Hawaiian Heaven

"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?"

Heidi quickly jumped in with a "sure I can help."

Heidi quickly grabbed her bag and pulled up a pair of shorts over her bikini bottoms.

We didn't say much while walking up to the rooms, perhaps contemplating what might happen next or trying to figure out how each of us could make it happen.

Admittedly smitten by Heidi's looks, intelligence, charm and aggressiveness, I wasn't sure how to take it to the next level, and was also worried about what my family might say if they found out I was sleeping with one of their kid's sitters.

Soon we got to the room, where I put Madison down on one of the beds, sound asleep.

"Come on," Heidi whispered, beckoning me toward the open door into their adjoining room. She gestured for me to follow her.

Once through the door she quickly dropped her shorts, which were wet, leaving only the bikini bottoms. Open drapes let the afternoon Hawaiian light flood the room.

Without saying another word, Heidi crawled up on the bed and lay on her side.

She patted the bed beside her and said, "how many times do I have to ask you to come on?"

That was enough of an invitation for me. I lay on my side facing her. Heidi's skin was almost flawless. I put my hand on her hip and pulled her gently toward me. She scooted right up against me. Our faces were inches apart. Heidi's brown eyes were looking directly at mine. My hand toyed with the strap of her bikini, pulling, twisting, then untying. When the strings fell apart I leaned forward and kissed her. Heidi opened her lips to meet mine. Our first kisses were passionate, jumping past the tender, hesitant stage as we both sought to relieve the tension that had started on the flight. Heidi's tongue pushed past my lips into my mouth, tapping and then twisting around my own. My hand was roaming on her rump, rubbing the soft skin on her hip and moving as far as her crack. We were both getting quite turned on.

We kissed for a few minutes like this, when I heard the door to the other room opening. "Crap" I said, jumping up.

Heidi looked surprised too, uncertain why I had jumped, and then she realized what was happening. She quickly reached for her bikini strings, which drew my attention to the neatly trimmed patch of brown hair. Heidi had just finished tying it and was sitting on the bed, with me sitting on the couch, when Spencer's wife walked into the room.

She seemed to realize that something had been interrupted and quickly informed us that the other kids saw Madison go and decided to also nap. I used the moment to graciously excuse myself, hoping that my t-shirt covered my raging boner.

Heidi saw it and smiled, saying "we'll finish that conversation later." I went back to my room and sat out on the deck to get a few rays.

The phone rang. "How about we finish our conversation now?" was her opening line.

"Where are you?" I asked.

"In the lobby, they think I was going down to the pool, I just ditched Heather."

"So I guess you haven't changed from your suit?" I asked.

"No, and I'm afraid it's about to come untied again, maybe you could help me with it again, what is your room number?"

I told her and she said she would be up in a minute. This got me going again.

Heidi was there in a few moments. After stepping in there was no doubt what she wanted.

Heidi put her arms around my neck and pulled me against her in a deep kiss. My hands went to her ass, pulling it into my member. She groaned as it dug into her stomach, then extended up on her tiptoes to direct it against her crotch. We kissed, bumped and ground for a minute or so, then I broke the kiss and led her into the bedroom.

"Something needed tying?"

"My bottom," she replied.

"Yes your bottom, but I can't find it with your shorts" (Heidi had put her shorts on over her suit to go to the pool).

"Let me work on those," I said, standing in front of her.

I reached down and unbuttoned the waistband. With access granted, I slid my hand down on the top of the bikini bottom until I felt the material rise with the first strands of hair. Going further I started to cup her front, bringing my fingers around to her slit.

Heidi was standing with her eyes closed, hands on my shoulders, gently swaying to and fro. The nerve receptors on the tips of my fingers felt heat, then moisture. Heidi moaned with pleasure, licking her lips with a soft pink tongue. Pushing my fingers slightly, the fabric yielded ever so little to mold on her lower lips. She moaned again and then slightly staggered, losing her balance as she concentrated on the sexual feelings running up into her body.

"Bed," she whispered.

Pushing her shorts down, Heidi kicked them off and then lay down on her right side on the bed, just as she had not so long before. I lay in the same position facing her.

My right hand again reached out and pulled her hip toward me. She scooted over.

"Where were we?" I asked.

Heidi responded: "Right here. I like it here."

"So do I," I said and kissed her. We immediately resumed deep passionate kisses.

I also resumed running my hands over her hip and ass, inserting a finger underneath the fabric and running from the tie across the curve of her bottom as far as I could reach. Knowing I had done it before and that she had not objected, I tugged at the strings holding the bikini bottom together.

Pulling them apart, I felt the front fall down, then brushed the back off Heidi's ass. Freed from the barrier, I brought my hand around to Heidi's belly, which was smooth and almost as flat as glass. She knew what would happen next. As I began to slide my hand down her stomach, Heidi lifted her left leg, curled it and placed it on top of my right leg, granting me full access to her most private parts.

First reaching the soft strands of hair I tarried, curling them in my finger while I pressed down on the top of her pubic bone, causing it to pull her clit from side to side within its hood. Going further my finger reached the top of Heidi's outer lips, easily accessible from the sparse growth above.

Heidi gasped as her lips were parted, the blood-filled tissue separating and exposing her inner essence. Sliding the full length of her lips, my finger cleaved them in two then pulled back to rest above her clit. Heidi's point was fully exposed, my initial guess thinking it was eraser sized, as it stood out from her skin.

