Hello Readers! This is part one of three. All three parts are drafted and they will be put on the site one at a time. I keep a big, master list of story ideas that I refer to when the time comes to draft something new. This story has been sitting and waiting for me on that list longer than any other idea. I came up with this idea over ten years ago and I have been rolling it around every since. The time never felt right. This will be my 100th story segment posted on Literotica. It seemed like the perfect time to finally write this out. So thank you all for reading and enjoying my stories over the years. Let me know what you think about this one! And don't worry, there are still plenty more ideas on the list.
Chapter 1: A Purely Financial Affair
I scrolled, panicked, through my old emails. And I was praying, while I did it, that the system hadn't already automatically dumped it from my "deleted" file where I knew I had left it. There were hundreds of emails in that file, mostly ads, and I couldn't remember exactly when I had deleted the thing I was looking for. And it was hard to read any of the subject lines from my emails through the tears.
"Come on, come on! Where are you?" I said, my voice sounding shrill. I tried to be quiet, knowing that Aiden, my two year old son, was sleeping in the crib just a few feet away from my desk. Having a toddler in an efficiency apartment was not easy. But then, if my life was easy, I probably wouldn't have been desperately searching for the needle of a six-month old email in a haystack of Sephora ads.
The fact of the matter was, my life, at that moment, was a disaster. A totally and completely predictable disaster. I had been living on the knife's edge of catastrophe ever since Aiden was born. I had a job that paid just above the minimum wage. After taxes, groceries, rent/utilities, paying the woman on disability next door to watch Aiden while I worked, and then the insurance and gas on my car, I usually ended up with about $5.15 at the end of the month. Not an exaggeration. My plan had been to save that up all year so I could buy Christmas presents for Aiden.
But that evening, my car had refused to start. A guy down the hall was a mechanic. He said that the transmission on the car (which was 20 years old, so the same age as me) was completely shot. He said he could do it for me at cost, but it was still going to be $1,400.00. Which meant, in essence, that I was dead. I had $30.90 in a jar on my counter. I had $1,500.00 in credit card debt still from the costs of Aiden's birth and the next minimum bill was due in two days. I was already maxed out on that, I had only been paying the interest. The title loan place said they would only give me $400.00 for a loan against my car. And I could only get $600.00 for a payday loan at like a million percent interest. My dad was in jail and had been for most of my life. My mom was poorer than I was and any spare money went to booze. I didn't have any other family. My son's father..I mean please.
And so I was searching desperately for the email I'd deleted six months earlier. The only lead on serious money that I'd had...ever. If I didn't find that, I wouldn't get to work. And I wouldn't have money for rent. Or my credit card. And Aiden and I would be on the street. Where we would die of starvation or something. And that sequence just kept running in my brain over and over again. Fired. Evicted. Homeless. Dead. Fired. Evicted. Homeless. Dead. Fired. Evicted. Homeless...an intense wave of relief.
"Oh fuck, thank god!" I said, and I actually leaned forward and kissed the screen of my cellphone. It was the email I had been looking for! To: Lissie Gold (that's me); From LSR80@___mail.com. Subject line: A Mutually Beneficial Arrangement.
* * * * *
When I had received the email six months earlier, I had thought I had reached my financial low point. That had been when the apartment building I was in at the time had been sold to a developer and was going to be torn down to make way for something new (it turned out to be a discount grocery store). I was told that when my lease was up (the next month), there would be no renewal. I had already been sweating the increase in rent for the next year, but the idea of finding a new apartment was a whole different order of difficulty. My town didn't have many apartment buildings, and the one I had been in was, by far, the cheapest. The next shittiest place was $75 more a month. Which was basically all I had at the end of each month back then.
I had spent the last month at that apartment searching for a new job or some other way to pull in a little bit more money. I had about a year's worth of credits at community college. But that was basically it for me in terms of marketable skill. I didn't trust my car enough to Uber (which turned out to be wise) and I had a friend who got burned on a multi-level marketing thing so I knew better than to try that. Though I would be lying if I said I wasn't tempted.
Once, I searched "ways for single moms to make a lot of money easy," or something like that. I searched through about a dozen pages of results before I saw something that caught my interest. Well, caught my interest in the sense that I was grossed out by it. I saw a website that said it would hook up young, attractive single moms with "sugar daddies" who would give them an "allowance" while dating.
"That's just being a hooker," I said, clucking my tongue and shaking my head, thinking about girls who were gross enough to consider it. I moved on.
But the days started to pass. My searches on the internet starting to become circular. I kept seeing the same "direct sales" or babysitting suggestions over and over again. I didn't even know where to begin on some of the things and I knew from experience that the others were dead ends. And, as the end-date for my lease got closer and closer I started to find myself growing more desperate. Eventually, I signed a lease at the place that cost more money and asked some friends if they would help me move. So I was on the hook for my security deposit and more rent and I had nothing but the same shitty job I'd always had.
Sometimes I would find myself thinking about the "sugar daddy" posting that I had seen. Usually, I wouldn't even realize I was thinking about it. Just fantasizing about some man (I didn't really think about who was or what he would look like or what he would want from me. Just some guy) who would give me money to go out on nice dates. Like a movie star's girlfriend. And I would grow jealous. And then I would realize what I was thinking about, shake it off, and go back to searching.
I found myself, one morning, stopping to look at myself in he mirror. I was an attractive single mom, after all. I was only 19 at the time. I still looked like a high school girl. Long, dirty blonde hair, big green eyes, cute nose, soft features, high firm breasts, narrow waist, round hips, and tight little butt. I had long legs that looked good in jeans or in a skirt. And then I would think to myself "why are you rating your appearance." And I would try to pretend, to myself, that I was thinking that maybe modelling was an option. But I knew I wasn't quite good looking enough for that. What I was really thinking about was what sort of attention I could get from prospective sugar daddies. And I would feel deeply ashamed.
It was a week until my security deposit was due when I began to ask myself why I was ashamed about those feelings. I told myself that in thinking about it for awhile, I had really gained some perspective. Learned to stop thinking about things like I was some dumb kid or something. I mean, it wasn't like a young woman with a wealthy older boyfriend was a...hooker or something. Some women just liked older men. And who cared how they met? It wasn't like people who were into cross-generational relationships were likely to hook up on Tinder or something. There had to be a place where those sorts of people could meet. And so what if, sometimes, the older man gave his girlfriend some money? That was part of being a relationship. Men bought dinner for girlfriends and stuff all the time.
