My Dare Ch. 01

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I was standing on the lanai staring out at the greatest view in the world. My second floor condo was on Napili Beach on Maui, facing the island of Molokai. Beyond the small lagoon was an open waterway that was a favorite playing ground for humpback whales migrating back North this time of year.

I should have been happy; after all, it was the Christmas holidays, and I was in Paradise. But I was alone for the first time in 30 years. My wife had left me for another, younger man, and the one thing that I insisted on in an otherwise-amicable split of assets was the Hawaiian vacation we had scheduled (and which I knew she would love to take her new “boy-toy” on). So here I was, with 15 days to kill in “our” favorite spot in the world.

I don’t want to dwell on the past. Suffice it to say that I had gotten past the shock, anger, hurt, and “oh, poor me” stages and was ready to start the rest of my life. I had maintained more than $2 million in the assets split, was on good terms with our 22-year-old daughter who now worked in Denver, and had a consulting job that allowed me to work when and where I wanted. I had worked hard to take off 30 pounds of middle-age fat and was in better shape than I’d been in 20 years.

I was determined that I was going to enjoy this vacation. I didn’t realize just how much it would define my life. Besides the shirts, shorts, and sandals that are all you need to go anywhere on the island, I had brought a digital camera, a dozen paperbacks, my MP3 player, and plenty of running clothes. I stopped at a local snorkel shop for mask and fins and was now ready for two weeks of sun, sand, and sea.

Since it was mid-morning, the first thing on my agenda was a 5-mile run. I walked back into the condo and had just put my jogging shorts on when I heard voices coming from the unit directly below me. Great, there goes the neighborhood! Water running, doors slamming, flip-flops flopping. I grabbed my shoes and followed the noises out toward the beach. Looking over the railing of my lanai I saw three ladies appear below, heading toward the beach a few yards away. OK, there couldn’t be many more in that 1-bedroom unit, and at least they weren’t grade school kids. I sat on the lounge chair to put my shoes on, checked that my key was tucked away in my hidden pocket, and stood up to go back inside. I glanced out at the beach and saw my downstairs neighbors at the water’s edge, all shading their eyes and staring out to sea. Maybe they see whales, I thought. Grabbing a pair of binoculars (conveniently provided by the condo owners), I started scanning in the direction they were looking. Sure enough two spouts appeared several hundred yards out.

“Good eyes!” I yelled to the trio. They turned and I gave them a grin and thumbs-up. They waved as one and turned back to watch.

Whale watching from the beach is tough, especially at water’s edge. I had the better view from the second floor, particularly with the high-powered binoculars. I could see the size and regal beauty of the largest whale and recognized the second as a much smaller animal.

“It’s a mother and calf,” I yelled to the girls. They obviously heard me since the middle one started to jump up and down in excitement. I aimed the binoculars down at the movement, and was rewarded with a view of a spectacular pair of legs-runner’s legs, if I wasn’t mistaken. No, three great pairs of legs, all slightly tanned like they had just arrived like myself. Since all three had cover-ups on, I could only guess at ages or shapes beyond the legs. A passing lecherous thought, and I returned to watching the whales. They eventually sounded and the show was over.

Turning to head back into the condo, I thought to myself, “This is a good start to the vacation. Whales in the first hour, and I’ve kind of broken the ice with my neighbors.” I assumed they were attached, gay, old, or out of my league; but at least they wouldn’t look at me like a freak if I spoke to them again.

I headed out of the condo complex on my run. Napili is an isolated community but is right next to Kapalua at the western edge of the “tourist” part of Maui. So it wasn’t more than a mile before I was running on roads that were mostly for local and a few surfers’ use. For 45 minutes I listened to music and thought about filling the companionship gap during my stay. First, I needed to find out more about my downstairs neighbors. Then there was a cute girl (mid-twenties) who worked in Lahaina and had attracted my attention the last time I was here with my wife. Back then I just passed it off as flirting-now I could see if it was more than that. And if none of that worked out, I’d check the beaches in Kannapali and Kehei, where I knew that at least the snorkeling and bikini watching were worth the drives.

