Mutually Beneficial Arrangement Ch. 02

Hello Readers! This is part two of three. All three parts are drafted and they will be put on the site one at a time. Let me know what you think!

Chapter 2: Regular Work

It was sort of unbelievable how quickly we were able to settle into a regular thing. Lily was very understanding of the fact that I had a son and a life outside of our arrangement. She also encouraged me to keep my job. Both to supplement my income, and to be sure that I didn't have a giant hole in my employment history if I ever wanted to do something else. She told me that was important, and I believed her. I believed everything that Lily ever told me. She knew so much about...the world.

But we managed to have at least one date every week. Sometimes, when I could swing it, we would do a second date. But that was sort of rare. Usually it was Friday night, when Lily liked to unwind after an 80 hour week. We almost always went out. A dinner, a movie, something. We never went out in the town where I lived, or near Lily's home or work. Sometimes, she would drive for over an hour just to go out to dinner. I didn't mind, I appreciate the discretion as much as she did.

And I appreciated the dates! I had never had fun like that with someone before. I mean some of it was just that money was no object to Lily. We ate amazing food (and she bought me nice clothes so I looked good while I ate it), we saw new movies (not the discount theater), and did, like, cultural stuff I didn't realize that I would want to do (museums, art shows, antiques). But, even if we just went out to eat and sat and talked for an hour or two afterwards while it was great! Lily was funny and sweet, and she had like a million ideas for things that I could do to get my life together. I was no longer intimidated by her (much) and she was no longer formal with me (unless we discussed money). I very quickly came to see Lily as less of a boss, and more of a friend and mentor.

Well, kind of. Because after every date, we would go back to Lily's place and we would have sex. And after we had sex, I would get paid. And any lies I told myself about friends and mentors would instantly evaporate. And I would feel dirty again. Feel like a whore.

But it was sort of strange. I mean, I definitely felt like a whore. But...I don't know...I didn't hate it. I had done a lot of things in my life, and none of them very well. I knew I was as good a mom as I could be. But other than that, I was pretty much terrible at everything. But I was good at this job. I mean, Lily didn't have to say it. I knew that I caught on quickly. I knew that every time we were together, I gave her more pleasure in new and different ways. I admit...with some of the money she gave me I bought books about lesbian sex and read them so I would be better at it. And even if I didn't need Lily to say that I was good, she did! Often. And I got more satisfaction out of that than I ever had from a job before.

And it wasn't just that. The sex itself was actually really, really good. That first time, with Lily, that was the first time that I had ever had an orgasm with another person. But after that, I did it every single time with her. Even when I was focused entirely on her, it was like she knew just what buttons to push, what could make me cum. And we were always trying new things. Things I'd never heard of. Things that I realized were a little bit kinky! Things I didn't realize I loved until I tried them. It was a job, of course, but a job that made me feel fulfilled and made me cum. What was not to like?

Still, I think Lily encouraged me not to think like I was her whore. Whether that was for me or for her, I really didn't know. But I appreciated it. I mean, she took an interest in me as a person. I remember once, about three or four months after our first date, Lily and I had gone out to dinner but returned home early to have sex. We were already growing more comfortable with other another, and we spent a pleasant evening in Lily's bed (we no longer had sex on the cold tile on the first floor, which I was happy about).

I think that Lily had already sensed by that point that I was not necessarily in a rush to leave when we were done and that I felt strange when she handed me my money right as we finished. I didn't say anything, she just picked up on it. And so that night, after we finished, we lay in bed talking for awhile. Lily was sitting with her back against the headboard, her legs covered in the sheet, but not the comforter. I was laying with my head in her lap, my face directly below her beautiful breasts, and she ran her fingers through my hair. Sometimes she would bend forward and her breasts would press into my face, and I would giggle and kiss the soft bottoms. But the situation was more relaxed than sexual.

"It is almost midnight," she said after a long while, "Do you need to get back to your babysitter?" she asked. She never referred to my son, almost like it was inappropriate to discuss him. Only my babysitter.

"You trying to get rid of me?" I asked, with faux concern.

