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The Boss's Secretary

"More than just a pretty face"

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Author's Notes

"50% fact, 50% fantasy."

It was the mid-1980s and I was a hot-shot salesman working in Orange County, south of Los Angeles. I had moved from one territory to the next to the next, each time getting a bump in salary and getting an area with more volume in sales.

The work was simple, sell wine displays to the managers of chain grocery stores (Safeway, Vons, Albertsons, etc), keep them up to date on upcoming ad specials so they had plenty of inventory, and supply them with point-of-sale marketing material. It was a step above the typical route sales to retail as the company was known as one of the best for sales training. It was common to get weekly unsolicited voicemails from a headhunter gauging our interest in new jobs.

One week after our team meeting, my district manager pulled me aside and told me that our area manager wanted to talk to me in person that afternoon and I needed to be at the main office by 3:00 pm. When I asked what it was about Chuck said it was “a unique opportunity.”

I left our meeting and went about my day and arrived at the main office a few minutes early. Upon entering the office, the receptionist directed me to Mr. Denny’s office. I was a bit puzzled as I walked down the hall as Mr. Denny was the “big cheese,” the VP of Sales for the entire company, not just the Los Angeles company-owned distributorship.

Upon entering the outer office, I saw several other salesmen that I knew so I relaxed a bit. Charlene, Mr. Denny’s assistant, greeted me and told me to take a seat with the others and our meeting would start soon.

As the other guys and I whispered, we all were trying to figure out what was going on, and why were we all called to the main office. Another guy said his manager said it was a transfer opportunity. Another said he heard we all were hand-picked for our sales skills.

Charlene soon told us to follow her to the conference room where we found several upper management men and Mr. Denny. The opportunity was very straightforward. The company was taking over its distribution rights for Seattle and King County and would expand the company-owned Tacoma distributorship. They needed trained salespeople to hit the ground running to get a big push into the retail stores as the previous distributorship had done a poor job. We all had twenty-four hours to make our decision if we wanted to move to the Seattle area. The one difference would be that we’d also be calling on independent small “Mom and Pop” liquor stores on top of the chain stores. This would be new for all of us, and a new experience that would add value to our resume as we tried to climb any corporate ladder.

As I left the building, I was ninety percent sure I’d take the job in Seattle. I did not like living in Orange County the previous year and thought moving out of state sounded like a great adventure. I spoke with my father that evening and we discussed the pros and cons. When I hung up the phone, I decided to make the move.

In the morning I started calling on my accounts as usual at 7:00 am and after the first store, I found a pay phone and called the main office and told my area manager my decision. He told me to come straight to the office and see Charlene.

Charlene oversaw all of the corporate travel for the LA office, and she booked me on a flight the following morning up to Seattle, booked a hotel near the Tacoma office, a rental car, and a return flight on Friday afternoon.

When I arrived at LAX the next morning and was checking in, I ran into Mr. Denny at the United Airlines counter. After we exchanged pleasantries he told me, “Yes, Charlene said we’re booked together on this flight. We’re sitting next to each other she said.”

I had a lump in my throat. I’m going to be sitting next to the big cheese for two-plus hours flying up to Seattle. What the fuck are we going to talk about I wondered. Thankfully it was a pleasant and short conversation as he asked about my upbringing, family, college, etc. I read the newspaper while he flipped through various reports.

Long story short, I made the trip to Seattle, met my new district manager, found an apartment near my new sales territory, and returned to Orange County to have Bekins move my stuff. My time in Seattle was wonderful and I was doing much better than my colleagues. Unfortunately, the experiment of bringing in outsiders upset a lot of retailers and they were hesitant to buy from non-Washington people.

In mid-November, the company decided to abandon its expansion plan and would sell its brand rights to another distributor. I was called to a meeting in Tacoma where I saw the same faces from LA, including Mr. Denny.

“Rocky, how are you?” asked Denny.

“Great Mr. D. So nice to see you again,” I said.

Denny went on to explain to the other upper management guys how we flew from LA to Seattle together back in June. They all flipped pages and started whispering to each other. My Seattle area manager said, “He’s my best guy.”

