Indecent Proposal

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Older man helps younger woman and receives unusual proposal.
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After a day of meetings, I arrived in the office late afternoon and had barely sat down at my desk when Dione, my chief financial officer walked in and closed the door behind her. That immediately set off alarm bells. I don't hide things from my employees, many of whom have worked for me for a long time, so I rarely have closed-door meetings. When Dione sat in the chair opposite my desk, that was another alarm bell and I really started to worry about what was wrong. Dione started off as my executive assistant and was my very first employee. Even though she has been happily married for a while, we have history and she likes to flirt so usually she would have perched on my desk, so I could get a good view of her long, perfectly shaped legs in fishnet stockings and four-inch stiletto heels.

"What's wrong? I said.

"It's Kelly," Dione replied. "In the last two or three days we've received six requests to garnishee her wages. The companies making the request won't tell me anything, privacy of course, but given the amount of money she makes, she's obviously in deep trouble financially if she can't keep up her payments."

"You're dead right. Kelly is the best sales person we've got so and between her base salary and the commission and bonuses she's picking up, she's got some sort of major problem if she can't pay her bills," I said. "She may just be living beyond her means, but she could have some sort of major problem and need some help. Bottom line, we need to find out what's going on."

"She certainly is a great sales person, one of the best I've ever seen," said Dione. "But right now, what are we going to do?"

"Is there any sort of mandated response time for these garnishee requests?" I said.

"Yes, once a company receives a request the garnishee should be in place by the next pay cycle unless it's received less than a week before pay day."

"OK, that's good," I said. "Everyone has just been paid so we've got the best part of a month to sort all this out."

"What are we going to do?" Dione asked.

"You need to give me the garnishee notices and I need to talk to Kelly to try and find out what on earth is going on."

"And then?" Dione said.

"It depends on her attitude. If she takes responsibility for what she's done and asks for help then I'll see what I can do to help her. If she doesn't, then we'll just put through the garnishees and monitor her performance closely."

"I thought you'd say something like that," Dione said. "You're a good man, James."

"It's the fair thing to do. We don't know what's behind her financial issues. It could be sheer recklessness but there could also be some major challenge she's going through that she hasn't told us about. I think Kelly has almost as much potential as you and my investment in your development over the years has paid off rather well."

"You say the nicest things," Dione said as she bent over to kiss me full on the lips before heading out the door.

What in the hell was that about I thought as I watched Dione's perfect ass and legs walk out the door. Dione and I have history, but she hadn't kissed me like that in years.

When I first put Dione on as my PA she was single and I was still married, albeit unhappily. I was 37 and she was 27. My wife, Maria, and I had married young, I was 25, she was 22. It was a silly thing to do but my family and all our friends kept on saying what a catch she was, that I was batting way above my average etc., and that I should get a ring on her finger before someone else did. In some ways Maria and I were a great match, intellectually we complemented each other perfectly. I am great at generating ideas but tend to be lazy and drop things at the first obstacle. Maria was incredibly disciplined and had a great work ethic. She was terrific at helping me work out which ideas were worth persevering with and had a tremendous appetite for work which inspired me to stick at things more rather than give up and try something else. As an economic unit we were second to none and we were each other's best friend. Sex was where things fell apart.

When it came to sex I know two things. The first is that sexual incompatibility is a major destroyer of relationships and the second is that sexually I was very adventurous. Before Maria and I started dating seriously I had been in a relationship with a much older woman who was rather sexually adventurous. Sally would let me do anything I wanted to her as long as didn't involve shit and I mean anything.

We fucked on our second date, then she sucked my cock until I came in her mouth. She swallowed that time but I could have blown my load anywhere I wanted. The next date she wanted me to fuck her ass so I did. It felt fantastic so I did it again - often. For the 18 months or so we were together she never let my morning hard on go to waste, she'd suck me, fuck me or at the very least give me a hand job.

We went to swingers' clubs and gang bang parties, I'd share her with guys she picked up at pubs and clubs and she'd share me with bi-girls that we picked up together. For her 35th birthday party we went to a swingers' club and she sucked my cock on all fours while 35 guys came up, fucked her from behind and pinned up the loaded condom on the wall like some online gang bang videos. She had only wanted 35 but somehow the club let 39 guys in. Sally didn't want anyone to miss out so four guys got to blow their load in her mouth that night.

Another time we were showering together and I started to piss. Quick as a flash, Sally got on her knees, wrapped her lips around my cock and drank every bit of it. Sounds weird but it felt almost as good as cumming in her mouth. She must have enjoyed it because at the next gang bang party we went to she told all the guys there to just piss in her mouth instead of going to the bathroom. Some were weirded out by the request but most of them were happy to and Sally happily guzzled down piss all night as well as sucking and fucking a dozen guys.

All in all, I was in a sexual paradise and even though Sally was 10 years older than me, after 18 months I suggested I move in as soon as I could find someone to take over the lease on my apartment. Bad move. She said she'd think about it but didn't call me or return any of my calls for a week. She finally called and invited me out to her place for the weekend but all weekend she seemed sad and distracted, although the sex was as awesome as ever. Over dinner on Sunday night she ended the relationship. She said the age gap was too big and she never intended for us to be like a proper couple, it was just about the sex. I tried to get her to change her mind, but she was adamant that it was over.

