Work Experience

A virgin young man is trained by his new boss in the art of pleasing women

WORK EXPERIENCE

My name is Steve and this story is about events that happened at my first job upon leaving school at eighteen.

In those days I was eager to please, having landed an entry level position at a fairly large corporation.

Of course all thoughts of quickly becoming an important cog in the corporate wheel were soon dashed when I discovered that most of my duties involved fetching cups of coffee and distributing items from the mail room.

Still, we all have to start somewhere.

Progression usually required some more prominent figure, a line manager or executive to adopt you and mentor you through the process of learning the ropes.

For the first few weeks I was what they called a 'floater'. Not a very glorious title, but it simply reflected that I floated from one department to another depending on need.

It was the Monday of that week that I first met Mrs Gregory.

Mrs Gregory was around fifty, curvy and smart. She may have been shorter than most of the men, including me, at around 5'2", but she held her own with the best of them. Some thought she was quite fearsome, though that might have been said just to wind me up.

"Watch out for her." said one male colleague, "She has been known to send them home in tears."

'Them' being wet behind the ears grunts like me.

For most of that week I doubt I was even a blip on her radar. I just did as asked and kept my nose clean. That was until the Friday afternoon, when I realised I had fucked up big time.

It was a serious mistake. Career ending, I thought. I even considered just chucking in the towel and going home.

But then, throwing away a job wasn't much better than being fired from it, and I also felt bad that my error was going to cost ordinary people a large amount of money. I couldn't just walk away from that.

In the end, at around 3:00pm I took a deep breath and knocked on Mrs Gregory's door.

"Come in." she said abruptly.

I entered and stood waiting for her to acknowledge me. She looked up from her laptop, puzzled that I didn't seem to have a purpose being there.

Mrs Gregory was astute though. Immediately her expression changed as she saw my white face.

"What's wrong?" she asked, removing her glasses and sitting back in her chair as if bracing herself.

I explained what had happened and how sorry I was.

She listened without getting emotional or shouting or any of the other reactions I was expecting. She waited for me to finish.

"Right." she said after a moments pause, "We need to sort this."

"I'm so sorry, Mrs Gregory." I said once more.

"I'm sure you are." she said, without cynicism, "But 'sorry' doesn't easily fix things."

I watched as she put back on her glasses and typed on the keyboard.

"If there's anything...." I began.

"Yes, you can be quiet for a second." she said calmly without looking up from her screen.

I stood and waited.

After about five minutes, though it seemed much longer, she looked at me.

"Right." she said, "If you want to help sort this out, you must listen and do exactly what I say, okay?"

I nodded.

"No winging it, thinking you can do better. Just stay on script and we may be able to rectify this, but we're against the clock. Concentrate, okay?"

I confirmed my willingness to put all my efforts at her disposal.

Mrs Gregory outlined our course of action and instructed me on the steps I needed to carry out in order to make it happen.

Once she was sure I understood my role, she sent me on my way, reminding me of the time constraint.

I walked swiftly to the lifts to go down to the mail room where I was to intercept a package that was due to leave within the hour. She had forewarned them that I was on my way.

Just before the bank of elevators Mr Johnson collared me with a task.

I had to brush him off, much to his disdain. "Who are you running around for?" he asked as I waited for the lift.

"Mrs Gregory." I said, and saw him nod and laugh.

"Got you by the balls already, has she?" he said.

If only he knew.

The lift arrived and I stepped in, the doors closing on Johnson's Cheshire cat grin.

The mail room workers hustled me to the pallet that was to contain the package we needed, and we searched through the hundreds of envelopes and parcels.

I kept glancing at the clock and could see workers beginning to load other pallets into waiting vans.

They're early, I thought in a panic.

Eventually my hand alighted on the one we were searching for and I shouted my thanks to the mailroom as I ran back to the elevators.

While I was gone, Mrs Gregory had been using her charm and cajoling skills to smooth troubled waters with other departments and rectify the mistake I had made without actually highlighting the mistake itself.

I returned to her office holding the package discretely under my arm.

Being a Friday there was already a thinning out of staff on our floor as people left for an early weekend, their work all completed and without errors.

