The Dating Scene
Chapter 1

Copyright┬ę 2008 by DG Hear

Romantic Sex Story: Chapter 1 - A Valentines Day story about a man who figured he would never marry. Until a special woman came into his life.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic  


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."

Some of the guests asked about our relationship and she would tell them we were just friends. I was hoping for just a little more. I was sure she had feelings for me but I didn't want to push it. We have been out on three dates albeit Lynn has been with us. Things were going too good to mess it up now.

Lynn came up to me and I wished her a Happy Birthday and gave her the present. Whenever I talked to her, I always stooped down, whenever possible, and talked to her at an equal level. This time she put her arms around my neck and gave me a big hug and said thank you. It was a total surprise seeing she shied away from men in general.

I had met all of Mary's siblings and her parents. They were nice enough but seemed a little skeptical. I wasn't sure if they trusted me. I could feel the skepticism when talking with them. About half way through the party, Paul, her oldest brother asked if he could speak with me on the porch. Of course, I said yes, and we sat on a couple of chairs away from everyone.

"Jerry," he said. "I just wanted to talk with you about Mary. She's our youngest sister and lost her husband last year. She's been through hell and we were wondering about how you met her."

"Are you interrogating me about my relationship with Mary?" I asked.

"No ... well, maybe a little. We were just wondering about how you two met. We're just looking after Mary and Maria Lynn."

"If you need to know we just became friends. We met in my office. I work for the IRS and I did a tax audit and helped her get her taxes straightened out. She in turn invited me over for dinner and we became friends. We've been to the movies and the park a couple of times. I can assure you that I would never harm Mary or Lynn in any way."

"I'm sorry, Jerry. Maybe I came on too abrupt to you. We knew the two of you have been out a couple of times. Mary's told us a little about you and mentioned that you know about her past. There might be a few things you don't know. Let me explain and tell you a little about Mary's past. When she was growing up she was always on the chunky side."

"I'm not worried about her size," I exclaimed.

"Please hear me out," said Paul. "Mary never dated much. She had a lot of friends, mostly girls. She was always self-conscious about her weight. Anyway, when she was in her twenties she met Ray Barrett, her late husband. He was a truck driver. We never cared for him much; he was always arrogant and bossing Mary around. One day she came home and told mom she was pregnant, Ray being the father of the child.

"He told her that he would do right by her and marry her. Believe me, we all wish he never did. He was a horrible husband. While she was pregnant he called her a dozen names like cow, bitch, hog. I think you get the idea.

"After Maria Lynn was born Mary's weight didn't change much. Ray started having affairs and cheating on her. Mary mentioned to us that she told you about her past. What she didn't know was that Jim, our brother, and I went and found and confronted Ray in the bar. We had a very strong talk with him and told him if he ever hit Mary again he would regret it.

"He never hit her again that we know of but the marriage went even further downhill. Of course, he eventually got drunk and ran his pickup over an embankment, hitting a tree. They say he was killed instantly. We almost wish he would have suffered more."

"My God, she sure went through a lot, but what has it got to do with me?" I asked.

"After Ray's death, Mary never dated. She was asked out a few times but always turned the men down. In fact, one of the guys to ask her out was the one who did her taxes for her. When she refused to go out with him, he told her she owed twenty dollars to him for doing her taxes.

"You are the first man that she has ever invited over to meet the family; so of course you can understand why we were all skeptical. I'm sorry if I offended you in any way. It's just that we are trying to protect Mary and Maria Lynn. We believe that is why Maria Lynn is somewhat afraid of men. We think she saw Ray beat up her mother and it's in her subconscious mind somehow. She must feel safe around you the way she hugs you. The only reason I'm telling you this is Mary hasn't been this happy in years and we just want to make sure she isn't hurt again."

"Paul, I assure you that I would never hurt either one of them. You have my word on that. By the way, get me the name of that guy who did her taxes and I'll make sure he gets audited. If he accepted money from Mary, it's taxable income. We would want him to pay his fair share now wouldn't we?" I smiled.

Paul smiled back at me and as we had finished talking, here came Mary and Lynn out on the porch...

"We were looking for you two. It's time to blow out the candles on the cake. Maria Lynn has already opened her presents and was looking for Jerry. What were you two talking about anyway?" asked Mary.

"We were talking about you," said Paul smiling.

"Well, it better have been good," laughed Mary.

I just smiled and asked Lynn what she wanted to see me about. As usual, I stooped down to talk to her.

"First I want to thank you for the coloring book and crayons and drawing stuff. After my party I'm going to draw you a picture," said Lynn.

