New Assistant Pt. 02

This is Part two of the series and I suggest you check out chapter one for context. Of course all characters are over 18. If you enjoy it please feel free to like and comment. I always enjoy hearing from my readers!

It was difficult to have a work related conversation with my cock in the mouth of my pretty young assistant. But not, I was discovering, impossible.

Tara had been my assistant for just over a month at that point, having been assigned to me after I recieved a promotion. The new job came with a boatload more money, a private office, and a personal assistant.

It turned out that I was a very lucky man. My assistant took her role of taking care of me very seriously. My schedule was perfectly prepared for me every day, I always had a hot cup of my favorite coffee close to hand, I was rarely bothered by calls or meetings that were wastes of my time, and she made sure that my every sexual need was taken care of.

Tara was very pretty, with auburn hair, an oval face, which she did up lightly with makeup, plump lips, green eyes and freckles across the bridge of her nose and across her chest.

She was short, at only 5'4, but very shapely, with a great ass, trim waist, and large double D breasts. She was always a nice sight in the morning.

Soon after hiring her, we had established a bit of a game where I would call her before I went to bed and choose the outfit she would wear the next day. Each morning she would present herself to me, to show that she had worn what I had asked of her. Before long I was fucking her.

The complication was that while she was young, 24 years old and single. I was 43 and married to my wife Janice. I loved my wife, even if our sex life had tapered off to almost nothing, but I could not help but take what Tara had been offering since day one.

I was fucking Tara at least once a day, sometimes after our morning meeting when she presented her outfit to me, other times later in the day. I was amazed at my own sexual stamina, but there was something about her that kept me able to get hard again and again.

That particular morning, after her inspection - I had chosen a cream colored blouse that cut relatively low in the front so that I could look at her cleavage throughout the day, a pencil skirt and black stockings - we knew I had a call with HR scheduled so instead of fucking she decided to give me a quick blowjob.

I rolled my chair back from the antique wooden desk and was leaning back, eyes closed, hand resting lightly on the back of Tara's head as she serviced me when my phone rang.

Tara's mouth was full of my thick, 7.5 inch cock, pushing it into her throat, nose against my trimmed pubic hair, before drawing her lips back along the entire length while her tongue massaged the bottom of the shaft.

"Fuck," I groaned, not close enough to cumming to quickly finish. "We lost track of time. You will have to finish later."

Tara looked up at me, my cock in her mouth, a bit of drool dripping down her chin. Her green eyes danced with mischief. She reached behind her up to my desk and hit the speaker button, accepting the call, before diving down taking me deep once more.

I stifled a groan when I heard the voice on the other end.

"Brian? You there?" It was Mandy, one of the girls from HR.

I had always liked her. She was cute, friendly and a bit flirty. She had black hair that she kept shoulder length, a pleasant face with dark eyes. Her nose was a bit long, but her smile lit up her face. It was hard to judge her body because she always dressed very professionally, but she had nice legs and a round ass. The blazers she regularly wore hid her breast size. I wasn't sure how old she was, but I suspected in her mid to late twenties.

A couple of years before we had gotten drunk together at a company outing and our conversation had turned to sex. I suspected that night that she might have been open to taking me home but I chickened out and left, heading towards my own place and my wife. Ever since she had always been extra flirty.

"Uh, yeah," I managed to say. "Here I am. How... how are you?"

It was difficult to concentrate with Tara's expert mouth sucking on my cock. She kept a steady pace, taking the entire length again and again, making sure to keep the sounds very quiet. I could see her reach between her legs and start to rub herself as she serviced me.

"I'm great," Mandy said. "It's been a pretty decent week! I even had a date last night."

"Oh yeah?" I said, determined to keep my voice level despite my urge to grunt and moan. "Have fun? Get lucky?" I cupped the back of Tara's head and lifted my hips pushing as deep into her throat as I could go before releasing her to continue her sucking.

"Mr. Whitecastle!" Mandy said with mock outrage. "You can't ask a woman that at work! Especially an HR rep!" She continued in a pretend whisper, as if we were sharing secrets in an open area. "But maybe I did. If you can call something like that lucky."

I was opening my mouth to answer when Tara suddenly sped up, head rising and falling quickly taking my breath away.

"Not a great lover, this guy?" I managed to ask.