For Mrs Gregory and I we still had a shit load to do, but I was still very impressed with how focussed and calm she was in the process. I understood now why she had reached this level in the corporation.

Suffice to say that with a few minutes left until 5:30, we were finally able to sit back and agree that disaster had been averted and my problem had been discretely and quietly expunged from the system.

I still expected her to fire me though, but at least I wouldn't have other people's financial pain on my conscious.

"Well, Steve." she said, regarding me from her chair, "That was exciting, wasn't it?"

"I could do without that sort of excitement, Mrs Gregory." I said, bracing myself for the inevitable.

"Sit down, please." she said, indicating one of the two chairs the other side of her desk.

Here it comes.

"What you did was avoidable and showed you lacked concentration in your work."

I nodded. My face was red, my heart pounding and my future extremely bleak.

"However," she continued, "when you might well have run for the hills, or tried to blame others, you did the right thing and came to me. That took guts."

Now she stood and walked to a filing cabinet located against the office wall.

"Not only that," she said, unlocking and opening one of the drawers, "but when I told you how we were going to put things right, you listened and you acted to the letter of my instruction. I like that. I like that a lot."

Mrs Gregory retrieved a large brown bottle and two glasses from the drawer and pushed it closed with her elbow.

She placed the bottle of cognac on the desk in front of me and set the glasses alongside it.

Now she sat in the chair next to me and stared at my face. Her subtle expensive perfume was detectable. I breathed it in.

"So, I think you deserve a second chance." she said with a smile.

I was lost for words.

"In fact, I believe you and I worked very well under pressure today and that bodes well for your future here, in MY department."

I had my mentor!

"Mrs Gregory, I.....I don't know what to say." I spluttered, totally floored by the unexpected turn of events.

She uncorked the bottle and poured two generous measures into the glasses.

"I think we deserve this, don't you?" she said and pushed one glass closer to me and raised her own to sip the liquor.

Being eighteen I wasn't that used to neat alcohol yet, having mostly cut my teeth on ales and lagers, but I too sipped at the liquid and was pleasantly surprised at the lack of burn and the subtleness of the flavours. I suspected it was a very good brand.

"Good." she said.

By now it was approaching 6:00pm and I was going to miss my usual bus home, but it hardly felt appropriate to leave now that my boss was actually pleased enough to share some expensive booze with me.

Office lights had been switched off leaving only our own and the corridor outside. The building was eerily quiet with just the hum of air con to break the silence.

"So, what do you think?" she asked.

"Mrs Gregory....I....I really, really want to work for you. You showed me skills today and how to remain calm and I know I can learn so much from you."

She was smiling at me as I offered my profuse compliments.

"And, I owe you! I really do." I said, becoming quite emotional, "I know it would have been perfectly within your power to fire me, but you didn't. I will be eternally grateful for that, I really will. I will do anything you ask from now on. Anything!"

Her eyebrow arched as I finished and her smile broadened.

"That's what I like to hear." she said, "A young man like you could go far in this business, but you must listen and learn and, sometimes, act without question when instructed. By me, that is. Those others you can cheerfully ignore."

We both chuckled.

Mrs Gregory kicked off her kitten heel shoes and stretched her toes.

"It always feels good to get my shoes off at the end of the day. I spend so much time going from one department to another it sometimes feels like I've walked ten miles."

She looked at me and grinned and then, to my complete surprise, she lifted her feet up and rested them in my lap.

"How are you at foot massages?" she asked and sipped her drink.

I stared at her small feet clad in dark grey stockings and could feel the heat of her body resting on mine.

"I...I...I don't know." I said, honestly, "I've never given one."

"No girlfriend?"

My face blushed.

"I....no, I don't have anyone...like that." I replied.

"Boyfriend?" she asked.

My face flushed darker.

"No!" I said, "I don't....I mean, I like girls."

She chuckled at my discomfort and wiggled her feet.

"Well, put your glass down and listen to my instructions. It'll stand you in good stead with the ladies, I can assure you."

I complied.

"Now the art is to not tickle. There are some circumstances where tickling is okay, but not in this scenario, okay?" she said.

I nodded.

"Place both your hands on my foot with your thumbs on the underside. That's it."

