The Devil and Jill Flaherty

by Lucky Malone

Caution: This Flash Sex Story contains strong sexual content, including Consensual, Reluctant, .

Desc: Flash Sex Story: It's axiomatic. People will try to do the right thing if life dumps a steaming pile of moral ambiguity on them. But, the right thing isn't always obvious, especially in abnormal circumstances. So, it's important to think through all the implications before you decide. Because, hasty actions can spawn another term, "It seemed like a good idea at the time." I offer this example of dubious ethics and bad judgement to prove that point.

My wife’s family has a long and storied history as low-life trailer trash. Her father, who has never worked a day in his life, has the IQ of a lemur. Still, he DOES drink; which occasionally leads him to touch up Jill’s mom. Jill’s mom dropped out two kids; neither of whom were fathered by her alleged husband. Still, she DID hold down a steady job. She worked at a strip club. She said she liked the ambiance. She must have been a good-looking woman; before the booze and drugs caught up with her. But now, she puts new meaning to the term, “Ridden hard and put up wet.”

Jill was six years old when sister Willy came along. Willy’s real name is Wilhelmina. It’s a tribute to a Dutch guy, who was passing through nine months before her birth. Jill’s mom was always god-knows-elsewhere. So, even though Jill was just a tyke herself, she took care of little Willy from the day she was born.

As they grew up, Jill nurtured and cared for her little sister. Thus, there were more than just sisterly ties. Willy was like Jill’s kid. Jill protected her from her pseudo-dad’s drunken rants. And during the days that their parents were MIA, Jill scraped together enough money to feed them. Hence, Jill’s sense of self-sacrifice was ingrained from birth. That is an important thing to keep in mind as you read this. The other critical thing is the difference in appearance between the two sisters.

Jill’s hit-and-run-candidate must have been a Swede. She has the enigmatic blue eyes, thick blond hair, long narrow Swedish nose and sensual mouth of a classic Nordic beauty. Nonetheless, it’s her outrageous body that gets all the attention. Jill’s mom has huge jugs. Jill’s are a little smaller, but not by much. The rest of Jill is supple, trim and athletic, with long beautiful legs.

Poor Willy lost the genetic lottery. She has wide shoulders. No waist, peasant hips and her legs would be more appropriate on a chicken. She also has a broad Dutch face with slightly gapped teeth. In short, she looks like the Tasmanian Devil; if the Tasmanian Devil had humongous tits.

I first encountered Willy when she was eighteen. I was a regular at a certain restaurant. I wasn’t eating there for the food. I was eating there because of the stunning blond waitress; who always seemed to be assigned to my table. It didn’t take many visits to ask her out. We had a few coffee dates, that progressed to a real date.

I remember the first time I saw their squalid little flat. The two women were living in a one-bedroom apartment that would give a coal miner claustrophobia. Willy answered the door. I had heard about her. But, it was the first time I’d met her. My initial thought was, “This one’s going to have a hard time finding a husband.”

Then, Jill appeared and all thoughts of Willy’s predicament vanished. I had only seen Jill in some variant of her waitress uniform. Now she was standing there in a cheap little-black-dress, with her sheaf of shining blond hair hanging down to her shoulder blades.

The dress hugged every nuance of her lithe body. It was probably her only GOOD dress. But it showed off her assets from her big fabulous tits, all the way down to her beautiful long legs. I just stood there with my mouth hanging open, while Willy gazed at her sister with unadulterated hero worship.

Jill did a little twirl and said, “You like?”

I said truly flabbergasted, “You’re beautiful!!”

She gave me a flirtatious smile and said, “I bet you say that to all the women you date.”

I said, “I have never dated a woman as beautiful as you.”

She got that simpering look that women get when their emotions are riled up. She said, “Flattery, might get you laid.” And it did.

It took more than one date. But, Jill eventually agreed to a weekend in a quaint bed and breakfast up in Marine City. Willy was nineteen and perfectly able to care for herself. So, Jill’s absence wasn’t the issue. I just hoped that Jill could forget the daily care-and-feeding of her sister, which was always foremost in her mind.

