New Assistant

"You'll get fired." I warned her.

"Probably," she said. She leaned back from her computer and looked up at me. "I don't think you understand, sir. I'm 100 percent yours. I will do whatever you tell me. If there are consequences to that, well, that is what it is. But that also makes those consequences your responsibility. Do you want me to get fired? If so, don't call me tonight. It's up to you."

She went back to work. I shook my head. I had no idea what to say. I turned and left the building.

+++++

Of course I called her.

I tried to resist. I sat there in my home office, wife upstairs asleep, spinning my phone on the top of my desk, sipping bourbon for a couple hours.

I vacillated between calling Tara, following this thing between us as far as I could take it, and calling her bluff. There was no way that she would follow through with showing up naked.

I was feeling manipulated and trapped. I had already let things get too far, and was very worried that I was not in control and they would get worse. Part of me, if I was being honest with myself, wanted them to get worse. After several years of my wife's growing disinterest, I was excited to have someone who seemed to be interested in me.

I looked at the clock. It was almost 2 AM. I wondered if I had waited too long. I snatched up my phone and found Tara in my contacts and video called her.

She answered immediately.

"Hello, sir," she said. "I was starting to doubt you were going to call."

She seemed to be laying down, her auburn hair spread out around her. She was wearing her glasses, and smiling at the camera.

"I almost didn't," I said. "I'm not sure I like where this is all going."

She raised her eyebrows.

"Where it's going? Where what is going? You are just helping me make some decisions." She said, smiling slyly. "Or is there something else you would like? I already told you I would do anything for you."

I sighed. Just seeing her face, hearing her voice teasing me already had me hard.

"I don't know what to say to that," I said. "I'm a happily married man. You and I should not even be having this conversation."

"I'm glad that you are happy," Tara said. "I really am. And I don't want to change that at all. I just want you to be as successful and happy as you can be. Trust me. I can help you with your job. I am very good at what I do."

"I don't doubt that at all," I said, truthfully. "It's just the rest of it. The outfits, the.. inspection.. I don't think.."

"The outfits? You want to decide now? I thought you might want to chat a bit. But ok," she said, speaking over me. "Here they are."

She sat up and the camera moved further from her face allowing me to see more of her. She was wearing what looked like some kind of lingerie. Her large breasts were barely contained in lacy, sheer cups. I almost groaned and reached down, gripping my cock through my pyjama pants.

The three outfits were on the bed again. The same camisole as the evening before was there as well as two combinations of shirts and pants. I knew Tara would look great in anything.

"Which one sir," she asked me from off camera.

I took a breath, diving in despite myself.

"The camisole." I said. I really wanted to see her in it.

"And," she said, moving the camera to three sets of bras and panties. I chose a pink set, thinking that I would like to see them on her in the morning for her 'inspection.' The bra cups cut very low, and I was curious to see what her breasts would look like in it. My hand fondled myself while I made my decision.

"Can I ask you something, sir," she said, turning the camera back on herself after I chose.

"I guess so," I said.

"You love your wife. I get that," she said. "But did she fuck you tonight?"

I coughed, and considered hanging up. Instead I decided to be honest.

"No," I said. "She did not."

"And yesterday?" She asked.

"No."

"Last week?"

"No," I said again. I saw Tara frown.

"When was the last time, sir, if you don't mind me asking?"

I sighed.

"It's been three months," I said. I felt some shame for some reason. It was a tough thing to admit.

"I see," she said. Then she nodded. "Ok. That's good to know."

"Why," I asked. "Why is that good to know?"

"Oh," she said, shrugging. "I just need to know as much as I can about you in order to serve you best. Anyway, is there anything else I can do for you tonight? Or did you want to get to bed? It's pretty late."

I sighed.

"I should get some sleep," I said. "You too."

"Yes sir," she said. "I'll see you in the morning for my inspection."

I hung up and jerked off before going back up to bed.

+++++

The next morning was a repeat of the day before. Tara came into my office and did a slow turn to show me that she was wearing the outfit I chose.

The camisole was maybe a bit risqué for the office. It hung to her large breasts and was loose in the neck. I knew that if she leaned forward I would get a view down her top at her freckled breasts. The blazer she wore buttoned up covered it, however, making it more workplace appropriate. The pants hugged her hips and ass nicely showing off her figure.

