My Dare

I cleaned up the condo and went to bed, dead tired and jet-lagged. As I drifted off, I pleasantly reviewed my first full day of vacation. I mentally pinched myself at my luck to have so quickly met three obviously willing and eager women. Jenny appeared to be a normal, hot-blooded woman that enjoyed many of the same things as I; Susan clearly had issues that I was going to have to work on; and Amber, while an unknown, seemed to be the wildest of the three. I still wanted to check on a couple of other women I had met on the island, but a man could do a lot worse than spending the next ten days with the trio downstairs.

I woke early the second day, still on Denver time, and quickly dressed for my morning run. I went down to the car, collected all the clothes, and, after dropping mine off, headed to the girls' room. We hadn't made any plans but I hoped Jenny would join me on the road, so I knocked on their door. It was 6:00am and still dark out, but Jenny answered in her running clothes as well. When we both said, "Great minds think alike," we laughed and I handed her the girls' clothes. She turned and tossed them at an already-cluttered couch. We quickly walked to our favorite stretching area on the side of the condo and discussed how far we wanted to go as we limbered up. As we headed out, I slowed my pace only slightly to accommodate Jenny's shorter gait, and we both left our earbuds out to talk and listen as we ran.

Three miles out and three miles back brought us home just before 7:00am as the sky was starting to lighten, both of us sweating freely in the high humidity. We cooled down in the side yard of the condo; I ran my hands over Jenny's back and ass as I "helped" her stretch. She made sure my cock was "positioned right" when I bent over. She had thanked me for servicing her friend, and I couldn't help but laugh as I insisted that, while it was rough duty, I was only willing to make such a supreme sacrifice for my really close friends.

So when she was doing her final stretching, bent over touching the ground with her legs four feet apart, I wasn't surprised that she pulled her shorts down over her hips and asked from between her legs, "Are you ready to make another sacrifice?"

"OK," I said. "This is for my close friend, umm, Amber." Her pussy and puckered asshole were aimed directly at me just below the waistband of her running shorts, and my cock was quickly hard and in my hand. True to form, Jenny was already dripping. I looked around to make sure we were relatively private; bushes on all sides protected us, and no one else seemed to be up yet. I moved forward to pull her shorts down slightly and ran my rod through her wet cunt lips to coat the shaft with nectar. In this position, that action felt so good that I continued to dry hump (in this case, "dry" wasn't the right term) Jenny as my crown slid back and forth over her clit. Her shorts pushed up against the underside of my cock, increasing the pressure on her pussy. I held her hips and even pulled the shorts up on the sides. The underside of my shaft was starting to feel irritated by the time Jenny fell forward, collapsing in a clitoral-induced orgasm that left her twitching on the ground. I rubbed her juices over the dry underside of my dick to sooth the burn then pulled my shorts back up.

Jenny slowly rolled to her knees then pulled her own shorts up as she got to her feet. Holding hands, we silently walked back to her condo door. She lightly kissed me and said with a wink, "Thanks for the workout," before slipping into her unit.

"Same time tomorrow," I reminded her.

"Oh, Yeah!" she mouthed with a grin as the door closed.

*****

Amber rolled over as Jenny closed the door. "Whew! You need a shower and not just because you ran," she laughed. Jenny stuck out her tongue at her friend and swung her hips comically as she headed for the bathroom.

"Steve's worked up and ready for you; you can thank me later," Jenny said as she pulled her workout bra over her head. She was sliding her girl-cum-soaked shorts over her hips before she realized that Susan was already in the bathroom with the door closed. Shrugging and turning, she leaned over, pulled the shorts off and walked back naked to the refrigerator to get a bottle of water. Amber watched her friend with growing arousal; the three had never spent so much time around each other unclothed, so furtive glances in the locker were being replaced with frank appraisal. Jenny was nonchalantly pushing up and down on her tiptoes as she drank, stretching her calves. Amber could feel her own pussy tighten as she looked at those great legs. Gazing upward, Amber could clearly see a trail of dampness running down the inside of Jenny's right thigh, nearly to the knee.

She thought, "If I don't get some of that cock soon, I'm going to attack one of these two." Without taking her eyes off Jenny, she rolled out of bed and stood. Grabbing the hem of her shirt, she quickly stripped and walked naked into the kitchen. Susan had made coffee when she got up, so Amber filled her cup and leaned against the counter facing Jenny.

