The Pleasure Cruise Ch. 05

This is the final chapter, and it's a long one. There's a lot of plot to wrap up before we get to the good stuff, but I hope the payoff is worth it.

Ravenna933 edited the story from the beginning, and her contributions made it immensely stronger and more coherent. Ninjasr4real also sent me a suggestion for the final chapter that I liked too much not to use. Thank you to both.

I awoke with a start around 4 AM, and I instinctively reached over to Lauren's side of the bed to see if she was there. Nope. I was still alone. The guilt and regret over my actions last night, giving and receiving oral sex to and from an easy redhead whom I wasn't even that into after ruining my chances with Danielle, washed over me like a flood. You're an asshole.

I got up, used the bathroom, then lay awake for a while, feeling miserable, before I eventually fell back to sleep again under the powerful sedative influence of the ship's motion. When I next became conscious of my surroundings, it was morning, and I heard a light rapping at the door to my cabin. It clearly wasn't Lauren, as she'd be able to let herself in. I quickly checked the time - just after 8:00 AM - and then got up, recognized I was still nude, put on a ship's issue bathrobe, and opened the door.

It was Emily, wearing a similar ship's robe and wearing the relaxed, radiant glow of a woman who'd been fucked senseless the night before.

"Morning!" she said chipperly.

"Good morning," I answered wearily.

"Mind if I come in?" she asked.

I gestured at the room, and she moved in, sashaying towards the bed and hopping on, sitting cross-legged. I returned to bed as well, crawling back to the warm spot and laying down, propping myself up on a pillow under the covers. I could easily see up Emily's robe to a pair of teal and pink panties, but she didn't seem to either notice or mind that she was flashing me.

"To what do I owe the honour?" I asked sleepily.

"Danielle and Lauren are still sleeping in my cabin, and I'm awake and bored and tired of sitting in the dark having to be quiet," she answered. "I just came up to see what happened between you and Danielle last night."

"Ugh." I sighed. "What do you know?"

"She came back to the room after Lauren and me..." she caught herself. "After we were done. She was really upset. I heard about the scratches on your back."

"Great, so you must think I'm a terrible person too," I said defeatedly.

"Not at all." She smiled. "Danielle's overthinking it."

I was surprised. "What?"

"Lauren and I teamed up on her last night to try to talk her out of it. We obviously let her talk out her feelings, and we were sympathetic, but she's got no reason to be jealous of you. You're a single guy, you can do whoever you want. It's not like you were cheating on her." Emily's bright tone of voice somehow didn't match the gravity of what she was saying.

"Sure, but that doesn't mean she still has to sleep with me," I countered. "I don't blame her changing her mind."

"She really didn't change her mind, though," Emily said thoughtfully. "She still really, really wants to. I just... well, Danielle overthinks everything. Remember, she's never had any experience with a random hookup.

"She's still in that high school mindset, thinking about it in terms of feelings, like does she like you, do you like her, will you someday be boyfriend and girlfriend, and so on. Sex is still a huge deal in her head. Which is not the right way to think about it. The right way to think about it is you're hard, she's wet, you both want it, the end."

"Please tell me she's not falling in love with me," I said cautiously.

"No. She's not. But part of her is telling herself that she should be feeling that way, and she should be treating this like you two are boyfriend and girlfriend already. Sex and love are the same, so if she wants one, she should be feeling the other." Emily shifted her position, and her robe fell open slightly. I couldn't see anything, but I was starting to suspect she wasn't wearing anything under it apart from the panties. "How do you feel about Danielle?"

"I really like her, and I think she's amazing, and smart, and beautiful, and I also recognize that when we're separating tomorrow and there's a fifteen-year age gap between us, there's no realistic chance of it being any more than a vacation fling," I answered.

"That's exactly how Lauren and I tried to tell her she needed to look at it when we talked last night," Emily said, smiling. "Don't overthink it. Just do what feels right."

"Why did you come up here to tell me this?" I asked.

"Because I wanted to find out if you felt the same way about her, and I wanted to tell you not to give up on my girl Danielle. I figured if you didn't know to keep after her, you'd stay away from her today. She'd never see you again, and she'd miss out on an experience that she really wants and needs to have." Emily smiled again, sweetly.

