New Assistant

I had no intention to force my wife to do anything she did not want, I loved her and I respected her desires, so I did my best to contain any resentment that might have built up due to it. Sometimes it was not easy.

"I'm really sorry," she said. "It was a really fun night and I am very proud of you."

"Thank you," I said and kissed her on her forehead. "I'm going to go read for a bit downstairs. I'm not quite ready for sleep."

I left her there and went down to my home office. I had a bottle of bourbon there and poured myself a few fingers and opened up my personal laptop.

It wasn't long before I was cruising through a porn site. It seemed like I spent many nights like this, frustrated and horny, needing to jerk off to get some relief.

I thought for a moment and then typed in *freckled girl* into the search bar of my favourite site. I began scrolling through the videos looking for one that looked like Tara. It was dumb, I knew, and creepy, but I couldn't help myself.

I stopped at one where the actress looked a little bit like Tara. The girl on the screen had more freckles and her body was a bit different, but I thought it would do. I fished my cock out of my pyjamas and began to stroke, watching the pornstar take a thick rod in her throat.

My own cock filled my hand, about seven and a half inches long, pretty thick, uncut, with heavy veins running along the top of it. Pre-cum had formed on the tip so the foreskin slid back and forth easily.

After a few moments I sighed. This wasn't doing much for me. Sometimes the fakeness of porn couldn't get me off. I closed my eyes and tried to imagine my young assistant, trying to guess what she looked like without her professional clothing.

I picked up my phone, moving to the directory. Sometimes the company had employees add photos of themselves to their account. I knew that when I called people my bearded face showed up on their screen. Maybe Tara had a photo attached to hers.

I was disappointed when I found that she did not and went to flick away from that screen. In my defence, I was using my left hand, the right being wrapped around my cock, but instead of swiping away Tara's contact I accidentally hit the call button.

My eyes went wide and I was about to hit the red 'end call' button, but I heard Tara's voice on the phone, saying hello. I quickly put the phone up to my ear.

"Shit," I said. "Sorry, Tara! I didn't mean to call you this late." I glanced at the clock on my wall and saw that it was shortly after 1AM. I tried to think of a good excuse for why I would even accidentally call her so late.

"I was just updating my contacts on my phone and must have accidentally hit the call button. I'm sorry again."

"That's ok, sir," Tara said. "I don't mind. You can call me any time you need to. For any reason. I'm here to make your life as easy as possible." I inwardly groaned. How was her voice so sexy? I realised that I was still gripping my cock and could not help but to stroke myself.

"I appreciate that, Tara," I said. "But it's really not necessary. It was honestly a mistake calling you. An accident. I'll let you get some sleep and see you tomorrow."

"Of course sir," Tara said. "Oh, since I have you on the phone could I ask you something?"

"Oh," I said. "Sure."

"Great," she said. "Actually it's probably better if I give you a video call. If that's ok with you?"

"What," I asked but Tara had already hung up on me. I was looking at my phone, confused when it vibrated. I was glad that I did not have the ringer on. My wife slept deeply, and sound did not carry well in the house, but still. She would wonder who was calling after 1AM.

Out of instinct I accepted the call, belatedly realising that my pants were around my hips and my cock was out. My eyes widened but realised that Tara could only really see my face and wall behind me. I sighed with relief.

That was when I took in the woman on my phone. Tara was still wearing her glasses but she was no longer wearing her professional outfit. The way her phone was angled I could see that she was wearing a silky top with thin straps over her shoulders. Her auburn hair was no longer done up in a bun, but fell around those bare shoulders. I could see that her freckles cascaded across those as well.

After thinking about them all day, I was finally able to see just how big her breasts were. They were free under the top, and while they were large and heavy, they did not seem to sag. Her nipples pushed out against the fabric, the nubs forming tents.

I swallowed and my cock throbbed in my hand. I gave it a squeeze but did not risk stroking it, in case she could see the movement.

"Maybe we can talk about this tomorrow," I said, realising that this was not an acceptable situation.

"No," she said, smiling at me, showing me her dimples again. "This can only be now."

"Ok," I said, trying to keep my eyes on her face on my phone. "What can I do for you?"

