Ashley – Part I, The Bet

By Woody

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Tags: wife, reluctance

Added: 29 Dec 2008 Views: 30978 Avg Score: 4.67

Part I of a four part story about my wife



I have been an anonymous reader of stories on this site for a long time and have really wanted to try and be a contributor.   But I’m afraid my imagination isn’t as developed as many of the really good writers here.   So for the past few months I’m very writing a story that is pretty much autobiographical.   It probably isn’t as good or as adult as most entries here.   But it has the benefit of having taken place.


A couple of other notes…   First, since it was so long I broke it up into four parts so people won’t get bored.   Second, I have no idea how to write dialog, so forgive my way of handling conversation.   Finally, this is my very first effort at writing something so I’d very much appreciate any feedback, both positive and negative that readers can give me.   I’m interested in constructive criticism on the story and the writing.


And lastly, if you take the time to read it all through, thank you very much.   Eventually I will share all the comments with Ashley.  Here goes...



I’m 38 years old and have been married to my wife Ashley for 13 years.   I love her very much but I have to say that when it comes to sex she is a real prude.   She was raised a strict Catholic and based on her upbringing she’s always been very modest and perfunctory when it comes to sex.   Until the following took place, no matter how hard I tried over the years to bring her out of her shell, it simply hadn’t worked.


To give you a better idea, I had never seen her completely naked.   She has insisted on always changing in the bathroom and whenever we have sex the lights had to be turned off.   Even at the beach or a pool she has always worn a full one piece suit with a skirt.   So all I have had over the years were glimpses here and there and shadowed views of her chest or rear end, mostly hidden by clothes, towels and covers.   In some respects it has kept things mysterious and interesting.   But at the same time being the guy I am, it’s driven me nuts because I’m a very visual person.


To compensate, over the years I have taken to occasionally visiting strip clubs.   I would never cheat on Ashley but there is something about seeing a live naked woman that I really enjoy.   And since she wouldn’t satisfy that need, this is one way I have compensated.   I’m also a secret connoisseur of on-line porn.   I really enjoy the amateur sites where regular women either show off or are caught unaware.   For whatever reason, it’s just much more interesting to me than seeing “perfect” professionally posed models.   I guess I’d rather see a natural woman with whatever imperfections she may have.   To be honest I had even thought about setting up a secret camera and trying to get pictures of Ashley… but I couldn’t bring myself to be as sneaky as that.   So my curiosity about my wife was maddening.


In all other respects Ashley is very normal and a terrific wife.   As it turned out we couldn’t have children so she has kept a good figure, at least as much of it as I’m allowed to see.   She has brown hair, brown eyes and wears glasses all the time.   She has a very pretty face and she lights up a room whenever she smiles.   She’s about 5’6” and I would guess weighs about 125 pounds.   But mind you, that’s just a guess as she would never tell me.   She has a very cute bottom – this is what first attracted me to her.   I can’t get enough of watching her when she wears tighter pants.   Her legs are shapely and I think she likes showing them off a little when she wears dresses… which I enjoy seeing as well.   Her breasts are not large but based on touch; I can tell you that they are firm (okay, I checked her bra and the size is 33B).   They hold up nicely on her chest but then again, it actually could have been her bra providing the support as far as I could personally say.


Without kids we have been great friends to each other.   We talk about all kinds of things.   She shows interest in my job, we follow sports together and both love the outdoors.   She not only works part time but she takes care of the house and cooks fantastic meals.   Except for her one idiosyncrasy, I really couldn’t ask for a better wife… which is why I have tolerated it.


Ashley is also very competitive.   We often have harmless bets with each other about all kinds of things just to make life a little more interesting. I don’t even remember how it started, but over the years we have bet on everything from the weather to sports and politics (she was a big Hillary supporter).   We’ve even bet on as silly a thing as whether the next person coming out of a restaurant would be a couple, a man, a woman or a group.   Most of the time the betting is just for fun.   But occasionally we have bet with things of real value at stake.   I’ll give you an example.


