Growing Up - Cover

Growing Up

Copyright© 2009 by Openbook

Chapter 5

Drama Sex Story: Chapter 5 - A My Brother's Keeper Story. Jimmy finds himself once again negotiating from a position of strength. At least, that's what he believes.

Caution: This Drama Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Consensual   Reluctant   BiSexual  

We walked back to where our stateroom was. I was feeling very good, because I'd finally summoned up the nerve to tell Tina how I felt about her. I'd certainly meant it when I'd asked her to marry me, but that hadn't been part of what I'd planned to say to her. It somehow just escaped my lips before I'd had an opportunity to restrain my sudden impulse to ask her to marry me. Impulse or not though, I was pleased with her acceptance of both my declaration of love, and the proposal. By the time we got to the room, I had my dazed smile back under control.

"Sherry, guess what? He said it! He told me he loves me. See, I told you he would. Now you can ask him what you promised you would."

Tina and her sister embraced as they shared and celebrated Tina's excitement, and our obvious happiness at being there with each other. After her mind finally got around to the part about her now having to ask her question though, I noticed the smile abruptly leaving Sherry's face. My concern that Tina was exerting too much pressure on her sister, once again surfaced.

"Jimmy, please don't make me go through with this. Make her stop, please."

"Tina, maybe you shouldn't force her to do something she obviously wouldn't be doing willingly? This should be a happy time, for all of us."

Tina no longer looked happy. Her smiles, and all the joy she'd been exhibiting just seconds before were suddenly gone from her countenance.

"Sherry, you promised me you would, so go ahead and ask him." Tina was using her firmest tone with her sister. It was a tone of voice that I'd come to recognize during those times when she was pushing her sister to do something she was very reluctant to do, without first having some strong outside pressure being exerted.

I wasn't happy seeing it used for something I was apparently deeply involved with. What kind of question is this, that Tina's pulling out all the stops for? All I could tell from her tone of voice was that she was willing to brook no nonsense, or to tolerate any failure to comply from her sister.

Sherry moved away from her sister, distancing herself in the only way she could. She was now upset to the point where tears came streaming from her eyes. She looked over at me, in a silent appeal for my help. I'd often been whipsawed just like that between Danny and Kaitlyn, back when I was just a young kid.

Both used me all the time to try to bolster their side of whatever argument they were then having. I'd hated it back then, and I hated it even more now. Back then, I'd always steadfastly refused to take sides, even when it was patently obvious that one or the other was right. This was my first conclusion about what I should be doing with these two now. Only the fact that I'd just finishing asking Tina to share the rest of our lives together served to prevent me from doing what my natural instincts told me was the only correct thing to do.

"Sherry, if you promised you'd do something, then you should keep that promise." Even as I said those words, I felt like I was betraying something important to me. I wasn't exactly sure what, but I knew it was something.

As soon as she heard me side with her sister, Sherry abandoned all her resistance to asking her question. It was sudden, but it was also in keeping with her prior reactions in similar types of situations.

"Tina and I have some money in two trusts set up by Grandma Kerry, our mom's mother who died when we were very young, maybe seven or eight, I don't remember exactly when. Anyway, in the papers she signed creating the trusts, she named her bank as the trustee of the money until we turned eighteen. When we turned eighteen, we had some say so in how the money got managed, including the right to appoint a new trustee, or to split up the trust fund and have different people or banks manage the funds for us. When we turned eighteen, I signed papers to make my father trustee of all my money, but Tina kept all hers with the bank people that our grandmother had originally appointed. Tina wants me to ask you if you'll take over as the trustee of my trust fund?"

"Sorry, but I know nothing about managing other people's money. If you aren't happy with what your father has done, you should hire a professional money management company, or at least the trust department of a big bank. That's what they specialize in doing. Let the experts take care of it for you."

"He won't even give her any statements on how her money is doing. No one but him even knows how much is left of her money. I get my statements at the end of every quarter from the bank. What I'm really worried about is that he's going to pull something on her birthday, come up with some reason why he doesn't have to turn her money back over to her. I wouldn't put it past him to try to get her declared incompetent, just so he could keep her money for himself. You could stop him, if you took the appointment before he tries to do anything like that."

"It still doesn't address the fact that I don't have any experience with that type of investing. You might not like or even trust your father, but I'm sure he's better with handling investment money than I'd be. How much money are we talking about?"

