by Jamie Hawke
“Our man,” Ox said, clapping Frank on the shoulder in a way that made him feel very uneasy, but he was sure the giant of a man didn’t mean.
“Get some rest, all,” Teddy said. “Tomorrow we form a plan, then make our big move.”
Everyone was walking on sunshine as they headed back, and all four of the ladies pulled their bedding into the room with Frank, setting up like it was a slumber party. He’d always wondered how those went, but there were no real pillows here for a pillow fight, so he figured it wouldn’t exactly match his old fantasies about them.
The women slept in long nightshirts, and all cuddled up with him and each other. A hand moved under the blankets, moving along his leg and then along his abs. Another was on his inner thigh, and he looked at Esmerelda on one side of him, Keisha on the other, unsure which was whose.
A yawn hit him, unexpectedly, and Esmerelda smiled sleepily. “You as exhausted as I am?”
“Not at all,” he said, trying to fight the heaviness in his eyelids. Next, he turned to Keisha and, not even considering the fact that this was the first time, kissed her, too. It was a gentle caress of the lips, nothing more, but when he lay back he noticed she was staring at him, wide-eyed.
For a moment he thought she was going to be mad at him, but then she took him by the chin, turned him to face her, and came back in for a deeper, more passionate kiss. He could taste a hint of coconut on her breath as her tongue met his, and he felt a longing to hold her, to keep this up forever, but then she pulled back, their lips lingering against each other a moment longer while she whispered, “That’s how a first kiss should be,” and then she was cuddled against him, eyes closed.
His blood was moving, his excitement threatening to wake him. But when he turned back he saw that Esmerelda was asleep too, and judging by the slow but heavy breathing, the other ladies were as well.
He lay back, eyes on the stone roof, and stared.
This was the life, wasn’t it? A pirate’s life for me, he thought and smiled, then wanted to laugh at what he must’ve looked like—a young man smiling like he’d just had his first-ever bite of cake, cuddling with four of the most stunning women he’d ever laid eyes on.
With that thought, he closed his eyes, letting sleep take him.
Dreams came, with him preparing for a college essay as Mary helped Milly try on a suit for her first day in an office job, Esmerelda behind them trying to figure out how to make scrambled eggs but burning them horribly.
He glanced around, wondering where Keisha was in this dream, and then noticed something under the table, a head bobbing up and down on his crotch. Leaning back, he closed his eyes and threw the papers from his essay into the air and watched them turn to snowflakes and float down while Keisha grinned up at him, gently pressed her lips into a kiss at the tip of his cock, saying, “That’s how a first blowjob should be.”
So not Keisha’s style, and he thought of her as so much more than that. But whatever, fuck it—this was his dream!
As if in punishment for being a pervert, the next dream saw him running away from an army of pirates, all swinging large swords that, as they got closer, turned out to actually be huge dildos. He was screaming and running, now naked, his compass going on the fritz and taking all of them through various periods in time. One moment, he was on pirate islands, the next charging across rolling green hills in a kilt, then what looked like a World War I battlefield, and finally in some futuristic land of large domes and holographic billboards.
Suffice it to say, he wasn’t sad to wake from that dream. Still, morning came too soon, especially since the first thing Frank saw when he woke was Ox’s crooked nose and thick stubble as the man leaned over, nudging him. Frank rubbed his eyes and turned to see Teddy there, purposefully staring out toward the exit.
At first Frank wondered if he was in trouble, or why Teddy had his back to him. A glance over gave him the answer though—Esmerelda, his sister, was lying there, at his side.
“With me,” Teddy said, motioning Frank to follow. “I want you on patrol so we can talk strategy.”
Frank shot up, more than ready to get back out there. He didn’t want to offend Teddy, and even more, he didn’t want Ox ogling his ladies. He wasn’t sure he liked to admit it, but he was starting to feel at home at sea, missing the openness of waters in all directions and the wind in his hair. Getting a chance to talk strategy with Teddy, however, was what excited him most. From what he’d been gathering, this man was a legend. Frank wanted to find out as much as he could, to see if he could place him in history and learn who this guy really was.
Ox had a team and ship prepared, so Teddy and Frank were able to walk right on and be ready to sail. For the first time, what with the recent victory, weapons acquired, and way it was going with the women, he was able to really look around and take in where he was in a positive light. This wasn’t merely some random dangerous situation, it was a chance to sail with real pirates—and from what he could tell, the good kind! It was a chance to see the world as it had once been, in a sense. To feel the wind on his face, the spray of the sea.
It was time to learn to understand that pirate tales weren’t merely stories, because here he was really in one. As Teddy took the wheel, Frank stood at his side, breathing it all in and watching the morning sun sparkling off of the waters. He wouldn’t give this up for anything.
Soon they were moving along, staying close to the shore in case other ships were nearby. They were on a scouting mission, and if there were signs of trouble they wouldn’t want to be caught out in the open, all alone. Staying close to the island meant less chance of being spotted by the enemy.
“We’ll need to train the men,” Teddy said. “With the weapons, I mean.”
“Of course,” Frank replied.
“I trust you’ll start immediately?”