"Well, sir," she said, and seemed to be walking through her apartment. "I'm trying to decide what to wear tomorrow. I like to prepare my outfit the night before. Will you please tell me which outfit to wear?"

I shook my head, surprised. I didn't really understand what she was asking of me.

"Your outfit?" I asked. "I don't... I'm sure whatever you choose is fine."

"You see, sir," Tara continued as if I had not spoken. "When I have a boyfriend I like when he decides what I should wear. And I don't have a boyfriend at the moment so I think it would be a good idea for you to decide."

My cock in my hand twitched. There was something so intimate about this situation. The way my body reacted told me that this was not a good idea.

"I'm not sure that's appropriate," I said. "Let's just meet up tomorrow and, again, I'm sorry I called and interrupted your evening."

"Here are the options, sir," She said, continuing to ignore my protest. She reversed the camera and panned it over a neatly made bed. Her bed. There were three outfits laid out on it, as if on display.

"I don't think this is necessary," I said. "I think I'll let you go now."

"Sir," Tara said, reversing the camera to her face again. She was biting her lip. She looked vulnerable and oh so sexy. "You don't understand. I can be a bit OCD and I have trouble with decisions like this. You would be doing me a huge favour. Just tell me which one you would like me to wear and I will wear it tomorrow."

I sighed. Ok. That kind of made sense. It was probably a breach of some HR thing but she did sound like she needed some help.

"Ok," I said. "Show me again and I'll let you know."

"Thank you so much!"

She slowly panned the camera across the bed once more. This time I had time to view each of the outfits. I considered each of them in turn. I could not help but imagine what her body would look like in each one.

The first was a short sleeve black top with a white collar. It was paired with dark grey slacks with a high waist. The second was a white button up blouse. The neckline seemed to be in a modest 'V' shape. It was paired with a red, textured skirt. The third was a silky camisole paired with a different pair of black pants. The top might not be 100% suited for an office but she had a black blazer sitting beside it, presumably to wear over it, making it more demure.

I was a bit at a loss. I was not exactly sure what the correct path here was. I really wanted to see her in the camisole. It would give me a chance to check her out all day. I shook my head. That was the wrong path. I needed to avoid temptation.

"I guess the white blouse and skirt will be fine." I said finally, choosing almost at random.

"Thank you, sir," Tara said. "I'll wear that outfit just for you. Now," She continued and swung the camera to a bench she had at the end of her bed. "Which bra and panties set should I wear under them?"

I could see on my phone that she had three sets of matching underwear laid out on display. The first one was lacy and black. The cups of the bra were a mix of lace and sheer fabric, and the panties were made of the same material and cut high on the hips. The second set was cream colored, with the cups of the bra cut very low, with the panties a simple thong. The third set was red, the bra simple but the panties were also a thong.

I couldn't help but pump my cock a few times looking at them.

"Ah," I said, finally, "This.. this is inappropriate now. I'll let you go, Tara."

The camera reversed to look at her again. She was holding her phone out at arms length, giving a view of her chest up. I almost groaned with lust seeing her breasts once more, the nipples clearly hard.

"Sir," she said. "Stop. You know some people might say calling your assistant at one in the morning is inappropriate. But I answered. I don't find it inappropriate at all. I like it. I like that you were thinking about me. I like that you called. And I want you to decide what underwear I wear at work tomorrow. Unless.."

She paused and I saw her free hand come into the frame, and unconsciously licked my lips as her fingers gripped her breast, squeezing it slightly, lifting it, as if she was presenting it.

"Unless," she continued, "you don't want me to wear any tomorrow. They are pretty big to not wear a bra, don't you think?"

I could not think, let alone answer her question. I was stroking myself now, not being careful to hide the movement of my arm.

"I mean, with that blouse you chose," she said, her fingers finding her nipple and squeezing, "my nipples will be on display for anyone to see. Maybe that's what you want? Do you want me to put myself on display? If you don't decide on which ones for me to wear, I'm going to have to assume you don't want me to wear any. And I'll do whatever you want. I'll show up tomorrow in that blouse and skirt with no bra and no panties."

Her hand moved to her other breast, playing with that nipple.

"Is that what you are telling me to do?"

