Rich Bitch Pt. 01

I smiled. The experts at the fat farm had done some personality testing. They wanted me to smile more. They told me I had a scowl much of the time. They wanted me to relax more. They gave me some relaxation techniques.

"Actually, Proctor, I am pleased. Just not sure I am still me."

We were on our way, Proctor looking at me in the mirror, "Miss Ricci, you are a beautiful woman, if you don't mind me saying so." I had kept my last name as Mr. Freedman had agreed.

"I don't mind at all. I hope people notice the difference."

"I'm sure they will."

As we pulled up to the front of FIS, Proctor held the door open for me and escorted me to the front desk. He would work the rest of the day at the facility I was at unless I needed him to drive me somewhere. As I walked to my office heads turned. I knew they would be talking about me for some time.

My secretary said, "Miss Ricci, welcome back. My goodness, you look great!"

I said sternly, "How I look is none of your business, now tell me about my day!"

Then I thought about smiling and relaxing. My secretary had her head down, shrinking away from me before I smiled at her and said, "Thank you, Denise." I knew I should have said more but that was all I could muster. I had a long way to go. It went this way for a long period of time as I had to retrain myself. Over and over I had to rethink a harsh statement before the smile and a friendlier pronouncement.

Before long I was asked out on a date. That started a string of dates. The people were all people that ran in my circle. I failed at every one of them. Somewhere during the evening, I would revert to that overbearing bitch I was so good at being. Almost without exception when I got home, I was angry and disgusted with myself. All of these men were successful and mature. But in each case, I got bored and picked something to run them over with. And none of them would or could stand up to me.

Not only was my dating a failure, I was frustrated sexually. The more my body healed and became, well sexy, the more it craved sex. I was masturbating often. I kept buying vibrators and dildos. I must have had about thirty. It was like every time a date failed I needed a new toy to be my lover.

Not only that, my one and only friend Proctor announced he was retiring. The security director was beginning to line up potential replacements.

I finally get laid

Proctor and I made a trip to the West Coast to meet with other Investors and evaluate a couple of startups for potential investments. The first two days were meetings from morning until bedtime. This was usual for a trip like this. But on Wednesday night we didn't have any meetings. I told Proctor I was going to work in my room, but I wanted to take him somewhere nice Thursday night to discuss his departure. I wanted to show him my appreciation for his service to the company and me personally.

Now for honesty. I was frustrated with dating people I knew, and I just wanted to get fucked. After all I had fucked only one old man. I wanted to fuck someone for the sake of just getting fucked. I had gained enough confidence in my body that I figured I could attract someone just by doing a little advertising. In hindsight, it was probably not the smartest way to start. There was so much for me to lose. I mean the press would love a story about a rich bitch like me with a one-night stand. But I was desperate.

I had packed a new outfit. One I bought myself and not my professional shopper. One like I had never tried before. It was a black cocktail dress with a V neck in front that showed plenty of cleavage but still tasteful. It was belted at the waist, with a skirt the flared over my large hips. The skirt hit about mid-thigh. With four inch heals I thought I looked as sexy as I ever had. I wore some cheap costume sparkly jewelry. I wore thin lacey bra and panties. I looked in the mirror and liked what I saw. I was sexy without being overdone. I thought I could attract some interest with my new figure. Truthfully, I had no idea what I was doing. I was however excited. I could feel a tingle over my whole body.

At eight snuck away to a hotel bar several blocks from where we were staying. I thought this would be far enough away so that Proctor wouldn't know what I was doing.

I walked to the bar. This was a safe area of the city. Busy at all times. I entered the bar, which was dimly lit and about half full. It had twice as many men as women. In looking around, I thought most of these women were prostitutes looking for tricks. Most were dressed far more provocatively than I. Many were showing far more leg, there were splits to the waist and obviously I was one of the few women with a bra. I began to worry that I wasn't advertising competitively. I wanted someone to pick me. It was so important to me to be selected by someone.

