The Pleasure Cruise Ch. 02

"Anyway, one night, my parents were out of town, so I talked to my older sister, and she was such a good sport about it. She loved Milos too! Not only did she make sure she vacated the house, but she also bought us lube and condoms. Not that I needed the lube, but I guess some girls do their first time.

"It was so romantic. We lit a bunch of candles, and we built it up for at least an hour before he penetrated me. Milos went really slow, and it didn't really hurt that much. I guess when you're so compatible with each other, it just works! I even had an orgasm my first time, and I've never met another girl who could say that.

"Obviously we've gotten a lot better at sex since the first time, and we're way better at it now than we used to be. But I'm so glad my first time was perfect, and with the man I'm going to marry."

She smiled. Emily's story might have been more sappy than erotic, but I was happy for her to have found someone that made her happy.

"I think it makes sense that Sean go next," Danielle interjected. It was the first thing she'd said since we sat down, so we all turned and paid attention. "That way we'll have someone from each pairing in the first three."

"Sure, no problem," I said. "I'm only telling this story because I'm not working at this company anymore and can't get into trouble."

"I'm... not sure I've heard this one," said Lauren, surprised.

"No one has. It was my first supervisory job. I was 27. In retrospect, I was too young and immature for the role they put me in, but I was muddling through as best as I could. I had twenty-five people working under me, and there were two new university grads, both women, that I supervised that I was pretty sure had crushes on me.

"One of them was kind of socially awkward. She would try to hug me, and I had to keep reminding her about professional conduct in the workplace. But she kept coming, and, like, when she'd hug me, it was like I could feel her arousal. Like she'd almost be shaking with nervousness talking to me. I also noticed that whenever we'd have a one-on-one meeting she'd take her bra off. Like I'd see her before the meeting dressed professionally, and afterwards she'd have it back on again, but she was clearly braless coming to see me. I even spoke with HR about her conduct, and they said they'd speak with her, but it was mostly for my own protection. I found it flattering as hell and I was too naïve to see why it was a terrible idea.

"The other girl was more subtle, but she just tried to spend time with me whenever she could, even outside work. At first, I thought she was just being friendly, but one night we went together to a conference and almost hooked up. I managed to prevent anything from happening, but she made it pretty clear that night by how aggressively she was flirting with me that something could happen if I wanted it.

"One night, it was our Christmas party at one of our co-worker's houses, and everyone got pretty drunk. I was flirting with both women most of the night, and because we were in no shape to drive, people were just crashing everywhere. Bay Street was more open back then, workplace hookups happened all the time, it was a more frat boy kind of atmosphere. Somehow, I wound up sharing a bed with both girls, and I figured in my drunken state that having both of them there meant that nothing would happen. But I could tell as we were lying there, cuddled up all together, that both women were turned on. I just kind of let my hands start roaming, and before I knew it, I was fingering both of them at the same time, one on each hand. We wound up having a full-on threesome."

The group was staring at me now, hanging on my every word. Lauren in particular was open-mouthed.

"You definitely never told me that story," she accused.

"I never told a soul," I agreed. "I was convinced afterwards I was getting fired for misconduct. But nothing bad happened. We went back to work, and things got better with them. It's like we got it out of our systems and that was that.

"I'm not proud of what I did then. I was in a power relationship with both women, and it wasn't appropriate, even if they were the aggressors. I never told anyone about it until now, but I don't work at that company anymore and I've lost touch with both people. It can't really come back to haunt me. It was on me then to say no, and I should have, and I regret that I didn't. But it's my only threesome, and the day still hasn't come that it's stopped turning me on thinking about it."

"I didn't know you had it in you, Corcoran," Lauren said approvingly. "Nice work."

"Thanks, I guess," I said reluctantly. "It's hot because it's a threesome, but it's also hot because it was so wrong."

"Who's next?" Oliver said, looking at the two remaining girls.

"I want to go last," Lauren said.

"I don't know if I want to go at all," Danielle said, blushing.

"You don't have to," I reassured her.

"Like fuck she doesn't," Liam insisted. "She doesn't get to hear all the stories if she's not participating."

"You can do it," Emily reassured her. "Just tell your virginity story. It's cute."

"That's not the hottest thing that's ever happened to me, though." Danielle blushed an even deeper shade of red. She was wearing a low-cut red top, and the crimson colour had spread to her torso, matching her clothes.

