The Dating Scene

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Not everyone has the perfect looks.
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DG Hear
DG Hear
5,674 Followers

Thank you to my two favorite editors, LadyCibelle and Techsan, for making my story a much better read.

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Chapter 1

There are many men out there; they are all sizes and shapes, tall, short, heavy, trim. Some have a full head of hair while others are nearly bald. Women have a tendency to look at the young, good-looking ones with a body with six-pack abs and a tight butt. Who can blame them? Most guys look at the good-looking sexy women in short skirts and big boobs. It's just part of life. Unfortunately, I don't fall in any of the sexier categories.

I'm a male, on the short side, pudgy in the stomach region and almost completely bald, having hair just on the sides of my head. I'm thirty-five years old, but look forty-five and single. Geez, what a surprise!

I'm not dumb or overly shy; just not the best looking guy on the planet. I graduated in the top five percent of my class in college. I hold a masters degree in Accounting and a bachelors degree in Business Management. I work for the IRS (Internal Revenue Service), so I don't have a lot of close friends. Everyone thinks I'm after them; which is not true.

I live at home and take care of my mother. My father passed away a few years ago. I know it makes me sound like a mommy's boy but it's not like that. We do have a wonderful mother-son relationship and I do what I want to do. Mom has her own circle of friends, mostly gossiping older women. They are always trying to fix me up with their daughters, nieces or other women they know. Most of my dates only last for one or two dates.

I guess the mothers and others realize that the beauty is only skin-deep. Financial responsibility is more important. Of course, you have to get by the looks first. I do understand that.

The compatibility with the sexier women and me just isn't there. Many of the women are just trying to find a husband, or at least someone to take care of them, while others want to get laid. I know it's hard to believe but it is true. I may be short and pudgy but my member is not considered short. I guess word got around when I was in high school. The short guy with the long dong. It took a long time for me to overcome the embarrassment.

I dated rather sparingly ever since high school. Sometimes it just wasn't worth the hassle. I thought I was in love a few times but it always ended badly. My problem is I used to go after the good-looking girls. I got turned down many times but also had a few dates. It was kind of like a joke I heard long ago.

"A man stood on the corner and asked the good looking women that walked by if they would like to sleep with him? It was just the law of averages. He said he got slapped a hell of a lot of times but he also got pussy once in a while too."

My dating was kind of like that. Maybe one in ten women I asked out said yes. Maybe one in three of those went out for at least a second date. Those that I became intimate with stayed around for a while.

Sherry was my first love. We were in college when we dated. Our dating ended abruptly after about five months. We met when I became a tutor and helped a lot of the students out. Sherry and I became close. My friends couldn't understand how a short guy like me was able to date a gal like Sherry. She really was a looker. Our sex life was great. Oral, missionary, from the rear, it didn't make any difference. The only thing we never did was anal. We tried it once and it hurt her too much. To be honest, it hurt me too; so we decided against it. Other than that, our sex life was great.

Looking back on our relationship, I guess sex was all we really had together. We went to a few sporting events and a few movies. The sex was great, but I guess it takes more then fucking to sustain a real relationship. I told her I loved her every time we had sex. It would just come out. I feel that at that very moment when a man comes, he truly is in love, but that's only for a few minutes in most cases.

I remember her telling me how much she loved the way I fucked her, but I honestly can't remember her telling me she loved me for me. I guess I just heard what I wanted to hear.

One weekend I told her I was going home to see my family. When I called home, my parents said they wouldn't be home on Saturday, but I was welcome to come home anyway. I didn't see the point of being home alone so I went over to see Sherry. She lived with three other girls. They each had their own bedroom but shared the living room, kitchen and bathroom.

When I got to the house Sherry's roommates had already gone out. They were all pretty, good-looking gals and heavy daters. I could see Sherry's room from the street and her light was on. I figured she was studying or something. I looked under the flowerpot for the extra key. It was for any of the girls that might have misplaced theirs.

I unlocked the front door and replaced the key. I walked to Sherry's room and could hear moaning noises. I quickly opened the door and there laid my Sherry, naked on the bed, lying on her back with her legs nearly straight up. A big guy was pounding the hell out of her pussy.

