Mentor with Benefits

First of all, I'm the asshole in this story. The guy with a nice wife at home. The greedy bastard who wants more and gets it at work. So, if that's a dealbreaker, I won't waste any more of your time.

I'm an executive at a manufacturing firm in Atlanta. I moved up through the company through the good-ole-boy system. The guy who had the job before me was grooming me for it for a while, from as soon as he found out he was moving up to VP. So, when my promotion was announced, it didn't surprise anybody, especially my secretary Pam. Nothing surprises Pam.

Pam sits in the front office that guards mine. She is the gatekeeper. I brag about having an "open door" policy, but Pam makes sure everyone is afraid enough of her to not take me up on it without just cause.

Pam is around retirement age, was surely a looker in her younger years, and is easy on the eyes even now. She has short-cropped blonde hair and one of those leathered tans from spending every weekend at the lake house she got in her last divorce. She has a son who lives out of town. She drives a Mercedes convertible.

And she seems just fine living alone.

Pam always dresses professionally of course but isn't afraid to show deep cleavage. Enough to make me smile whenever I come in the door, and whenever she comes in my office and goes out of her way to lean over when she puts something on my desk. And while she is extremely protective of me, and of the power that comes with her station, she also makes sure I get whatever I need. And she has very good instincts when it comes to what I need.

During my first month there, my calendar was remarkably clear, thanks to Pam. I had the usual weekly meetings, but nobody just dropped by to chat. But it was only a couple of weeks in that I saw a late morning recurring appointment show up the second Tuesday of every month.

"Hey Pam, what is this 'Office Visit with Janet' monthly meeting?"

"She's a specialty parts vendor. She likes to come by monthly."

"Since when do I want to meet with parts vendors?"

"You'll want to meet with this one," she was coy, but didn't even smile. Just typed away during our conversation.

I didn't make the connection, but I knew to trust Pam.

The first time Janet showed up, I needed no further explanation. High heels, tight navy-blue dress, plunging cleavage, hair up, exposing a vulnerable neckline. Dark hair, long lashed, very red lipstick. And just a few freckles. I was taken aback, and she knew it.

If she mentioned her widgets, or whatsits, or spare parts, I don't remember it. But I remember the breathy sound of her voice and the way she parted her lips and leaned in when she sat at my conference table, at the corner with her legs turned towards me on the end, crossed, one heel dangling from a slender foot.

She did tell me that she was planning to start her own business. She said she was looking for a mentor to help her know how to get started and wondered if I had anyone on my staff I would recommend. When I volunteered, she feigned surprise and honor that I would take time from my important schedule for little-old-her. It seemed the least I could do, I said, in the spirit of promoting entrepreneurship.

"Maybe we should continue this conversation over lunch," I said, and she agreed. We rode together, in my 911, and her dress did all the right things in the seat. The seatbelt stretched tight between her breasts. When we arrived, she stayed in the car until I walked around and let her out, and her exit from the low car, holding my hand, was a work of art.

At that first lunch, at a quiet booth in a strip mall Asian restaurant, she did most of the talking, and I just listened, watched and enjoyed. She didn't talk about the start-up. But she talked about everything else. She had no filter. I heard about her divorce, her steamy 50-shades affair, and eventually her nights with her toy she named Elvis. I pictured all of it. I would be beating off to it that afternoon in the executive washroom.

When I drove her back to the office, I punched the gas to pass a line of cars, and her dress hiked up her thigh and she grabbed my arm in excitement.

That night, I got a Facebook friend request from her and accepted it. Her profile pic was a skimpy bikini selfie at a resort in the Caribbean, and I clicked "like". She was wearing a smile and a straw hat.

The next few nights, I stalked her page, liking the sexiest of her pics, going back several months.

The next week, she emailed me a photo of herself at her desk, blouse unbuttoned to below her bra, shirt pulled open, with a message, "Thinking of you." I freaked out a bit, getting this on my work computer, hoping the IT guys weren't scanning it. I encrypted a folder and dropped the pic in it for later reference.

The next month, we just met directly at our restaurant, which was a little disappointing not getting to ride together. She was already there, poised and posed at our booth, dress especially low cut. She didn't wait to comment about my stalking, "I wore this dress just for you. I noticed the pics you liked were the ones where I was showing the most cleavage."

I replied awkwardly, "well, you keep posting them and I'll keep liking them."

That gave her the excuse to talk about her take on nudity and the human form. How she cleans the house naked, mows the grass in her back yard topless, for the pleasure of the old man who watches her from his upstairs window. All the time she talked, she reached out and touched my hand, my arm.

"I hope you don't mind the picture I sent you at work. I guess I'm just flattered with all the attention you've been giving my pictures and wanted you to have one of your very own."

"Oh, not at all! But let me give you a different email address, one that nobody else has access to. And if you think of me while you're at home, I'd love to get more pictures."

She smiled, "I'd like that. Nothing obscene or tasteless of course. I'm thinking 'Playboy'."

