Executive Assistant

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40 year old spinster finds love.
2.1k words
4.25
16.3k
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Emily Swanson spent most of her life taking care of her parents. She had a brief affair at college, which was pretty much the total of her sexual experience. She worked long, hard hours as an Executive Assistant at a large corporation. Practically all her money went to taking care of her parents. Her mother was recently placed in a high-priced care facility.

Emily was rather attractive, with beautiful large brown eyes. She kept herself well. Neat, well-groomed, conservative clothes. Tall, shapely legs, trim figure, Just no time to socialize. On the job, she oozed efficiency. Always punctual, kept excellent records. She was a star employee.

The layoff bug had hit the corporation. Everyone was looking over their shoulder. The corp headquarters had just replaced Emily's boss, and she was very nervous.

She was called into the new boss's office, Mr. Ed Brown.

"Yes, Sir," as she walked in, notepad at the ready.

"Sit." Miss Swanson

Emily sat somewhat nervous. Mr. Brown looked rather grave.

"Emily, I have to decide whom to keep and whom to let go. But, of course, I would rather not let you go. However, you're going to have to make some changes."

Emily stuttered, "I don't understand what changes?"

"Open your legs," Miss Swanson.

Emily blushed bright red, sure she misunderstood him.

Either open your legs or go clean out your desk. No discussion, no argument, do it.

Emily timidly opened her legs. She was wearing a knee-length skirt, pantyhose, and plain white panties.

"From now on, that's how you will sit in my office, understand?"

"Yes, sir," she answered.

The rest of the day Emily spent trying to impress Mr. Brown with her efficiency. She struggled to remember to open her legs when she sat. Emily had a habit of beating the boss to work, but Mr. Brown was in his office the following morning. A first for her.

"Come in." Miss Swanson

Emily went in he motioned her to sit. She remembered to open her legs despite the humiliation.

"Well done, Miss Swanson," with a smirk." tomorrow, I want you wearing stockings and a garter belt. You may have time this afternoon to shop if required. Your clothing choice non-negotiable, do you understand,"

"Yes, sir," head bowed.

The rest of the day went as a regular workday. Mr. Brown was very efficient, a trait admired by Emily. The following day, as she sat in his office, she struggled to open her legs. Emily thought of the alternative and knew she could not afford to lose this job. She spread her legs.

"Very nice, Miss Swanson, your prospects are looking up." as he could the whites of her thighs above the stockings.

The following two days were uneventful. They worked well together. Friday afternoon, as they were closing up for the weekend, she was sitting in his office.

"Miss Swanson, no panties on Monday or any day after that, understood?"

Emily started to protest.

"It's your choice, Miss Swanson. Take it or leave it."

Humiliated, Emily knew she would come to work with no pantie. However, she had to admit that sitting in front of Mr. Brown with her legs open did excite her, and she found she was wet by the end of the day.

Monday morning, sitting in his office, she sat legs open. He gestured for her to open them more. She could only imagine just how much he could see. After work, she would jump in the shower and masturbate. She was so hot. His perversions were turning her on. The following week, he told her they were going to lunch. She thought that it was nice of him to take her to lunch.

The restaurant was a very exclusive establishment. Carlos asked Mr. Brown if he wanted his unique table. Carlos showed them to a somewhat secluded table which could not be seen by the other patrons, None of this registered on Emily. Their waiter Paco bought Mr. Brown's usual drink and asked what Emily would like. They sipped their drinks. He put his hand on Emily's leg, and she started to push his hand away.

"For your good, don't do that.'

Blushing, Emily let him keep his hand there. Paco came with another round of drinks and asked.

"The usual amount of time, Mr. Brown?"

Paco was well aware of what was about to take place.

"Emily, it is decision time if I may call you Emily. You will do what I want when I want it, or you will get up and leave. I will give you time to go pack up before I get back, or you can follow instructions as you have been."

He moved the table covering to reveal his erection, "Suck my cock, Emily."

Emily was horrified, but she couldn't take her eyes off his naked erection. It has been years since she last saw one, and this one was big.

"Well, I see you haven't left."

Placing his hand on the back of her head, he directed her mouth to his cock. She put up almost insignificant resistance. Her emotions almost overwhelmed her as the smooth, velvety head filled her mouth. She savored the taste and smell. He pushed her further down on it. With a few instructions, he had her bobbing up and down on it. He was nearing climax, but due to her inexperience, she had no idea what was coming. He held her in place as he came in her mouth, giving her no choice but to swallow. As she pulled her head up, she saw Paco standing there smiling. She reached for her water glass.

" No," Mr. Brown said, "I want you to get used to the flavor."

Emily thought she had just gotten through the most humiliating experience of her life. She sat still till lunch arrived, finally allowed to drink something. After lunch, Mr. Brown ordered dessert. While waiting, his hand ran up her thigh again, all the way this time.

"Open your legs wider."

She opened them wider he began fingering her. She was soaking wet. He was quickly bringing her to orgasm. Paco brought the dessert, but the fingering went on as he watched; Emily had an orgasm in front of the waiter. The humiliation washed over her.

After work, she went home and did her thing in the shower, but she dreamt of a big cock filling her mouth and drinking loads of cum that night. She woke up with her hands between her legs and finished by rubbing her clit.

