Chapter 2
Jack
I got a job the summer before my senior in high school at the local grocery as a warehouse man and stocker. I spent two hours at the gym lifting weights and using the treadmill every morning.
About mid-July, I noticed that there was a cute redhead that was showing up every day at the store. Each time she was there, she would seek me out and ask for my help finding things on the store shelves.
After two weeks of that, I asked her out on a date and she shrieked in happiness as she accepted my offer. I found that her name was Janis when we exchanged phone numbers. I felt quite flattered that this cute redhead seemed to have a crush on me.
Since I already had my driver’s license, Mom let me borrow her car to go on my date with Janis. Janis looked sexy as hell in her skin tight low rider jeans and pink cashmere sweater top. With her 4 inch platform sandals, she came up to 5 foot 8. Still 6-inches shorter than me.
I took her bowling for our first date. Now she was 10-inches shorter than me in the flat bowling shoes. We had an absolute ball bowling together. Afterward, I took her to a nearby diner for burgers and milkshakes.
While I was driving home, I found out that Janis was a year older than me. She told me she had a medical problem of some sort in 10th grade and ended having to take 10th grade over when she was better.
Our second date ended up being dinner at my parents’ house and a celebration of my 18th birthday on Friday evening. When I took Janis down to the basement to play video game after the birthday party with cake and ice cream, she pulled my jeans down and sucked me off on the downstairs couch.
I was scared to death the entire time that one of my parents might come down and catch us. But in the end, I had the most monumental climax I had ever had in my entire life. Of course, up till now the only sex I had was masturbation.
Janis kissed me more passionately than anyone else ever had when I took her home around 11pm. “You owe me a good pussy job,” she told me after the kiss. “I’ll pick you up tomorrow evening and take you somewhere special,” she told me.
Because I had been growing my first goatee over the past three months, I trimmed around it so it was nicely sculpted. Just enough of my dark brown stubble to make it so you could tell it was a goatee.
I wore a loose pair of slacks and a tight Henley shirt for our date. Janis was wearing a miniskirt and tight halter top. As always, she looked quite sexy. After a kiss on the cheek, she informed me that we were going to a drive-in movie.
The drive-in had closed many years ago. But recently a young enterprising fella and his best buddy bought the property. They cleaned up the property and then purchased dozens and dozens of old black and white movies and a boat load of old b-movie thrillers.
The drive-in is only open on Friday and Saturday nights. They charge twenty dollars per vehicle. The drive-in has become a huge success with the young high school and college groups.
Although Janis took us to the very back of the drive-in just after dark, it was pretty obvious that most of the people here in the drive-in were not necessarily here to watch whatever show was put up on the screen.
There were cars all over that were rocking back and forth like there was some sex going on in those cars.
As soon as we climbed into the back seat of the vehicle, Janis pulled out my cock and started sucking it to erection. On her knees, I saw she had no panties on under her miniskirt. My cock was as hard as concrete when she straddled my lap and mounted my cock.
“Don’t we…need a condom?” I groaned as her searing hot vagina swallowed up my entire cock. “Oh no baby, I am safe,” she told me. I took that to mean that she was on birth control.
I pulled the bottom of her halter top up and went to town sucking and slurping on her orange size 32D breasts. I am ecstatic that I am finally inside a girls pussy for the first time. I think I am going to love not being a minor anymore.
It doesn’t take long for my cock to explode into climax inside Janis’ pussy. The sensation of ejaculating inside of a pussy was the most pleasurable thing I had ever experienced.
We watched the black and white movie on the screen for about 20 minutes. When my cock began to swell back to life, I pressed Janis onto her back and buried my face in her pussy.
I did not care that my cum was oozing into my mouth from her pussy. I was on a mission to make Janis feel as good as she made me feel the last two evenings.
When her body began jerking in orgasm, I lunged forward and fucked her with abandon until I blew a second huge load of jizz deep into her womb.
Imagine my surprise when she dropped me like a hot rock right after fucking me that night. When I called her house, her mother told me that Janis had just gotten a good job as a waitress at a high class restaurant and did not have time to see me anymore.
After talking to her mother, I asked myself why I was having such a hard time with girls. All three of the girls I have dated ended up hurting my heart.
I always believed the girls would be attracted to nice guys. It has been my experience so far that nice guys get fucked over.