Even with all this he somehow found time to disappear into his bedroom with Cyn a couple of times a week. His most difficult task was having to face his parents, sitting them down only a day before Thanksgiving and telling them that he was going to move out to live with Cyn and that he hoped to marry her some time the following year. His mother was the one who voiced the most doubt, tinged with a bit of recrimination toward Cyn, but he assured them both that he would not be swayed, either from his love for Cyn or for his desire to finish college.

The next day Cyn showed up at Gary’s front door, tearfully saying that her parents refused to have him over while pushing for her to wise up and end their relationship. Gary was proud to bursting when his father insisted on having Cyn stay with them for some leftover turkey, Penny playing up the “now I have a sister” routine. His mother might not have been willing to openly invite Cyn to stay the night in Gary’s room, but she knew how to be gracious.

December arrived and with it one last revelation from Cyn. Gary had a hidden room within his mind, a place for secrets he didn’t want Cyn to ever find out about, so when she bit her lip and leaned in to tell one more story about her past, he really couldn’t do anything but hold her and worship her all the more.

They were trying out their soon to be apartment, with housemates but with a bedroom all to themselves, and with a queen sized bed newly bought from the parting renter who had found work in another city. Gary had picked Cyn up from school and they had just finished a long hour of reacquainting themselves with each other’s body, something they tried to do at least a couple of times a week. This day was special because they had so much space, a large bed to roll around on and without any need to hold down the noise or stifle their moans. The sheets were questionable, the quilt old and leaking stuffing, but it was all theirs, and they had spent the hour doing their best to mark their possessions with their own special scent. That’s when Cyn leaned in, put her head on Gary’s shoulder and said, “Gary, I’ve gotta say something, I mean admit something, something I should have told you earlier but just couldn’t.”

Gary froze, paused, but then turned his head to kiss her rumpled mass of red curls, saying “You don’t have to. Unless of course you want to admit that you really want to go down on me and start dinner early with a few choice ounces of protein.” That made Cyn laugh, sputtering out a few choice invectives before finally coming back to his arms and forcing him to take her seriously. “No, dumbass. Listen. I know I’ve come down on you for blackmailing and screwing your little sister. Now I think I’d better admit something of my own.”

This again made Gary pause but he wisely said nothing, waiting to hear what made Cyn so serious. She got right to the point. “Remember Penny telling you about my friend, the guy down the street I had a relationship with for a couple of years? That wasn’t just some high school guy or creepy neighbor. He was my uncle, my father’s brother.” Gary again froze, a torrent of potential incest stories crowding his mind. His heart rate doubled, his mouth grew dry even as he tried to think of what he could say, but he was also aware that his cock had suddenly leaped out and was pushing against Cyn’s thigh.

She pretended not to notice, staring at his chest of brown hair as she continued. “He had been married, I mean was married. It was just a couple of years before high school when he suddenly took what you could call a real interest in me. I kind of found him easier to talk to than my own mom or dad, and when I made comments about boys and dating and stuff, he kind of sat me on his lap and told me everything he thought I should know. I mean, literally. He showed me his and invited me to explore all I wanted. It started off really slow, like him showing me how guys masturbate and what a guy’s cum is like, but there was also this feeling of caring, of us developing a relationship behind his wife’s back.”

As Gary listened he could feel Cyn shaking, knew that this was a story and a memory that held a lot of meaning for her. But as she talked he could also hear Penny saying something similar about Simon, about her own relationship with an older man. Gary didn’t know how much was true or how much Cyn was holding back, but he kept his doubts to himself and urged her to say more.

“So, we never had sex, not real sex, like him fucking me. He said that wouldn’t be right, but we kind of did everything else. You see, his wife was in this car accident, was in a coma for a long time, and I think he felt really guilty about being with me. At the same time, I really felt for him, felt sorry for him, and I just wanted to do everything I could for him. He was lonely and in need and it just seemed normal for me to want to, well, you know. I think we would have wound up going all the way but somehow my dad found out and hit the roof. In his mind his brother was fucking me while his wife was in a hospital bed, and it got so bad that he moved, like to another city.” Cyn continued looking at Gary’s chest, running her fingers through the short but thick forest of curls, silently waiting to hear what Gary had to say.

