Things got even better the next round. Becky had to play with her nipple for a minute (behind her bra, it was barely anything interesting), I had to admit that I had a crush on some girl at work (I wasn’t going to mention Sierra in that moment. I wasn’t that stupid), and Joey ended up standing on one leg and singing the Star-Spangled Banner (like I said, the game was weird).
But spectacular Sierra also lost her last piece of overwear, slipping her slim skirt down her long legs. She was wearing a pair of bright bikini briefs that matched her shining scarlet bra. Her panties kept everything covered, sadly, but seeing the shape of her thighs and butt was more than enough reward. I was suddenly very glad that Becky had guilted me into going to her parents’ house for Thanksgiving.
Becky refilled our drinks while we got used to our new state of mostly undressed. Eyes went everywhere, examining everyone in detail. The scotch was running low, but my wife came back with another bottle, this time gin, and made sure we were all well lubricated.
I would have gotten up to help my wife pour, but I was trapped at the table. I had an epic erection going, and my underwear might as well have been see-through. I noticed Becky’s brother wasn’t getting up either. We both were clearly suffering from the same affliction.
Worse, the chances of someone revealing something serious next were super high. I was trying to balance my hopes of seeing more Sierra skin with my own wish to stay covered (let alone the complex feelings I had around my wife or her brother getting naked) and I kept toppling over. Except, for the first time, the game didn’t cooperate. The purple squares began to peter out on the path. Instead, a new color came into play: orange.
Sierra had described these before as “riskier” dares and I hadn’t thought to ask what she meant. The greens had all been oddly tame (like Joey’s one-legged anthem). Thus, almost anything was more dangerous than what we’d been asked to do so far. But we found out very quickly what the oranges offered.
It was my wife’s turn and, sure enough, she landed on the first orange square. I noticed her hand was shaking slightly as she reached for the card. It might seem silly to be so worked up, but we kept waiting for the game to surprise us with something shocking. It had promised us dirty doings on the box, so we had to assume they were coming at some point, right?
Becky read the card. “Kiss the person of the opposite sex on the other team,” she said, showing us the card.
Well, there it was. The game had finally revealed its biggest twist. And honestly? It wasn’t that bad? Becky bounced out of her chair, went around the table, and kissed her brother on the cheek. They both giggled nervously. Then Becky sat back down. She gave me a shrug.
I was next and I got a purple, one of the last. I started to stand up and pull down my boxers. Then the reality hit me, and I paused. I didn’t mind being naked if everyone else was too. But the truth was, just looking at the board, it was really unlikely that would happen. Why did I have to be the only one showing brain?
“What if I don’t do it?” I asked. The table turned and looked at me. “What’s the penalty?”
Sierra froze for a moment, then reached for the manual. I looked over at Becky for solidarity, and she gave me a small chin nod.
“It says you have to move back three spaces,” Sierra said. I didn’t see the big deal with that at all. So, I’d be behind. I mean, did I really care? It seemed like losing the game was a much lesser penalty than losing the last of my clothes. I moved my little butt-shaped token backwards and sat down, still in my underwear.
It gave me a moment to look at the state of the board. Even with my setback, we were all more than halfway through our journey. Yes, we were all in our underwear and we’d only done the first orange dare. But with so little of the path left to play, it was hard to imagine things getting much more interesting than this.
Sierra was next and she took a truth card. “Have you ever participated in a threesome?” she read. “Fuck.” She quickly looked away. She seemed surprisingly upset by the content of the card.
“Seriously?” Becky asked.
“It was before I met Joey,” Sierra said.
“Wow,” I said.
“It’s not as hot as it sounds,” Sierra said, still not able to look our way. “I was a freshman in college. I’d turned 18 a few months before. My boyfriend kept begging for us to be with another guy. He said it would be fun to ‘share’ me. Turns out I wasn’t the one he wanted at all.”
“Wow,” I said, again, but in a much different tone of voice.
“It’s silly now, but at the time it kind of broke my heart,” Sierra said, “I felt so rejected. Like, how bad am I that my boyfriend would rather be with another dude?”
“That’s not how it works,” Becky said, kindly, “You don’t ‘turn’ someone gay. They just are that way.”
“No, I know,” Sierra said, “Rationally, I get it. But in the moment, it hurt, you know?”
“I’m sorry, babe,” Joey said. He reached over and rubbed Sierra’s shoulder.
“Let’s get on with the game,” Sierra said, quickly.
Joey was next and he also earned a yellow card. But this one was different than what we’d gotten used to.
“You must answer one question honestly,” the card said. All of us looked at each other. The card was surprisingly opaque. What question? Who provided it? Sierra, our gamemaster, went and looked at the manual, but it didn’t explain anything.
“I guess, ummm, we just do what it says?” she said.
We sat in silence. Everyone mulling it over. The card was so random, it felt like anything was on the table. But then, that also meant that nothing was, either. It was another weird design choice in an already strange game.
Finally, I sat up and gave Joey a smirk. I didn’t mean to be mean to the guy. Honestly, I thought he was OK. Weird, sure, but who isn’t? He was clearly a talented artist, very smart. We didn’t have much in common, but since when was that a requirement of friendship? But I couldn’t get the idea out of my head. I knew I was putting him on the spot. In the moment, with everything else going on, I didn’t care.
“Who was it in the painting?” I asked. Everyone turned and looked at me. Joey’s face went a little pale.
“Wh-what do you mean?”
“The nude you showed us earlier,” I said, “Who did you paint?”
“Oh!” Joey said. His eyes flitted around the room. “She was, um, a model. You know? They bring them in for us. So yeah, just some random chick who does nude modeling for extra cash. I don’t know her name or anything.”
“Uh huh,” I said. Joey sat back with his arms crossed, defiant. Becky rolled her eyes. Sierra though, was looking at me quite differently. It was the same face she’d made when we were playing Scrabble and she was working out the best word to use.
Becky was next to go and she got a dare to fondle herself for one minute. Apparently, that’s what the sand timer was for. So, we turned that over and Becky lazily dragged her hands over her body. It wasn’t as hot as I’m sure the game designers had been hoping. Mostly, she just cupped her breasts and ran her finger over her panty-covered crotch till the sand timer ran out.
“How was it?” I asked.
“Eh,” Becky said.
Now it was my turn, and I pulled an orange. “Spank your partner’s bare bottom ten times.”
“Oh, come on!” Becky said.
“I don’t know, hon, you have been pretty naughty lately,” I said. Becky rolled her eyes at me.
“You better hope one of those doesn’t come up for you, buddy,” Becky said.
“At least it’s me doing it and not your brother,” I said. Becky looked over at Joey for a moment, then back at me. Was I wrong that my ‘consolation’ wasn’t all that soothing to her?