I sat at the bar and ordered a drink. I slowly sipped my drink trying to think of what to do. I was there over thirty minutes nursing my drink. My mind was going at high speed trying to think about what I should do. How was this done? Maybe, go to the bathroom and take off my bra. But where would I put it. The little purse I had only had room for cash and a lipstick. Maybe I should turn and show a little more leg. Should I just scream, "Come fuck me please!" My anxiety was that I would have to go back to my room with nothing to show for this effort.

I crossed my legs and let the skirt slip up to show most of my leg. Then it happened. A gentleman of about fifty, nice hair, medium build, a little overweight, barely taller than me and with a pleasant but not attractive face sidled up next to me. He at first only looked at my exposed leg. He wasn't trying to hide the fact that he was ogling me. There were so many things I didn't understand but I knew it gave me a thrill to have a man I didn't know staring at my body.

He ordered a drink and sat. His eyes moved to my large breasts. I found myself wishing I could show him more of my new breasts. I felt moisture between my legs. I desperately wanted him to say something about my new body. After a lot of staring he said, "May I buy you a drink?"

I smiled at him, something I had to still think about. "Yes, thank you so much that would be nice." I spun on my stool to give him a better look at my exposed legs. I knew the dress was covering my panties but not by much. He seemed to appreciate the view. I forced a smile. I so hoped it didn't look like a scowl.

He said, "Do you come here often?" Probably the oldest opening line in the world. But for me it was new. I was thrilled.

I knew then I should have put more thought into a story. I mean I can't tell him the truth. So, I decided on, "No, this is a new place for me. You?"

"I'm in sales, so I often stay at this hotel."

My drink came so I raised it and said, "Here's to us."

He smiled and said, "I'll drink to that."

He then said, "Where do you usually go to drink?"

Again, I needed to be better prepared, "Oh just around. Nowhere in particular."

"Are you free-lance?"

I was confused but said, "Yes."

He said, "Good, that makes it easier doesn't it."

I said without having any idea what he was talking about, "Yes." I needed to change the topic. "How do you like the city?"

"It is just another city. They all seem the same to me. One bar is like another. One sales prospect like another. After a while they begin to run together. By the way, I am Mort. You?"

Again, completely unprepared, I said, "Mary." First name that came into my head. I had no idea where this came from.

He frowned as he sipped his drink and said, "You don't look like a Mary. You look more like a Sophia. Anyone ever tell you that you look like Sophia Loren?"

This time I gave him a genuine smile. "Aren't you sweet? I just wish I were that pretty." Without consciously doing it I reached down and pulled my dress up another inch exposing more leg. I leaned over just a little to give him a little better view of cleavage.

He waited until I finished the little show and said, "Oh, I think you know you are pretty. How could you not?"

We continued with this small talk until we both had a couple of drinks. By now I was a little tipsy. He was slurring his words. I realized he had been drinking for a while. I was beginning to form a new identity. If I had just made up a better story in advance this would be easier. It was almost ten when he said, "Would you come up to my room for a night cap?"

I said, "Sure, I would like that." My almost unused vagina gave me a nice pleasant thank you of fluid. It felt like my panties were damp.

He handed me a room key and said, "214. Give me five minutes before you come up." He said this like I would understand exactly why he wanted to go first. He didn't want to be seen with me. Then I realized that was exactly it. He didn't want people to know he was entertaining a woman in his room.

I got to room 214 and tried to decide something. Should I knock? After this hesitation, I scanned the card, it turned green and I entered. He was sitting on the end of the bed wearing only his tighty-whities. I froze. I wasn't sure what I expected but for some reason this surprised me. Maybe that we would talk first.

He said with a quizzical look on his face, "Well are you coming in?"

I nodded my head and said, "Oh yes, I sure am."

As I stepped into the room he pointed to the desk and said, "There is your drink and 400 dollars. I hope that is enough. I just want it straight."

I stopped and looked at the desk. There were four one hundred-dollar bills and a mixed drink sitting there. I picked up the drink and drank about half of it thinking about what was happening. It then dawned on me that he thought I was a prostitute and he was paying me to have sex with him. I looked at him again, overweight and even in this light not a very handsome man. Did I really want to have sex with him? Was Mort really going to be my first conquest? Should I take the money?

He said a little angrily, "That is all I can afford, Mary. If you want more then, just leave. I can't afford more, or my wife will find out."

