Mutually Beneficial Arrangement Ch. 01

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.

And while I was making this argument to myself, I was filling out the application for the sugar daddy website. I honestly don't even remember making the decision to do it. I had somehow just made the decision in a void, and then talked myself into it after the fact. By the time I had decided that, really, I had always been attracted to older men, maybe even old, overweight men who wouldn't have a lot of energy, my photo and a thin bio was posted on the website.

Once the profile was posted, I was almost shocked to see it on the website. I swear, for a moment, I tried to remember who had made the profile for me. But within a couple of seconds, my phone buzzed and I saw a small, blue envelope appear on my profile. Someone had contacted me! For half a second, there was a thrill that it had actually worked! Some wealthy older man had contacted me! But then, that thought made everything...real. My profile was really on the site. Real people were contacting me to date me and give me money. Suddenly, I wasn't so sure I didn't feel like a whore.

"This is crazy," I said aloud. My son was batting at some toys in his playpen and he turned to look at me as I spoke, "Keep playing sweetie," I said and he turned away from me. What sort of mother was I being? I looked down at my phone, clicked on the "settings" button. I told myself that I was going to click on "deactivate." My finger lingered over top of it for a long time. Then I quickly logged out instead, and refused to think about what I'd done.

When I woke up in the morning, I allowed myself, for the first time, to think about the fact that my profile had been up all night. Men had been searching through it, judging my picture. Sending me messages. I felt dirty, just thinking about it. But, at the same time, I was curious. I realized that that was one of the reasons I hadn't deactivated the the account the night before. I wanted to know what would happen. And, of course, I was still thinking desperately about money.

Flooded doesn't even begin to describe what I found in my inbox. I had never seen anything like it. There were dozens of contacts. The first two pages of my e-mail were all new emails from the sugar daddy website. And that was before I thought to look in my spam folder. Eventually, my email had just started dumping them in there. There were at least as many. In all, I think 50 people had contacted me, based on my ad.

"Guess I am better looking that I thought," I said to myself, and I smiled a little despite myself. I mean, I couldn't really pretend it didn't feel good to be so...desirable. Even if part of me knew it just meant I was the prettiest whore on the whore website.

"Well, now I know," I said to myself and I started deleting the emails. I told myself that I had just been curious, and my curiosity was now cured. But after deleting ten or so e-mails, I saw the subject line of one, "You are are beautiful." It said. I didn't even think. I just clicked the email open. I was assaulted by the picture of a very old, overweight man leaning against a Porsche. I didn't read anymore. I closed it and deleted the email without reading anymore. I couldn't even imagine a man like that...on top of me. He looked like my high school chemistry teacher (but richer). I couldn't do this. I started deleting emails again.

My eyes fluttered over the subject lines as I went. "You're a perfect little kitten," and, "Let me show you a good time,"and "Let's talk about going out on a date." No matter how friendly they sounded, each offer made me feel more and more like a prostitute. I clicked on a couple, and each time the man seemed to act like we were just setting up a regular date. Like I would want them even if we hadn't met on a seedy sugar daddy website. There was never any mention of money. And that was somehow worse.

Oddly, it was the extremely business-like message "A Mutually Beneficial Arrangement" that stopped me in my tracks. I had deleted all but a handful of messages when that one reached the top of the pile. I set it aside, deleted the rest (although another one had come in while I was screening my emails, and I finally deactivated my account after deleting that one as well). Once again, just out of curiosity (I told myself), I clicked on the "Mutually Beneficial Arrangement," Email. It said:

"Dear Lissie, I won't waste your time. I would like to meet you in person to discuss the possibility of working out some sort of dating arrangement. My initial offer is $1,000.00 a week in allowance, but I find you attractive and we can discuss adjustments to that amount at our first meeting. If you are interested, please text me at the number listed below. I will text you back a time and location to meet. It will be a public place and I will buy you a nice dinner, even if we ultimately decide not to do business. Please, do no call me. I work long hours and will not be able to discuss our business while at the office. I hope to you hear from you. Sincerely L.S.R."

* * * * *

It was eight o'clock that night when I self-consciously entered the nicest restaurant in town. I didn't really have the right clothes for an upscale Italian restaurant. I was, ridiculously, wearing the red, strapless dress I had worn to my senior prom (the night I got pregnant, in fact). I knew it was the wrong thing to wear. But the only other remotely dressy thing I owned was a puke-green bridesmaid's dress I'd worn at a friend's wedding a year earlier. So it was either prom night or jeans.

"Can I help you?" the hostess said as I stumbled in the door. I could see her eyeing my ridiculous clothes and felt my cheeks grow redder than my taffeta. Not for the first time, I decided that had made a huge mistake in texting the L.S.R. at the number listed in the email. It was just... $1,000.00 was so much money. That was $50,000.00 a year! I wouldn't have to do any other work! I just kept telling myself "there is no harm in getting a free meal." And I had texted. And almost immediately, L.S.R. had texted back to meet that night. In a sort of daze, I had asked the neighbor to sit with Aiden and gotten myself ready. I had even shaved, even though I promised myself I wasn't going to actually do anything. Just discuss business.

