Upheaval: Ch. 01

Three lives turned upside down in just one year. There were more affected, but these three, experienced a change none of them expected. One year. That's all it took. It was a time of upheaval in their lives and it brought about drastic changes.

The first year was tragic and painful, that set the wheels in motion, which led to the most unlikely series of events.

None of this will make sense if I just start at the big change, so maybe I have to start a little further back, like twenty-five years back.

I was newly dating Amy and she worked with Jim. Jim was married to Kelly. Amy was invited to a New Year's Eve party at Jim and Kelly's, and she brought me, her new boyfriend. My name is Drew.

Jim and Kelly had only been married a couple of years. High school sweethearts, they grew up in Ohio but moved to NY for work. Well, they moved for Jim's work. Kelly was highly employable but didn't have the salary growth potential Jim had. Jim was in tech.

From the moment Amy and I met Jim and Kelly, we were close.

Even when Jim's job took them overseas and he and Kelly moved to Germany, that wasn't enough to derail our friendship. They didn't stay too long, eighteen months, in all, and then it was right back where we left off.

I'll spare you the details, the vacations we spent together, their decision to have kids, the birth of their three kids. All of that is life, and life goes on.

Until it doesn't.

The four of us were quite comfortable in our roles, in our careers, if not necessarily in other areas of our lives. Amy and I were struggling. Not financially but personally. Jim and Kelly were struggling, not personally, but financially. Neither knew this about the other because no matter how close we were, we had secrets.

As life progressed, the four of us were quite content, then, while Amy and I were on vacation, we got the news that Jim had been killed in a motorcycle accident. Kelly, now alone to be the strength and support for her three kids. Skylar, who was just about to finish her sophomore year in college, Mike who was a Junior in high school, and Cameron, or Cam, who was going to be a high school freshman the next year.

Without hesitation we flew home to give the support and friendship Kelly needed.

A lot happened over the next year, the year that started with tragedy, ended in chaos, beautiful chaos.

I didn't take Jim's death well, and yes, I began drinking heavily, and while I take full responsibility for my actions, for my role in the problems Amy and I had, the truth is, they started much earlier.

I had a strong sex drive and Amy, most certainly, did not. My drinking didn't help. When Jim died it pushed me over the edge and drove Amy even further away. The one connection we had, the one shared purpose, was helping Kelly and her kids navigate the mine field they found themselves in.

Even after the painful divorce, Amy and I, separately, of course, remained close with Kelly and the kids.

Welcome to year two when, after the tragedy, after the pain caused by my drinking and Amy's coldness, chaos entered the equation.

At this point I feel like we'd entered the Twilight Zone meets a Quinten Taratino movie. It was almost like Amy and I, childless though we were, were granted visitation rights with Kelly and her kids. We'd see them but always separately.

What Kelly and I never shared when we were both attached, we now shared freely. I opened up about Amy and my sexual disconnection, she shared the financial trouble she and Jim had. Luckily, I could help her in that area, as I was in the financial field, but unfortunately Kelly could not assist with my problem, at least not that I knew.

One thing that always shocked me about Jim and Kelly were how openly they shared certain details about their oldest child, Skylar, about her dating life, about how kids their age saw things, about how they approached sex. I was shocked and it made me feel old and out of touch.

I finally brought it up one day while having a glass of wine at Kelly's house, the kids in school, and Skylar away at college.

"I guess I was born too early," I said.

"What do you mean," Kelly asked as she prepared some snacks to go with the wine.

"Well, kids today, like Skylar's age, are just more open, more accepting of different things. I sometimes wonder if I would have done better in this time, then when I came of age."

"Yeah," said Kelly, "I was always shocked but also interested. Jim, of course, didn't want to hear any of it. Head in the sand kind of thing."

"It always amazed me that she shared so much with you, I mean, you guys had a great relationship, unless you didn't."

"And when we didn't, we were at each other's throats." Kelly's demeanor changed at this point and she became much more serious. "I have to say that's changed since Jim has passed, we never fight, she's so caring, protective, and affectionate with me now."

