Sandy Ch. 01-05

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

"Usually it's the case. However, when a respectable woman misbehaves like a naughty child, her punishment should fit the crime. Don't you think so?"

Sandy whispered, "Yes sir..."

"Take off your panties and assume the position!"

Sandy was wearing a short skirt. She removed her panties, while the skirt was still covering her cunt and butt.

"Bend on my desk and lift the back part of your skirt! My intention is to stroke your bare ass cheeks!"

She looked at me with pleading eyes.

I gave her a stern look.

She sighed and hesitantly lifted her skirt, showing me her stunning rounded ass.

I moved behind her back, told her that she'd receive 15 strokes and instructed her to count them accurately, otherwise we'd start over.

My palm landed on her smooth cheek relatively mildly.

The next one was somewhat stronger and gradually the strokes became harder.

Sandy counted all the way to 10 and then she forgot what number it was.

We began from 1 again.

After spanking her ass 10 more times, her cheeks were very red and raw, but she showed no signs of distress.

After the 12th one Sandy stopped counting.

I asked her, "What happened?"

"I am tired of counting..."

"Sandy, you know what it means, don't you?"

"Sir, I know that I deserved my punishment. Do what you have to do..."

"Sandy, spread your legs! I am going to spank you 5 more times!"

She spread her legs wide and lifted her butt high in the air, as she leaned on my desk.

I flogged her cheeks 5 more times.

Every time my palm hit her flesh, her body shivered and a moan escaped her mouth.

Her exposed pussy folds were very wet!...

I blurted, "Sandy, I see that the spanking does not cause you any suffering. In fact, you have become a horny bitch. Am I right?"

She remained in the same position and stayed silent.

"Bitch, I asked you a question!..."

Sandy covered her face with her hands and whispered, "Yes sir. I am sorry..."

I approached her behind and gently trailed her butt cheeks.

"Sir, what are you doing?"

"I am checking to see if there is a permanent damage to your cheeks. Any objection?"

She didn't respond. Her body started shaking under my touch.

My palm slowly moved to her perineum then descended to her moist pussy.

My finger pushed lightly against her entrance.

Sandy didn't move. She mumbled, "Sir, what are you doing to me?..."

"I noticed that the punishment aroused you. Would you like me to finger you to a climax?..."

Sandy's mouth stayed closed, but her body was now quivering more intensely.

I inserted 2 fingers into her vagina and slowly massaged her G spot, while my thumb was tweaking her prominent clitty.

I was doing it for 2 minutes before her body stiffened, a loud cry escaped her lips and her body convulsed on my desk. Sandy's orgasm lasted few minutes before slowly relaxing.

I covered her butt with the skirt and went back to my seat.

Sandy's head was still buried between her hands. She didn't dare looking at me.

"Sandy, stand up and look at me!"

She hesitantly stood up and lowered her hands. Her face was beet red.

I showed her the 2 fingers that were inside her pussy and slowly inserted them into my mouth. I licked and sucked on them, while glancing at her.

She mumbled, "Oh god! What are you doing now?..."

"I tasted your juices. They taste very sweet. So now that you had your climax, do you think that you can retype the documents without stupid errors?"

"Sir, no more mistakes. I promise!..."

She left my office in a hurry with her face still blushing profusely.

After she exited, I went around my desk and grabbed her panties from the floor.

I sniffed them. The smell was intoxicating...

I thought to myself, 'our working relationship is at a crossroad. So far it was... interesting. I'd like to continue further, but it was up to Sandy. Would she screw up again to make it happen, or become a perfect employee to keep her marriage intact?...'

I was anxious to know...

Ch 2.

The next 3 days Sandy's behavior was very professional.

She had great ideas how to improve businesses of 2 clients and typed 25 pages without any errors.

The only clue that Sandy wasn't over her prior ordeal was the way she gazed at me.

Her look was a combination of fear, pleading and lust...

I ignored her glances.

If she wanted to be a loyal wife and 'get over' her urge to be submissive, I won't bother her again.

It was HER choice!

Unless Sandy began making mistakes again, she'd be ONLY assistant.

On the 4th day Sandy showed up dressed in a shorter skirt and sleeveless white blouse. Her pink soft bra was seen through the thin blouse.