"I wouldn't say 'no' to tasteless. I'm thinking 'Hustler'."

She laughed.

Over the next few weeks, I was checking my secret email multiple times a day, but she only sent me a pic every now and then. She understood the erotica of suspense. One pic in a bubble bath, my first glimpse at her nipples floating above the waterline. One in a yoga pose in her panties, and I could see the mound of her pussy through the white silk. One in the mirror, showing her tattoo. One topless frontal, where I fell in love with one particular mole, on the lower side of her right breast. I wondered how many other men had seen these photos. I pretended they were all just for me.

I started dreaming about her. There was one dream where we were in the big back seat of an old luxury car in the dark, her head in my lap and her skirt lifted up, and I was fingering her and she was moaning, my wet fingers making sticky sounds as I circled her clit and slid in and out of her. Her shivering when she came so gently. There was another dream where I was following her into her room, and she was taking off her clothes and throwing them aside as she walked, fully naked in the room, turning around to kiss me. And a dream where we were getting a couples massage, to completion, and deft, oiled hands getting both of us off at the same time, me hearing her cumming as I shot into harm hands. I was obsessed, day and night.

I ran into her once at a conference. She was working the crowd in the hallway, in a yellow sun dress. Very casual for this kind of thing but clinging to her in the way she wanted. As we chatted, she admitted, "I love wearing dresses. I never wear any panties when I wear a dress, and it keeps me so excited around all these men in their suits and ties. If I get any wetter I might need to go to the ladies' room." She took my hand then, and squeezed it, and that's when we both became certain we would fuck. But not yet.

At our fifth monthly meeting, she met me in my office, and she was upset. She just stood there and burst into tears. The money she had set aside to start the business went missing, and she knew it was her business partner, a lady who was handling all the finances. I came to her and wrapped her in my arms, and she sobbed on my shoulder. I comforted her, my nose in her hair, her perfume engulfing me, her breasts pressed into my chest. She stopped sobbing then, and we kept holding each other. I was getting hard. She felt it between us and shifted her weight from side to side, slowly, rolling her belly across my dick. My nose went deeper into her hair, and I kissed her neck. She was breathing in my ear, little panting sounds, but then she whispered, "I really have to go." And she did.

All this to say, after six months, Janet met me in my office. As I walked her to my car for lunch, Pam had a look on her face as we passed by her desk, like she knew something I didn't. Janet was wearing a short dress, and I suspected she didn't have anything on beneath it. We were unusually quiet on the way to the restaurant. She seemed nervous.

When we got to our table, I told her about my dreams. She licked her lips, and her eyes were wide in the dim light. I asked her, "Do you ever dream about me?"

"No," she said, "but I fantasize about you."

"Tell me."

"You lead me into the bedroom and make me strip. You make me place my hands on the bed and you start spanking me, so hard, and I'm cussing you, but I get so wet, and you reach between my legs and I'm ashamed at how wet I am but it pleases you and you just spank me more, and harder, until my knees buckle. Then you force me on my knees and you leave the room for a while. When you come back, you unbuckle your belt and your hard cock is in my face, and I suck it, and you cum in my mouth, and I swallow it all. And then you throw me on the bed and eat my dripping pussy until I cum, and until you are hard again, and then you fuck me bareback, and I beg you to put a baby in me." She said all this in one continuous stream, looking down at the table.

"Look at me," I said. Knowing now how much she wanted to be dominated. She looked up into my eyes, lips parted, deep excited breathing.

"There's something you've been holding back in the pictures you sent me."

"I know."

"Show me." I knew by now that she must have the photo I was waiting to see.

She pulled out her phone, and with just a few swipes, she handed it to me. A photo of her shaved pussy, her fingers lightly holding the lips apart to show the bright pink inside.

"Send that to me."

"Yes, Sir."

We finished eating and got in my car. She sat with her legs together, her dress half-way up the thigh. I got out on the highway and sped up. Her legs moved slightly apart. Then she said, "That first time in your car, I got so wet I was afraid you could smell me."

That's all the encouragement I needed. I swerved into the left lane and opened it up.

"Oh my God," she said.

All I said was, "Show me."

She lifted her dress above her hips and spread her legs. I reached across with my right hand, the car now over ninety miles an hour. Her pussy was soaking. I slipped my fingers inside her and pressed the gas farther. We were doing one hundred and thirty-five when she grabbed my wrist with both hands and pressed my hand down on her clit and started to cum. We were doing one fifty when she stopped. I took my foot off the gas and took another three miles to slow down to the speed limit. I left my fingers in her, and she came again on the way down.

When we turned back towards the city, and finally into the parking lot, her bare pussy was still exposed, pink and wet.

"Spread your legs wider," and she did. I put my wet fingers in her mouth, and reached across and put my other hand inside her pussy, her fucking her with it. There were people in the parking lot, but none right beside us. She came for me again, right there, and now both of my hands were wet, but her crotch was soaked.

