Just love the site. It brings back so many sweet memories.
I was a late developer and did not experience my first ejaculation until I was 14. I was big into sports and football and that provided me with all my fun until then. My first masturbation experience involved me lying on my belly in bed and gently rubbing my erection against the bed sheets. The first time I came was explosive and my pyjamas and the bed sheets were soaked in hot sperm.
But my first experience with a girl did not occur until much later, when I was seventeen. A new family came to live in our street just opposite from our house. There was an older boy and a girl aged 15. She was physically very mature with large 36 CC breasts and a great womanly figure. We first met a couple of days after she moved in when she came out to watch me play football by myself in the street. When I saw her I smiled, went right over and introduced myself. She told me her name was Kathleen and I asked her did she want to play football. She laughed and said she was less than useless at football but could play Curby. This is a game that involves throwing the ball from one side of the street to the other to see if you could hit the curbstones that caused the ball to bounce back and gave you a score and a free throw.
We played a number of games and Kathleen was really quite good. We soon had a sweat on and I could see that her breasts swung pendulously each time she threw the ball. I soon had a hard on focusing on her ample cleavage, which did not help my game. We finished up with Kathleen winning more games. We then sat on the wall outside my house and just talked. She explained that she was the youngest in her family and that dad was a widower who could no longer work because of a lung disease. I really felt comfortable talking with her even though she was a couple of years younger than I was. That night I masturbated vigorously while imaging Kathleen's breasts swinging freely.
Our friendship grew over the next few weeks although at times Kathleen could be quite shy and embarrassed around me. One particular day a schoolmate was staying over night with her so there were three of us playing in the street. She was very slim and pretty with long blond hair down over her shoulders. But she wasn't my type. Later she teased Kathleen in front of me by saying that Kathleen was still a virgin. Kathleen went bright crimson and immediately I rushed to her defense and said so what, so was I. Her friend stopped teasing and I could see Kathleen smile with her head down.
The next night I was taking the family dog for a late-night walk and I asked Kathleen did she want to join me? She said yes rushing back inside only to gather her coat. When we walked I mainly did the talking. Naturally, I led the conversation. I asked her if she had ever been with a boy. She mumbled yes, sort of, but not a steady boyfriend. I asked her to explain. She said she had played games in her friend's house one night at a party when she was drunk and that a boy had got fresh with her but she wouldn't let him go all the way. Again she went bright red just talking about it. I told her I had never been in a steady relationship either and that apart from masturbation was sexually inexperienced. I said this matter-of-factly without looking at her but I was aware she was staring right at me. I continued walking with Kathleen catching me up. She then put her hand in mine. I looked at her smiled and accepted.
Just then I decided to take a short cut through the woods. It was quite dark but for a half moon overhead and Kathleen pressed close against me. I could just feel the warmth of her breast brushing occasionally against my arm. Not far into the wood I stopped by a tree. Kathleen turned to see why I had stopped and I just reached out and pulled her against me and gave her a long, wet kiss. Then her tongue quickly shot into my mouth and the feeling from my first French kiss sent a real shock through my body. My cock was real hard. I undid the buttons of her coat, unzipped my parka and pulled her warm body against mine. I could feel her nipples almost rigid through the fabric of her clothes. We kissed passionately some more. Then I pressed my right hand against her shoulder and slowly traced the outline of her body ending on her thigh, which I gave a gentle squeeze. She gave a little moan and raised her left thigh against my waist pulling me closer still with the back of her calf. I placed my hand on her left breast, squeezed and kneaded it and I definitely could feel her nipple stiffen. I pulled the top buttons of her blouse free and cupped her breast then slid my fingers inside to feel her bullet-hard nipple properly. She moaned even louder. I pulled her bra cup aside exposing a very erect nipple that I immediately sucked hard on. Kathleen was moaning loudly by this time and I dropped my hand to feel her inner thigh before pressing my fingers gently against her cunt. She squealed with delight, and responded by thrusting herself vigorously against the palm of my hand. She was hot and as I squeezed the hand down below the waistband of her knickers against the wet lips of her vagina she suddenly gasped, moaned and fainted. She had just experienced her first orgasm and blacked out momentarily. A few moments later she came to resting on the grass. She looked dazed but pretty pleased with herself. I pulled her to her feet and kissed her on the forehead and said, come on -- let's get you home before they send out a search party for us.
We walked home hand in hand not exchanging a word. Just occasionally she squeezed my hand and smiled a little. Outside our homes she gave me a gentle kiss, said thanks, that was wonderful and headed inside. I was happy but still horny at the same time. I made my excuses and went to bed early that night. As I undressed for bed I closed my eyes and relived the experience of that night. I was soon pulling vigorously on my cock. My room is at the front of the house looking across to Kathleen's house. Just then I saw Kathleen's face at the window of her landing. I opened the curtains slightly and masturbated in front of her until I came. Then she disappeared into the bathroom a second. Moments later, she re-emerged onto the landing and put the light on. I could see she was naked. She smiled, blew me a kiss, turned and walked away.