Once she completed her turn she stripped off her outer clothing and was clad only in her pink bra and panties. The cups of the bra cut down so that the tops of her areolas were above the fabric. I could see her nipples hard under the bra. When she turned I could see a damp spot on her panties. Obviously showing herself off to me was exciting for Tara. So she was standing there wet while I sat there with a hard cock.

Like the day before, she gathered her clothing and re-dressed and went to work while I tried to calm myself back down.

It was not easy to get rid of my erection. When I was in a meeting with someone else Tara wore her blazer, but when it was just me and her she removed it. Every time she leaned forward, which she seemed to do quite often, I would look down her top and enjoy the view.

Finally lunch came and I was about to leave once more to get away from my assistant and get some fresh air when Tara came into the office followed by a young woman carrying a folding table.

The woman had dark hair and light brown skin. Her face was pretty, even with very little makeup on. Her ethnicity was hard to place, but I was assuming latin american. She was quite lovely. She was wearing a white outfit that reminded me a bit of nurse's scrubs, except that the top buttoned up. It hid her body pretty well but I could sense that it was small but nicely shaped.

"What's this," I asked Tara.

"I think you've been stressed so I booked you a massage for your lunch break," Tara said, pulling chairs to the side, making room for the woman to set up.

"Ah," I said. "That's fine. Thanks. I'm fine. I don't think.."

"Most executives have a massage at least once a week, sir," she said, looking at me. "It's covered by your insurance."

"Really," I asked, surprised. "I didn't know that."

"Yes sir," she gestured towards the woman. "This is Esma. She has very good reviews. Just strip down and get under the sheets."

I looked between the women, and shrugged. I had been tense since starting this job, not only because of Tara and my attraction to her, but from the stress of it all. A massage would be nice.

"I guess that sounds pretty good, do you guys mind stepping out so I can get ready?"

"Of course, sir," Tara said, heading for the door. "And Esme won't look."

The masseuse turned away from me, laying out her oils and towels. Once I heard the door latch behind Tara I began to strip, setting my suit aside. I climbed naked under the sheet on the table, laying face down.

Esme got to work. She had strong hands for a small woman and silently worked at the knots I had not even noticed had formed in my back and shoulders. She worked her way down my glutes, thighs, and calves.

My eyes were closed, enjoying the woman's expert ministrations. I have to admit, it was nice to have someone else's hands on me, and I predictably reacted. My cock was half hard by the time she was done with the soles of my feet.

"Roll over, please," the woman said. Her voice was lightly accented, but I could still not place what country her origin might be.

"Oh," I said, slightly embarrassed. "That's ok. We are probably almost out of time."

"I've been paid for the full service, sir," she said. "Please roll over so I can complete the job."

I hesitated another moment then rolled over under the sheets. This was a very good massage and I was not really in a rush to finish. I closed my eyes and sighed contentedly when she began to massage my shoulders and chest.

I almost did not register her hands moving lower, but my eyes flew open as she pushed the sheet aside and gripped my cock in her small hand.

"Whoa there," I said, starting to sit up. "You don't have to.."

She pushed me back down with a hand on my chest.

"The full service, sir," she said and began to stroke me. My hard cock filled her small hand. With her free one, she began to unbutton her top, pulling it open. She had nice breasts. Small, but firm, with thick, dark nipples.

"Just relax. Let me take care of you," she said, pumping my cock with expertise. "Just don't touch me. That's not part of it."

I should have ended it. I should have politely declined, got dressed, paid her a big tip and sent her on her way. I did none of those things.

I had been pent up way too long. Not just with my lust for Tara, but all the months of Janice's refusals to touch me, the decline in our sex life. I could not resist having a woman's hand on me. I needed this.

I lay my head back and watched Esme's tits move as she pumped my cock. The shaft was slick with massage oil and the foreskin slid back and forth over the purple head, lubricated by a mix of oil and my precum.

Esme was very good at her job and I was enjoying myself immensely, but I knew one thing about myself. I did not usually cum from a handjob. A mouth, a pussy, an asshole, of course, but it had been a long time that a hand other than my own had brought me to orgasm.