"Am I going to get "floppy" seconds?" she asked her roommate.

"I checked to see if Susan wore Steve out last night," Jenny answered. "I can say for sure that he's fine, just fine."

"I couldn't help but notice that you're leaking," Amber said as she reached down to run a finger across the middle of Jenny's inner thigh. Holding up the evidence under Jenny's nose, she looked at her quizzically.

"Oh, that!" Jenny said dismissingly. "He helped me get off, but I left him as hard as a rock." She went on to describe the morning.

The description didn't help Amber's horniness and it was all she could do to keep from sniffing her slowly drying index finger. Finally, as Jenny turned to put her water bottle back in the fridge, Amber stuck her finger in her mouth to taste the salty residue. When Jenny turned back, Miss Innocent was sipping her coffee.

Susan came out of the bathroom wrapped in a towel, but seeing her friends nude in the kitchen, pulled it off to wrap around her blonde hair. Jenny said, "It's about time! Hope there's some hot water left," as she headed for the shower.

Amber poured coffee for Susan and relayed Jenny's story. As they talked, she picked up her discarded suit and slipped it on. She quickly packed a beach bag with towel, lotion, and sunglasses, putting on a floppy but stylish straw hat. "I'm going upstairs," she told Susan, winking.

"Don't forget we have scuba lessons this afternoon," her friend reminded her as Amber walked out the door.

*****

I walked upstairs and jumped in the shower. As I soaped up, I checked my cock for damage and breathed a sigh of relief when it seemed fine. After quickly toweling off, I fired up the computer and checked my email. I learned from my investigator that Jenny, Susan, and Amber were exactly as they had said, but they had left out a few important details. First, Susan's company had won a prestigious small business award for the Greater Seattle area for both innovation and customer service. Second, Amber and Jenny were both seen by their management as fast risers; they had worked on several internal programs requiring strong electrical engineering background and group leadership skills.

Now if I could find a way to convince them, I believed I could put us all in the position of never having to work again. I had to appeal to their engineering skills first, but the fact that they were beautiful, sexy women was going to provide the key to our success.

As I finished up another note to a colleague in Seattle, my front door opened. Amber stuck her head in; she had quickly picked up on my door code. Showing off her pink barely-there micro, she asked, "Are you up to driving me to a nude beach?"

I closed the computer and jumped to my feet, showing her that I was more than ready. But just in case, I put on a Hawaiian print swimsuit and a tank top, picked up sunglasses, a beach towel, and the keys, slipped on sandals and followed her downstairs. She wore a cute wide-brimmed hat and looked like she had just gotten out of bed. Her suit was practically invisible from the rear, and I purposefully stayed back a few steps so I could watch that bubble butt.

I knew there were isolated beaches on Maui that were "clothing optional", but my ex-wife had never shown an interest; so I didn't have any idea where I was going. We drove to a nearby coffee house, and I picked up muffins and Kona coffee. We sat in the parking lot and ate as we waited for the sun to rise. Amber explained that she had done a web search before leaving home and pulled out a Google map. We headed west from the Napili area, quickly leaving civilization (at least the tourists) behind. The top was down, and Amber spent her time trailing her nails up and down my right thigh, occasionally dipping under my suit leg to stroke my cock through the nylon mesh. We passed beyond the point that Jenny and I had run, and the road began to get rougher. Finally we came to a steep canyon switchback and pulled into a small, unpaved parking area.

We collected our gear and headed down a faint trail toward the ocean. A few hundred yards later the view opened up to a small, secluded bay with a sandy beach. "I think this is it," Amber said with some doubt, since there was no one else there to give us a clue. We walked to the far left side of the beach and lay our towels out for maximum sun exposure. Amber quickly took off her hat, suit top and thong, handed me the tanning lotion, and faced me expectantly with her hands behind her head. Her tits jutted out, and I squirted lotion on them then rubbed all around, paying particular attention to her white parts and nipples. She turned and I repeated the process on her back and ass. Turning around again, she pushed me to my knees and said, "Now the rest."