"You came to my cabin first thing in the morning to tell me to keep trying to shag your best friend?" I asked incredulously.

"She needs to have sex with someone, and you're the one she likes. There's no accounting for taste, after all." Emily stuck out her tongue.

"Is she still mad at me? Did she listen to you and Lauren?" I was having trouble processing this.

"She was never mad at you," Emily reassured. "She was disappointed. She overthought it within an inch of her life, and she finally decided to have no-strings-attached sex for the first time ever. Getting to that point for a person like Danielle is a process. You've probably slept with tons of women in your life, right?"

"I mean, I've never kept a list..." I didn't know how to answer.

"Don't worry, I'm not judging. You're 35, never married, good-looking, and you know how to talk to women. I'm sure you've had sex with dozens of girls, if not more. I'd be shocked if you hadn't. But this is Danielle's first time doing this, ever. You have to remember that."

"I do," I insisted. "I've never pushed her into anything."

"She told me that," Emily smiled. "She said you've let her ramble at you, never judged her, never pushed her, listened to her, supported and encouraged her, helped her to figure out stuff on her own. She said you were a really good guy, and Lauren's told me the same, and I've never seen anything to contradict that. Someday soon, once she has more experience, she'll realize it doesn't matter if the guy you're with has a history. But for now, she's just new at this."

"Do you think I should message her?" I asked.

"Not yet. Leave it with me," Emily responded. "I'll see how she's feeling this morning when she's up, and I'll update you later in the day. Sound good?"

"Sounds good. Thank you for trying to hook me up."

She leaned over and hugged me. "I'm not. I couldn't care less if you get laid again, and you apparently don't need my help, either. But I care a lot that my best friend gets laid, because that girl needs it so badly. She's the one who decided it should be you."

We sat eyeing each other for a moment.

"I miss Milos," she suddenly said, moping. She then lay down beside me in bed, pulling the covers up to her waist.

I was surprised. "That's an odd thing to say when you're lying in bed with someone else."

"We've been together since we were 16, Sean." Emily shot back. "We almost broke up a year ago. I never told anyone that, until I told Danielle just the other day, when we had that long conversation.

"We love each other, and we want to stay together, but we both were feeling like we were missing out on dating other people. We were both each other's firsts, and we didn't want to be together for the rest of our lives without ever seeing what else was out there. So, we semi-opened our relationship. I'm not allowed to have sex with anyone else, and neither is he, but otherwise we have each other's permission to flirt with whomever we want."

"I know a few people in less traditional relationships around my age, but it's not common to be that comfortable with yourselves and each other in your early 20's. That's really cool." I was impressed.

"Thanks. He has a couple of girls in his life that he flirts with, and there's a girl in Australia he sometimes sexts that he knows from online. I don't want to know more than that, and I trust he's not going to do something I wouldn't be okay with. Me, I flirt like mad with anyone I'm attracted to, and sometimes I climb into bed with older men on a ship." She shrugged. "It might not be conventional, but it works for us."

"That's really mature of you," I said. "Danielle obviously didn't tell me."

"I don't think she got it," Emily said thoughtfully. "She was convinced it meant I was cheating on him. I kept telling her it's impossible to cheat on him with his knowledge and permission. It's not the act of doing something sexual with another person that's cheating. It's lying about it. But she's too sheltered to really understand open relationships.

"I do have to say, though, that I'm glad I don't have to lie to her anymore about my relationship. I don't need for her to be like me. I only need her to accept me, and she always has, and I think she does about this too."

"You two really do seem to get each other," I observed.

"You already know how amazing she is," she gushed. "Besides, even if she didn't get it, I'm sure she still told you I'm a huge flirt."

"She did," I confirmed, "and I also have eyes of my own."

Emily smirked. "For the record, I'm not going to fuck you. Danielle wants you, and she can have you. But I'm comfortable enough from getting to know you over the past few days to know you're safe to flirt with, and that you're not going to push me past where I'm comfortable." She ran her fingertip up the lapel of her robe as she spoke, pulling it just enough to reveal another millimetre or two of boob.

Damn, she is doing it on purpose. Well, two can play at that game.