Maria and I had gone to different high schools but we'd run across each other regularly at debating competitions and we became friends despite me being three years older. Given that girls mature faster than boys at that age we were well matched. The friendship deepened when we ended up at the same university together and completely by chance she moved into the apartment next door to mine. I had worked for two years before going to university so I was only a year ahead of her despite the age gap and because I did an honours year we ended up hitting the real world at the same time.

I didn't realise it, but Maria had had a crush on me ever since the first time we met at a debating competition. Because I was older, when we first met I was an old hand who had represented my school at regional, state and national competitions for a couple of years, but it was her first regional competition. Maria had got lost on the large university campus that was hosting the regional competition and was starting to stress that she wouldn't be able to find where she was supposed to be in before the debate started and by the time she asked me for help she was almost in tears. Luckily for her, our respective lecture theatres were opposite each other so I walked her to where she was supposed to be and taught her a quick meditation and deep breathing exercise to calm her nerves on the way. Her team totally blew away their opponents on her first outing and she hung around till my heat was finished to thank me. I got a big hug and a kiss hello when we met at the state competition a few months later and from then on we hung out together at debating competitions and caught up occasionally out of school.

When Sally ended the relationship I was heartbroken, but Maria was too smart to be a rebound girl, she let a couple of others take the fall on that before making her move. We were walking home from work one evening when out of the blue she asked me why I'd never asked her out. I was surprised to say the least and stuttered something about not wanting to risk wrecking a good friendship by hitting on her.

The truth was, in all the years we'd known each other she'd never let on she thought about me that way. And I always thought my looks were pretty average, but Maria's Italian mother had passed on the looks of a slightly less voluptuous Monica Bellucci and I thought she was totally out of my league. When she turned to me and said, "Well if you ever did ask me out, the answer would be yes," I nearly tripped over my own feet.

"Umm. But. Umm. Maria. Umm. Would you. Umm. Like to go out for dinner tonight?" I barely managed to get out, I was so surprised.

"I'd love to, you doofus," she said. "There's a new Italian restaurant in Leichardt I want to try. I'll book it, you pick me up at 7, wear a jacket."

We held hands as we walked back to the car and when I dropped her home I got a smouldering kiss goodbye, matched by similarly passionate kiss hello when I picked her up that evening. I guess because we'd been friends for years before we started dating things moved quickly and we became a couple within weeks. Six months after the first date we moved in together and a year after that we were married. Maria knew about some of the stuff that Sally and I used to do and she laid down some ground rules early on. Swingers clubs and gang bangs were out of the question, as was anal, but she was happy to try other things. After trying it, Maria found she quite enjoyed being spit roasted and more than a few times a girlfriend of hers would stay at our place and the three of us would end up in bed together.

So far so good, but then we got married. Like most newlyweds, we were all over each other on our honeymoon and that kept going for a while. But all the adventurous stuff such as threesomes stopped fairly quickly. At first it didn't bother me that much. Having two girls at once occasionally was a lot of fun, but I loved Maria far more deeply than I ever had Sally. I didn't mind her blowing another guy but often felt uncomfortable if he wanted to fuck her. It was her call of course but I always felt relieved on those occasions when she refused and felt a little twinge of jealousy when she didn't. In the end there was no formal discussion about it, I just realised one day that it had been a year or more since we'd last brought a male or female playmate home with us.

Sex between the two of us was still good but within a few short years it just went from bad to worse. Our careers were both going ahead full throttle and Maria was also doing her PhD in her "spare time" but it got to the point where I only ever got a blowjob after I'd gone down on her and even then, not always. Instead of wakeup blowjobs and morning glories, I got pushed out of bed to make coffee. Instead of trying to distract me by flashing her tits or playing with my cock when she was bored watching Super 14 Rugby with me, she'd go into her study and work. Around about this time I got made redundant. I had been with the company for a while and got a healthy redundancy which put a lot of cash into the bank so at 34, I set up my own business.

Within a year I was making double what I made working for someone else, in two years almost five times, but I was working 14-hour days and at that point I realised needed to employ staff. Dione was my first hire. Her official title was personal assistant, but she quickly started helping with marketing and financials as well. With a business and accounting degree it seemed there was nothing she couldn't do and the business really took off. We hired more people and Dione became office and HR manager as well, but it wasn't long before we were big enough that we needed full time people in those roles too. I know I'm good at what I do but Dione was even better and hiring her was the best decision I'd ever made.

For the first few months we worked together it was very professional but also friendly. We got on like a house on fire right from that first meeting. Eventually Dione started to flirt a bit and I responded in kind but always kept within bounds. Not long after the flirting started I was invited to present at a conference. It was being held at a resort in the Whitsundays, things had been manic for the last few months and Dione had been working as hard as I had, so I asked her if she wanted to come to the conference. She wouldn't have a lot of work to do because I'd be conferencing, I'd just need her to keep on top of my email and handle any urgent issues that came up.

