My Neighbor Jessica

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Mature divorcee meets younger neighbor at new apartment.
14.9k words
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This is an "edited" version of the very first story I submitted to Literotica. If you compare the dates, it may not appear to be the first, but I submitted two stories just one day apart and both were rejected for the same reason; two speakers (or quotes) in the same paragraph. When I edited them and resubmitted, for some reason "Tale of Two Strippers" was posted before this one.

With 53,000 reader viewings, numerous critiques and comments by readers and other writers as well as countless re-reads and astonishments at mistakes, I just cannot believe I made, I decided the story deserved a little "clean up!" Now I know, this becomes an open invitation for you to point out other and additional mistakes I failed to address. Please proceed! I have a relative thick skin in these matters and if required, I will edit and resubmit once again.

This is a true story of something that happened just before by 55th birthday. Maybe if not for the age difference, the event would be commonplace for many younger men, but for me it was a true serendipitous experience. Obviously, the age difference is what prompted me to place it in the "Mature" category.

First a little background about me. I was born and raised in a small community in the northern portion of a gulf coast state. My parents, though honest and hard working were uneducated, naive and their social skills were more along the lines of the Beverly Hillbillies than Hugh Hefner. I was raised as an only child and attended a very small public school where all twelve grades were in the same building and sometimes two grades were in the same room.

When I was in Jr. High, we moved into a huge town of 8,000 people and moved into a rent house much larger than the small 3 room home where I had always lived. In one fell swoop, we had our first indoor plumbing, first television set and first telephone. I was enrolled into a school where the 7th grade took up several classrooms. I had to take my text books from one class to another and actually store them in a locker when not in use. I was required to keep school papers in a notebook for the first time and was required to make corrections for mistakes on the back side of the previous page. All of this (and I mean everything named in this paragraph) was brand new to me and needless to say, I was overwhelmed. Looking back, I really wish some of my teachers would have recognized I was overwhelmed by this tremendous change in my life; Instead of just considering me either dumb or lazy.

My parents were so poor that my mother actually made some of my shirts. She knew nothing about style and my dress pattern showed it horribly. When Dolly Pardon sang "Coat of many colors" I knew exactly what she was referring to. Kids at 12 & 13 years old can be cruel and insensitive; therefore I was the butt of numerous jokes and quickly developed an inferiority complex that was difficult to suppress for a really long time.

I dated very little during high school, partly because of the lack of a car, but mostly because of the lack of confidence. By the time I was a senior in high school, I was able to buy my own car. Although it was 10 years old, the 56 Chevy was popular among car junkies and my mechanical ability and knowledge gained from working at the local Chevrolet dealership part time, generated an acceptance never before experienced.

I suddenly found myself being sought out by popular teenagers and even some guys in their 20s wanting advice for mechanical questions or wanting me to work on their cars. Where popular boys hang out, you will also find popular and good looking girls. In mixed groups or with "the guys," my acceptance and abilities put me in the lead roll many times, but when one-on-one with the girls, my lack of confidence would hinder my ability to do much more than stutter and carry on a lame conversation. Not many girls were interested in which carburetor/manifold combination worked best on the 327 Chevy or where to locate a good 4 speed transmission along with the proper clutch and bell-housing.

I finally started dating a pretty girl four years younger than myself and we married soon after she graduated high school. We had one daughter and ended up divorcing after almost 18 years of marriage. I would spend more time describing my first marriage and might in another story, but it has very little contribution to this one.

I was single for four years and spent much of that time traveling in my business, which was by that time, commercial construction management. My travels literally took me coast to coast and border to border. This provided some experiences I must share in other stories, but I will try to not get sidetracked here.

Then I moved back to my home state and met a girl, 22 years my junior. After a whirlwind affair like nothing I had ever imagined, we marred when I was 43 and she was 21. We stayed married for 11 years and I must say, most of the inexperience and naivety that remained from my youth disappeared. From the very first night we were together, we experienced the kind of sex you read about in these stories. She was not shy and would express her wants and desires at some of the most surprising times and to almost anyone at anytime. She was multi-orgasmic and a screamer. Blowjobs while driving, sex in public places like grocery store or night club parking lots or outdoors where we could be caught was not at all out of the ordinary. Later when we had a home with a pool, midnight skinny dipping and sex in the lighted pool or attached spa was commonplace.

By that time we were living in a major metropolitan area still in the same gulf coast state. Like with my first marriage, I could spend a lot of time and write pages about this marriage, but it also has little contribution to this story other than erasing my naivety. The marriage did produce two beautiful daughters. The first one was planned and was born when I was 48. The second one was not planned, at least not on my part, but now I would not trade her for anything in the world. She was born when I was 51 and there is always some conversation with people I see for the first time, about whether the girls are my daughters or my granddaughters.

When this wife and I separated, I moved into an apartment in a pretty nice part of town, not the most expensive but nothing to be ashamed of either. I moved on Saturday and as soon as I got everything moved inside, I went to check out the mailboxes, pool, laundry room, vending machines, etc.