This had all gone too far, I suddenly realised. This was my employee. My wife was just upstairs.

"No," I blurted. "That's not.. I mean.. the black ones. Those."

Tara smiled at me.

"Ok, sir," she said. "Thank you for your help. Is there anything else I can do for you tonight?"

"No," I said, transfixed on my phone, jerking my cock. "I don't.. I can't.."

"Ok, sir," she said. "I'll see you tomorrow."

She hung up and the screen went black.

I leaned my head back and jerked furiously, grabbing a tissue off of my desk and spurting a heavy spray of cum into it, groaning.

I caught my breath and horror came over me. What had I just done? It was madness. I tucked myself away and went up and crawled, wracked with guilt, into my bed beside my sleeping wife.

+++++

I did not sleep well. I lay in bed for hours, staring at my ceiling, trying to figure out the proper course of action. There was no way I could work with Tara now.

Looking back over the conversation I realised that I was not the only one to blame. She had been goading me on all along.

That being said, I should have stopped. I should have hung up, setting clear boundaries with my assistant. Not jerked my cock like a 14 year old while she teased me.

I thought about transferring her. I knew Mandy from HR would do it if I asked, but she would need a reason, and I could not think of a good one to give her. Tara had performed wonderfully as an assistant the first day. There was nothing she did that would warrant a transfer.

And, if I was being honest with myself, did I want to transfer her? She was beautiful and nice to be around. My ego was definitely getting a boost from her attention. And she was good at her job. There was no guarantee that her replacement would be as good.

I decided, laying there in the bed with the wife I felt like I had betrayed, that I would just have to have a conversation with her the next day. Let her know that I was flattered, but we had best keep things more professional.

I finally fell asleep, but all too soon my alarm was going off and I had to get ready for work.

Janice was already up and had made coffee by the time I had a shower and went down. She was feeling ok, despite having drank a bit too much the evening before, and kissed me on the cheek on her way out the door.

I finished my coffee, ate a piece of toast and headed into work.

Tara was sitting at her small desk outside of my office when I arrived.

"Good morning, sir," she said, smiling at me when I walked up. "Did you have a good night?"

I took a moment to glance her up and down. She was wearing what I had chosen, the white blouse and black skirt. She had missed one of the top buttons, it seemed, and I couldn't help but glance down into her cleavage, remembering what she had looked like the night before, fondling her own breasts.

"Good morning, Tara," I said, determined to keep things professional. "I had a good night. How about you."

"Oh," she said, still smiling, dimples on display. "It was a very good night. I had a surprise phone call that really made me happy."

I coughed and felt my cheeks flush with embarrassment. I could feel my cock begin to swell.

"Right," I said. "I'm going to get to work."

I walked past her quickly through the door of my office and closed it behind me. I took a deep breath and hung my overcoat over the coat rack and sat behind my desk.

I knew I had to resolve this thing with Tara but still wasn't quite sure how to broach the subject. Later, I decided. Maybe after lunch.

I opened the app that contained my schedule for the day, looking for a good time for a conversation with Tara, and glanced over it.

I frowned. This was new. There was a fifteen minute block in my schedule first thing that read 'inspection'. I had no idea what that was. It had not been there yesterday.

I scrolled through the week and the next and saw that it was the same every morning between 8:30 AM and 8:45.

I pressed the buzzer on my desk and called Tara into my office.

She stepped in and closed the door behind her. I noticed that she locked it, turning the deadbolt latch as well. I frowned. What the hell?

"Tara," I said, gesturing to my laptop in front of me. "What's this? 'Inspection'? It's on every day? Did we talk about that yesterday?"

"No, sir," Tara said and took a step into the room, now halfway between the door and my desk. "I added it this morning. Now that you are choosing what I wear, I thought that you had better get a chance to make sure I was doing as you said. It's all about accountability, isn't it?"

"Right," I said slowly, not liking where this was going. It looked like we were going to have to have our conversation first thing. "About that. I mean to tell you that.."

"If you don't hold me accountable," she interrupted me, "I might slip up. It's good for me."