I had turned around and was nearly back to Kapalua when I saw another jogger approaching. It was clearly a woman. As she came nearer, I recognized the “bouncer” from the beach. She was about 5’4″, late 30’s, about ümraniye escort 110 pounds, with dishwater blonde hair pulled back in a ponytail. A black sports bra kept very nice B or C tits squeezed in for jogging, wrap-around mirrored sunglasses hid her eyes, and her skimpy running shorts highlighted those legs I had noticed before.

I took out my earbuds and said “Hi, neighbor,” as we passed. She glanced at me, quickly smiled then turned immediately to join me as we jogged along the sea wall.

“Hi-you’re the guy in the condo above us, right?” she said as she caught up on my right. Not surprisingly, she wasn’t even breathing hard since she had just started out.

“That’s me-Steve Riggs. Are you heading back already?’ I asked.

“Jenny Hendricks,” she said as she held out her left had palm up.

I slapped it in greeting. My sweat didn’t seem to bother her. We ran back toward the condo, even though Jenny had just started. She said that she just needed to loosen up after the trip from the mainland. As we talked, it turned out that Jenny, Susan, and Amber were all from Seattle and were in Hawaii to celebrate Amber’s 30th birthday as well as Susan’s recent divorce. I took that opportunity to give Jenny the short version of my story, without sounding bitter. While I hadn’t met the other two ladies, I didn’t want to kill all chances with Jenny by coming across as someone needing a shoulder to cry on. No one comes to Maui for that.

Jenny asked me how far I’d run, and seemed impressed with my answer. I pointed out that I was in the best shape of my life and that I normally ran at 6000 feet, making sea level seem easy. Her eyes looked me up and down as we ran; I assumed she was assessing my comment about being in shape.

We reached the condo complex, stopped, and stretched for a few minutes. It was now my turn to more thoroughly take in the charms of my “running mate”. Jenny had spread her legs apart, bent over at the waist and was pushing on the ground. The shorts pulled up to expose her taut inner thighs. The globes of her ass were clearly defined by the nylon shorts, and the small of her back was sexy as hell. She caught me looking at her tight butt and thighs as she looked up between her legs. I smiled and said, “Let me help.”

I walked around to her front and gently pressed on her shoulders. I could tell this girl was limber as her head nearly touched the ground. We stayed that way for about 30 seconds, as Jenny rotated her head slowly to work out the back and neck muscles. I realized that she also was able to see up my legs and under my running shorts as she turned her head. Oh well, fair is fair I reasoned.

I let up on Jenny’s back and helped her stand. As my hand left her arm, it occurred to me that she hadn’t said a word since she’d caught me looking at her ass. “I apologize for staring at you, but there is no way that you could be 30 with those legs and that butt,” I said.

“Actually, I’m 35, thank you, and there’s no need to apologize,” she said with a smile. “We all came to Hawaii hoping that we would still be noticed, so my bending over and sticking my ass in your face was not exactly an accident.”

“Well then, nice ass,” I replied. We laughed and began to walk back to our units.

“After I cleaned up I was going to make some coffee,” I said. “Would you and your friends like to come up and join me?”

“Amber and Susan were heading into Lahaina when I left,” she said. “But I’ll be up in half an hour.” We agreed to meet and headed our separate ways.


Jenny couldn’t believe her luck. Steve was just what the doctor ordered for her, and probably for her girl friends too. He seemed like a great guy, was unattached, and not afraid to joke around. They had checked him out at a distance as they stood on the beach and he had been on his lanai. Amber had commented to the others as they pretended to concentrate on the whales, “Nice. Our age and hopefully alone. I get first dibs when we get back from shopping.” They had all laughed, knowing that the guy was probably there with his wife and two kids. Now Jenny was chuckling to herself for another reason as she stepped out of her running shorts and pulled the sports bra over her head. Steve was definitely eligible and, she hoped, willing. She had seen a nice bulge when he was helping her stretch, and with a little encouragement, she was sure he would show her more.

Jenny stood in front of the bathroom mirror admiring her still-perky breasts and trimmed reddish-tinted bush. All three women had gone to the tanning salon in Seattle a few times so they weren’t completely white in Hawaii, and all three had gotten bikini waxes as well. Susan had hinted at something more, but no one had seen the others naked yet.