Denny stopped the conversation. “Rocky, you’ve done a great job here in Seattle and are a valued employee. You have three choices. One, stay in Seattle and go to work for the new distributor at the same pay. Two, move to the Bay Area and we’ll find you a territory. Or, three, move back to LA and Orange County where you’ll be promoted to a Sales Trainer. Whaddya think?”

“Orange County and the promotion to Sales Trainer, sir,” I said confidently.

“Great,” said Denny. “Give Charlene a call and get booked on a flight and she’ll take care of the rest.”

It was a whirlwind of flying back to OC, getting another apartment, etc. I made several trips into the main office and each time had a chance to deal with Charlene turning in my expense reports and receipts. Believe me when I say that every single guy in the company enjoyed every encounter with Charlene.

She was extremely attractive. She was divorced, thirty-eight, tall, curvy, with long blonde hair and blue eyes. She also had one son, about age ten I’d guess from the picture on her desk. She had a degree from UCLA and was very sharp in her role as Denny’s assistant and taking care of all of LA’s corporate travel needs.

Once I finally got all moved back to OC it was the first week of December. Now that I was officially in “Management” as a sales trainer, I was invited to the Sales Divisions Holiday Party. It was centrally booked at a hotel in Manhattan Beach. I opted to take advantage of the discounted room prices and secured a room versus driving the hour back to Irvine after drinking.

The following week I went to the holiday party unsure of what to expect. I arrived to the hotel early and checked into my hotel room. As I walked down the hall towards my room a door opened and out walked Charlene.

"Hi Rocky! Are we neighbors tonight?” she joked.

“I guess so. I must be a few doors down in 419,” I said.

“I’m on my way down to double-check on things. The party starts in an hour. See you soon,” she said as she walked down the hall.

The scent of her perfume filled the hall. I took an extra deep breath after she walked past me. I couldn’t resist myself, I turned to watch her walk down the hall in her above-the-knee red cocktail dress. As I did, she looked over her shoulder catching me in the act. She smiled and waved.

The party was about what I expected: mediocre banquet food, a no-host bar, multiple bottles of wine on the tables, and most of the attendees had a plus-one. A group of us single guys ended up at a table along with two women from the On-Sale restaurant and bar division.

When the dancing started, I figured I’d walk the few blocks to downtown Manhattan Beach to hit a few bars. As I said good night to a few people Mr. Denny waved at me from his table of executives. I took the opportunity to say hello, and meet his wife, and a few of the other men and their wives. A little “schmoozing” couldn’t hurt I reasoned. The lone single person at the table was Charlene.

“Char, I really want to thank you for helping me with moving back from Seattle,” I told her.

Before she could answer, Mr. Abate said, “Rocky, why don’t you dance a few songs with Charlene before you young guys head downtown.”

I was a bit stunned he’d ask me to dance with Char, but in the split second I smiled and looked at Char, “It would be my honor. Charlene, would like to dance with me?”

She laughed, “I guess Peter (Mr. Abate) thinks I need to be entertained tonight. But, yes, I’d love to dance a few songs.”

I held out my hand and the next thing I knew we were on the dance floor as the DJ played some new wave song I’d heard on the radio a few times. The third song was a ballad. I looked at Char and asked, “Would you like to  slow dance?”

She smiled and stepped up as I wrapped my arms around her slender waist. We started to chat a bit and she indicated she was heading to her room soon. “Why don’t you join me and we’ll walk downtown to a few of the beach bars,” I said.

“I’m a bit old for those bars, I’d be the oldest woman there” she mussed. “And I have a ten-year-old at home.”

“But you’re spending the night here, right?” I asked.

“Yes, my son is with his father this weekend,” Char whispered in my ear.

Between the booze, her sexy dress, and her whispering in my ear I could feel my manhood swell in my slacks. I tried to stay focused on the slow dancing but as we swayed my cock was getting rubbed by her body. I tried to change the motion but she was having none of it.

“What’s the matter, Rocky? Is something hard?” she said with a mischievous grin.

“Uh, you were rubbing against me,” I stammered as I blushed.

“Yes, I know. That was on purpose.”

As I tried to stumble over my next sentence Charlene cut me off.