As I walked toward the mailboxes, someone called out to me and as I turned around was met face to face, but separated by several feet, with a young lady who obviously had some difficulty in standing and walking. She was half dragging a laundry bag and asked if I knew if there was a laundry on the premises.

Because I had just seen it, I confirmed there was indeed a laundry and asked if she needed help getting her bag there indicating her lame foot or ankle.

She accepted my help and said she had turned her ankle the night before. She indicated a red Pontiac Sunfire with a space-saver spare on the right rear and told me she had a flat and turned her ankle while changing her tire. She asked me if I knew anything about cars.

I said I knew some, but didn't really elaborate.

She limped toward the car's hatch back and opened it to show me a full size tire with a badly bent rim. She wanted to know if the wheel could be repaired.

I said I thought it was beyond repair and would need to be replaced.

Her expression of "shhhiiit" was the most improper thing said during that brief meeting.

After taking her laundry to the washing machines, I went on my way as she indicated she could handle it from there and thanked me genuinely for my assistance.

By the next weekend, I had my apartment set up the best I could. I had all my utilities turned on and furniture arranged. I had bought a new computer and set it up on a desk in the breakfast area I was to use as my new "home office."

I also had my two kids that weekend. They were age 3 and 6 at this time and after I got them to the apartment, I realized I had nothing to entertain them. I had made two or three trips to the nearby office supply store, so I thought I could go there and get some colored pencils, crayons and such, along with some art paper and keep them entertained most of the time.

As we were leaving the apartment, that same girl was driving by in the red Sunfire. I had gone to the passenger side of my truck to fasten the seat belt harness for the three year old and was on my way to the driver's side just as this girl was slowing down for a speed bump. I smiled and nodded a "hello" as she was moving past and was surprised when she stopped and rolled down her window.

She asked if that was my girls.

I told her it was and volunteered our destination.

She replied that she did not have her kids that weekend and she had a full box of crayons and several coloring books which she absolutely insisted she get for my girls.

Although I did not feel the offer was necessary, it was obvious she really wanted to provide this help. I somehow figured all this was in repayment for befriending her that first day and helping her get her laundry bag to the washer/dryer room. I have learned that if someone genuinely offers their help, it is an insult to them if you refuse it.

I told her, "That would be fantastic" and told the girls there had been a change in plans. I told them, that was my new neighbor and she had volunteered to get them some coloring books. We got out of the truck to follow her toward her apartment as she retreated in her car. By the time I had helped the three year old out of the seat belt and seat, this girl had time to get to her apartment, get the coloring books and crayons and meet us somewhere close to the rear of her car.

I thanked her and the girls thanked her.

She said "You're welcome" and that my girls were "so cute!"

The next weekend that I had my girls, she also had her kids, a boy and a girl, and the four of them played some on the lawn of the apartment complex. Nothing significant happened that weekend or for the next several weeks.

I was busy with a couple of business deals and was working some long hours. I would run into the same girl occasionally but I was so preoccupied with the other things I had going that I didn't ever think about her unless I actually saw her. However in bits and pieces over that next few weeks, I did learn that she lived alone except the weekends when she had her kids. Most the time they lived with her parents. I did not question that arrangement but in putting the little bits of information together, it seems she had separated from her husband who was by now in Iraq. She was from a very small town, several miles away and had moved into the larger city to find a better paying job. I assumed her parents were helping out by keeping her kids until she got established. I really had no interest in her and thought of her more as a neighbor than anything else.

She was not hard to look at, but her dress style did not showcase what I was later to discover was a very beautiful and well built young lady. She seemed to always have on jeans and some kind of pullover shirt that kept her well covered. I assumed her age to be around mid-twenties partly because of the age of her children and partly because of her appearance. That would make a 30 year difference in our ages and certainly contributed to how I viewed her and how I viewed our relationship. Hell, my oldest daughter was 29 at that time.

One night I had either been out or worked really late, I really can't remember which, but I was late in going to the mailbox. It was probably 10:00 to 10:30 and as I reached the community mail boxes, the same girl and another girl about the same age were sitting on the curb close by. By this time I had learned her name to be Jessica and she noticed me and initiated a conversation. This was the first time I had ever seen her dressed up with hair and make-up tastily done. Even then, her dress style was conservative and did not showcase her body.

She introduced the other girl and seemed quite proud to claim both the other girl and me as her friends. Jessica said they were waiting for another friend to pick them up and they were "going out."

I made note of the time and because I was almost 55 years old, I questioned their "going out" at what I considered "bed time" on a week night, but I didn't mention it to the girls. I excused myself and headed back to my apartment, feeling quite proud that I had been so completely and unconditionally accepted as a friend by such an attractive young lady.

The next few weeks were quite busy. I was working on putting together several interconnected business deals, including buying some resort property and setting up new entities with multiple owners to operate that property. I saw Jessica a few times and sometimes just made note that her red Sunfire was parked in front of her apartment. I guess I was noticing her more because of her introducing me as her friend that night.

We did meet on the sidewalk close to her apartment one time as I was returning from the office. We had a brief conversation where we agreed about the poor apartment management and I told her I thought I was going to move to another and nicer complex not far away. Other than that, I did not have the opportunity to seek out further interaction, mostly because of my preoccupation.

