The Homeless Old Man

Story Info
A mature woman made use of a homeless old man to satisfy her.
969 words
4.12
68.4k
42

Part 1 of the 2 part series

Updated 06/08/2023
Created 08/19/2017
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I lost all my retirement money, house, an old car, wife and son. My wife left me when our son was a year old. She couldn't bear with my gambling habit knowing l never could change. I gambled with every single cent I had always hoping for the "LUCKY BREAK" that never came, first my retirement money, then my old car and finally my house all wasted on the false hope of a Big Wind Fall. Now, I am left with a few old shirts and two pairs of worn out jeans stuffed in a worn out bag.

For my 79th birthday, I had only a stick of cigarette I saved for the night. By mid night I would be asleep. Sometimes I was woken up by late night commotions like street brawls and pub quarrels and couples making it out on deserted mall stairs. I was never bothered and would not be bothered either. I once stood up for a young teenage girl who was almost gang raped. Probably a date with her boy friend to the pub gone ugly. I got beaten up instead and had to endure the aches and pains for many days.

Among the many daily shoppers, there was a woman could be in her mid thirties, always dressed in short skirt with tight round ass, sexy thick thighs and matching legs going all by herself. She never talked to anyone and seemed to have no one in her life. When ever she shopped here, she would always eye me from the corner of her eyes. I could imagine the message in her mind. Wasted old man, brainless gambler now destined to rot alone . You deserved it all. Huh! Who cares I reasoned to myself. I never begged, never robbed, never cheat and never stole so who cares.

It rained heavily that night. It was wet everywhere, drains overflowed. Shops and malls closed early though it was only around 9 pm. I was lucky today. A drug peddler friend gave me half packet of cigarettes. That I smoked slowly with nothing to look forward to. Then curled facing the wall slowly drifted into deep slumber.

A pat on my shoulder woke me up. I turned my head and saw a woman squatting near me. You lost something? I asked. Whenever people approached me, it's asking me if I saw their bunch of keys, umbrella, purse and even about certain car passing this area. They thought I must have seen everything that occurred here.

I want to touch you. I want to touch your penis. She whispered. She reached out and undid my jeans. I was dumbfounded. I didn't resist nor obliged. She moved her hand in search of my cock. Took my cock out and displayed my balls. My soft and lifeless cock in her hand gave her some fascination. She began to tug my soft cock. I hardly felt any sensation at all. I lost my appetite for sex many many years ago.

Soon my cock started to respond. It grew slightly. I wondered when will she stop. I thought to myself, get over with it lady but remember to drop some coffee money. Her other hand started to massage my balls. My cock stiffened, I let out an involuntary moan. Tell me when you're cumming she uttered. I felt the sensation built up. The urge to ejaculate came to an unbearable point. I announced to her I was cumming. She bend lower probably to have a closer look on a cumming cock. I couldn't hold back any longer and the cum came. It was a strong burst of sensation I had never experienced such a strong climax any time before. She continued stroking while my cock throbbed in her firm grip. Then she let my softening cock slip from her cum covered hand.

Wiped her hand on jeans, she stood up, tool her purse and dropped $15 on my chest then hurried off into the night. I slipped my wet cock back into my jeans. The same thing happened for the next three nights. Each time she would leave $15 behind . $15 for playing my cock was to me a good income. Then the following few days she didn't appear. I couldn't be bothered either.

After a quiet week, she came one night. Squatted near me and without a word started to undo my jeans. Taking out cock and balls. She stroke me till my cock stiffened. She straddled me and guided my cock into her pussy. She was so wet that made penetration easy. She started pumping. Took my hands and placed them on her tits. So I started to massage her round firm boobs. Her breath became heavy. She held my hands and stationed them on her nipples. She let out a moan, I felt her pussy pulsating, even her anus throbbed against my balls.

She paused to rub her clit, then reached for my balls and began massaging arousing me to another level. She rode and grind. Her juice flowed down my crotch. This time I presumed she was in for a big one. She panted, whined a little, then she let out a deep moan, I felt the rhythmic thud of her pussy and ass hole muscle as more warm juice ran down my crotch. She clenched my upper arm in an iron grip.

She dismounted and jerk to finish me of. My body arched forward as my cock reached a point of eruption. Once again she wiped her wet hands on my jeans, stood up, adjusted her panty and skirt then her bra and t -shirt. Took out her purse and dropped $50 note on my chest. Hurriedly she stepped into the night and then serenity crept back into the space beneath the concrete stairs.

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AnonymousAnonymous5 months ago

Well written, pity she didn't take him home for a good long pussy suck and fuck.

ModdyModdyover 3 years ago
Very erotic

Reminds me of my first time with an older homeless guy.He was 47 years old and ruggedly handsome.I fantasized about him since I was 14 and finally acted on it when I was 18.I was a virgin and was so turned on and lusting for the scruffy older man in jeans and flannel shirt.He let me have my way with him and he was so eager to please. It was mind blowing. Scruffy older men are my weakness.

trishotoy99trishotoy99over 6 years agoAuthor
chapter 2

Chapter 2 will be submitted for publication if the story get strong support from readers. Thank you.

AnonymousAnonymousover 6 years ago
Asleep at the wheel

Thought for sure she was going to blow you or there was going to be anal. Well, maybe next story if there is a chapter 2...

AnonymousAnonymousover 6 years ago
And Then He Woke UP

Sweet Dreams

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