The Homeless Womanbyjackal1©
She was standing at the corner of third and market. It was a foggy January morning in San Francisco. I was in town for a professional conference. Lowering the driver's side window of my rental gave me a better view of her. She held a "homeless, will work for food" sign. She was staring into the morning traffic and seemed oblivious of the falling rain. You could change that sign to "hopeless" from "homeless," I mused.
She was in her late twenties or early thirties I guessed. Although, she looked much older from the wear and tear of the outdoors. Then traffic moved and I lost sight of her.
On my way to my hotel room that evening I saw her again. It had rained recently and her thick blonde hair was plastered on her head. Recovered trash served as clothing, hiding the rest of her body. She held the same sign. On instinct I swerved into a parking garage drawing a honk from the driver behind.
I approached her on the street. She was staring straight ahead of her. I said,
She looked my way. Her dirt streaked face broke into a half-smile. Suddenly she looked younger. Forgotten beauty peeped from under the dirt. Her eyes warmed for a second. Then they were cold again.
"Hi," she replied.
"You looking for work, huh?"
"Yeah. You got some?" she said, pressing her lips together.
"Not really. But am alone in town tonight. Could use your company."
Her eyes turned ice cold. I could tell she thought I was propositioning paid sex. Am sure she got some of those propositions.
"Am not into that kinda thing...," she said looking away. Her nose turned red.
."..yet." And she looked at me and smiled a sad smile. Whatever run of bad luck she had gone through - still she hadn't lost her sense of humor, I thought.
"Nah. Wasn't suggesting that...you have a dirty mind...I want to talk."
She looked into my eyes.
"Come on, I'll buy you dinner. We'll order in...I have a suite...decent hotel too."
"And why would you do this again?"
"Like I said...could use the company tonight."
She stood in the middle of the living area of the suite. She breathed in the room, her eyes closed. Then gesturing with both hands, she asked,
"Now we get you all cleaned up," I said.
"And how do you do that?" she asked. Her voice was playful. Almost.
"Watch," I said.
I walked up to her and held her hands. Torn mitts covered her hands. I pulled the mitts off. Her knuckles had rug burn scars. There was dirt under her nails. Her hands were cold in spite of the mitts.
"Nervous?" I asked.
She nodded silently.
"Don't be," I said.
She was wearing a jacket picked up from a downtown trash can. Smelled really bad. I unzipped her jacket. Taking it off her I let it drop to the carpet. Underneath, a long-sleeved dark blue shirt in surprisingly good condition. Her chest heaved under. Ample breasts I noted with pleasure. I unbuttoned her shirt. Baby white skin peeked from under some serious smut. Hairy armpits. Her ears had turned red with humiliation and embarrassment.
"Just kill me, why don't you...undressing me like this!"
I was undressing her under glaring lights too.
"Try not to think that way...forget hostilities...consider me your friend...just let yourself go completely...let me take care of you please...I want to," I murmured soothingly as my hands continued working on her.
I had to get on my knees to pull her jeans off. As I did, my face was directly in front of her crotch. The stench of pee and pussy hit my nose. I tore her underwear off. A hairy pussy. Smelly too. I wrapped the bath robe around her naked body. The room was cozily heated. Yet she shivered with angst. The warm clean robe seemed to calm her. The shivering subsided.
I walked her to the bathroom. It was equipped with a Jacuzzi. I powered it on. I checked the water temperature and gestured her in. She dropped the robe and climbed in. Warm jets of water hit her skin washing off some dirt and grime.
She lay back and closed her eyes. I shampooed her hair, rubbing her scalp and temples. Then I scrubbed her skin gently. I cleaned her fingernails. Using a razor I shaved her legs and armpits. She spread her legs for me as I shaved her pussy.
I patted her dry with a luxurious towel. I used a hair drier to part her pussy lips and dry her wetness there. Also her armpits and in-between her ass cheeks. Then I put it to its rightful use of blow drying her hair.
On the way to the hotel I had stopped and bought some stuff. One of the items was a red evening dress. I had her put that on. The contours of her body protruded through the dress material. No underwear. Her breasts were full and her body agile.
She sat with her legs crossed on the couch. I mixed a drink from the in-room bar - my favorite for cold evenings - rum and cola. Giving her a glass, I said,
"This should warm up your insides."
She tossed her head to say "Whatever." The drink went down in one long gulp.
"What next? You get me drunk...we fuck...is that the routine?"
"Give up your cynicism...told you...your company IS all I need."
Another toss of that head. Her shoulder length hair fell over her face. She ran her fingers through her hair. The hand movement shifted her tits. I caught a glimpse of milky white under the red dress. She uncrossed her legs and crossed them again. The dress hiked up. Her clean shaven legs glistened in the light from the lamps in the room.
There was a knock at the door. Room service. I had ordered some food. She ate vigorously. The plates were emptied fast.
"More?" I asked.
"No, thanks. That was good though." She smiled slightly.
"The bed's yours. I'll sleep on the couch."