A few years ago we started planning our annual vacation.   I wanted to go to Las Vegas and (don’t ask me why) Ashley wanted to go to Minnesota and the Mall of America.   For whatever reason we couldn’t find any common ground and the discussion went on for weeks.   Finally Ashley suggested settling the issue with a bet.   I was pretty wary because I had no interest in the Mall of America.   So I told her I would only agree after seeing what the bet was.


For two weeks we each suggested various bets with both of us finding reasons to reject the others’ suggestions.   I finally came to a situation that was acceptable to both of us.   It was the 2002 Super Bowl, the Patriots vs. the Rams.   Ashley grew up in New England and loved the Patriots, who were big underdogs.   As I recall, they had never won the Super Bowl and the Rams were the heavy favorites.   Although not a Rams fan, I thought it was a sucker bet even giving her 7 points when Ash agreed to it.   Of course to my chagrin the Rams lost.   Ashley was ecstatic.   I tried my best to get out of it but she was adamant.   Not only were we going I would have to put a good face on it and not complain or be any trouble or problem on the trip.   So I swallowed my pride went to the Mall of America and made the best of it (by the way, it was excruciating!).


Since then we have had bets with stakes on a few things, usually bigger items we can’t agree on.   The worst was a bet over a local election that resulted in me having to replace her car.   Now she was going to need a replacement eventually, but by my reckoning it was at least two years early.   I won a few along the way as well (I have a nice Seiko watch to prove it) but the vacation and the car were always the two big ones.


That is until this past year.   Ashley had been pressing about moving into a bigger and more modern house.   We’ve lived in the same house since we were married.   It was originally a fixer upper that I have worked on extensively over the years.   It’s very comfortable now and I like it here.   Besides, I put a lot of sweat equity into it and I’m proud of all the work I’ve done.   But Ashley wanted to live in a more upscale neighborhood with bigger houses.   I flatly refused, in particular with the economy the way it’s been.   Although we could afford to move, I also knew we would never get the value for our house that I felt it was worth.   But Ashley kept pounding away and candidly it started to get annoying.   When she finally offered to bet on it, I got an idea….


Before agreeing I wanted to take some time to make sure I optimized my idea.   I knew instinctively that the longer I waited, the more anticipation would build in Ashley and the better chance that she would agree.   And I didn’t want to take the chance that she would simply decide not to bet - plus I had to make sure I had the right bet.   While I was thinking and planning I caught a lucky break.   Due to a foreclosure, a house that Ashley loved came on the market and she became frantic that someone else would get it.   So I decided the time was right to make my proposal.


One evening over a glass of wine I told her the stakes that I would agree to.   I told her that if she lost she would have to agree to the following.   First, I would get to see her naked in full light from now on and on a regular basis.   This meant changing in the bedroom as well as lights on during sex whenever I asked.   Second, I would be allowed to take digital pictures of her naked to do with what I wanted as long as I didn’t publicly expose her.   And finally, in order to make up for all the years I hadn’t seen her, she would agree to go with me to a hotel and let me take pictures of her naked in public areas to prove that she was over this phobia.   We would try to do it when things were quiet and she wasn’t seen, but she’d have to endure whatever unfolded.


After letting me explain the stakes (with Ashley blushing and shaking her head the whole time) she stated simply that this was absolutely out of the question.   This was a personal matter for her and there was no way she would agree to it.   We would simply have to find something different to bet on.


I laughed and told her that when it came time to consider selling my home and handiwork, these were the only stakes I was willing to discuss, after all I was her husband.   A few tears slipped from her eyes and she got up from the table, her wine unfinished.   She didn’t speak to me for the rest of the night.   I of course wondered if I had overplayed my hand.


After two days of walking around on tiptoes she called me at work to ask me if I had changed my mind.   I told her firmly that this was as important to me as the new house was to her and that I had definitely not changed my mind... nor was I about to.   The phone was silent for what seemed like five minutes.   Then in a quiet voice she told me that an offer had been placed on the house and would I please, please reconsider?   I again told her I would not and the call ended abruptly.


