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Meeting Leilani

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[ This story was originally submitted in 2012 for a contest. I recently removed all my stories but I have been convinced to return them for the entertainment of readers. I am not playing any ratings game or wishing to plagiarize myself.

Written by Sandra, the female half of a Literotica user-couple, in collaboration with and edited by Jack, her husband, this story is based on a true-life experience that occurred while vacationing in Hawaii. Few people would believe how much of this really happened.

© SandraMustard 2012 ]

The moment I first saw Leilani, she was admiring my husband’s stiff cock. Because of our lifestyle, like hundreds of women before her, the exposure was what my husband created and something I enjoyed witnessing. That had always been the extent of it, flashing his genitals to a woman; he gets off on it. If he gets really aroused by appreciative reactions, he comes to me for culmination.

I was his first lover. For over thirty years, I was his only one. Never had I known another man, neither had he plowed other furrows. I had only facilitated his flashing until the morning three years earlier when I stood naked on a third floor hotel balcony and masturbated for a stranger watching from below. After that, I was hooked on the naughty excitement.

All men are willing to observe my nipples or honey-pot but few women are voyeuristic enough to take sly, second looks after they recognize a penis is on display. My husband’s style is non-confrontational. Whether Popeye is peeking out of clothing or Jack is full monty, he makes it seem accidental or unexpected. He’s not something to gawk at in particular, only average at six-inches in length although slightly thicker than average, he’s half that when flaccid as most women first see him. Over decades of flashing, only a few women have openly acknowledged his exhibition … until we met this maid.

Vacationing in the Hawaiian paradise to celebrate our marriage, we had already practiced our exhibitionistic habits for ten days before arriving on the Big Island that morning. We had just showered in preparation for going out to dinner. Woody, the pet name I call my lover, had exited the shower shortly before me. As I shut off the water and stepped out, I heard his voice. Curious about whom he was talking to, I wrapped a towel around me and opened the bathroom door. There was Woody, standing bare-ass naked at the entry door talking to someone. Now, I have to admit to having an ass fetish and I particularly like Woody’s, but on this occasion there was so much more to see.

Woody was bent over slightly to keep his body behind the door while only his head peered around out into the corridor. It didn’t do much good though, thanks to the closet doors right in front of him that were all mirrored. Not only could I see his ass, I also could see his stiff cock in the reflection. The mirrors also allowed me to see past him to a beautiful girl outside the door. From the direction of her gaze, I knew she, too, could see a reflection of his cock and she wasn’t shy about looking at it.

My only thought was, why was Woody so woodie already? He wasn’t that way when he left the shower. Almost the same moment I saw all this, the girl spotted me behind him. As I asked Woody who was at the door, she moved forward, taking one last look at his cock of course, grabbed the door handle, and pulled it closed. This was already a good dick flash. A pretty girl had seen Woody’s cock and watched it get hard. I felt familiar warmth between my legs as my pussy anticipated taking in that hard cock, the usual by-product of his arousal. Yet, this wasn’t the end of the flash and this girl was going to see a lot more of his manhood.

Standing next to the door, we discussed what just happened while it was my turn to admire his erect penis. He told me she was the turn-down-service maid. I figured he knew she could see his cock but I confirmed it for him. Trying to analyze his arousal, I asked how long had she been at the door; it was less than a minute! I’ve watched Woody flash for over 30 years and he doesn’t usually pop a boner that quickly so I questioned him, why this time? He confessed that her beauty and attention to his cock aroused him that quickly. With all the attention my flashes were getting on our Hawaiian vacation, I thought Woody deserved more time with such a willing flashee so I told him to cover up as I reached for the door to try to get the maid to come back.

I presumed the maid had already moved on to another room so thought nothing of opening the door with Woody naked behind me. To my surprise, she was standing there as if she was waiting for me to open the door. She was so close, she had to have heard us discussing her looking at his cock. Poor Woody didn’t have time to scramble out of sight and I saw her look behind me. I glanced around and saw Woody, all ass cheeks and elbows, hustling to disappear around the corner.

