Mid-Life Oasis Ch. 02

I guess even paradise has its little problems.

I decided that, until we had the gangbang, I would need to be more dominant. We were on a trajectory to be in-love too soon and that was a potential problem. She wanted discipline and I figured this was a good time to push that envelope a bit and to hopefully keep love on the back burner.

I decided to spend more time on the details of her fantasy and see what that might lead to.

"Jill, tell me more about your fantasy. How do you envision it playing out. How do the men treat you?"

She didn't hesitate.

"They treat me like a slut, Master. They treat me like their property."

"And, that is what you want?"

"Yes, Master."

"Jill, tell me again why do want to be treated like a slut. Be totally honest."

"Because I am a slut, Master. I may act like a good girl, but deep down inside, I am a dirty girl."

"Then, why do you act like a good girl?"

"Because being a slut is no way to live, Master. A woman is not accepted unless she behaves like a lady. I want a career and I need to maintain my reputation. I can't have pictures of me on the net or whatever and that's what happens to girls who are reckless and who give it out all the time."

"So, if you could get away with it, you would be a slut all the time?"

"I don't know. Maybe. I do like being a good girl too. Maybe I'm just sick of all the men that I'm with treating me like a goddess or whatever, when what I really want is to be fucked. I love sex, Master, and I love getting fucked. Every guy I have been with except for Kyle, has wanted me for a Wife. Guys fall in love with me too easily and guys don't like to fuck the shit out of the love of their life. They want to protect me and respect me. I don't want their respect and protection if that means a spineless sex life. Men are too linear when it comes to love and sex. At least that's the way it seems to me. It's what I've experienced so far."

This was one unique woman.

"Wow. That's quite enlightening. In your fantasy, what are the men saying as they fuck you?"

"They call me dirty names like whore and slut. They tell me that I'm nothing but a cum bucket and that they are going to use me until they are satisfied. I really get off on it too. I'm always on the verge of the biggest climax ever when I wake up."

"Jill, did you have the dream last night?"

"Yes, Master."

"Jill, the next time you wake up after having the dream, I want you to tell me every detail that you can remember. Wake me up if you have to, Ok?"

"Yes, Master."

"Ok then. It's time for you to get to work. Get your chores done and when you are satisfied with your work, I want you to work on your tan until it's time to cook dinner. I'll be in my study."

"Yes, Master."

She cleaned the house with her usual zeal and cooked a great dinner that night. We had more intense sex before bed and she came like crazy. When I awoke the next morning, Jill was awake and looking at me with her big blue eyes. I felt blood rushing to my cock.

Jill told me that she'd just had the dream again. I told her to recount the most vivid part or parts.

"Master, after they finish the card game, they penetrate me in both my holes at once and it really hurts."

"Is that pain part of the dream Jill or is part of the fantasy?"

"Both, Master."

"You want to be in pain?"

"Yes. Well, sort of."

"Please explain, Jill."

"It's sort of like you taking my ass. There's pain at first, but the pain is something that I overcome. A few minutes later, the pain has turned to intense pleasure and as the men are calling me their whore and their cumslut, I begin to shake and as I am about to explode in orgasm, my eyes fly open and I am unsatisfied. That was just a few minutes ago, Master."

"You always mention your failure to finish. This has to be a big key. Part of you fantasy is just to finish? To find out how that orgasm feels in real life?"

"Yes, Master. Very much so."

"Ok, Jill. I think we are getting somewhere now. The only issue I see is that if the men are only using you for their pleasure, will you get that big climax? I think we might have to blur that line. At least at the end we will. Does that make sense, Jill?"

"Yes, Master."

"Good girl. Why don't you go fix breakfast and then get to work on your chores. There's a shopping list on the kitchen table. Please get to the store today."

"Yes, Master."

While Jill shopped that afternoon, I made some on-line purchases. I got her a pair of Ben Wa Balls to help her enjoy her cleaning a little more.

I also bought some restraints just in case I ended up wanting some during our trip. They were padded, but they were steel on the inside, so I knew they'd get the job done if I needed them. The thought of chaining Jill somewhere on-board so the guys could just use her at their whim was pretty hot and I knew she'd love it. I also bought a long chain and collar for her so we could move her around in the kind of demeaning fashion that she craved. The last two things I bought were a blindfold and a ball gag.

I went down to the marina and talked to a few candidates for captaining my ship for the big weekend. I met a guy named Bill and I told him that we had a bachelor party scenario and that we'd be banging a hot submissive for about 48 hours. We needed a guy who could handle the ship and also use proper discretion once the weekend was over. Bill told me that he was only here for another three weeks and that he was moving back to San Diego after that. He said that he'd be fine with the bachelor thing and that he'd keep everything he saw to himself.

I told him that he was hired and that the gig would pay five times his normal rate. He liked that a lot. We had our Skipper.

After I left the marina, I hit the butcher shop and put in an advance order for a weekend's worth of steak, chops, sausage and plenty of marinated chicken tenders. I kept the boat well stocked with booze, but I went out and bought ten cases of various beers and a case of wine and champagne too. Better safe than sorry.

I also placed an order for fresh breads and produce to be delivered the day we left and the stage was all set in terms of prep. Everything we needed would be there and Jill would be cooking when she wasn't satisfying us. She was going to be a slave for five men and she was going to love it. I was determined to bring Jill's dreams to life for her.

I just hoped that my dreams weren't squashed in the process.

To be continued...