Yachting with My Sister Pt. 02

Welcome back for part 2. Everyone in the story is over 18.

Yachting with My Sister - Part 2

When they arrived in Maureen's luxury stateroom, Maureen sat in the middle of the bed leaning back on the headboard with her legs parted.

"Julie, you sit here between my legs facing the bed." Julie climbed up on the bed as she had been instructed. "Leeland, on your back. Head between your sister's legs." Lee also followed her instructions and smiled up at his sister. The top of his head was almost touching her pussy. "Julie, my crew is going to have a little fun with your brother. I think you'll enjoy this," Maureen told her, as she reached between Julie's legs and gently stroked her pussy.

Diljan, Lori, and Olga walked in and stood at the foot of the bed.

"Leeland, bring your legs up for Julie to hold," Maureen told him.

He raised his legs and Julie grabbed the calves. Lee's big hard cock was now pointed toward his sister. Lori moved up between his legs and began rimming him. Julie pulled her brother's legs up a little so she could get a better view.

After a few minutes, Diljan began kissing, licking, and sucking his balls as Lori continued teasing his asshole. Several minutes passed before Olga joined the others and began working on his cock. Lee, being in the position he was in, had little ability to move. Julie was soaked, both from watching and from being fingered by Maureen.

"My crew and I are very oral. Until about a year ago we only serviced each other. Never anyone else. Lori met Leeland one day when she was returning from shopping. He helped her with what she was carrying. Other than occasionally having a man on board to do some maintenance, he was our first male guest.

"Just for fun, my crew seduced him while I was away on business. When I returned, I watched the video from my security system. I record everything. Even what we've done with you today. I'll be sure to make a copy for you. Leeland impressed me, and I realized that they were missing having a man around. Besides his wonderfully large cock, he's intelligent, fun to be around, very caring, and a remarkable lover. That's how we began our relationship.

"As it stood until your arrival, Leeland had essentially free use privileges with my crew. At least when they're off duty. To us, your brother is the cherry on top of an already delicious dessert. What we provide him is fairly obvious.

"Now that you're here, you'll be his lover and he yours. I wouldn't want to do anything to interfere with that. The love you share is obvious. If you and Leeland decide to join us on the Liberty, you'll share a stateroom. You'll also live and travel with us. You will be free to leave whenever you choose. My crew will also be available, both in service and sexually to both of you. Their duties on ship, however, must come first.

"If you prefer a monogamous relationship with Leeland, you can have that too. Neither of you will be required to participate in our sexual antics. You'll be welcome to join in at any time. If you choose monogamy, we'll all respect that."

"Maureen, what do you get out of us being onboard?" Julie asked.

"Family, true companionship, and friends; things that my money can't buy."

"People need to have a purpose," Julie said.

"Leeland has his writing. You, my dear, have told several people that you'd love to be a career student."

"Um, how do you know that?" Julie asked.

"I have to be careful regarding those I associate with...hold on. Leeland is going to cum."

Olga took his cock out of her mouth and began stroking him. His cock was aimed toward Julie. She leaned forward, opening her mouth. Some went into her mouth, but most was on her face and chest. Julie released her brother's legs so he could put them down. All three of the crew moved up and began licking the cum from her. Then each, in turn, kissed her, sharing what they had collected before sitting up on the bed.

"Where were we?" Maureen began. "Oh yes, security. I have to be careful who I associate with for security reasons. I run extensive background checks on my associates, you and Leeland included. Julie, I know more about your last four years than Leeland does."

"Such as?"

"I'll be happy to discuss that with you in private," Maureen replied.

"Mo," Lee began. "Let's say while in the Mediterranean, Julie and I want to take a week and go to Paris. How would that work?"

"Diljan, would you care to answer that?" Maureen asked.

"You'll be residents of the Liberty. As Captain, it's my responsibility to know your whereabouts and provide for your safety. We would work with you to book all your reservations to be sure you're secure. I would need to be able to reach you 24/7. If your plans change, I need to be made aware of it. Every member of the crew, in addition to our other training, is a well-trained bodyguard."

"We're badasses too," Olga said, grinning.

"It would be my preference, depending on where we are, that one or two of the crew travel with you," Diljan said.

"And if we prefer they don't?" Julie asked.

"I'll have you tailed by someone you don't know. Just like Lori was tailed to the grocery store yesterday."

"How much risk do we actually have?" Lee asked.

"Probably no more than any other tourist. Maureen would be the primary target. We want everyone safe. Once they're a resident, no one leaves the Liberty alone."

