The Pleasure Cruise Ch. 03

"Nope. I'm too chicken to approach a strange guy like that," she said sadly.

"Sean will help you!" Lauren offered.

"You would?"

"We both will!" Lauren had seen an opening. "Do you care about the rules at all?"

Allison scoffed. "No chance."

Lauren's eyes lit up. "Then we'll help you cheat!"

Allison smiled, the first smile I'd seen from her since meeting her earlier that day. "Okay, that sounds like fun. Fuck my sister and her stupid slutty game, but at least I'll go in there and surprise them that I'm not the goody two-shoes they think I am."

"Let me see your scorecard." Lauren grabbed it off the slot machine.

"Can I see?" I asked.

"You're a man, so no chance." Allison and Lauren exchanged a knowing look. "Jesus, this is really dirty," Lauren said in surprise. "I've done a dirty scavenger hunt before at a bachelorette, and it was tame compared with this."

"Olivia's the maid-of-honour, she designed the game," Allison explained. "If you ever met her, you'd understand. I don't think there's a woman in America less deserving of the title 'maid of honour'."

Lauren snickered. "Would I be guessing right to say you don't want to do any of this stuff in public?"

Allison's eyes widened with anxiety, and she quickly shook her head.

"OK, come back to our cabin," Lauren invited. "Sean will get you off the mark."

"We know of a couple of other guys on board we could call to get you a few more checkmarks," I offered. "I bet Liam and Oliver would help out."

"Thank you." Allison gathered her things. "I don't want to try to beat my sister's friends at their own game, but if I can at least avoid coming in last, it'll stop the prude jokes."

"Are you a prude?" Lauren pressed.

Allison blushed, and thought about it. "I wouldn't think of myself that way," she finally answered. "I prefer to keep private things private. But I'm not repressed, I just don't advertise my sexuality to the entire world."

The three of us headed for the elevator, and a few minutes later, we were back in our cabin. I sat down on the bed as the girls commiserated.

"Okay, so it won't count if Sean does something for you that he's already done with either of the other two girls, so we have to pick another thing," Lauren began. "The timestamps on the photos make it impossible to cheat with that. So, giving him a lap dance and having him describe a sexual fantasy are out. It looks like there are..." she counted quickly. "There are twelve items on the list. Of the ten left, what do you want him to do?"

Allison looked the list over again. "I kind of want to shock my sister and her friends a little."

"Get one of the more outlandish ones done with someone safe?" Lauren offered.

"Kind of, yeah," Allison agreed. "I guess you're safe, right? I must trust you two enough to come to your cabin alone."

"We won't bite," Lauren reassured her.

"How about that one?" Allison pointed.

Lauren's eyes widened. "Are you sure?"

"It's the sluttiest thing on the list," Allison observed. "It's the one they'll least be expecting me to do."

"What?" I interjected.

"You won't say no, I promise," Lauren smirked.

"I trust you."

Allison turned to face me. "Sean, will you take a topless selfie with me?"

My jaw dropped.

"His silence means yes," Lauren explained.

I nodded. "How do you want to do this?"

The girls started talking quietly, plotting. After a few moments, Allison stepped into the bathroom as Lauren handed me Allison's phone. "The rules say it has to be a selfie, so one of you has to take it. Allison doesn't want to have a real nude on her phone for her sister to see, so our idea is that she'll cover her boobs with her hands for the picture and you take the picture. Deal?"

"Deal, wingman." I started removing my shirt.

Lauren smiled ear-to-ear. "This evening is getting more and more interesting."

Allison suddenly emerged from the bathroom. She was topless, covering her chest with the flannel shirt as she stepped out into the room. Her plain black bra was in her free hand, and her face was red with embarrassment. I saw her eyes move up and down my bare torso, checking me out.

"Are you sure you're okay with this?" I asked her.

"I'm sure," she responded with determination. "I'll show them."

I reached around her, pulling her closer to me by the waist as I lined up the shot. Allison dropped the bra and flannel, keeping her fingertips strategically over her nipples, but otherwise letting it all hang out. Her breasts were large and heavy, and soft and warm as her left boob pressed into my stomach as she moved in close. I couldn't resist admiring them in the camera display as I took the picture.

"Do you want one on your phone?" she asked as I set her phone down. Her fingers were still glued to her nipples.

"I'd love one, but are you sure?" I asked.

"Call it a thank you for helping me."

