Sister Jean

Chapter 1

A few years ago, Alan had a thriving business. Slightly sketchy but, making loads of money. He had a great team. Then the tornado hit. His wife had suddenly filed for divorce. And in brief, she cleaned him out. He didn't have enough funds to continue. So, he took some time to heal. And now after a few years of living off of savings he knew he would have to find a source of income. He day traded, but that wasn't going to pay the bills. He had a small 2-bedroom place he rented. It was enough. His dog was with him and that was company. Just on a whim he got a lottery ticket. Maybe he would win enough for another ticket.

A day later when he was getting gas, he stuck the ticket into the scanner. The machine beeped and locked up. He looked at the screen. Large prize. Maybe it would pay the rent. But later that day he got the biggest shock of his life. The win was $50,000,000. I suppose that pays for the rent he thought to himself.

And after a brief whirlwind of activity, he had the money in the bank. He had rented the top floor of the nicest hotel in the city, and was sitting looking out the window from there pondering his next move. It had a few bedrooms and was fully furnished. He was sending his dog to his cousin to sit until life settled. The dog was like a child to him and very important.

Looking out the window at the falls, he took stock. Material possessions were easy to come by. Travel, should he choose to, would be simple. What was missing was a significant other. Being single was a lonely thing. Finding the wrong woman would lead to financial disaster. Another financial disaster. So how to find the right one?

Putting an ad on the net, 'rich guy seeks significant other', would bring every nut bar out of the woodwork. The type of woman was important. There was a grocery list of wants. Decent looks. But not model level. Smart without being conniving. Good personality. More humble than arrogant. And, no major family ties. Someone he could mold into a long-term friend and companion. But to bring in as an employee so if things went off the rails he wasn't going to be taken to the cleaners. And perhaps the dimmest hope of a physical relationship.

The ad finally came out this way. 'Financial executive seeks long term executive assistant. This is a live in position. Minimal family ties preferred. Experience is less important than a trainable attitude. Travel likely involved on a regular basis. Financial experience not required. Domestic duties involved. Excellent compensation.'

Alan posted it that morning and the responses went to a new email he had created. In no time there were thousands. He weeded out the males so that dropped many off of the list. From the balance, the very long multi page responses, and agencies, were discarded as well. The hard-core career women were a total threat.

Finally, one caught his eye. The title read Jean Sullivan. Nothing more. This is what she said.

My name as stated is Jean Sullivan. I was until recently a nun. Due to a change in circumstance, I am no longer. I have no family. At the moment I don't have a permanent residence and am staying at a hotel. I am left with very minimal funds and would be willing to negotiate on wages to your advantage. As a nun, we all took turns doing the domestic work so I'm amenable to that. I'm honest and trustworthy. I would be available quickly for a meeting. Bless you regardless of your choice. You can reach me at "***".

Alan sat back and reread the letter, then he picked up his phone and called her number. At least on the face of things she was the one. Her sincerity was obvious and he believed her statement about being trustworthy. Sometimes you know it when you see it.

Jean picked up the call on the second ring. "Yes?"

He said "Hi, my name is Alan. You answered my ad for an executive assistant."

There was a pause. "I see. The ad was vague to some degree. If this is a scam, I'm wiser than that. If it isn't I'd certainly like to know more." She said.

Alan replied. "The ad is quite legitimate. Of the thousands I got, yours stood out for its brevity and honesty. I don't want to get tricked either."

"Then we are on the same page it seems." said Jean.

"Indeed. I don't know how quickly you can accommodate me, but I would like to meet you first thing in the morning. If you're free, can we meet at 9 at the Foxworthy hotel dining room. I'll buy us breakfast." Jean agreed as she wasn't living far off.

The next morning, he was waiting in the restaurant when Jean was directed to his table. As she approached, he took stock. 5'2 or so. Thin. A very pretty face. Good posture. No makeup. Slightly hesitant. Shy. Very plain grey shirt and skirt. He supposed her nuns attire. And light brunette hair with just a touch of grey at the edges. Her hair was obviously just growing in from being short the way nuns are wont to have it.

