It was 5 years ago, a couple of weeks after Jon and I graduated from High School. We were both 18 and had been dating most of our senior year. I liked him a lot and we were really good friends. His parents were away that Friday night so we had rented a movie and went to his house. We watched the movie ‘Basic Instinct’ which contains a long sex scene. We were snuggled up on the sofa and I could tell Jon was getting very excited as we watched Michael Douglas and Sharon Stone get it on. I was getting excited too. We hugged and kissed a lot as I let him fondle my breasts. I had never let him or anyone else touch my pussy. I had never felt that I was ready for all that.
When the movie was over, he asked me if I was ready to have sex. I said I expected to have sex someday but that I was very afraid. I said had heard that the first time was extremely painful and besides I was not on any kind of birth control. He explained that the pain was the result of stretching and tearing the tissue and if we did it very slowly and gently it would not hurt at all. He offered to tell me what to do and to show me how to do it. He said that I would be totally in control, we would stop any time I wanted to, and that he had plenty of condoms.
While I was thinking about it he helped me up from the sofa, led me to his bedroom, and put on some music. Somehow, that night it just felt right. He said the first step was to get naked and asked if he could undress me. I nodded yes and a minute later I was naked. Now it was my turn to undress him. I removed his shirt and pants and stared at the bulge in his shorts. I had seen my brother naked but had never seen an erection. When I removed his shorts, there it stood about 6 inches long, over an inch thick and with a smooth red head at the end. He let me stare at it for a few seconds and then he gathered me into his arms and gave me a long deep kiss as it pressed against my thighs. My knees started to get weak as it found its way to my crotch. My emotions were really racing.
He released me and said that that was for later. He said that there were several steps we needed to do. First, I should wet one finger with saliva and then gently slide it into my pussy. I did and it slid right into my very moist virgina. Jon nodded his approval and suggested I wet a second finger and very gently slide in two fingers. That took a little longer and my telling myself that “you can do this” but soon I had two fingers all the way in. Jon said I was doing great and gave me a long passionate kiss. The last step was to wet a third finger and slide in all three. I was only able to get three fingers in up to the knuckle. Jon said to stop there and that I was now just about the right size.
While I rested for a couple of minutes, Jon got a big towel and put it on his bed. Then he opened a condom package and I watched as he rolled the condom onto his erect penis. He asked me if I wanted the lights on and if I wanted to be in control. I decided that since I could only lose my virginity once, to say yes to both. He put KY jelly all over his penis and stretched out on the towel. He asked me to get on my knees and to straddle him. He rolled my pussy lips open as I positioned myself over him. He held very still as I slowly lowered my pussy onto his upright penis. The head was almost in when we encountered resistance and pain. He suggested that I stop, wait a minute or two and relax. Again I told myself “you can do this” and it worked. As I relaxed what was left of my hymen stretched and I was able to slowly lower myself onto his erect member a quarter inch at a time. After a couple of minutes he was completely in. My pelvic bone was resting on his pelvic bone as our pubic hairs intermingled. He told me I was doing great and to rest in that position as long as I needed to. Any initial pain disappeared and my pussy now felt very, very full. I leaned down and gave him a long gentle kiss before I started to slowly move up and down on him. He held very still as I slowly went from half inch, to one inch, to three inch strokes. He began to rub my breasts and massage my nipples. The cumulative effect was electric. Next, he began to thrust his loins against mine. We found a natural rhythm and the combined effect was overwhelming. In almost no time, I had my first orgasm. A minute or so later his penis swelled even bigger and jerked several times as he held it all the way inside of me. I collapsed into his arms, a very happy ex-virgin.
As we rested, his penis deflated and slowly slid out of me. I was amazed at how much fluid there was in the end of the condom. It looked like a quarter of a cup. I then made the mistake of looking at the clock and realized that it was time for me to get home. We quickly cleaned up, got dressed and Jon took me home.