Five whole minutes passed. I could see on Esme's face that her arm was getting tired. She tried several things, speeding up, slowing down, fondling my balls, but I was still not ready to cum.

I was about to tell her she could stop, thinking I would finish myself, either right there or after she left when the door to my office was opened.

My head swung around, suddenly very embarrassed and guilty. Esme looked up as well, and both of us watched Tara walk into the room.

My assistant surveyed the scene, Esme with her top open, my cock in her hand. Me, shiny and fully naked, laying on the table.

"It's not.." I started to say.

"I'm just letting you know you have that call in five minutes. I can push it back if you aren't finished here, though," Tara said, interrupting me.

"He won't cum," Esme said, slightly petulantly. "I have another massage upstairs soon. I can't wait all day."

"I paid for the full service, Esme," Tara said sternly, walking into the room. I couldn't take my eyes off of her. "I expect you to complete the job."

Tara walked to stand beside the table, looking down at me.

"Is she not doing a good job, sir?" She asked me.

I was at a bit of a loss on how to proceed here. I was fully on display, naked, being jerked off. Esme's hand did not stop stroking me. Having Tara watching was even more sexy.

"She's doing fine," I managed to say.

"Good," Tara said. "But I can only push your meeting so far. I hope you can wrap this up soon?"

She placed her hand on my stomach just above where the trail of trimmed hair led down to Esme's pumping hand. My cock twitched.

"He likes that," Esme said.

"Really?" Tara said, smiling slyly. "Do you sir? Two women's hands on you? Do you like that?" She began to slowly run her fingers across my pelvic bones, the light touch feeling like electrical jolts.

My mind went to an image of Tara and Esme both on their knees in front of me, mouths open as I jerked my cock, cumming across their pretty faces.

Suddenly I was very close. I groan and thrust my hips into Esme's fist, my cock throbbing, my balls tightening. Tara looked down at my cock and I saw her lick her plump lips.

"Fuuuuuuck," I moaned as I released a heavy, pent up load. Cum sprayed up my stomach all the way to my chest, covering Tara's hand where it rested.

Esme pumped out the last few spurts, coating her hand in my spunk, before releasing me.

"Good job, Esme," Tara said, looking at the mess all over me. "Please clean him up so he can be ready for his meeting."

Tara looked at her hand, my cum dripping off of her fingers. She slowly raised them to her lips and sucked my juices off of them.

"I'll get my laptop while you dress, sir," she said and turned to leave the room.

I lay there catching my breath as Esme used a towel to clean her hand and wipe the cum off of me.

"Um," I said, "I don't know how much cash I have for a tip." I assumed that she would be expecting one. "I didn't know that this was happening. Let me grab my wallet and check."

"Don't worry about it," Esme said, buttoning up her top. "Your assistant has taken care of everything. I'll be back next week. See you then."

I got dressed as Esme broke down her table and got ready to leave in an efficient manner.

She smiled at me then followed Tara out the door.

I sat back, straightened my tie and glanced at the agenda for the meeting, still processing what had just happened.

+++++

To say that nothing further sexual happened that week would be less than true.

Each evening I video called my assistant and chose her outfit for the next day. We talked longer and longer each night, and I usually stroked myself while we did so, looking at the young woman on my phone. If she ever knew she did nothing to let on.

I got to know my assistant much better. She was very driven, but also often wracked with self doubt. She never let it show but she admitted it to me during our long talks. I did my best to reassure her that she was practically perfect.

She was single and seemed content to stay that way. I hoped that she was not refraining from dating on my behalf but she assured me that she was just out of a longer term relationship and wanted to spend time getting to know herself better.

Each morning she presented herself for my inspection and I got a great look at her body. I stopped hiding how aroused I was during these inspections. Judging by the wet spots on Tara's panties when I looked her over, she found them exciting as well.

It was strange how we fell into a routine. There was a part of me, of course, that wanted to grab Tara and throw her down on my desk and take her. More than just a part, really, but I refrained. I was not quite ready to compound on the small betrayals of my wife that I was already performing with the one final big one.

