The Disgraced Assistant

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.

Now I could see what was underneath. She was wearing a white thong and it was soaked. She was also wearing a white lace bra with a low shelf that barely covered her nipples. Her stomach was tight and there was a trail of blonde peach fuzz leading from her belly button down to her thong.

I didn't want to leave her on the island of exhibitionism too long. It can be lonely and scary, and it was so far away from the connection we had just been having. So I pulled her back to me. This time her tender kisses where replaced with passionate tonguing. I slid my hand down her stomach and into her thong. Her pussy was sopping wet. I could feel a trimmed layer of pubic hair pushing against my palm and my middle finger slid right into her slit. I ran my finger up, tracing the outline of her opening, and then to her throbbing clit.

This taxi was no place to get her off, but it was a good place to get a sense of how her body works. I started with a light, slow circle. The kissing was still the main deal. But it didn't take long before she broke that off and buried her head in my neck while moaning into my ear. But I'd pegged her as somebody that wanted to serve and I didn't want to do all the work.

"Show the cab driver how you like it"

Really, I meant that I wanted to see how she liked it. Theoretically, there's an optimal way to rub a woman, but in practice, I have such better luck mimicking whatever habitual masturbation pattern that a woman has developed. Emma left her head buried in my neck but turned her hips away from me so that the cab driver could theoretically see. Then with one hand she pulled her thong to the side and with the other took two fingers and started a wide, two-fingered, diagonal loop over her clit.

"Harder". By that I really meant, don't slack. I wasn't sure exactly what she needed, but I wanted to make sure she took this seriously. She did go harder. But also faster. And after awhile she started dipping her fingers into her opening.

"I need you to cum." And she did. I don't think she was comfortable enough with exhibitionism to do it loud, so she held the noise in, and the emotion came close to coming out as tears. Her eyes were watery when she looked up at me and the taxi arrived at her home.

"You're doing fine." I handed my jacket over to her so that we could walk up the stairs to her apartment in some semblance of respectability. I also handed the driver $80. That had to be at least a $60 tip.

She was young, so I wasn't surprised that she had roommates. I could hear at least one making noises in the kitchen. She led me by the hand into her bedroom, but I blocked the door so that she couldn't close it.

"Put my jacket on the dresser. Put everything on the dresser." I wasn't actually going to make her roommates uncomfortable with our shenanigans. But I wanted her to enjoy the fantasy of being caught. She took my jacket off then turned her back to me to take off her bra. At that she looked over her shoulder for approval. Then she leaned over and slid her panties down before placing those on the dresser also.

"Now put my clothes on the dresser." I gave her some help, but she managed to get my shirt, undershirt, shoes, and pants put away. I was standing there in my underwear. She motioned to the bed. Clearly she wanted me to close the door and get back to business. But I told her, "Come back here and take your time."

I was imagining those pouty lips on my balls. She'd been so gentle at the beginning of the night, and I was hoping we could get back to my original fantasy. We were still standing in the open doorway, with her roommate at the other end of the house. She ran her mouth over my bursting cock with just the cotton of my briefs between us. Then she slid my briefs down and ran a series of kisses up my thigh.

"Lick me." I spread my legs apart and moved my dick out of the way with one hand. It was clear that the only thing to lick were my balls. She started with short licks, then a series of soft kisses, and then started alternating.

"I'll do this all night." She was clearly into this service thing and I was enjoying the ball licking. Her pouty lips were driving me crazy and her wide eyes were fixated on my face.

"Bring me all the way." Clearly we could have moved to the bed, but I thought that could be for later, and that this doorway experience would be unique and memorable for her. She put one hand on my foot for balance and then brought the other one up the backside of my leg, over my hamstrings, and into the crack of my ass.

"More." This is San Francisco, so I wasn't surprised that she knew this little trick for making a guy cum super quick. But she was young and I didn't want her to feel tentative. She kept a soft lip-worshiping of my balls going while starting slow circle of my anal ring. Then she brought her hand back down between her soaking legs and shoved two fingers deep in side herself. They came back glistening. I would need a lot more lube if she was going to put those deep inside me, but I appreciated that she was about to penetrate me.

At this point she softly wrapped her lips around my entire balls, holding them still with her lips and tongue. She leaned her body up against my leg for support. Her wet fingers went back to my anus and started teasing my opening. Then she moved her other hand up to my cock and started stroking me.

Her mouth was just a soft warm radiance around my balls. Her hand was quickly bringing me to the edge and I had no reason to hold out. She had a pretty good sense of my arousal and used her finger on my anus to control me. When she was ready for me to cum, she started penetrating me with her middle finger. In and out. It was driving me crazy.

With that, I began to cum. I don't have any need for where to leave my cum. My first blast shot up and landed on her back. For my second, she'd pulled my dick down to her mouth. The rope of cum hit first on the side of her cheek and ended inside her mouth. For the rest of my cum, she held the head of my penis in her mouth and squeezed the drops down her mouth.

"I like doing good." She was happy with herself. With that she stood up and closed the door. She was clearly done playing the servant. Then she looked at me.

"Stay."