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I (33M) have been working with my boss (32F) on and off for a few years now, and I’ve gotten to know her relatively well in that time. Initially I wasn’t attracted to her, but as the working relationship developed, I started to have a bit of a thing for her. She’s petite and brunette, with small boobs and a tight ass, quite tanned and generally toned.

Over the last six months or so, we’ve been texting more outside work, just sharing jokes and links, and having more non-work related conversations. There have been a few occasions where I’m certain she’s caught me checking her out as she walks past, and there have been some a accidental leg or arm touches when working in close proximity.

Last week, we had a meeting at a different office and for handiness, decided to carshare on the way back to our own office. We walked back to the car, which was in a multi-storey car park, but I realised when we reached it that I needed to pay for parking at the machine at the entrance, so gave her the keys and told her I’d be back in a couple of minutes. She was wearing her standard work attire – black pumps, tights, a knee-length skirt and a light cardigan.

I got back to the car a couple of minutes later and got in, reaching across the passenger seat to put my wallet and the parking receipt in the glove box. As I leaned over her I inadvertently brushed my hand across her thigh after closing the glove box.

I didn’t even have the ‘Sorry’ out of my mouth before I felt her hand on mine, pressing it to her leg. I looked up, slightly confused, and all she said was ‘It’s okay’, before starting to slowly move my hand up under her skirt.

My confusion was quickly replaced by excitement, and I followed her lead, running my hand up her leg as she moved the seat back to give us more space. I was shocked and surprised to figure out that what I wondered were tights were in fact stockings, and as I reached the top of them, I felt her soft and smooth skin, then the unmistakable feel of lace underwear.

She had unbuttoned her cardigan by now, and was slowly rubbing her small boobs through a white lace bra, and I could see that she had puffy dark brown nipples. I started to rub her pussy through her underwear, surprised to find that she was already quite wet; maybe she’d started while I was downstairs paying.

As I progressed in doing this, I pulled the underwear apart and felt her trimmed bush and wet pussy, using her wetness to help me slide first one, then two fingers inside her. She was wet and warm and pleasantly tight, and after 4 or 5 minutes of me fingering her, while my thumb teased her clit, I heard her moans change in intensity and felt her pussy tighten round my fingers.

When she came, she was roughly tweaking her nipples, and I felt an extra burst of wetness on my hand. We stayed in that position for 30 seconds or so, before I slowly withdrew my hand from under her skirt, leaving a trail of her cum along her inner thigh and the top of her stockings. She looked at me, her face relaxed, and said ‘Taste it’, so I obliged and licked her cum off my hand. She smiled at that, a satisfied smile that showed she knew she was in control of the situation.

At this stage my cock was straining against my trousers, and she leaned over, placed her hand on it and said ‘Maybe some other time, we better go now’. I was simultaneously frustrated and thrilled, but obliged and drove back to the office. It was unbelievably exciting sitting there surrounded by people for the rest of the day knowing what we had done.

No further mention of it has been made, but I’m hopeful that something more might happen in the future.

NSFW: yes

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