"I'm so glad to hear that," I said, "you both deserve the best." There was one word, however, that didn't seem to fit. Caring and protective made sense, but affectionate? That word intrigued me, affectionate in what way? I could imagine, but I just chalked that thought up to my overactive and under stimulated libido and moved on.

While these events unfolded over a year, my story only hits the highlights, the pertinent information needed to convey the chaos.

It was spring break and Kelly, Skylar, and the boys were visiting me at my vacation home at the lake. I was an athlete in my youth as were all of Kelly's kids. Skylar decided to join me on a run the second day of their visit. I don't know why I brought this up, but during our run, I said, "Your mom, she's funny, sometimes she doesn't have a filter."

"Yeah," Skylar said, "she says what's on her mind, in front of anyone. There are no secrets with her."

"And yet you shared a lot of secrets with her."

Skylar stopped. By the time I realized it, I was maybe 25 yards away, and I stopped, turning to see what was up.

"Hmm." Skylar looked at me quizzically. "Oh, what did I share with her, you know, that she shared with you?"

I felt like I was a bear who had just run straight into a bear trap.

"Just, I don't... just... you know... stuff that you, well, you know." Without conveying any information in my non-response, she knew exactly what I was talking about.

"I know I went into detail, did she?"

If this had been a true crime movie, I'd be sitting in a cold room with a hot light shining at me and I'd be struggling just as I was then.

As I looked at her in her jog bra and tight shorts, a smile crept across my face. "It depends on how detailed you think detailed is. I'll say it was just enough detail to..." I trailed off.

"To what," she asked.

"To make me wonder." Wonder what, you might think is the next question, but she knew exactly what I was wondering.

"Uncle Drew," she began. She called me uncle, and Amy was aunt, since she could first speak even though we were not related. "Uncle drew," she continued, "You're older, more experienced, and that excites me and you know what else?" She didn't wait for a response, "you don't have to wonder."

Well, this conversation just took a 90-degree turn.

"Yeah well," I deflected, "the only thing I have to wonder about is how long a break is too long when I have training to do." I thought I handled that adeptly.

The next day, however, I learned just how much of a trap Skylar had set. We had all planned to take my couple of kayaks, rent a couple more, and all go out on the lake together. Skylar, however, suggested we just take turns. Kelly and the boys would go first then she and I would go. Once they pushed off and Skylar and I watched from the shore, she said, "My mom might have shared my stories, but she also shared yours. Kelly," she referred to her mother by her first name, "doesn't keep secrets."

She wasn't wrong.

"What kind of secrets?" I asked.

"Like how you and Amy struggled. I'd like to see if I could handle you, if I could, you know, take what she couldn't."

My man brain, not the one in my upper head, took over.

"I'm old as fuck, It's not whether you could handle me, but if I could last even a minute or two with you." At this time, I was 48 and Skylar was 20, so I wasn't exactly old as fuck, but still.

Wait. Where the hell did this conversation just go?

"Well, I'm willing to test the limits." Skylar moved closer to me, reached down and gently rubbed my crotch. "Let's see who comes first, you or them," she said, referring to the eventual return of Kelly and the boys.

I couldn't do anything but stare. Was she being serious? What exactly did "test the limits" mean? All the thoughts came rushing in. Was I betraying the trust of my departed friend, would I be thinking or doing this if he were alive? What about Kelly, wasn't I betraying her trust? Then the thought that I never imagined would ever be thought occurred to me. What about Kelly? Maybe I should be doing this with her instead.

Finally, Skylar broke the silence and snapped me out of my spiraling thoughts. "Come into the house, I'll suck your cock and you'll be the lookout. If you cum before they come back, I win, if you can hold out until they get back, then you win."

"No," I said, "that would definitely be a loss." She laughed as we went inside. The conversation seemed so natural and normal, in spite of the fact that what we were talking about was so abnormal, and, really, unnatural. Nothing about this was right but I, we, went along with it.

It definitely sounds like an excuse as I write these words, but I felt powerless. I felt like I shouldn't do this but wanted to so badly as, apparently, did Skylar. She was always a little immature, but since Jim's passing, she'd gotten much more serious, much more adult.