Looking back to the maid, I realized this girl was a stunningly beautiful Hawaiian antalya escort native. Her badge provided her name, Leilani. She had to be in her early 20’s with dark native skin and beautiful white teeth. She was wearing some sort of a blouse mostly covered by a maid’s jacket and a black, mid-thigh length skirt. The work clothing was conservative but didn’t completely hide her sexuality. Her voice and mannerisms matched her beauty. I told her we preferred that she do the turn down service right then. She didn’t seem to be concerned about the possibility of a naked man in the room; rather, I sensed she was eager to see him again. She turned to gather some things from her cart and I returned to the bathroom for a towel for my wet hair.

Woody had purposely set up exposing his dick in the doorway. When he heard the knock at the door, a look through the peephole confirmed it was a maid, so he tossed his towel to the floor. When he scrambled away as I opened the door, he ran past his towel to the bed area. All his clothes, clean and dirty were in the bathroom or closet so he had nothing to cover himself with as that beautiful girl was walking in.

Most of his life had been spent scheming to be naked for situations with maids such as this yet he was too intimidated by the best setup ever to think clearly. Spotting a little paper napkin on the coffee table, he grabbed that. Can you imagine trying to cover an erect penis with a napkin, three-inches square? His phallus looked like a little bald man in a dinner jacket.

As I exited the bathroom, I looked over to see the young woman standing there laughing. She asked sweetly, “All covered now?”

“I’m sorry. Can I have my towel?” He spoke in a nervous pitch and pointed to it at her feet. She brought it to him and slyly watched while he quickly did his best to cover up. What the hotels call a bath towel barely reached around his waist without enough left to secure, requiring two hands to hold the ends barely touching. His pose resembled a naked matador with a white cape; only needing her shouting ‘Olé’ to complete the image; except, we weren’t in Madrid, this was Kona.

With a sexy voice that was hot enough to set his towel on fire, she said, “Don’t be sorry. You have a very nice pookey.”

“A what?”

“Pookey,” she repeated, pointing at what was trying to pull the towel back apart. It was obvious his cock was still hard as its shape pressed out against the towel. If I could tell, the maid could tell. Such a provocative hottie she was, flirting with an almost naked, older man while his wife stood nearby.

She took off her jacket, revealing a floral camisole top, and began turning down the bed. The thin top let her unhaltered breasts swing with her movements. Woody was standing off to one side, fearful of having an oopsie any moment. His tenting of the towel lifted the bottom upward, just about causing his balls to be visible; maybe that was why she seemed to look at him every time she bent down.

I figured I would encourage Woody by dropping my towel. Both Woody and the maid turned to look at me naked. I casually slipped on my robe and sat down. Woody still hadn’t let the towel drop and now the girl was working the bed right in front of him. Her ass was swaying just inches in front of the bulge in his towel. It sure looked obvious to me that the girl was making some extra moves to entice him. All he had to do was lean forward a little and there’d be contact. My exhibitionist husband, who has shown his cock to hundreds of women, was frozen like a statue.

The maid went into the bathroom and came out with a wet towel and the floor mat. She came over to where I dropped my two towels and picked them up. Seeing the opportunity to re-expose Woody’s erection to the maid, I said, “Here, don’t forget this one.” I grabbed his towel, with a jerk had it off him, and handed it to the maid. The maid and I again admired his cock standing so proud for us with a glistening drop of precum on top.

Looking at his turgid tool, the maid said, “I think he’s ready for you.” I thought her statement was interesting in that she didn’t consider this sexual display had anything to do with her.

I suggested, “He’ll probably pretend it’s you he’s balling.” She actually dropped her eyes in a demur expression of coyness.

“It’s okay, I’ll pretend he’s Tom Selleck,” I added.

“Oh, Magnum P.I. I loved that show,” she offered before stepping out to her cart.

The truth was my pussy was very much ready for Woody by now. I opened my robe and pressed myself against his naked flesh. Not because we needed any privacy, instead I wanted her to know that the erection she had seen was going to be fucking me the moment the door closed. As soon as she put the clean towels in the bathroom, I asked her, “Put the ‘Do Not Disturb’ sign out will you? Tom Selleck and I have some business to attend to.”

“Woody,” he corrected.

“Yeah, Tom Selleck’s woodie.”

The maid laughed, “You guys are crazy; but kemer escort so cool! Aloha.”

