The Jennifer Jones File

I wasn't looking for trouble. I was just sitting with my feet propped up on my desk in my office on the fifth floor of the Bradbury Building, watching the traffic on Broadway, when trouble walked through the door and locked it from the inside.

"Hello, Jake," she said.

I knew this was not going to end well. It never did with Jennifer Jones. I'd helped her through two divorces and one pre-nup. That is, I'd investigated men in her orbit. Then she'd taken them down, badly. As a result, she stopped by to see me from time to time when she was downtown and needed something. What she really needed was always the question.

Jen flopped down in the armchair in front of my desk and draped one long leg across an arm of the chair. She wasn't wearing anything under her black miniskirt, which rode up her firm hips. A luscious bloom of swollen pussylips blossomed like a flower opening from her closely trimmed blonde bush. It was hard to ignore.

I wondered if she had walked down Broadway like that. Or just taken her panties off in the bathroom down the hall from my office before coming through my door. I imagined her walking from the parking garage down the block, along the crowded sidewalk in the summer heat, getting wetter as she went along. And enjoying every minute of it.

I looked up from her crotch. "Jen. Yes. What can I do you for today?"

She smiled crookedly, stood, and slowly crossed the distance between us, while unbuttoning her sheer black blouse, which already did little to hide her full tits. They had dropped just a little lower as the years had gone by, since I had met her in her early thirties, but still held their shape quite nicely, two ample classic amphoras of smooth clear skin ending in dark pink nipples that stood up hard as she came closer.

She leaned over me so that her jugs hung temptingly in front of my face. She reached down and grabbed my crotch.

"At least somebody's happy to see me," she said, as she squeezed my cock, which was, as usual, responding with a mind of its own.

She lifted one leg to straddle my extended legs. Her miniskirt rose further tightly clumping high on her hips. Clearly moist pussylips dangled seductively between her thighs.

I was mesmerized. My mouth was watering.

I knew it was dangerous when things started like this. Jen was always a risky proposition. And especially so when she was horny and wouldn't take no for an answer.

Of course, I couldn't say no anyway.

It wasn't every day that a beautiful mature woman - or any woman for that matter - walked through my door wanting to fuck me. I wasn't getting any younger either. And I sure wasn't aging as well as Jennifer Jones.

But I could still get reliably hard pretty quickly without even trying, even if wasn't in my best long-term interests.

And now Jen had unzipped my slacks and had my boner in hand. She rubbed the tip slowly along her wet pussylips. She groaned softly and licked her lips. I involuntarily moaned softly.

She lowered herself a little, taking just the tip inside her. She squeezed the head of my cock with the opening of her pussy and then pushed down, taking more of me inside.

Everything else about Jen was as loose as could be, but her pussy was remarkably tight for a woman her age. And my cock didn't go in easily. She took a deep breath and then pushed all the way down.

She stopped then, leaned back, and looked at me. I was looking at her pussy, with my cock buried in it. It was a beautiful sight, I had to admit. She spread her labia with her fingers. I could see the pink tip of her clitoris poking out at the top of her cunt. She brought her hand to her mouth to wet her fingers and then brought them back down to rub her clitoris as she rocked back and forth slowly on my cock deep inside her.

"Come on, Jake, help me out here," she said, as she took my hand and pulled it to her mouth to get my thumb slick with saliva and then moved it down to her clit. I gently circled it with the pad of my thumb.

"That's it," she said. She moaned and ground down harder on my pelvis.

It was generally a good idea to do whatever Jennifer Jones wanted, if at all possible. She had first come to me more than two decades ago to investigate her husband, a professional tennis star, who, it turned out, had a semi-steady girlfriend at every glad slam tournament in the world, and casual hookups at every other stop as well. Two of the steadies were pregnant, and he was engaged to one of them, while married to Jennifer Jones. After I laid out the evidence for Jen, she took a racket to the trophy shelves in his home office and nearly split his head open. That put a bit of a wrinkle in her case for child custody - his attorney was not wrong to argue that she was a little unstable and had anger management issues - but I found her a lawyer, one of the toughest in town, and she came away with the kids and a tidy endowment from his tournament prizes and endorsement earnings.

And I couldn't complain with two of the nicest of her endowments swaying in front of my face. With my free hand I squeezed one hard and sucked and nibbled on the nipple, while thrumming her clit. I took as much as possible of first one tit and then the other into my mouth, going back and forth between them. She leaned in and rode my boner harder, then slowed down and leaned back to savor the moment. I fondled both of her breasts.

She had one of those platonic ideals of the female form, when she was happy, that is. A blissed-out look on her face, tousled hair, large, shapely, natural tits, firm thighs and calves, and a fit, soft waist, that I held in my hands as she rode up and down faster again, her tits flopping rhythmically.

She was ready to come fast, I could tell. But she always needed and wanted a little help. So I found her clitoris, again. It was a swollen hard nub now. I rubbed fast and light across the tip and then let her push again my thumb harder as she leaned over me and rode me hard. I caught one of her flopping tits and sucked on it hard. I bit down on her nipple as she moaned loudly as she ground her clit against my thumb and her body shook and shook.

It took her a minute to come back from that. She was breathing hard. And I was still hard inside her. She squeezed my cock with her cunt muscles and milked me deliberately then from top to bottom. Now she got into fucking me. She lifted up and went back and forth quickly just focusing on the head of my cock. Then she pushed all the way down again slowly and back up.

It was almost like a blowjob with her cunt. My cock slipped out and rubbed against her short pubic hairs and I almost came right then from the friction. "I know you don't like that," she said, as she grabbed my cock firmly and rubbed it against the outside of her cunt. "But I do," she said, as she put it back inside her, swallowing me up again.

I thrust into her then harder, holding her waist, fucking her hard, as she rode me, pounding down on my pelvis. When she came first, I almost came, too. But I was so focused on her, I didn't. She had to come first. And then I wasn't sure I would after all. I didn't matter all that much.

But I was going to come now for sure. I could feel it coming on, from that deep point below my balls, building and coming to a boil.

One thing about Jen, I didn't always come when we fucked, but when we both came it was some of the best pure fucking of my life. A man could lose himself in this. And I did. I could feel myself getting harder, the head of my cock swelling.

Jen could, too, and I could tell she liked it. She loved being in control. She loved making a man come.

Just as I was about to blast off into her, ramming it home for all I was worth, totally lost in the fucking moment, she lifted off me.

She knelt between my legs and took my cock in her mouth. And then I came with what felt, it often felt with her, like more force than ever. It had been a long time. And she took it all, moaning and slurping and swallowing, and then sucking my cock dry until it was all totally empty. My balls ached they were so empty. Then she licked my cock clean, slowly, from bottom to top.

"Sorry, Jake," she said. "I didn't want all that running down my legs when I walked back to my car, you understand."

Then, from somewhere - where I don't know - she produced a handkerchief, dried my cock and balls gently and carefully put them back in my slacks and zipped them up.

She pulled her miniskirt back over her thighs, barely covering her pussy again, buttoned up her blouse, licked her lips, and looked at me, waiting.

"So, what can I do you for this time, Jen?"

"It's not for me, Jake," she said, with a rueful, crooked smile that slowly turned to an angry, determined scowl.

There was the trouble I knew was coming the minute she walked through the door.

"It's my daughter," she said, "and that ne'er-do-well, wannabe baller husband of hers."