She began to slowly turn in a circle in front of me. I could not help but watch. The blouse looked good on her, and hugged her body nicely. While her sweater the day before had hidden her form it was very clear here. She had a large bust, but her waist was small. Her hips were wide and her ass, I saw as she faced away from me, was round and heart shaped. She was wearing four inch heels today, which brought her to a couple inches below my 5'10, and they were doing their job, making her stand in a way that showed off her rear.

I could not help it. I was getting hard under my desk. I did not dare reach down and grip myself but I was sorely tempted.

"Yes," I said, unsure how to properly respond. "I see. You wore the outfit. Very.. good? Still I think that's enough. Let's get to work and we can discuss this later."

She completed her turn as I spoke and her hands went to the buttons of her blouse. My eyes widened as she undid the top one then the second.

"Wait," I said. "What are you doing! That's not.. there's no need.."

"The blouse and skirt aren't the only things that need to be inspected, sir," she said, completing the unbuttoning, her shirt hanging open, allowing me to see the inner curves of her breasts and the middle of her bra.

"You were very clear which bra and panties I was to wear today," she interrupted me again. "You need to complete your inspection."

She unclasped the skirt, the fastener at her left hip, and it fell to the floor at her feet. She shrugged out of her top and it fell to join the skirt. She was now standing only wearing her bra panties and heels.

The bra was incredibly sexy. There was lace on the undersides, but the cup was sheer, her nipples visible through the fabric. Her panties were a similar design, with the lace around the waist and leg holes, but sheer otherwise. They cut high on her hips, half of each ass cheek on display.

Through the fabric I could see the slit of her pussy, shaved or waxed clean, puffy and enticing.

Slowly, once more she turned in front of me, and I could do nothing but sit there, hard as a rock and admire her.

"Do I pass inspection, sir," Tara asked, facing me once more.

I cleared my throat.

"Yes," I said, my voice almost cracking.

"Good," she said. "I'm so happy you approve."

She quickly pulled up her skirt and replaced the blouse before I could clear my head. She went towards the door and stopped looking back at me.

"I'm really looking forward to working with you, sir," she said. "We have some meetings in about twenty minutes. If there is anything you need to take care of."

She glanced down at my desk, presumably knowing that I was hard under it for her.

Then she left.

I couldn't help myself. I grabbed a tissue and jerked off, dropping the soiled paper into the wastebasket beside me. I leaned back in the chair, my cock deflating and groaned. I was in big trouble.

++++

It was a busy day and I never did get a chance to have a talk with Tara about lines that we should not cross. I had one meeting after another. Each time Tara would sit on the couch in my office taking minutes. I could hear the soft sound of her keyboard as her fingers flew across it, recording all of the pertinent information.

Her work was flawless. After each meeting she would email me the minutes, with action items listed on the top in a clear format. She was, regardless of anything else, incredible at her job.

I couldn't help, however, looking over at her in the meetings, imagining the bra and panties she was wearing under her clothing. I wanted to cross the room, ignoring whoever was in it meeting with me and tear her clothing off and fuck her on that couch. It was a bit distracting.

I ate lunch alone that day, heading out of the office, needing some space from her. She seemed to be a bit disappointed to learn that we weren't going to be eating together but she hid it well.

It was shortly after six when I shrugged on my overcoat and went to head home. Tara was still at her desk, working.

"I'm off," I said as I passed her desk. "Are you staying late?"

"Just finishing up some stuff, sir." She said, looking up at me through her black framed glasses. "I'll be leaving soon too."

"Ok," I said. "Well. I'll see you tomorrow."

"Later," she said, looking back at her screen and typing.

"What," I asked. "Later?"

"Later," she said, nodding, still working. "When you call me to approve my outfit for tomorrow."

I stopped and sighed.

"I'm not calling you," I said. "That.. I am very sorry about that. I shouldn't have called and I should have never let it get so far. I won't be calling. I'm sorry if you feel like I led you on."

She looked up at me again.

"Sir," she said. "You have to call. Or I will show up tomorrow naked. I will not be wearing anything under my jacket. Do you want that to happen?"

"What," I said, scoffing. "You won't do that."

"Yes," she said and her voice was very serious. "I will. If you do not tell me what to wear I will assume you want me to wear nothing."