He stood as she was seated. She smiled easily. This was very positive so far. They chatted quietly about the weather as breakfast was served. Then the falls. That was always fascinating. When he had worked, he managed people. He was trained to observe. While Jean wasn't untoward, it was obvious she was quite hungry, he didn't think she had eaten recently.

"So, tell me. What would prompt a nun to suddenly change her life? May I ask that?" Alan said.

Her face darkened a bit. "Two months ago, we nuns got up and found the mother superior gone. As it turns out the mother superior had sold the building, taken most of our funds and just disappeared. She left each of us a small amount of money. That doesn't last long." Jean said grimly.

"When did you last eat?" asked Alan.

"Being a nun, I won't lie. Two days ago. If nothing else comes of this, you don't know what you've done for me now and thank you."

Alan looked over. "I thought as much. That was awful what she did. Evil can find its way into the most unlikely places. So, we are going to start this properly." He put an envelop down in front of her.

Jean looked at it. "What is this?"

He said. "Its $1000. For your trouble coming to see me."

Jeans face fell. "So, I'm not up for the position? "She asked disheartened.

Alan smiled. "On the contrary. My list just became you. You have all the qualities I'd hoped to find in someone. The cash is to ensure you can manage while we work out a deal. Is that fair?".

Jean was shocked. "More than fair. Then what is next?" She asked puzzled.

"I'd like you to come to my office and we can see what arrangement we can work out." Said Alan.

"All right. Where and when?" asked Jean.

"Actually now. I'll make you a coffee when we get up there. I rented the entire top suite of this building". Smiled Alan. Jeans jaw dropped open. Shortly after they got up and headed to the elevator. Jean was in for quite a number of surprises to come yet this day.

Once in the elevator he entered the special code that would take only this elevator to the penthouse. As they alit, the area facing them was amazing. A panoramic view of the falls and living spaces down one wing. The living room had beautiful furniture. In one corner was an office desk. A kitchen was just a bit further in. He looked at Jean. "Why don't you make us coffee?"

Jean was hesitant. "I don't know where anything is?"

"Well, lets learn together. I only moved in here yesterday." Alan said. Jeans head was on a swivel as she took it all in. Between them they found the necessaries and made coffee, then went to the office area.

"I want to know all about your entire life, Jean. But to be fair I'll go first. I wasn't quite honest. I'm not a financial executive." Jeans face was concerned and she was looking at the elevator. "The fact is, a short time ago I won the lottery. It was a very, very large sum." Alan said as he gazed out the window. "Tens of millions. More details later as it applies. Now its your turn."

Jean was still reeling from the revelations. "The reason I have no family; I was a foundling. A baby left on the steps of the convent. I'm going to turn 40 soon. The convent has been my home and life since then. Now that the convent is no more, the nuns all scattered to try to find a way to survive. I'm nearly out of money. I'll have to sleep in my car tonight but its not cold out."

"The money I gave you will forestall that at least. I'm going to start with the good parts of what I'm offering. I intend to buy a mansion. I want you to be part of that purchase and decision. You'll be living there in your own space. I will be buying you a car. Yours to keep, regardless of how things go. And to start by way of cash I'm going to offer you $15,000."

Jean pondered this. "That really isn't much by way of wages. I don't need much but $1200 a month isn't a lot." She looked sad.

Alan laughed out loud. "My dear lady, the $15,000.... is monthly." Jean sat back in her chair in shock. "Where do you bank?" he asked. "I don't have a bank account. I never needed one." She said meekly.

"That isn't acceptable. I will get you set up immediately." said Alan.

Jean looked at him steadily. "And the downside? The bad parts?"

Alan looked back at her. "After this you might just walk out. My expectations are large. First. Domestic. Meals and cleaning. That's easy, I'll hire a cleaner, if need be, to help. Second. Your dress is unacceptable. I suspect you have a very attractive body. I will finance your fashion to accentuate that. Can you handle it?"