"It was fourteen million for each of us when she died. Right now, the bank says mine is worth almost forty million. We'll get it from our trust on our twenty fifth birthday, in less than six months. My not letting him take over my trust money is what we fought about, and the reason they kicked me out of their house. He browbeat Sherry into signing his papers for her trust, but none of his strong arm tactics worked with me. I didn't want him to use up my money like he used up our mother's."

Fourteen million was a lot of money, not to mention the other bombshell Tina had just dropped, about what she was soon to be worth. She was a rich heiress, there was no other way to describe it. If I'd thought she was way out of my league before, now it was even more manifestly the case. Had I known about this before I proposed, I never would have done it.

"She can go to your bank and sign the papers reappointing them as her trustees. They'd know what to do to force your father into complying with Sherry's wishes."

"She trusts you, Jimmy, not some impersonal bank, filled with people she doesn't even know."

"You know them, or at least you trust them, and it sounds like they've done a damn good job with growing your assets. Forty million dollars, now I know what you meant when you said your starving artist days were nearly over. Don't you think you might have at least mentioned all of this to me before?"

"I had to be sure you loved me first. Sherry feels the same way. If you loved me, she said she'd ask you to help her. I told her you would tell me you loved me sometime on this trip, and she promised she'd ask you if you did."

I was still trying to wrap my head around the kind of money we were talking about here. I already knew this was far beyond my very limited abilities. The only thing that prevented me from outright refusing to get involved was my deeply ingrained sense of responsibility towards my family. Having just accepted my marriage proposal, that made Tina part of my family. By extension, this also applied to Sherry. I couldn't just refuse them both and walk away. It didn't work like that. I had sensed before, as far back as that trip we took to New York, that the two of them were conspiring in some way to set me up for something.

"How long have the two of you been planning on trying to get me to do this?" As soon as the two of them looked at each other, I knew I'd struck pay dirt with that question. They both looked guilty, and surprised at having been found out so easily.

"We weren't exactly planning, but we've discussed this since back when Sherry got kicked out, for setting the house on fire. Until they treated her like they had me, Sherry never believed me when I told her she couldn't trust either of them. After that, she did believe me. Jimmy, we both need you to do this for us. We don't want to try any legal maneuvers, we just want to get Sherry's money back from him, and get an accounting for how he managed it over all those years. We're both worried about what we'll find when we finally do get him to say what he did with her money."

"I'll help you look into it, but that's all I'm willing to promise you. I'm pretty sure he's legally required to give the trust beneficiary some reports about how the trust is performing. I can go to an attorney and find out more, without bringing either of your names into it. After I find out what he has to do, then we'll decide what needs doing next."

Surprisingly, to me at least, that seemed to satisfy the two of them. We went to bed right after that, with Sherry being used by both of us, in ways I now knew she received the greatest pleasure from. We were up late, in spite of the fact that we'd be disembarking early the following morning.

We had scheduled a one day layover on Oahu, mainly to give us time to decompress from being in vacation mode. I had booked us into a nice resort hotel, close to the beach, and we proceeded to continue to celebrate our engagement.

Tina had told Sherry that we were getting married, right after we'd concluded our trust fund discussion. That had been the catalyst for our over exuberant late night celebrating the evening before, on the boat. Our celebration at the hotel was a more traditional one, featuring a champagne filled dinner, one that later included even more champagne and plenty of dancing in the Tiki Lounge, inside our hotel. It was fortunate that our hotel accommodated late check out's, and that our flight back to the mainland didn't depart until five o'clock in the afternoon, Hawaii time.


I had mixed feelings, and was more than a little bit worried, on the flight back to Los Angeles. This was mainly due to my being nervous at the prospect of taking both Tina and Sherry up to Hesperia to meet my family. I'd known, at least since the time I'd first admitted my love for Tina to myself, that this was something I'd eventually need to do. Whatever else my brother and his family might be, they were my only family, and in my own way, I loved them and needed to show them my own new love.

Calling Danny and Kaitlyn a little rough around the edges wouldn't do them complete justice. I had no idea how Tina or even Sherry would react to meeting them, or to finding out the kind of people they were. One thing I was pretty sure of, was that both Danny and Kaitlyn would see absolutely no need to put on any airs, or to pretend any greater refinement than they naturally possessed. I knew that the sisters would get quite an earful if Danny and Kaitlyn got near to anything alcoholic to drink. I'd had years of experience with watching the two of them interact together, once they'd been drinking.