Man that he was, Gary was more aware of his hard on, his cock stiff and leaking under the covers, wondering if he could get Cyn to demonstrate what she had so often practiced with her uncle. He also wondered if she had lied about not fucking her uncle and if she still saw him from time to time, but he knew he couldn’t ask about that. Gary stuck to a safe neutral question, asking “Is that why your father is so upset? Because he still sees you as his little girl, with me as an older man taking advantage of you?”

Cyn again chose bluntness in giving her answer. “No. He just doesn’t like you, but he also doesn’t like to be reminded about me having sex. My uncle never hesitated in reminding me that men could think of nothing but every time I walked down the street, even fully clothed. He admitted his lust for me but at the same time he never forced me into anything. I would have fucked him a dozen times over but he always told me to wait, to find the right young man before losing my virginity. Of course, he never hesitated to pull his cock out and have me lick him off.”

Cyn suddenly blanched when she remembered who she was disclosing these secret memories to, apologizing for being too frank and then giving Gary a quick kiss when he said she had nothing to apologize for. She went silent for another minute before sitting up and looking down at Gary, saying “So, that’s it. I learned how to suck cock by practicing on my uncle. And just in case you’re wondering, no, I don’t see him anymore. Haven’t for almost a year. Any questions?”

Again Gary showed incredible maturity and wisdom (in his mind) when he understood that there was really only one answer to this. “No, not from me. Like you said, we’ve both got a past, and it’s really none of my business. I’m always here to listen when you want to talk, but most of all I just want to love you.”

With this Gary pulled Cyn up to give Cyn a long kiss, fighting the urge to go low and do the same to her nipples while expecting Cyn to remind him that they had to head back to their respective homes. To his surprise, as she folded into his arms his cock sprang to life when she said, “And if you think our future housemate could spare it, maybe you could go search out a little olive oil.” Gary’s eyes shot open with immediate understanding and two minutes later he was back and with only a small amount of added lubrication found himself prying open the jewel so long hidden within Cyn’s most perfect ass cheeks.

Even with the oil, aided with the sweat and secretions of the previous hour, Gary had to take his time in slowly prying Cyn’s anus apart. As the leading inch of his cock suddenly popped into her ass, both of them gasped, but rather than try to pull away Cyn actually pushed back, raising her ass up and impaling her rear on another inch of cock. Gary took it slow, enjoying the tight grasp Cyn’s ass had on his stiff rod, yet focused on pushing in a little deeper, following a guttural urge to embed himself inside of her.

At first Cyn was releasing low groans as Gary went deeper, reaching out to grab the edge of the headboard, yet continued pushing her ass back in tandem with Gary’s slow and patient thrusts inwards. In only a few minutes, he was pushing his painfully tight balls into her rear, short but deep thrusts bringing out low moans from his beloved. It was a wonderful ten minutes, maybe fifteen, Gary lost in the lust of finally fucking and unloading his balls into Cyn’s rectal depths.

It was only toward the end that he remembered to attempt a fingering of Cyn’s clit, reaching around to play with her marble, but his real focus was on his final arrival and the joy of flooding her rear with a hot viscous flood of his own making. To Gary it was wonderful, a Christmastime gift he would always remember. His joy was cut short when he pulled Cyn into a hug from behind, his cock softening but still held tight within the grasp of her anal sphincter, leaning in to kiss her cheek before noticing that Cyn had been crying, tears streaking down her face.

“Cyn, did it hurt? Did I hurt you? You should have told me. I’m so sorry.”

Gary wasn’t ready for her curt answer of “No. Stop it. You were fine. I’m not crying because it hurt. I liked it, really, so just stop apologizing. Just hold me, would you?” And she wouldn’t say anything more, her tears flowing down into the bedding and leaving Gary more perplexed than ever.