She brought me the morning coffee and bent forward to hand it to me.

While doing it, she checked my eyes to see if I was peeking at her cleavage.

I was tempted, but decided against it - If she wanted to play, she'd have to surrender with more than a hint!

During the day she behaved like a good assistant.

Only late afternoon when Sandy was about to leave, I saw her disappointed facial expression.

The next day Sandy seemed more determined and cheerful.

She served my coffee and added some cookies, that she made at home.

I thanked her and immediately switched to our work, asking her to type a thank you letter to our latest happy customer.

Sandy brought the letter 1/2 an hour later and rushed out of my office.

I was still able to see her blushing.

I thoroughly checked the 5 page letter.

The first 4 pages were flawless. The last page had 3 errors!

I smiled, 'So she made up her mind and decided to be my sub... Good!'

"Sandy, come to my office, please."

She entered slowly with her eyes examining her shoes...

"Sandy, you know exactly what you did. Am I right?"

She didn't answer and her eyes avoided mine.

"Take off your clothes!"

"Please sir..."

"No please! You know the rules! Remove ALL your clothes and do it now!!!"

"But sir, you may spank me without me taking everything off. I am married..."

"Sandy, you knew your marital status BEFORE you decided to test me and you did it anyway! Now stop wasting my time or the punishment will be more severe!"

She sighed and took her time to remove one item after the other.

Sandy remembered that I saw her bottom parts already, so she removed her skirt first, followed by her panties. Then she looked in my direction.

My eyes were initially focused on her mound and then moved up to her face.

Sandy had a strange smile on her face, that I could not decipher.

Then she stripped her blouse and remained with only a bra on.

She stared at me with her eyes begging me to stop it.

I looked back at her and didn't budge.

She sighed and her hands moved backwards to unclasp her bra.

Sandy let it fall to the floor while both her hands on her tits.

The large areolas were fully exposed and her hands barely covered her nipples.

"Sandy, you misunderstood. I meant stand up NAKED with your arms beside your body!"

Her hands moved at a turtle's pace to the sides of her body.

Sandy's marvelous boobs were now in full view...

They were gorgeous! I had a strong urge to touch them, tweak them and suck her dark nipples.

I stood up and approached her.

It was a mistake, because my cock was already pushing hard against the front of my pants.

In my imagination I could hear my pole asking for permission to park in the valley between her twin peaks...

Sandy watched my face and then her eyes descended toward my groin.

My bulge was too obvious to ignore.

"Sir, how do you plan to punish me?..."

I sat on my bed and pointed to my lap, "Lie down here and get ready for 10 strokes!"

"OK sir."

Sandy positioned her midriff on my body, while her head and legs rested on the mattress.

Her groin was on top of my hard cock!

"Girl, count correctly if you don't want us to start over!"

The first 4 strokes went as expected.

Until the fifth one she counted normally and Sandy's body lied still.

Then her body began to squirm over my engorged cock.

I continued to 6 and then 7.

Her gyrations over my member intensified, pushing the organ upward still.

She whispered, "Sir, if your suffering hard penis stays caged, it will break..."

"You may free it if you want, but then we'll have to start over your smacking!"

Her small hand found my zipper under her body and gradually unfastened it.

My dick was still inside my briefs, but this was a minor hurdle.

It pushed itself toward Sandy's entrance.

I continued spanking her red butt cheeks.

Sandy started recounting and reached 6 before mumbling, "It's uncomfortable!"

Her palm found my groin again and pulled sideways the front part of my briefs.

My exposed cockhead was now directly aligned against her naked pussy.

The cunt folds were damped...

Yes. The lady was highly aroused!

As my flogging continued, her gyrations slowly directed my prick head into her vagina.

I did not help.

Her body motion became more targeted to get my cock inside of her and she whispered, "But sir, you cannot do it to me... I am married..."

Deep inside I was marveling at the discrepancy between her talk and behavior.

I made up my mind to go with what she was doing and ignore her excess verbiage.

"Oh shut up you horny bitch! You talk too much! I am not interested in your marital status. Now sit up straight and ride my cock like a good slut! We both know you want it."

She sat up on my groin with her legs on both my sides and began back and forth movements, letting my prick penetrate her hole deeper and deeper.