I didn't wipe my hands. I pulled her dress down, and went around to let her out, not so elegant this time, shaken, shaking. She walked behind me to my office. We passed Pam's desk, and Janet shut the door.

I had my script from Janet's fantasy. I told her to strip and put her hands on my conference table. Her jaw dropped, knowing Pam would be able to hear us. But she obeyed.

I spanked her with my bare hand. She winced at the first one, 'ouch' at the second, then the cussing started and didn't stop for the next twenty strokes. Tears were flowing down her face, but pussy juice was flowing down her legs.

"Pick a number," I said.

"Twenty more," she said, sobbing.

Her legs buckled after ten, and I stopped. I reached between her legs, grabbed her pussy and shook it and juices slung everywhere. I wiped my hand on her red ass. Then I forced her onto her knees on my carpet, and I left the room.

Pam watched me come out my door and watched me shut the door again. I pulled up a chair beside her.

"How is the meeting going?" she asked.

"It got a little heated," I said.

"Sounds like you have it all in hand."

"Yes, I do." Then I sat there and checked my phone. I found the picture Janet sent me of her pussy. I was staring at it, and made no attempt to hid it from Pam.

I took about ten minutes with Pam before I stood up again to head back inside my office.

Pam said, "Don't feel like you have to shut the door."

So, I left it open. From where Pam was sitting, she couldn't see Janet kneeling on the floor. So, I stood nearer the door.

"Come here," and Janet crawled over to me. She looked out the door at Pam as I unbuckled my belt. I doubled it and kept it in my right hand and Janet pulled down my boxers. As she took me in her mouth, I swatted her red ass with the belt. She jumped, and instinctively moved her hand to her bottom.

"Keep your hands on me," I said, and she did. She cupped my balls with one and stroked the staff with the other. I only spanked her a couple more times, to keep her tight, as she sucked me. She was moaning, and the vibration in her throat felt so good on my cock. As she sucked my balls, I watched Pam, who could see my stiff, wet cock above Janet's face.

I was ready to finish off, but not in Janet's mouth. I broke script and grabbed her hair, lifting her up to her feet. Then I turned and pushed her against the wall where Pam could still watch, and I lifted her by the hips and fucked her there.

She was loud. So much so that Pam got up and shut and locked the outer door. Then Pam came and stood in my doorway to watch more closely.

"Please cum inside me."

"I'm going to put a baby in you, right now."

"YES. God. Please. Please breed me!"

I couldn't wait any longer. I came hard in her, pulsing and throbbing, driving my semen deep in her womb.

When we were done, I stepped away from her and she slumped to the floor. I put my dick back in my pants and put my belt back on. Pam helped pull Janet together, straightened her dress and her hair, and escorted her out of the office.

My only regrets were never tasting Janet's sweet pink pussy, and never cumming in her mouth. I figured I would do that next time. But there was no next time.

One month later, I looked at my calendar and there was no appointment. I logged into Facebook that morning and saw Janet's profile picture was of her and some Marine in uniform.

I moped into the office that day, and barely spoke to Pam as I went into my office and shut the door. All I said was, "Hold my calls today."

I checked my email a few times that morning, and my private email, but no word from Janet. I didn't call or text her, but I was really bummed out.

Just before lunch, Pam walked in my office without knocking. She put a stack of papers on my desk, bending nicely and giving me a glance at her bra, and normally that would have perked me up.

When it didn't, she gave me a disapproving look, walked out into her office and I heard the main door shut and lock.

She came back to my desk and said, "Take off your pants."

Shocked, I started to stand up, but she put her hand on my shoulder and kept me in my chair. I scooted out of my pants and boxers. It all happened so fast, my dick was still soft, but waking up fast.

Pam took her top off and her bra. Her breasts were big and lovely, and I confirmed my suspicion that they were tanned all the way to her nipples. She put her left nipple in my mouth and reached down to my dick with her right hand and started stroking me. I was hard in an instant. She kept up the hand job and I began to throb. Before I went so far as to make a mess all over my chair and her, she reached across my desk and emptied some pens out of a coffee cup and pulled the head of my dick down and into the cup. Then she went all out stroking me hard and fast as I came into the cup.

After I was done, she pulled her breast from my face and took the cup with her as she left my office and shut the door.

I sat there for hours after that, thinking about her, until she came back in the door and said, "I'm leaving early today. Do you need anything before I go?"

"No, thank you, Pam. But tomorrow..."

"I know what you need," she said. "Have a good night."

When I left for the day, I walked past Pam's desk and my coffee cup was there, with lipstick on the rim, and a used teabag on a tissue beside it. I wasn't sure, but i imagined my sperm in Pam's belly, having flavored the tea.

I went home and fucked my wife hard that night. Hard enough that she got suspicious, but she didn't spoil it by accusing me of anything.

And when I dreamed, that night, it wasn't of Janet.