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.
We made out in that surreptitious, public bar way. You keep your eyes on each other so that you don't make eye contact with the other people in the bar, while your hands make quick gropes, desperately wanting access to every part of the body, but afraid to be too blatant in public. Eventually, she leaned in and whispered, "I'll do anything you need."
That was enough for me. I dropped some money on the table and led her out of the hotel and into a taxi. We made out all the way down the elevator and had our hands all over each other as we crossed the lobby to the taxis. The public make out session had each of us charged up and we didn't want to lose contact with each other.
We tumbled into a taxi, with me sprawled across the entire backseat and her straddling one of my legs straining to get her lips back in contact with mine. The heat from her pussy was now sitting on my thigh and I could feel that she was wearing a satin thong and that it was soaked. I mumbled "Your place." and she called out her address for the driver. Then she leaned toward me, put two hands on my chest, put her face right in front of mine, and said, "Tell me what you need."
Now, there's two things that really turn me on. One is playing with a power dynamic. I don't want to be dealing with a gimp outfit, but I do enjoy a strong woman who is dominating me or a enthusiastic woman who's dying to serve. Emma was giving me that service vibe and I was getting ready to start giving her orders. The other thing, is exhibitionism. I especially like to watch a woman get watched. So I told the driver to take his time and that there was a big tip at the end. In my experience, cabbies are even keeled and game for anything as long as it doesn't cause them hassle. Then I turned back to Emma.
"Give me your dress."
She gave me a look. I think she was thinking that she was going to give me a blow job. Actually being naked, or mostly naked in the back of this cab, hadn't crossed her mind.
"Now." I was confident. She was probably thinking forward to whether I was going to make her get out of the cab naked. That fear was part of the fun. Of course, I planned to just pocket the dress and give her my coat when we left the cab. She slunk down in her seat a bit and started lifting the dress up while looking me in the eye to see if I was going to stop her. She slunk down even further when it came time to get the dress over her head.
