You Win Some, You Lose Some

© 2001 Max (aka Max O'Drive, Maximum Overdrive). As a copyrighted work, this story may not be reproduced in any media format, physical or electronic, or reposted at any other website in any form without my express written permission. Permission to print this story is granted with the provision that it is for personal use only. Requests for reprint or reproduction other than the exclusions above may be sent to the email address in my profile.

I'd like to thank a lot of people for helping me with ideas, concepts and support as I wrote this. Some people were more influential than others, but many, many people have contributed to this story. Far too many to list here, otherwise we'd be here all day.

I do want to express my gratitude to my "first readers" who were kind enough to read the first drafts of this and tell me which parts realllly sucked! *g*

Special thanks to: Babs, Bill F. and Ghia for taking the time.

Extra special thanks and a big *SMOOCH* to Babs for her editing skills and her patience with me as I meandered my way through this story.

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Try And Fail

"No, Tom. I don't want to do it. Who in their right mind beside some pervert would want to have sex with another man's wife while he watches?" the lady sitting behind me said.

Needless to say, the manuscript I was reading didn't have quite as much appeal as that conversation did. I was sure she was quite embarrassed at her outburst, quiet as it was, and would now be looking around to see if anyone heard, so I remained motionless.

"Look, I know it's a fantasy of yours," she continued, heatedly. I took the opportunity and shifted around in the lounge booth placing my back against the wall, which would let me easily look at them if I turned my head. I moved the 'script so it could be easily seen if anyone looked over to me, masking the fact I was listening intently to the couple talking.

She finished her point by saying "But I just don't think its possible, for one thing and I'm afraid of what it'll do to us if I do"

I glanced up over the pages at them. All I could see of her was a willowy mane of brown hair and her slim arm as she tipped her wine glass up to take a drink. He was a nice enough looking man. Sandy hair with touches of gray at the temples, wire-rim glasses, healthy looking, about my age I assumed. He had a slightly pained expression on his face, which was easily explained by his wife being less than eager to satisfy his fantasy. "Den, hon, I've told you before that this won't mean a thing to us. Well, it will, but I feel it'll make us stronger and happier."

I figured if I was going to be a part of this, now was the time to speak up. Looking over the top of their booth, I said to her "He is right, you know."

He looked at me with mild surprise, but when she turned around it was almost like seeing a deer caught in car headlights. And, the longer I looked in her face, the better that analogy fit. Soft, brown eyes are what I noticed immediately, and I noticed how pretty her face was framed by that mane of brown hair. Then I noticed her lips. Even though her mouth was caught open in a small "o" of surprise, they were full and pink. If she was wearing lipstick, it was just a clear gloss. All I could do for a moment was just look at her and be mesmerized with her natural beauty. She had the kind of beauty that wouldn't be touched by age, so I couldn't even begin to guess at how old she was. If pressed, I'd have to say somewhere between 20 and 60.

"How dare you…" she started as her face clouding with anger. "Shhh.. " I said. "It's ok. I'm just a friendly face with a bit of knowledge on your 'topic' for the evening"

"I know it's rude to eavesdrop," I continued hurriedly before she could get started again "but I couldn't help it. You see, you and your husband are having much the same conversation my wife and I had just a couple of years ago…." Den's husband was looking at me with sharp interest, and I could see her eyes soften again as she realized I wasn't a threat. I looked down for a second, which placed the manuscript under my gaze, so I closed it and put it on the table beside me. Looking back at them I said, "Hopefully you can understand better than Andy could. Hopefully you can be more accepting of how your husband feels than she could." I shifted a bit more, turning about as far in the booth as possible to face them. Sighing, I continued, "You see, she divorced me shortly after that talk we had. I couldn't find the words to explain my feelings well enough so she could understand. Since then, I've talked to a lot of people and been to a lot of websites and found how to explain those feelings now. Maybe, if we talk a bit, we can keep your marriage from falling apart. Maybe, if things go well, we can satisfy a fantasy, or even create some new ones."

