Chapter 20

Author’s Note: Let’s play a game. A really naughty game. Thanks for reading. Enjoy this den of filth!

The judicial approval of Kat’s divorce came quickly. Now, we simply waited until she officially was a free woman. To mark the thirty days, we decided to play a sexy countdown game. We called it “Thirty Nights of Naughtiness.” We put together thirty cards and, each day, drew a new one. Completing the day’s task earned you a certain number of points. At the end of the thirty days, whoever accumulated the most points, would win one Hall Pass. The Hall Pass entitled the winner to a consequence-free day to act on any desires.

To maximize the possibility that we piled up as many points as possible, we divided the cards into three groups. The first group assigned tasks, each worth five points, that the three of us could complete just among us. These were easy, but we wanted them to be fun things to expand our sexual camaraderie. The second group, each worth ten points, included items that would push our boundaries. These could be completed among the three of us or with someone outside the group, and they mostly focused on public or exhibitionist tasks. The third group, each worth twenty-five points, was where the rubber met the road. We weren’t allowed to complete these with either of the other two. They had to be with someone else, and, for Jess, she wouldn’t get credit if she did them with an escort client.

The key rule was that, unless you completed a task with someone in our group of three, there had to be photographic or video evidence in order to win the points.

All of us easily completed the ten “us” cards from group one. We had purposely stacked the deck with more of those up front to get us into the game and wrack up some easy points. The first real challenge presented itself on the seventh day. The card from group three read, “Have a one-night stand and make them cum at least twice. The person can’t be someone you’ve already chatted with on a dating app.”

Even for confident, sex-loving people, Kat, Jess, and I were a little unsure about how to go about this task. But twenty-five points were at stake, and we were competitive people. It was going to be one of the first nice days of the year and a Saturday to boot, so we agreed going out together to a trendy patio bar might make our chances of success better.

I, for one, was grateful the girls wanted to go with me. I hadn’t just gone out and picked up a one-nighter at a bar in years. If Kat and Jess were willing to help me, it would make things easier. The girls took advantage of the weather and wore summer dresses, while I opted for my usual shorts, polo shirt, and loafers. We piled into my Maserati Granturismo convertible. I was a sucker for fun cars, and this one fit the bill for spring.

We ended up at a popular, mostly outdoor icehouse that was bustling by lunch time. The crowd was a little younger than we were, which we thought would be an appropriate target for finding people who were willing to party until their decision-making skills fell by the wayside. Jess had packed each of us a coke bullet. We wouldn’t leave anything to chance.

There was a giddy, nervous excitement that felt new to us as we sat down and surveyed the scene. We started with brunch cocktails.

“This should be no big deal,” I said confidently. “Three friends out looking to get laid. Half the people here are doing the same thing.”

The girls laughed. The afternoon unfolded nicely. Without a major sporting event on TV to dominate people’s attention, the crowd had to entertain itself. We sat at a large, communal table, and as the bar teemed with party people and the drinks flowed, casual conversations unfolded naturally. Kat and Jess sat across from me, and I ended up talking baseball for a while with a guy who was part of a larger, predominantly female group. This allowed the girls to operate a bit more freely.

Jess would get us fresh rounds of drinks at the bar, assuming correctly that some male hunter would approach her. Kat took a more distant approach, trying to find men who would make eye contact with her and see if she could engage them in a bit of eye fucking to draw them to her.

I, on the other hand, was out of practice and pretty awkward. It was exciting chasing prey again, but, for so long, getting laid had been like shooting fish in a barrel for me. I had Kat and Jess anytime I wanted. I had Rita and Gloria on a regular basis, as well as the occasional fling with Jess’s escorts. I hadn’t had to chase pussy in years. But the prospect of scoring something fresh and new was invigorating.

Kat made a trip to the restroom to bump up, while I saw Jess making easy conversation with a distinctly younger, muscled guy at the bar. It was the second time in a row she had talked to him while getting drinks. Her slender legs shifted slightly, and her flowing dress blew up slightly. She hooked her blonde hair back behind her hair, a tell that she was flirting. Jess had an air of easy confidence about her. The escorting had made her even more refined in that regard.

I was about to hit the restroom myself, when Jess returned with drinks and a surprised smile crossed her face.

“Oh my god!” she shrieked. “Melanie! What are you doing here?”

I turned around, and behind me stood a tall, smiling blonde and a shorter brunette. Melanie was Jess’s lifelong best friend, and we hadn’t seen her in months. We were busy with work and the move, and Melanie had been jetting around on modeling shoots for her career, which was steadily growing. The brunette was unmistakably her little sister, Shelly.

Jess scrambled around the table to hug Melanie and Shelly. I stood up and hugged Melanie next, then she introduced me to Shelly formally.

“John, this is my sister Shelly,” she said. “Shelly, this is John, Jess’s boyfriend.”

“So nice to meet you,” I said. “I’ve heard so much about you over the years, it’s nice to put a face to a name!”

“Me too!” Shelly said enthusiastically. She moved in for a hug.

“What do you want to drink?” Jess volunteered quickly. “I’ll go get it.”

Jess went to the bar to retrieve two pitchers of mimosas, where she conveniently found the object of her flirtations once more. This time, I noticed he paid for the drinks. Melanie sat down and leaned into me.

“It’s good to see you, stranger,” she said.

“I missed you!” I said. “You seriously need to come over and see the new place. The pool will blow your mind.”

“Maybe we could come over tomorrow?” Melanie said, glancing at her sister.

