A Man in Turmoil

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We were engaged but I knew we had a problem.
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DG Hear
DG Hear
5,673 Followers

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."

"He made foul remarks about my tits and squeezed them till they began to hurt and bruise. I asked him to be gentle and he laughed at me. He had me spread my legs and without any foreplay stuck his big black cock in me. He didn't care about me, he just wanted to fuck another dumb white woman."

"God, I'm so sorry Jen. What about your friends? How did they react?"

"One felt about the way I did. The other two laughed it off and said it was just another fuck. We knew we couldn't say anything. We went willingly to their tents and besides they lived on the island and we knew we wouldn't ever see them again."

"We stayed on the ship the next day and just hung out in the pool area and even saw a movie. We did talk about the black men and were surprised to have always heard how hung they all are. These four had nothing special going for them except how black their cocks were."

"Anyway, we all got over it and figured it was just one of life's experiences. One I wouldn't care to repeat. So Jerry, are we still engaged or going our separate ways?" She said it very softly and tenderly. I could tell it was hard for her to tell me about the nude experience.

"I'm going to leave it up to you. I have one more story to tell you and I'm not proud of it. It's the worst thing I have ever done. I have never told anyone, not even my parents. In my junior year I was going with a girl named Brenda. She was one girl I had strong feelings for. We dated and in one night of passion she got pregnant. When she told me I told her I couldn't get married. I was just trying to get my life in order."

"We talked and argued about it over and over. I might have really loved her but our life was just beginning. I gave her four-thousand dollars to get an abortion. She agreed it would be best. It was time for summer vacation and I told her I would be there for her and to call me. I never got the call."

"The following year she never returned to our school. I felt bad because I did care for her. I tried to get hold of her with whatever numbers I had but never located her. I just hope her life turned out to be a happy one."

"Oh, Jerry, I'm so sorry. I believe you did the right thing."

"Did I? Jen I want a wife and family and I had my own child aborted." I sat and cried for a few minutes.

"Well, I guess we both opened up the ghost closets. Are we going to stay together?" asked Jen.

"As long as our pasts aren't repeated, I have no problem going on and having you as my wife." We kissed and Jen started planning our wedding.

Life was going good for us. Sales were fine, my future father in law and I got along almost as father and son. I saw Jen every day, and we were actually talking about moving in together. It was one of those things I wasn't quite sure about yet and wasn't sure how her father might react. He was even more old school than I was.

Our lives went on during the wedding planning stages. My parents liked Jen and thought we would make a nice couple. At times I did have to wonder if my parents were just saying that because they wanted me to settle down and give them grandchildren.

I golfed and went to the local Elks club where I belonged. You pick up a lot of leads when you belong to organizations. Jen had her girl friends and they went out shopping, to movies and sometimes even a girl's night out. She promised me that they would never pick up men. Her girlfriends were all married and I knew their husbands.

I honestly had no reason not to trust her. Our whole relationship was built on trust and communication. That was why our earlier talk about our pasts meant so much.

Sometimes we would get together with friends for a yard party or other occasion. There was always flirting going on among friends but it was all mostly talk. All the women in our group had great bodies. When we went swimming it was hard to keep your eyes off the women.

I honestly have to say that I didn't know if any of the women cheated on their husbands. A couple of the guys I wasn't sure of but if they did they did it secretly. They would also be stupid to cheat in their marriage. All the women were very sexy and very nice.

I later gave it some thought and found it odd that most of our friends were all old friends of Jen's. She had introduced me to all of them. Two of her girlfriends went to the same college as her. I had to wonder if either of them went on the cruise with Jen. We never mentioned names. It was just a thought that entered my head.

I don't know who brought it up but someone said we ought to all go on a cruise together. The first thought in my mind was what Jen had told me. It's just something you don't forget.

Bob said, "Hey, I hear that most cruises even go to a nude beach."

His wife Mary said, 'If I find you at a nude beach checking out the women and that thing between your legs get hard, I'll cut it off." Everyone started laughing.

Joy said, "Howard and I went to a nude beach once, years ago. I have to say it was interesting but not a sexual turn on like you'd expect. I think most of the men would have looked better in clothes. Now Howard might have thought differently the way he attacked me when we got back to the room."

Jen smiled but didn't say anything about her adventure, thank God.

Terry asked Jen and I if we thought it would be fun to go on a cruise. We were the only unmarried ones.

