This story is based off a real encounter I had a few years ago, the only changes are to make the story more readable -- otherwise this is 100% accurate.
If anyone has any feedback on this scenario -- or would perhaps like to act it out -- please get in touch.
This tale begins not unlike many others you may have heard, it began with an online advert on craigslist. As is typical of the site, it was written in poor English, and was deliberately vague to avoid it being flagged for removal. It read:
'Looking 4 investers'
Admittedly I half-expected some sort of crypto scam, but just to be sure I clicked on it -- and was pleasantly surprised when I saw the following:
'f41 need cash for small business -- message for details'
"Perfect." I said aloud.
I suppose I should explain a little about myself first. For the most part I'm just your typical young English guy, with a decent job and my own flat. Whilst I'm no Brad Pitt, I am reasonably attractive and athletically built from my time in the gym. However, this benign description belies a much more interesting aspect of me, I'm an extremely kinky man who has already had sex with over 20 people -- and with each encounter I never wear a condom -- and I NEVER pull out.
I absolutely LOVE the feeling of slipping inside of a tight, bare pussy for the first time -- completely naturally - with no barrier between me and my woman. I feel her most delicate place in its entirety; her juices, her skin melted to mine. And it always ends in a deep, natural finish inside of her. As I spunk deep into her pussy and womb I'm marking her as mine forever -- regardless of who she's with in the future, my seed will be absorbed into her body, and indeed her very being.
Following a nice deep creampie, I especially enjoy holding my woman tight, ensuring every last drop is kept in her female depths. My cock remains fully hard balls deep inside of her warm creamy pussy -- and when I feel ready I'll begin to thrust again slowly and deeply until I add another thick load to her sloppy, claimed femininity.
Whilst, like any man I enjoy making love, I also have a more dominant side. I've also been known to indulge in being a daddy, breeding sissies -- and perhaps more controversially, engaging in raceplay. There's simply nothing quite like slipping inside of a tight, natural, foreign pussy for the first time. The moment my big white cock touches her strange petals, my precum dancing across her lips, our opposing fluids mixing, the taboo crossed and another on the way -- pure ecstasy. And then, once I'm inside, using it like I would a fleshlight, calling her a dirty brown whore and having her beg daddy to give her a beautiful mixed baby in her exotic womb.
And so begins this particular story. Seeing 'f41', I knew from previous experience that older women were likely to have fewer limits than younger ones -- and charge much less. Thankfully, they're also used to having proper spunky bareback sex and taking a man's sperm where it belongs. And in terms of pleasing a man, they will work much harder to get it.
However, dragging myself back to the reality of the situation, there was still the element of the poor English, meaning it could easily be a scam. I decided a minimalist reply was best -- it was something along the lines of:
"How much are you looking for?"
My confidence in the situation was not exactly helped by the fact that it was a man who replied; 'Joaquim' he was called, who said:
"Hi I'm looking for men to help my friend out she's 38 Black BBW big tits needs money tonight."
"Fuck yes." I muttered in approval.
For those who haven't experienced a fat older woman before, they are a... unique experience. I would be lying if I said they were better than a healthier, more attractive woman -- especially if a younger one. However, there are few things in this world like a fat heifer trying desperately to please you in every way to keep you interested. For the most part, you can simply climb on top of her and she'll do all the work -- no foreplay required -- just slip inside and she'll make sure to push back at you, talk dirty and most importantly, ensure you bare cock is as deep as possible when you climax totally sheathed in her fat, welcoming pussy. She'll then hold you inside of her for a while afterwards, comforting you and coaxing every last drop of seed into her.
Once again reminding myself of the situation at hand, obviously there are major red flags here. Many questions entered my mind: Was he her pimp? Was this another old bi man wanting a wank fanstasy? In order to discern this, I decided to take a bold step and ask for 'her' number to get her to verify her identity. In short order he gave it to me and said to mention him when I messaged, and so I did, saying:
"Hi, Joaquim gave me your number saying you needed money -- what is the money for?"
To my pleasant surprise, I received an almost instant reply, stating:
"I'm a small business owner of natural beauty products, I need some money for start-up costs."
Very straightforward, I like it. I returned the favour:
"So would you be willing to come to my place and have sex with me for some money? If so, how much would you like?"
Admittedly having the other party set the price is not the most cost effective way to do this, regardless, without hesitation she replied:
"40."
"Wow, I've hit the jackpot here!" I thought.
Looking back on it this should've set alarm bells ringing for a scam, but, it'd been so long since I had felt myself shoot deep in a tight pussy that I overlooked all of those considerations.
"When are you free?" I asked.
"I'm free until tomorrow at 3." She replied.