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Indecent Proposal


When I won millions of dollars in the Massachusetts lottery back in 1990, I thought of some sexually creative things that I could do with the money, one of which was to persuade some of the women who I have lusted over for years to have sex with me, for money, of course.

Ah...you'd be surprised what women will do for money. Yes, sir!

"Wait, am I hearing this right? You let him fuck you and, then, gave him a blow job for...how much?"

Yet, I digress. The story started a few years after receiving my annual lottery payout checks from the Commonwealth of Massachusetts. Suddenly, I found that I had bought everything that I had ever wanted, and after giving away more money to friends and relatives then I could have earned in a lifetime; I was bored. Whoever said that money cannot buy you happiness must have won millions of dollars in the lottery.

That was when it struck me. Let's have some fun with the money, money that you would give away, anyway. No one should have as much money as I won. So, I gave much of it away, but how I gave it away is the plot of this story.

All Italian, Anna had that European sensual, sexy look like she just got out of bed after being fucked long and hard. With dark brown hair and mahogany eyes that held your stare making it impossible to look away, she was stunning. At 5'6" and 130 pounds, whatever extra weight she had was in her ass and her tits. Man, she had a body that danced the Samba when she walked making you recall the song, "The Girl From Ipanema."

"Tall and dark, and young and lovely, the girl from Ipanema goes walking and when she passes each one she passes goes...ah, you get my point."

Every time we attended a social function, with my wife and her husband, I got a huge erection whenever I danced with Anna. Further, I knew she knew that I had an erection because I planted it deep in her stomach, thigh, and ass. Oh, baby, she was hot.

She was a fun person with a contagious laugh. She was someone who you wanted to befriend, spend time with, and invite to a party. I guess, now, that I think about it, I was a little bit in love with Anna.

Anna was the wife of my best friend, Billy, and the first one who I approached. Actually, now that I think of it, she broached the subject of money to me.

"Lucky, dog, winning all of that money, what are you doing with it?"

"I don't know, Anna, it is overwhelming. I mean, after buying new cars, paying off the charge cards, buying a bigger house, doing some traveling, what is there left to do...more shopping?"

"Freddie, you say it like there is something bad about buying things and not having to look at the price. Just once, I would love to buy something from an expensive boutique on Newbury Street instead of cutting coupons out at Wal-Mart."

"Well, I still look at the price and I still look for a bargain. That will never change about me. Maybe, had I been born to wealth but when you suddenly find yourself rich, you cannot change who you are. Yet, what it did for me was, it bought me my freedom. Never, do I have to work for someone else, again. Now, I work for myself. I let my money work for me by investing in the stock market and buying real estate."

It sounded so much more glamorous than it was, but I was still bored.

"If I had that kind of money..."

"Go on, what would you do?"

She looked at me with those big, brown eyes and flashing me her sexy grin. Damn, she was gorgeous.

"I'd pay all of my charge cards."

"How much do you think that is?"

"Oh, I don't know," she paused and looked up as if seeing a large calculator in the sky, "twenty-vie thousand, maybe."

"What if I gave you the money to pay off all your charge cards?"

"You'd give me twenty-five thousand dollars?"


"Yeah, right. And what would you expect in return, my undying loyalty?"

I gave her a look.

"My heartfelt gratitude?"

I gave her another look.

"My first born child. Well, you can have him because he is just like his father, a pain in my ass." She laughed and I gave her, yet, another look.

"I was thinking more in the line of a sexual favor."

"Sex? You mean sex? With me? You want to fuck me? Freddie, c'mon, are you kidding? I'm the wife of your best friend, Billy." She paused with a look that came over her face like she was contemplating it. "What if he found out?" She paused, again. "No, I can't do that. I can't do that to him."

"Shh, lower your voice, the neighbors will think that I am propositioning you."

"Well, you are. Only it is more like asking me to prostitute myself." She laughed. "It's like that movie with Demi Moore and Robert Redford, uhm, what was the title?"

"Indecent Proposal, except there is nothing indecent about this and about how I feel about you. I am and have always been very much attracted to you, Anna, and if we do this I would respect—"

"What? No. You are making me feel cheap, used, and bought and paid for." She gave me a look that made me feel that I had crossed the line with her. "You are serious." She paused, again. "What if Arlene found out. Don't you care that you are cheating on her?"

"She won't find out and Billy won't find out. Think of it as one friend helping another. I have money to help you and you have, well, your body to help me."

I don't know, Freddie, if Billy found out, he'd plant you and your money six feet under.' Billy, Anna's husband, was as big as he was Polish.

"He does not have to know, Anna. I'd pay for a room at a nice hotel out of the area and away from Boston."

I could tell by the look on her face that she was intrigued and was considering it. We nearly did it one hot summer in the pool after we each had half dozen vodka tonics. I had her top off and was sucking her tits while her hand was down my bathing suit trunks and wrapped around my stiff cock. No one could see us as were in the dark and everyone else was on the other side of the yard in the screen house and just as drunk as we were.