After a long shared shower and during their ride back to where he would drop her off a block from home, Gary tried to get Cyn to talk some more but she seemed quiet and distant. As she prepared to get out of his car, she leaned over and kissed him, a soft loving kiss, telling Gary not to worry, that she loved him and would see him again on Saturday.

Nice, but Gary couldn’t get over the feeling that Cyn’s telling him about her uncle had brought up some hidden feelings, some memories that Cyn wasn’t ready to face or didn’t want to discuss. Of course rather than badgering Cyn to let him in, he just turned to Penny to see if she could fill him in on any hidden details.

“Yeah, I knew about the uncle. She came clean about a year ago, maybe the last time they got together, but no way was I going to tell you that. She was pretty pissed that I told you about her mysterious neighbor, but I figured she’d have to let you in on the whole story eventually.” Penny was sitting in Gary’s computer chair, but with sweats that gave no hint to her feminine form. Which was fine. Gary was seriously focused on what was bothering Cyn and wanted Penny to tell him what was bugging Cyn so much.

Gary was certain that Cyn had told Penny more than she had let on to Gary. “She told me about her uncle, about his bed-ridden wife and having sex, or at least giving the old guy blow jobs until her father found out. And then, well, she kind of went silent and became real moody, crying and everything. What goes? Does she still have a thing for him?”

Penny smiled, a large devilish smile, and leaned in, saying “She told you about her uncle. But then what did you do? Anything special? Come on, Gary. Spill it.”

Blushing and hardly able to get the words out, Gary said “Um, yeah. For the first time, she let me, you know...” and Penny jumped in with the answer: “Butt fucked her. Gave that round ass of hers a cream pie. Come on, admit it.”

Gary was shocked that Penny seemed to so quickly guess his secret, and after putting up with a few seconds of her low chuckling laughter he realized that he was being played. “You already knew, didn’t you? What do you two do all day? Just text and talk about what your boyfriends do in bed? Not fair Penny, so knock it off and get to the point. What’s bugging Cyn?”

“Sorry,” said Penny, not acting at all apologetic. “Nothing more I can say. I mean, it’s up to Cyn, right? She must really trust you to tell you about the whole uncle thing. I can say that they became really close and it seems pretty weird that they’d do nothing more than tongue each other off for so many years. Right? Think about it. I can’t really say any more, but it’s also pretty interesting that just after telling you about her uncle, she asks you to ream her rear and then goes into some deep emotional dive.”

“You mean her uncle did that to her? And was she crying because he raped her? What’s up Penny? You’re just playing games here.” Gary was torn, confused, and he was above all upset that Penny wasn’t telling him what he was sure she knew about Cyn’s past.

“No games here Gary. Let’s be clear,” and here Penny leaned in and looked him straight in the eye and lowered her voice to just above a whisper. “No rape, at least not that I can tell. Cyn has only nice things to say about her uncle, but of course I used to only have nice things to say about Simon, so maybe that doesn’t mean much. And as far as all the different kinds of sex they engaged in over all those years, I’m not sure of that either. Maybe these are the kinds of secrets that come out only after you’re married, or maybe you’ll never know. But don’t sweat it. I can tell you that he’s in her past and that right now you’re her main man, so don’t screw it up.”

Gary found himself shaking, both body and mind stressed with all that he had learned about Cyn, though the questions continued to outnumber the answers. He wanted to ask more but was unsure of what to say, unmentionable visions still swirling around in his head when Penny broke in on his thoughts. “So maybe you should stop thinking about the long ago uncle and start thinking about the right now. You guys are going to move in together starting the first of the year, right?”

This brought Gary back to earth, but all he could mumble is, “Uh, yeah.”

“So, there’s bunches of stuff that you should be preparing for, as a new family,” Penny said. “Focus on that. And by the way, you’re engaged, right? Or at least you think you’re engaged. Would you call her your fiancé?”

Penny was keeping to her serious voice, low and focused and Gary automatically answered with an affirmative. “Of course we’re engaged. It sounds pretty weird to call her my fiancé, but I guess so.”