Her foot looked so tiny in my hands and I could tell through the stocking that her nails were trim and painted a subtle rose red.

"Now press....gently....that's right....oh yes, very good."

I pressed and kneaded her foot and she sat back with her eyes half closed and made encouraging sounds. I had a feeling this might be one of my duties in future but I couldn't say I was displeased at the thought.

After a few minutes of massaging her right foot she instructed me to attend to her left.

Now that I was becoming proficient at foot massage and she was sitting back with her eyes closed enjoying it, I had the first opportunity to look at Mrs Gregory as a woman, not just as my boss.

She had dark, curly hair cut quite short. Simple gold studs in her ears, impeccable makeup that highlighted and accentuated her features without being obvious. Her lipstick was a soft, red terracotta shade and her lips themselves were full and rather inviting. I found myself pondering what kind of man Mr Gregory was to be married to this lady.

Around her neck was a discrete, string of iridescent white pearls.

Her blouse was white and contrasted nicely with her tanned skin. She obviously holidayed abroad.

Her skirt was dark navy, quite tight at her hips and came down to just above her knees.

Her legs were thicker than most of the girls my own age, but I liked the shapeliness of her well defined calf muscles above her small ankles. I wondered if she worked out at the gym to keep her figure.

"Taking it all in?"

Her voice startled me and I looked up to see she had been watching me looking at her legs.

"I.....I...was enjoying giving you the massage." I said, as the first thing I could think to say.

"Well, that makes two of us then." she said. "But you can stop now."

My thumbs ceased their movement though she made no effort to remove her feet. I reached for my glass and took another sip.

"So, how come no girlfriend?" she asked.

Under other circumstances I would have been within my rights to object to these personal questions but, whilst it made me uncomfortable, these were not normal circumstances.

"I just...just haven't." I said.

She stared at me. "Are you a virgin?"

Once more my face turned beetroot red and I stared at her feet.

"It's okay." she said, "I was twenty four before I ever had sex. I know that was an age ago now, though."

I was half tempted to lie to her. It's funny how important that sort of thing is to an eighteen year old, especially when you perceive that everyone you know of your age seem to be going at it like bunny rabbits.

But I owed her my loyalty and that surely included my honesty.

"I just haven't met....well, you know, someone who wants to have sex with me, I suppose."

She was looking at me seriously, but without pity or condescension.

"There's no hurry. Believe me, people aren't having as much sex as you might think, even at your age."

Now I wondered if she was also a mind reader.

"But you must grab the opportunity when it arises....so to speak." she said with a chuckle and sipped more at the cognac, "Don't be scared of it."

She moved her feet slightly in my lap, whether by intent or by accident, and I felt them rub against my cock.

"Maybe we need to include that as part of your training too." she said with a sly smile.

In my innocence I wasn't sure what she was now referring to.

"I am looking forward to being trained, by you." I said, wondering where those words had come from and feeling embarrassed for being inarticulate.

Now she raised her legs, giving me a brief view up beneath her skirt at her stocking tops and pale thighs beyond, and placed her feet back down on the floor and stood.

I imagined it was now time for us to leave.

But, instead of walking away from me she took a step closer and bent forward, lowering her face level with mine. Her perfume wafted into my nose and her breath was hot on my face. She didn't speak, she simply kissed my lips.

I wasn't an experienced kisser but I knew the rudiments. I also became extremely aroused at the touch of those soft red lips on mine.

I could feel her tongue exploring between my lips and I opened my mouth to receive it. She pressed harder against me and tilted her head as our tongues rubbed together.

When she finally broke from our kiss her face had more colour and her lipstick was a little smeared.

"Nice." she said, standing upright. "Good kisser, young Steve. You're ticking quite a few boxes this evening."

I stared at her standing in front of me in her expensive business attire and wondered how far we would go, alone together in her office.

"Remember," she said, "if you want to please me, you must do everything I instruct you to do, without question. Right?"

"Yes, Mrs Gregory." I said, "I do want to please you."

"Good." she said, "You can start by calling me Suzanne, at least outside of office hours."

"Okay, Suzanne."