I could see they were taken aback by my approach, but given the circumstances, I could understand. I figured I'd better back off and give them some space. "Tell you what," I said, picking up my work and scooting out of the booth. "I'm in room 618. If you want to hear my story, and if you want to understand your husband better, come talk to me. I'm in town for a signing, and will be here for a few days. Please, stop by tomorrow evening. I'll be there." At that point, I turned and walked away. --------------------------------------------------

Accept Limitations

I was riding the elevator back to my suite, my mind racing. Old, painful memories from the past came boiling up in my mind. Doubts about why I'd stepped into the situation between Den and Tom mixed with the memories to confuse me even more. But, the calmness of the words and lessons I'd come to understand began to make order from the chaos. By the time I'd gotten back to my suite, I knew why I'd intervened and why I wanted this young couple to succeed.

I didn't know if they would come find me, but I really hoped they would. I knew if someone had made me an offer like that three years ago, back when Andy -- Andrea -- and I were still together and I'd begun to talk about wife sharing, I'd have jumped at the chance.

Unbidden, images from a happier time for us came into my mind, causing me to smile ruefully. Images of Andy and the good times we had. She was definitely a sexy gal. Still is. Blonde, blue sparkling eyes, a naturally slim and trim body that golf and working in the flower garden had made tan and lithe. Legs for miles and a smile that I loved to see in the mornings. Or at night. Anytime at all. I'd be writing in the study, and would stop so I could watch her through the window as she worked in the flowers. Just so I could see the sun highlight her hair. See her shorts pulled taut over her sexy behind. See the light sheen of sweat on her arms and legs. Watch her face brighten with that amazing smile when she'd catch me.

My musings finally caught up to the fateful time when I first brought up the subject.

One afternoon after a fairly productive morning, I'd stopped to stretch and think through a scene. I walked to the window to look at Andy's garden and saw her working away in the flowers. She looked beautiful out there among the roses and philodendrons, the peonies and daises. Mother nature dressed in a red midriff shirt and tight blue jean shorts. She caught me looking, as she usually did, and wiggled her behind at me. I grabbed my crotch (rude, I know, but she always laughed when I did it). She laughed that time too, and then did the "come here" thing with her finger. I smiled and made typing motions, but she shook her head and motioned me to come out. I nodded and went out the doors to the balcony to join her.

I looked over at the neighbor's house and saw a guy cleaning the pool. I couldn't tell for sure, but from the balcony, he looked to be either Hispanic or Latino. We have a wrought iron fence between our properties. When it's grown up with vines and ivy, the fence makes a pretty good privacy barrier, but there was a clear view of our neighbor's property from the balcony. I'd often watched some of the antics their son and his friends pulled in that pool.

As I stepped down to the garden, I asked Andy "Now just what is sooo important that I have to come all the way out here?"

"Well," she started, taking off her dirty gloves and dropping them on the ground beside her, "I thought you may want to take a look at something interesting." I took a 'patient' pose, cupping my chin with my hand and asking, "Oh? What would that be?"

"Just this," she grinned, pulling off her cropped t-shirt with one quick motion, her breasts bouncing a little as she did.

Matching her grin, I reached out and fondled them, loving the warmth and smoothness of her skin. I said, still running my hands over warm, soft flesh, "Oh, yessss. Very interesting! I like these a lot, but what are these things?" I teased, tweaking her nipples.

She responded, giggling, "Magic buttons! They get bigger as you play with them."

"Really?" I asked, grinning, "I've got something that gets bigger as you play with it too. Wanna see it?"

"Mmmmhmmm," she murmured, reaching down and rubbing the front of my pants.

Kneeling down on the brick path, she unzipped my fly so she could get at my cock, taking me deep into her mouth as soon as it was freed. Working on me for just a couple of moments, her mouth sucking me hard as she moved her head around, she had me hard as a rock. She deep throated me and held it, her eyes looking at mine as she hit bottom, then she slowly sucked her way back to the head. Biting lightly to kill the orgasm she knew she'd almost caused, she stopped and announced, "I'm a cupcake."

I grinned at the Alice in Wonderland reference and replied, "I'll be happy to eat you, little girl."

She grinned back and stood up, snapping the button of her shorts loose as she did. Stepping out of them, she walked to a flat concrete bench just a few feet away and sat back on it, spreading her legs and putting her feet on the bench. "So, come on, Mad Hatter. Let's have a tea party."