“I’m heading up to my room. You go up in fifteen minutes. I’ll be down to your room about 10:30 pm,” she said.

I looked at my watch, it was just minutes after the top of the hour.

“And one more thing. You cannot tell anyone about tonight.”

“Oh, of course not,” I said as I envisioned myself fucking this hot blonde.

“I know you won’t because I will get you fired if I hear you talk.”

Promptly at 10:30 pm, there was a knock on my door. For some reason, I looked through the peephole to see who it was. I opened the door and in rushed Charlene.

“Hurry up, I don’t want anyone to see me coming into your room,” she said. “Management, and especially Mr. Denny, would not be pleased to know I was in a junior manager’s room.”

“Would Mr. D fire you?” I asked.

“Doubtful, he’s my uncle,” Char told me.

“What? You’re kidding? Maybe we shouldn’t do this,” I said.

Laughing, “It’s fine. It’s my personal life. They just would not think it’s kosher, so to speak,” she said.

It was then that I finally noticed she was holding two bottles of wine. “I don’t think there’s a bottle opener in the room,” I told her.

“You work for the world’s largest winery and you don’t carry a bottle opener when you travel? Rule number one: always carry one. You never know when you’ll need to open wine or a bottle of beer. Here,” she said handing me a small collapsible combination corkscrew and bottle opener.”

“Wow, that’s nice and small. Perfect for traveling,” I said.

“You’re young. You’ll learn,” she giggled. “Now open that Cab.”

As I fumbled with the bottle of wine and poured us each a glass Char started asking a bunch of personal questions. “Have you ever been with an older woman?”

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“Yes. Just two years ago. She was about forty,” I said.

“OK. Older women know what we want in bed. And I won’t be afraid to tell you what to do, so don’t take it personally. It’s all for my personal pleasure. Do you understand?” she asked.

“Yes, I understand. Just so you know, my college girlfriend taught me how to eat pussy. When we’re done you’ll want to send her a thank you note,” I said with a devilish grin.

“OK, Rocky. Hopefully, you live up your advertising,” Char said.

We sat on the loveseat to share our wine and continue our chat. I learned she was born and raised in Redondo Beach, not far from where we were at the hotel. She attended UCLA where she was a cheerleader for three years. And, more importantly, Mr D’s wife and Char’s mother are twin sisters.

“Oh, wow,” I said. “Now that you mention it, I do see a resemblance to your aunt.”

“You should see my younger cousin; she and I look a lot alike. People think we’re sisters when we hang out together,” Char stated.

“Younger? How old? Single?” I asked.

“Too old for you Rocky, she’s thirty-five. And she has a boyfriend,” she laughed.

I leaned in and lightly kissed Char’s cheek several times before running more kisses down her neck.

“Shit, I love that!” she whispered.

I did it again. “Like that?”

“Yes, just like that,” she moaned.

I put down my wine on the coffee table and then grabbed hers and did the same. Shifting a bit on the seat I went in for a passionate kiss. My left hand went to the back of her neck as our lips met, mouths opened, and tongues danced. With my right hand, I went straight for her large left breast, softly rubbing her over her dress.

“You know, that will feel a lot better without my dress on. Undress me,” Char commanded as she stood.

I stood and spun her around, giving me access to the center zipper high on her back. I slowly, and playfully, pulled the zipper down, stopping twice to kiss her bare back. Her red lace bra was now exposed so I undid the clasp and pushed the shoulder straps down her arms. It fell to the floor.

I continued with the zipper, finally hitting her lower back or upper butt. I pushed the cocktail dress past her hips, and it too fell to the floor. Char stepped out of her dress and turned around. We were nearly eye to eye. Our lips had a gravitational pull like magnets, attracting each other as we kissed several times.

“My turn to undress you, Rocky,” she whispered.

I hoped it would happen quickly as my cock was aching to break free from my "tightie whitie" briefs. I sat down quickly to untie my mahogany wingtip shoes. I stood to unbuckle my belt when Char pushed my hand away. “I’ll do that.”