"It was necessary to dress in a very chaste manner at the convent. I don't own any other clothes. I've never tried any on. I'm going to be shy and bashful. But actually, I'm eager to try." Jean said.

"It gets more challenging. I'm hedonistic. Basically, if it feels good do it. I want you to embrace that. What size bra do you wear?" he asked

Jean was tongue tied for a moment deciding to answer or not. Finally, she said "That's very personal but,32-c." She was getting nervous.

"Going forward I want you to accompany me mostly everywhere. That includes the beach for instance. So, right now, go to the washroom down the hall, remove your bra and bring it to me." Said Alan. This was the make-or-break point.

"I'm not some cheap tart." said Jean with some indignation.

"Of course you aren't, but, neither are you a nun any longer. Its time for you to embrace a new life. Do it now." Demanded Alan

Jean thought for a long moment before she got up and headed down the hall. Once there in the bathroom, she stared at herself in the mirror. This was an opportunity that would never come again. She removed her shirt. Reaching behind her she undid her bra and let it slide down her arms. Her tits hung a bit. She had large dark prominent nipples. She put her shirt back on and returned to the office. She quietly set the bra on the desk in front of Alan.

"I was watching your tits sway as you walked. You have a great body. I hate bras and don't want you wearing one unless we have company or such." Said Alan.

"No man has ever seen this before. My doctor was a female. I'm embarrassed." She was nervous, she didn't meet his eyes.

"Are you a virgin?" Asked Alan with interest.

"Yes." said jean quietly.

"I see. Now, stand up and take off your shirt. I'm going to see your body at some point, now will do." Said Alan firmly

Jeans eyes flew open. "No, I can't!"

Alan looked her in the eye. "Now!" The woman stood up. She was totally spun. But she started to undo her buttons with shaking fingers. Then, she took off her shirt and set it on the chair behind her.

Alan stared at her chest. Her nipples were hard and dark. Her breasts hung. She had what he considered a perfect body. "Are you ok Jean?" he asked

"No, I'm not ok. I've never done anything like this. I'm a good girl!" Jean was almost in tears. She was breathing heavily.

"Come to my side of the desk." He demanded. Jean meekly complied. Alan reached up and held her tit. She jumped. He began to gently rub his thumb over her nipple. It got even harder. "How does this feel Jean?"

She looked at his thumb. "It.. it feels good."

Alan reached up and began to do the same to the other breast as well. Jean moaned. "Being a virgin, how did you get relief?" He asked.

"I didn't. I prayed until the evil thoughts went away." She was watching his hands work on her tits.

"Come closer yet." He told her. As she did her took her right tit in his mouth and began to work on it, kissing, sucking and massaging it. Jean moaned. Her chest was heaving.

"Now for the next step. Drop your skirt. Show me your body" He said. Jean had lost her resistance. She reached over, undid the zipper and the skirt fell to the floor. She was wearing plain white granny panties. The crotch was soaked. Alan pushed her legs apart and began to run his hand over her pussy. Jeans hips began to move with his hand. "Push them down Jean" said Alan and she did. She had a full bush and it was soaking wet. As she stood in front of him. He began to run his fingers over her lips finally finding her clit. Jean was moaning louder now. "Do you want my finger in you? Tell me. Say it." He demanded.

"Yes, put it in me. Please!!" She moaned. Alan began to rub her clit more quickly. Jean was out of control. He finger fucked her with two fingers. She finally came and squirted all over the desk, then collapsed onto the floor still shaking.

After letting her recover for a few moments he pulled her to her feet. She was a mess. He put his hand behind her neck and pulled her close. He kissed her. A deep kiss with his tongue down her throat. As he did, he started to stroke her again until she once more had a massive orgasm. He held her this time. He looked into her eyes. "Are you going to be my slut? Will you give yourself to me? "He asked

"Yes." She said quietly.