"Thank you, Sweetheart. I'll keep it at work in my desk where I can look at it all the time. What else did you want to ask me?"

"Will you go with me and mommy to the amusement park on Saturday next week? I got three tickets from Uncle Jim for my birthday. He said I could take a friend and I want you to go."

"Lynn, if I wasn't able to go, who would you ask to go?"

"Probably Billy. He's my cousin and was hoping I would ask him when I opened the present. He's eight years old."

"I'll tell you what, Lynn. I'll go but I will buy my own ticket. That way you can ask Billy and he can ride the rides with you and I will keep your mommy company. How does that sound?" I smiled.

"Great!" She gave me a big hug and a kiss on the cheek and ran in to tell Billy he could go.

As I stood up both Mary and Paul were smiling at me. I guess I handled the situation right.

After the amusement park date, we began to go places every other Saturday. Mary got every other Saturday off and it was a special day for the three of us. We went to the zoo, aquarium, movies and many other places. We were like a family on that day but Mary and I were never intimate.

I lived about a half hour away from Mary. I talked to her on the phone a couple of times a week but we usually only got together on our special Saturdays or on a few special occasions.

One week I had to audit a business near Mary's home. I decided to stop by and say hi since I was in the neighborhood. It was just beginning to get dark out when I knocked on the door.

Mary answered it. "Jerry, what are you doing here? It's a pleasant surprise. Come in."

"I had an audit around the corner and thought I would just stop by and say hello. Where's my little friend?

"She's at mom's. I have to pick her up in a couple of hours. I was just sitting here watching some programs I had taped and now catching up on. Come watch it with me. I'm watching 'Boston Legal' right now."

It was funny how Mary and I liked the same things, even TV programs. This was an episode where they wanted to become friends with benefits. I laughed when they talked about it. The show 'Friends' also had a friends with benefits episode.

For those who don't know what friends with benefits is, I'll try to explain. Two friends who are not romantically involved with each other agree to help each other sexually when either is in need.

I laughed and told Mary that I wish I had a friend with benefits. I could surely use one.

She looked over at me and said, "I could too. I'll be your friend with benefits."

"Are you serious?" I asked.

"Very!" she replied. "Only I have three stipulations."

"What are they?"

"One: you can't tell anyone. I would be embarrassed if anyone were to find out."

"I can do that, or not do that. You know, not tell anyone," I laughed.

"Two: I don't take birth control, so you must wear a condom."

"No problem."

"Three: you can't see me naked. There's no way I want you to see this fat body. I'll wear a skirt and no panties or if we're naked I want the room totally dark."

"Come on, Mary. You can't be serious. Look at me, I'm heavy too."

"I'm dead serious. You have to agree with all three or find another friend with benefits," she replied.

This was a giant step for both of us. There was no way that I would disagree. "I agree with all three clauses," I smiled. "When can we start?" I asked.

"Right now. I have to pick up Lynn in an hour. I figure that will be enough time for a trial run," she smiled.

She went into the bedroom and told me she would call for me when she was ready. When she called, I headed for the bedroom. It was dark with the only light coming in from the hallway.

"Turn off the hallway light and come in," she said.

I walked in and could see her silhouette under the covers. I stripped and got into bed beside her. I put on a condom that I always carried in my wallet, hoping to someday use it. This was the day I'd been waiting for. I began by kissing her. I could feel how nervous she was.

"Jerry, this is the first time for me since Ray's death. I'm really nervous so please be patient and gentle."

I kissed her some more and put my hand on her breasts. I did my best; kissing them in the dark was a little odd but they felt so soft. I put my hand on her mound and slid it further to her pussy and slid in a couple of fingers. Feeling how wet she was I then got up and guided my cock into her waiting very wet pussy and slowly pushed it in.

"My God, Jerry, you feel so big. You better go slow with that thing."

"So I'm told," I replied to her. "I'll go slow but I'll tell you right now I won't last long.

She was making all kind of moaning noises and I heard her scream out. I pushed my cock in as deep as possible and felt myself come. It felt great! When her spasms subsided, I got up and went into the bathroom to get rid of the condom. When I returned Mary was out of the bed and had her robe on.

"My God, Jerry, you really are hung," she said looking down at my cock. I'm going to enjoy being your friend with benefits," she smiled. "You better get dressed and leave. I have to take a shower and pick up Lynn. Right now I smell like sex."

She put her arms around my neck and kissed me. It sure didn't feel like a non-romantic kiss. My cock started to get hard again. I quickly got dressed before it was too late. Mary laughed and told me she would see me on Saturday.

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