She kept yelling, "Lord, I'm coming! I'm coming!" She probably would have gone if this big galoot weren't holding her down.

Sometimes I have to crack an old joke to get by my pain; it softens the blow. Anyway, Sherry looked over at me and I could see a quick tear in her eye. The guy told me to get the hell out and I closed the door and left. I wish I could say I beat the shit out of him but no use lying. He was way bigger than me, and I could tell Sherry was a willing participant

I went home and sulked. The next day Sherry called me and said she was sorry. She thought I was out of town. I told her that I couldn't be with a woman who would treat me like that and we never dated again. For spite, I did date two of her roommates a couple of times. It was just for the sex. I guess she had told them I was hung. It still hurt when I saw her dating other men. I really thought we had something going.

I started losing my hair during my college years. Once out of college. I started getting pudgier. I guess I liked eating more than exercising. I had another serious relationship with a good-looking woman named Brenda. She was recently divorced and I guess I caught her on the rebound. The relationship lasted over six months before her ex came back into the picture. She had a son who was five years old. I really liked the kid; I often pictured myself as a dad.

Brenda told me she really cared for me but that she was thinking of going back with her husband for the sake of their son. No matter what I said, I couldn't convince her otherwise. We parted as friends but I couldn't see her again. Her husband made sure she cut all ties with me. I felt I lost a family.

As I mentioned earlier, I dated women I had known or who I was set-up with by friends and neighbors. When women looked at me, they didn't see past the exterior. I was neat and clean but I was far from the tall, dark, and handsome man that most women wanted. Short, bald and pudgy wasn't on most women's want list.

Life went on and I did have a good life. I figured I would probably die a bachelor. That is until Mary came into my life. I'm not quite sure how to put it. I've heard of love at first sight but I never thought I'd experience it. To this day, it's still hard for me to believe.

It was June and Mary came in for a tax audit. I could tell she was scared to death. She was almost in tears when she came into my office. I have to say that I really felt sorry for her. I get a lot of people who are scared. I've even been offered sex if I would look the other way. I never did it with a client; in fact, I never dated a client I wasn't about to lose my job over a piece of tail.

Mary was different. I'll try to explain but it will be hard. Mary was a pretty woman but quite a bit overweight; probably weighed more than me. She had shoulder length dark hair, pudgy face but beautiful eyes. She was short maybe 5' 1' or so, very large breasted and somewhat self-conscious. When she came into my office she was almost in tears. She was very emotional. When I first saw her, I felt my heart jump. Looking at her eyes, it was as though I could see her heart.

"Please sit down, Mrs. Barrett," I asked. "I'm Jerome Speck; I've asked you here to audit your income tax from last year."

She started to cry. "I didn't do anything wrong. Why am I here? I filed my return and was told I was being audited." I could see her head shake; she was really scared.

I got up, went around my desk, and put her little pudgy hand between mine. "Mrs. Barrett, you aren't being accused of wrongdoing. The tax return you filed for last year was different from the returns you filed the last five years. It brought up a yellow flag and we called you in to talk with you about it."

I was still holding her hand and sitting on the corner of my desk when she replied. "My husband died in January of last year. It's just my six-year-old daughter, Lynn, and me now. Maybe that's the problem?" She calmed down a little.

"It says on your tax form that your daughter's name is Maria." I questioned her.

"Her given name is Maria Lynn Barrett. Since my name is Mary we call her by her middle name which is Lynn. It stops a lot of confusion."

I went back around and took my seat at my desk across from her. She looked like she was pleading with me for help. Why couldn't I take my eyes off of her? Like me, she didn't look special at all but I was feeling it in my heart. Was it even possible?

"Mrs. Barrett, you didn't file a return for your husband. This return lists you as head of household with one dependent. It also shows you receiving Social Security for your daughter."

"I don't know anything about taxes. One of our managers at work said that he would fill out my tax form for twenty dollars. It was a lot less than the hundred dollars the agency wanted for filling it out. He said I just needed that short tax form and would get back over a thousand dollars. I thought it was too good to be true, but I did get twelve hundred dollars in April of this year and spent it catching up on my bills.