All this time her lips continued whispering, "Sir, but I am married..."

I leaned backwards on one hand and placed the other one on her tempting breast.

It was soft and smooth and the nipple was rock hard...

I rolled it between two fingers and she moaned. Her eyes were closed.

I kissed her lips gently. Her face backed, still mumbling, "I can't... I am married..."

I pinched her nipple and she started whimpering.

Her breathing accelerated and the pulse rate was immeasurable...

I sat up straight and with my other hand massaged her clitoris.

Sandy's body jolted in the air and then landed back on my hard cock.

It followed by her body shuddering, as she reached a massive orgasm.

Her mouth was open and incoherent sounds emanated every now and then.

I kissed her mouth again. This time her face did not retreat.

My tongue found hers and pulled it into my mouth. I sucked on it gently.

As her climax subsided, Sandy's body began to relax and I had to hold her, so she doesn't fall.

Subsequently I stood up and placed her body in a supine position on the bed.

I zipped my pants and went to the bathroom to pee and clean up.

When I returned, Sandy was sitting on the bed, still naked, with her hands covering her face.

She said, "What did we do?... I am married..."

I hugged her shoulder and kissed her forehead, "Yes you are... I'll get out now and let you dress up. I'll be back in 10 minutes. If you are still in my office, we'll talk. If you go to your office, we are going to have this talk some other time..."

Ten minutes later I opened the door to my office...

Ch 3.

I opened the door and Sandy was no longer there.

Her office was dark and empty. Sandy left.

I sat down and tried to reassess what happened.

In the morning sandy seemed mentally prepared to give in to her submissive nature. During typing the letter she purposely made errors, knowing that she'd be punished.

Did Sandy expect only to be smacked and I crossed the line by forcing her to undress completely? Would she hate me for taking advantage of her vulnerable state, that ended up with an intercourse? Was this the first and only time we had sex? Would she quit???...

With no clear answers, I had to wait and see what she'd do next.

The next morning I got a text, 'Sorry, I am not well. If it's OK with you, I'll stay at home today and tomorrow. Sandy.'

I texted back, 'Take as much as you need.'

For 3 days I worked hard. I worked for two...

On the 4th day Sandy arrived. She was wearing a short skirt and a thin blouse, as before.

She offered me coffee as if nothing happened.

Then she asked me if I had special requests.

I looked her in the eye. Did she mean WORK related request or a more personal one?...

She gave no hints

I elected to address the issue as if it was a question about business. I handed her 2 files of potential clients, who wanted to know more about our consulting firm, as well as a 1 page letter to an old client congratulating him for his 70 years old birthday.

Sandy went back to her office.

I haven't seen her for the next 3 hours. I was busy discussing issues related to a talk, that I was supposed to give in a symposium next month. Then I had a business meeting with a competitor. He offered to divide our territories, so we won't be at each other's throat. I told him that I'd think about it.

I arrived back to the office at lunch time.

I saw Sandy near the coffee machine and asked her if she wanted to go with me to lunch in a restaurant nearby.

She hesitated and then agreed.

It was a simple sandwich and burger place. Intentionally I didn't want to go with her to a fancy restaurant. For all intents and purposes I let her understand that it was a work related offer and not a date.

We were lucky to find a small table near a window.

We grabbed our sandwiches and I inquired, "Sandy, you were out for 3 days. Do you feel better now?"

She glanced at me for a long moment and blurted. "I still have headaches, dizziness and occasional confusion, but I think that I am doing better."

"Sandy, the way you describe yourself, you are not OK yet. How do you expect me to assign you to new clients or type anything if you are not 100%?"

Sandy gazed at me, "We need to talk. But this is not the place. Can we do it in your office after our lunch?"

"Of course!"

The next 15 minutes we ate without talking.

Multiple potential scenarios occupied my mind. Did she decide to leave? Was Sandy thinking about certain conditions to return to work with me? Did she confess to her husband about our tryst?...

Without any hints so far, I was clueless.

We'd talk in my office. I'd let her speak and see where the wind was blowing...

We arrive back to my office and sat side by side.

I waited patiently for her to start.