"Frankly no," Mandy said and sounded truly disappointed. "I'm so sick of the dating apps. You meet a guy and chat and he comes across in a certain way, and I expect something and the reality is almost always a total let down. I think I need someone a bit older."

This made Tara smile. She took my cock out of her mouth, holding it in her hand beside my face, and mouthed the words, She Does, before returning to sucking me off.

"I wonder," Mandy continued with a voice filled with flirt, "where I can find one of those..."

"I'm sure you will manage, Mandy," I said. It was getting harder to hold back my climax and needed to wrap this conversation.

"I don't mean to rush you but I have another meeting shortly. Did you want to talk about...that thing?" I could not, at that moment, think of what we were scheduled to talk about.

"You are no fun, Brian," Mandy said. "But you are right. So the way I see it it is like this..."

She went on to talk about a staffing issue I was having. I needed to add one or two more people to one of my teams in order to get a project across the line. Unfortunately I had no one available and no budget to hire on new staff. Mandy began to lay out ways we could borrow from other teams.

I paid no attention to her. I add the odd 'ok' or 'sure' when she paused but my focus was on the girl between my thighs. I had my hands on the back of her head and was pulling her face to my stomach as I lifted my hips to thrust. She was making quiet 'glug, glug, glug' noises as she took the length of my cock. I worried a bit that she would be heard but was too far gone to truly care. Mandy seemed not to notice.

I could feel my climax approaching, the way my balls were tightening, the tingle at the base of my rod. My eyes were locked on Tara's green ones, a trickle of tears dripping from the corners, but they sparkled with enjoyment. She really did seem to love servicing me. Drool was dripping down her chin, and onto the floor in front of her. My ass was clenched as I thrust into her mouth, holding onto that perfect feeling of about to cum for as long as I could.

Suddenly I crested my peak, unable to hold that edge any longer. I pushed down on the back of Tara's head as I shoved my hips forward as I came, my hand a fist which I raised to my mouth and bit to stifle the groans that wanted to erupt from me.

I could feel the explosion, the heavy spurt of cum that released directly into Tara's throat. My heartbeat was a roar in my ears, preventing me from hearing or thinking of anything but this perfect moment of bliss. I pulled back as I came another spurt and saw some leak out from her lips wrapped around my cock. She raised her hand to cup under her chin so she didn't lose any of my cum. She continued to suck, drawing out every drop I had.

"Brian," I finally heard as I fell back into my chair, head rolling back, looking at the ceiling. Between my legs Tara slowed her movements, lessened the suction of her mouth as she stroked the base of my cock, milking every last bit of my climax.

"Yeah," sorry, "I said, catching my breath. "An email came through. I was a bit distracted. I missed that last bit."

"I was just asking if this all sounds good to you," Mandy said. "I think it covers everything you need. Can we go ahead?"

"Sure, Mandy," I said. "Can you just email me a write up of the plan. I'll go over it with the fine tooth and sign off."

"No problem, Brian," Mandy said. "It's always a pleasure working with you."

"You too Mandy," I said. "If that's everything?"

"Oh," she said, as if something had just occurred to her, "it's been a bit. How is Tara working out?"

I looked down at Tara who smiled at me, and pushed the cum they had leaked out of her mouth back in and swallowed it.

"Honestly," I said, smiling, speaking to Mandy but intending the words for my assistant, "she is absolutely perfect."

"That's great!" Mandy said, pleased with herself for arranging this. "I knew they would be a great fit!"

"It really is," I said. "We fit together perfectly. Thank you for assigning her to me."

We hung up and I rolled my chair back to let Tara out from under the desk holding her hand, helping her stand.

"You are a very bad girl, Tara," I said, smiling at her.

"Me," she said, mock innocently. "I'm not sure what you are talking about. I'm just doing my job. Taking care of you."

She reached down and pushed my sagging cock into my pants and doing up the zipper and button.

"I'd better go check your email and go over that HR plan for you. I don't think you were really paying attention for some reason. I'll let you know what it says."

I let her leave my office and go to her desk. I sighed happily and tapped on my laptop. I really did not have too much to do. Tara seemed to take on most of my work and my teams were strong and needed very little oversight. It seemed to me that the higher I rose in the company the less I had to do.

