My Legal Secretary

Story Info
Unexpected but long desired sex with secretary.
1.8k words
4.14
9.5k
4
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
673djp
673djp
77 Followers

I've enjoyed sex with both women and men. I love everything about sex. I also love my job. I've met many interesting people. Some of the people I've met I would definitely what to date and explore sexually. My profession as their attorney prevents me from pursuing people met through my business.

I was nearing the end of my career at the firm. My contact with my partners required us to renew every five years. Our firm is engaged in defense work. My practice is concentrated in automobile liability defense.

A new contact was set to be executed by January first of next year. It was now October first. We had a partners meeting. I advised I would not renew and retire. A decision was made regarding the reassignment of some of my cases. I agreed to conclude the others even if it meant staying beyond next January first.

My long time secretary Mandy was going to stay on at the firm. She was fifteen years younger than me. She is an excellent legal secretary.She has a beautiful face is tall, thin, long legs, large breasts tiny ass.

I have always respected Mandy is my secretary but I treated her as more my equal. So much so that our office plan provided considerable space for her directly alongside mine. she even has a window in her space, rare for a secretary.

We are both single. She'd had long term male friends. These relationships never ended in marriage. I too remained single. Sure I dated women, none seemed to be the right one. I also related to men. Being bisexual and as said, I've enjoyed sex with both women and men.

The insurance company our firm works for assigns lawsuits for defense. The assignment of a case within the firm is based on the exposure. Cases assigned to me generally involve policies up to ten million dollars, the maximum this insurance company offers. The company's insureds with large policies are usually high net worth individuals or businesses.

Now with two week until the end of the year, work has slowed as it does during the holiday season. A younger partner is taking over my cases. I'm looking forward to retirement. I will continue part time at another firm conducting legal training on a part time basis.

As always I take Mandy out for dinner during the holiday season, because it coincides with her December birthday we go to a very nice places. This year we are going to Piccolo Songno, an elegant Italian restaurant. We are going Friday evening after work.

Dinner was absolutely wonderful. The food was exceptional and the wine parings were perfect. We spent almost two hours enjoying the food, wine and ambience. We even met a fellow partner and his wife, they joined us for a nightcap at the bar.

As the evening ended, I called for an Uber black car. Mandy lives just north of downtown. Our driver took us to her condo, I walked here to her door and said good night. To my surprise she kissed me on the lips, said thanks for an unforgettable evening. The hired car then drove me to my destination my downtown condo.

Finally my last day arrived on December 30, the day before new year's eve. I'd removed all my personal property from my office over the last few weeks. I joined in the office farewell party. I received a Rolex watch from the firm. I also received a small wrapped box from Mandy. When she presented it to me she suggests that I open it at home.

After a long day I gathered my remaining items, I walked around the entire firm saying goodbye. My departure was both a sad and happy occasion for me. I have enough money to continue living well. My savings plus my pension and social security due me in a few years allows me significant income. I felt truly blessed and at peace with the world.

At home I changed and decided to have a cocktail then walk a few blocks to a favorite restaurant for dinner. Before leaving I decided to open the box from Mandy. I opened it and found a note and a key. A bit perplexed, I read the note. The note said in part, now that we no longer work together, use this key to my condo when ever you care to join me for the evening.

Shocked. I decided to call her assuming she'd be at home. I called, no answer, I did not leave a message on her phone. I finished my cocktail and headed out the door for dinner.

I walked into the bar at Quartino's, one of my favorite neighborhood restaurants. I usually sit at the bar. Dinner service is available at the bar. I suddenly did a double take, Mandy was sitting at the bar, near the door. I was surprised and I smiled and sat beside her. Saying hello we kissed I was incredibly glad to see her.

Dressed in all black, skirt, blouse, jacket and heels she looked beautiful. Her blouse was partially unbuttoned. Her pink chest was visible. I could see part of her breast too. This was so different from her office attire.

She spoke first saying she took a chance on my being at Quartino's tonight. I remarked that she knew my habits and that I generally ate here on Friday. She suggested a table and we moved to the table at the center of the bar.

We ordered drinks, red wine for her, a Jim Beam Manhattan for me. I ordered dinner a selection of small plate Italian specialties. The bar was getting crowded and a bit loud. We enjoyed the food and conversation about today and I offered her a ride home.

Calling an Uber black car we had the driver go directly to her house. I asked the driver to wait, but Mandy overruled me telling the driver I'd be staying. Her two bedroom two bathroom condo was very nicely furnished. Gray walls, gray wood floors with attractive contemporary furniture in shades of gray and blue. The kitchen was all white with relatively high end appliances.

