Secretary Extraordinaire Ch. 03

Story Info
A boss takes a well deserved vacation.
4k words
4.52
70.9k
7

Part 3 of the 5 part series

Updated 09/22/2022
Created 12/21/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
pbidude
pbidude
55 Followers

It was nearing Christmas time, and like every company, there was going to be a party in my office this year. All of the employees meet in the main cafeteria to hear a message from the CEO and receive little door prizes; then each floor hosts their own private party back in their conference rooms. It's usually a great time for everyone and aside from three years ago when John from accounting got drunk and started hitting on the CFO's wife, everyone usually is pretty tame. This year, however, I was not looking forward to the party.

I've been screwing my secretary, and everyone will know it the second we walk in together. Wait, we can't go together, then they'll know for sure. But I can't make her go alone, that wouldn't be fair. Of course, people will wonder why neither one of us have a date if we don't bring one. My mind raced though a hundred different scenarios, all of them ending in either Jennifer being upset, or everyone finding out about us. Let me back up a minute. I wasn't just screwing my secretary; that would have been just creepy and a bit wrong. I was dating her secretly, though, and our relationship had grown from a purely sexual escapade in my office just three months ago. Since then it had blossomed into something exciting, something great. I was totally in love with her, and that was something I could not wrap my brain around. I hadn't felt this way about a woman since my wife had died a few years ago; taken from me in a tragic plane crash while we had been flying home to see her family one Labor Day weekend. I lived, she died. Life was cruel sometimes, but maybe Jennifer was my second chance at happiness.

Oh, if only I didn't feel like a badly written character in a sexual-tension based sitcom, having to choose between multiple bad decisions when the answer was so clear to the audience. It wasn't a strict company policy that employees couldn't date. It was, however, a very big problem for a boss to date his direct subordinates. Someone from another department would have been fine, maybe even someone from my department if they had been far enough below me in the corporate ladder, but not my direct subordinate. No, my secretary was, for all intents and purposes, completely off-limits. One mid-level manager had been sleeping with his assistant several years back, and they fired him so quickly, many of us looked around for a trap door they may have dropped him through.

"Mr. Davies?" I blinked several times, and adjusted my eyes toward the voice that had pulled me from deep in thought. It was the interoffice courier. An intern of about 19, he looked like he was wearing his father's only suit, and had a mismatched tie to complete the ensemble.Poor Kid, I thought, he'd better learn a lot while he's here, or the business world is going to eat him alive. I beckoned for him to come in, and he slowly stepped the few feet to my desk.

"Sir, this is from Mr. Archer. He said to deliver it to you personally." James Archer was the CEO, anything directly from him was important.

"Thanks, I appreciate that. You can just leave it here on the desk." He dropped the envelope, scuttled out of the office, and jumped directly onto the elevator.

I opened the envelope. Inside was just a simple letter, hand-written on his stationary.

"Michael, Mary and I would love for you to join us in Montana this year at our cottage. Bring a guest if you would like (I already know about her, but only a few people do. It's not a big deal, so bring her if you wish to.). The jet is leaving from here about an hour after the party is winding down, so we'll just have a car ready for you then. Good job this year, I'm happy we've put you in your position."

Holy Shit! My mind raced with possibilities. How could he have found out? I sat there staring at the note for about five minutes, when it finally dawned on me.It doesn't matter how he knows, he does and he's not pissed off. That's probably not an invitation to flaunt it around town, but at least I won't get fired.

Today was Tuesday, and the party was going to be Friday night. I had a lot of work to finish up if I was going to be out of town. I had decided not to tell Jennifer, because I thought that the surprise would be more fun. Instead, I called her roommate, Denise, and asked her to pack some of Jen's cold weather clothes in a duffel bag so I could pick them up later. She was happy to oblige, and promised to keep the secret.

Thursday morning I walked into work, and Jen was already getting things ready for the end of the year. Filing and separating different documents, and preparing others for my signature. She smiled at me as I walked past her into my office. We both went about our day until just before noon, when she sauntered into my area.

"Hey, Mike. I've got to go shopping on my lunch break for a few things, do you need anything?"

I had a wicked grin cross my face, then immediately went back to normal. If she noticed, she didn't give an indication. "Actually yes," I said, reaching back into my pants for my wallet. "Take the rest of the afternoon off, go to the department store, and buy yourself a new dress for tomorrow night. Take my credit card. And while you're at it, why don't you pick up some new lingerie for this weekend? I have a feeling you might need it."

