Emma used to be an executive assistant for my boss. She's young, blonde, and perky in that way that young women are perky. She has sharp B-cups and almost always wore blouses that made you want to reach in and cop a feel. I know better than to mess with my boss's assistant. I just wanted to be friendly enough that she made sure my emails and meeting requests got through.
She seemed eager to please and seemed to be doing great work. Then one day Emma was gone and a new assistant was in her place. Two weeks later I got an email from her asking if I wanted to grab coffee. I really wasn't thinking anything of it other than that I had a full week and that it would be hard to make the time with my day schedule. So rather than accept the coffee, I asked if she had time to meet me for drinks after I got off work (usually after 8pm). After some back and forth, we settled on The View at the top of the Marriott because she seemed to want to avoid running into former coworkers.
I got there first and she found me at my table. The weather had just turned warm and she found me at my table wearing brown boots and a white, linen sun dress that went down to just above her knees. The dress was transparent enough that you could really get a sense for all the taught pink flesh radiating underneath it. At work, she'd been pretty liberal about showing cleavage and I'd spent a lot of time wondering what it would be like to wrap my lips around her nipples. But today, with the dress and the bare legs, the first thought into my head was what it would be like to work my mouth up her inner thigh.
I bought her a martini and worked on a tonic water for myself (see bio below, I've got many vices, but drinking isn't one). We made a little bit of small talk and before we'd even gotten to why she'd asked to meet, she'd downed her martini. I'd been assuming that she wanted to ask me for help finding another job, but she seemed visibly nervous. So I ordered another drink and settled back to let her gather the courage to tell me whatever she wanted to tell me.
I liked watching her drink from her second martini. She had pouty lips and after every sip, she'd give her lips a quick lick which left them glistening. All I could think about at this point was what those lips would feel like wrapped around my cock. She took enough time with this second drink that my mind got to wandering about where else I'd like her lips. One of the things I love is a woman who can give soft kisses and light sucking to my balls. I was imagining that she might be such a woman when she finally asked a question.
"How are things at the office?"
"They're fine. Everyone's heads down for deadlines."
"Right. Just like old times." She paused. "What have you heard about me?"
It finally clicked that she was nervous about something related to her departure. I thought my boss had just felt like a change and replaced her. But now I thought that maybe she'd gotten fired and that it was for a reason other than sloppy work. "Just that people miss you."
That was a lie. Honestly, I hadn't heard even that much. The office is pretty heads down all the time, and nobody paid any attention to her leaving. Clearly she'd disgraced herself to the point where she thought people would be gossiping about her. But even now, with a chance to find out what had happened, I could only think about whether this night could head toward a make out session.
Thankfully she dropped the subject and seemed to relax. She asked if I had time to hang out while she had a third drink.
We got up from our table and moved over to a seating that was closer to the window. The View does have great views of the city, and even as a local, I enjoy sitting next to the window. The change of location gave me two opportunities. One, I got to see her from the backside. At the point I was wondering what sort of panties she had on and I could tell from my peak that it was a thong or nothing. Two, I put my hand on her back as we walked to the table, which led to us sitting pretty close, with a lot of patting and light touching as we got back into small conversation.
It was only a minute later when her eyes locked onto my lips and I took that as a cue to lean in for a kiss. Her pouty lips were delicate and soft. She gave tender kisses to all parts of my lips and would lean in to hug me and give a little bit to my ear lobe. My hand went right to her thigh and slid up her inner thigh. I was half way up her thigh when the heat radiating off of her mound hit. I still couldn't tell if she was covered up, but I knew she was into it the night.