"What am I going to do? I don't have the money to pay back. Will you let me make payments?" asked Mary.

"Easy, Mary, we're not all bad guys here. We just want to make sure your taxes are done correctly. You should have filed a joint return with your husband and sent along a death certificate. You see, since he died any time after January 1st any money he made last year should have been on this return."

"What can I do? I'm scared! I didn't mean to do anything wrong," replied Mary.

"That's why I'm here. I can redo your taxes using the right form and we will amend last year's return. Did you bring the information we asked you to bring along with your husband's death certificate? I am sorry to hear of your loss. What was his cause of death?" I asked trying to put her a little more at ease.

"He was a heavy drinker and was drunk and drove into a tree. I knew that someday it would happen. He wouldn't listen to me. He went out drinking almost every night. Oh, I'm sorry; I guess I talk too much. Here are the papers you asked for. Ray, my husband, died on January 22. He only made a little over a thousand dollars last year."

I started filling out an amended 1040 tax form. I asked Mary to verify all the questions. When I got down to earned income credit, she had no idea what it meant. She was entitled to forty-two hundred dollars in earned income credit alone not counting other deductions she had. I wrote in the figure and continued with her return.

For those who don't know about the credit, the government gives a tax break for low-income families with kids. It is a refund even though the taxpayer never paid it in.

I finished the form and found she was entitled to a total refund of six-thousand dollars. I subtracted the twelve hundred that she had already received. I looked up at her and told her the amount; forty eight hundred dollars.

"What?" she said. "I don't have forty-eight hundred dollars. What am I going to do? They can't put me in jail; I have Lynn to take care of. Please help me," she said.

"Mary, Mary, stop crying. You don't owe the government forty-eight hundred dollars; they owe it to you."

"Me, they are giving me forty-eight hundred dollars? Why? I don't understand."

I went back around, held Mary's hand, and did my best to explain the earned income credit to her. She was crying and all of a sudden, she gave me a hug.

"Thank you so much. What do I owe you?" asked Mary.

"You don't owe me anything, Mary. I'm just glad I could be of assistance to you."

I found myself still holding both of Mary's hands. I felt something, just touching her. I've never felt it before. It was like the little shock you get when someone slides their feet on a carpet and touches you.

Mary looked straight into my eyes and asked, "Since I can't pay you for helping me, can I at least make dinner for you?"

She was looking at my fingers and noticed I didn't have a wedding ring on. I have been at the IRS for a goodly number of years and have never dated a person I had audited or was about to audit. For some reason, I couldn't refuse Mary.

"Yes, Mary, I think I would like that." She started to give me her address when I held up her amended tax form. She knew I had all the information I would need. I made a date and squeezed her hands. She smiled and left the office.

-----------------------------------------

When I got home that evening, my mom asked me why I was so happy. She said for some reason I seemed different.

"I met a woman today. After auditing her taxes, she asked me if I would come to her place for dinner Friday. I told her I would."

"Jerome, I thought you never dated women that you audited?" asked my mother.

"I never have Mom. This will be the first time; that's why it feels so good. The rules are you can't date a person who you are about to audit. Mary's - that's her name, Mom - Mary's audit is finished. She has a young daughter who is six."

"I'm worried about you, Jerome. You've been burnt so many times and I hurt for you every time. That Brenda woman was divorced and went back to her husband. I'd hate to see you hurt again."

"Mary's husband was killed in an auto accident in January of last year. I don't think she'll be going back to him too soon," I replied.

"Just promise me you'll take it slow and not rush into an affair," said mom.

"I won't be rushing into anything, Mom. I just feel that we connected in a small way. I have to know for sure, Mom. I promise to take it slow.

I went to dinner at Mary's on Friday. She lived in a modest apartment. When I knocked, on the door, she came to the door dressed in a pair of slacks and a nice blouse. Behind her was her daughter staring at me.

"Lynn, this is Mr. Speck. Remember I told you I invited company over to have dinner with me and you tonight?"