Frank licked his lips, which had started to feel dry from the salty breeze. “Excuse me?”
“You understand how they work better than anyone else could, at least out here.”
The most Frank knew about weapons was from putting them together and what he’d seen in movies, but he supposed this man was right—having watched all of those movies and played games like Call of Duty put him ahead of the others, in this regard. As inaccurate as some of those sources might have been, he at least knew what he was getting into, which was a lot more than the pirates could say. If somehow this whole situation ever came up in a discussion with his dad, he’d have to point out that all those hours in front of the TV weren’t wasted.
“I’ll do what I can,” Frank said.
The ship kept on and they sailed in silence around the bend ahead, but still no sign of any enemy ships yet. After a few more minutes of this, Teddy gestured for Ox to take the wheel, moving aft with Frank to be able to keep an eye out while they took a moment to talk.
“What have you heard about me?” Teddy asked.
“Not much, honestly. Other than that you’re Esmerelda’s brother, and what you’ve said.”
Teddy nodded. “I’ve been known to have my dark side, especially when around the drink. Thought I’d like to warn you, in case you hear it from someone else. Even though those days are behind me, I know what I’ve done isn’t erased.”
“We all have regrets.” Frank remembered his guilt over stealing a pack of gum when he was six and the look of disappointment on his dad’s face like he’d been really let down, likely had nothing on this man. But hey, it was all relative.
“Indeed we do, lad. And Esmerelda, she’s… opened up to you?”
An image of the woman opening her legs flashed through Frank’s mind, but he guessed this wasn’t what the pirate meant. “I imagine there’s much yet to learn from her.”
“See that you know her before growing too attached, aye?” Teddy looked away at that, staring over the waters again as he added, “I’d hate for you to fall for her only to learn she wasn’t what you thought, and then you break her heart.”
“Me, break her heart?
” The idea seemed ridiculous, but Teddy had a sternness in his eyes that didn’t allow for any jokes or smiles regarding the subject.
“In a world like this, she has me to look after her, and I have her to look after me.” Teddy’s eyes moved back over to Frank, fierce, holding him in place. “We don’t have a problem if you’re going to take good care of her and the rest of your team, but I’m telling you now, as friends that we’ve become, that if I find out you have ill intentions in any way, I will not hesitate to smash your skull in. Do we have an accord?”
“Aye,” Frank said, trying to sound tough and confident.
In reality, he was quite literally shaking in his boots. He definitely had good intentions, but a realization was hitting him that maybe he’d been taking this whole thing too lightheartedly, that maybe his college-boy mind had taken over and allowed him to think too much with his cock. When he saw the ladies again, he wanted to ensure that wasn’t the case, that they’d really get to know each other, be clear that this wasn’t only about physical satisfaction.
Teddy must’ve seen something he approved of in Frank’s eyes, because he gave him a nod and a clap on the back, then said, “Strategy.”
“How’s that?”
“We now have our strategy,” Teddy said with a roaring laugh. “Close teamwork, every one of us caring about the other, learning to trust, and not keeping anything back. You see?”
“Um, not exactly.”
“Aye, but you will. It’s what separates us from the bastards of the world like the Pirate King. It’ll be his downfall.”
A whistle came from Ox, and then Teddy went rigid, staring ahead, and Frank saw why.
They’d started to round the bend of the island when sails appeared over the trees—past the next bend. It wasn’t possible whoever was on that boat could’ve spotted them in their little sloop, but there was definitely someone else on the island. Teddy cursed and signaled for Ox to guide them even closer to land.
“Keep your eyes alert,” Teddy told Frank. “They might have scouts in the jungle already, searching for us.”
“Should we get back?” Frank asked. “Warn the others?”
Teddy shook his head, moving forward to take the wheel and guide the ship to a good mooring spot. “Not until we know what we’re dealing with. If they’re getting close, we might have to take them out ourselves.”
“Kill them?” Frank asked, looking form Teddy to Ox. Three against who knows how many. It might be a challenge.
“Maybe not. If they don’t return, the Pirate King might send out more to look for ‘em.”
Frank nodded, already feeling his sword hand twitching. At least they had the upgraded rifles with them—one each, so they could cause some major damage if necessary.
For now, the trio went ashore, leaving the other two pirates to man the ship and be ready to set sail if there was any indication of the enemy vessel approaching. Frank found himself slashing through the thick jungle vegetation as he charged along with Teddy and Ox, only coming to a halt when Teddy froze, one hand in a fist.
They all knelt, creeping forward, and Teddy indicated a clearing ahead.
A pirate was there, taking a piss and staring out over the island. If he turned his head slightly to the left, he would have been looking directly at them, though the jungle provided good camouflage.
To his right, another pirate approached, laughed and made a gesture, earning himself a spray of piss as the first lunged, attacking him with his dick still out.
“At least we’re not dealing with the cream of the crop,” Teddy whispered.
“We charge in now, both o’ them are dead,” Ox pointed out, leaning forward hopefully.
“Not until we know how many are nearby,” Teddy said. “And what they might report back.”