"That seems so unfair. I want you to sleep on the bed...with me."
"Fine. I can do that. Gotta warn you though...I sleep naked."
A big smile from her.
"That figures," she said.
"Don't know...just does."
I didn't argue that.
We lay in bed in the darkened room. Two strangers locked in their own worlds.
"Would you open the window blinds...maybe we can watch the city lights," she said.
I opened the blinds.
"What's your name?" I asked getting back into bed.
"Thought you'd never ask...Cynthia."
"Nice meeting you Jack."
"And, you Cindy."
"You don't talk much, do you?" And she giggled.
I slept - the name Cindy bouncing in my head.
When I woke up I was lying on my back. I had a raging hard on pushing into the comforter on top of me. She was licking my nipple. Her tongue deftly flicking and engorging my little things. My cock was reacting to her erotic touch. She sensed my wakefulness. She put a finger on my lips.
"Don't say anything...just let me take care of you," she whispered.
"You stole my line."
"Yeah, I know," she giggled. Then her tongue found my cock and the pleasure waves exploded in my head.
Her tongue unleashed hidden, never before explored, pleasure points as she explored my crotch area.
"Let yourself go...be loud, if you need to," she said in-between slurps. I had to. Losing my usual inhibitions, I groaned aloud with pleasure. Never before had I groaned aloud during sex. A first for sure. It felt good. She matched me with a moan. That sounded sexy. Small animal cries of pleasure. She was pleasure moaning from sucking my cock - sexy thought. My cock wanted to explode. She stopped sucking just when it would have.
"I need you inside me," she said, "Do you mind?"
What a question. No, Cindy, of course I don't mind.
She held my cock as she went on top of me. Facing away from me, she guided my cock into her pussy hole. Then she moved. And, did this babe move! She fucked me like she had not fucked for years. First kneeling, then squatting on my cock, she moaned my name and rocked my cock.
"Oh, Jack...oh, Jack...Oh-Oh-OH-JACK!"
Then she would go, "Uh-HUH, HUH, UHHHH."
I lay there watching her naked ass and back. Her head thrown back. Her pussy quivering and slobbering over my cock. Her ass slapping into me.
I had no control over her. She was in her own world. I could only watch. She looked back once, breathless. To see if I was all right.
"Go for it, hon," I said. That was all the encouragement she needed to continue fucking my cock like the last cock on earth.
Finally she got off me giggling.
"Gosh, I needed that!" she said.
"Yeah, you were ready to feed, darlin'!"
"I was. That felt soo good. You are so good, Jack...wish I had a guy like you instead of that bastard!"
"Well..." I wanted to know her past. But she stopped me in mid-sentence by putting a finger on my lips.
"Not tonight...no talk...just fuck-fuck, ok?" And she giggled again.
"Tell me... what's your pleasure, Jack? What do you like?"
"Hmmm...I'd sure to like to fuck your ass," I said.
"Oh." She pressed her lips together. Then she smiled.
"Vaseline, please?" She was giggling again. "You know it hurts."
"I can do that."
"Do you want me on my back or doggie?"
"On your back...I want to see your face as I fuck your ass."
"Jack! You bastard...I knew it!" She was giggling away.
"What did you know?" I asked.
I was greasing her asshole.
"What do you mean?"
"Can't explain...just you...you are cute."
"Don't talk so much...I want you in my ass."
I didn't waste time. Pushing back her legs, raising her ass, I sank my cock into her tight bum hole. Her eyes closed, she grimaced with pain. I pressed harder and my cock slipped off. The Vaseline had made her hole entrance slippery. She opened her eyes. I reached down and using a hand positioned my cock. I probably didn't get it right as she said,
Reaching down with a hand she guided my cock. I felt her rim on my cock's head. I couldn't hold back my excitement. I pushed down. My cock sheared into her tight hole. I was determined not to pop out this time. I kept pushing till I was all in. Then I held myself still.
Her eyes were closed. Her face contorted in pain. Head thrown back.
"Oh, Jack. Move. Fuck me."
I moved. I wanted to fuck her. Man, did I ever want to fuck Cindy's ass. But, all the excitement till that point had taken its toll on my cock. I managed a few strokes and then I felt my cock explode in her tight ass. Couldn't stop myself. The sensation of her tight hole covering my cock was too much for me. She lay there as my cock deposited my semen inside her ass - hands squeezing her tits, face reflecting the pain - just looking extraordinarily sexy.
Then I rolled off her exhausted. I get so sleepy after doing it. I slept.
I woke up. Sunlight was streaming in through the window hitting my eyes. I looked over. The bed was empty except for me. I called out her name. Silence.
The red dress was on the dresser with a note on top. Two words written on hotel stationary said - "Thank you."
I spent most of the day driving through downtown San Francisco searching for her. Eyes desperately seeking a homeless woman walking the streets. When I boarded the plane home that night my heart was heavy. I said goodbye to the City by the Bay and one very special denizen.