Indeed, we fucked like crazy. At the click of the latch, Woody spun me around and flung me down on the bed. He fell on top of me and with the precision of a pole-vaulter, slammed his love-rod deep inside me. In less than a minute, Woody was gushing out his cum inside me and waves of passion rocked my body. A good flash for Woody and a happy ending for me; but this wasn’t the end of our adventures with Leilani.


About the same time the next evening, I answered a knock at the door. It was the same beautiful girl. I keep calling her a girl because being fifty myself, her early twenties was less than half my age and younger than our own kids. Nonetheless, she was a woman in every aspect. Her body gave off a sexual vibe I could sense and her voice was soft but with an excited ring to it.

She looked into my eyes as she asked if we wanted our bed turned down but she seemed to be really asking if I wanted my husband turned on again. Intense arousal would be a problem this particular evening because I had just dressed for a lavish dinner. That night was our 30th wedding anniversary and we had reservations at the best restaurant the concierge could recommend. We did have a little time though, so I invited her in.

The turn down service consisted of pulling the coverlet and top sheet down, spraying a scented liquid on the bedding, then returning the bedding partly back up. Chocolates were placed on the fluffed up pillows and as an extra touch, flower petals dropped on the sheets.

Woody saw it was Leilani again and took a ringside seat, pulling up a chair close to and facing the bed. Did he want to watch her work or was he getting ready to flash her? Both, it turned out. He was at least modestly clothed this time, still in shorts and a shirt before taking his turn getting ready for our dinner.

I took the other chair and being naturally chatty, began to talk with the maid as Woody molested her with his eyes. She didn’t seem to mind, in fact, I’d say she was putting on a show for my husband. She had taken off her jacket and her half-unbuttoned blouse let her unhaltered breasts hang free to where even I could see her large, dark areolas; Woody of course was looking right down the groove. She also presented her ass covered in a yellow thong when she bent over right in front of his face. Woody’s shorts were bulging something fierce.

From our chat, we learned some things. She was 23, born in Kona, and lived there with her mom. She had a degree from USC (California), had worked as a dancer at the Polynesian Cultural Center (Oahu), and returned to Kona when her dad died. She was also a model on the side (I told you how beautiful she was!) where she made her best money but the maid work was steady income for paying bills; she liked the maid work and meeting people. We sure liked meeting her and watching her work! She learned we were there for our 30th wedding anniversary and about some of the things we did on our vacation, but not the flashing.

Her modeling? Well, it was clothing, swimsuits, nudie calendars… HUH? WHAT? We both perked up our ears at that and I pressed for details. She was on a “Girls of Hawaii” type local publication for the third year in a row. I made a mental note to pick up a copy if I could.

With our dinner reservation time fast approaching, I remembered the towel gathering that happened the day before so I sent Woody off for his shower thinking it might produce a flash opportunity for him. Just standing up became a flash as his cock was sticking out the leg of his shorts. I looked at Leilani as her eyes watched his cock leave the room. As she looked back and saw me watching her, she told me Woody was a sexy man. Don’t I know it! I wanted to acknowledge his arousal so I said he obviously got excited watching her turn down the bed. She admitted to being turned on by Woody so I had to trump her statement by admitting he’s been doing that to me since I met him and even now after 30 years of marriage. In fact, I felt my wetness dampening my panties.

Chatting another couple of minutes, I had stalled her long enough. When she asked if we needed fresh towels, I told her there were some wet ones in the bathroom. She smiled at me, as we both knew I was sending her into the bathroom to see my naked husband. I followed behind her to observe.

She opened the door and Woody was already out of the shower. She picked up the floor mat and the two towels I had used. She held out her hand and asked Woody for the towel wrapped around his waist. Of course, he was more than happy to hand it over. With his naked cock swelling before her, she turned and gave me a big smile as she took the towels to her cart.

