Jill, My Whore

Jill had been married three years when we first met. She never called me anywhere but at my office and always at 4:30pm on Thursdays. Not every Thursday, but randomly and her tone was always furtive and hesitant, as if she did but she didn't want to meet and carry on our sticky, steamy affair. I knew she liked it. She liked the danger, the adventure. She also liked the spontaneity and the imaginative ways we came up with together for outrageous sex in outrageous places. These were things she could not count on her husband giving her. He was far too urbane for such outlandish things like sex in the middle of the week. For poor old Rick it was sex every other Saturday night, before ten and after viewing a porno video in the secrecy and privacy of their closed, locked and darkened bedroom. When I first met Jill she told she was bored with him and his predictability.

On this meeting, Jill had asked me to do something very different. She had called me the previous afternoon, at work, at 4:30 and said to meet her in the 1000 block of Harris Blvd. that sane evening. Now, Harris cuts exactly in half what is called a neighborhood "in transition". Which means it's property value has dropped to nil since all the Ma and Pa shops closed their doors forever and all the revenue went to the malls east of downtown. It was low-rent and seedy. Streetwalkers populated the lower end of Harris day and night. Some dead, some still dying right along with this part of downtown. It was dope and booze and disease and despair on south Harris Blvd.

"Harris..!? Where on Harris are you gonna be, Jill..!? In a restaurant..? A bar... what?" "Five fifteen... be there..." was all she said and then she hung up. I was genuinely confused and a little concerned. I had known her to do things on impulse before but for her to go into that part of town ever was so far out of character that a real shiver traced up my spine when I heard the phone line go dead. I looked then at my watch as I hung up the phone. I had a little over forty-four minutes to think about what she had said.

Driving down Harris, I saw what I knew I would see. First, a very brazen black woman of about 36 stared me down then called to me from the sidewalk when I got next to her, "Hey baby...!" she said. She looked very poor, very desperate and not too healthy. I moved past and came upon a very skinny white girl who stood against the wall of a now closed Rexall Drug store. She was working her jaw and her eyes were glazed... vacant. She said nothing but motioned with her head three times as if to say "Come here..!" Next was a very large black woman about 45 years of age. She was downright frightening. I could see a very wide scar along the right side of her face from her chin running into her hairline.

Some fifteen years prior, I had cruised this stretch of Harris one night after spending too much time and money in one of the strip clubs further back toward town. I knew there were women here who would do anything for the right price and on that night, I picked one up. I could still remember her. She was a very petite black girl with a very wide and pretty smile. She was only 19 then or so she said. Indeed, she looked that young. We drove to her apartment and she had given me one of the finest blowjobs I'd ever had. Those were the days before rampant crack abuse and AIDS. I wondered now if that first black woman was the same girl...

Then I saw Jill....

At least she kind of looked like Jill. The same height and shape. Same fiery red locks on her head... but that couldn't have been Jill. That girl was wearing a very tight and very short black mini dress with what looked like stiletto heels. On top, a very cropped bright red sweater that fit tight also. Not Jill's style. She had waved and winked at me... it looked like Jill. I turned and headed back around the block for a second look.

When I approached her again, she motioned to follow and darted into an alley between two very run-down buildings. I turned in and there she was, walking away from me, but turning and stepping into my path thru the alley. This was definately my Jill. I stopped and rolled my window down as she strolled to the truck's driver side door.

"Saw ya drive past!" she said, smiling that smile, her eyes heavily lidded and sultry looking from beneath the long wild red bangs. "I wasn't sure if you were lookin' or not!"

"Jill... what the hell-" I said, but she cut me off...

"You lookin' for a date tonight, hon..?" she said. She was smiling and chewing gum and talking all at the same time. Looking very sexy... make-up and her hair done in a very vampish style.

I was confused and amused but decided this was her game, I'd try and play along. "I saw you and decided that I could use a date with such a gorgeous lady as yourself... hop in." She skipped around to the passenger side and as she climbed into my truck, I caught a quick glimpse under her short mini. Little red undies with a lacey edging at the leg openings. She knew I saw and I knew she did not mind.

Once in the truck she said, "Are you the police..?"

"No... I ain't the police, doll. What can I do to prove it to you?" I said.

"Show me what's makin' that big lump in yer jeans..." she said, that wicked smile returning then. I reached down and unbottoned my jean shorts, unzipped and pulled them, along with my underwear, forward, giving her a good look at my already pulsing hardon.

"Mmm... wow... " she said, "Okay... yer not a cop." She turned her head and began lighting a cigarette.

"What you got to show me..?" I said, covering myself. She looked at me with a big grin across her full, red lips... gazing thru those bangs again and making me hotter with those eyes, those eyes! She opened her legs wide then, causing her skirt to ride clear up her thighs. I could see the red panties clearly now... very tight and shiny, her mound giving just the right amount of feminine bulge in the crotch. My cock twitched seeing just that. She reached down and slid two fingers under the elastic band on the left leg opening and pulled the crotch to her right, exposing a very tidy and very pink pair of cunt lips. She never took her eyes off mine as she did this, still smiling that wicked smile and watching me with those huge, half-closed green eyes. "Mmmohhhh... jesus baby..." I said, a bit of a stammer in my voice. Her pussy had never looked better...

"What you want tonight baby?" she asked.

"Blowjob..?" I answered, my voice a little uneven.

"Okay..." she said, "it's 40 and I gotta have some money first, hon." she said. Jill had never acted like this before. Very confident and self assured... take-no-shit kind of woman. She indeed wore it well. I produced a fifty dollar bill from my wallet and handed it to her.