I emptied the glass of strong liquid, smiled to myself and him, "Well Mort, I usually get more but I have invested the evening with you. It will have to be just straight."

Mort smiled back and said, "Good! Now let me see those tits. I have been wanting to see them all night."

I stepped in front of him as he sat on the end of the bed with both hands on his knees and slipped off my shoes. I reached behind me and unzipped the dress. As I slipped the dress off my shoulders it dawned on me I should have let Mort do the unzipping. I had to learn more about how to do these things. I had to work to get the dress over my hips. I should have taken it over my head. With some shifting and rocking of my big hips the dress dropped to the floor. I picked it up and put it neatly on the desk chair.

I was also wearing pantyhose with a tummy shaper. As I slipped my thumbs to remove the pantyhose, Mort said, "Well that is a first. Most hookers don't bother. I guess this is what the high end does."

It somehow gave me a good feeling that he thought I was a high-end hooker. I was happy to be able to get the pantyhose off without sitting in a chair, I put my hands on my hips and asked, "Would you like to take the bra off?"

Mort smiled, and I realized it was right to ask, "You do it but please do it slowly. Wish we had some music."

I again reached behind my back and unsnapped my bra. I glanced at him with my head facing down toward my breasts that were still being held in the cup. He was mesmerized by the sight of them being freed. I put one hand over the cups while slipping first one and then the other strap off my shoulders. I was holding the cups in place, giving him time to anticipate what my breasts would look like.

I looked him in the eyes and smiled. He could barely take his eyes off the cups in anticipation. I slowly allowed my hand to slide the bra cups off my large breasts. Now completely healed from the surgery they were a very full 38-F. What was better was how firm they remained even after the swelling went away. I still had the faintest red line between the nipple and breast crease, but it was so faint I thought it was inconspicuous. My areolas were a perfectly round two inches with pink nipples that stood out in the middle.

Mort was staring like he hadn't seen tits before. I finally said, "Are they what you expected?"

Mort said in a fog, "No. I have seen large breast before but none that stood out like those. Can I touch them?"

"Sure. For four hundred you get to both look and touch."

It thrilled me to have a man appreciate my new breasts. I was wet. I took a step closer. His hands lightly rubbed around my breasts. I closed my eyes and enjoyed the feel of a man's enjoying them. I looked down at his tighty-whities and his penis was sticking out.

I said, "It looks like you are ready."

Mort said, "Pull those panties off and I will show you how ready I am."

I stepped back, slowly put my thumbs under the elastic and slid the panties off my hips. I bent over at the waist to give him view of my dangling breasts. As I stood he got a good view of my naked body. His eyes went to my pubic hair. It was thick and black.

Mort said, "Turn around and let me see your ass."

I turned, giving him a view of my broad fat ass. I finally said, "How do you like my big butt?"

Mort said, "I love your beautiful ass. It has such a nice round shape. It is full but doesn't sag at all."

I twisted around to see him. He was smiling appreciatively at me. He had taken off his underwear. I stared at his penis. It seemed to be fully extended but I thought it was small. Since I had never really seen a penis, I couldn't be sure. When Mr. Freedman fucked me, it was dark. I didn't know what to do and thankfully Mort helped when he said, "Can I touch your ass?"

I realized he thought when he paid me only $400 that all he could do was to fuck me. Not fondle me. But I wanted to be fondled.

I said, "Sure Mort, I like you, feel all you want. You may also rub my pussy if you want to."

I stepped back to let Mort knead my big buns. It wasn't long before he was rubbing his hand over my dripping pussy. I had an orgasm just from him kneading my buns and rubbing my pussy lips.

Mort finally said, "Lay down I am ready to screw you."

I remember that I had a condom. I got it out of my purse and handed it to him.

He said, "Oh yeah, good idea. I had one I just forgot. I guess that makes you the pro."