Her eyes twinkled a little bit, subtly reflecting the excitement and anticipation she must be feeling. "Are we doing something special this weekend?"

"Yeah, I thought we could go rent a place on the beach, just you and me. Make a real holiday out of it."

"Ooooh, that sounds wonderful. I didn't really want to go see my parents anyway. They're always getting on my case about working too hard and not finding the right man. I guess they don't really know what they want for me." She took the card from my outstretched hand. "Ok, I'll see you tomorrow then. I won't show you the dress until the party; make it more of a surprise for you."

Friday morning dragged on for so long, I felt like a kid on Christmas Eve, waiting on Santa to come. I knew I was getting a present tonight, but I couldn't wait to unwrap it. Jennifer had her typical business attire on, and even thought she still looked amazing, it wasn't anything spectacularly special. She did have a garment bag on the hook behind her desk, but it was completely opaque, and I couldn't see what was inside. Three O'clock and the waiting was finally over. I went back into my bathroom to put on my tuxedo. After several minutes of wondering why in the hell people still wore those stupid things, I emerged victorious and stepped back into my office. I was stopped by my lover, carrying her garment bag over her shoulder, and what looked like a makeup bag in her hand.

"Wait for me, sweetie?" She asked, looking ever so coy.

"Why not, I'm dying to see what you've got for me to unwrap later." She laughed, and pushed past me into the bathroom. I heard the water in the shower running, so I knew I was in for the long wait of the typical woman.

I settled back to my computer to watch some videos of people doing stupid things (always a favorite pastime), and I checked on the bags I had packed for us. An intern was going to come up and get them during the party to take them down to the car for us. When I heard the blow drier finally stop, I looked at my watch for the first time.Only forty-five minutes, that's not terrible.

About five minutes later, I heard the door handle jiggling in place, and my eyes turned toward the inner part of my spacious office. Then the door swung open, and a vision of pure beauty practically blinded me.

She had her brilliant red hair up in a twist, with two small strands from her forehead perfectly framing her delicate face. Her small white earlobes hung a little lower with heavy pearl earrings, a gift I had given her as part of a set. The necklace graced her fluid lines, as most of the dark green dress she had bought left her shoulders exposed. Save for two thin spaghetti straps, they were completely bare. The freckles above her breasts next caught my attention, as the plunging neckline went from the straps on he shoulders, through her perfectly shaped cleavage, and almost down to her belly button. The lines of this magnificent dress accentuated her hips better than anything I had ever seen her wear, and even though it extended to her ankles, the side slit went well north of her knees. Three inch heels that undoubtedly put me back quite a few bucks graced her feet. I sat staring, my mouth open, for what seemed like an eternity. I was one lucky bastard. I think I would have stared for the rest of the night had she not walked over to me and given me a deep, thoughtful kiss. The kiss was electric for me, with feelings I couldn't describe flowing through me as I kept right on staring through my mind's eye.

She broke the kiss slowly, and stepped back. "You like?"

"Uh, uh, yeah, you could say that." She laughed as I paused, trying to form words into sentences. "Jen, you are the most beautiful woman I have ever seen in my life. You look truly amazing."

"Well, thank you. You just wait until you see what else I bought. Now come on, let's go dancing."

She took my by the arm and we went down to the party together. Most of the guests had had plenty of time to get liquored up by then, so I doubt many noticed us coming in together. After congratulating most of my team on a job well done, kissing a little ass, and having a few glasses of spiked punch myself, I turned to Jennifer, whispering in her ear.

"We'd better get going if we want to get there on time. Say your goodbyes, and then meet me in the main lobby in ten minutes." She nodded almost imperceptibly, and walked away from me without looking in my direction. A casual observer would never have known what was really going through her head.

Eight and a half minutes later, she came up behind me in the main lobby.

"Ready for a weekend you'll never forget?" She asked.

"Are you? Because I think you'll find this trip even more memorable than you may currently imagine."

I took her hand and led her outside to the limo waiting on us. I opened the back door for her, as a look of surprise flashed on her face.

"Fancy. You've really outdone yourself. You just may get lucky tonight." She winked at me, and then lowered herself into the car. As I walked to the other side, I laughed to myself that this was going to be a big surprise.