I lined Allison up again, pulling her in close, and I noticed her facial expression had grown a little more relaxed. I repeated the previous photo on my phone as we grinned for the camera.

"I really appreciate what you guys are doing for me. Thank you." Allison suddenly reached around me in a tight hug as two soft, naked breasts pressed into my bare chest. She held it for a few seconds, then loosened her grip enough to look up at me, but not enough to break contact between our chests. "Close your eyes."

I closed them, and I waited a few seconds as she disengaged from the hug, until she told me to open them again. The bra was now back on, and she was pulling the flannel top over her head.

"You've got really nice tits," Lauren observed.

Allison turned red again. "You mentioned you had other people you can call?"

"I'll message Oliver and Liam," I volunteered.

"Are they good guys?" Allison responded nervously.

"Oliver is. Liam I'll break his nose if he tries anything." She laughed, then noticed Allison's expression. "Don't be scared. Oliver's a total gentleman, and he's gorgeous. You'll like him. Liam's more of a fuckboy type, but he's all talk." A few moments passed.

"They're coming" I finally said, reading Oliver's response to my text. "They're just finishing a late-night workout in the gym, but once they've showered and changed, they'll come to the room. So, we have a little time to kill. Do the rules say that the scavenged have to be men?"

"Probably, but I don't think it matters," Allison responded. "If I came back with a girl on my scorecard, they'd be so shocked they'd let me count it."

"Then I'm giving you a lap dance!" Lauren exclaimed.

Allison froze in fear. "Um, thanks, that's nice of you to offer, but I'm straight."

"It doesn't have to be a real lap dance, right? What if we just took a picture?" I pointed out.

Allison thought. "That actually is a really good idea. I'm down."

She moved to the chair in our room, and Lauren arranged the photo, mussing Allison's hair a little and unbuttoning a few buttons on her top, exposing her ample cleavage. Lauren applied fresh lipstick then kissed Allison on the cheek, leaving a print, then climbed into her lap as Allison sat stiffly.

"Do you want to put your hands on my tits?" Lauren offered.

Allison sat wordlessly. Lauren took that as an invitation, taking both her hands and placing them on her chest. "OK, Sean, take the picture."

I snapped a quick shot. "Allison, you look like you're at the dentist."

"I'm sorry... this is all new to me."

"You don't have to do anything you don't want to do," I reassured her.

She smiled. "Thanks, Sean. I think I want to do this. I need to push on my boundaries sometimes. It's good for me." She adjusted her position in the chair, spreading her legs, then took Lauren's hand and put it under her top, on her breast. She then turned to face me. "Take a few, we'll delete all but the best one." She then whispered something to Lauren, who started lap-dancing on her for real.

I moved around the room, capturing what I could on Allison's phone, as Lauren fell into her familiar role of seductress, trying, with evident pride in her work, to make the bigger girl uncomfortably horny. She rode Allison for all she was worth, first straddling, then grinding her butt into Allison's crotch, running her hands all over her body through her hair, under her shirt, everywhere but between her legs, nibbling her neck, then kissing her deeply as Allison held on for dear life. Finally, Lauren stood up.

"Did you get what you needed?" she asked me with a smirk.

"I think we did!" I responded, tapping the phone and looking back through the two dozen or so photos I'd taken. Allison stayed glued to the chair, her legs open, hair and clothes dishevelled, a far-off look in her eyes.

I quickly sorted through the photos, deleting any that were blurry or unusable, then handed the phone to Allison. She quickly looked through the quarry with Lauren watching over her shoulder. Allison blushed as she reached one photo.

Lauren cackled and showed it to me. "We've got our winning shot."

Lauren was grinding her butt on Allison's crotch as Allison raised herself off the chair slightly to meet the stimulation. The look on Allison's face was pure, unbridled lust, and I noticed in the picture that one of her hands was clutching her breast. I'd been so involved in taking pictures that I hadn't noticed that in the moment. Lauren's face was a study in concentration, but she also wore a look of enjoyment, and of power. In addition, the lighting and focus were perfect -- I'd managed to capture a story in an image.

"So much for little shy Allison," she finally said, pride evident in her voice.

A sharp knock came at the door. Allison slammed her legs together, fixing her dishevelled clothes and wiping the lipstick stain off as Lauren went to the door and opened it.

Liam and Oliver entered, both wearing workout gear, though judging by the lack of sweat, it appeared it was cooldown gear they had on. They both had wet hair, and they smelled like they were freshly showered. I caught Allison checking Oliver out as Lauren brought both men up to speed on the scavenger hunt, including going over the rules. We may have broken them, but I knew Lauren didn't trust Liam, and didn't want to give him the opportunity to argue about what he was going to do with Allison.

