Mystery Prize Ch. 02

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Mystery Prize

Chapter 2: The First Night

Note: Many, many, many thanks to MissBoePeep who’s editing and input was fantastic! For those wondering, yes, I needed to make an excel spreadsheet in order to keep track of who ends up paired with who during the climax (har har har) of this chapter!

Cait, Lucy and I made our way to the main dining hall. The women onboard were wearing an array of outfits, many similar to both Cait and Lucy’s. Cait wore a knee length black and white leopard print dress with dark stockings underneath that really accentuated her long, thin legs. Lucy wore a pink and yellow floral print dress that showed off every curve of her excessively curvaceous figure.

“Aw crap,” I commented, seeing what most of the men onboard were wearing to this first dinner.

“What is it baby?” asked Lucy.

“They’re all wearing ties. Everybody’s wearing a tie. I guess I should go back to the room and get mine.” I sighed — I hated wearing a tie.

Lucy grabbed my hand and swung herself in front of me. She ran her hands across my chest and commented, “Sweetie, you are the most handsome person on the boat. You don’t need to do anything.” Slowly, her hands moved from my chest down to my waistband. She pulled me close to her, gripping two of my belt loops with her thumbs. “The only thing you need to do is to wrap your arms around me and kiss me, okay?” Our lips met, and she kept pulling me closer. Soon, our tongues danced with each other, exploring each other’s mouths. The kiss ended and Lucy cupped my cheeks in her hands. “See sweetie? I think you’re prefect!”

“Me too!” Cait said, reassuring me. “Ties are over rated anyway! It’s just one more thing to take off!”

I smiled, reassured about not wearing a tie and we carried on into the dining hall. It was amazing! Crystal chandeliers adorned the ceilings. The walls were completely made from glass, allowing us to see the beautiful sunset over the ocean on the starboard side of the ship. The maître d’ greeted us at the entrance, and looked at the three of our keycards. He introduced himself at Bernardo and was from Buenos Aires, Argentina.

“Ah yes, Miss Johnson,” he said handing Cait’s card back to her, “You’re at Table 33. If you’ll follow this gentleman here…” he indicated for her to follow one of the wait staff to her table. “And you, Mr. and Mrs. Hobbes. Please follow me and I’ll show you to your table, number 52.”

We followed him, and soon found ourselves seated at the center table in the dining hall, which had seven chairs set up around it. “We seat all our VIPs at table 52 on each of our cruises. Your other tablemates will be here soon. Please take a look at our menu and enjoy the first meal!”

We began looking over the menus only to be interrupted moments later by Bernardo again. “I’m sorry to interrupt your perusal of the menu, but this was sent from Ian, the cruise director, for your pleasure.” He presented us a bottle of expensive looking wine. We thanked him and asked that he send our gratitude to Ian if he saw him before we did.

A few minutes passed and eventually our table with five empty seasts began to fill. The first two to join us were a couple in their mid-forties they introduced themselves as Sam and Alice Goldberg. Next, we were pleased to be joined by Sheila, the woman we first spoke to when we were waiting to board the ship. We chatted with the Goldbergs’ and Sheila for a little while and were soon joined by our final tablemates, a gay couple, Gary and Mark Peterson. Sheila had a seat at table 52 since her second cruise with her husband, and although he had passed away the cruise line allowed her to keep her seat at the VIP table. The gay couple had also won the cruise in a contest and the other couple had been on many previous Pleasure Cruises and knew Sheila well.

We shared our bottle of wine with our table and finished our dinners. As you’d expect, the food was perfectly prepared and delicious. After desert, we told our table that we were going back to our room to relax before the evening’s activities.

“Remember that tonight’s still a formal night,” Sheila reminded us. “You’ll definitely want to come to the theatre tonight. There’s a show where they include volunteers from the audience. It’s always a lot of fun!”

“Okay!” said Lucy cheerfully. “We’ll have to check it out!”

We said goodbye and went back to our room to relax and take a nap for a few hours before tonight’s show.


After such a long day, we fell soundly asleep almost immediately when we got back to the room. We were awoken later by a commotion coming from Cait’s room. When we fell asleep, our half of the adjoining door had been left open by mistake. It sounded like Cait was fighting with someone on the other side. Concerned, we pushed open Cait’s side of the door to make sure she was all right.