Jenny ran her fingers lightly over her pussy lips and through her close-cropped pubic hair. Her outer lips almost hid her prominent clit poking out the top. She used one hand to spread herself open üsküdar escort and ran a finger none-too-gently along her inner lips to scratch the itch that had suddenly started in her pussy. She realized that she was wetter than she had been in weeks. Bringing her hand to her face, she sniffed the musky aroma. She reached down with both hands, opening her cunt with the left and shoving two fingers in as deep as possible with her right. She watched herself in the mirror as she pistoned in and out, juice starting to splatter the sink top. Just as she felt herself cuming, she grabbed her clit with her left hand, her tits with her wet right hand, and leaned back. Spray flew out as she came, hitting the mirror four feet away. She continued to tweak her clit as she came down from her high. With a final shudder, she tweaked her nipples one final time, quickly wiped up her squirt with a Kleenex, and climbed into the shower.

As she shampooed her hair and soaped her body, she recalled why they were here. Jenny, Amber, and Susan had come on this trip not only to excise some demons, but also to get laid. All three had been “off the clock” for several months; Amber was the most vocal about her need for cock, but Jenny knew she had almost as much desire but wasn’t willing to say it out loud. While the three were good friends and admired high points of each other’s bodies, they hadn’t fooled around. At least as far a Jenny knew. Climbing out of the tub, she grabbed a towel and turned to look back at her high point in the mirror-her ass. She ran for one reason only and that was to keep her buns and legs taught. Face, tits, and tummy seemed to be holding up by themselves. So while Amber did crunches to preserve her hourglass figure and Susan spent hours on her face and hair, Jenny ran.

Running the hair dryer quickly over her head, she opted for the wild, wet look and turned to dress. Cotton shirt, no bra. Thong and short, schoolgirl skirt, both black. She wanted to keep Steve interested and even thought about leaving the panties at home. No, too much. As she slipped on her sandals she checked herself out one last time. “Not bad for 35,” she said out loud as she turned to walk out the front door.


I went in, ground some beans, and started a pot of coffee. I then jumped in the shower, quickly cleaned up, shaved, and was ready when Jenny knocked at the door.

She cleaned up well–yellow flip-flops, bare legs, a short black pleated skirt, and v-necked white knit shirt. I felt underdressed in my baggy shorts and muscle shirt, even though both had subtle Hawaiian prints. “You are now getting your second official admiring stare,” I said as I let her in.

She slipped off the flip-flops and left them at the door as she entered, flashing me that gorgeous smile. “I smell coffee,” she said as she scanned the place. I had unpacked earlier so the condo met with her expectations. “Looks just like ours only no ladies’ underwear lying around,” she added as she walked toward the lanai to check out my view.

Funny she should mention it, since she had clearly left her bra downstairs, probably in that mess of ladies underwear she was talking about. Her shirt wasn’t tight, but there was clear sign of nipple-I’d estimate 34C now that the sports bra wasn’t hiding her chest. Her hair was down, shoulder-length, damp and curly. I liked the fact that she had hurried to get here, but I wasn’t going to insult her by saying so.

I grabbed two mugs, quickly filled them, and followed her outside. I figured since she was from Seattle, she didn’t need sugar or cream (I was right, by the way). Setting the mugs down on the table, I joined her at the rail. “Your view is better, but we can get to the beach easier,” she commented.

I casually put my arm around her waist, glanced at her and said, “Tell me about yourself and your friends.”

Jenny seemed a bit surprised that I asked, but had no problem with my arm. In fact, she subtly inched closer so that our hips were just touching. She talked about her job at Boeing, her failed marriage that ended seven years ago, her small house near Lake Washington, and her golden retriever named Sleeper. Jenny seemed comfortable on her own; she didn’t mention a man in her life and I didn’t ask.

As she talked, I reached back to the table to retrieve the coffees, set hers on the rail, replaced my right arm around her waist, and sipped my Kona with my left. Jenny lifted her mug, sipped, and commented, “Great coffee.”

She continued with her description of her roommates. She had known Susan all her life; they had both moved from Northern California to attend the University of Washington or UDub as she called it. While there, they had met Amber as a new pledge at their sorority during their senior year. Following college all three had stayed in Seattle to take high-tech jobs; Jenny and Amber worked at Boeing and Susan was the brains behind a startup that had been recently acquired by Microsoft. Needless ataşehir elit escort to say, Susan was paying for the trip; her ex-husband had gotten more than he deserved of the $20 million from the sale, but she still was set for life. Both Jenny and Amber were more than comfortable as well-paid engineers, but Susan was now in a league of her own.