I pulled my shirt over my head, kicked off my shoes and removed my pants. "Cool! Lets PARTY!" I grinned, doing my worst John Travolta disco bop. I sat down on the warm bricks and leaned my face into her pussy, inhaling her musky scent. I "Mmmmm'ed" then leaned closer to lap at her already wet slit.

As I started licking around the lips, and then tracing the outline of her vulva with my tongue, she started to squirm. I dipped into her slit, tasting her salty muskiness, then licked upward to her clit. She was really hot that day because as soon as my tongue touched her clit, she gasped and moaned loudly.

Pressing my advantage, I reached up and fondled her breasts, then moved my hands down to hold her open so I could probe deeper with my tongue. Alternating that action with attention to her clit soon had her moaning almost constantly. After a few more moments, I was rewarded for my efforts when she came. Her pussy spasmed under my tongue and her juices were flowed freely, leaving a wet spot on the concrete bench.

Sighing softly as her orgasm passed, she turned to the side and lay down on the bench, her pert nipples sticking up in the warm breeze. I grinned, and then walked around to her head. Kneeling down at the head of the bench, I grazed her face with my somewhat softened cock. She grinned and opened her mouth, so I took the opportunity to place the head of my dick in it. She slid back so I could move back and forth in her mouth without having to half stand to do it. I started rocking back and forth a little, loving the view of my cock disappearing into her mouth, then back out again.

Over near the fence, I heard a noise that sounded like a squirrel in the brush. I glanced that direction, but didn't see anything until I heard the sound and glanced over again. The guy that had been cleaning the pool next door was watching us through the fence! Turning my head the opposite direction, then back to where I was softly face-fucking Andy, I thought quickly about what to do.

I decided not to do anything at the moment and let the man enjoy his voyeurism. Andy sometimes enjoyed a bit of exhibitionism and had flashed me several times in stores and in the parks and had even let me expose her a bit while we were in restaurants or while dancing. But there were times when she hated being seen naked. I was hoping since she'd initiated sex outside that she was in one of her 'show-off' moods, because right now she was showing off whether she wanted to or not.

My cock certainly knew what it wanted to do. Catching the guy peeping at us had caused it to become rock hard, and it was ready to go to work! I popped out of her mouth, walked around to kneel on the bench and popped back into her pussy. She gasped, then wrapped her legs around my back as I started fucking into her, my strokes alternating between long, slow strokes and short, hard ones.

"MMMmmm! Baby!" she said after only a couple of moments. "Oh, yes. Fuck me…"

I obliged, starting into a long series of the short, hard thrusts to which I knew she'd respond. "You love getting fucked, don't you, babe," I asked.

"MMMmmhmmm!" she moaned.

Still pumping away I continued, "You love a cock in your tight pussy, right?"

"Ohh, yesssss," she hissed.

"You love knowing guys want to stick their dicks into you, don't you?" I growled

She started rolling her head back and forth as she felt her orgasm begin to build "Ummmmmmmmm!" was all she could say.

I began alternating words between quick, short strokes. "Big" stroke "hard" stroke "dicks" stroke "fucking" stroke "your" stroke "hot" stroke "wet" stroke "cunt!" stroke.

"Uh-uh-uh-uh!" she grunted then. "Ohhhhh!!!!!!" she cried, her orgasm starting when I said the word "cunt". Her legs clamped hard on my ass, pulling my dick as deep as it would go into her, the walls of her pussy grabbing my cock and pulling me in even harder.

I continued to stroke in and out of her pussy, but with long, easy strokes after she stopped cumming. She relaxed her legs, and sighed, reaching her arms over her head as she let the tension flow from her body.

"You like that, don't you" I asked, grinning.

She grinned back. "No. Not a bit." Then she laughed. She knew it was a favorite fantasy of mine, although we'd never seriously discussed it. I'd talked about how she liked other dicks for years, and had even talked to her about it a couple of times, but she'd never taken me seriously.

I pulled out and instructed, "Ride me."

Grinning, she stood up while I sat down on the bench. She started to mount facing me, but I turned her around so she faced the fence… and our voyeur. I could see him and, from the way the vines were moving, he was jacking off watching us.