"So, she gets to ask us to do something off her list, and we do it with her, and then she uses that in competition? Sounds like fun." Oliver smiled his million-dollar smile, and Allison noticeably swooned as Lauren handed her the scorecard.

"Okay, Liam..." Allison thought a little bit. "I need to get a selfie with a guy with his underwear in my hands. Do you want to take yours off so I can do that? You're welcome to change in the bathroom."

Liam looked nonplussed. "I mean, sure, that's no problem, but I'm not wearing any." He gestured to the loose gym shorts he was wearing. "When we got your text, we just came straight here. I only brought enough clothes to the gym to get back to our cabin after working out."

"Dammit." Allison looked crestfallen. "According to the rules, I can't ask you anything else."

"How about using one of my pairs?" I asked.

"Great idea!" Lauren went rooting in a drawer, finding a clean pair of my boxer briefs and tossing them to Allison. She quickly lined up a selfie, holding my underwear up as a trophy, as her and Liam mugged for the camera.

Once the picture was safely taken, she tossed the underwear back to me and kissed Liam on the cheek. "Thank you, you've been a big help."

"Anytime."

"What do you have for me?" Oliver asked.

"This one seems pretty safe," Lauren pointed at an item on the card.

"Agreed, but I think I like this one better," Allison responded.

Lauren raised her eyebrows. "It's your scavenger hunt. Go for it, girl."

"Oliver, would you..." her voice cracked. "Would you give me a spanking?"

Oliver was cool and collected with his response. "Clothed or bare-assed?"

Allison blushed again. "Let's say clothed."

She climbed onto our bed and handed her phone back to me as she assumed a doggy-style position, presenting herself to Oliver. I lined up the photo to get both faces in frame, and then nodded to Oliver as he began, starting with a gentle touch of her ass, almost copping a feel, before suddenly smacking with enough force for her to feel it, but not enough to hurt her. He then started massaging her butt, smacking it occasionally, but doing it slowly, sensually, teasing her. His hands roamed over her legs, her lower back, her inner thighs. I kept snapping pictures as Allison started to moan under her breath each time Oliver's hand came down. I was pretty sure from the angle I was standing that I was the only one in the room who could see Allison's face, and she was flushed, wearing a look of pleasure, and starting to breathe more shallowly.

I looked over at where Lauren and Liam were standing. Both of them were watching, engrossed, as Oliver went to work. Liam was obviously hard in his unrestrained gym shorts, with a noticeable bulge making the shorts tent slightly, and Lauren's face showed an expression that was both bemused and turned on as she bit her bottom lip.

"I think I've got enough pictures," I finally interrupted.

"Shut up, Sean," Lauren ordered.

I sat down, putting Allison's phone down on the nightstand, as Oliver continued working on her with practiced restraint. She was fully in heat now, moaning and grinding her butt back at his hand as he worked on her. I noticed him finally slide his hand between her legs as she grunted in response.

"Do you like that?"

Allison nodded.

"Good girl."

Allison suddenly unbuttoned her jeans, pulling them down just enough to expose her butt. She had a bigger one, but it was shapely, and her skin still had the smooth softness of youth. Her butt was red from where Oliver had been spanking her. The dull thud of his hand making contact changed to a loud, skin-on-skin smack each time he hit her, and she was now actively moaning, not even trying to be discreet.

She finally rolled over. "Enough teasing," she said. Her legs were spread wide, and her jeans were down just enough that I could see the beginnings of a patch of dark brown pubic hair on her mound. Her eyes were begging Oliver to fuck her.

Oliver suddenly looked unsure. "Is this still part of the scavenger hunt?"

The spell was suddenly broken as Allison clamped her legs shut, embarrassed, as she remembered she had an audience. She quickly pulled up and rebuttoned her jeans. "What time is it?" she asked.

I checked my phone. "11:20 PM."

"We have to get to the lounge to total the scores," Allison said. "I'm not missing that, or else they'll think I chickened out."

"Can we come?" Liam asked.

"Be my guest." Allison finally picked herself off the bed, straightened her clothes, and we headed as a unit down to the lounge. As we were leaving the room, I heard Allison quietly say to Lauren, "I'm so fucking horny right now. Don't let me do something I'll regret."

