It was in the early sixties and I had just turned sixteen and I was still a virgin. I had had a couple of girlfriends and we had played around some but I still had not found a girl that would let me put my cock in her. This was before the internet and even before VHS tapes so all the naked women I had seen were in Playboy magazine. What I knew about sex was mostly from what other guys talked about but I knew that I wanted to know more, much more and soon. The only action my cock got was from my hand. It got plenty of that.
I hung out mostly with my best friend, Herb. He was a year older than me and had just gotten his drivers license and sometimes had access to his dad's car. He told me that he had gone all the way with his cousin and one other girl. I believed him. One day he told that he had heard about a woman that on Friday nights stayed in her car behind this local bar and for five dollars gave blowjobs to anyone that wanted one.
One Friday we took his dad's car and drove to that bar. Drinking age was eighteen then but neither of us was old enough to go into the bar. We parked in the back lot and watched. We spotted a woman in a car but it was too dark to get a good look. Soon, a man came out and got in the passengers side. She bent over and was out of sight for several minutes. Then her head came back up and he got out and went back into the bar. We watched for almost an hour and saw this happen two more times. Neither one of us got up the nerve to go to her car.
During the week we talked about that night and dared each other to do it the next time. Every day that week, I jerked off at least twice. Finally Friday came again and again we were able to get the car. I worked part time in a record store after school and on Saturdays and earned one dollar an hour so five was a lot of money for me. I put five dollars in my pocket and Herb picked me up. We both had to be home before eleven.
We parked in the parking lot not far from the car we had watched the last Friday. It was empty but shortly we saw the woman come out of the bar and a man was with her. They got in the car and soon he was all you could see for several minutes. When she was alone in the car again, Herb and I prompted each other to go do it. Finally I got up the nerve and got out of the car and went to hers. I stood next to her passenger’s side door and looked in. She looked to be almost my mother's age, skinny and not very pretty. I almost chickened out when she said, "Hi. Hope in."
I got up my nerve and opened the door and got in. I held my five dollars out to her. Smiling, she said, "You've never been here before but I see that you know why I'm here." She took my five and opened her blouse, exposing her somewhat sagging C-cup tits. She took my hand and pulled it to her chest while she reached for my pants. After she had unbuckled my belt and unzipped my fly, she told me to pull my pants down. I pulled then down to my mid thighs. I admit that I was nervous. My cock was as hard as it had ever been.
She reached out and wrapped her hand around my five and a half inches. I almost shot right then. She stroked it a couple times and then bent over and put her mouth around the head and sucked while tickling my piss hole with the end of her tongue. Then she slid her mouth down my shaft, taking almost all of me into her mouth. God that felt wonderful. It was so much better that when I masturbated. She started a rhythm, bobbing up and down rapidly on my no longer virgin cock. She kept her lips tight enough so that she moved the loose outer skin up and down on the rock hard inner shaft and her tongue rubbed over the underside of my prick.
I didn't take her more than about a minute to bring me off. She had my balls in her hand gently squeezing them and when she felt the sack tighten, she stopped with my cock head just inside her mouth. She jacked me just a couple last times causing me to blast my cum load into her mouth. I sprayed three times. She caught every drop and showed it to me before swallowing it. Seeing that my young prick was still hard, she slurped on it a few more times before sitting up. She pulled my hand away from her chest and said, "That was nice, Honey. I hope your liked it and will come back to see me again."
I got out of the car and on shaky legs and, still zipping my pants back up; I went back to Herb's car. As I got in Herb said, "How was it? Did she really give you a blowjob?" I replied, "She sure did and she let me play with her tits while she was doing it. She sucked it till I shot in her mouth and then she swallowed it. That was amazing. I've never felt anything that wonderful in my life." The driver’s side door flew and Herb literally ran to her car waiving his five dollars in the air. He quickly got in her passengers side. It was almost five minutes before he came back to the car with a big smile on his face. It was ten thirty and we had to get home. On the way, we talked and talked about what had just happened.
Over the next month we went back twice more and repeated the event over again. Then I met Dianna and she was more than happy to spread her legs for me any time I wanted. I almost forgot about the blowjobs from this older woman and my friend Herb too, till a couple months went by and Dianna went on a trip with her parents. While she was gone Herb took me back to the bar. He had continued getting blowjobs from this woman that he now called Joan. As her mouth was sliding up and down on my cock, I remembered the pleasure she had given my then virgin prick. I knew that I had to find a way to get Dianna to use her mouth on me sometimes. And I sure hoped that she would enjoy doing it.