Mandy offered a cocktail and I accepted asking for a Manhattan. Her well stocked liquor cabinet contained everything needed. She suggested I make my drink, pour her a red wine saying she'd return in a minute or two.

Her condo is located at the corner of the building. The view from the twenty-first floor faced south it looks at out to Lake Michigan and the "outer drive". The sky was clear the moon was a crescent bright in the sky. The temperature was about freezing. too cold to step out on the balcony.

While she was out of the room, I thought how can Mandy afford this lifestyle?Rembering she was an only child. I knew her parents and they had a very successful liquor business. No doubt they helped her secure this condo.

When Mandy returned she'd changed clothes, now dressed in what is best described as sensual. Tight black pants and a tight knit open weave lacy shirt. Her clothes were very revealing. Clearly she was not wearing underwear. Both standing I handed her the wine I'd poured and we kissed again but now tounge to tounge. We sat on the sofa in the dimly lit living room and admired the view of the city.

She spoke first saying you must know I've always been in love with you. I answered saying you know I've always been in love with you too. Mentioning this to each other was a first. She'd been my secretary for the last fifteen years. Being professionals we'd never explored these feelings before.

We sat pretty much facing each other. Midcentury jazz was playing on the sound system. We continued expressing our feelings for each other. I made another round of drinks. We continued kissing and caressing. We were advancing rapidly, to the anticipated love making.

Taking my hand we walked to her bedroom. Another beautiful view of the city from the window with a great view of Lake Shore Drive. She laid on the bed. I laid down next to her. Kissing led to more, much more. Lovingly we removed each others clothes. Touching each other sexual excitement was building.

The dim lighting in the bedroom revealed her beautiful body to me. Long legs, muscular abs, large breasts with pink nipples. Beautiful face, auburn hair and pink varnished nails. Touching her hairless pussy, it was clearly wet with desire. Whispering don't move she slid down and began licking my hairless balls and cock. Mandy took my cock into her mouth. My body heaved with pleasure.

I returned the favor by assuming the sixty-nine position and ate her pussy. Her body responded by raising her pussy to have more of my tounge in her. Now it was time to fuck. Mandy whispered fuck me hard. I held my rock hard cock in my hand and gently inserted it into her. My cock was welcomed by her wet warm pussy. I easily slid all the way in to my balls and stopped to enjoy the pleasure of the moment.

She said I've imagined this moment for years. She added that being about the same height we fit each other perfectly. Mandy said she knew I had a fit body but to see it shaved, lean and muscular was more exciting than she'd imagined.

We made love in every possible way. As my sperm left me we both began to orgasam. It felt like a head on car crash at one hundred miles per hour. I rammed my penis into her as deeply as humanly possible. I felt my sperm leave me and enter her.

We were consumed by our passion and our lust for each other. Missionary style sex was never more pleasurable. We took turns on top and bottom. Again and again we made love, we rested and continued. It must have been two in the morning when we fell asleep. Later that morning about six, I was able to get out of bed. Slipping on my bikini underwear and shirt I walked to the kitchen.

Mandy was there in a short almost sheer robe. She reminded me of the Vargas Girls, that appeared in Playboy magazine years ago. K cup coffee was brewing. We kissed, as we sat on the bar stools at her kitchen island. We talked about the sex we'd enjoyed together. She said she was having dinner with her parent this evening. Would I please join them? I answered yes. She said that they have known for along time about her ongoing crush on me. She said she knew that they would be delighted to see us together.

Before I left I told her I would pick her up on the way to dinner. I added that I'd come up and drop off some play things for some after dinner fun. I plan to make our relationship work. Might Mandy be the one? Time will tell.

673djp
673djp
77 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
FlyingDutchmen38FlyingDutchmen38over 1 year ago

needs a sequel maybe foursome with parents

Share this Story

Similar Stories

Office Stress Therapist! A sexy "Secretary" is actually a stress therapist!in Loving Wives
Friends and Lovers Pt. 01 Her best friend stays over at her place...and things heat up.in Erotic Couplings
Spontaneous Wife Ch. 01: Summertime BBQ A wife gets to thinking about how life is too short.in Erotic Couplings
Conference Room B Fuck Club Employees request time and a place for making babies.in Erotic Couplings
Neighbors James finally gets his chance with his neighbor.in Erotic Couplings
More Stories