"What was?"

Danielle took a breath. "Today Sean and I saw Miguel and Alejandra fucking on the beach."

"What?!" exclaimed four people in unison.

"When? How? When you were on that walk?" Emily looked mildly jealous as Lauren stared at me, jaw agape.

Danielle recounted the entire story to the group, in detail, leaving out our mutual masturbation at the end but otherwise hitting every note. She was a strong storyteller, and my erection started coming back as she spoke. It was hot having the morning recounted to me, but even hotter hearing the story from her perspective, filtered by what she found hot about the experience.

"And his dick, oh my god. He's got a monster." Danielle held her hands out at least twelve inches apart. "It looked like one of those giant sausages you get at the Ohio State Fair. I didn't know they came that big. And she's so tiny. I have no idea how it fits inside her."

"I'll never be able to look at him the same way," Emily said lasciviously. "I already knew he was hot. Knowing he's got a horse cock too, oh my God." She had shifted to a legs-open position. All six of us were starting to look like we were feeling it. There were flushed faces and telltale bulges around the room.

"Sean, is she telling the truth?" Lauren demanded.

"That's the story," I responded. "It happened the way she told it."

"Is his dick actually that big?" Emily asked, tension in her voice.

"It was enormous," I said flatly.

"And they didn't see you?"

"Nope. We got away with it. We even walked back along the beach with them, and they didn't say anything."

"Damn, Miguel," Lauren said. "I never would have guessed. Too bad he's married. Maybe Alejandra will share."

"I think she wants all his sperm to herself," Emily giggled. "I'm pretty sure they're baby-making this trip."

"I'm supposed to follow that story, huh?" Oliver groaned.

"Keep it going!" Lauren exclaimed.

"OK, so this one goes back to my first year of college," Oliver began. "I was dating a girl named Madison and she lived in a traditional-style dorm room on campus, sharing a room with another girl. Madison had a crazy libido and always wanted to fuck, no matter where we were, and there were some nights that we'd come back to her room and find that her roommate was there. We'd make sure that Xinyi was asleep before getting it on, and we'd always try to be quiet, but we were still having sex fairly often in a room with another girl in it.

"So, one night I was hitting Madison from behind, and I happened to look over at Xinyi, and she was awake and staring at me. She immediately tried to pretend to be asleep, but I kept looking at her, and I caught her checking to see if I was still looking. So eventually she stopped pretending and just started watching us, and then I saw her hand moving under the covers."

"That's hot," Lauren approved.

"For the rest of the school year, whenever we'd have sex, I'd keep making eye contact with her roommate, and she'd get off watching us. I never touched her and hardly ever even spoke with her otherwise, but she'd sometimes flash me a boob or something while she fingered herself. I tried to time my orgasms with hers, and it was insanely hot being watched. And somehow Madison never noticed."

"Wow," I said breathily. My cock was starting to strain in my underwear a little, but with five sets of eyes watching me I was unable to adjust it to sit more comfortably.

"One more to go," Oliver said, turning to face Lauren. "Based on this afternoon, I'm expecting this to be good."

"Shut it," Lauren giggled. She took a breath. "I've got a couple stories I could tell..." she paused for effect. "But I'm going to tell the story of my first time with a girl."

"Nice," Liam approved.

"I was a camp counsellor the summer between high school and university," Lauren began. "I was in charge of a bunkhouse full of girls between 13 and 15, and it was every bit as terrible as that sounds. But the counsellors I worked with were awesome, boys and girls both, and we'd sneak out at nights sometimes after the girls were asleep to drink or smoke weed. We all should have been fired, but the idiots running the place never caught on.

"There was a girl there, Rebecca, one of the head counsellors, that was a little older still, I think she was three or four years older than I was. She was an out lesbian, spiky hair, wore masculine clothes, piercings, sort of had a Suicide Girl vibe to her. I had such a massive crush on her. I'd had boyfriends in high school, but I'd never had a chance to explore my bisexuality. And, I mean, I was fine with boys at that point, I could string a boy along with the best of them, wrap them around my little finger. But I was still a tongue-tied flustered mess trying to talk to a girl I liked."

"I can't picture that at all," I interjected.