"Take a hint!" she said loudly and laughed. I made as though I was going to sit up, Lily grasped my hair and pulled me back down.

"Ouch!" I said.

"Poor baby!" Lily said, laughing. She kissed her finger tips and placed them on my lips. I stuck my tongue out, licking her fingers seductively. "Don't get started again!" she begged and I let her fingers slip from my mouth.

"I will make you cum again!" I joked and she smiled at me, "but seriously, if you need me to leave just say the word," I said eventually. She shook her head.

"No, I am fine. I am actually planning on sleeping in tomorrow. You can stay as long as you want. I just don't know if you pay the babysitter by the hour or what. I didn't want to eat too deeply into your allowance," she explained. I shook my head.

"That's nice, thank you. But I just pay her a flat rate for the night. She doesn't have wifi in her apartment, and since I started getting my allowance I have internet now. So she takes a flat rate, and she can do whatever she wants with the internet. It works for both of us. She is actually usually asleep on the couch when I get home. I just let her sleep there and she leaves in the morning. I crash in the tub," I explained. Lily pursed her lips a little bit to the side as I spoke. A tic that I now recognized was a signal that she was thinking about something sensitive.

"So wifi," she said, "Internet is not a bad idea. What else are you spending your allowance on?" she asked. I sort of shrugged.

"Food, rent, toys for my son, my new car," I said, feeling a bit embarrassed. Early on, I had blown a lot of money on silly stuff. I had never had money before. Now I was realizing that $1,000.00 a week was a LOT of money, but it wasn't infinite money.

"Have you ever thought of spending some of that money on school?" she asked and I sort of snorted.

"School?" I asked, 'I am making more money now that I would with a degree," I said, which was true. My allowance plus my wages were plenty of money for me and for my son, if I handled it well. But Lily didn't drop it.

"For now," she said, "but you should think about the future. You won't be getting an allowance forever." I felt my stomach drop into my knees and I sat up quickly.

"What do you mean?" I asked nervously, "Are you thinking of getting rid of me?" I asked. Immediately my mind whirled, thinking through the implications of losing my allowance. I should have saved more! What could I do to convince her that I wasn't done, that there was more she could do with me? But I saw her smile and she gently put her hand on my shoulder, easing me back down into her lap.

"Don't be so worried," she said, "I don't want to get rid of you! But, I mean, you never know. Tomorrow I might show up and we have a bad quarter and the trust that owns the company tells me to beat it. Then I am going to be looking for new work and I won't be able to afford to take care of you. I don't want to lose you, Lissie, but I also can't promise I am going to take care of you forever. However much I might want to." I felt a little relieved. But, whether she had intended it or not, putting the fear of God in me had made the point. I had to think about the future. Lack of planning was how I'd gotten into this mess in the first place.

"Maybe something else, I am not smart enough for college," I said finally. And it was true. I had never done well in school. I had just barely scraped together grades in community college the first time.

"Well, that is simply not true," Lily said, stroking my hair, "You are very smart. If you were dumb, I wouldn't let you hang around here when our...date was finished to chat. I'd kick you out on your cute little ass." I laughed a little, "But you don't have to go to college. I mean, trade schools or apprenticeships are good investments of time as well. Do you like any sort of trade?" I thought for a moment, and I felt my cheeks get red.

"This is the only thing I am good at," I admitted feeling inadequate. But Lily didn't seem to notice.

"You're great at it," she laughed, "but if you don't know what you want, why not just finish your Gen. Ed. Associate's degree? Then, later, when you figure out what you want to do, you can build from there," she said.

"I..." I began to protest.

"I know you can do it Lissie, you are an amazing woman," she said, and I felt both intensely embarrassed and intensely proud at the same time. Lily was an honest person, really. To the point of being blunt sometimes. I knew she meant it. And, in kind of made me believe I could do it. I mean, she was right, wasn't she? We spent one night a week together and I was no longer intimidated by her. We spoke like, well almost like equals. And it wasn't like I was going to be getting a doctorate! It was just a few credits. And then I remembered.