She held on to my torso as she slid down to her knees and began with my belt and slacks. When she pulled off my briefs my boner was at full erection. As I stepped out of my underwear, she joked with me, “You really need to upgrade to some Calvin Klien’s. These are little boy's underwear. And don’t buy white.”

She stood up and unbuttoned my shirt and it was soon on the floor with the rest of our clothes. I was buck naked, but Char was dressed just like how I enjoy my women, in nothing but thigh-high stockings and high heels. She looked like a Playboy centerfold that I’d masturbated to a thousand times as a high school-aged kid.

After making out for over ten minutes and allowing our hands to roam each other's bodies I kissed my way down her body, stopping briefly to lick and suck each breast. When I got down to her pussy I found a nice groomed patch of pubic hair.

Being 1987, she a small business card size of medium thick blonde pubes, and shaved everywhere else. She was by far the most trimmed woman I had been with at that time. I figured it was due to her age and living in LA.

Char was very sensitive and I had to go lightly on her labia and clit, but was very turned on to having two fingers in her honey pot. She was also highly orgasmic. Over twenty minutes she got off three times.

“I need a break,” she panted after the third orgasm. As we sipped some wine she told me, “Get me that girlfriend's address, I will send her that thank you card. Fuck, your tongue and mouth are amazing!”

Char’s resting time didn’t last long as she was soon stroking my cock as we lay on the bed and talked. She giggled and said, “Are you ready for this Rocky?”

She moved down the bed and got in between my legs and started to suck my manhood with expertise. I was soon moaning in pleasure and telling her how good it felt. As much as I wanted to shove her head down on my cock to have her deepthroat my thick seven inches I did not want to upset her and lose my chance to fuck this So Cal beach babe.

“I’m ready to fuck you,” I whispered.

“OK, but let’s sixty-nine a bit so I’m nice and wet,” Char said.

Who was I to turn down the boss’ secretary? Before I could say anything Char was throwing a leg over me and backing up her kitty toward my face. As I suspected, she was already wet enough for my cock to slide in, but after a minute of licking and sucking on her lady bits, she was flowing.

“How do you want it?” I asked.

Seductively, Char said, “I want you to take control and fuck me however you want.”

I flipped her off my stomach and onto her back. I mounted her waist, grabbed her two hands, and pinned her down. “Oh, I’ll fuck you how I want alright,” I snarled.

I let go of her arms and grabbed her legs, pushing them back by her head. Standing on my knees, I guided my rock hard cock to find her slippery love tunnel, and I slid into her tight pussy. Char moaned.

She instinctively wrapped her arms around her legs as they rested in the “V” of her elbows, pulling back her legs. One of my hands started rubbing a breast while the other went down to her pussy where my thumb started rubbing her clit in a circular motion.

“Oh fuck,” she moaned. “You’re going to make me cum if you keep doing that.”

“Good,” I said laughing. “You’re going to have to sleep here tonight because you’re not going to be able to walk down the hall.”

I started thrusting. And thrusting. I was now pounding Char as fast as I could from being on my knees. After several minutes I was starting to get winded so I told her we’d switch. “Ride me so I can suck on your delicious titties,” I told her.

As Char rode me, sitting tall in the saddle, I again took my thumb to her clit. “God damn you! Stop or I’ll cum again,” she pleaded. This time I did not stop.

“Oh, oh, oh…” she was yelling twenty seconds later. She leaned forward toward me, so I began sucking on her right boob. “Oh my god! Oh my god!”

I could feel Char’s pussy contract around my penis. As I was now thrusting upward I knew I wasn’t going to last long in her pussy vise. I moved my legs up a bit, resting my feet on the bed and was thrusting hard and deep into her pleasure palace. I warned her, “I’m going to cum. Should I pull out?” I asked since I was plowing her with no condom.

Between deep panting breaths, “Cum in me!” Char stammered.

As she climaxed and her kitty squeezed my dick like no other woman prior, I let out a neanderthal caveman grunt, “Aagggghhhh!” as I shot my load. Gusher after gusher of my baby batter filled her pussy as we both froze, enjoying our orgasms. “Holy shit,” I whispered. “That was fucking amazing.”

Char rose off my chest, her mascara running a bit, “When you sucked on my tit I lost it,” she chucked, also in a whisper. “I’m going to roll off.”

