The story of how a shy fourteen year old boy loses his virginity.
Growing up in a small city in northeastern New Jersey may not sound idyllic to you, but to me it was like heaven on earth. In the summer of 1964, life was simpler, especially for a fourteen year old boy. My name is Jack. My days were filled with sports. We would play baseball all morning, go home for lunch, then, come back and continue into the early afternoon until it got too hot. Afterward, we would sit at one of the picnic tables under an old shade tree relaxing, talking sports, maybe goofing on some of the little kids that dared to pass by; then go home for supper. After supper, it was back to the park for an evening of basketball; then back home when it got dark. Tough life, right?
Life, for me, changed forever one warm evening in July of that year. The day had started out like most other sunny days; we had played baseball all morning, but when the game broke up at lunch time no one wanted to continue later. It was just too dam hot and humid. For me it was a perfect day to stay at home, in the breeze generated by our big window air conditioner and relax. I listened to some music on my transistor radio, just killing time until dinner. After dinner, I walked back over to the park, sat on the merry-go-round, which served as courtside seating in the evening and waited for the guys to show up.
One by one the regulars started to arrive. Tonight, however, it seemed we would be shorthanded. I guess it was because of the heat, we only had six players. We broke up into two teams, skins and shirts; and played a little three on three half court, hoping for others to arrive. None of the other players showed up; but a group of spectators did.
Amy and two other girls took seats on the merry-go-round. Amy was a big girl, tall, with big tits, a big ass, and an even bigger mouth. I didn't like her very much. She just seemed to take over whenever she was around; and for a shy guy like me, she was just too much to handle. Not that I didn't like staring at her tits. What fourteen year old virgin boy wouldn't? I didn't recognize the two other girls. They appeared to be sisters, maybe even twins. They were the exact opposite of Amy; short, thin, small chested and best of all, quiet.
After our game ended, I grabbed my shirt and with the others, walked over to the girls and stood around talking. Amy introduced the girls as her cousins, Gloria and Debbie, from Brooklyn. They had been staying with Amy while their parents searched the area for a house to buy, wishing to escape the "Big City" for life in the country as they put it. I was fascinated by the sisters; they were not twins, Gloria at fifteen being a year older than Debbie. To me, they were from a far away land, full of mystery and intrigue. Actually, New York City was only about ten miles away, on a clear night you could see the skyline from the Empire State Building to the lights of the George Washington Bridge. But that seemed so far away when you didn't drive and you had never left the state before.
I don't know who suggested it, but we all agreed that it was too hot to play any more basketball that night, instead we all got up and headed out of the park, our destination School No. 2. The school was about a quarter of a mile away. It was a large, sandstone two story building that had been built in the thirties, when the city was still mostly farm land. It had been built to last forever. As the small farms in the area were bought up by developers and were replaced by over fifteen hundred houses, wings were added to the school. We were headed to the side of one of those wings; more specifically, to the stairs leading up to the side entrance. They were wide, roomy and completely hidden from the street and the neighboring parking lot and houses. We weren't going there to get into trouble, we were just going there for the privacy, a space that seemed to be your own just to hang out, relax and talk.
When we got there, Amy parked herself on the middle of the center stair. Like a moth draw to a flame, my four friends all gathered around her two on each side, one stair above and one stair below. I being the only other guy; on the walk over we had lost one as we passed his house, parked myself down on the ground, against the side wall which shielded us from the street, Debbie on my left and Gloria on my right. They talked about life growing up in Brooklyn. How the schoolyard was their focal point in life and the streets their playground. I felt comfortable with them, talking and listening to their stories.
We were basically having our own conversation, the other group all but forgotten. Suddenly I heard Amy start laughing and giggling. That got our attention. I don't know how it started, but all four guys were trying to kiss her and grab a feel of her big tits. Having never even kissed a girl before, I was a little bit shocked and envious of their behavior.
"Hey. Hey. There are two other girls over there," Amy's bellowed out in her usual loud voice. No one moved away from Amy. I guess they were all after her big tits.
"Come on, Jack, Let's get out of here, Gloria whispered in my ear. Do you know any place around here that's a little more private?"
Having attended this school for seven years; K-6, I knew exactly the place to go. When the school was first built, the kindergarten was off to the side of the building. Now, after the addition was completed, it was tucked away, almost lost between the old and new sections. The best part was that the kindergarten had its own private play area, which was shielded on three sides by the school building and across the back by a massive eight foot high stone wall. The entrance to the play area was a small wrought iron gate, on one side of the wall. But because of its placement nearly the entire playground was shielded from view.
So with a girl on each arm I headed around to the back of the building. Just before we turned the corner, Gloria called out to Amy,
"Have fun Amy, we'll be back in about an hour."
On the way, Gloria looked up at me and asked,
"Jack, have you ever kissed a girl before?"
Looking across my body at Debbie she said,
"Oh, this is going to be more fun than I thought."
I was so naïve that I thought she meant that we would be kissing a little. I had no idea what was about to happen to me. Even so, the thought of kissing not one but two girls, was both exciting and intimidating. I could feel my cock already getting hard, it was a good thing I was wearing briefs and that my cut-offs were a little loose or I would have died of embarrassment. I lead them to the gate, reached in and opened the latch, and we stepped inside.
'This is perfect." Gloria said. Taking my hand, she led us to a narrow bench located on one side of the yard. It was backless, smooth and was sealed with a fresh coat of varnish. We sat the same way we had done before, with me in the middle. Then, Gloria reached up and holding the side of my face kissed me right on the mouth. I felt the world stop moving as she opened her mouth and I felt her tongue licking my still pursed lips. I got the message and opened my mouth, her tongue invading and doing battle with mine. She took it one step farther when she started exchanging breaths with me. Now, I was completely hard and a little uncomfortable; but I wasn't going to complain. After a minute or two, she broke the kiss and I felt Debbie's hand on my other cheek gently turn my head towards face her. This time I was a little more prepared. As our lips touched, our mouths opened, and my tongue was the aggressor.
We went back and forth several times. I was in heaven. Then, as I was kissing Debbie, I sensed that Gloria was standing up. Debbie and I continued to make out; I could feel Gloria was back sitting next to me. After Debbie broke the kiss, I turned expecting to continue with Gloria. I froze. There sat Gloria, naked from the waist up, her small, rounded tits, with their hard nipples, were staring me right in the face.
"You like" she whispered. Of course I liked. These were the first tits I had ever seen, other than the time we stole my friend's older brother's Playboy magazine. These weren't as big, but they were perfectly shaped and they were right there. She took my hands in hers and placed them on het tits.
"Go ahead feel them, play with my nipples, I love that."
.... There is more of this story ...