"I got better at it with experience. But yeah, so one night we were hanging out around a campfire at like two o'clock in the morning, it was one of those hot summer nights where the air just sits oppressively on you like a weight. All the rest of the girls had gone to bed, it was just me and Rebecca finishing off the bottle of rum we'd acquired, and we were so hot that she suggested skinny-dipping. Of course, I was going to say yes. So, we headed for the lake and stripped nude, I can still picture her tiny body, she had these cute little tits with both nipples pierced. I'd never seen that before. We swam for a bit, and I was flustered. I was so turned on."

As Lauren spoke, I noticed that even though the room was collectively hanging off her every word, Lauren was telling the story directly at Emily. She had her eyes locked on, like she was trying to inject her story into the darkest parts of Emily's psyche. Emily, for her part, was staring back, entranced, mouth open, seemingly unable to move.

"We were trying to keep the noise down, just swimming, when Rebecca came up and embraced me and started kissing me. We made out in the water for a few minutes, but that lake was still cold in the middle of summer, so we got out and dried off. I was still so flustered that I tried to go back to my cabin, but she just took me by the hand and led me to a quiet spot in the woods, sat me down on my towel, and went to town on me. I needed someone to teach me how to make love to a woman, and she taught me everything I needed to know in one night. I still use some of the tricks I picked up from her when I fuck girls." She smiled evilly, and finally broke her gaze with Emily, who sat there, looking for all the world like her mind had just exploded.

"Um... teach me her tricks too," Liam stammered.

"I can't, darling, you don't have a vagina that I show you on." She winked.

The room fell silent. I looked around, seeing signs of arousal in all five people. Both the boys were sitting in slightly awkward positions that I thought were designed to hide erections, while the two girls on the bed were both sitting in unladylike open-legged positions. Only Lauren seemed nonchalant, but her dilated pupils and her smirk gave her away.

"Another game?" I suggested.

"Who won this one?" Liam pointed out.

"We all won." Lauren mimicked jerking off an invisible dick, to laughter.

"We can't do the same again," Danielle pointed out. "If these were the hottest stories we have to share, then no one wants to hear the second-hottest."

"True," Emily agreed. "Anyone know any other hot games?"

"How about Last Time You?" I suggested.

"What's that?" Oliver asked.

"Basically, we each pick a sexual thing, and then we all have to reveal when the last time was that we did that thing," I explained. "So, if the category is last time you had sex, for example, we all have to say when it was, and then whoever had sex most recently then has to take a drink."

"My drink's empty" Danielle said. Liam, Lauren and Oliver all held up empty glasses as well.

"Oooh! How about Strip Last Time You!," Lauren yelped. Liam and Oliver both cheered. "The boys are in. Sean?"

"I'm down."

"Ladies?"

"Sure, why not," Danielle said at last. Emily still appeared overloaded a little bit, but she nodded.

"We've got to get even for clothing," Lauren continued. "Boys, you're all wearing tops, bottoms and underwear?"

I nodded, and Liam and Oliver did likewise.

"I've got the same three things on as well, this halter top has enough support that I can wear it without a bra. Ladies?"

"I've got four things on," Emily stammered. "Top, shorts, bra and panties."

"Me too," Danielle added.

"Will we allow these lovely ladies a little handicap?" Lauren had completely taken charge of the room. "I'll take everyone's silence as affirmative. And one more rule, anything you say has to be possible for both sexes. No last time you were on your period, or last time you had a boner."

"Agreed," said Liam. The rest of the room nodded.

"So, I guess the obvious one first, last time you had sex?" I began.

"This isn't fair to those of us with boyfriends," Danielle pouted.

"Six months ago, in Vancouver," Lauren lied.

"Wait, what?" Danielle was confused. "I thought you said you just got out of a relationship."

"It was long distance," Lauren explained. "I've had Skype sex since then, but not the real thing."

"About seven months ago," I added, changing the subject so she wouldn't have to explain further. I caught Lauren's eye - we wordlessly nodded at each other about keeping our previous night's tryst quiet.

"Two weeks ago," Liam said. "It was a random hookup."

"I've got a friend with benefits," Oliver said. "I last saw her about a week ago."

Emily and Danielle turned to face each other. "I knew it would come down to us," Emily said. "We need to say at the same time so there's no cheating."

"I'll count you down," I offered. "1, 2, 3!"

