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.