"Well maybe after we get married. I don't think Jen's dad would think kindly of the idea until after we were married. I do believe could be fun though," I added.

Terry's husband Jim said, "I think Jen might be quite popular on a nude beach. I sure would like to be there." he laughed.

Terry hit him on the shoulder and called him a dirty old man. Jen definitely had the nicest body and largest breasts of the group.

"If we did go on a cruise, we wouldn't be going to a nude beach," I said. I'm a little too jealous to have my wife showing her body to anyone but me." I tried to say it with a smile but I really did mean it.

That was about it for that night. It's funny how things in the past seem to pop up. I'm so glad Jen and I had our talk.

We went out with our friends fairly regularly. We took turns on finding places to go. It was only two weeks before our wedding when Howard said he found a nightclub that he thought would be fun. We all got dressed up and went to Howard's place of choice.

It was a really big nightclub that would hold hundreds of people. We started off with dinner and drinks. Everything was fine until I saw a sign posted. At ten o'clock they were going to have a wet t-shirt contest. It made me think of Jen saying she won one in college.

We danced and drank but no one had brought up the contest. I have to admit that everyone probably had a little too much to drink. The manager came around and asked if anyone was interested in entering the contest. First prize was five hundred dollars, second was two hundred and third was one hundred.

Howard laughed and asked his wife Joy if she was going to enter? She blushed but said she might if any of the other wives did. She said it would be fun even if they didn't win they got the free t-shirt.

Jim asked Terry if she was going to enter. He told her she had a great set of boobs and probably had a good chance on winning.

"Jim, I wouldn't have a chance once they saw Jen's. Hell, she would win hands down." Jen was smiling from the compliment she was just paid.

"Jen's not entering the contest. I don't want her showing her tits to the world."

Jen look at me with a dagger like look. "You're not my boss and you can't tell me what I can and cannot do. We're not even married yet and already I need your permission?"

"I'm sorry Jen, I just don't what a bunch of strange men staring at your tits."

"Jerry, I hadn't planned on entering it but since you think you can tell me what to do I'm going to enter the damned contest."

I sat there not knowing what to say. I watched as Terry, Joy and Jen signed the consent form. Mary said she would have done it but she was just too old. I asked Jen to step away from the table so we could talk.

"No, as you say we have nothing to hide."

"I'm going to ask you one more time, please don't go through with this." I hoped she would change her mind but she was getting up with Joy and Terry to go get their t-shirts.

"Jen, if you go through with this damned contest, our wedding is off!" I said as a last resort.

"You wouldn't cancel a marriage because of me showing my tits!" she said as she was walking away.

"Calm down Jerry, it's not that big of a deal, the girls are just having a little fun. No one is going to be touching them and we're right here," said Howard.

"Look, I don't give a rat's ass that you don't care who your wife shows her tits to. I'm not into exhibitionism. I don't want a wife who cheats, or thinks it's ok to show her body to any Tom, Dick, or Harry. If she shows up on that stage in a t-shirt, we are through."

The guys kept quiet and drank their beer. We were waiting to see what would happen next. Howard talked to one of the servers and was told there would be fifteen women in the contest and it was just about to start. We looked up and we saw Joy, Terri and Jen all come out smiling. They all had on very thin white t-shirt and no bras. I could already see the outline of Jen's breasts.

Everyone in the lounge was cheering. I felt like I was going to throw up and left for the men's room. I washed my face with cold water. I stayed in the men's room for a good fifteen minutes. I walked out and walked to the back of the lounge and watched the contest.

My friends at the table didn't see me but seemed to be enjoying the show. I had to wonder was it was me or did the values of married people drop that much. I put it all out there and lost. There is no way I could take Jen back now. What kind of marriage would that be? She would just do what she wanted and would expect me to just take it.

The crowd was now yelling for their favorites. There were five women left on the stage. Jen was one of them. Joy and Terri were eliminated. There was another round of the final five. The t-shirts left nothing to the imagination. They might as well not have worn anything. In fact all five, including Jen took off their shirt.

Jen kept shaking her boobs and laughing. I was in the back nearly crying. The final vote came in and Jen came in second. Our friends at the table all stood up and applauded and whistled at her. It was times like this that I wonder if they might have seen her topless or nude before. They were all friends of hers before I came into the picture.

DG Hear
DG Hear
5,673 Followers