Circle

During the Age of Piracy, one pirate ship was the most feared. For two decades, the pirate ship "Wicked Pussycat", with an all-female crew led by the infamous Captain Blackbreast, was the scourge of the seven seas. Many governments and private companies sent ships out to capture the fierce captain and her crew, but none ever succeeded. Then, abruptly, the ship and its crew disappeared.

What had happened? Was the ship sunk with all hands in a sudden storm? Were they captured and killed by other pirates?

Nope, something much more mundane. After twenty years of piracy, with the captain and crew now in their forties, the Wicked Pussycat sailed to a hidden cove in Jamaica, where the captain and her crew were originally from. They had been sold together as slaves, risen up during the voyage and killed their enslavers, altered the ship for speed and storage, changed its name and become a band of pirates. After twenty years, it was time to retire. They unloaded all their treasure, divided it equally among themselves, disassembled and sunk the ship, and went their separate ways, each of them with enough money to live three more lifetimes.

For the most part, they blended back in and lived quiet lives. Captain Blackbreast herself, using her real name -- Serena Richards -- opened a small bar on the main commercial drag (she lived in the room behind it, part of the same building.) Serena's Bar didn't stand out as anything special: they served the usual types of alcohol and a bit of solid food. Some of Serena's old pirate companions would sometimes help out as bartenders or cooks. When the last customer of the evening was particularly attractive, Serena -- who had hit menopause the year before retiring as a pirate -- would lock the bar up early and take that customer (whether male of female) back to her quarters for some fun, if the customer was willing. Serena, despite being in her mid-forties, was still quite the looker. Her dark skin, brown eyes, black shoulder-length hair and toned body drew attention, as did her D-cup breasts that, while she was working, pushed up against her shirt.

One night, the last customer of the evening was a handsome white guy named Tom. He was a bit younger than Serena, in his mid-to-late thirties. He had short brown hair, brown eyes, and a muscular build, and he was several inches taller than her. She asked if he wanted to join her in her quarters, he accepted, and she closed the bar for the night. When they undressed, Serena noticed a scar on his flank.

"How'd you get the scar?"

"About 10 years ago, I was part of the crew on a ship hired by the British government to locate and capture Captain Blackbreast and her band of pirates. We had no trouble finding the Wicked Pussycat -- or rather, it found us. One foggy day, a ship suddenly loomed up next to us and boarded us. We fought hard, but Captain Blackbreast and her crew subdued all of us, tied us up, removed the treasure and valuables from our ship, then towed us to a nearby small island. There, they took down our sail, slashed a B in it, boarded the Wicked Pussycat, and sailed off. It took a couple of hours to free ourselves, and then we needed to repair the sail and put it back on the mast. By the time that was done, the Wicked Pussycat was long gone."

"So you got the wound in the fight. What would you have done if you had won the combat and captured the captain and her band?"

"I understand the captain was a gorgeous woman. I'd have stripped her and had some fun with her before putting her in captivity."

"Okay, now I'm curious. Pretend I'm the captain and you've captured me and stripped me. Do whatever you would have done to her, but obviously, don't hurt me."

"All right, Serena."

Tom strode over to her and wrapped his arms around Serena, giving her a kiss that was gentle for an instant, then became forceful. He pried her mouth open and invaded it with his tongue. She eventually responded in kind, after a moment of shock.

Tom broke off the kiss and began moving his lips down towards Serena's chest. He kissed through her considerable cleavage, then groped her breasts. He then took one of her nipples into her mouth, flickering his tongue over it. Serena's body shivered and she let out a soft moan. Tom shifted his mouth to her other nipple, then repeated the procedure. Serena's arms instinctively secured his head in place. Tom continued to suckle on her plump breasts while wrapping his arms around her and giving her firm, muscular ass a big squeeze. Serena let out an "eep!" sound, caught by surprise, but the feeling of Tom's mouth on her breasts soon had her making gentle moans again.