My cellphone buzzed on my desk and I picked it up. There was a text from my wife, Janice.

-hope you are having a good day.Don't forget to pick up the dry cleaning on your way home. Love you.

I sighed. I felt bad, cheating on Janice. She was a great partner and my best friend. The only thing our relationship lacked was sex. If that had not waned over the years I'm sure I would have been able to resist Tara. I thought so anyway.

-sure I'll remember, I typed. -Love you too.

+++++

At the end of the work day Tara and I were chatting. She was sitting on the edge of my desk, leaning against her palms flat on the surface just behind her. The pose put her pert but full breasts on display, something I was convinced she knew.

My hand was on her thigh, high up, under the skirt, fingers teasing the soft flesh of her inner thigh, my fingertips drawing small circles.

It was Thursday and we often spent the last work hour of the day like this, enjoying each other's company, avoiding leaving. We knew that we would talk on a video call later that night but it was not the same. We extended our time together as long as possible.

"So," I asked. "What's your plans tonight?"

"Not too much," she answered. "You know me. I like to keep things quiet."

This did seem to be true. She was young enough that I would have guessed that she would go out with her friends, party, go to clubs, maybe pick up boys. But she seemed to prefer to stay home and read or watching a movie.

"So Mandy is pretty cute, isn't she," she said, suddenly changing the subject.

I blinked. If this was some other woman, my wife for example, this might be a trap. I did not get that vibe off of Tara, so I answered her truthfully.

"Sure," I said. "Very cute. Not as cute as you, of course, but yeah. I would say so."

"She has a crush on you, you know?" Tara said.

I shook my head.

"Nah. She's a bit flirty, sure, but I don't think so."

Tara laughed.

"She isn't the only one. You are pretty popular with the girls who work here. Most of them think you are hot and would jump your bones any chance they got."

"I find that a bit hard to believe," I said. I was 5'10, blond with a beard that was a bit grey. My eyes were pale blue. I kept in decent shape. If I was honest with myself I thought I looked ok. Nothing special but not too bad. "I think it's just because all the other executives are creepy wrinkled old men."

"I'm sure that helps," Tara said chuckling. Then she got serious. "But that's not just it. You are very good looking, you carry yourself with confidence and you are a good, caring person. Girls react to that. I'm just the one lucky enough to catch you."

"I'm the lucky one," I reassured her.

"Anyway," she said, "Mandy. She had a crush on you. And you think she's cute. This is established. Now, the question is, do you want to fuck her?"

I paused for a moment.

"I'm not sure what you want me to say," I said. "I could go my whole life and never fuck her and feel fine about that. I was loyal to my relationship with my wife for a long time. That being said, now that I have had...a relationship on the side...I find the idea intriguing."

"Oh," Tara laughed. "Am I broadening your horizons? I like that. So, I think you should fuck her. Or rather, I think we should fuck her together."

I took a moment to take Tara in. At this point I knew her pretty well. She was speaking very confidently, lightly. I could tell, however, she was very nervous. She was fidgeting with the hem of her skirt, looking down at her hands while she waited for me to answer.

"You want this? Why?" I asked. "You know I'm happy with you, right? That I don't need anyone else?"

"I know," she said. "I know that. And it makes me happy. But, honestly, the idea of fucking a girl with you, of helping you fuck her, it...it makes me very horny. Very wet."

She took hold of my wrist and pushed my hand higher on her thigh.

"Feel how wet the idea makes me," she said.

My fingertips found the fabric of the black thong panties I had told her to wear today. I liked her to wear thongs because I liked to pull them aside and fuck her while she still wore them sometimes. I could feel the heat of her sex through the fabric. I hooked my fingers in the leg opening and tugged them to the side and pushed my fingers between the lips of her pussy. She was, indeed, very wet. I started to rub her clit, making her moan.

"Very wet," I said. "I like this idea. If we can pull it off."

"I have a plan," Tara said, biting her lip as I pushed a couple fingers into her, leaving my thumb to rub on her clit.

"That doesn't surprise me," I said. "I think you always have a plan."

"True," she said, rocking her hips in time to my fingers and rubbing. "Plans within plans within plans. The girls go out for drinks every Friday night. Mandy included."

I knew this. I had been invited to join them a couple of times but had always refused, preferring to just go home.

