Upheaval: Ch. 03

Kelly may be a sound sleeper according to Skylar, but she was an early riser. When I woke up, she already had her coffee and was sitting at the kitchen table. When she saw me, she looked up, a serious look but not an angry look, more tired than anything.

"Good morning. I guess I overdid it a little," she said. "You sure had a good time."

Did she mean what I think she meant? Was she really that nonchalant about what she saw, if she saw it? I was so confused. If she meant what I thought, why didn't she say "you and Skylar"?

"We all did," I said eventually. Kelly just looked at me, kind of searching. Maybe we both had our suspicions but weren't really sure if the other knew what the other was talking about. I decided to change the subject, sort of. I was still searching for some indication that something was different between Kelly and Skylar.

"You and Sky had fun in the water yesterday. It's really nice to see you both so close, closer than I've ever seen you two." Again, my comment was met with a probing look, I felt like she was trying to read my mind.

"Yeah, I guess she's grown up a bit." Her answers were short, although a little uncomfortable, I didn't sense any anger or anything.

After a cup of coffee and some toast, I was ready for my run. Skylar wasn't up yet so I figured I was on my own. Just as I left the house and started to run Kelly called after me, "Wait."

I stopped, "Sky's up. She wants to go but needs a minute."

"Ok," I said and waited. Once Skylar came out, we started the run.

"You know what I really want," she asked as we began. Nothing like jumping right into it.

"No, what?"

"I want to give you your fantasy, but I don't know how to make it happen, it's a hard one."

"What makes it so hard, I'm sure you have friends who are just as into sex as you."

"You don't want a friend, you want me and my mom."

As was becoming a habit on our runs, one of us stopped suddenly. How the hell did she know that. I never said it, I don't think I ever did anything that would indicate that.

"What? What makes you say that?"

"It's obvious. I see the way you watch us. I see that you're hard when we're together."

I felt like I had to be careful here, yes, that's what I wanted but could I just come out and say, "sure, I'd love to fuck you and your mom?" I decided to take a different tack. "Is that something you want?"

We were running again. "I didn't think so, at first, but doing what I did with you made me, I don't know, want to do things that were, if not wrong," she hesitated, "well, ok, wrong."

"But... you could, don't get me wrong, I'd be into it, but, you could have sex with your mother?"

"I don't know what the hell I started by sucking your cock, but yeah, if it turns you on, it turns me on and... I don't know. I think, I'm pretty sure, my mom would be into it. I just don't know where to go from here."

There were so many questions, so many twists and turns, so many paths to follow.

"Sky, let me ask you, why aren't the boys here this week?"

"Because they're staying with friends."

"I know that," I said, frustrated. "But was it planned? Did you guys want to be alone with me?"

"No," she said, "it was totally coincidental."

"Did you leave my bedroom door open on purpose last night?"

"No. But I didn't mind it was open." That leads to many more questions but I have to get the first set of questions done first.

"Did your mother see us last night?"

"She didn't say anything to me but... I kind of think she did." Why didn't Skylar seem as concerned as me or as confused?

"Skylar, if she saw us, how could she not say anything? To any of us?" I was beginning to spiral out of control and wanted to just go back to the way things were. The fantasy was one thing, but navigating the intricacies of making it real, was a level I wasn't sure I could handle.

"You know, maybe my mom planned for Mike and Cameron not to be here. Maybe she knew something was up and wanted..." I cut her off.

"All this speculation isn't helping us."

We were on autopilot and, at this point were approaching the house, not even noticing we had turned around. "This either ends or progresses tonight," I said. "Here's what we're going to do." Skylar and I came up with a plan. At dinner, we'd start the process.

"Let's play a game tonight," Skylar said as we ate dinner on the deck. Sunset would be soon and the bugs would be too much, so as soon as dinner was over, we'd be chased inside.

"What game," Kelly asked.

"I don't know, I'll just pick whatever I see first." I had a cabinet full of games in the living room. After we got all the dishes into the house, I sent Kelly and Skylar to set up the game as I loaded the dishwasher. None of us really wanted to drink tonight, last night was enough. Although I felt on edge all day, things were starting to feel normal again. Of course, as Skylar and I implemented our plan awkwardness or worse was sure to come back strong.

"I'll just reach in and pick something," Skylar said, not looking into the cabinet. She pulled out Monopoly and Kelly groaned.

"Oh, that's boring," she said.

"When we were kids, it was, but now we know how to play. Plus, I read about cool changes, like, one person is designated as 'rich' and starts with more money but can't buy any property until they've been around the board once."

"Ok," Kelly said, not exactly sure that change alone would be enough. I was growing nervous in the kitchen, waiting for my cue to come out.

Skylar took the lid off the game, took the board out and placed it on the table. Kelly started gathering the game pieces, dice, and cards. Skylar turned back and said, "Wait, where's the money?" That was my cue.

I came out of the kitchen. "What's up?"

"Your Monopoly doesn't have any money," she said.

"Ooohhh, well, uhhh, that's not Monopoly, that's Sexopoly. You don't use money. I, uh..." I hesitated for affect, "I got that to try to get Amy, well, you know." There was silence, but Skylar didn't want Kelly to say anything so she started.