Mary looked toward me "She's shy around strangers. Other than her uncles, she doesn't go to any men."

I stooped down and said hi to Lynn. She gave me a quick smile before running into the other room. I felt a bit uncomfortable since I really didn't know much about Mary. She asked me to sit down and asked me if I would like something to drink. I told her a beverage would be fine. She went into the kitchen and brought us both back a soda.

We sat on the couch and talked about things in general and watched Lynn draw pictures. She would constantly look up at me and smile. I made sure I smiled back and complimented her on her drawings. Lynn kept calling me Mr. Speck; I told her to just call me Jerry, because it would be much easier and a lot less formal.

Eventually, we all went into the kitchen and had a nice meal. Mary was very cordial the whole time but I had to wonder if she felt the same stirring in her heart that I had felt.

After dinner, I got ready to go home. I told her I had a lovely time and thanked her for inviting me. She said we needed to do it again sometime. Of course I agreed, but wasn't sure if she meant it or was just being courteous. Lynn held out her little hand to shake mine and thanked me for coming over. She handed me one of her drawings and told me she drew it for me. On the top, she printed "For Jerry." I squeezed her little hand and thanked her, then went on my way.

I felt good, but of course unsure. For the next week, I wondered if I should call Mary or just let it go and see if she would call me. Then, one day the phone rang. It was Mary.

"Hi, Jerry. I haven't heard from you and wondered if everything was all right. Maybe, I'm out of place calling you..."

"No, you're not. I've been thinking about you all week. I was wondering if you would like to go to a movie this Saturday. If you like, Lynn can come too. You can pick the movie," I replied.

"We'd love to go. There's a movie I promised Lynn I would take her to see. She talks about you all the time and asked me when you were coming back over for dinner."

We did go to the movies and out to eat. We started going out fairly regular. After about our third date I asked Mary about her past and she told me about her life after Lynn was born.

She told me Ray started having affairs and cheating on her. She did her best to try to keep the family together because of Lynn. Ray drank way too much and would flaunt his affairs to Mary. One time when she told him she was going to leave him, he slapped her around. She had bruises on her arms and legs.

She was thinking about leaving him but thought she would give him one last chance after he apologized. It wasn't long after that he was killed in an accident.

I told Mary about my past but not of all the affairs I had. Just the two that I thought were special relationships. One cheating on me and the other going back to her husband. We decided to be good friends for now. I had strong feelings for her but I wasn't about to push it.

One day I received a surprise phone call. It was from Lynn.

"Jerry, is that you?" she asked.

"Hi, Lynn. Yes, it's me. How have you been? Are you still drawing pictures? I have the one you gave me here at the office."

I really did have it in the top drawer of my desk. "What can I do for you, Sweetheart?"

"I'm having a birthday party Saturday. Can you come? Mommy said I could ask you. I'm going to be seven years old."

"Yes, Sweetie, I'll be there. Is your mom there? I need to ask her about what time to be there and a few other questions."

"Okay, I'll give mommy the phone. I'll see you Saturday. Bye!" I heard her yell in the background, "He can come Mommy."

Mary got on the phone and we talked about the party. She said it would mostly be her family there. She had two brothers and a sister and their kids. Also, her mom and dad would be there. She told me that Lynn asked if she could invite me. For some reason, Lynn really liked me. When I asked about what gift I should buy, she told me anything would be fine. As long as it was wrapped, Lynn loved to open presents.

I felt good after hanging up. I still wondered a little about her telling me it was Lynn's idea to invite me. I did realize that I was going to meet Mary's family. That must mean something.

I stopped at the store after work and bought Lynn some coloring books and crayons. They also had a drawing kit, which I picked up for her. It had lots of paper, pens and lots of markers. I knew she would love it.

------------------

When I arrived for the birthday party, I noticed there were quite a few vehicles there. Mary greeted me at the door and gave me a light hug and thanked me for coming. She told me that most of the people there were family. She took me by the hand and introduced me to a lot of the people. She would say, "This is a good friend of mine; his name is Jerry."

DG Hear
DG Hear
5,674 Followers