We were the last to arrive at the lounge, right on time. I picked out Andie right away, curled up on a sofa with a long-haired guy who looked like a musician. I noticed her surprise seeing her sister come in with an entourage. Both Hannah and Lena smiled at me as we walked in.

"Okay, we're all here, ladies. How did we all do? Everyone at least off the mark?" A dark-haired skinny girl in a low-cut halter top looked with barely-disguised contempt at Allison as she said that, who gave her the finger in response.

"That must be Olivia," Lauren whispered at me.

"Everyone, please turn in your scorecards and your phones, and I'll tally the winners," Andie said. Allison, Lena, Olivia and Hannah all put them down on a table, as did a fifth, light-haired, freckled woman I vaguely recognized from snorkelling that afternoon.

Andie worked quickly, sorting through pictures and scorecards, occasionally laughing at something she saw. The room sat mostly in silence, for about ten minutes, making small talk with the groups we were with, though Hannah kept making kissy faces at me. I tried to flirt back with her at a distance, though the longer I watched her, the more I realized that she was absolutely shitfaced. She was having trouble staying steady leaning against a wall, and her movements were those of someone who appeared a few minutes away from passing out.

"That's a no," I whispered at Lauren.

"Too bad," she agreed. "That girl's not going to make it to someone else's bed tonight. She needs her own."

Just then, the bride picked up Allison's phone, and I watched her eyes widen as she looked through the pictures of her sister's evening. Her jaw dropped, and she kept looking back at Allison, who was staring her down in defiance.

"Okay ladies, we have our results!" Andie finally announced. "In last place, with a score of 3, is... Brianna!"

Olivia looked at Allison in surprise, who smiled smugly in response.

"Next, we have a tie! With a score of 4, Lena and Allison!"

Lena offered her hand to Allison, who shook it enthusiastically, looking very proud of herself.

"That leaves two contenders for the win tonight, and I don't think either of us are surprised who the top two contestants are. You slags." Andie grinned, holding a scorecard in her hands like it was the Oscar results. "The winner of a gift card for $150 worth of sex toys, with a score of 11, is... Olivia!"

Olivia stood up and curtsied. "I'll put them to good use."

"Second place goes to Hannah with a score of 9!"

Hannah tried to wave, but she lost her balance, and stumbled slightly before catching herself.

"This concludes the formal portion of the evening! Thanks for playing, everyone." Andie turned her attention back towards the long-haired guy with evident lust in her eyes as the room began to disperse.

Hannah made a beeline to me. "Sean!" She collapsed into my arms, and I held her weight upright as she regained her balance. She breathed deeply into my chest. "You smell good."

"We'd better get you to bed," Allison said, springing into action.

"I don't want to go to bed," Hannah slurred, turning to face Allison. "I want to fuck."

"Tomorrow," Allison reassured.

"But I'm horny now." She suddenly stumbled again, falling into Allison's arms this time.

"No arguments." Allison turned to Oliver. "Can you help me get this one back to our cabin?"

"I'd love to," he grinned.

"Do you need another hand?" Lauren quickly asked.

"I think we'll be good, but thanks for checking." Allison and Lauren exchanged a knowing glance, then the she, Hannah and Oliver made for the exit together over continued protests from the redhead.

After they left, I sidled up to Lena. "Hey, stranger."

She turned to face me and smiled. "Hey. You'll have to forgive me, I don't believe I remember your name."

"I don't believe that I remember yours either," I lied. Lena played with her hair expectantly, the tension thick in the air between us. "My cabin or yours?" I finally asked.

"Mine," she responded, breaking out in a big grin. She turned and motioned to Brianna, who was chatting with Liam. "I'll be using the cabin for a bit. I'll text you when the coast is clear." Brianna nodded her approval, so Lena turned back to me. "Let's go, stranger."

Lauren pumped her fist at me as Lena and I left the room, and I mouthed a thank you at her as we headed out into the hallway, towards the elevator.

As soon as we were in the elevator with the door closed, Lena leapt into my arms, and I grabbed her by the cut-offs, holding her up as she wrapped her legs around me and kissed me aggressively. She was lighter than any woman I'd ever held in my arms before.

The elevator stopped on the second deck, where Lena released me, then took me by the hand, wordlessly leading me to a cabin near the stern on the port side. When we got there, she unlocked the door, leading me into a room that looked identical to ours, except for having two beds instead of one, and a window instead of a balcony. The room was a bit of a mess, with clothes and makeup strewn everywhere.