Jill has a quiet and thoughtful personality. She can be deliciously witty and she has a wide-ranging world-view. But generally, she is reserved and never lets her guard down. The guardedness branded her as one of those “responsible” types. I suppose any six-year-old, who was a baby’s primary care-giver, would have a few monkeys fucking in their attic. But Jill’s urge to fix things for Willy, especially when those things were either impossible to fix, or none of her business, was absolutely nuts.

We had a nice dinner in a romantic restaurant, overlooking the river. Then we settled down in our quaint Victorian room. It had one of those big antique four-posters that semi-reminded me of bondage porn. But it was modern and comfortable. Jill came out of the en-suite in a Calvin Johnson jersey. There was plainly nothing underneath it.

She walked over to the bed and the first thing she did was check her phone for texts. I knew she was thinking about Willy. It was a bit of a mood killer. Then she shucked off the jersey and plopped down on her back next to me. All thoughts about Jill’s state-of-mind vanished. It was, “Game on.”

She is only five six. But she has one of those lean, long waisted bodies that would be considered skinny if it weren’t for the fact that there were a couple of massive tits sitting on her rip cage. Her waist is tiny and her hips are wide and fruitful. She has long legs. I noted how powerful, and toned they were. Her thighs are full, a little longer than average. So, the impression you got was that she is all-leg.

Nonetheless her boobs are the exceptional part. When they lay on their back; most women with breasts as big as Jill’s have them slide off onto their arms. Jill’s massive jugs just puddled out on top of her chest like two monster hills.

Normally, the only way you could get an effect like that was if they were made out of silicone. But, I knew they weren’t. Jill couldn’t afford health-care, let alone a boob job. Her nipples were perhaps the best part of the whole package. The aureoles were dark brown and extra wide, and her bright red nubs stood out almost a quarter of an inch.

I turned toward her. She had her eyes closed and she was panting. I leaned over to the nearest boob and took the red-hot nipple between my lips. Jill groaned with sensation. Then I bit down gently and she shrieked.

All the time I was doing that she was muttering to herself, “So long.” I don’t think she was talking about what she was idly jacking. It can hold its own with the rest of the boys. But she seemed to be talking about the time between when she had last had sex.

I worked my hand down her flat stomach to her slit. It was boiling hot and heavily lubricated. She must have been thinking about this for some time, because she was most-definitely ready. I slid my fingers across her prominent clitty. That produced a prolonged groan and her legs spread wide to give me access to everything down there.

Jill might be guarded and controlled in every aspect of her life. But, she’s a different person in the sack. This version is a passionate and needy woman. I suppose that a life of responsibility and self-sacrifice can bottle up a lot of feelings. Those suppressed emotions let go in an explosion that made Mount St. Helens seem like a party-popper.

I touched her clit. That started the first of what seemed like endless orgasms. she just went off like a skyrocket. Her legs spread reflexively and elevated, banging me in the side of the head. Then, she began to hump the air. I went on twiddling, while evaluating myself to see if I had a concussion. She started pulling on my shoulders. It was like she was literally wrestling me into position.

She said through gritted teeth, “Fuck me!! You have to fuck me!! I have to have it. Right now!!!” I was kneeling between her legs, trying to hit a widely gyrating target, without much success. She grabbed me impatiently, and forced me into a fiery furnace of need.

As I slid up into her she yelled, “OH MY GOD!!!” wrapped her legs around me and began frantically bucking. I looked in her face and her eyes were rolled up in her head, only the whites showed. She started thrashing around, emitting a keening wail, utterly lost to her passion.

I fucked her for a while and Jill just got noisier and noisier. I was glad we were in the attic room. Finally, she was on her hands and knees and I was concentrating on the middle of her muscular back, just above her two big round buns. I was marveling at how hard her body was, almost without fat and trying as hard as I could to get to the finish line, before the management kicked us out for being so noisy.

As the mother of all orgasms hit her, Jill began to yowl like a cat in heat. I later discovered that was Jill’s distinguishing trait when she came hard. Then she collapsed face forward spasming and twitching like she was having an epileptic seizure.

I came at that point. It was so overwhelming that I thought I was going to explode. When I finally got some rationality back I found myself sprawled on Jill’s back. She was face down arms stretched straight over her head still wringing out the sheets. Her butt was hoisted with me shrinking out of her. Our mutual sweat was sticking us together. She was still undergoing little aftershocks. They felt delicious. We were both taking great gulps of air.

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Story tagged with:
Consensual / Reluctant /