Tom lifted Serena in the air and carried her to the bed, where he set her face down and ass up. He gave each of her butt cheeks a light spank, then spread her legs apart. He ran his fingers along her slit, going back and forth a few times, then started using his tongue. Serena quivered as he teased her, licking up a few of her juices that were starting to leak. He then stuck his tongue all the way inside her and began tongue-fucking her with vigor. Serena gasped as he groped her ass and spread her legs further open. He swallowed down her flowing honey, continuing to lick inside her as she got close. His tongue began moving in little circles, and Serena was pushed over the edge. A gush of her love-juice covered Tom's face.

Tom then grabbed her and rotated her body so she was facing him. "Open your mouth, slut, and get me ready."

Serena obediently opened her mouth, and Tom stuck his half-hard dick into it. "Suck on it. Get it nice and wet."

Serena began bobbing her head back and forth, licking along the side of Tom's shaft. It quickly stiffened fully. She began slurping on it with more intensity. Tom put his hands on the sides of her head and began face-fucking her. He would thrust into her mouth and Serena's tongue would lash all the way to the base of his cock. Tom began slamming deeper in, the tip of his rod touching Serena's throat. She sealed her lips around his prick and opened her throat, letting him slide in a bit. Tom felt the cum building up in his balls as Serena gave him the first deep-throating he'd ever had. He pried open her mouth and removed his dick.

"Good girl. Now lie on your back with your legs spread."

Serena did so, and Tom positioned himself between her legs. He then slid his cock into her wet pussy. Serena quivered as Tom began thrusting, ramming his cock deep into her and then pulling out until just the head of cock was in her. Tom wrapped his arms around Serena and took a firm grip on her butt as he pistoned his hips. Serena began moaning lustfully as her orgasm approached. Tom slammed even deeper into her, and Serena's entire body shook as the wave of pleasure surged through her. Her pussy muscles clamped on Tom's cock, momentarily trapping him. When her body relaxed, Tom continued to pound into her.

Tom dipped his head to suck on Serena's jiggling breasts as he continued to thrust. Serena had another immediate orgasm when she felt his tongue flick across her nipple. Tom didn't even slow down, continuing to slam his cock into her eager pussy. Serena's legs wrapped around his hips as she approached another quick climax. He began actively groping her butt, and that pushed her over the edge. She felt him getting close, his cock twitching inside her. After her legs unlocked, he pulled out a few seconds before his own orgasm hit and squirted his cum all over her big breasts.

He then lay next to her, and they were both quiet for a moment as they recovered. Serena was the first to speak.

"It's a good thing you lost that fight. My customers say Captain Blackbreast was resourceful and merciless. The moment you stuck your cock in her mouth, she'd have bitten down on it."

"Oh." Tom paused. "Yes, that would have been rather a mistake."

"Luckily, I'm not a merciless pirate captain, just a horny old woman who loves young hard cock and young tight pussy."

Tom eyed Serena's naked body. "You don't look old to me."

"Aren't you a charmer." Serena blew out the lamp on the bedside table, leaving the room in complete darkness. "Let's sleep." She nestled against Tom, who held her as they drifted off.

The light of the morning sun in the window woke Serena. Tom was still sleeping. Serena rolled him fully onto his back and stroked his cock enough to get it hard, then rubbed her pussy against his cock until her juices started flowing. She then lowered herself down onto him and began sliding up and down. Tom shivered a bit, and Serena idly wondered what he was dreaming about. She continued slowly sliding her pussy up and down, building a rhythm, then bounced on his cock a bit faster. Her first orgasm hit, and she clamped her jaw tight to keep from screaming lustfully. She continued her steady sliding along his cock, and a few minutes later had a second orgasm, then a third shortly thereafter. His cock was again twitching and throbbing. This time, Serena, thought, I'll get that sweet cum inside me. She began using her pussy muscles to actively milk his stiff rod. His eyes flickered open right as he began spurting into Serena. She didn't move until she drained every drop out of his balls. Then she climbed off.

"I couldn't resist," she giggled. "I told you I'm a horny old woman."

"A horny not-so-old woman," Tom replied.

"Well, I'd better get dressed and get ready to open the bar," she said. "Thanks for the hot sex."

Tom smiled at her. "It was my pleasure." Then he dressed and slipped out the back door.