"You know I wouldn't ever push anyone anywhere they didn't want to be pushed," I answered. "But it's a little awkward wearing a bathrobe in bed, so I'm going to take it off." I made sure the covers were fully covering me below my waist, then pulled the robe off as Emily watched with interest.

"Are you wearing anything under there?" she asked curiously.

"That's for me to know." I winked at her.

She thought for a moment, then wriggled down under the covers, up to her neck. Momentarily I saw her robe come out from underneath. She dropped it on the floor, then sat back up, keeping the covers anchored under her armpits and across her chest.

"You're right, this is better," she said innocently, clearly trying not to smile.

"So how was last night with Lauren?" I asked.

Emily finally broke into a huge, stupid grin. "Let's just say that I'm glad you guys are our tablemates."

"That good, eh?"

"I guess it makes sense, but a woman knows instinctively what feels good," she explained. "Don't get me wrong, Milos can play my body like a piano now, but he was a fumbling teenager once like any guy. It took time and a lot of coaching to get him to get him to the point where he can reliably get me off. Lauren just... knew." She shivered at the memory.

"I won't ask you to kiss and tell, particularly about my best friend, but I'm glad you had a good time." I felt around under the covers for her hand, squeezing it.

"Another item off the bucket list," she said happily.

"Will Milos be okay with it?" I asked.

"I think so. I hope so. You know, I really didn't intend to go all the way with her. She's not the first girl I've ever flirted with. But Lauren..." She trailed off, sighing. "Milos always said jokingly that if I slept with a girl, it didn't count as cheating, because he'd find it too hot to think about being jealous. Lauren and I took a few naughty pictures for him last night. I hope he finds it as hot as he said."

"You've never cheated with a guy?" I pressed, remembering what Danielle had told me the day before.

"Never," she answered. "Flirted, gotten wound up, come within a hair's breadth of crossing a line? Sure. By some relationships' standards, we've cheated on each other, and it wouldn't surprise me if Danielle saw it that way. But not by ours. I stand by our record. We're getting to explore our sexualities, and we still have each other. He doesn't care who makes me horny, as long as I always come home to him when I want to do something about it."

"Very cool," I approved. "Does it bother you knowing you'll never have sex with another man?"

"I'm still young," she responded, "and someday Milos and I will have a threesome, or a foursome. That's on my sexual bucket list, and he's mentioned he'd be interested too. So no, I'm not looking at it like I'm stuck with him. I love him, and I'm happy to be with him forever, but I somehow don't think I'll die as an old lady wondering what it's like to have another penis inside me. It'll happen at some point, with his knowledge and permission, and probably with him there participating."

We sat for a moment, feeling the ship's rocking motion.

"I was just thinking back to the good times I've had in this room," Emily finally started again.

"You'll never forget your first time with a girl?" I asked with a smile.

"Yes; and playing that 'Last Time You' game sitting on this bed. Oh, my God, how hot was that?" Emily exhaled.

"It was definitely one of the most sexually-charged rooms I've ever been in," I remembered. "Were you disappointed in how it ended?"

"A little," she answered. "It felt like things were on the edge of getting out of control, and I wanted it to. But then, we stopped so suddenly. Even with Liam kind of killing the mood, I still was so unbelievably turned on. I think that's probably why I was so susceptible to Lauren's advances that night.

"I wasn't comfortable losing control around Liam, so it was the right decision. But that said, I've spent a lot of time since then thinking about what would have happened if he wasn't there and we'd kept playing."

"Thinking, or fantasizing?" I asked.

"Both." She flashed a wide, toothy smile.

"I have too," I said honestly. "I'm pretty sure we would have kept going until we all wound up naked."

"For sure we would have," Emily agreed, "and then we were all so turned on, we'd have had to have jerked off together."

"I'd believe it," I said. "I could see it going that way. All of us together."

Emily sighed deeply. "It's going to be a fantasy for the rest of my life, getting off staring at three cocks and two pussies. It's too bad I never even got to see any dick. The boys got to see two topless women, while the girls got shafted."

"You saw three topless men, if I remember right," I pointed out. "I'd call that even."

"Not the same at all," she said emphatically, laughing.

"Plus, I didn't see any pussy, and you've seen everyone's vagina who was in the room that day," I pointed out.

"I guess you're right!" she said brightly. "Though I've never really thought of Danielle in that way."