To our shock, Cait was sitting at the end of her bed between the legs of another woman. An attractive brunette was lying on the bed, with her skirt hiked up above her waist. Her thong panties were on the ground next to her, leaving kağıthane escort her spread eagle, while Cait was eating out her juicy pussy. Cait was still clothed from dinner, while she ate out the brunette her ass wiggled back and forth in the air, showing off her own saturated panties under her skirt.

The brunette let out a loud, long moan; obviously, Cait was doing a great job. It must have been the moans of pleasure that woke Lucy and me, not a struggle. Cait tried to pull away from the brunette’s pussy, but her legs wrapped around the Cait’s head. “Keep going, God dammit!” she shouted. Cait lifted her head just long enough to take a deep breath, and went back to work. She gently fingered the brunette while sucking her clit, all the while the brunette squirmed with pleasure. Cait reached up, and began fondling the brunette’s breasts beneath her blouse.

“Yeah, you like that, don’t you, you dirty slut!” Cait said slyly as she licked and sucked the other woman’s clit.

“Yes! Oh God yes! I’m almost… almost…” the brunette let out a long moan, and her body tensed with pleasure as she began to cum. “Uuuuuuuughhhhhhhhnnnnnn! Watch out! I’m going to…!” Her whole body shuddered and even though she attempted to give her partner warning it was too little too late. A stream of ejaculate erupted from her cunt, soaking Cait’s face, red hair and blouse!

Cait leaned forward, still covered in the brunette’s cum and gave her a passionate kiss on the lips. “I loved that, and you taste delicious, sweetie,” she said, wiping off her face and licking her fingers. She stood up, and offered the brunette help up to her feet as well. We then saw it was Jennifer, the woman Cait was making out with earlier.

We tried to close the door, but we were too late. Jennifer turned bright red, having been caught by Cait’s neighbors. Cait noticed Jennifer’s blush and quickly turned around. She adjusted her skirt, covering her soaked panties and wagged a finger at us. “A couple of voyeurs! That’s what you two are! Aren’t you?”

Lucy and I were speechless, and couldn’t answer. She continued, without waiting for us to answer anyway. “Judging from the bulge in Cal’s pants, I’d say you two enjoyed watching though, don’t you think sweetie?”

Jennifer nodded, and adjusted her clothes as well. Though she was out of breath, she walked up next to Cait and kissed her cheek. “I’m glad we could be so entertaining for your neighbors! Maybe next time, they’ll join us.”

“We just might!” Lucy said, stepping through the doorway into Cait’s room. “I’m Lucy, and this is Cal.” I was a little taken aback at how calmly Lucy was reacting to the situation. But maybe she was just trying to make an awkward situation a little less awkward by making our introductions.

“I’m Jennifer,” she woman said, shaking Lucy’s hand.

“I’m sorry we snooped, but we thought Cait was having a fight in her room. We wanted to make sure she was okay,” Lucy explained. “We were napping and heard such loud screams we got worried!”

Jennifer blushed again, but smiled. “Oh, I’m so sorry I woke you! I can be really loud when I’m enjoying myself!”

“—And wet!” I observed stepping into the room. I braced myself for blurting that out, as I expected, Lucy elbowed me and rolled her eyes. The three women laughed out loud at my muffled “oomph” upon impact. “Seriously though, you’re reacting to this much differently than I would have expected, Luce. I probably am too; I have a little confession for you.”

“Oh, and what’s that?” Lucy asked me, arching her eyebrows and putting her hands on her helps, threateningly.

“I, well, I did some research and we’re not on a regular cruise ship. We won a trip on a ship made for swingers, exhibitionists and other people like that. I…well I actually signed up to win this trip so we could add some spice to our love life. This kind of thing is going to be pretty regular on board.” I looked embarrassed and ashamed.

Lucy shot a look at the two other women in the room, exchanging glances with Cait in particular. “Oh, Cal,” she said sternly and approached me. Her hands were still at her waist, I was sure I was about to get yelled at. “I don’t know how you could keep this from me!”

Cait snickered and whispered something to Jennifer. I felt even more badly for keeping this from Lucy.

“Seriously Cal? How could you keep this to yourself? You tell everybody everything! I didn’t think it was possible for you to keep a secret! Even our mechanic knows about the time I threw up on the dentist!”

“I—” I began to try to explain myself and then noticed that, to my surprise, Lucy was now smiling sassily at me. “Wait. What?”

The three women now erupted in laughter, I had no idea what the joke was, but I sure didn’t get it.

“I can’t take it anymore!” Cait said, through her laughter. “Cal. When Lucy and I were getting ready for dinner, she told me that she had done the exact same thing!”