Then, to my complete surprise she suddenly unfastened her skirt and let it fall to the floor. Without comment she stepped out of it and carefully folded it and placed in on her chair.

Now I gazed at her legs from ankles up past her knees and to her thighs with the suspenders holding up her stockings peeking out from just below the hem of her blouse.

"Undress." she said.

I paused, conflicted and embarrassed. I had to please her. Dammit, I wanted to please her, but what if, instead I just disappointed her? I didn't have an athletic body or bulging muscles. My dick didn't measure up to anything like the images I saw in online porn. And I was inexperienced and would make a fool of myself.

But, she had said she wanted to teach, or rather 'train' me.

She was waiting.

I stood, knowing my cock was pressing out against my trousers and that there was a warm damp patch showing on them.

I unfastened my long sleeve white shirt and pulled it off and put it over the back of my chair.

Her eyes never left me as I did my unsexy striptease.

To get my trousers off I needed to first remove my shoes, which I managed to unlace inelegantly while bracing myself against her desk.

With shoes and socks off I unfastened my trousers and soon they joined my shirt on the chair back.

I stood in my boxers, a pitched tent at the front of them and a dark patch of sticky liquid at it's tip.

"Those as well." she said.

I took a deep breath and, with furiously blushing face, pushed down my boxers and kicked them to the side.

I stood naked and erect before my boss.

Suzanne stepped closer once more and her hand reached down to grasp my cock. She looked up from it and into my eyes and stood on tiptoes to kiss my mouth again. I felt my cock brush against her blouse and wondered if she realised I was smearing pre-cum on to her clothes.

Her lips parted from mine and she stood back down, her hand sliding my foreskin back and forth over my glands.

I was close to coming and tried desperately to focus on anything else.

Suzanne, being worldly wise and astute, could tell my state and let her hand drop from my sticky cock.

Then she reached under the hem of her blouse and I watched as she slid her panties down and stepped out of them. She picked them up and tossed them on to my chair.

"A gift." she said.

Now she set her bum back against the edge of the desk and lifted herself to sit on the top of it.

"Come, kneel there." she said pointing at the floor in front of her.

I did as asked, my chin level with the desk top.

I watched as she spread her legs apart and pulled up her blouse to expose herself to me.

Suzanne had a tuft of black pubic hair above her pussy, but the area directly around the lips was shaven, smooth skin.

"Touch me." she said and I tentatively placed my hands on her thighs just where the stockings met her skin.

"Here." she said, and with her right hand she placed two fingers on her fleshy lips and parted them, exposing her internal pink, wet skin. I could smell her scent now and moved my face closer to her.

I took one finger and placed it gently on the exposed skin. It felt warm and her moisture was slippery.

"Inside, but gently. No scratching." she said, watching my every move.

I pushed the digit in between her soft lips and encountered more of her hot, slippery liquid. I felt the friction of her internal wall rubbing against my skin as I moved my finger within her.

"Now take it out....slowly, and suck it." she said softly.

I did as instructed, seeing my wet finger slowly emerge from inside of her and then placed it into my mouth, tasting and smelling her juice.

"Good boy." she said, "Now, you know what the clit is, right?"

I nodded, having had an internet education.

"Lick it."

I pressed my mouth to her pussy and let my tongue search for the little knob of sensitive receptors.

Suzanne groaned and moaned as my tongue rubbed against her and her hips moved making it hard for me to stay on task.

"Put your finger back inside me.....just the one." she gasped and I did as asked.

I could feel her hands gripping my head and steering me to places she wanted my tongue.

Suzanne placed her legs onto my shoulders and her stockings rubbed pleasurably against my skin.

Her wetness was flowing out of her now and running down my forearm. All I could taste and smell was her pussy.

"Put another finger in me." she said, breathlessly and I withdrew my forefinger and then slid it back in accompanied by it's neighbour. She felt tighter with my two fingers inside her.

"Twist them." she said, "Keep licking."

Her thighs were hot and tight against my face and her hands pulled and tugged at my head as she was lost in the world of her own pleasure. I felt invigorated that I was making her feel so good. My awkwardness and embarrassment was forgotten as my fingers twisted within her and my tongue teased her clit.