Tara wanted me to, I was sure. Her eyes when she looked at me when I inspected her were full of lust and need. Maybe that was part of it. Maybe I enjoyed denying her what she seemed to want so bad.

The weekend finally arrived and I was struck with the fact that I had no pretence for calling Tara and choosing her outfit if I was not going to see her until monday. I thought about it all Friday, not sure of how to proceed.

Tara did not mention it so I let it slide but that night, sitting in my office, Janice once again asleep before me, I had my phone on my hand again. I considered putting it down. Going to bed.

Instead I called Tara. She picked up instantly.

"Hello," she said. "I'm glad you called."

The phone showed her wearing a white, oversized hoodie. She had her hair down, and seemed to be sitting on a couch.

"I almost didn't," I said. "No outfit to choose for tomorrow, I guess."

"I guess you are right," she said and sighed theatrically. "And I like the inspections so much!"

"Do you," I asked. "What do you like about them?"

I was genuinely curious. I was enjoying myself but I was unsure what Tara was getting out of our odd relationship.

"Oh," she said and seemed to think about it for a moment. "I guess... Well, often it feels like I can't control my own mind. I'm always thinking of many things at once, trying to figure out how to get them all done. It's what makes me good at my job, but it can be a lot."

She sighed and ran her fingers through her hair. She took a sip of red wine out of a glass she lifted into frame.

"When you decide what I am going to wear, and in the mornings when you inspect me," she continued. "Those times, though, it all quiets down. I'm totally in that moment, not thinking of anything but you. I love that. I feel safe and in control. Controlled. Also, seeing you get turned on for me turns me on."

I smiled.

"It does? I'm glad it does," I said.

"It really does. I just..." she paused and took another sip. "Sometimes I wish you would do more though. I imagine you reaching out, touching me. And, if I'm honest, more than sometimes. Every time."

"I'm sorry," I said. "I don't want you to feel bad. It's just..." I sipped my own drink. "I'm married. I don't want to ruin everything. It just seems so risky."

"I don't care that you are married," Tara said. "I hate that she doesn't treat you right. I can't believe she doesn't take care of you. It's not fair to you."

"Hey," I said. "She's not... I mean, she's a great wife. I love her. She treats me fine."

"Does she fuck you like you need?" Tara asked. I paused but did not answer the question.

"See," she went on. "That's not right. I can tell you don't get what you deserve. Just like I don't. Even my last boyfriend, I had to end it with him. He was great, but he only told me what to wear if I begged him. He wouldn't take charge. He treated me like I was precious. All I wanted was him to throw me down and fuck me."

The image of throwing Tara down and tearing off her clothing flashed through my mind. If that was what she wanted, her boyfriend was an idiot, not giving it to her.

"I can tell, sir," Tara said, "that you would fuck me like I needed. And I would give you what you need. But not before you are ready. I promise I will do whatever you want when you want."

"I'm not sure what I want," I said, honestly. "I had pretty much resigned myself to the life I have now. I'm not sure what to do with what you are offering me."

"No one is making you decide now," she said. "I just want you to know how I feel."

There was a silence between us for a few moments. Then she sighed.

"So, I know that I won't get to see you tomorrow, but do you want to choose what I wear when I hang out around the house all day tomorrow?"

"Sure," I said, glad that we seemed to be moving past a conversation I found difficult. "Let's see what you have."

She moved and placed her camera on the coffee table in front of her and leaned back. Her entire body was now in the frame. She was wearing an oversized hoodie that came down to her upper thighs. Below it her legs were bare.

"Well," she said, "this is one option. I love this hoodie. It's very cosy."

I smiled.

"Yeah," I said, "it does look comfortable."

"Or," she said, gripping the bottom of the oversized garment, "I sometimes wear nothing at all."

I took in a breath and held it as she pulled the hoodie up. It slid up over her stomach, over her breasts. The hoodie caught on them, lifting them a bit before they dropped free. I had seen them in only her bra many times but this was the first time I had seen them completely naked. They were perfect. Very large, but still pert, sloping naturally towards her hard, pink nipples. I licked my lips. She finished pulling off the hoodie and dropped it on the couch beside her.

I couldn't help but reach down and push my hand into my pyjama pants, gripping my hard cock.