"It costs like $150.00 a credit hour. After all my expenses and stuff, especially with the new car (which I really need), I would only be able to take like one class a semester," I said. I swear to God, I wasn't fishing for what came next.

"I'll pay for it," Lily said simply. As she spoke she reached over to the nightstand and grabbed a glass of water, drinking casually like she hadn't just promised to pay for my school.

"What?" I asked, sitting up again.

"You do at least 12 credit hours, no more than 15, at the community college, and I will foot the bill. Doesn't need to be all at once. You can take one class at a time and I will take care of it. As long as you keep a B average," she said. I shook my head.

"I can't accept that!" I said automatically. I mean, you can't just take money from people like that! But, as usual, Lily had no time for those kinds of financial niceties. She once told me, "I like to skip all the fake dances and get down to brass tacks." And did she ever.

"Look, you get the grades that I know you can get, I will pay the tuition. And I will pay for your babysitter when you come over too. $75 more a week. Now I am actually not just paying for school, I am paying you to go to school. I am not going to listen to any argument. Just take it," she insisted. I sat for a moment in total silence. She had almost been...rude about how she said it. And yet, it was the most generous thing anyone had ever offered me. I lay back down heavily in Lily's lap. Why was she doing this for me? Because I was good in bed? I decided it was better not to ask questions.

"Okay," I agreed and I snuggled down back into her lap and wondered how I could have ever gotten so lucky.

And then I started going to school. It took a month or two for the new semester to roll around, but I was ready. I talked to the people at my regular job, and they agreed to let me have some time during the week. I took five classes, so like 15 credit hours. An intro to psychology class and a low-level math class, some other stuff. They told me that if I took all of them, I'd have the associates degree I like six more months.

And what I was surprised by was that it wasn't as hard as I had thought it was going to be. I am not going to lie and pretend that I aced everything. Far from it. Especially in math, there were some times when I thought I wouldn't be able to get that B-average that I needed. But it was just a matter of, like, asking for help and putting in the time.

It was nothing like high school or the first time I went to college, where I could hardly pay attention in class and didn't bother doing my homework. The weird thing, back then, it didn't feel like a choice. I didn't feel like I was loafing or trying to get away with half-assing everything. I just didn't know what I was doing and sort of shut down so I wouldn't feel like a failure. You can't fail if you don't try. And this second time, I came in and I just did the work. And again, it just didn't feel like a choice. I just did I.

Some of it, I am sure now, was just that I was more mature. I had struggled. Like really struggled. And I knew what that meant now. I knew what it would mean to fail again. And I think that focused me. But more than that, it was Lily. I don't think I recognized at the time how important it was. But no one had ever believed in me before. No one thought I could accomplish anything. And I didn't think that bothered me before. But now, having someone in my corner, it made me realize how much I had been missing during the rest of my life.

I don't just mean financial support, though, obviously that was there. I gave her my bills for school and she would cut me a check the next day. But it was so much more than that. I mean, she had gone over the course options with me, she had talked me through my anxiety during the first week of school, she talked to me about my homework (though she refused to directly help on any of it). But more important than anything else, she was excited for me. Lily made it feel like I was doing something thrilling and fun. She was always so interested in everything new that was happening, and was proud of me when I did well.

I think most of it was just genuine interest in me, her desire to see me succeed. But some of it, I came to realize, was that Lily got off on dating a college girl. She would call me her "college girl" or "sorority sweetheart" when I showed up at her house. She would sort of act faux jealous asking about whether or not there were any pretty girls in my class, and I would giggle and describe myself to her.

About two weeks or so before my last set of finals, her excitement about school finally bubbled over. It was our normal date night and I had left Aiden at home with the neighbor. I was under the impression that we were going to head out to a cafe to drink coffee and listen to some bad live music.

But the instant that Lily opened the door, I knew that I was in for something different. Lily was standing in the doorway wearing one of those old-fashioned sorority cardigans. It was a sort of creamy white color with bright red trim, and some sort of red Greek letters over her left breast. The sweater wasn't buttoned in the middle, and the thin fabric was just sort of draped over Lily's large breasts. Her skin was exposed from her neck down to the hem of her white cotton panties. Other than those panties, Lily wasn't wearing anything but the sweater. Her legs looked impossibly long hanging from the bottom of that sweater. Lily's long brown hair was pulled back into long, loose pigtails and her eyes were sparkling. My breath caught in my throat. She had had never looked sexier.