That night over dinner she told me that the offer had been rejected by the bank.   But the real estate agent told her there were two other interested parties who would both likely place offers in the next couple of days.   I simply shrugged my shoulders at the news.   After a long pause she asked what it was we would make the bet about if she actually agreed to the terms.   I knew then that I had a chance.


The bet clearly needed to be a quick one because the results were needed in time to deal with the house.   As it turned out, the next evening was game 7 of the playoff series between Ashley’s .beloved Red Sox and the Tampa Bay Rays.   The Red Sox were World Champions with a long history of success and the Rays had never even been in the play-offs.   Ashley suggested betting on game 7.   I agreed because simply getting her to agree to the stakes I had proposed was a victory of sorts – I figured that even if I lost, moving was not a disaster and now I had opened up the subject of Ashley’s modesty for future opportunities.


The next night we were glued to the television set.   The Red Sox jumped out to a quick lead with a home run in the first.   But the gods were smiling on me because in the end the Rays won and the bet was over.   Ashley sat there looking pale and shaken.   I honestly believe that she thought there was no way she could have lost as the Red Sox had made a habit of exciting, come from behind wins.


In a shaky voice she asked if because it was so late and she still needed to get used to the idea, could she have a few days before she would have to start paying off the bet?   Smiling I told her that for sure the pictures and the hotel could wait.   But I had known her for 15 years and waited that long to see her naked and I wasn’t going to wait any longer.   I have to give her credit because then she swallowed hard, got up and headed to the bedroom.


I followed her in and watched while she drew the shades and got out a nightgown.   She had only turned on her beside lamp and she groaned loudly when I turned on the overhead which added a lot of light to the room.   Then blushing heavily she started undressing.   I don’t think she noticed it because she was so conscious of herself, but I was sporting as hard an erection as I have ever had in my life.


She started by slipping off her shoes and then flinging her little half socks off each foot.   Then glancing at me nervously she unbuttoned her jeans, slid them down her legs and stepped out of them.   She stood there in her top and panties and again asked if she could stop.   I simply said three words to her…


Mall of America.


Hearing those words she paused and then I reminded her that as it had been with me, attitude was just as important as compliance…


She sighed heavily again, gave me a wan smile and pulled off her top.   She was wearing a modest bra that covered her chest.   But I had eyes only for her tummy and navel which I had caressed in the dark many times over the years, but never seen.   I looked up at her face and she was blushing bright red.   So I gave her a real smile and in return she reached up behind her and unclasped her bra.   Then leaning forward she shrugged the straps off her shoulders.   For a minute she held the cups over her breasts and then slipped the bra off and stood there topless.   I stared at her breasts which stood out from her chest with just a hint of sag.   There we not very large but they were gorgeous, topped by medium sized centered brown nipples which were erect.   If anything her blush just deepened.


She stood there for a minute or two and then clearly working up the courage, bending over she slipped her panties down her legs and straightened up.   I looked between her legs and for the first time ever, I saw her pussy.   She was standing modestly so to be sure all I really saw was the neatly trimmed top of her bush.   But it was more than I had seen in the light before and it was beautiful.


I looked at her naked body as if I were a blind man who had received the gift of sight for the first time.   In a way it was true because for our entire married life I knew her body by touch only.   She was a feast to my eyes.


She started to reach for her nightgown and as I held up a hand she paused.   I asked her to turn around so I could see her back.   Slowly and somewhat reluctantly she obeyed.   Her back was virtually flawless.   Her skin looked as smooth and touchable as it had ever felt.   I saw the small mole below her left shoulder blade that I had known only by touch.   Her back tapered at her waist and then flared into her beautiful bottom.   Her cheeks were symmetrically rounded.   My eyes traced the cleft between them down, down and maybe it was my imagination, but I thought I could see a small tuft of hair… but I couldn’t be sure before she turned back around and hurriedly grabbed her nightgown.


I quickly stepped across the room, took her into my arms and kissed her.   Then picking her up, I placed her on the bed and switched off her table lamp.   I crossed the room, turned off the overhead.   Then in the darkened room I got into bed and made gentle love to her.   Although I know she was embarrassed and horrified by what she had just done, she was more excited than I have ever seen her and the lovemaking was just amazing.