Penny leaned in even closer to Gary, enunciating each word as she said “Then maybe you should think about giving her a ring, dumbass. Unless of course you think you can find someone hotter and more fuckable in your next college class.”

The realization hit Gary like a hard right drive to his temple. “Oh shit, I forgot.”

“Yeah, but nobody else has,” Penny continued. “Cyn hasn’t wanted to nag you, and mom has noticed that Cyn isn’t wearing any kind of ring or anything as Cyn comes walking out of your room and she’s hoping your thought of marriage is just talk. So, I’d suggest you pull your shit for brains together and stop obsessing about the uncle and start focusing on things that really matter.”

Then Penny visibly softened, looked down at the floor, then up at a visibly shaken Gary and with obvious feeling and empathy said “Be nice to her Gary. Maybe take Cyn out on a date that doesn’t end with you screwing some part of her body. Right? You might think she’s a real tough woman who’s seen it all, but she’s still just a girl who wants to be loved, and you’re really lucky that you’re the man she thinks is up for the job.”

That’s when Penny stood up and started for his bedroom door, then turning and saying “Of course, mom has also mentioned to nobody in particular that she has a ton of leftover jewelry given to her by her grandmother, including some nice rings. So unless you want me to inherit the entire hoard, maybe you should ask her for a little help. Moms usually love getting mixed up in this kind of stuff.” And with that she left, leaving Gary with his jaw lowered and his mind still unable to decide what to do next.

The weeks began to tick by, Christmas arriving far more quickly than Gary wanted, then passing by and allowing the New Year and his new life to come slamming into his face with hardly any preparation on his part. Thankfully Penny’s suggestion had been a good one. Though his mother was less than enthusiastic about the possibility of gaining a daughter-in-law, she saw it as her motherly duty to keep Gary from making a complete fool of himself.

She had a number of very nice rings in the back of her jewelry box, one in particular catching Gary’s eye. It had a single small diamond in the center and three somewhat smaller rubies down each side, all within a tasteful gold setting. His mother had no attachment to it, didn’t even know who else had worn it, and agreed that any girl would be lucky to have him offer it up as a promise to love and cherish.

But when? He asked Penny, but she stepped back, saying that it had to be a surprise and that she was bad at keeping secrets, especially from Cyn. He didn’t want the ring to be thrown in with all of Cyn’s Christmas presents, and waiting for New Years seemed pointless and not that romantic, so he thought up something special of his own.

Two days before Christmas he arranged for a friend to hang out on a corner in a part of town known for it’s Christmas lights. Gary arranged for Cyn to join him and Penny that cold but clear night, walking the sidewalks and enjoying the light shows of the many garishly decorated houses, seeming to accidentally come upon his friend playing Christmas tunes on his guitar. Prearranged by Penny, a couple of other school friends wandered over, and as the soft chords of Silent Night filled the air, Gary got down on one knee and offered the ring and the rest of his life. Other passersby gasped and cheered with Penny and the rest as Cyn burst into tears and said yes. The only thing that could have made it more perfect is having it begin to snow, but nobody seemed to mind.

The story could end there, with Gary and Cyn moving in with one another, working and taking college classes and preparing for a shared life of bliss. Right. There were lots of bumps in the road, from being able to afford breakfast to learning how to use a public laundromat, but that’s just the kind of stuff young couples in love are supposed to learn while growing into adulthood. No, those many bumps and bruises were fine and sort of expected. The real problem was Penny.

Though Cyn had taken up more and more of Gary’s time and thoughts, and rightfully so, the previous couple of months had not been without awareness of the ongoing drama that Penny was a part of. The men in her life seemed to be doing her more harm than good. Gary had to include himself in the small exclusive group. After her visit in late October and once in November she had stopped dropping by his room at night, but she saw to it that her computer camera was pointed in just the right direction when playing with the occasional zucchini she had just liberated from the kitchen.