I was intrigued by Jenny’s matter-of-fact description of the three women as computer engineers. I explained that I consulted on electronic subsystems myself and had found that my career field had very few females. An idea was forming in my mind as Jenny described her areas of technical interest; I’d need to meet the other two before I said anything.

In the mean time, I had moved my arm from Jenny’s waist and was holding the mug with both hands as I stared out at the bay. As Jenny talked, her left hand had casually moved to touch mine, and her fingers were gently running across the top of my right hand, down my wrist, and back up. It was almost like she was unaware of her actions. As I listened, my eyes were drawn to her light touches, and I felt my cock stir. I turned my head as though hanging on her every word, but in reality I was checking out her body language. As she continued to glance between me and the sea and describe their preparations for the trip to Maui, I became mesmerized by her full lips, flashing eyes, and cleavage that had appeared as she leaned forward on the railing.

“…so we flew First Class thanks to Susan, got here about 4 hours ago, and found this helpful guy before we could even unpack!” she concluded, turning to face me.

That was my cue to lean over and gently kiss Jenny. She responded by grabbing the back of my head, mashing her open lips to mine, and probing with her tongue. I broke away after a few seconds of our feverish lip lock and turned her toward the rail. As she leaned over with her breasts pressed to the rail, I knelt behind her and ran my hands up those incredible legs. Jenny lifted up on her toes, not to avoid my wandering hands, but to make herself more accessible. I pushed up under her short black skirt, and it followed my hands over the curve of her taut butt. I laid it on her lower back and slid my hands back down over her ass cheeks that were divided by a narrow strip of black thong. I caressed up and down, kneading the firm flesh, watching the thong slide deeper into the crack of Jenny’s ass. I leaned forward first kissing and then gently biting the fleshy globes as my hand continued to wander over the sides and backs of her legs.

When her skirt slipped back down, I reached up and pulled it over her hips and down her legs. She lifted one foot at a time to step out of the skirt, then planted her feet further apart. The thong had crept between her outer pussy lips, and as I ran my fingers up the inside of her thighs to touch those invitingly soft folds I was surprised at the juices I encountered. I touched the her again, running my fingers gently over the hairless skin, pushing the thong further in to her pussy.

Jenny moaned, then reached back to slide the thong down over her hips. It stopped at the bottom of her butt, dangling from the crotch wedged between her inner cunt lips. Again I kissed and kneaded her butt, pulling the cheeks apart to expose her puckered asshole. Holding her cheeks apart with my left hand, I Dipped my index finger in the juices below and slowly circled the rosebud, then slipped the tip of my finger into her ass.

“Oh my God, what are you doing to me?” she moaned. I answered by leaving my finger lightly inserted in her clenching butt as I pulled her panties down her legs.

This time they stretched between her lower calves as she had neither the strength or desire to move her legs.


Jenny was turned on more than she ever remembered. Suddenly, she heard her roommates below as they walked out of their condo downstairs. They looked up, saw Jenny and waved. She called down in a shaky voice, “Hi. How was the shopping?”

Susan replied, “Hey Jen, it was great. Check out our new bikinis.” Amber was posing in a fluorescent pink micro bikini that barely covered either her tits or her pussy. She turned to demonstrate that the thong was even smaller in the back. Susan turned around in a lime green number that showed off her ample chest while covering more of her lower body. Jenny wasn’t surprised because she knew her friend was still self-conscious of her weight. “We got you one too,” Amber added. Since the railing hid them from Steve, he couldn’t see who was talking or how they were dressed.

Amber continued, “What are you doing up there? Something naughty I hope.”

Jenny surprised Steve by saying, “I just met our new neighbor, Steve Riggs. Right now he’s got my panties around my ankles and is doing unmentionable things to me behind this rail. Come on up so he can see your new outfits.” She turned to him without dislodging his finger and said loudly, “I’m sure that’s OK with Steve.”

Steve nodded and grabbed one final handful of Jenny’s ass, as she heard two sets of running feet heading for the stairs at the front of the building. Steve’s finger slipped out of Jenny’s asshole, and she reached down to pull her undies off as Steve stood to welcome her roommates.

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