I rented a really nice luxury sedan at the LA airport. I wanted the three of us to be comfortable on the drive up the pass to see my family. We arrived at the trailer park a little before eight in the morning. We were all tired, still a bit out of sorts, and more than a tad irritated from the long flight and our lack of rest after our late night partying at the hotel. If I'd thought about it, I'd have stopped somewhere and given the three of us another day to recover from our recent overindulgence's.

Everyone inside the trailer was fast asleep when we arrived. After my knock, I could hear a wild flurry of activity inside. I heard Kaitlyn yelling for Danny to get up, and for him to go outside to give her a chance to straighten things out inside so their home was ready to receive guests.

"No guests here, Kaitlyn, just me, my fiance and her sister. All family. Open this damn door, I need to take a whizz." I felt like I wanted to set the tone for our visit. I didn't want my family to feel uncomfortable about how they lived, or to think that Tina and Sherry were there to pass judgment on them. I'd finally decided that they were my family, warts and all, and that I would no longer subject either them or myself to my hypersensitivity, or to the critical part of my nature that heretofore had been controlling most of my fears.

The door finally opened for us, about five minutes after I'd called out for them to let me in to pee. Danny had opened it, telling me with a big grin on his face that 'Katie needed to go put some clothes on, she'll be out in a minute'. I shouldn't have been concerned that Danny would try to be anything but who he actually was. As I made the introductions of Danny and the girls, I noticed he stood up a little straighter and pushed out his chest and sucked in the little gut he'd grown back after his back injury curtailed a lot of the physical exercise he'd been used to getting.

Danny had always been a good looking man. If he hadn't been, I'm sure his life would have been much harder. He was still good looking, even with that little touch of gray hair at his temples. When he smiled, I noticed he'd lost yet another tooth. I made a mental note to talk to him about going to see a good dentist. With a better smile, I was sure he'd be able to talk countless housewives into letting him re screen their entire supply of window screens.

Kaitlyn finally made her appearance, obviously freshly scrubbed and with full make up and carefully brushed hair. She still looked good when she bothered to get all spiffed up. In her youth, she had looked great, spiffed up or not. Time was catching up to her, but I'd still have to admit she looked good for her age. Looking at her, I took a little trip down memory lane, remembering some of the times we'd had, and some of the most lurid things she'd done to get me to give my money to her.

While I'd always felt some guilt about doing that with my brother's wife, I'd never had any question at all about whether or not she was worth all that guilt. Even a lackluster fuck from Kaitlyn was better than most of my other sexual experiences. Delilah, Tina, Sherry, and Leslie excluded, she was the best. Leslie only because I'd actually loved her. As I thought that, it came to me that I'd loved Kaitlyn too. In my own way, but still, for all that, a love that was kept somewhat masked by my distrust and unhappiness with her over the way she'd treated both my brother and me at different times.

As much as anyone else, Kaitlyn had acted as a surrogate parent for me in those first two or three years after my own parents died. It was me that first instigated a sexual relationship with her, blackmailing her into allowing it. Later, we were both to blame for what happened between us. I took another moment to look at her, hoping that she could see, from my face, exactly what I was feeling for her at that moment.

It was hilarious what happened later, after all the introductions were made, and the kids were gotten up and rushed off to school. The five of us sat around the big dining table, the nice one that once was mine, drinking beer and white wine, laughing, with Danny, Kaitlyn and I alternating as we told stories about things we'd done and scrapes we'd all gotten out of. Kaitlyn didn't spare herself when she told her stories. Danny tried, but Kaitlyn and I both corrected the "spin" he tried to put on things to make himself seem like a victim rather than an active and willing participant in his various woes.

This too was a kind of therapy. All of us laughing and vying with each other to bring up episodes that once caused us massive worry and grief, but which now, with the passage of time, seemed no more than amusing anecdotes to explain our family's strange history to both Tina and Sherry.

Tina and Sherry both, unused to either heavy consumption, or morning liquor after being up for most of the previous two nights, got themselves lit up like Christmas trees. They were soon in bad enough shape as to be unable to keep from staggering around while getting up to get refills of their Chablis. While they sat and kept sipping, they were also laughing themselves hoarse at all the stories the three of us were telling on ourselves.