Penny had been perfectly aware that Gary continued to watch her via her computer camera and Gary never let on that he had another spy eye pointed directly at her bed. Even with Cyn within reach, Gary couldn’t escape from his obsession with viewing Penny’s bedroom antics, Gary certain that she had him in mind as she played with herself before the camera. Penny must have planned the time she and Cyn had performed for him, and she didn’t even try to hide her sessions with Keith from his roving eye. She was cruel, but Gary knew it was his fault for watching.

Keith was also a problem, not so much in what he did as in what he took for granted. Penny continued to see Keith as her boyfriend, her man, but he continued to act as though the relationship was at best a part-time hobby. Sometimes he would come by two or three times in a single week, Penny also spending countless hours on the phone with him (usually through texting). Other weeks he would disappear, sending Penny into despair, Cyn reporting back that Keith never seemed to give details out about his whereabouts other than to say that he was working.

Gary had only met and talked at length with Keith twice, once while Keith was hanging out with Penny in front of their house and once while Keith was waiting to pick Penny up from school. He seemed grounded and nice enough, but also without imagination, someone Gary could see doing nothing more with his life other than drink beer and watch ball games through every weekend of every year. But Penny wanted him and so Gary gave her his full support. Now if only Keith would step up and play his part.

The bigger problem, of course, was Simon. For all of Penny’s embarrassment and despair at what Simon had her do at the so-called Halloween party, she continued to see him on what seemed to be a regular basis all through November and into December. Penny didn’t say anything to Gary about him but did occasionally report to Cyn. Simon’s needs continued to grow, Cyn being very aware of the days Penny never made it as far as school. Twice Penny had talked Cyn into calling her mother and asking Penny to spend the night, each time Penny spending the entire weekend with Simon and, according to Cyn, a couple of his friends. This made Gary grind his teeth, but it got worse.

In early December he had come home late from work, expecting to spend a few hours on the computer writing out a paper for one of his classes, but he of course had to check on what Penny was doing in the privacy of her room. For all his love of Cyn, Gary still lusted after the shimmering thin slit that ran between his sister’s legs. He may have been able to resist sneaking into her bedroom every night, but he still felt it acceptable to watch her do other things to herself in front of the camera. He was expecting another quiet night, maybe Penny bending over to show off her ass to the computer lens, perhaps a long slow fuck up her ass with a dildo or giving Keith some head, but Gary found himself watching much more than that.

It wasn’t quite like the Jason and Keith event of many months before The video showed that a little after noon on that same day (a school day) Penny walked into her room with three men following, all crowding in, all surrounding Penny as she began to undress. The men often got in the way of the computer camera, but Gary’s web cam on the shelf caught all of the action. One of the men was easily recognizable as Simon, the other two obviously friends invited along for the ride. Simon and friends had Penny drop her top but told her to leave her skirt on, one friend getting on the bed and pulling her mouth over to suck his cock while Simon pulled her ass over the edge of the bed, ripped her panties down the middle, and pushed his cock into her waiting crack.

Simon didn’t waste any time, being the first of the three to pound his cock into Penny’s open legs and relieve himself inside of her within five minutes. After a minute Simon pulled her mouth off of the cock she had been giving head to, turned her over onto her back and crawled up on the bed to straddle her face. As she sucked on Simon’s somewhat softer cum-covered dick, the third guy pulled her ass up and started in on her, arms under her knees as he began working his cock through Penny’s hole.

This is when a great wave of nausea rolled over Gary. He turned away from the video, then shut his entire system down by ripping the plugs out from the wall socket. Gary was aware of how turned on he was, of how hard he had gotten watching the men take Penny on, but then came the nausea and all he could feel was shame. More than anything he wanted to change Penny’s life, to apologize for ever walking into her room, for invading her privacy, and most of all for not being the supportive brother he should have been. His mind was also confused, wanting to help Penny but unsure of just what she wanted. Gary didn’t want to come off as some righteous fool, telling her how to be a better person and turn away from Simon when Gary himself had unloaded his balls into her just a month before. He didn’t know what to do, but he knew he couldn’t stomach watching Penny act out her life on video anymore. If nothing else, Gary knew it was time to take down his private peep hole.