There I was facing a girl who could be my daughter and we were about to do something that I never would have guessed. There was no romance to it. She simply slid my bathing suit down, sat me on the couch and lowered her mouth onto my rock-solid cock. A wave of euphoria washed over me. I was shocked to see that she immediately took all 7 inches into her mouth without gagging or coughing.

Luckily, I was distracted as I scanned the lake for any sign of Kelly and the boy's return. I really wanted them to come back quickly. I wanted to "win" even though we never said what the winner got. My focus waned however as Skylar skillfully sucked my balls while gently stroking my cock. She was amazing. I was in awe.

Skylar was definitely like family to me. Although she called me Uncle Drew, I felt a more paternal connection with her since Jim had gone. That thought shocked me as Skylar once again took my cock into her mouth.

Without gagging or spitting she kept my rod perfectly lubricated and then she did something I'd never experienced before. I was watching her now as her head bobbed up and down on my shaft. Skylar laid her left hand flat with her thumb out forming an L shape. She placed the fleshy part between the thumb and pointer finger on the side of my cock. With her right hand in the same position, thumb at a 90-degree angle she placed it on the other side of my cock and placed the fingers of her right hand over the left.

What this did was give her control of pressure but using the fleshiest part of her hand. It was the closest simulation to a vagina that I'd ever experienced with hands and it was amazing.

"Holy shit, Skylar, that... that is wild." My breathing was noticeably heavier and I knew it wouldn't be long now.

"Oh fuck, you're gonna win, you're so gonna..." my words stopped dead in their tracks as I heard Kelly calling out my name. They were back and we were scrambling. I had won, but as I joked earlier, I had really lost. I quickly ran to the bathroom, pulling my bathing suit up, as Skylar wiped her mouth and went outside to make an excuse.

Once I was presentable, I went outside to go on my kayak excursion with Skylar, no one was even a bit suspicious. I was so close and now my balls were aching. As we got into the kayaks and began moving away from the shore, Skylar said, "Do you know someplace secluded? I really want to finish."

"Yeah," I said, "let's race." With that I started paddling as fast as I could. Skylar matched my effort easily, and after about 10 minutes, we beached the kayaks and dragged one into the woods a bit.

"Well, you won, so you decide how the rest of this goes."

"I'm not selfish but I... I... just... I..."

"I get it. You don't feel right doing anything to me. I understand. I'm going to take my top off though, you know, to help you." She took her top off revealing such round and firm breasts, slightly larger, and I imagined, perkier, than her mother's. I lowered my bathing suit and Skylar started in on me again.

I immediately felt the pressure building as she took all of me into her mouth. Then, I don't know what came over me or why I was asking this or what I thought it would lead to, but I asked, "have you ever had sex with other women?"

Without stopping she said, "mmmm hmmm" sending wonderful vibrations through my cock. Then I asked, did you like it? Again, "mmm hmmm" was her only response.

I think she could sense that I was getting very close now and she stopped, looked up at me, and asked, "why do you ask? Do you have something in mind?"

I did, but the thought going through my head would never, could never be spoken. Hiding the true fantasy, I simply said, "I always wanted two women at the same time, to give them pleasure, to receive their pleasure, to watch them pleasure each other."

"I'd like that too. Who knows, I mean, you won the bet." A sly grin crossed her lips and then she bent down and took my cock back into her mouth. With that thought, or more accurately, the evil thought I didn't share, clear in my mind, I came in Skylar's mouth. Wave after wave coursing through my body. Skylar did her best to swallow it all down but with how long it had been for me, some dripped from the side of her mouth and seeing that, I almost came again.

Once my breathing calmed and my erection subsided (which took longer than expected to Skylar's surprise and awe) we got back in the kayaks and made our way back to the house. Kelly had lunch waiting for us and we continued through the day as if nothing unusual had happened. All day, however, I looked differently at Kelly.

Yes, you read that correctly, I looked at Kelly in a much different light. In my fantasy the woman I would share Skylar with was her mother, Kelly. I was ashamed, guilty, and turned on at the same time. I was a mess.