"I'm game, if you guys are."

"I don't think so," Kelly said, "maybe that's a game for just you two." There it was, an admission, she knew. How much she knew, we had no idea, but she knew something.

"What do you mean, mom? Why? Why not all of us?"

"You're an adult Sky, you can do what you want. I know how you are, you tell me everything. If you want to play around with Uncle Drew, that's your business."

Skylar walked over to Kelly who was sitting at the table, she sat in her lap and hugged her, "I'm sorry mom, it was me, don't blame Uncle Drew, you know how I get, I'm sorry." Skylar then did something I hadn't expected, she kissed her mother on the lips, slowly and deliberately. Not a full-on romantic kiss but also not, not romantic, if that makes any sense.

"Mom, you always like hearing my stories, you always ask for details, maybe now it's time you live one for yourself?"

"Yeah, I like living through you, but I don't know about with you." Again, out of nowhere, another kiss. I was so turned on but too scared to say anything myself.

Kelly looked at me, really stared at me, then said, "Loneliness, sucks, huh?" I just nodded.

"Mom?" Skylar asked, "why are Mike and Cam at their friends? Did you do that on purpose?"

Kelly let out a long sigh. "I just wanted some adult time."

"It's not like they're little, mom, they're pretty self-sufficient. Was there maybe another reason?"

"I don't know. I don't want to talk about this anymore. If you want to play the game let's play." Kelly didn't really sound defeated, there was a bit of hope and anticipation in her voice. Skylar kissed her again, this time I swore I saw some tongue.

It was finally my turn to speak. "If at any time any one of us wants to stop, then we stop, agreed?" They agreed. "You play just like Monopoly but you pay with your body, with actions. For example, if I own Baltic Ave. and you land on it, rent is a kiss, a simple little kiss, nothing romantic, that's for higher priced properties."

"What's the rent for Boardwalk," Skylar asked.

"Whoa, you just jump right in, as usual." That got a chuckle out of them and helped to break the ice a bit. "Wait and see. One more thing, when you buy a property, you buy all the properties in the color, so the game progresses much more quickly. Let's roll to see who goes first."

Kelly won the roll and was first to move. Of course, she rolled a seven and landed on Community Chest. "Those don't count yet," I said. "They're more intense so they don't count until everyone has gone around the board once."

"I don't know about this game," Kelly said.

"Come on mom, can I look at the card anyway Uncle Drew?"

"No!"

"Hold on," Kelly said. "I know we weren't planning on drinking but, can you make me an old fashioned, Drew?"

"Yeah, I'll make myself one too. How about you, Sky, want something?"

"Sure, I'll take a beer."

Once I was back with the drinks, Skylar rolled and got double fours. "I'll buy it." The price was to tongue kiss the person to your right, that person was Kelly. "Well mom, that's the price."

"Perfect timing on the drink," she said.

Skylar leaned in and their tongues met. They moved around each other a bit and then separated. I was on the verge of a breakdown. If I'm this turned on now what does the rest of the night hold? Seriously, I thought, what does the rest of the night hold?

Skylar rolled again, this time landing on St. James Place. "Oh, I'll buy that too."

"Better property costs more," I said. "This one is strip to your underwear."

"Ok," Skylar immediately started stripping.

The game progressed quickly as we all tried to buy up property, the best properties "costing" the most. Before long Skylar was naked, Kelly was in her underwear, and I, not having good luck with the dice, was still fully dressed. I paid some rent, so that was fun, but apparently, I sucked at Sexopoly. That was about to change drastically. I landed on Chance.

Kelly stopped me from taking the card. "Before that, I need another drink, I think we all do." In spite of the seriousness of and implication of the game, we were having fun. I saw Kelly checking Skylar out more than I would have imagined, I, of course was basically just staring at them both.

I made the drinks and came back to pick my card. "If clothed, you must remove all clothes" read the card.

"Well, here we go," I said. I was glad to get release but it was a really odd thing to just get naked then sit there continuing to play the game, my hard cock standing at attention, Kelly and Skylar seeing it, staring at it. The next roll of the dice would change everything.

It was Kelly's turn and she landed on Community Chest, the card read, Luxury Tax, give 15 seconds of oral to each player. Kelly looked at Skylar first, then me. It's one thing to give me oral, but her own daughter?

"Uhm, we make the rules, we don't have to..." before I could continue, Kelly stopped me.

"This is why we played isn't it, to give us an excuse for what we were about to do?" That was certainly true but I really didn't think of it that way.

"Uh, I guess, I guess we could blame the game," I said drawing laughs from Kelly and Skylar.

"I'll start with you Drew," Kelly said approaching me and dropping to her knees. I couldn't believe what was about to happen, Kelly, my long-time friend, someone who I always thought as much more conservative than me, was about to suck my cock in front of her naked daughter. How I was able to maintain composure was beyond me. When Kelly took my cock in her mouth, I let out a moan. "Oh God, Kelly, that's great."