But it wasn't just that. In Lily's hand was, for lack of a better word, a wooden paddle. It was maybe two feet long, the blade of the paddle maybe a foot and a half long and five inches wide. The handle was about as thick as my thumb and plastic, smoothly rounded. She lifted the paddle up and tapped it gently on the palm of her other hand. She was biting her lip.

"Well Lissie, rush is over, are you ready to pledge," she said seductively.

"I didn't know you were in a sorority!" I said, and Lily sort of rolled her eyes.

"I bought this online, you rube!" but she laughed, "They haven't worn these things in like 60 years. How old you think I am?" she asked.

"Less than 60?" I responded, in a faux-stupid voice.

"Don't I look hot?" Lily said. She didn't sound self-conscious. I'd never heard Lily self-conscious. She was just making a point.

"You're...so sexy," I said, and I was telling the truth. I didn't even feel weird about thinking that anymore. Lily was a sexy woman, admitting that said everything about Lily, not about me.

"Then stop screwing around, and play the game! Get in here, pledge," She said and she reached her paddle forward and gently swatted my hip.

"Yes...Sister?" I said, not sure of the terminology.

"Lily is fine," Lily said as I walked inside and she closed the door behind me.

"Hey, I just want to be accurate," I said as I walked past her. I felt a surprisingly sharp sting and heard a flat thump as Lily's paddle collided with my ass. I was wearing jeans, but still, it was surprising. I yelped and jumped into the air.

"There, that is authentic" Lily said giggling, but with a little tinge of excitement in her voice. I knew that sound of excitement. I was getting to know Lily better and better all the time. I knew that, most of the time, she was totally in control of everything in her life. But the one thing she couldn't control was her sexuality. And I don't mean that she was a lesbian. I mean, she was and there wasn't anything she could about that either. But I just mean the WAY she expressed her sexuality. Once she got going, she would just do whatever her body told her to do. And I think that a part of her was afraid of that. That was why she had to hired someone like me, who wouldn't talk. But as I got to know her, I sort of got the sense that she liked that lack of control too. She liked that when she was very excited that she stopped thinking. That she stopped trying to control. She just allowed the excitement to pull her along. When she was in a mood like that, she was liable to try anything. And I always liked where we ended up when Lily was in that sort of mood.

But usually, it took a little time to warm Lily up. To loosen the bonds of control. To see the essence of Lily's sexuality. I realized as Lily smacked my ass, more gently, again, that she must've been sitting around since she got home from work, just imagining this, dreaming about it. Maybe she'd put her sweater on hours ago and just dreamed of me. And now, already, she was completely ready for anything. Honestly, it was a little bit scary. But also sexy and flattering and exciting.

"Yes Ms. Lily," I said sweetly, "I will do anything to be in your sorority," I batted my eyelashes now.

"Ms. Lily, that works, I like that," Lily said smiling. "Go to the living room. And take your clothes off as you go," she ordered. But, it was sort of strange, the more she ordered, the more in control I felt. She just wanted me so bad. It felt good to be wanted.

I did as she had commanded, started walking towards her living room. But I moved slowly, easily. I let my hips tick seductively as I walk. And I slowly disrobed. I was wearing a white sweater, and I gently lifted it up over my head and tossed it aside. I reached my arms behind my back and slipped off my bra, just letting it fall in front of me. I kicked off my flats. I unbuttoned and then unzipped my jeans, feeling them grow loose around my hips. As I reached the couch, I turned and slipped my fingers into the waistband of my jeans and panties. I slipped them down quickly as I sat. And then I was I was naked in the middle of the "sorority house."

"Did I tell you to sit down?" Lily said sharply. It was her 'boss' voice and, honestly, it rattled me a bit. Maybe I didn't have that much control! I jumped up onto my feet.