Drawing circles around the button, my massage caused Heidi to grip my neck even tighter. She broke our kiss and pulled my head onto her shoulder, pressing it in a vise grip. Finally stopping with the circles my assault shifted to the clit itself, pulling it up and pressing it from side to side. This did it for her. Heidi's grip tightened further.

A spasm swept her body as the orgasm flooded her senses. The liberal moisture now flowed even faster from her pussy. Heidi shook several more times but did not lose her grip on my head. I had a hard time maintaining contact with her clit but managed to hang in there while she reached her peak and came down the other side.

Finally Heidi released her grip on my head, freeing me to return my mouth to her lips. Now more tenderly we kissed, a different passion than we had felt earlier. We were now lovers, or at least had taken the first step to being lovers, rather than the hesitant hunters of earlier in the trip.

Without saying anything, Heidi reached down. She didn't slow as her left hand passed down my chest. "Now its my turn" she said as her hand reached the waistband on my swim trunks.

Darting inside, she gripped the head of my shaft. "Nice" she said, "very nice."

Heidi sat up and pulled my trunks up and away from my cock, then down my legs where I kicked them off. She lay back down beside me and resumed our kissing. Heidi also went back to rubbing my dick, but now left the head and palmed the length, gently stroking up and down. I thought for a few moments that she was going to try and make me cum with a hand job as I had only rubbed her pussy.

"Want more?" she asked.

"Please," I replied.

"I better get some too" she teased about our foreplay.

"It's just what I had in mind," I returned, thinking about the silky smoothness that I had touched with my fingers and wanted to taste with my tongue.

Removing her hand, Heidi shifted down the bed. The tongue that had been swirling around my mouth, teasing my lips and teeth and tongue, was on my member, teasing the head, glans and shaft. Heidi was an incredible kisser and I found out now that she gave great head. Breaking her sucking from time to time she would kiss the head, squeeze out little drops of pre-come and then flick them off with her tongue.

Heidi would then go back to a full cock sucking, drawing most of my seven inches deep into her mouth until I could feel the back of her throat. Without gagging she took it in and out while using her tongue to tantalize the shaft.

Heidi was just amazing. I don't think any woman had given me head like this and she was barely 20. Heidi then took my balls and gently massaged them. Because they were tight up against the base of my dick there was little she could do but she went for it anyway. Heidi sucked for a good five minutes without a break before I felt the start of an orgasm.

I had been running my fingers through her hair, feeling the conditioned strands with their full body. Heidi must have felt my cock start to swell because she grunted and gave a good groan. Heidi pulled back a bit and concentrated on the head of my dick.

She put her teeth on the shaft immediately below the head to get purchase, then began to suck hard on the head. That was all it took for me. The cum shot the full length of the shaft in a tremendous rush. Heidi swallowed it without pause, then took the second, third, fourth and fifth shots as well. Heidi had done her job well because I wasn't done. My member continued to spasm, producing less and less each time but Heidi treated each as if it was as important as the first. She really did a first rate job.

As my cock gave way as the blood drained out, Heidi let it fall out of her mouth. "Umm that was good."

"Umm you were good," I replied. She moved back up the bed and into my arms.

"Incredible" I said.

"Thanks, I love your cock, it's just the right size."

I was already rubbing her ass, running my hand over the tanned skin. "I think its my turn, or actually your turn," I told Heidi.

"I can't wait," she said.

"Actually I haven't even gotten your top off," I said, raising my hand to the base of her breasts.

"You don't need to," she retorted. Worried for a moment, I asked what she meant.

"Didn't you see enough the other night at the luau?"

"Well I was wondering whether that was for my benefit."

"It sure was."

By now I was running my fingers along the bottom of her bikini top. "I especially liked this spot," I said, running my finger to the small strap that passed between the two breasts, connecting two triangles of fabric that held back her breasts.

"Whenever you leaned over I could see this, even the space here between the strap and your chest." My hands now ran up between her breasts, first darting under the strap, going under the bridge formed by the mounds.

Next, moving up further, I felt the globes. Her skin was as soft as it looked, like a marshmallow as it gave gently under my fingers.

"I saw you looking," she said, "especially when I got up and let you see it all, even with a bra on."

"So that was on purpose too, it was sweet." My hand now moved over to Heidi's left breast. I ran my fingers along the edge of the fabric from the top of the triangle down to the bridge at the bottom, then back up to the top. Coming down the second time my finger worked its way along the fabric, lifting it slightly.

Heidi shuddered and closed her eyes, enjoying the touch. After moving back up to the top, on the third pass two finger tips were on her breast, sliding up the mound and down the other side. Heidi whimpered this time as the fingers returned to the top.

The third time I moved in slightly more. Half way down the breast I felt a small change in texture, finding the edge of her areola. Stopping downward motion my attention went to the slight rise in the skin. Heidi was now biting her lip. Using my ring finger and pinkie to push away the fabric, Heidi's nipple popped into the air and landed on my index finger. Rubbing its hardness, I could feel that it was not too large. Pinching it gently, Heidi's lip was now quivering. She must have had extremely sensitive nipples. Gently I circled the point and alternately pinched them, pulling them upward. Heidi's torso shook as she had a small orgasm.