Thank you to WanderingScot for editing this story. I hope you enjoy it.
I'm Jerry Jones. I'm twenty-six years old and work for an insurance agency owned by my girlfriend's father. Jennifer or Jen as I call her is twenty-four and a really good looking woman.
I have been working for Ben Wilkinson for three years now. He hired me fresh out of college. I have taken all the state insurance exams and am licensed to sell any type of insurance. I even took the Life Underwriters training course, (LUTC) and the CLU certified course as well as other courses that were offered. I wanted to be the best in my chosen field and worked hard to achieve it.
For the last two years I have been his best selling agent. We have eight agents in all in our office. According to my clients, I'm considered trustworthy and honest. I always try and do what is best for my clients. I found out a long time ago that if you take care of your customers, the finances will take care of themselves.
Some agents just looked at the commission and sold the policies that made them the most money. I was brought up to try and do the right thing.
I've sowed my wild oats in college and have been thinking about finding the right woman, settling down and starting a family. My mom always asked me when I was going to settle down, I was an only child. I've dated a few women in the last couple of years but even though the sex was good I didn't love them. Also, so many women are divorced out there and I really wasn't interested in a ready-made family.
Last year Jen came to work for her dad. She was a beautiful big busted woman and very easy on the eyes. Most every guy in the office probably had wet dreams about her. She had the looks and knew it, very sexy but yet had a really nice personality. I did think she flirted a little to much.
I guess one problem was she was daddy's little girl. Most men were afraid of Ben and some were married and already divorced, but I just saw him as the boss and did my job. I began talking with Jen and we became good friends at first. We talked a lot but she was still a little on the wild side for me. I'm not saying that was bad but I saw life a little differently.
We began dating and went to the finest of restaurants. After our second date we went to my place and had sex – no, it was more than that. I would say it was more of making love.
She spent the night and our kisses were passionate, we each did everything we could to ensure that the other would climax. I went as far as eating her pussy to a second climax after coming in her. I have never before eaten a woman after having sex with her. I wanted her to know I was interested in a long term commitment.
My feelings for Jen were strong. I thought was falling in love with her and she with me. I loved my job but knowing I could see her every morning before going out in the field made it that much better.
Even though we weren't engaged most people knew we were a couple. Jen still flirted a little but it was just part of her personality. The flirting wasn't overly sexual; she did make men feel good just talking to them. I had to admit I was a little jealous but she wasn't really doing anything wrong.
We still had our own lives and did the things we liked to do but still did many things together. I was somewhat of an outdoors man and like to golf and fish. Jen loved to ride on the boat but wasn't much into fishing.
Talking about a woman that looked good in a bathing suit, it was Jen. She attracted attention wherever we went. I have to admit I loved the way she looked and at first I loved it when men found out she was with me. After a while it began to bother me that other men would so often stare at her. She on the other hand loved the attention.
I had to wonder if we ever got married would I be going through life wondering if she would be faithful to me. I had very strong feeling for her but I've seen too many marriages fall apart because one spouse or the other began cheating.
It always starts as something innocent like a kiss under a mistletoe or swimming with friends. I guess I've seen too many of my friends and family break up and it bothered me so much that I wondered if I would ever take the plunge and get married.
Jen would often tell me how much she loved me and wanted to be with me. Deep in the back of my mind I had these doubts. Could we actually make a marriage work? Old Ben, her dad liked me and often told me that I could eventually become a partner. Jen was his only daughter and he knew she cared for me.
One day after a wonderful dinner and a night of dancing, I asked her to marry me. She said yes and we went to my condo and made love for hours. God, she was such a hot woman.
The next day I told my parents about us getting married and on Monday we went in to break the news to Ben. Everyone was so happy, well everyone except me. Deep down I still had doubts but I acted excited. I wanted to marry her more than anything but we thought so differently on some things in life.
We had many talks about our pasts before deciding to get married. I wanted our past life out in the open, not something we had to hide from one another the rest of our lives. I didn't want to hear some man in a restroom telling me what a good fuck my wife was in college.
I went first. I told Jen that I dated a lot and had sex with most of them. They were mostly party girls. I had only really cared for one girl but it didn't work out. I sowed my wild oats and wanted to settle down now and have a family. I've never been arrested but did catch the clap a few years ago.
I told her how much I loved her but I could never stay with a woman if I ever found her cheating on me. I promised her I would be faithful to her. I wanted to make our marriage work. I felt we shouldn't have secrets and I wanted to put my cards on the table before we would become engaged.
It was now Jen's turn. "Jerry, I love you with all my heart and soul. There is nothing that I wouldn't do for you. Are you sure you need to hear about my past experiences? It could end our relationship."
"If you aren't able to talk to me about your past, how will it affect our life in the future? I understand you went to a liberal college and probably did things you aren't proud of but we need to discuss it. We need to understand and trust each other. Jen, Honey, I understand it's the past and I can live with that."
Jen continued, " I was young and always knew I was good looking, always had the biggest boobs in class. I wasn't as wild as you may think. I flirted a lot but have only been with a few guys. Usually I was at a party and drank a little too much and well, nature took its course. I dated a couple of guys but wasn't real serious about them. One time in college they had a wet t-shirt contest."
"I had drunk probably more than I should and was convinced to enter it. I won first prize. I can't say it was wrong or that I didn't like it. It was a contest and I came in first place. I never told my dad, he's old school and don't think he would have approved, even though I won."
"Any other surprises you want to tell me before we agree to get married? Jen, this is our past not who we are today. We've grown up and have fallen in love. I don't want a ghost popping up from the past that could possibly ruin our marriage because either of us didn't know about it."
"Jerry, I'm not sure I can tell you this, it's not like the wet t-shirt contest. It's not something I'm proud of."
"Honey, I love you and will do my best to understand, we don't need to mention names, in fact I would prefer we didn't unless it's someone I would have to see regularly. Most all the women I have been with aren't anywhere around here so our chances of seeing them is rather nil. If we should ever see someone I've been intimate with, I'll tell you. I won't keep secrets from you."
"Ok, Jerry, this could be the one that breaks us apart. I do want you to know I'm truly sorry for these two days out of my life. I can't change it and will never forget it. It happened in my junior year of college. Three of my girlfriends and I took a three day cruise during spring break."
"The ship landed in the Bahamas in we wanted to go to the beach. They had two of them, one a regular beach and around the bend was a nude beach only. The other girls voted to go to the nude beach since we didn't know anyone and thought it would be exciting. I decided why not, I had the body for it."
"It was odd seeing everyone naked. We had to check in our clothes on our way in. They had chairs, blankets and umbrellas for the guests. They even had a mini bar set up and waiters came around for drink orders. They would just charge it to your cruise boat room."
"A lot of men came by and talked to us. It was exciting and seeing they were all nude it was easy to do some comparisons. I can honestly say, not all men are created equal."
"I knew we were drinking way too much. Many of the men sat with us and talked. We all knew it was going to happen. We were far away from home, nobody would ever know. We were going to have sex with these black men. Yes Jerry they were black."
Jen stopped for a second and I looked down. I loved her but how would I deal with this. I wasn't brought up with interracial sex. Sure I knew it happened a lot, it's just that I was never a part of it.
Jen looked sad or maybe it was mad as she told her story. "They took us to their tent set up further down the beach. This one big black man took me in his arms and kissed me. I was used to a little bit of love and tenderness but I didn't get that."
.... There is more of this story ...