I loaded my hand with lotion and rubbed it all over her smooth pubic area, up and down her inner and outer thighs. As I got lower, she put her hand on my shoulder and lifted one, then the other foot for me to finish. She turned so I could lather the backs of her legs. I stood to view my handiwork; Amber was now shining from head to foot. With her smooth pussy, she was a vision of sexuality.

Since I was now rock hard, I stripped out of my trunks to a girlish giggle. Amber grabbed the lotion and knelt on the towel to make sure my cock and balls were completely covered, then turned me around to knead my white butt. I think she took advantage of the situation because I felt her greasy finger slip in to my asshole at least to the first joint. I didn't object and may have even groaned, I'm not sure.

Our towels were side by side, and we lay down on our backs. Amber placed her hat over her face, so she was unaware when someone joined us on the beach. I was gazing at her, admiring that flat tummy and smooth pussy, when a movement caught my eye. A young girl was exiting the trees; she appeared to be in her twenties and was clearly a local. Her long dark hair was pulled into a ponytail. She automatically headed our way before she saw us; then must have decided that it would be impolite to turn around.

*****

Niki smiled at the cute haoli staring at her as she walked onto the beach. She expected to see someone here when she saw the convertible in the parking area. The man and woman clearly knew that this was a nude beach, since they both had taken off their swimsuits and were glistening with sunscreen. The woman appeared fairly young, but a straw hat hid her face. Niki was pretty sure the woman wasn't aware of her presence. The man was propped up on his side, casually stroking a nice-sized cock. She stopped about twenty feet from the couple and began laying out her towel. She wore a short wrap that she untucked at the top, revealing that she was completely naked underneath. Niki watched the man watch her as she laid the wrap aside. He took off his sunglasses to scan her up and down; her body was dark all over, with no visible tan lines since she came here at least twice a week. She knew that her breasts were fairly small, smaller than the other woman's, but she was proud of her dark, prominent nipples. When she wore a bikini, they always showed, making men think that she was constantly turned on—not far from the truth. Her sparse pubic hair was shaped in a small triangle above her shaved pussy lips. The man looked from her pussy to his companion's bare pussy, and Niki looked from his nice-sized cock to the woman's exposed cunt lips. She exchanged another smile with the man, and he put his finger to his lips to indicate that she should remain silent. Niki lowered herself to her towel; her feet were facing toward them and she held herself up on her elbows.

Niki gazed out at the ocean, trying to draw the man's eyes from her. When she looked back, she saw him continue to stare at her so she moved her feet apart allowing him a full view of her puffy lips. He began to lightly stroke the woman's upper thigh, moved up her torso along the side of her breasts, then down her arm. Reversing the path, he moved lightly back and forth, closer to her bare cunt and closer to her nipples with each pass. The woman responded with a moan; Niki traced a similar path on herself with her left hand. When he brushed the woman's nipple, Niki watched her reach up to pinch both to hardness, clearly enjoying his tickling. Twenty feet away, Niki did the same, pulling on her nipples to extend them to at least three quarters of an inch. There was a direct connection between her nipples and her pussy, and she felt her cunt contract and her juices begin to flow.

Niki was no stranger at playing with herself, and she particularly enjoyed it in public. The nude beaches on Maui generally were for sun worshippers, but Niki had found several opportunities to show off for friends and strangers. She looked around to see if anyone else was watching; it would be pretty obvious what was happening to anyone emerging from the forest.

The man saw her and smiled. He gently reached down under the woman's thigh to raise her leg, then pulled her knee toward him opening up her pussy. While Niki could only see the hairless pubic area of the woman's pussy, she slid her foot toward herself and moved her knee to the side to mimic the position; she felt her cunt lips part and the man could clearly see her clit and inner passage. He put two fingers in his mouth, wetting them thoroughly; Niki did the same. He ran them down over the woman's shaved tummy and dipped them into her cunt. Simultaneously, Niki slipped her two fingers into her wet channel.

*****

I watched the naked girl in front of me mimic my movements. She now had two fingers running in and out of her splayed cunt. Amber was moaning as my fingers tried to keep up with the island girl's. I leaned down and whispered, "My dare. Close your eyes. I'll take off your hat. Taste whatever I put in your mouth."