During the same time frame, I traded vehicles and upgraded from a 3 year old Ford F150 pickup to a new GMC Denali Yukon XL. That was the most awesome vehicle I have ever owned. It set upright like the trucks I had been driving for several years, could carry 7 passengers comfortably plus cargo space, had a sunroof and numerous other features like a killer sound system and it also performed more like a sports car than a full size SUV.

One night I came home to my apartment after a full and exciting day and night. It was about mid-night and I was pumped with a combination of adrenaline and alcohol and not nearly ready to go to sleep. I went into the apartment and changed into a tee shirt and a wrap around terrycloth bottom that left my crotch uncovered, although as long as I was standing, I was completely covered. Then I remembered I had not checked my mail, so I slipped on some sandals and took off to the mailbox, figuring I was safe at that time of night.

I had nothing except junk mail, and after throwing it into the trash can nearby, started back to my apartment. As I passed Jessica's apartment (the closest route from my apartment to the mailboxes took me about 10 feet from her door) I noticed a light on, so I decided to say hello. I am sure the adrenaline and alcohol contributed to that decision.

I knocked on her door and was soon greeted with a "who is it?"

As soon as she realized it was me, she opened the door and quickly started apologizing for having "no furniture" and saying if I wanted to stay for a few minutes we would need to set on the patio. She probably also felt more secure with us being on the open patio. Up until that time, we had only met and talked out in the open where we were easily seen. I was not there to judge her apartment or furniture, but I only noticed two bean bag chairs and a small television in the living room.

We went directly to the patio and set there talking about what had happened since we last talked. I told her of my business deals and she told me of her "new job" in a photography studio. Seems she was an assistant to a photographer who did posters and calendars with pretty young women as the models. Jessica would assist with the props as well as help the girl models with clothes, make-up and hair. I don't know anything about her experience or qualifications for such a position, but it didn't really matter to me at the time. She was excited about the job and that made me happy.

I told her there was a lake on the property I was trying to buy and it had a pier that might make a good background prop for that type of picture if they ever did any shooting "on location" as opposed to, "in the studio." She wanted to know more about it and I said I had drawings at my apartment as well as several pictures on my computer, if she wanted to see them.

She jumped at the opportunity, so we transferred to my place from hers.

As we approached my apartment, she asked where my truck was and I realized I had not told her about the Denali. She got so excited about the car, I thought she was going to wet her pants. She was jumping up and down, back and forth and asking questions faster than I could answer them. Because of the time of night, we were trying to be reasonably quiet.

I said, "Let me grab my keys and we can go for a ride." She waited for me at the front of the car, which was parked directly in front of my door. When I came back with the keys and a couple of beers, I unlocked the door with the remote and then pitched the keys to her and said, "You can drive."

She questioned that statement, I guess because she just couldn't believe she would get to drive a brand new $55 thousand vehicle. I assured her I was serious, so she took the keys toward the driver's door. We got in the duel front bucket seats, separated by the center console. She cranked the engine, but was then very methodical in adjusting the mirrors, seat and steering wheel, before putting the transmission in reverse. This certainly eased any apprehension I might have had about her driving my new SUV. She was very careful in backing out of the parking space and getting out of the parking lot, and I appreciated her caution. Can you imagine going from a Pontiac sunfire to a Denali XL?

I offered her one of the beers and she declined, saying she had pretty much stopped drinking after what happened on her birthday.

That piqued my curiosity; so I asked her what had happened on her birthday.

She started telling me the story, interrupted by conversation about driving the Denali. As we turned out on the street, she asked where I wanted to go.

I told her, she was driving, to go wherever she wanted to drive, but to continue with her story.

She said, "You remember that first day I met you and my ankle was sprained. Well the day before, was my 21st birthday and my friends took me out and got me drunk. I should not have been driving, but I thought I could make it alright. I ran off the road and hit something that made my tire to go flat. When I got out, I was so drunk I couldn't stand up and I stepped on a rock or something and turned my ankle." She went on to say that some guy stopped and changed her tire for her and she finally got home to the apartment. She had just gotten out of bed that next day when she saw me for the first time on a Saturday, mid-afternoon.

She was just so open and comfortable with me; with no mention of my age or our age difference. At that very moment, I am not sure what she considered our relationship to be. I am not even sure what I thought our relationship to be, but based on what I had learned during the last several years, I knew the mind of a 21 year old woman does not work exactly like that of a 55 year old man.

She was dressed in jeans and colored tee shirt with flip-flops. She did not have on a bra, but because I had not seen her in good light and had not touched her at all, it was difficult to tell at the time. She had an appearance about her that could only be described as a "natural beauty." Even without makeup and with her hair pulled back in a pony tail, she was beautiful. She did not need all the expensive things that enhance many women's beauty. She was about 5'4" with dark eyes and dark brown hair. Her skin tone reminded me of Mediterranean influence.

We continued to talk randomly as she drove and I made up my mind that I was going to try and seduce her, though I would not take advantage of her. In my mind, I was going to take it as far as she would let me, but at the first signal to stop, I would stop.