She settled onto my cock, and then started moving up and down on it. I leaned back a bit, letting her squat up and down for a bit and then suggested that she'd be more comfortable if she'd sit on me. I scooted back on the bench. We got arranged, which left her legs spread widely, her upper body leaning back on her arms and my chest. This way, she was lewdly on display, my cock easily visible in her pussy to the pool man's gaze.

This position let her ride me easier, and I could rise up and meet her thrusts. She started panting, short sharp gasps and the exertion and the sensations of riding my cock began to have their combined effects. I leaned forward more so she was literally sitting on my lap with my cock buried inside her. This left her without having to support her upper body, and only having to move up and down just a bit to meet my upward rising cock. Over and over again we moved this way, my cock glistening with her juices in the afternoon sun.

I could feel her starting to tremble, and could feel my own orgasm building in my balls. I started to taunt her again. "Big dicks get you wet, don't they?"

She "Mmmmm'ed" a reply as she rode me faster.

"You like showing off for guys so they can see your horny cunt being fucked." I growled.

"Oh, Godddd," she moaned, her trembling more pronounced. "You'd love to know someone was seeing me fuck your pussy now, wouldn't you?" I asked, a deep husky tone in my voice.

She started hammering hard onto my lap as I shoved upward into her. "Yesssssss!" she hissed, her shaking even more pronounced.

Just as her orgasm started, I told her, "Look at the fence. Over by the begonias."

Her eyes popped open as she saw the man watching her cumming on my cock.

She let out a little squeal as the orgasm peaked and her realization that she was being fucked as someone else watched hit at the same time. Her body shoved itself down hard in my lap, causing me to cum into her fiery inferno of a pussy, blast after blast of my cum pouring into her.

Trying to scramble up, I reached around and held her in place as my own orgasm slammed its way through my system and out my dick. I laid my head on her sweat-covered back as I started to relax. She felt my arms loosen, stood up and walked quickly to the house. I retrieved our clothing and followed her. I'd barely walked in the door and laid the clothes on a table when she turned around and slapped me.

Oh, she was mad! Why hadn't I told her that guy was watching? I tried to explain about the fantasies involving her and how he'd just happened to be there. How I thought she wouldn't mind since she'd exposed herself before. How I enjoyed the exposure. How much I'd love to turn the horny talk of other guys into something more real.

I tried to find the words to tell her how turned on I felt knowing another man was seeing her -- enjoying her sexy beauty -- as only I had before. Then I did something that to this day I regret. I told her that the only thing that would have made the whole incident even better was if I could have watched that voyeur pleasuring her as I had. Instead of paying heed to the clues and stopping like any sensible man, I kept babbling about how I knew that a woman can last much longer than any one man and how I wanted her to experience her sexuality to the fullest -- being completely and thoroughly satisfied. I guess, looking back, it wasn't a big surprise when she then really began laying into me, telling me that I was insensitive, a bastard, a macho asshole, and other names which I have conveniently erased from my memory.

After that I never could find the right words to say about anything. Frustration led to arguments and arguments usually meant somebody left the house. We'd shared some good years together, shared many happy times. In spite of this, the troubles and misunderstandings had taken their deadly toll on our relationship. The last time she left without saying a word, and I haven't talked to her since. I suppose she felt she had to do things that way so she could find a new perspective and until she was ready to talk. Anything I had to say would only make matters worse.

It took a bit of time, a lot of study and some hard thinking but I reached the point where I was comfortable with what I'd learned. I felt I was finally able to make sense of what I'd done wrong. I was hoping that Andy was sorting through the events too and sometime in the future we could sit down and resolve things. I hoped that she'd realize we had both made mistakes and could come to a point to where we would forgive each other. At least talk so we could work things out. Whether we are ever able to now is totally up to her.

"Ah, such is life…. " I sighed to myself as I came back to the present. I didn't want what happened to Andy and me to happen to Den and Tom because I knew the pain could be prevented. It may or may not be too late for Andy and me, but with the lessons I'd learned I could try to help Den and Tom communicate with each other. I could mediate so they could better understand their own feelings and the other's feelings as well. Maybe, with any luck, I could guide things to a happy ending for them. I knew I wanted to try. --------------------------------------------------