She stared at the carpet for a long time and then began talking, "Joe, I like working with you. You are smart, know a lot about business consulting and a great teacher. You are very generous with my salary and benefits. There is only one issue that I have. I am sure you know what I mean... You are a dominant person and I am... the opposite. It wouldn't be a problem, except that I am married to a good man who loves me and I love him. I don't know how to solve this dilemma..."

"Sandy, I don't think I can give you a good advice. I'll stay dominant and your brain will continue pushing you to be submissive. You want to remain married to the love of your life and I understand it fully. The way I see it your options are 3... A. You can quit and move to work somewhere else. I may help you do it by suggesting other good companies as well as giving you a very good recommendation letter. B. Another option is for the two of us to work here and be professional. Meaning you are going to do your best and stop making silly mistakes, that tell me that you WISH to be punished... C. The third and last option is to continue what we started. However, if it causes you a major guilt trip and the affair takes a big toll on your mental stability, I'd consider one of the other 2 choices."

"Joe, this was my dilemma that I was struggling with for 3 days at home... I hate to leave such a perfect job. I checked on line and called 3 other consulting firms. Each one has lower wages, a need to travel a lot and I doubt that I'll be happy working with their bosses. I can try to be perfect at work. In theory it's not very difficult, because so far you did not give me anything that I would consider mission impossible. The problem is that our personalities complete each other so perfectly, that I'll be tempted to screw up again and enjoy the punishment..."

"Sandy, do you need more time to think it over? I'd love to have you around, but in the end it's YOUR decision."

"I know that you are right. It is a unique situation, because there is no use talking to my husband about it. He'll just be 'nice' and let me do whatever I chose..."

"Don't you have relatives or close friends that you can consult with?"

"My few relatives are too conservative. Their advice will be to find another job. I talked with my best friend, who knows me and my husband. She suggested to 'go for it' with you. She said that a match like that occurs once in a blue moon and it's not worth losing it..."

"Sandy, I suggest that you go home and make your choice. If you seriously considering moving to another company, I'd help you the best I can to find the most suitable place for you. If you stay in my company, you can try to channel your energy toward work, while looking for Dom/sub relations elsewhere. Look, you are too good to make big errors, so if you make them, I'll know that you decided to give up your rights and I'll take over!"

Sandy's stare was so intense... She seemed to want to say something, but she held her tongue.

Then she mumbled, "I'll come to work tomorrow and let you know. I promise..."

The next morning Sandy was already at work when I showed up.

Her face lit up when she saw me, "I put a vase with flowers on your desk. I also left the typed letter you asked me to do yesterday. You can read it, while I make your coffee."

I sat down and looked at the typed letter.

It stated, 'Dear Mr Johnson, congratulations to your 45 years in business. We tolerated you around, but we never really liked you. Sorry... Signed, Joe mama.'

I read it the second time and couldn't stop laughing.

The letter was very funny. But it was also a big relief to know that Sandy decided to stay and be my sub!...

I was still laughing when Sandy arrived with my coffee.

She bent forward, letting her massive tits obstruct my view and asked seductively, "Sir, anything else I can do for you right now?..."

"Not now. But I'd like you to be in my office in 20 minutes. Certain things will have to change and we better discuss them earlier than later. And from now on you don't have to be too creative with your mistakes. I'd rather rely on you at work. I'll use you as my sub without the need to check everything you do. And don't worry your... little brain, when I feel like it, you'll deserve punishment... Clear?!"

"Yes sir..."

Sandy was back in my office exactly 20 minutes later.

She looked at me, waiting for me to talk.

"Sandy, first thing I wanted to discuss with you has to do with your office attire. What you wear now is casual and pleasant. However, after seeing your naked body, I think that your clothes are not doing justice to your beautifully sculpted body. As I mentioned to you before, you should keep a formal suit in case we bring clients to the office, but most of the time it's only the two of us here, so I want your sexy body displayed with all it's glory. I'll give you $1000 and you buy with it several sheer blouses and demibras. In addition to working efficiently, you'd be my office eye-candy. Any questions?"

She chortled, "I thought that displaying my cleavage while serving your morning coffee would suffice, but now I realize that your appetite is stronger..."

"Yes girl. It definitely is! And while you are at the store, please buy a ruby red glossy lipstick. Your plump lips are worth it and more importantly, I'd like it!"

We both pretended to work that day, but we were too anxious to focus on work.