She came to the conference and had a great time for three days, hanging out on the beach and by the pool as well as exploring the island and hitting the day spa which I'd told her to charge to the corporate account. The conference wound up at lunch time on the third day but I'd decided to stay an extra night so I could go do some snorkelling and have a bit of downtime myself.

For much of the conference Dione had worn little more than a tiny G-string bikini during the day; I swear my handkerchief had more fabric in it. If other conference delegates were around she'd throw on a sarong but if it was just me she stayed in her bikini, giving me a great view of her incredible body. Dione was almost as tall as me, about 5'10", with long dark red-brown hair and unusual for a redhead, slightly olive skin. Very athletic with barely any fat, her boobs were a good size, a well filled B, small C probably, and very firm with hardly any bounce as she moved.

Much to my surprise when I said I was going snorkelling, she came with me and seemed to have a great time. It was the first time she had ever done it and she was excited as a kid at seeing the reef closeup. As we walked around the island she couldn't stop talking about it and how it was just like being in a David Attenborough documentary. She was wearing one of her tiny little bikinis again - she seemed to have a new one for each day - and I had plenty of time to enjoy the sight of her incredible body.

After the circuit of the island we hiked up to the highest point of the island where there was a look out. The view was incredible, blue sky and the sea myriad shades of blue as we looked out over the Great Barrier Reef and we just sat there together, quiet, comfortable in each other's company looking at the view.

Later that evening we had dinner together at the resort's upmarket restaurant. The conference had been a great success. My presentation had gone down very well and we'd picked up some more work from existing customers and got a lot of interest from some prospective clients. I was in the mood to celebrate and the restaurant had an impressive wine list so I kicked the night off with a bottle of vintage Bollinger champagne.

Dione looked incredible in a backless halter necked black dress and more than a few husbands and boyfriends got a dig in the ribs for ogling her a little too obviously or frequently. We started off talking about work but before long we were talking about all sorts of things; family, interests, what we did in our spare time, what we thought about various issues of the day. We laughed, we debated some issues spiritedly but respectfully and were in furious agreement about others. I always knew Dione was smart but as the night wore on my admiration for this beautiful and intelligent woman increased the longer we talked.

She surprised me when she asked, "Are you happy?"

"That's a hell of a question," I replied. "Does it look like I'm not?"

"It is and yes, sometimes," Dione said. "I get the impression that you love your wife totally and utterly but you're not happy with the way the relationship is going."

I hadn't talked about my growing dissatisfaction with my marriage to anyone but before I knew it I started to talk to Dione. I could hear the voice of my relationship counsellor mother in my head. "The last person you should be talking to about your marital problems was an attractive woman who could possibly be interested in replacing your wife," so at first I was guarded, admitting I was unhappy but not going into any great detail. As the night progressed I found myself opening up and telling Dione more and more. The wine that we drank with dinner had a lot to do with it but I also needed to talk to someone because as I talked, I realised that I was desperately unhappy.

"I shouldn't be telling you this as we work together and everything," I said, "but you're the first person I've felt that I could talk to."

"Have you tried talking to some of your male friends," Dione asked.

"It is difficult because I don't have many close male friends, Maria has been my best friend since high school, but yes, I have," I replied. "They all have kids and their sex lives are even worse so they think I'm complaining about nothing. Most of them reckon that even boring sex once a week with a woman as stunning as Maria is better than what they've got."

"But how do you feel about that?" Dione asked.

I went silent for a while, trying to find the words to express how I felt.

"Do you remember the old joke about the bride who says she's incredibly happy because once the wedding is over she'll never have to give her husband to be a blowjob ever again?"

Dione nodded. "Yes. It's one of those stereotypical metaphors that are uncomfortably insightful."

"Yeah, that's how I think about it as well. And you see, I swore that I didn't want to marry a woman like that, that I didn't want my life to be like that. I swore that I didn't want to be begging for a blowjob on my birthday a few years after I got married."

"But that's what you ended up with," Dione said.

"Yes, that's what I ended up with. Maybe those self-development snake oil salespeople like Tony Robbins are right and the universe doesn't recognise the word don't. Maybe I brought this all upon myself even though I was desperately trying to avoid it."

Dione leaned back in her chair and looked at me. "I think you're being too hard on yourself but the question is what are you going to do about it?"

"I don't know," I said. "In every other way we are incredibly compatible, and it seems just crazy to blow up a marriage over lousy sex. Not to mention that my family and hers are both Catholic and would go nuts if I just walked out. Maria and I have achieved so much together, I would never have taken the step of starting my own business without her support and we wouldn't have had the financial reserves if she'd been like most her friends who spend money faster than they earn it. Maria's always be incredibly disciplined with money and she taught me to be like that too. Which meant we already had a year's living expenses in the bank when I got made redundant. But then she wouldn't have done her PhD and become an academic without my support, so it's been a two-way street."

Dione asked me again. "So again, what are you going to do about it?"

"For now, I'm going to do nothing. I suggested counselling a little while ago. Maybe I need to suggest it again."

"If leaving the marriage is not an option that's probably the best you can do," Dione said. "But for what it's worth, I think you deserve better than what you've got now."