The limo was closed up and ready and the driver began our short journey to the local general aviation airport. When I raised the privacy shield, Jennifer jumped on me, hiking up her dress and straddling my lap. Flinging her hands around my neck, she leaned in a kissed me passionately. Our lips met with force, and my breath was removed from my body for a brief second. I could taste her lipstick as my tongue moved into her mouth, massaging hers with gentle rhythm. Her hands rubbed the back of my neck, as mine moved around her waist to her firm buttocks. I squeezed her closer to me as I kissed her again, our libidos rising together. But she took her hands away from my neck and moved them onto my own. She took my hands, and placed them up above my head, whispering: "Keep them there."

I wasn't one to argue with a beautiful woman, and when she saw my hands weren't moving, she looked at me with lust. "You got me a present with this little trip, now you get a present, too."

She reached down and unzipped my trousers. Unbuttoning the top, she pulled them down to my knees, bringing my boxers with them. My half-hard cock now lay exposed to the dark interior of the car. With her left hand, she reached under my balls, and began gently rubbing them in circles with her fingers. Her right went onto my shaft, trying to coax it to life. As I saw her again with that look in her eyes and especially with her hand on my dick, I sprang into fullness. Pleased at her efforts, she lowered her head to the top of my penis. The head quivered in anticipation of what was coming next. Kissing the tip, she licked off the small drop of pre-cum that had begun to form. Still stroking my balls with her left hand, she now moved her right to my thighs, rubbing up and down each one as she slowly moved her mouth farther down my rock hard pole. Slurping as her head moved back up, she began bobbing her head up and down on my cock, increasing and decreasing the pressure of her lips and tongue. Harder then softer, faster, then slower, she kept sucking on my dick until I was ready to explode. Then she reached her right hand back between my balls and my asshole, and gently pushed on that soft piece of skin as she sucked the tip and stroked the shaft. I lost all control. An instantaneous wave of pleasure started in my head, and flowed through my body down to my feet, curling my toes. The wave traveled back up my legs, through my cock, and crashed into Jen's mouth as a wave of cum entered her throat. She dutifully kept sucking until I was empty, and then swallowed the load down with ease.

She licked her lips, and smiled up at me. "Wow, you haven't come like that in a while. I guess I really do look that good."

I grabbed her, and pulled her close to me, kissing her again. "My dear, I said it before, I'll say it again: You look amazing. But we need to get dressed, we're almost there."

"What? We've only been driving for about 15 minutes. How can we be there?"

"Ok, I lied about the destination. We're not going to the beach." Just then I heard the squeak of the limo's brakes signaling the end of our ride.

"Well, then where ARE we going?" The limo driver opened the door, and I stepped out, turning to help her out as well. About ten feet away stood the boarding step to the company Falcon 900B, a large cabin, long range business jet. Her jaw dropped.

"Well, as a special gift to me, you and I are going to take this jet to Montana, for a weekend of skiing and hot tubs at James Archer's cottage. Sound like fun?"

"Oh, HELL yes. I mean, yes. But I didn't pack any warm clothes."

"That's okay too. I had Denise drop off some winter clothes earlier this week when I found out about the trip. Here's your bag now." The driver dropped our bags by the luggage door to the plane. The co-pilot was standing there loading everyone's skis and luggage into the cargo hold. I tipped the driver, and turned back to Jen, gesturing up the stairs. "After you."

She took each step slowly, and I realized she'd likely never been on a private jet before. "It's okay, you won't break them." I tried to be re-assuring. She reached the top stair, and began walking down the aisle toward the rear. It was then that we both saw James and Mary Archer already seated, and with drinks in their hands.

James is not much older than I am, a man of about forty-five. He started this company in college, and has grown it to be a gigantic multi-national corporation. He met Mary when he was just starting out, before he made his millions, so she's not the typical CEO's wife. Not that she's unattractive; she works out regularly, and takes excellent care of her body. Slightly younger than James, she's roughly 5'5", and probably only weighs 130 lbs. With long blonde hair and bright blue eyes, she's very pretty. Her B-cup tits don't sag, despite having nursed two children, so maybe she'd had a little work done here and there. Overall, she was hot.