"Sure," I said.

"They, oh damn, yes. Just like that...' she said. "They invited me.. The bar is just up the street. I said I would go. You should come with me. Your wife is busy, right?"

I nodded. Janice had a work thing in another city Friday evening. She was fling out in the morning, staying over night and then returning some time Saturday.

"Ok," I said, continuing to play with April, fingers slowly pushing into her, curling along the top of her channel and drawing back, making her moan. "I guess I could come for a drink. And then?"

"Leave it to me," Tara said.

"Ok, I trust you," I said. I reached forward and unzipped the fastener on her hip, loosening her skirt enough that I could push it up and move between her thighs. I dropped my mouth to her cunt and began to suck and lick while my fingers sped in her.

Within five minutes I had her thighs clamped around my ears and her fingers in my hair as she came against my tongue.

"I need to be inside you again," I said hoarsely, after she had come down from her climax. I moved up her body and kissed her as I pushed into her wet and ready cunt.

I fucked her hard and fast on my desk, trusting the soundproofing to contain the cries she made as our bodies slapped together. Neither of us were taking our time and within another five minutes I was cumming deep in my assistant while she wrapped her legs tight around my ass.

+++++

An hour and a half later I was walking through my front door, the bags of our dry cleaning over my shoulder. I was greeted with the delicious smell of food. Thai, if I guessed correctly.

"Janice," I called out. "You home?"

My wife came around the corner, entering the kitchen. She had been home at least long enough to change out of her work clothing. She was wearing a tank top and jeans. Her hair was pulled back into a ponytail. She looked good, reminding me that, while I might have a hot young thing at work, I was married to a beautiful woman.

"Hello," she said, starting to unpack takeout food from the paper bags they had been delivered in. My guess had been correct. She had brought home food from our favourite Thai place.

"What's the occasion," I asked, gesturing to the food and dropping the dry cleaning to drape across one of the counter stools.

"Nothing really," Janice said. "I just didn't feel like cooking. I still have to pack tonight. And I got extra so you can have leftovers for supper tomorrow when you are here on your own."

"Good idea," I said. "Thanks. Let me help."

I entered the kitchen and started to pull down plates and set the table. Janice stopped me with a hand on my chest, looking up at me.

"Hey you," she said, smiling, tilting her head back. I took the hint and kissed her. Usually our kisses were quick, but this time she opened her mouth and our tongues flicked against one another.

Suddenly a thought occurred to me. Had I washed my face properly earlier? I had spent a good chunk of my day with my face between Tara's legs. Could Janice smell her in my beard? Could she taste Tara's pussy on my lips?

My heart was pounding as these thoughts shot through my mind. I tried to melt into the kiss, tried to enjoy and appreciate that this was the woman I loved kissing me, but mostly I failed.

Janice, for her part, seemed not to realise what I was going through. I felt her sigh happily as she pressed her chest against mine. Her arms reached around me and her palms ran up my back. I made myself do the same for her.

When the kiss finally broke my wife looked up at me, love in her eyes. The guilt I felt at that moment, thinking about the way I had been betraying her every day, was like a punch to the gut. She looked at me with perfect adoration and trust and I knew that I did not deserve it.

Janice smiled slyly at me and reached between us and gripped my belt and began to undo it.

"Someone is frisky today," I said smiling, hiding my panic.

"I've missed you," she said, popping the belt open and starting to unbutton and zip down my zipper. "I've missed...us. I'm sorry that I haven't been much fun lately. I've been so busy, you've been so busy."

Her hand reached into my pants and under the elastic band of my underwear, gripping my cock that was slowly coming to life.

"I'm sorry that I've been neglecting you," she said, giving my cock a squeeze.

"Hey," I said. "It's ok. I understand."

Janice pushed my pants off of my hips and they fell to a pool around my feet. She smiled at me and began to lower herself to her knees. Again, the panic hit me. While my face might not still smell like Tara's pussy, there was no way that my cock would not. I had spent a long time inside her that day, and her juices must have coated my cock, the smell of them in my trimmed pubic hair.

"Um, wait," I said panicing. "I didn't get a chance to shower this morning and I was hot all day. The... um... AC broke? I was pretty sweaty. Why don't I go grab a quick shower?"