When she returned with the clean towels, Woody was standing naked at the sink getting ready to shave. Leilani squeezed in right next to him to put the towels on the rack, konyaaltı escort which pressed her ass against his hand at his side. Woody looked down and pushed his hand up under her skirt and between her legs. She was up on her toes to reach the rack and her legs were spread allowing his hand room to reach her tender parts. Watching my husband feel her up, I was getting intensely aroused despite this bending of our rules. I looked up and saw her eyes were closed as she slightly rocked against the touching. With a little sigh, she stood down and turned toward the mirror. Woody was now standing between Leilani and me with a very impressive erection oozing precum. I know he wanted either of us to grab his cock and jerk him off but we were running out of time.

Leilani spoke first, “He looks so hard! I guess Magnum is ready for you again.” Was it part of her maid service to turn him on so I could have a good fuck with him? It was a service she performed very well. Only our restaurant reservation kept me from climbing onto my man right then.

The maid left with “Have fun you guys. Happy Anniversary. Aloha.”

Woody was literally shaking as he held his razor to his neck. “Don’t cut yourself,” I warned. “She really turns you on, huh? I bet you would like to fuck her.”

Thinking about thirty years of faithfulness with what he considered a wonderful and sexy partner, no fleeting moments with even a beauty like her would be worth the trade. He truthfully answered, “No, but I sure would like her to see me cum; maybe watch her cum.”

“You better say no,” I declared in mocking possessiveness. I stayed there about twenty seconds in deep thought. Thinking about my lover’s sexual desires, I knew that Leilani was just the woman to make his dream come true. It suddenly occurred to me to try to arrange that very encounter. I grabbed the ice bucket as if to fill it and left Woody to finish getting ready.

Leilani’s cart was two rooms down. When I walked into the room, she seemed surprised that I wasn’t taking care of Woody’s woodie. I talked fast and nothing seemed to shock her. I explained how we got off on exposing ourselves to strangers. Then I mentioned how Woody’s fantasy was to cum for her and watch her cum. Would she consider acting out something like that for say, a $100 tip?

Her smile told me that my request was not out of line. I mentioned that I wanted her to get naked and masturbate to orgasm while Woody did too. Her next statement set me back a bit. She asked, “After that, can I fuck him?” I think my mouth hung open in shock. I wasn’t sure how my strange request was going to be received, yet there she was three steps ahead of me, eagerly requesting permission to have intercourse with my husband. I clarified that I wanted no actual sexual contact. I explained that through 30 years of marriage, we have never had other partners and this was not the time to start. She seemed disappointed and I wondered if I could trust her. I relaxed when she said, “Okay, I can accept that.”

Next was the problem of when to have this encounter. She was off for the next two days and didn’t work until Monday, our last day on the islands; we’d be gone before late afternoon. She didn’t really want to do this sort of thing while working anyway so she came up with the idea to come in on Sunday before the regular maids showed up. She would be dressed as a maid and have her stuff so Woody wouldn’t know it was a setup. We set the time for 4:00 exactly.

I got some ice before returning to our room to have an alibi but Woody never questioned my absence. During dinner, I was a bit distracted by my thoughts of what would happen Sunday. I have had many sexual thrills after watching Woody flash someone. My balcony flash was such an incredible experience, too, when it led to wonderful love making with my husband. I loved Woody very much and wanted to make this a very special moment like that for him. I actually briefly considered letting him screw her but I decided that it was something that Woody would not really like to do.

The next day we shopped for the calendar with Leilani in it. We had to ask for it because they kept them with the girlie magazines behind the counter. It was wrapped in brown paper too, but we opened it right outside the store. There she was! March, I think. I noticed a small tattoo of a flower on her left breast that neither of us noticed when perving down her blouse. Distinctive tattooing on her shoulder and arm we had seen confirmed her identity.

Such a beautiful creature she was in a seductive pose with her sultry eyes gazing into the camera. Her hips were angled to her right and her left leg flexed enough to hide her labial cleft just below a small strip of pubic hair. Woody’s breath was beginning to pant, probably thinking about having this beauty next to him bantering about his cock the night before. I glanced down at an unmistakable bulge stretching out in his shorts. Discreetly pressing the back of my hand against his erection, I asked, “Wouldn’t it be great to slip your dick into that?”

After an obvious swallow to open his tight throat, he hushed, “Yeah.” Always honest, he felt comfortable enough with me to admit his lusty thoughts. I wasn’t insulted or troubled by his answer; I had suggested it, after all.

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