“Yes! I want to see this pool!” Shelly said enthusiastically. I wanted to see her at the pool. She was a stunner. Only a couple years out of college, she had the fresh body of a coed. Well-tanned, her thighs rippled and showed her cheerleading past. Her athletic legs were showcased in short, tight white shorts. Her red tube top barely covered her midriff and displayed gravity-defying tits that looked so nice I wondered if Dr. Vivianno had blessed her with them. She had pouty lips and electric white teeth. I was totally enthralled by her. She was my exact type.

“Are you guys playing some sort of game?” Melanie asked in a whisper.

“It’s called Thirty Nights of Naughtiness,” I said. “Today is a one-night stand, but it can’t be someone you know already.”

“Jesus, John,” Melanie said. “You aren’t fucking around.”

“On the contrary,” I said, “that’s exactly what we’re doing!”

Kat rejoined us from her bathroom trip, looking wired and playful. She walked straight over to Melanie and gave her a hug.

“Oh my god!” Kat exclaimed. “I haven’t seen you in forever!”

Melanie introduced Kat to Shelly, announcing her as my “other girlfriend.” We all laughed. I made a point to lock eyes with Shelly and smile. Things were looking up, and I excused myself to the restroom for a little burst of energy.

When I returned, Melanie whispered to me again, “Jess said you’ve got a bullet? Can I get some?” I grinned at her and palmed it to her underneath the table, my hand reaching higher up her thigh than necessary. She whispered to Shelly, who then joined her on a trip to the bathroom of their own.

I smiled across the table at Kat and Jess.

“How are we doing, girls?” I asked.

“Mine is too easy,” Jess said. “He’s making puppy dog eyes and asked about dinner. I told him I had to hang out with my friend and her boyfriend for a little, but we should have our own happy hour after that.”

“You slut,” Kat said playfully. “I see the way you’re looking at Shelly, daddy.” She smiled wickedly at me.

“I can’t help myself,” I said.

“Just don’t make Melanie jealous,” Jess said.

“Wait, have you and Melanie?” Kat said.

I nodded, and Jess said, “Oh, girl, we have had some wild times.”

“How did I not know this?” Kat said.

“Now you know,” Jess said. “Wait until you meet her husband. He is gorgeous. Truly, one of the most handsome men I’ve ever met. But his dick? It’s not even four inches long.”

“Ah,” Kat said. “That’s such a shame, but it explains a lot.”

“Kat, I know that look,” Jess said. “You’ve got something cooking, don’t you?”

“There’s a guy back there with a wedding ring who keeps staring at me,” she said. “It looks like he’s just here with friends. I get a good vibe.”

“Maybe we get some food and see if we can’t go our separate ways and get this done,” I suggested.

“I can always eat,” Kat said. She mouthed “I love you” to me. I smiled at her, feeling happy.

Melanie and Shelly rejoined us, but this time Shelly sat next to me. She put her hand on my thigh, signalling me to take the bullet back from her.

“That’s good stuff,” she said. “And that little bullet is so cute.”

“I didn’t know you partook,” I said quietly.

“Everybody looks at the little sister that way,” she said flirtatiously. “But I’m actually the wild one.”

“Wild enough to keep up with me?” I teased.

“You should find out sometime,” Shelly said.

We rejoined the conversation, where the girls were working out what food to order. Time passed easily. The food came and went. Jess got two more rounds of drinks. Our buzzes set in. There was more coke all around, but not too much. I kept my focus on Shelly, and Jess appeared to have her young stud on the hook. That’s when we realized Kat had gone to the bathroom a while back and hadn’t returned.

Jess and I checked our phones, and she had sent us a text: “Don’t leave without me. Back soon.”

Melanie and Jess gossiped away, catching up, which let me put the full court press on Shelly. We talked about her attempts to become a pro cheerleader, auditions for a couple reality TV shows, and her sugaring. She was between daddies and working as a bottle service girl for the time being. I loved it. Shelly was just the kind of girl I had always been attracted to, drifting from one fun thing to another.

I was brought out of my infatuation by Jess, who put a hand on my back and whispered in my ear, “Melanie and I are checking out. Take good care of her. Maybe show her the pool.”

I kissed her and returned to Shelly.

“Looks like it’s you and me,” I said.

“Do you have any weed at your place?” she asked.

“Tons,” I said.

“Smoking is my favorite,” she said. She had put her lips close to mine.

I turned and saw Kat swishing her hips as she approached the table again. She had a shit-eating grin on her face.

“Twenty-five points,” she said, leaning across the table and speaking in a low voice.

“Are you fucking kidding me?” I said, genuinely surprised.

“Let’s go, and I’ll tell you,” she said.

“So what’s this game?” Shelly asked as the three of us walked to the car.

Kat and I filled her in briefly as we drove home.

“And what did you just get points for?” she followed up.

Kat seemed a little nervous to say it, but I put my hand on her knee and told her it was okay. I could see Shelly from the rearview mirror licking her lips.

“A one-night stand,” Kat said.

“Really?” Shelly’s eyes went wide.

“That’s the card today,” she explained. “A one-night stand where you have to make the person cum twice.”

“Holy fuck,” Shelly said. “That’s kinky! You don’t care, John?”

“I want to win!” I said with a smile. At that point, I think it dawned on her what I hoped to extract from her that day.

“It sounds like you all win playing this game,” Shelly said.

Kat laughed lightly. I sensed maybe she didn’t agree with Shelly’s statement.

“So who was it?” I asked her. “What happened?”

The wind from the convertible forced Kat to talk more loudly than she may have wanted to.

“It was the married guy I kept making eyes with at the bar,” she said. “I was trying to signal him when I was going to the bathroom, but he didn’t get it the first few times. So when I saw him go up to the bar to get a drink, I brushed against him and said follow me. It was so dorky, I said I saw him staring at me, and he said I had pretty eyes.”

“You do love to be flattered,” I said, glancing to make eye contact with her and squeezing her hand.