“She what?” I asked, still not quite grasping it. Lucy beamed with pride.

“Oh, kartal escort bayan Cal. I was trying to keep it from you!” She hit my arm. “I can’t believe you were able to keep this a secret! But I’m glad that we don’t have to keep this from each other anymore. Aren’t you?”

I finally caught on. Lucy knew exactly what this cruise was, and I was happy that we didn’t have to keep the fact we knew this was a sex cruise from each other anymore. “That’s so funny! Well, I’m glad you ladies helped Lucy and I come clean with each other… in such a dirty way!”

Cait reminded us about the time: it was just about time for the night’s show to begin in the theater. Jennifer said she didn’t want to see the show tonight; she was too tired. “That’s okay,” Cait told her, “We’ll have some more fun another time!”

Jennifer gathered her belongings, and said goodbye. Afterward, Cait told us she had to get cleaned up and then we were on our way to the theatre.


The theatre was already filling up with the other passengers.

“You find a table, I’ll get the drinks,” I said to the women as I made my way to the already crowded bar. It took a few tries but I was finally able to shout our drink orders to the bartender who quickly placed them on the bar and took my card. I signed for the drinks and looked around. The sea of people in the theatre made it just about impossible to find Lucy and Cait.

“Can’t find your wife?” someone behind me asked.

“Hmm? Oh yeah. I mean no, no, I can’t find her.” I replied, glancing back. I saw it was Hank, one of the other people we met earlier. “You’re incredibly tall; can you give me a hand? Lucy’s wearing a pink a yellow dress. She’s at a table with another woman wearing black although her outfit won’t be as helpful because everyone’s wearing black.”

“Sure, let’s see.” Hank looked around and finally his gaze stopped at a table near the stage. “I think that might be them,” he said pointing towards the table. “Let’s go take a look.”

“Sounds like a plan,” I agreed.

It turned out Hank’s bird’s eye view was right. Lucy was at the table laughing with Cait, I put the drinks down and asked, “What’s so funny?”

“Oh, never mind,” Lucy said slyly. “Oh, hello Hank. Where’s Stacey?”

“Right here,” Stacey said, putting her drink down on the empty table next to ours. “I was chatting with someone when Hank found you, Cal. It wasn’t hard to find him since he’s a head and a half taller than everyone else. Are you all ready for the show? You know there’s a lot of audience participation during these things right?”

“There is?” I asked sitting down in between Lucy and Cait.

“Absolutely! They always want to include everyone in their shows and games. It’s always really fun to watch, I couldn’t tell you what it’s like to be in them though. We’ve never been picked.”

“Neither have I,” added Cait. “But the last time I was on board the first show was the best icebreaker. After that, everything comes naturally.” She snickered.

The lights began to dim, indicating we should take our seats and quiet down. The curtain opened and Ian came out with a microphone in hand.

“And how is everyone doing tonight?” he said smiling. The audience clapped and cheered. “Aw, you can do better than that! What are you? Sea sick already? That’s a shame. I guess I’ll just have to go tell the captain to turn the ship around so we can find some real passengers!”

He pretended to walk off the stage as he ‘talked’ to the captain on his earpiece. Sure, it was corny, but Lucy and I joined the rest of the audience booing Ian. He came back on stage with a disappointed look on his face. “Well, the captain said he can’t turn the ship around, so I guess I’m stuck with you losers for the duration of the cruise. Maybe I’m wrong about you? What do you say? Think some of you can prove me wrong? Think you can prove to me that you deserve to be aboard Pleasure Cruises?”

The audience cheered again, hoping to show Ian that we did deserve to be aboard the Helios.

“Alright then, tell you what. We’re going to do a brand new game we’ve invented. I need three couples to volunteer to help me test it out. I also need two single ladies and two single guys. Who will help me out?”

A ton of people raised their hands. Lucy and I did not; we wanted to see what Ian had planned, not participate in it. Cait, of course, was just about jumping out of her skin to volunteer. She was not picked as one of the two single women. To our surprise, Sheila was picked as one of the single woman. Another woman was picked as a single, too. Two men we didn’t know were picked as the single guys. Finally, two couples we didn’t know were also chosen as volunteers.

“Well, I didn’t want to call them out here but we have two special guests in the audience,” Ian announced. “Hey, put the spot light on those two,” he instructed his stagehands. The spotlight moved away from Ian and shined down on Lucy and myself.

“Aw shit,” I murmured.

“What’s that, brother?” kurtköy escort bayan Ian asked, holding his hand to his ear, doing a horrible Hulk Hogan imitation.