He called her Saturday afternoon after she had visited her mother. He told her he would pick her up in an hour to go shopping. He had his hand up her skirt on the way to the mall. They entered a designer clothes store.

"Is the stuff I ordered ready," he asked the clerk.

Yes, sir, she replied, leading them back to a fitting area.

She handed Emily an outfit to try. Emily couldn't believe her image. The skirt barely came to the top of her stockings. The blouse was tight and low cut, so low she couldn't wear a bra with it. She had to admit she did look hot, but it just wasn't her.

She walked out to model it. It was approved, as were three other outfits. she wore the first outfit out of the store. It took a lot of courage. Then, they went to the food court for coffee. Emily knew she was on display, which excited her.

At 7 Monday morning, she arrived in her new outfit. She was called into his office.

"Show me your" tits he ordered.

She unhooked the top, letting it drop, exposing her breasts. Then as ordered, she knelt between his legs and began licking his cock. Her sucking technique had gotten better. She worked the tip with her tongue. She could hear him moan and squirm finally. She took it down her throat. He shot his load down her throat, and she loved it. Then, she got up, wiped her face, and went to work. She was informed this was to be their daily routine.

Emily started looking forward to the morning blowjobs. She began to think she was as perverted as he was. she looked forward to him cumming in her mouth.

Ed was almost overwhelmed watching her slurp and suck on his cock. But, like everything she did, she did with efficiency. Her beautiful face between his legs was a dream come true. He had just come through a very bitter divorce where even his kids turned on him. Right now, he was struggling with a borderline impotence issue, and blowjobs were about the only thing that would get him hard. His shrink advised him it was a mental issue and that he was severely traumatized by his divorce. He was surprised by Emily's submissive nature; he had told her to open her legs on an impulse and had been on a high ever since. He couldn't wait to see what else she would do for him.

With those thoughts swirling around, he came in her mouth, watching her gag then swallow.

Emily was starting to enjoy wearing the more revealing clothes. She certainly had the figure for it and was getting more attention which she liked. She came in for her usual start to the day, and Mr. Brown told her to pack for a week they were going on a trip.

They ended up in a quaint little Beach village in Mexico. The resort was lovely and certainly a lot more than Emily was used to. They were going to eat lunch poolside, and she was handed a shopping bag and told to wear it for lunch. The bathing suit was a string bikini. Emily struggled, and it took everything she had to put it on.she had to trim her pubic hair to avoid embarrassment. The top barely covered her nipples. She forced herself to walk down to the poolside dining area, Her almost perfect 34C tits on full display. Ed thought she looked like a goddess.

After lunch, he took her to a beach, which she found was a nude beach. Soon she was naked, lying in the sun, admired by several men, more than a few of them married men. They waded out in the water waist deep, and Ed finger fucked her till she came. It is evident to anyone watching what they were doing.

When they got back to the lodge, Ed bought Emily into his room. The windows and shads were open.

"Strip Emily "

After being naked half the day, it didn't bother her at all.

"Bend over that table." He demanded.

Surprised by the demand, Emily hesitated then lay over the table. She felt hands on her hips, then him pushing into her. He almost had it in. Then it went soft. Suck me, he demanded.

The following day he told her he had a job for her that evening after dinner. So she reported to Ed's room, and he was there with three young men.

Looking at Emily, "I want you to entertain these gentlemen, do whatever they want."

Ed then stepped out of the room. The three men started stripping. Finally, Emily realized what they wanted. So it had come down to this, servicing customers. She felt betrayed as she sunk to her knees and began sucking the first cock. She felt someone behind her, then a cock slide into her. She had no idea she was that wet or hot. She sucked and fucked for hours. Finally, They double-poled her. When they were through, she couldn't help but think it was the hottest experience of her life, but strangely unfulfilling.

Ed was surprised when she didn't stop by at seven. Then he figured she been worn out from last night. But, instead, he found her at breakfast.

"How was last night?" He asked brightly

She stared at him intently "if you ever do that to me again, I quit."

"What, why? Didn't you like it?"

"The sex was fine, but I'm not the company whore for your clients."

Ed was almost speechless "no, no, and they weren't clients, I hired them just for you, I wasn't able to satisfy you, I just want you to have a memorable end to your vacation."

Emily replied angrily, "I never complained, don't do that again."

Not much else was said between them during the trip back and their separation at the airport. The next morning at work, Ed sat at his desk wondering what was next.

Promptly at seven, Emily came in, knelt between his legs, and began to suck. Ed managed to relax.

"I was afraid you might not show."

Emily pulled her mouth off his cock "don't you realize I get my satisfaction from doing this for you? That first day you told me to open my legs, I have been committed to serving you. I don't need to be serviced by some studs."

"Emily, I love you." he stammered.

lifting her head, "I know Mr. Brown, and I love you."

She swallowed his cum, stood, wiped her mouth, and went back to work.

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AnonymousAnonymousover 2 years ago

I enjoyed this story, very much. Simple, HOT little story with a very nice ending.

AnonymousAnonymousalmost 3 years ago

Goes from next to zero experience to an anal slut for the boss in like 800 words. So believable.

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