"No secret crush?" I asked.

"Never," she responded. "She's more like a sister to me, though we're pretty open with things like nudity. She's beautiful, but I can't imagine being attracted to her, and I'd never fool around with her. Not that she would be down for that, either. She's very much a straight girl."

"Lauren and I are open with nudity like that, too," I mentioned.

"Lauren told me that," Emily said. "It seems a little strange for opposite sex friends to have that relationship, but then again, I like girls too, and ogling the girls in the locker room doesn't seem weird to me."

"Is that hard for you?" I asked.

"Sometimes it's wet for me," she responded drily. "Not often. But it's happened."

"I bet. It'd be hard for me having to change in the women's locker room," I said thoughtfully.

"I'd be okay if you were hard in the women's locker room," she said, sighing. "Oh! Not to change the subject, but I meant to ask you, can I see the scratches on your back?"

I groaned. "Sure, I suppose."

I rolled over in bed and Emily sat up, holding the blanket strategically over her chest. She looked at my back with interest, tracing Lena's patterns up and down. I suddenly felt the covers pull down over my ass.

"Hey!"

"Can't you let a girl ogle your butt sometimes?" she asked playfully. She gratuitously copped a feel. "Nice scratches. Do you want to tell me what happened?" She left her hand on my ass, gently stroking it.

"Do I have a choice?" I asked.

"I'd really like to know. I won't tell Danielle, I promise. I'm just a huge pervert. I like hearing other people's sex stories." Emily smiled sweetly and turned her body as I rolled back over. She was now lying on her side, the blanket pulled down far enough to reveal cleavage, though no nipple.

"I'd have thought Lauren would have worn you out last night," I commented.

"She did," Emily confirmed. "But that was last night. One week per month of my cycle, my libido is pretty much out of control. You met me during horny week."

"Lucky me." I proceeded to tell Emily all the dirty details about the bachelorette party that I'd held back the other night, including my night with Lena, and Oliver hooking up with Allison. I left out only the shameful hookup with Hannah I'd had last night. She listened in rapt attention as I tried to give her as much sexy detail as possible. It was official, I was now trying to turn her on.

"Super hot," Emily said once I'd finished. "I'll never get to do stuff like that, but it's fun to live vicariously through other people's hookups."

"Does it bother you hearing about Oliver and Allison getting together?" I asked. "You seemed to like him."

"He's gorgeous," she responded, "but no, I was never going to sleep with him. That would be crossing a line with Milos. It's just flirting. Same as you and I are doing right now. I'm glad he got laid. He's a good guy."

"I like flirting with you, but for all I know, you're testing me to report back to Danielle," I ventured carefully.

Emily looked surprised. "I hadn't even considered that," she responded finally. "I mean, sure, if you tried to fuck me right now, I'd shut it down, and I'd definitely warn her. But I see you as a cute, safe guy to flirt with. You haven't done anything all week to make me think you were trying to hook up with me. You've been obviously focused on Danielle."

"I'm still really hopeful things can work out between Danielle and me," I said, "but regardless, I also don't want to do anything that Milos wouldn't approve of."

"I know, and I thank you." Emily leaned over and kissed me on the forehead. Once she'd kissed me, she rolled into me, and I felt her skinny, warm body curl into my arms. We lay there for a few minutes as I tried to ignore the feeling of Emily's naked breast pressing into my side, or her hands playing idly with my chest hair. I wrapped my arm around her, gently stroking the small of her back, occasionally letting my hand drift down to her small, firm butt. I wasn't sure where the line was with her, so I decided I was only going to touch her in places where she'd already touched me.

Emily's phone eventually buzzed in her robe pocket on the floor. She sat up, nonchalantly revealing her topless body as she grabbed her phone out of her robe. "Danielle and Lauren are up, and Lauren's on her way up here. I'm going to head down and shower," she reported.

"Thanks for coming up," I said gratefully. "I appreciate your telling me what you did."

"If you want to seduce Danielle, the most important tip I can give you is not to give her a chance to think about it," Emily answered as I tried not to stare at her tits. "If you can get her instinct to make the decision, then you'll get laid. If her brain makes the decision, she won't figure out that she still wants you until next Christmas."