"Give me a little handjob with those panties first and you can keep the tip..." I said.

She smiled and raised her hips off the seat, lifted her skirt and began to slowly slide the tiny red panties down over her hips. Her muff was as usual trimmed very neatly and showed red as her hair above. In a second she had the panties off then said, "We can't sit here, baby... Go to the next block and trun right I know a real private spot to park."

We arrived in another alley about half a mile away. Halfway down, there was the rear of what looked like an abandoned warehouse building with a loading dock on one side. We drove around and I backed into the dock area where we were completely out of sight. Even if a car had driven right past us in the alley, the driver would not have known we were there. I unfastened my shorts and pulled my hardon out fully. I was very, very hard by then. Jill had sat there fondling her panties... stretching them out, laying them on my bare thigh, brushing them across my cheek and such... teasing me while we drove. Now she positioned them in her hand so the crotch lay across her palm.

"Ready baby..?" she asked, grinning and moving her eyes from my cock to my eyes then back again.

"God yes... mmmmmmm... do it, honey..." I said.

She reached over and gently wrapped her warm, soft hand around my raging cock, being careful to place the panties directly against the underside. Gentler still, she began a slow, easy stroking motion... up and down, up and down her fist moved, not too tight, not too loose... just enough to give me the full satiny effect of her panties within her hand. I closed my eyes and felt a wonderful jolt deep in my gut. My balls at once began to tighten and pull up toward my body. What a glorious feeling! Jill leaned very close to my lap and I could feel her breath on my pubic hairs as she watched very closely her progress. Soon she leaned further over and I could feel her full, warm lips at the tip of my cock. Little by little she eased the head of my cock between her lips as her hand continued it's up, down motion. At this point I reached forward to the rear view mirror mounted on the windshield and tilted it down to show me her pretty face buried in my crotch.

I could see the head of my cock slip into, then easily back out of her wet mouth. A little more... two inches... three... back out. Five inches disappeared into her mouth, then wetly slid back out. Now she engulfed the entire length deep to the back of her throat. Holding me there for a moment, I felt, as well as heard her gag slightly. Jill had never taken this much of my cock so deeply into her mouth before. I held very still as she acclimated herself to it, then very slowly slid me back out with her lips pulled tight around the shaft. Unbelievably good head! My head swam for a second as she began a very slow, steady bobbing motion with her head. Her right hand was now cupping my balls, nestling them in the tiny red panties.

I reached over with my right hand and began to feel her body. Her ass was easily accessible. Her breasts were a bit more difficult to reach. I wanted more...

"Open your legs, baby..." I said in a whisper. She was sort of lying on her left side, leaning to me. She at once twisted her hips so her butt was on the seat and her right foot was on the door armrest. I could now reach down and hold her sex in my right palm with no trouble. I began to gently rub her mound and her cunt, warming her. Jill continued her bobbing motion, up and down her lovely mouth slid, bringing me fully erect now. I knew it would not be too long before I filled her mouth with my cum.

"Can you cum for me baby..?" I whispered, my hand working up and down her entire cunt, rubbing and massaging, "I want to hear your cum... do it for me honey... please..." Up and down... round and round her dampening cunt my hand went. I stopped for a moment on her clit, swollen and hard, giving it extra attention as she moved her head now somewhat quicker and more urgent. I heard a tiny whimper from her then and knew my hand was doing the right thing. "Do it baby.... cum for me," I said slowly and quietly, "Make it feel good, baby... hump my hand... suck me good.... mmmmmm... soooo sexy..." Jill's hips now started to move in a slight circular pattern. My middle finger at last found it's way into her wet slit... she groaned deeper, this giving me a delightful sensation on my straining cock within her mouth. I could smell sweet, wet pussy inside the truck now.

"Cum baby... cum now..." I said, "cum for me now honey... ohhhhh god... cum right when I do... uhhh... ohhhhhh..." Just then, her left hand raised a bit and I saw the red panties she was offering. I grabbed them with my left hand and smashed them beneath my nose, against my mouth, inhaling deeply. That set me off. "Mmmmm-uhhmmmmm..OHHH!!" I moaned and began to explode inside her wet mouth.

As I felt the first huge blast of jiz pump thru my cock, Jill screeched and clamped her thighs closed over my hand. She bucked her hips up and I pressed hard onto her cunt, rubbing and fingering... wiggling my finger deep inside her sopping pussy. She closed her mouth tight, catching my ooze and graoning at the same time. I heard her swallow desperately as more cum shot into her mouth with the second, then the third spasm from my cock. In the mirror I could see a dribble of cum running down the shaft of my cock as Jill shot her right hand to my hand in her crotch and continued to ride my finger fuck. I moaned loud and long, giving her every bit of my seed, which she hungrily gulped into her tummy, pumping her hips and moaning along with me.

Gently, slowly, we began to settle... our lust subsiding a bit. My cock was still very erect and Jill held me inside her mouth, letting the few remaining spasms pump what remained of my load into her throat. Her hips now did a slow and sexual grind on my hand, then down on the seat. She still had it trapped between her milky thighs as her own orgasmic spasms lessened. In a few minutes she lay in my lap, licking my now flaccid cock clean of all errant dribbles as I simply held her wet, open cunt in my hand and moaned contentedly.

After we had straightened ourselves and dressed again, Jill leaned over to me, kissed my cheek very softly, then climbed out of the truck and disappeared from my view.

On my way home that night after leaving that loading dock, I found those tiny red panties stuffed down into the passenger seat cushion. Jill never asked about them.