Now, standing in front of the hostess, I felt absolutely absurd The money had completely overwhelmed my reasoning. Less than twenty-four hours ago, I had set up the account, a week earlier I had dismissed the idea entirely. And now I was actually meeting some man who hadn't even bothered to put his picture or his full name in the email. Everything about this felt completely immoral. I thought about turning around and leaving right then. There would be no harm done, if I had done that. I could go home and finish packing for the apartment that I couldn't afford. I briefly became aware of the intense pressure I was under.

"Richard, table for two," I said in a small, squeaky voice. The hostess nodded.

"The other party is already here, please follow me," she said, and I felt my stomach drop to my knees. I was already desperately nervous, but now I was approaching L.S.R. And the absurdity of what I was doing seemed to double my anxiety.

I followed the waitress deep into the restaurant. It was crowded, which was good. And I could hear gentle conversation, the clinking of glasses, the scrape of forks. I almost walked into the hostess as she stopped in front of a table. My mind went blank, I couldn't even remember what I was supposed to do.

"Your seat, miss," the hostess said, gesturing to the table. My eyes were down at my feet, I couldn't bear to look up at L.S.R. I mumbled something to the hostess and sat down heavily. I knew I was probably making a terrible impression. But I didn't know what to do. I could barely breathe.

"Good evening," a deep, smooth voice said. But not nearly deep enough. My eyes flickered up quickly and I saw a beautiful woman sitting across from me. She was older than me, actually probably the same age as my mom (though she clearly hadn't lived as hard as my mom had). She had dark brown hair that was pulled back into a tight ponytail. She had a high forehead and large, dark eyes. She had a small nose, thick, red lips, and a delicate chin. Her throat was long and thin. She had narrow shoulders and long arms. I saw she had large, full breasts that were closely squeezed into a professional, white button-up blouse. She was wearing a black suit as well. I couldn't see her hips or her legs, but she appeared to be well built.

For a long moment, I stared at her, my head tilted to the side and my mouth open. It was like I had typed a non-existent website into my brain and my browser couldn't find it. "Not a valid input, cannot display." I was here to meet a man. The hostess had seemed certain this was the right spot. The woman sitting across from me didn't seem surprised to see me. Suddenly, it dawned on me. My eyes went wide and my breath caught in my throat.

"Ma'am, I am so sorry!" I said, as quietly as humanly possible, "I had no idea that... that the guy was married. I never would have come if I had any idea that...I am just so humiliated and so sorry. I don't know anything about him and..." The woman didn't say anything. She didn't appear to even get angry. Maybe he did this all the time. But then the woman's hand rose up to her mouth, it had no ring on it, and I saw her smiling. She covered her lips, and I could hear her laughing. I stopped talking, sputtering.

"That was adorable. You're very sweet," the woman said. Then she extended her hand, "I am Lily S. Richard. Nice to meet you, Ms. Gold..."

"Lissie," I said in a faraway voice.

"I realize that my email was sparse, but my profile states that I am a woman. There was a link to the profile in the email," she said.

"I, uh, didn't look," I said and Lily laughed. A pretty, musical sound. Not at all mean-spirited.

"Clearly," she said.

"I am really sorry that I didn't read the whole thing," I said, still embarrassed, but extremely relieved that I wasn't sitting across from someone's wife. But still, I was a little confused, "So...you are looking for..."

"An arrangement, yes," Lily said in a quiet voice, and I realized that I needed to be careful about what I said. I looked around and remembered that there were a lot of people present.

"Well, Ms. Richard..." I started.

"Lily," she interrupted.

"Lily, I am, like, really sorry that dragged you out here and you don't have to buy me dinner or anything. I am," and then I dropped my voice and leaned forward, "I am not really attracted to women. I am not like...against it or anything. It just isn't for me." It felt excruciating to say it. I was already humiliated. Now I felt like I was sort of going out of my way to make this nice, understanding woman feel bad. But Lily seemed unfazed.

"So you are attracted to old men who want to give you an allowance?" she asked and raised her eyebrows. I sort of shrugged.

"No, I mean...no," I said. I mean, I guess I had been preparing myself for the possibility of something way more disgusting than Lily when I got here.

"Let's just discuss what I had in mind and we can see if we can work something out that works for both of us. Frankly, you're cuter than your pictures and 'not being interested' is a good opening negotiating position for you," she said. I lifted my hands up defensively and shook my head.

"Oh, no..." I said, "I don't want to waste your time. I am not going to..."

"You're cute, but skinny. Order yourself some pasta and just listen. If you stick to your guns, then you go home afterwards with a full stomach and nothing more," she said. I had skipped lunch that day, trying to save money, and my stomach growled as I looked at the food on the tables around me. I looked over at Lily again and she smiled warmly.