Posh Milf Needs Homeless Man


A ‘posh’ older woman who desperately ‘slums’ for sex is a recurring fantasy of mine. So I wrote this story (‘Humiliation Addict: Rich Bitch & the Homeless’) to push all those buttons. Celia is posh – very posh, and she seeks her satisfactions among the homeless boys she sees selling the magazine to ‘help the homeless’ the ‘Big Issue.’ To her these disadvantaged young men are the thing she desires most. Or are they? Maybe what she really wants is the degradation and humiliations that comes from having to submit to one. Either way I enjoy her ride. I am still in two minds as to whether she does…..


Celia watched the young man hungrily swallowing the hot soup she had brought. He still looked chilled to the bone. His pathetic blanket and bulging plastic bag lay behind them on the back seat in the BMW. Up front she couldn’t take her eyes from him; her very own much anticipated bundle of nothing very much.

The car’s heater was on full, they had been sitting there for around fifteen minutes. The windows were starting to steam. The weather outside was beginning to frost; it was going to be a brutal night for the homeless.

She was thankful for such weather.

It had taken her quite some time making the soup that afternoon. It was important to her that it be the best it could be. She wanted, in a peculiar way, to impress; to know that what she offered wasn’t just something throwaway. Something cheap. She had used fresh tomatoes and a selection of herbs from her own garden; had blended and seasoned with care and attention, before thickening it to just the right consistency. Not too thin, not too thick. And when finally she was happy with it, she placed her face directly above it and quite deliberately spat in it. At the time she could not have said why, but now watching him drink it, she felt a mixture of self-disgust and guilty gratification. Shame at her contamination mingling with a personal satisfaction knowing he was drinking something of her. Somehow it felt good to be bad.

He had not said a word to her yet, just nodded when she had offered him some soup and the warmth of her car. She wanted to ask him so many questions. How long had he been homeless? How had it come about? Did he have any family? What did he think of women like her; the do-gooders, the soup bringers? The middle-aged, middle-class who took such an interest? But she couldn’t find the words to be so intrusive while he was warming his hands on the flask and looking so pitiful.

But time was pressing, it was already past midnight; soon he would be gone and so she had to approach the reason she had brought the soup; the real reason why she was here at all. Her stomach felt fluttery with excitement as he drained the last drops.

She cleared her throat; she could feel the butterflies in her stomach becoming large flailing moths, like tiny aliens trying to beat their way out. From her bag, she produced a single twenty-pound note. She held it up, showing it, offering it. She knew there was a chance he could just grab it and run. There would be nothing she could do to stop him. Nor would she want to. Let him have it, it was worth it to feel taken for granted, used by this quite unfortunate boy. She would understand if he did.

But he didn’t. he just sat there looking at it with watchful eyes, waiting for her to speak.

His eyes were locked onto hers. Despite her fear, despite her shyness, she forced herself to say the words she had rehearsed in her head so often. ‘I have twenty pounds here; I will give it to you if you will…well…allow me to give you a…a…wank.’

To her it sounded wooden, overdone. Much too matter of fact. She felt she had embarrassed herself. She looked down and wondered if he would just leave. Perhaps that would be for the best. He could keep the money. This had all been a bad idea, especially after last time. Whatever had she been thinking? And yet her proposal was the accomplishment of a moment she had dreamt of a thousand times.

But at least she had said it; at long last said it out loud, not just inside her head. This was reality, no longer her solitary fantasy. The words were out there, in his head now. All she could do was wait. What would he make of them? What would he make of her?

When she looked up his face was set in a mask, she could not read his thoughts or his intentions. Perhaps he was just wondering just what she was about. What she was up to; possibly what the catch was. She was wondering exactly the same thing. What was she about? She wasn’t even sure herself. She just knew she had to come here, had to do this. Too much time had been wasted in just thinking about it already. She knew that it was as much about shaming and humiliating herself as the sex itself. Although the prospect of sex excited her more than she dared admit – even to herself. With every fibre of herself, she ached to feel his cock – his young, hard, dirty cock – beneath her fingers.

The young man nodded. ‘Okay’, he said. ‘Here?’

FROM Amazon:

Wealthy divorcee Celia has a secret sexual compulsion. She has a deeply felt need to be sexually humiliated. Her obsession focuses on the homeless youths she sees around town. Celia lives an affluent and privileged life but harbours secret dreams of defilement and debasement. Her fantasies are of rough and sordid sex at the hands and bodies of coarse and vile young men. Her needs run bone-deep; they both repulse her and draw her.

One day, when her fixation grows too much, she ventures out from her comfortable world. She ventures into the very heart of her darkness… into the bad part town in search of her perverse humiliations and satisfactions…
…and she gets more…much, much more than she bargained for.

To download this title from Amazon, please click HERE

Other posts you may enjoy:

If you are a fan or humiliation and degradation your tastes may run to the darker side of sex. My story In Her Daughter’s Footsteps: A Journey into Sexual Hell, features a woman who wants to relive her dead daughters experience at the hands of many and various men with very particular tastes.

Jealous Mummy: Be careful what you lust for How can a mother be jealous of her own daughter? Answer: very easily. Especially when that mother has to lie awake listening to them having sex in the next room. But the boyfriend in question has an even darker a gender than just having the mother…..

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