I thought to myself, 'If you only knew how close to a virgin I am.' As he put on the condom, I laid next to him. He crawled on top of me and slipped his prophylactic covered penis into my drenched pussy. It felt so good to have a man's penis inside me. I had a nice orgasm as soon as he entered me. He was overweight and not in good shape, but he managed to rock back and forth on me enough for me to have a second orgasm. It helped that he was stimulating my sensitive nipples as he fucked me. I loved having a man's hand on my breasts. As I finished the second orgasm he began to grunt, and I could feel that he was cumming in the rubber. I spread my legs wide to encourage him to stay in as long as he could.

But as soon as he finished his penis shrank to nothing. The condom slipped off and dangled on the edge of my pussy lips. I sort of thought that was odd but a professional would simply pull it out and throw the used condom in the trash. I found myself wanting more. This wasn't nearly enough. I instinctively knew that he wasn't good at sex and I wanted more. But no matter if he had wanted another go I would have said yes.

Instead I slipped on my bra and panties. I decided not to put back on the pantyhose. Mort had his underwear on. I warped my arms around him and kissed him on the cheek. I was as tall as him. I said, "Was that $400 worth?"

Mort smiled at this unexpected intimacy and said, "Better than that. You are a gorgeous woman but a little strange for a hooker. How long have you been doing this?"

I smiled at him still with my arms draped around him, "Can you keep a secret?"

Mort said, "Sure, I have a wife that will never know about this, so I better be able to."

"You were the first."

"I thought so. You will make a lot of money at this. If I had it, I would have paid $1000 to fuck your ass. You have a magnificent ass. It is big, smooth and perfectly shaped."

I said, "Thank you."

I finished dressing put the $400 in my purse and said, "Good luck, Mort. Be good to that wife."

"Good night, Mary."

I walked back to my hotel. It was almost midnight and we had a full day planned the next day and I was worried that I drank a little too much. I set the alarm early, so I could go to the gym and burn some of it off. I went to bed and began to think. I realized that even bad sex, which I was sure that was, was still pretty darn good. My only regret for the night was that I didn't get more.

I confess to Proctor

I had a full day interrogating the principals looking for an Angel investor. I loved this work. I was very good at it. I could spot weaknesses from a mile away and had a good sense of people who could be successful. I was also very good at absorbing large amounts of data and drawing the right conclusions. I often surprised people with my ability to understand their data better than they did. At the end of the day I thought this was a promising opportunity. We set a follow up meeting in North Carolina in two weeks.

I took Proctor to his favorite restaurant in this city. Of course, he drove. After the night before I thought maybe I could convince Proctor to fuck me. Better said, I wanted to screw again, and I hoped Proctor would accept it as my retirement present. I mean wasn't that a very personal gift. Since it worked the night before, I wore the same cocktail dress but this time without pantyhose.

Proctor loved Thai food so that is what we had. Most of the evening we discussed our time together and what he planned to do in retirement. I didn't realize but he was turning 65 that weekend.

I said, "I can't believe you are turning 65. You just don't look that old."

"Thank you, Miss. In my profession, you have to stay in shape or it is dangerous. I know that I can't do this any longer. It wouldn't be fair to you if I did. You need someone younger."

"Oh, Proctor I am going to miss you so much. You know they have sent me nine potential replacements but none of them seem right."

"Not sure why not. I vetted them, and they are all qualified."

"I know. Ah, Proctor do you find me attractive?"

He looked at me funny before saying, "You are a beautiful woman. I have always liked you. You are one of the toughest people I know. I admire your character."

"Is that a way of telling me you liked me even when I was fat and ugly?"

Proctor laughed with me. "Yes, Miss that is exactly what I am saying."

"I have something I want to ask you, but I am afraid you will get mad. Are we friends enough to really trust each other?"

"Yes Miss, there is nothing you can say that will come between us so ask."

"Would you fuck me tonight?"

Proctor smiled at me and said, "Will I didn't expect that, but the answer is I would love to but won't. Please don't get your feelings hurt before I can explain."

I smiled at him, "I expected that answer and think I know why but please explain."

"I have several reasons. First, we are friends and being intimate might hurt our friendship although I doubt it. It wouldn't be professional. I take pride in what I do and screwing a client is just not advisable. I have been married to the same woman for close to forty years and she deserves better than that. I wish I could tell you I have never cheated but I can't. Lastly, I am nearly sixty-five and it wouldn't be that good for you."