"Diljan, is there risk even on the water?" Lee asked.

Diljan looked at Maureen. She nodded.

"About three miles from us is a cruiser. Onboard are at least four armed guards. With the push of a button, a text message, or a call, they'll be here, fully armed, in five minutes. In addition, there is a helicopter, also full of armed guards, ten minutes away, and prepared for most any situation."

"You take security seriously," Lee said.

"Very seriously. There's more security than what I've told you about, but, at present, you don't need to know that."

"Let us talk this over. We'll get back to you on it," Lee said.

"No problem," Maureen replied. "Julie, ready to settle your gambling debt?"

"You're going to hold me to that, huh?"

"Every inch of it."

"Let's go."

"Everyone off the bed," Maureen directed.

After they were all up, Lori fitted Maureen with a strap-on. It was big, but smaller than Lee. Olga fitted Diljan with one that had even less girth. Maureen stretched out on her back about eighteen inches from the headboard. Lori lubed up the dildo.

"Ready when you are. Face me, cowgirl," Maureen said, smiling.

Julie straddled her and slowly lowered herself on to the dildo, then began moving up and down on it.

"How is it for size?" Lori asked.

"Good. Not as tight as with Lee," Julie replied.

After several minutes Diljan got up behind her. Olga put a single lubed finger in Julie's ass.

"Easy there. I haven't done this much," Julie told her.

Over several minutes time, Olga had worked three fingers inside. Signaling she was ready; Julie lay forward onto Maureen. Olga lubed the dildo then guided it to Julie's asshole. Diljan pushed in about an inch then stopped. Julie began moving up and down on Maureen and more of the dildo in her ass began disappearing. Both dildos were entering at the same time.

"Wow! Talk about being filled up," Julie said.

Lee had been standing there watching. "How does it feel?" he asked.

"It's starting to feel really good." She picked up her pace a little. "Lee, I'm ready for you."

Lee got on the bed in front of Maureen and Julie's heads. Julie took her brother's cock into her mouth and worked her way down on it. Maureen and Diljan picked up their thrusting. Julie was soon moaning and pounding herself on all three.

"Your little sister is being fucked in all her holes, Leeland. Doesn't she look happy?"

Julie did seem to be really enjoying herself. Lee grabbed her hair and held her head as he fucked her mouth. Julie was moaning and soon began flushing. She grunted with each thrust, then with a single long, loud moan, she came. Julie's body stiffened, her legs shook, and she drove herself onto the rubber cocks. Lee erupted at the sight. His first shot was in his sister's mouth. The remainder covered her face. Julie leaned down and kissed Maureen and both their faces were cum covered. Diljan slowed, then pulled out. Lori immediately began tonguing Julie's gaping ass.

Maureen pushed the exhausted Julie off to the side and Olga licked both faces clean. Everyone laid on the bed relaxing afterward.

"I've never cum so much or so hard in my life. You got this on video?" Julie asked.

"I got it all," Maureen assured her. "Diljan, let Artemus know we'll stay here tonight and return tomorrow."

"Yes, ma'am."

"Is the jacuzzi ready?" Maureen asked.

"All set," Olga replied.

"I suspect Julie's bottom would enjoy a soak in the warm water," Maureen said.

"All of me could use that."

"Let's setup an hors d'oeuvres tray and some good wine then relax for the rest of the day," Maureen suggested.

"If we're staying out here tonight, I'm going to need to borrow something to wear," Julie told them.

Everyone looked at her and laughed. "You won't need clothes until the trip back tomorrow," Maureen advised.

"Are we having more sex? I'm wasted," Julie asked.

"I, for one, am not. Julie, if you want more there are at least four people here who would be happy to accommodate you."

"No, no. I need rest," Julie replied.

"Suit yourself," Maureen said, smiling. "Leeland, you and Julie are in stateroom two. Feel free to freshen up and relax for a little while. We'll meet up at the jacuzzi in about an hour."

Lee led his sister to their stateroom. They immediately went into the large shower. Standing together under the warm shower they looked in each other's eyes. They held each other for a long time as they stood there, then finally stepped apart and washed each other.

"God, what an amazing day. I lived most of my fantasies in one day."

"Most? What did we miss?" her brother asked.

"Let's see. You were my biggest. We did a threesome plus. I made love with four beautiful women. I swapped cum. It wasn't a fantasy, but I got airtight and a gangbang of sorts. And I watched you get a blowjob."

"That's what we did. What fantasies are left?"

"A happy ending massage, for one."

