"But you can't play strip poker on an airplane!"
The moment I said that I knew that the offer to play a game was much more than cards. Looking at me with a devilish grin was the twenty-year old babysitter of my brother's kids, who I had just met at the airport two hours earlier.
Brown eyes sparkled beneath slightly arched eyebrows, set in flawless skin. We were enroute to Maui for a family vacation, me, two of my brothers with their wives, four children, and two of their sitters. My brothers lived in Eastern Washington and on my occasional visits to them I had been introduced to a variety of sitters, but not Heidi. I was soon to get to know her quite well.
Several months before this trip my younger brother Tom called to suggest we all get together for a family gathering in Hawaii. Knowing that I had been there before he asked me to pick out a suitable hotel with all of the amenities. My favorite island in Hawaii is Maui and my favorite hotel is the Grand Wailea resort.
The Grand Wailea is now a Conrad Hotel in the Hilton family but then was independent and the finest hotel on Maui. It had a day and evening camp and pool for kids, which makes it perfect for families. It also has a great spa for the adults and several golf courses across the road. I made the arrangements for Tom, his wife and 2 kids, and for the middle sibling Spencer, his wife and two kids.
Spencer asked whether he could bring along two of their regular babysitters, who he said that he had promised the trip. I made reservations for four rooms, 2 adjoining for Spencer, 1 for Tom and 1 for myself. By using my past visits to the hotel, my Platinum Status, and by filling four rooms I convinced the hotel to upgrade me to an oceanfront room.
We met at Sea-Tac for the Hawaiian Airlines flight. Everyone else had come over that morning on a commuter flight. Waiting at the gate I saw the herd headed my way. Everyone was happy and smiling. Both sitters caught my eye.
Introduced first to Heather, I saw she was tall, about five feet nine inches, a hair shorter than me. She was solidly built but not fat. Heather had curly strawberry blonde hair that she wore well down over her shoulder. Attractive, with fair skin to match her naturally light hair, she betrayed her Irish roots.
Then there was Heidi. She was about five feet five. Heidi had darker skin, although I later learned it was courtesy of a tanning bed. She had dark brown hair which she wore up in clip. Heidi has a oval face, smaller, with a tiny mouth. She seemed to be well proportioned, with healthy 34's and a modest waist. She introduced herself with a big smile and said that she had heard a lot about me. I guess Spencer had been telling her about my successful law practice.
The plane was surprisingly empty as it was the end of the off-season and the flight had just been added in anticipation of the summer. The ten of us shared the final fifteen rows with only twenty-five other people on the 767. The kids moved up to the seats with the best views of the video screens (no seat back monitors in those days). I took my customary seat on the windows. After take-off we had lunch and the kids watched the movie. After talking to Tom and Spencer and their wives for a while, I excused myself to go back to my book.
After a while I got bored with it and borrowed a deck of cards from the flight attendants. The airlines gave them out as advertising, and I thought it might come in handy if we had a rainy afternoon stuck in the hotel. I played solitaire for a few minutes when Heidi came from aft and sat down beside me.
"What are you playing?" she asked.
"Solitaire. I haven't played in years and think I finally figured it out. Would you like to join me?"
"But only one person can play, how about something else?" Heidi suggested.
"Hearts? Spades? Cribbage?" were all that I could offer.
Then she said it: "How about strip poker?"
Without thinking, I said "but you can't play strip poker on an airplane!"
Heidi laughed and asked "why not?"
"Well, for the first thing, its kind of hard to take off your clothes in front of everyone, '' I offered meekly.
She had the upper hand with her bold statements. "Who says we have to take off our clothes......here."
I was flustered, not expecting the come on from a woman half my age.
"Well I guess we could play, and keep track of what we lose."
She answered "You got it, and maybe finish the game later."
I dealt the cards. The short story is that I lost my shirt, she lost hers, she lost her pants and bra, I lost my pants and then shorts, leaving her with her panties.
The game was full of sexual comments. Enjoying her word plays, we took our conversation to a very personal level. We had played the game for about fifteen minutes and gotten Heidi down to her panties when Spencer walked past and Heidi suddenly got up and left.
Nothing else happened until after we got to Hawaii that afternoon. The kids immediately wanted to go to the pool. I went to my room and changed, then went down to join everyone. Heidi seemed to be ignoring me. She was in the pool playing with Spencer's four year old daughter Madison.
Heidi finally got out and walked over to the adults. I think every man within a hundred yards noticed, and plenty of angry women too. Heidi was stunning in a black and white print bikini. Her breasts overflowed the cups as they sat high and pert on her chest. Her hips were slim, the legs very nicely shaped. We sat and talked for a while with the group.
That night was quiet, as was the next day when I played golf.
The second night was interesting. We all walked to the Outrigger next door for a luau. The ten of us filled a large round table. I was tired from the golf and spending the day in the sun and had not paid any attention to Heidi.
After we sat down I realized she was sitting directly across the table. She was wearing a pair of black slacks, cut low on her hips. Heidi had on a white silk top with a scoop neck cut low in the front. After sitting there a few minutes I was admiring the valley between her breasts. When Heidi would lean forward, the top fell even lower and you could see the entire inner half of her breast. The bra strap was positioned high enough that it created a small bridge where it crossed the gap between the globes. The white threads passing above the tanned skin hit me right in the gut, or I should say my groin. It was sweet. Extremely sweet.
Then Heidi stood up to help the kids walk down to the beach. When she bent over to help Madison up from her chair, her blouse fell forward, exposing her entire breast encased in the white bra. I didn't know if she wore the blouse on purpose or simply dressed like this all the time, but I was enjoying the view and spent a good part of the evening feasting with my eyes as well as stomach. Again, nothing happened.
On the third day my brothers, their spouses and I went to Lahaina to shop while the sitters watched the kids. We got back to Wailea mid-afternoon. Everyone was at the pool so we changed and went down.
Heidi was in the same bikini, looking very nice but spending most of her time playing with Madison in the kiddie area. Heather was there too, in a nice pink bikini that contrasted with her fair skin, but cut more modestly than Heidi's. After a while Madison started to get tired so she led Heidi over to the adults. I'm her favorite uncle and she enjoys letting me spoil her.
This afternoon she let go of Heidi and walked over to my chaisse. Madison crawled up and gave me a big hug. She looked exhausted. I asked her if she needed to take a nap. Madison nodded and put her head on my shoulder.
"I think she's done for a while, can someone let me into your room so that I can put her down?"
