This series of stories are mostly true, based on the journals I've kept through the years and my memory. Most of the names have been changed to protect the innocent, or not so innocent. No one (except maybe my wife) would ever describe me as good looking, much less handsome. I'm short, about 5'6", medium build, with a somewhat large nose and projecting ears. As a teenager, I was downright skinny. What I do have working for me is a sense of humor and a gift of gab. Somehow, I've had a good deal of success bedding some very beautiful women, most of whom were married, engaged, or otherwise committed. I'm a professional that has enjoyed a modicum of success in my professional and personal life. I've also been very fortunate to find, not only one, but 2 loves of my life. A few years after my first wife of over 30 years died of complications from surgery, I met my current wife a few years later and have enjoyed married life again.
During my senior year in high school, I developed the habit of ending each day by writing in my journal which I do to this day. After my heart attack at age 50, I transferred my journals to computer files so I could better maintain the confidentiality in them. The sexual encounters portrayed in my stories are based on my notes and recollections. I hope you enjoy them!
This first story is about my first time. Started with doing a favor for a cute, "almost" engaged coworker resulting in me seducing her and engaging in a 5-month fuck fest. I'll forever be grateful for our time together where I sharpened my sexual skills under her tutelage.
It was the late 60's, the height of free love and sexual adventure. Well, at least for some, not for me! I was an 18-year-old virgin, finishing my first year of college, without ever having a "real" date. Yes, I attended proms, dances, and even a movie or two with a girl, but it was always a girl that was a friend of a friend or a school chum of one of my sisters. If it wasn't for them, I wouldn't have has any dates. My social development was hindered by 2 events in my life. My parents moved about the same time I finished grade school (8
th
grade), leaving my childhood friends (meaning girls) behind, and I attended a private boy's high school. We now lived in a very rural area without any close by girls my age. My school commute was cumbersome, at least two buses, and I was heavily engaged in school activities so didn't socialize much at our new home. My first year of college wasn't much better. My choice of major (engineering) meant that I had virtually zero chance of meeting any girls in classes. I attended a local major university, so I lived at home. I worked part time at a hardware store after school and during the summer between high school and college, so I really didn't have much of a chance to meet girls.
As soon as college classes ended in late April, I quit the hardware store and got a job working at a restaurant as a short order cook. I bought my first car for $75. An old ford that was well cared for without a whole lot of miles. I needed more hours than the 12-20 or so a week I was getting at the hardware store. The restaurant was a local chain with a medium size dining room and car hops. A few of the waitresses and car hops were girls about my age but either had steady boyfriends or were not at all interested in my feeble attempts to charm them into a date.
A couple of weeks after I started working, Karen was hired. Karen was cute, about 5'2" with short strawberry blonde hair, maybe 130#. Although she was a bit chunky, she was shapely and very cute. She did have a little extra, but it was all in the right places with a perfect heart shaped ass and full, 34C, breasts. Unfortunately, Karen had a steady boyfriend. In fact, she described the relationship as "engaged" without a ring - yet. Her boyfriend was a high school dropout that was working construction off and on. He was tall, maybe 6'5", and skinny - leading to his nickname, "Stretch." According to Karen, they planned to marry in a year or so as soon as he secured a steady job.
Karen and I hit it off almost immediately. Maybe the fact that I knew she was totally off-limits made it easier for me to talk to her. During slow times Karen would hang around my grill station. We'd talk about everything; school, parents, the newest records, well - you get the idea. I guess this was the first time since I was in grade school that I had a friend, even casual, that was a girl. Karen was a high school senior, graduating in a few weeks. She had no plans beyond high school other than to work some, get married and have kids. She was an only child, living at home with her parents. She turned 18 in March.
One day in early May, Karen walked with me into the back of the restaurant in a very somber mood. It was obvious that she had been crying. I didn't pry - thought she'd tell me what was wrong if she really wanted me to know. One of the "older" car hops, Debbie, asked her what was wrong.
Karen said, "Stretch's brother-in-law got him a great job on a framing crew for a builder on a major housing development. The only problem is it's in a neighboring state, about 250 miles away. His long work weeks (6 days minimum) and long hours meant that we won't see much of each other over the summer."
I noticed that all the time Karen was talking to Debbie, her mom had sat out in the car outside the door with the engine running. It seemed Karen had a more serious problem and needed to talk to the manager.
She said, "Don, you heard what I said about Stretch. I have a problem getting to and from work. My dad works swing shift, Monday through Friday, from 3:00 - 11:30 and mom works from had a 4:00 pm to midnight. I don't drive yet, so I'm at the mercy of my parents' availability to drop me off and pick me up. With my boyfriend gone I don't have a ride between about 3:30 p.m. and midnight on weekdays. In fact, I'm supposed to work the afternoon shift today, from 11:00 - 7:00 and don't have a ride home. If you can't change my shift, I'll have to quit."
The manager wasn't happy. Although it was a Monday, the weather was nice for the first time in several days and he expected improved business. He was already short of car hops, losing one more would really hurt.
Don asked me, "what time do you get off. I think you live in the same area as Karen, right?"
Although I didn't know it at the time, I drove right past the road Karen lived on during my commute. I responded, "I think so, I'm just starting my shift, working the lunch/dinner shift, 11:00 - 7:30."
"Can you give Karen a ride after work?" He asked.
I looked at Karen and said, "is that OK with you?"
Karen smiling responded, "great, I'll pay you for gas if you can give me a ride when we work the same shift."
After my shift ended, I went to the locker room, took a hot shower, and changed into my "street" clothes. I went out to my car and hung out waiting for Karen. She came out about 10 minutes later, carrying a brown paper bag. She too had changed from her uniform into a short, shirt-style dress.
After we left the parking lot, Karen asked, "are you in a hurry to get home?"