A moment later, the first of the two pirates was kicked back and then… vanished. Straining to see what had happened, Frank moved closer, then saw a valley where the man must’ve fallen. The second pirate was peering down the valley, then his head darted up, looking in Frank’s direction, it seemed. Frank froze, but after a second, the pirate kept scanning, then quickly went back the way he came.
“If that pirate’s dead, the other might make up a story,” Teddy whispered. “Say they ran into us. Last thing we need is a search party exploring our island.”
The other two agreed, and so they worked their way down into the valley, using palm trees to keep from tumbling down, though once Frank tripped on vines and Ox had to catch him. Luckily the latter was twice his size and sure-footed, or he could’ve ended up dead on the valley floor as well.
At the bottom, they kept moving, pausing only once for piss breaks. They were just reaching the spot near where the man might have fallen when they spotted him sitting up and rubbing his head.
They all ducked again, watching from behind jungle overgrowth as the pirate stood, seemed lost for a moment, and then took off walking east.
“Keep on him,” Teddy hissed, and they all moved forward. They came up and out of the valley, watching this man struggle a few times—clearly piss drunk—and then were able to see the ship in full view.
“About fucking time,” a voice called out, and Frank dove back, hand on his sword, but Ox was there at his side, holding up a hand to wait.
Ahead, three pirates emerged, walking over to the lone one, and gestured him on. “We looked long enough and haven’t found shit. Keep looking. Isn’t likely to do nothing but waste our time.”
“Back to the ship then?” the drunk pirate asked, and one of the others shoved him toward it.
Another pulled out a knife and mimicked cutting the man’s throat from behind, but the taller of the group held him back, shaking his head as he whispered, “Not here, not yet.”
The third of this group started walking toward Frank, eyes roaming. He paused and Frank imagined having to leap out and plunge his sword into the man’s belly, but a few seconds passed and the man made no moves except to squat to take a shit.
A glance from Teddy and twitch of his lip showed he was thinking the same thing as Frank—how the fuck did they end up in what was clearly the bathroom break section of the search party’s area? They were up and starting to move back when bushes parted ahead and more voices carried through.
This time Teddy had his rifle ready, Ox as well, though he looked less comfortable with it and his hand reached twice for his sword, stopping both times.
Frank glanced around, thinking fast, and had an idea. The other pirates were moving on to his right now, but if there was a distraction over there, this approaching group might rush over. He picked up a rock and blinked, glad to see the green reticle and a line showing where he could throw it—crazy! He pulled back, prepared, and then let loose. It hit one of the pirates’ shoulders, and the man turned back, saw the approaching group and shouted at them.
As the new group emerged to show there were five of them, Frank was glad he’d made a distraction instead of trying to fight them. With five, even trying to sneak past might have been difficult. Now, however, all five were arguing with the three, and even the other one in the distance stopped to see what was going on.
Frank and his crew, however, had pushed back into the jungle, rifles at the ready in case there was trouble, but none found them. One of the pirates pulled rank and ordered them back, even drawing a pistol on the others, but it wasn’t necessary. Soon they were all stomping off through the jungle.
Teddy, Frank, and Ox kept their distance after that, but found a good viewing point and watched until the ship left. Teddy grinned and said, “Back to the ship. We’re safe for today.”
Relief flooded Frank as he worked his way back, and he was surprised to realize how tense he’d been. It was only then that it struck him how overpowered they were. But tense as he was, he hadn’t freaked out—maybe because of the rifles? Or maybe it was because he was starting to feel more like a badass pirate every day.
They quickly made their way back without a hitch, and soon were sai
ling back to check in with the others and warn them about enemy scouts.
“That was close… too close.” Teddy glanced over, his expression stern but curious, as if considering something. “I wasn’t always a pirate, you know.”
“Oh?”
He nodded. “You look at me from time to time, and I see it—scorn. A bit of excitement, maybe some jealousy… but especially when you hear the word pirate, that scorn is there in your eyes.”
“I don’t know what you’re talking about,” Frank said, heart thudding as he began to wonder where this was going.
“Relax,” Teddy said. “All I mean to say is, it takes a lifestyle… it takes big moments in one’s life to get to that lifestyle. You might have it, you might not. Either way, I’m glad our paths have come together at this moment and would be pleased to see them continue so.”
Frank nodded, then added, “It would be an honor.” After a moment of tasting the fresh ocean air and feeling the waves rock them, he asked, “So… where then? I mean, before you were a pirate, where were you? What were you doing?”
Teddy grinned the grin of a man with a life of hardships behind him. “I suppose it depends on what you call piracy. Some could argue I’m still not truly a pirate. After serving as a lieutenant under Captain Hornigold—”
“The Captain Hornigold?” Frank asked, very much aware of that pirate’s role in piracy around the Bahamian island and New Providence.
“See, that right there.” Teddy narrowed his eyes, assessing Frank. “How’s it you know of Ben?”
“Wha—what year is it?” Frank asked shakily.
His frown deepened then as he asked, “What sort of answer to my question is that, lad?”
“Just that, I understand the captain…” Frank hesitated, not sure where all this lined up, or if it even did, anymore. “Is he still a friend, or…?”