"The night before we left!" Danielle shouted.

"The morning we left!" Emily shouted at the same time.

"You did it that morning?" Danielle said incredulously. "We were at the airport by 6 AM!"

Emily blushed. "Milos asked me to wake up him to say goodbye." She quickly peeled off her top, as if getting it over with. Her tiny tits were covered by a light grey cotton casual bra that left everything to the imagination, not allowing much in the way of a visual.

"Shall we say that the person to strip makes the next suggestion?" Lauren asked.

"Good idea!" Emily said. "That way you know you shouldn't have to strip twice in a row. I'll say last time you masturbated. For me it was at least a couple weeks ago, and I'm sure that's not the most recent. I've had a lot of sex lately."

Danielle turned a shade of red somewhere between tomato and fire engine. I looked at her, trying to catch her eye. I wasn't thrilled with the idea of lying two questions in a row while playing a game based on truthfulness and the honour system, but I also wasn't going to give our secret away when she'd specifically asked me not to.

"For me it was the first night of the cruise," I said. "I did it in the shower."

"I did it while you were in the shower that night too!" Lauren exclaimed knowingly.

"You should have done it together!" Liam offered. Lauren punched him in the arm. "Ow!"

Danielle looked up at me, meanwhile, silently saying thanks with her eyes.

"Why is Danielle blushing so much?" Oliver noticed. "You think you're going to lose?"

"I did it an hour ago," Danielle said quietly.

"What?!" Emily was shocked. "When? We've been together all day since getting back on board!"

"You went up to the Lido to get a snack..." Danielle mumbled, mortified.

"I was only gone five minutes!" Emily exclaimed.

"Five minutes was all I needed." She paused. ""It was hot watching Miguel and Alejandra. Everyone needs to stop staring at me. I know I lost this round, boys. Make it official."

"I did it the night before we left," Liam said.

"I did it in the shower yesterday morning," Oliver added.

"Dude, seriously? I shower in there too." Liam was grossed out.

"Grow up, man. These girls wound me up on the dance floor." Oliver shifted.

Danielle sighed, and stripped her red top off. She was wearing a black plunge bra underneath, feminine, well-fitting, and also not particularly revealing.

"This works, now we're all even anyway," Oliver observed. "Danielle, your pick."

"I'm going to go with last time you watched porn, because I don't really watch it," Danielle said. "I haven't seen it for a couple of years at least."

I thought back. "I don't remember exactly, but probably the day before the day before we left."

"Same," Oliver and Lauren said at the same time.

"The night right before leaving," Liam said, dejected. "Emily probably doesn't watch it either."

It was Emily's turn to blush. "Two weeks ago."

"Really? I didn't know that about you." Danielle exclaimed. "No judgment, though."

Liam pulled his top off, to general approval from the ladies in the room. I noticed he'd gotten sunburned on the beach, but his washboard stomach suddenly made me slightly self-conscious about my skinny physique.

"OK, if it's my turn to pick, I'm hoping to see one of the girls lose something..."

Lauren sighed.

"...So, I'm going to say last same-sex sexual experience." He smiled a Cheshire cat smile at Lauren. "I've never had one."

"Never," I said.

"Never," Emily said.

"Never," Danielle said.

"Six months ago," Lauren said, already standing to pull her leggings down.

"In high school," Oliver said.

Liam stared. "What the fuck, bro?"

Oliver shrugged. "Stuff happens at sleepovers sometimes. I'm not saying more than that."

Lauren high-fived him. "Good on you, man. Too many guys are prudes about that sort of thing."

Liam shook his head as Lauren rolled her leggings off. She had a black thong underneath, and did a twirl, showing off her butt to the room, lingering for a moment towards the girls on the bed before sitting again.

Lauren turned towards Emily. "My turn. I pick 'last time you performed oral sex on someone.'"

"That's not fair," Emily said. "You know I'm the last person in the room to have had full-on sex."

"That doesn't mean you blew Milos last time you fucked him," Lauren pointed out.

"Yeah, but I did," Emily said. "I lost this round, right? Anyone else want to chime in?"

We sat silently.

Emily grunted in annoyance, then reached behind her back, unclasped her bra, and carefully lowered it while cupping her breasts with her hands. "No one's getting a show until I lose again, because that's cheating."