"And?"

"I'd like to try bondage, giving and receiving."

"Light or heavy bondage?"

"Not the pain stuff. Just being used, I guess. Oh, and with an audience. I really like being watched."

"I noticed that. I'll talk to Maureen," he said.

"Not today. I really need to rest my parts for a day or two."

"With everything else on this ship, I'd wager there's a massage table," Lee told her.

"Not tonight. Oh, and in a car."

"You lost me," he said.

"I've never made love in a car."

"That's an easy fix," he chuckled.

*****

They met up with the others near the jacuzzi a while later. The spread for the hors d'oeuvre tray was impressive. The group watched the sunset as they enjoyed the warm water.

"How's your bottom," Diljan asked Julie.

"Not bad. I can tell it's been used, but it doesn't hurt."

"Want me to kiss it?" Lori asked, grinning.

"Uh, no. Thanks. I'm resting it for the night."

"Maureen, did you know Julie has never had a happy ending massage?"

Maureen smiled. "I highly recommend the Olga special."

Julie turned to Olga. "What's the Olga special?"

"I begin by joining you in a nice warm bath to get us all clean. Then Lori and I give a four-hand full body massage. To finish up, I give you a nice long Nuru or Yoni massage," Olga replied.

"What are those?"

"Nuru is slippery body to body. Yoni is a pussy massage. Both are wonderful."

"I'll second that," Maureen smiled.

"Just let me know when," Olga offered.

"I will. Count on it," Julie replied.

"I can also teach you both Lingam and Yoni massages. It's a wonderful skill to have."

"Is Lingam a penis massage?" Julie asked.

"It is."

"Sounds like a must do," Lee chuckled.

"Whose dick did you want to massage, Leeland? Maybe I can hook you up."

"I meant learning the Yoni. The only dick I massage is my own. Thank you," he replied, smiling.

"Lee, that's like having five nice cars available then walking across the country," Diljan told him.

"Fortunately, I haven't felt the need to do that in a while, thanks to all of you."

"How about you, Julie? Have you had to run things by hand recently?" Maureen asked.

Julie blushed then smiled. "As a matter of fact, I had to do that last night. My brother got me all hot and bothered, then sent me to bed alone."

"Lee! Why would you do something so selfish?" Lori asked.

"Gimme a break. Today was the first time we ever touched each other sexually."

"I never had a brother, so I'm asking from ignorance. Why? You both wanted to," Maureen asked.

"Society and religion forbid it. We were raised to believe it was wrong," he said.

"Fuck society! That's why I live on the Liberty. I can make my own laws."

"You can afford to do that. Most of us don't have that kind of freedom," Julie said. "How about the rest of you? What were you taught?"

"Same as you," Olga replied.

"Same here," Diljan added.

"I don't have a brother, but I had an uncle that was my lover in college," Lori threw in.

"None of you are bothered by Julie and me?"

Everyone shook their head. "If two consenting adults are happy with it, who am I to judge?" Diljan asked. "Sex is wonderful. Enjoy it."

"I'll drink to that," Maureen said, raising her glass."

Everyone touched glasses and took a sip. They stayed out until well after dark. Maureen and Lori left together and a short time later, Olga and Diljan left holding hands.

"Tired?" Lee asked his sister.

"Yes, but I don't want the day to end."

"No, but it will anyway. Let's spend the rest of it in bed holding each other."

She smiled and kissed him. Lee and Julie went to their stateroom. Laying in each other's arms they were asleep quickly.

*****

When Julie woke, Lee wasn't in their stateroom. She showered, then put on a little makeup. She looked through her small bag for something to wear.

"The hell with it," she said, and left the room nude.

"Good morning. There's coffee at the bar. Lee and Maureen are topside at the bow," Diljan told her.

"Good morning. Thanks," she replied.

After getting a cup of coffee, she joined them. Lee and Maureen were on a large mat facing the sun. Lee wore his board shorts and Maureen was dressed exactly like Julie. She sat facing them.

"I'm glad you're finally up. I was afraid we were going to have to reschedule your massage this morning," Maureen said, smiling.

"An Olga massage?" Julie asked.

"Olga and Lori both at first," she replied. Maureen stood. "I have some business to deal with, if you'll excuse me," she said, walking toward the main ship.

"I was afraid I was underdressed," Julie told her brother.

"I don't think that's possible on the Liberty."

"Can I ask you something?"

"Anything," Lee replied.

"I don't remember Maureen and you doing anything together yesterday."

"Jules, Maureen likes women. She and I have never had sex."