"Let me get this straight. If I give you sex, one time, you will give me $25,000?"

"No," my mind raced trying to reconsider the scenario now that it was a possibility. "If you have sex with me," the thoughts of having Anna naked for a day filled my mind with her image, "five times, I will pay you $25,000."

"Five times? I don't know, Freddie, that's a lot with more chances of being caught." I could see in her eyes that she would never go for it.

"Three," I involuntarily blurted out not wanting to ruin my chance with her, "just three times, then."

"Twice, Freddie. I'll do it twice. I can't do three times. Three times is more like a love affair. Twice is only sex. I can do it twice." She implored me with a look. "Okay?"


She stuck out her hand and I pushed it away, pulled her close, and kissed her.

"Freddie," she pulled away, "the neighbors," and laughed.

"So, we have a deal?"

"Yes, but you have to buy me dinner, too?" She laughed.

"Of course, I will feed you before we do it."

With that she pressed her lips against mine, gave me a peck, and walked away with a wave of her hand. "Ciao! Call me."

The suddenness of her affirmation caught me off guard and overwhelmed me in my desire for her. I called her that night and made the arrangements for that weekend.

We drove to the Four Seasons in separate cars. I offered to drive her out of Boston, but she said that she had always wanted to stay at the Four Seasons.

She wore this yellow wrap around dress that flattered her figure and hugged her curves making her tits look bigger. She had a full B cup but in that dress they looked like a C.

I was more nervous than she was. It felt awkward to privately meet your best friend's wife with the intention of bedding her. We had a great dinner and finished a bottle of Pinot Noir before heading up to the room for the night. I had seen the room beforehand and made sure that I had one with a view of the Public Gardens and the Charles River and had room service put a bottle of champagne on ice.

We started making out as soon as we entered the room and fell on the bed together. My kisses were more passionate than were hers and I could not wait to unwrap her body from that dress. She popped up.

"Will you look at this room? Wow, it has a bar and...another room."

"It's a suite."

"Freddie, did you see the view? I can see the Boston Commons, Public Gardens, the Esplanade, and the Charles River. Look, there's the airport and Arthur Fieldler's Hatch Shell. This is great. It is so romantic. I'll have to take Billy here for our anniversary."

I gave her a look.

"Sorry, I shouldn't be talking about Billy." She walked up to me and kissed me. "It was expensive, huh, the room."

"Yeah, but you are worth it."

We started making out again, only this time, I got her out of that dress, which was easy since it only had the one sash that tied in front.

She wore this amazing matching yellow, silk bra and panty set. She looked hot in her underwear. There is nothing like feeling a woman's soft, supple skin, her back, her stomach, and her thighs. That, in combination with the feel of silk underwear, is as intoxicating as was the wine at dinner and the champagne we sipped, now.

It excited me to feel her full tits through her bra and to feel her warm wetness through her panty. It did not take us long to get naked. I did not fuck her, I made love to her. She was different. She was someone that I could have fallen in love with and married, had I had the chance, had the opportunity presented itself, and had this been a different place and time. We were so compatible and made one another laugh. We were always on the same level with so many things, never having to explain our words and never uncomfortable with one another. There were never any silent moments. She could say something and I could finish her thought and vice versa.

We were in bed making out, giving one another pleasure orally and making love when we both started laughing. We laughed so hard that we could not stop laughing. When we did finally stop laughing, we did everything all over again. She was just as attracted to me as I was to her. We fell asleep finally holding one another and it was after midnight when she awoke with a start.

"I have to go home. I told Billy that I was going out with the girls and told him that I'd be home by eleven. Freddie, I never knew it was going to be like this. This was beautiful I could fall in love with you, which is why I cannot do this with you, again. I'm sorry. And I cannot take your money, I'd feel guilty, cheap, and like a prostitute."

"Oh, the money, here, please, take the money. I want to do this for you. Actually, I would have given you the money without you having to give me sex but—"

"Oh, so I don't have to make love to you again?" She punched me in the shoulder and snatched the check from my hand.

"Well, I'd really love to see you, again, Anna, but I understand." We made eye contact, hugged, kissed, and parted.

"I had the best time, Freddie."

She kissed me again and was out the door with a wave and a smile.


"Ciao, Anna."

I could not sleep or eat. All I could think about was making love to Anna. It was nearly two weeks before I saw her again. I bumped into her and Billy at the mall. She was holding his arm and held it tighter when she saw me. Suddenly, she appeared uncomfortable and I wondered if she had told him. I wondered if he knew. I suspected she told him and that he was okay with it, so long as it did not happen again. Yet, it destroyed our friendship and I never saw either of them socially, again.

I did not think about making love to anyone else until I thought about doing Tiffany, Phil's wife, my oldest and closest friend, who I had not seen in two years. Yet, that is another story for another time.


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