We were all surprised when the three kids announced their arrival back home from their day at school. None of the adults were in any shape to either do any cooking, or to go out anywhere, so we ordered up some delivery pizza and sent the children outside to play until it got there. Tina, Sherry, and I wound up sleeping on the sofa that was also a pull out bed.

The next morning was punctuated by voices on edge, and periods of quiet desperation, as Kaitlyn tried to marshal up the necessary resources to make cereal for her children, and to then get the kids off to school. After they left for school, all of us went back to sleep for a couple hours. I woke up hearing Danny and Kaitlyn's loud noises as the two of them celebrated yet another hectic consummation of their marital rights. I looked over at both Tina and Sherry, discovering that they too had awakened hearing the mating sounds.

"Wow, Katie sure makes a lot of noise, doesn't she?" Tina whispered loud enough that both Sherry and I could hear.

"No need to whisper, they don't care who hears him. I don't know what Danny has that I don't, but she never carried on like that with me when I used to do her."

Sherry's eyes got as big as saucers when she heard me admitting to having fucked Kaitlyn. From my age and Kaitlyn's, she knew it had to have been after she was already married to Danny that it must have happened.

"You and Katie? How could you do that?"

"I know. I've asked myself that same question after just about every time with her. After I asked myself that though, my next question was always 'what has Danny got that I don't'?"

Kaitlyn's voice came yelling out from behind the sliding door panel of their bedroom.

"He always really means it when he fucks me, and that's something a woman can always tell, and that she appreciates. He never holds anything back either, like you always did. You better have learned to mean it with those two girls you have out there, because, if you don't, they'll go right out and find someone else who does."

I heard Danny's full throated laughter, but this was soon drowned out by more noisy lovemaking sounds from them both.

"Ignore them, they're just trying to show off."

"I've got news for you, Jimmy. If that's what they're doing, it's working. Why don't you see if we can start making our own noises? With three of us, we should be able to drown their noise out."

We had to force ourselves on, Sherry. She put up quite a struggle while I held her down and Tina pulled down her jammy bottoms. She ceased fighting us, just as quickly as Tina's tongue began parting the lips of Sherry's pussy. I continued holding her down though, not because I thought she was resisting, but because I knew my doing it would intensify the force of her explosion when it finally came. After her first, very loud cum, I rolled her over onto her hands and knee's and took her doggy style while Tina and I got her moved into position so she could do for Tina what she had just gotten done to her.

I was vaguely aware that the three of us had an audience. When I turned to look down the trailer's hallway, sure enough, there were Danny and Kaitlyn standing there. They were both naked, and showing signs of their recent activity. Danny had his arm around Kaitlyn's shoulder, and the two of them were just standing there with big smiles on their faces, watching proudly as I poured the coals to Sherry's back thrusting pussy while she ate out Tina. Tina saw them watching us too, and I could see it intensify everything for her to be watched like that. I wanted Sherry to benefit from knowing she was being watched, so I called out to Danny and Kaitlyn, asking them if they'd please make us all some coffee.

Hearing me, Sherry lifted her head and looked down the hallway. Even her back turned bright pink with her embarrassment at seeing that she was being watched in such a compromising position. Back down went her face, straight into Tina's muff, and she started pushing her ass back at me with twice her previous vigor. In fifteen more seconds, we all heard her screaming out her orgasm, right into Tina's very happy pussy. The pussy muted the noise, but we all knew she was having a big one.

For the next hour, as all five of us sat at the table, naked, and drinking our coffee, Sherry experienced a kind of humiliated joy that had her practically vibrating in her extreme excitement over being the primary subject of our discussion.

"She's really cute, Jim. Hell, they both are. What's it like, fucking 'em both like that at the same time? You ever forget which is which? Naw, I guess you can always tell 'em apart just from their hair being so different. If it wasn't for that, how could you tell 'em apart?"

"Well, it would be hard, but I could do it. For one thing, even thought their pussy juices taste the same, Sherry is a big squirter. Tina doesn't squirt, and when she comes, her pussy squeezes down a lot differently than Sherry's does. When Sherry gets one of her big ones, you can't move your cock at all. She has it in this vise in her pussy, and even if you were just starting to cum yourself, she squeezes so tight, you can't."

"Bull shit, Jim. If that was even possible, I'd have run into it before now."

"I'm telling you, Bro, it's the truth."

"She can't. Nobody could make it so tight with her muscles that I couldn't keep plowing her, not with how hard my cock gets when I'm shooting."

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