Inside My Boss
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.
This lasted another 3 or 4 minutes before we started making out again, more urgently this time. She was wearing a dress, I don’t remember the color but I remember it hugged her body and I could feel her warmth as I ran my hands over her. We rolled around on my twin bed, exploring each other’s mouths. I remember she gasped a little when I kissed her neck, as if she hadn’t had that feeling in years, and I found it incredibly sexy.
As turned on as I was, I was careful not to push things too fast. It was still fresh in my mind that she wasn’t sure what she needed and I wanted to be sensitive to that. So I figured I’d let her guide things where she wanted them to go. She took my shirt off while I was on top of her, and I flipped us over so I was on my back and she was straddling me. She started kissing my chest and down my stomach, and unbuttoned my jeans. I looked down and saw her big eyes staring up at me and pulled her back up to kiss me. I took off my jeans so that I was in boxers and she in her dress.
To briefly describe what I look like, I’m 5’10” with dark hair and a soccer player who also likes drinking beer’s body. I usually have a few days’ stubble and women sometimes tell me I’m “cute.” I have what I believe to be a perfectly average penis.
So anyway, I’m in my boxers on top of my newly single boss, and my perfectly average penis is at this point rock hard, covered in pre-cum and grinding against Abby’s dress. We were both really consumed with each other at this point, but I was still wary to undress her as I didn’t want to take advantage of her somewhat fragile emotional situation. We kept kissing and rubbing against each other and Abby shifted so that I was between her legs, and her dress ran up so that I could see a black thong. This turned me on even more and I was rubbing my cock firmly against her clit, through the thin layers of fabric made up by my boxers and her thong. I put both my hands on her ass and pulled her into me, pushing my tongue into her mouth. This probably lasted a minute but felt like hours.
I was pushing up against her when I felt my cock catch underneath her, instead of rubbing against her clit. She wrapped her legs around me.
The next moment was the single sexiest thing that’s ever happened to me. My penis had worked its way out of my boxers and was pushing right against her opening, through her thong. With her legs wrapped around me, Abby pulled me into her and my cock slid right past her thong. Immediately I could feel the warm and wetness of her pussy. We both gasped and looked at each other. Her huge eyes were round in excitement and shock. She let out a huge moan and pulled me in deeper until I was filling her up. She was so tight, and I had only had condomless sex once or twice so the sensation was incredible
I was so turned on I couldn’t think, and fucked her just like that, with both our underwear still on and she in her dress, harder and harder. She dug her nails into my back and we kissed so deeply it felt like we were completely connected. It can’t have been much more than 2 or 3 minutes when I felt myself about to cum. I told her, and Abby said in a voice that barely sounded like her, it was so distorted with arousal: “Fuck yes, cum inside me.” I grabbed her ass and emptied myself into her, my cock pulsing in the most intense orgasm I can remember. She wrapped her legs tighter around me and I could feel her pussy tense up as I came.
We shared a stunned, surreal afterglow and talked about what had happened. We ended up having sex 5 or 6 more times before she finished grad school and moved, and had a lot of fun together. I still think about that first moment I pushed inside of her and it immediately turns me on, years later.