My head was back and my eyes closed, it was only supposed to last 15 seconds, I had no idea if anyone was timing it, then I felt an odd sensation. I opened my eyes to mother and daughter, Skylar and Kelly, both sucking my cock, each running their lips up and down either side.

The thing I spent months hoping and dreaming would happen, was indeed, taking place in my lake house.

"I think the 15 seconds are up," I said, hoping for a respite.

"Actually mom, there was more to it, or did you forget?" Wow, I mean wow! Skylar wasn't going to let her mom off the hook that easily. She wanted Kelly's lips on her pussy and she wasn't going to let that opportunity slip.

Kelly was still on her knees in front of me, Skylar simply moved her chair so that her mom only had to rotate 180 degrees. Skylar had her legs spread, her pussy already dripping wet, having watched her mother suck my cock.

To my surprise there was no hesitation, Kelly dove into her daughter's pussy, the sound of slurping, sucking, and licking shocked me. I felt, like so many times over the past few days, like I was missing something, like there was an understanding, a connection, I was not privy to. I could find out details later, for now, I'd enjoy the show, enjoy the game, enjoy the night.

I watched as Kelly's tongue disappeared into her daughter's cunt. Skylar had a tit in each hand, squeezing and rubbing them as her mom continued to fuck her with her tongue. This was so out of character, really, for all of us, and yet, none of us were hesitating, none of us were asking to slow down, or stop.

Skylar was grinding her pussy into her mother's face, oohing and ahhing, as Kelly's tongue probed her daughter. For some reason I interrupted, "I think the 15 seconds are up," I said, for the second time.

Kelly stopped and slowly turned to me, a little upset I ended her fun. Dripping from her chin was Skylar's pussy juice. I couldn't help myself, I took Kelly's face in my hands and licked her daughter's cunt juice from her chin and kissed her, our tongues exploring each others mouth for the first time.

Kelly and I were two whiskey sours in, and Skylar similarly had a couple of beers. None of us were drunk, barely even buzzed, but we all agreed to another drink. Kelly and I switched to straight bourbon, and Skylar joined us.

It was time for the next person to roll the dice but none of us could remember who was next. Then, we realized, since Kelly had to do what she did, that it must be Skylar's turn. She landed on her own property so no rent was due.

I was next and ended up on Free Parking. Well, this was interesting.

In Sexopoly, Free Parking was really Free Use. I could do what I wanted with who I wanted, but there was a limit. I had 15 seconds. The choices were unlimited, but I chose to give oral sex to Kelly. She had already done so much and hadn't had any enjoyment herself.

I made clear my intentions and as I moved closer to Kelly, she spread her legs, and I pushed them closed. "What did you do that for," she asked?

"I'm in control," I said. I pulled her to the edge of the seat, lifted her knees up, and then spread her legs. Her ass and pussy fully open to me. "Wow," I said.

I leaned forward and planted my tongue firmly on her asshole. I hesitated a bit and Kelly let out the sweetest "ahhh" I ever heard, then I licked straight up her slit to her clit and beyond.

"What the..." Kelly said nothing more, but almost started hyperventilating. For the third time in... in... who knows how long has passed, but for the third time, I called 15 seconds had passed.

This is the problem with Sexopoly, it's hard to know who goes next. Once the fun begins the game isn't that important. Skylar was the one who ended the game once and for all.

"The game got us here but, mom, Uncle Drew has cum in my mouth twice, I'd really like to see him cum in your mouth now." Straight to the point, the apple didn't fall far from the tree.

Skylar was very serious, I was not. "Well, after those two seconds, what do we do next?"

Maybe it was the drinks, maybe my comment just wasn't that funny. No laughs, no giggles. Skylar looked at me and said, "whatever we want."

Kelly asked that I move to the couch, that way she wasn't kneeling on the floor. Like I had predicted, she started sucking my cock and within a few seconds I was shooting load after load into her mouth. Unlike her daughter, Kelly was not expecting that level of cum. It dribbled onto my cock and, to my shock, surprise, and excitement, Skylar took over, sucking up every last drop. I wanted to crawl into a cave and live out my life alone, completely satisfied, completely fulfilled. That was not to be.

Skylar led us to my bedroom. I practically passed out on the beg and Skylar said, "Mom and I have something planned for you. Lie back and relax."

Huh? Skylar and her mom had something planned for me? Who was planning what? Who was playing who. I didn't drink that much but I was drunk on whatever was happening. And what was happening was that Kelly and Skylar were in a 69-position licking, sucking, and fingering each other's pussies.

The excitement of the evening was too much for all of us and soon, mother and daughter were cumming. Kelly calling out Skylar's name, "Oh God, Skylar I'm cumming, oh, oh my God."

"Of fuck, mom, me too, holy shit, I'm cumming in my mother's mouth, oh my God this is so fucking hot." Hearing their screams and moans of pleasure, mother and daughter, lost in each other, was the most amazing, sensual, and erotic thing I've ever experienced.

Skylar crawled off her mother and laid down beside me. Kelly rolled over and I was the meat of a Kelly/Skylar sandwich. The three of us fell asleep and didn't wake up until 8 the next morning. The latest I'd slept in years.