Chapter 1: You Meet the Strangest People

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Swinging, Oral Sex, Squirting, Cream Pie, .

Desc: Sex Story: Chapter 1: You Meet the Strangest People - Dorothy, from 'Happy Birthday', becomes a Cruise Director. She has lots of fun.

Holy shit, I thought, she's gonna make him cum right here in the hot tub and neither one of them gives a damn that I'm ten feet away watching every fondle, every squeeze. And whenever one of them looks my way, they can see that I have one hand on the side of the tub and the other one under water, rubbing where no decent woman rubs in public.

Let me set the scene. My name is Dorothy; you may remember me from Happy Birthday, also by maryjane on this website. The start of this story was originally intended to be the conclusion of that one but I became in a hurry to post the prior one. Anyway, if you read that prior one, fine, but it's totally unnecessary for this one.

I'm now 26, ten years older than that prior story. I'm now the Cruise Director on the brand new "Magnificent Lollypop", a luxury liner with only 554 passengers, every cabin and suite with a large veranda. I started out with this line just after my college graduation as an Assistant Cruise Director, supervising children's games and calling out Bingo numbers.

It only took five years for me to fuck my way up through the ranks to become the first Cruise Director on this new ship. At first, it was simple nepotism, since my Daddy owns the cruise line. You've heard the old expression, 'this is my daughter, and she's going to start out at the bottom for two weeks'. Well, it took longer than that. Some of the officers were hesitant to fuck me because they were afraid that Daddy might learn and disapprove – even though he and I had often rubbed body parts way back when. And I was afraid to fuck some of the officers because I thought they might be spies solicited by Daddy to keep an eye on me.

But hard work, decent skills and liberal use of my pussy and mouth finally carried the day.

The Lido Deck was almost like the deck of that name on every cruise ship. In the rear, it features a buffet area for breakfast and lunch, in our case supplemented by outdoor seating and a small swimming pool and hot tub. The center of the ship has the main pool with a regular hot tub at each corner. Ahead of that is the spa and health club. But in front of that, the Magnificent Pinafore features a huge hot tub, unknown to most passengers and accessible only through the Men's and Ladies locker rooms. Where an average hot tub can hold maybe seven or eight at once, the tub I'm describing could probably hold 40 or 50 people comfortably.

On a late afternoon, with the ship steaming due South on the Pacific side of the U.S. toward South America, the sun was rapidly descending toward the Horizon. Pool areas were rapidly thinning out as couples – no children welcome on this ship – returned to their cabins for drinks, orgasms and showers, usually in that order. I was all alone in the huge tub, enjoying a break, sipping a drink, enjoying the quiet and the last rays of the day.

Then I was joined by Patrick and Kathy, each emerging from the appropriate locker room. I had quickly learned their names the first night out from Vancouver. They approached me to say hello as I was sitting at a bar, having just introduced the comedian to the show audience and as I waited to go back on stage and announce the mandatory 'wasn't he great?'

It had taken only one glance for me to understand the people in front of me. Patrick was sixty if he was a day, tall and erect, judicial gray mane (he was a businessman). I could tell that he had class. On him the mustache looked good, though I generally prefer a smooth face when a man goes down on me. Kathy was between nineteen and twenty-two, extremely pretty, totally overdressed for the first night of a cruise in a strapless gown that accented a lovely rack made for sucking and hips made for fucking.

Only one question remained, and I chose not to ask it aloud. How much was he paying for her companionship on a sixteen day cruise? For surely she was not with him for love.

My guess would have been USD 10,000 to 15,000. She was clearly not a pickup nor a plain old whore; she was a top drawer call girl.

So there we were in the otherwise deserted hot tub. Patrick and Kathy were sitting up on the edge of the tub, their only wet parts being feet dangling in the water. He wore a skimpy racing bathing suit, she a simply bikini top with g-string below. We exchanged banal pleasantries. Then, while making some comment about the food aboard ship, Patrick casually put a hand on the inside of Kathy's thigh and began to slowly massage the area. She leaned against his side and reciprocated the rubbing.

As they stroked, they both looked at my face, seeking a reaction. Having been trained never to show any response to the strange things that passengers might do – after all, they were paying top dollar for the cruise – I kept a straight face. That became more difficult when Kathy's hand moved to rub Patrick's bulging tool and he slipped two fingers under her g-string and inside her pussy.

What was I to do? I was already playing with my clitoris but did I want to become a party to scene across from me? After all, my job made me into a representative of the cruise line and even though everyone was an adult, some of our passengers were mature enough – i.e. 'seniors' – that they had not been brought up to see such goings on in public.

"Patrick, Kathy, your fellow passengers would not care to see Patrick's cum floating in this tub."

"Dorothy my dear," Patrick said, "I'm sure that Kathy would be happy to use her mouth when it's time for me to cum." She nodded enthusiastically.

"And you think the old geezers want to see that when they come out here for the tub?"

"Plenty of them, I'm sure," he said with a smile, "but I take your point. We'll take it down to our suite. Would you like to join us so you won't have to take care of yourself?" He was staring at my rapidly moving hand as he asked.

I looked at Kathy. "How much are you getting paid for this cruise?"

She looked shocked, but then she smiled. "That's a trade secret."

I looked over to Patrick. "Why should I give it away when you're quite willing to pay for it?"

He studied me – face and body – for a long time. "What time do you go off duty?"


"I'm paying Kathy USD 15,000 (we had sailed out of Vancouver, Canada) for the cruise." Kathy made a sour face at the disclosure of her fee, but Patrick continued. "I'll give you USD 7,500 for the rest of the trip, my suite only, no public togetherness."

"No anal," I said.

"Agreed," he replied, clearly reluctantly, "but you'll have to take care of Kathy too." At that point, Kathy's sour face turned into a smile. I nodded. Then I held up my hand like a traffic cop.

"Alright, folks, that's enough joking around. First of all, we cannot allow any sexual activity on deck, so I'm closing this tub down now. It's time to get dressed. Secondly, if any of the crew ever took money for having sex with a passenger, they'd be fired on the spot and thrown off the ship at the next port. And the same applies to me, except that since my father owns the cruise line and my husband is the Captain, I'd just be confined to quarters until we get back to Vancouver. So thank you but I don't need your money.

"On the other hand," I continued, looking at Patrick, "my husband wouldn't mind watching Kathy and I put on a show if you let her out of your bed for a while, and he and I wouldn't mind if you watched also."

She giggled, he smiled, and they went to their respective locker rooms. I called down for crew to shut down the tub and then walked into the Women's locker room to dress. Kathy was by then naked. She hugged me and kissed my cheek. My pussy gushed as I touched her bare curves, her nipples hard against me. I squeezed one of her tits. Our lips met as lovers' lips.

"Is midnight OK for you?" she whispered, although we were alone.

I love this job.

For the rest of this story, you need to Log In or Register

Story tagged with:
Ma/Fa / Fa/Fa / Swinging / Oral Sex / Squirting / Cream Pie /