"Good evening Mr. Archer." I could tell Jennifer was slightly uncomfortable around someone much higher than her on the corporate ladder.

"Hello Jennifer. This week, you can call me Jim. Have you met my wife Mary?" He extended his hand and Jen shook it, and then did the same for his wife.

"No, it's nice to meet you Mary. Thank you both for inviting me here."

"It was our pleasure. You're new boyfriend has been working too hard. We decided to give him a break."

Jen blushed at that remark, and there was an uncomfortable silence. Jim spoke again.

"Can we get you anything to drink? Champagne?"

Jen nodded. "That would be lovely."

Jim looked back over his shoulder. "April? Two more Champagnes, please."

April was the corporate flight attendant. A slender woman in her mid-thirties, we always flirted whenever I flew on the jet. She was happily married, but she was always pleasant, and reveled in being able to still command any man's attention. She brought out two more glasses, filled them from the bottle that sat cooling in the table, then walked toward the cockpit. When she had finished speaking with the two pilots, she went back and closed the door to the aircraft, checking to be sure that the limo had pulled away, and the carpet had been moved. When she walked back toward us, we were happily sipping the bubbly, and making small talk. "The captain says we're ready to go, sir. Flight time should be about 2 hours and 45 minutes. I ordered dinner for everyone; if you're hungry I'll serve it in about an hour."

"That's fine April, thank you."

"Okay, is everyone buckled in?" She looked at our laps to check for seatbelts. "Good, I'll be in the galley if you need me."

The flight was long, and with the exception of dinner, rather uneventful. We landed at an airport about an hour's drive from Jim's cottage, and from there we took another limo to his house. As we gathered our things and stepped into the house, Mary looked at us both.

"You two are upstairs on the left. That's the second suite. The other bedroom is still a mess, so don't go in there. The hot tub's out on the covered patio, so help yourself. Breakfast is at 8:00, and the slopes open at 10:00. We're going to bed now, but make yourselves at home, and don't feel like you have to on our account."

We thanked her, and I carried our bags up to the upstairs suite. When we had finally unpacked, we were both so exhausted that we fell asleep on top of the bed sheets.

Waking up early the next morning, we had a hearty breakfast and then the four of us headed off to the mountain to ski. Jen and I separated from the others, and we skied together for a few hours. Lunchtime came and went, and I decided to go to the top to ski the black diamond. Jen said she would ski the bunny trail, and we would meet at the bottom. As the day wore on, we both wore out, and decided it would be good to take a long hot soak in the hot tub back at the cottage. We caught a lift from the mountain shuttle, and soon enough we were back at the house.

I tore off my boots and breathed a sigh of relief. Jen had hers off too, and we proceeded toward the enclosed patio where the tub was. After a short search, I found the controls, and turned on the jets. Someone must have turned the heater on before we arrived, because the water was already at peak temperature. I shed my jacket and snow pants, leaving me standing in long underwear, and realizing I looked somewhat silly. Jen was wearing spandex underneath, and from what I was looking at, nothing else. In the chilly air, her small round nipples poked at the fabric. She caught me looking at her breasts.

"I guess I'll go change into my bikini."

"Oh, no, house rule is no swimsuits." She grinned and peeled off her top, exposing my favorite breasts in the world. A nice handful of small C cup surrounded soft pink nipples that were wonderfully erect. Her leggings fell next, and the sight of her completely shaved pussy made my dick jump up and ready. I pulled my shirt over my head, and quickly dispensed with the bottoms as well.

"My, my, I guess my nipples aren't the only things that get erect with the weather around here." She came over to me, grabbed my cock in her hand, and led me to the water. "Let's warm this poor guy up a little bit."

The water was hot, but not too hot to prevent me from getting in all the way. Jen came behind me, sitting directly in front of me. She placed my hands on her shoulders, her universal signal that she wanted a neck rub. I obliged, and soon she was moaning from the tension being released in her shoulders. She bent her neck back to kiss me, and I dropped my hands to her tits. She moaned louder at this. Then she began kissing me harder, writhing her body and putting her hands on top of mine. She helped me to rub her tits, and brought one of my hands down to her clit. I could feel the jet of water that was exciting her. I did my best to match the sensation with my fingers as the jet pulsed hot water at her pleasure button. She screamed in orgasm after just a short minute of both stimulations.

pbidude
pbidude
55 Followers
12