"She said that if I won the bet, she'd suck you."

"Maureen knew there was no way she was going to lose that bet."

"Do you want to cruise with her?" Julie asked.

"You and I need to talk about that. How about we think about it for a few days first?"

"I think that's a good idea. It is tempting."

"Yes, it is," he replied.

"What about your boat?"

"Maureen said she'll have it stored in dry dock."

Lori walked up to them, wearing a cutoff t-shirt. Her small red patch was clearly visible. "Breakfast has been set up on the aft deck," she said.

"On our way," Lee said, helping his sister up.

They went aft and had breakfast with everyone except Maureen. Diljan wore a top and skirt like Lori and Olga had worn the day before.

"Why are you all dressed up?" Julie asked.

"I'm working. Someone has to keep this thing afloat," she replied. Diljan's phone rang. "Yes, ma'am?" She listened for about two minutes before ending the call. "Maureen sends her apologies. She has to leave for business for a couple of days, and she asked me to remind you about her offer."

"I do hope you accept," Lori said.

"Me too," Olga added.

Diljan was nodding in agreement. Everyone pitched in to help clear the table. When completed, Olga and Lori led Julie away.

"Join me clearing the helipad?" Lee hesitated. "She'll be fine," Diljan assured him.

"Sure," Lee replied.

They went forward. Lee watched in awe as Diljan pushed a few buttons and the foredeck split then turned upside down revealing the pad for the helicopter. Maureen walked up to them wearing a gray business suit.

"Leeland, I have a question."

"Sure."

"Would I be overstepping my boundaries if I invited Julie to have dinner with me in a few days?" Maureen asked. Lee grinned at her. "What?"

"Yes, Mo. Julie is a big girl and will make her own decisions. Have her home at a reasonable hour," he chuckled.

"Ten am, or so?"

"I thought it was a dinner date."

"We'll be having dinner."

"That's between you and Julie. You have my blessing."

"Damn, I can't believe I just asked for your permission. That's a first for me."

"You did very well for a first timer. Thank you for caring enough to ask."

"You're welcome, I think. Is Julie with Olga and Lori?"

"Yes, ma'am," Diljan replied.

"She's going to love this, Lee. It's a wonderful experience. You'll have to get the Langham massage."

They heard the helicopter off in the distance and stepped inside to avoid the upcoming wind. After it landed, Maureen walked to it and climbed inside. It was in the air again in seconds.

"It's just us now, and I'm on duty. Want to help me on the bridge?" Diljan asked.

"I'd love to," he replied, offering his arm.

Olga took Julie to Maureen's stateroom and began running water in the tub. She added an oil and some sort of white powder as it filled.

"I'm going to be bathing you from the neck down. Just close your eyes, relax, and keep your hands to yourself. Lori is setting up the massage area next door. After the bath, we'll join her there. When that's done, we'll move to a mat, and I'll begin your Yoni massage. Any questions?" Olga asked.

"Do I get to participate in the massage?" Julie asked.

"No. This is about giving you pleasure and relaxation, not having sex."

"I'm getting a non-sexual pussy massage?" Julie asked, raising her brow.

"Sort of," Olga replied, stepping into the tub.

Once seated, she invited Julie to join her. Julie sat between Olga's outstretched legs. Olga began the bare-handed bath at Julie's neck and worked her way down the back.

"Why is my skin tingling?" Julie asked.

"This is geisha water. I picked up the additives a few months ago in Japan. It's perfectly safe. Maureen had it evaluated before she'd let me use it," Olga replied.

The bath continued in a very loving and sensuous manner and had Julie hot quickly. Olga had Julie stand to wash the pelvic region. She took her time with it, making sure to keep Julie on edge.

Lori walked into the room and helped Julie out of the tub then dried her with a very soft and fluffy towel. Both women walked her to the massage table and helped her onto her stomach. All three of the beautiful women were nude.

Lori began by working on Julie's scalp as Olga began on her shoulders. Both moved slowly as they worked. Julie had been massaged before but had never experienced this kind of loving attention.

Lori stepped to the side opposite Olga, and each began working on Julie's hands and arms. Julie was like putty in their hands as they continued onto her upper back.

"This is wonderful," she said.

"Shhhh," Olga whispered. "Just relax."

With four hands massaging her, Julie really had little choice. The hands moved to her low back and down as far as her butt crack, but not to the buttocks. After a long time both women stepped to the foot of the bed and began massaging Julie's feet. She felt her legs being moved apart as they worked their way up.