I lifted the hat and Amber had her eyes closed. Her lips were ready for my cock, but I had other ideas. I motioned for the girl to come over quietly. She removed her fingers and rose to her feet, walking the short distance between our blankets. I pointed to Amber's face and mouthed the word, "Sit."

*****

Niki stood over the couple. The woman had her eyes closed and mouth slightly open while the man was looking up at her with his fingers buried in his companion's pussy. The man clearly expected Niki to sit on the woman's face. Niki again turned to look across the small beach then mentally shrugged and stepped over the woman's head. She slowly squatted facing the forest with her back to the man and the ocean. Just before her open cunt met the woman's lips, Niki's scent must have reached her nose. The woman's eyes flew open and a squeal was muffled as Niki lowered herself the last inch. She looked down at the wide-eyed haoli, then back over her shoulder at her companion. The man was moving to position himself between the woman's thighs, lifting her hips. His hard cock was replacing his fingers as he knelt in the sand, and he entered in one push. Niki looked back down as she felt a tongue enter her vagina; the woman's eyes were now closed as she lifted her hands up to grasp Niki's hips. Following the woman's two-handed guidance, Niki began to lift and sway, rubbing her cunt on the woman's mouth. Occasionally she could feel the tongue poke at her asshole as she rubbed faster and faster. The woman was moaning from the pussy beating she was getting from her partner. Her hips were off the blanket, supported by the man's thighs. No words were spoken as the three began a steady sexual rhythm. The man would thrust, the woman would moan and lift her head, and Niki would grunt as the tongue would spear her. The man would pull out until just the head of his cock was encased, and the woman's tongue would retreat with Niki's juices. After several minutes, the woman clearly came first as her scream was transmitted directly into Niki's cunt, sending her over the edge as well.

*****

I held myself still as Amber's cunt milked my cock. It was all I could do to hold on as Amber clenched my shaft in a surprising rippling motion. This had to be one of the most talented pussies I'd ever experienced. I couldn't see her reaction—it was hidden by the heavenly ass cheeks of the young girl sitting on her face; but she continued to rotate her hips as her inner spasms gradually decreased. I reached forward and gently grasped the island girl's beautiful little tits to pull her back toward me. As she leaned against me, I could now see over her shoulder, and I looked into Amber's eyes. The girl's pussy lips moved away from Amber's face, dragging against her chin, and the glistening combination of girlcum and saliva coated Amber's nose and mouth. She smiled up at me and licked her lips.

"Aloha," I whispered in the girl's ear. "I'm Steve and this is Amber."

"Aloha, Steve. I'm Niki," she answered as I pulled lightly on her very prominent nipples, still buried in Amber's cunt. Amber ran her hands up Niki's body to dual with mine at those perky tits.

"You're my slave now, Steve," she reminded me as we fought to pinch and pull Niki's breasts. "You were bad and tricked me. I expected to taste your cock but instead got this," she emphasized by lowering her right hand to brush Niki's puffy pussy lips. "You're going to be a busy boy. I want you to roll over on your back; Niki is going to sit on your cock and I'm going to sit on your face. You are not allowed to cum until we have both cum twice."

Niki obviously didn't understand what was going on, so as I let go of her and got up to reposition a towel for myself, Amber quickly explained "My Dare" to her. When she mentioned that we had all met while staying at the same condo, Niki giggled and said that her brother was the maintenance man for the complex. "I'll bring him by; it sounds like you and your two girlfriends are going to wear something out pretty quickly," she stated as both women looked at my half-hard cock lying across my stomach as I lay beside them.

I shaded my eyes, smiled and said, "If your brother is as fun as you, I could use the help. I'm afraid I'm getting myself into trouble with this game. Now get me hard so I can make you girls come."

Amber and Niki quickly knelt on either side of me. Niki pointed my cock straight up and started licking it like a lollipop while Amber gently sucked on my nut sac. As I quickly hardened fully, Nikki bent to lick around the head of my swelling dick, tasting Amber's juices that had dried there.

Seeing that she was no longer needed, Amber moved up my chest with her kisses until her lips were plastered on mine. She was on all fours with her ass pointing up the beach, so I reached under her with my left hand to her hairless cunt and ran my middle finger through her folds, then slipped it easily in her fuck hole. With my right hand I moved Niki's ass so it was more accessible and found a similar target in Niki's saliva-drenched pussy.