She dismounted my pink steel and hovered over me momentarily. I could feel our cum dripping from her cunt onto my pubic area. I would have loved to witness that river of white creamy spunk exiting her pink tunnel. This was decades before the term “cream pie” existed.

Char laid on my right side and I put my arm around her shoulder, leaned over, and kissed her passionately. “That was so much fun,” I told her.

“Yes, it was. And I really needed a good fucking. It’s been a long time,” she confided.

Without thinking I blurted out, “How long?”

“Too long. Almost two years,” Char told me.

“I can’t believe that. You’re so cute,” I said.

“It’s a personal choice. I have a kid. And so many guys are jerks,” she said.

I paused for a bit, thinking she say something else. Nothing. “So you haven’t dated since you got divorced?”

“I’ve dated a little. But it’s so hard with a child,” she said. “And I’m not a bar type of woman. It’s hard to meet good white-collar type men at my age.” She let out a deep sigh, “Let's talk about something else.”

I pulled Char closer to me and kissed her forehead. “You know you’re a catch, right? You’re beautiful, educated, solid job,” I said. “And amazing in bed.”

“Rocky, you’re so sweet,” she whispered. “And I have a ten-year-old son.”

I kissed her forehead again as we snuggled. While I was hoping for round two I soon heard Charlene lightly snoring. She was asleep. I pulled my arm out from under her, used the restroom, and pulled the blankets up over us as I climbed back into bed.

“Hey. Hey,” I heard. I woke up realizing I was spooning Char. Sunlight was squeezing into the room from around the hotel curtains.

“Good morning,” I whispered.

“What time is it,” she asked.

“No clue. The sun is up though. I’m going to pull my arm out from under you to turn around to see the clock,” I told her. “It’s only 7:36 am.”

“Ok, thanks,” she said in a sleepy mumble.

“Any plans today,” I asked.

“Not really. I have to be home by 5:00 pm when my son comes home,” she told me.

“I know a great place for breakfast down by the beach. Can I buy you brunch? Maybe take a walk down the pier?” I said.

Laughing, “I fuck your brains out last night and you’re taking me to The Kettle?”

“How do you know about The Kettle?” I laughed.

“Did you forget, I grew up next door in Redondo,” she said.

“It’s too early for me. Yes, I forgot,” I told her.

Two hours later we were sitting in The Kettle eating our brunch when in walked Mr. and Mrs. Denny.

“Let me do all the talking,” Charlene whispered. “Just go with it.”

Mrs. Denny saw us first and pulled her husband toward our booth. “Charlene, so nice to see you.”

“Good morning, Auntie,” she said. “It’s ok, Rocky knows I’m your niece,” she said looking at Mr. Denny.

“We ran into each other in the lobby, and he told me he knew a great breakfast place. How funny is that?” she said.

“Rocky,” said Mr. Denny, “living in Redondo her whole life I bet she’s eaten her a thousand times.” The banter continued for another minute until the hostess seated the Denny’s.

“So, do you still live in Redondo?” I asked.

“I do,” she admitted. “Shortly after my divorce, my parents retired to Palm Springs, so I bought their house. The house I grew up in. It’s only a block off the strand. My son is becoming a total surf rat.”

Charlene and I finished our meal, said goodbye to the Denny’s, and walked back to the hotel taking the long way along the beach strand.

As we said goodbye at her car, she thanked me for a wonderful night. “But remember, if I hear you talked, I’ll get my uncle to fire you,” she said in a serious tone. “Keep your mouth shut and I might invite you to my house in a few weeks when my son is with his father,” she said with a wink.

Seventeen days later, as I checked my company voicemail, I heard Char’s voice. “Saturday. 7 pm. Dinner at my house and bring your toothbrush.”

We saw each other for about four months. As I was leaving one Sunday in late April, I told her, “I think I’m falling in love with you.” The next evening she called me at home and said she thought it was best to stop our secret play dates. I cried myself to sleep that night.

The next day I sent Charlene a dozen red roses to the office. The card read, “I understand. Best Wishes, XOXO.”

The End

 

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Written by Taco4x4
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