Pushing inside my boss with her dress on [MF]

This story happened about 4 years ago. I often think about it because it felt so sudden and thrilling when it happened.

I was 23 and working in a little coffee shop, trying to figure life out. I was coming off a bout of post-college depression and was kind of floating through life, hoping to figure out what it was I should be doing.

Abby was 27 and my boss. She was a really cool person: a music PhD student, she sang opera and taught voice lessons on the side. She worked in this coffee shop because it was easy and gave her time to do schoolwork. There were hours when the shop would be empty and we would talk about all sorts of things; we had similar worldviews but I learned a lot from her and loved talking to her.

I also found her really attractive, a distinct perk when I was interviewing for the job. She had dark hair and enormous, almond-shaped eyes that got wider when she spoke about music. She had the body of a college swimmer, although a few years of intense grad school in between softened her curves. She had big, pillowy breasts that I would steal glances at when she was teaching me about the cappuccino machine or ringing up a customer.

She also, unfortunately, had a boyfriend. Not that I was ever particularly serious about my chances with her; at that point I had never been with a woman older than me and 4 years felt formidable. I was also rather invested in being a good employee, i think to prove to myself that i could do _something_ in the real world.

So months went by and we became good friends. We'd talk during work, share laughs about customers and invent little games to pass the time. One morning, her big, beautiful eyes were puffy and she was clearly upset. She told me that she had broken up with her boyfriend. They'd been together 4 years, and she realized she didn't see herself marrying him. I awkwardly consoled her, and felt genuinely bad, though not without a flicker of excitement.

Things continued on as normal for a week or two, until one Friday Abby mentioned that she needed a drink. The coffee shop was in an area with lots of little bars, and she suggested that we go get sangria after we closed up at 4pm. This would be the first time we'd hung out outside of work, and I wasn't sure her intentions but I quickly agreed. We strolled to a mexican restaurant, one of those new ones that sell fancy cocktails and charge you for salsa, and ordered a pitcher of sangria and some guac.

She was a great conversationalist when we were at work, and the sunshine and the alcohol just livened things up. We talked and laughed and our conversation got more flirtatious than it ever had. She asked me about my dating life, and I blushed while telling her about my misadventures on dating apps. She told me I'd have to teach her, she'd been out of the game so long and Tinder didn't even exist the last time she was single! I smiled and promised to impart whatever wisdom I had accumulated.

Around 7pm, we left the restaurant and went for a walk. The neighborhood was really beautiful and we strolled around enjoying the warmth and the liveliness around us. She knew I lived nearby, and she suggested we go to my apartment for a beer. At this point, I was getting more confident and excited that something could happen. We kept brushing up against each other walking and there was a spark between us that neither of us had acknowledged before. We got to my apartment, and my roommate was in the living room, a welcome development that led us into my room.

We sat on my bed, drank a beer and I suggested we watch Arrested Development, a show we both liked. We laid down and she put her head on my shoulder, and we giggled trying to get the laptop situated so we could both see (if this isn't the hallmark of youthful hookups, I don't know what is).

We watched about 45 seconds of the show before we kissed. It was slow and warm and really quite tender; I felt a wave of caution come over me as I kissed her as I remembered just how recently she'd gotten out of a serious relationship. She looked at me with those big eyes and smiled and told me she wasn't sure what she wanted right now and she just needed a distraction and time to process everything. I told her I understood and we went back to cuddling and watching the show.

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