“AW SHIT!” I barked back to him. Everyone in the audience laughed at me, but that was okay, I knew they would.

Ian waved us up onto the stage. Lucy excitedly skipped up; I followed her after finishing the last of my drink. If there’s one thing I really dislike its public speaking, and stuff of that nature. “You see, these two, Cal and Lucy, were the winners of our contest for a free VIP cruise aboard the Helios. I think they have to really prove they deserve to be here, what do you guys think?”

The audience cheered louder than ever. Clearly, they felt we especially had to prove ourselves worthy too.

“Alright, here’s the deal,” Ian said as some stagehands wheeled out a table with some blindfolds, numbered temporary tattoos, and curious looking bottles. “Guys, you’re all going to be blindfolded after applying your temporary numbered tattoo (we’ll get to that one later). Girls, you’ll each have 2 minutes to please the man in front of you anyway you’d like. Then, I’ll blow a whistle and you’ll each move to your left down the line. If you’re at the end of the line, you’ll just come back to the beginning. The game won’t end until every guy is… satisfied, if you catch my drift. You can use any of the oils we’ve provided on the table with the blindfolds, and just in case you’re wondering, they do actually taste quite good! Men, feel free to suggest to the women pleasuring you what you like and don’t like.

“We have a few other rules though, once you’ve cum, you’re out of the game until the next round starts. Ladies, same rules apply… once you’ve made the man you’re pleasuring cum; you’re out of the game too. That way, nobody’s left out! Even if there’s only one girl left, I’ll keep blowing the whistle so the guy doesn’t know he and you are the last ones left… but he’ll probably figure it out on his own! Once everybody’s blown their load, it’s time for the women to stand up and rearrange themselves, so nobody can guess what order they were in.

“Now comes the most fun part… well actually the second most fun part, because the first part will probably be the most fun, am I right? It’ll be up to you to try to guess a few things. First, the ladies will try to guess who they made cum. Then you men should guess which of the women made you cum. If you’re right you’ll get a prize! How does that sound?”

I gulped and felt lightheaded. “I think I need another drink,” I said to Ian.

“Me too,” another man said. Other men also agreed, as did a number of the women. Lucy didn’t say she wanted another drink, which surprised me a little.

Ian laughed and said, “That can be arranged, but before we begin I want to ask everyone, if you’re up for this game. Now’s the time to back out, because once we get started it ain’t gonna stop until the last one of you drenches one of the ladies with your warm, sticky, love juice. If you’re up here with a partner, talk it over with them and let me know. If any of you want to opt out, I’m sure there are many in our audience just dying to volunteer now! I’ll give you a few minutes to chat.”

Lucy and I whispered back and forth for a moment and then decided that we’d go for it since we were here and we wanted to push our limits.

“We’re in!” Lucy announced to Ian, she was the first to speak up.

One of the couples decided it was best they sit this one out. They explained they had just come from a “get to know you orgy” and his tank was completely empty. Ian laughed and told them their excuse was just fine. They left the stage and Ian quickly recruited another couple to come up in their place. Everyone else opted to stay.

“Alright, then we’re just about ready to begin the game, but there is one more thing. Audience members, some of our staff members are now passing out scorecards, if you will. On them, we’d like you to place bets on which order the guys will cum. You’ll also be trying to predict which woman will make which man cum. Anybody who is correct will win themselves one of our tasty massage oils! Sound good? So, what can I get each of you to drink before we begin?”

The staff handed out the betting slips while Ian took us backstage got us our drink orders. Lucy spoke up at this point, “I’m really not the best at giving head,” she confessed. “Can I have a large glass of water for me to drink throughout the game?”

“For sure,” Ian said and asked if anybody else wanted a glass of water as well.

“Couldn’t hurt,” I commented. Everybody else agreed, and asked for some water as well. “Can you give me a moment?” I then asked Ian. “I should take my inhaler before we begin. I don’t want to have an asthma attack during the show!”

“Definitely, where is it?”

I told him it was in my jacket pocket and he quickly got it for me. After taking it, I told him I was ready when everybody else was.


Backstage Ian instructed each of the men and women to apply the temporary tattoo to our right shoulders. We put on our numbers — I was number 5 — and afterward, he asked us all, men and women, to remove our clothes. It was the first time either Lucy or I had been naked with a group of people so we felt shy about exposing ourselves. It was pretty obvious we were the only participants not used to this sort of thing, so others gave us some encouragement.

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