When I was sixteen, I 'had' my first boyfriend
At the age of sixteen, I must admit I was a horny teen. I didn't know much of anything about sex, but I sure loved flirting with the guys. As close as I'd ever come to sex was seeing my twelve-year-old brother's penis in the bath tub one night by accident.
I'd had several 'serious' but non-sexual relationships in junior high and up to my sophomore year in high school. I'd kissed a lot of boys, but never went any further. My first 'real' boyfriend was 15 year old James, or Jamie as he liked to be called. When I was 16 and got my license, my girlfriends and I would often go on dates with boys, meeting them as the movie house or going for a shake.
My first single date was with Jamie. We had dated for two to three months and spent hours kissing and stuff. He had felt me up, (which I loved. I would purposely leave my bra off and let him touch me over my clothes. He would later go under my top, which made me shiver with excitement). I never touched him. Looking back, Jamie would wiggle around a lot, which meant he was 'arranging' his erection, I would guess.
I remember the first time I felt his hard dick. We were playing around and kissing on my bed, and he fell on me. I could feel him growing through his sweat shorts. Jamie rubbed on me for about ten seconds and then let out the loudest groan I'd ever heard. He fell on top of me and said, 'I'm so sorry, but I came.' I really didn't know exactly what he meant, but he pretty much ran out of the room. He called me later that night and apologised again. I told Jamie not to worry, I enjoyed it too.
The next Saturday, I picked him up and we went to the hill near our high school, we called it 'Grind Hill', our makeout location. We immediately began kissing and one thing led to another this night. Jamie was feeling me up and I in turn made the bold move to feel him a little. I moved my hands up his tee shirt and then under it and caressed his nipples the way he did mine. All Jamie could do was groan. We then moved to the back seat and he moved on top of me and we grinded for a little. I could again tell he was hard, even through his jeans.
I was so hot and wet, and couldn't stand it. Jamie inched down to my jeans and rubbed my clit through my jeans. I did the same and lightly touched his crotch, not sure how hard to rub. Jamie then asked if he could take off his jeans. I said no, but then said ok, as long as his underwear was left on.
Jamie slid off his jeans and I could now see his hard-on tenting up his boxers. He laid back down and rubbed against me more. I then took off my jeans and we slid together against our underwear for a couple of minutes, I came fast, like I'd never done before. I had masturbated a few times, but found it not very exciting. I had the best orgasm I'd ever had, maybe it was my first, because it was so different than anything I'd been able to do with myself.
I then told Jamie he could continue rubbing until he came. He said he was 'raw' and needed to quit. We sat up in the back seat and I noticed he was still hard. I asked, 'Does it go down?' Jamie responded,'Yes, but it will take a while.' I then touched his dick through his boxers and said, 'If you show me what to do, I can help you finish.'
Jamie hesitated and then led my hand back to his penis. He took a hold of his penis through the slit in his boxers and there I saw my first real penis. It was pretty big, at that age I thought it was huge and told him he was so much bigger than my brother's. My brother had no hair around his, either. Jamie was probably only about five inches long, but it seemed big. He was also pretty thick. He began pumping up and down with his hand and then took my hand and led it to his dick and showed me how to pump. After a bit, he let go and allowed me to continue the jerking. I found his penis to be like velvet. He was uncut, which I didn't know the difference back then.
Jamie allowed me to continue while he laid back in the seat. I pumped for 15-20 seconds and he came. I then knew what cum was and what it looked like. It was so creamy and hot. I watched with fascination at how he jerked his body as he spilled out his semen. So this is what sex is and how it all works. His cum smelled musky and sweet. I got his cum on my hand, and it dried so sticky. I kept smelling my fingers to remember the scents.
We did it again a couple days later. We were alone in the car again and this time we got naked in the back seat. I was scared to get caught, but it was so exciting. I had never seen a real naked boy before except my brother, who was still a 'boy.' I was excited looking at his body, the male body has such beautiful angles, and the hairy penis and defined chest Jamie had, made me so hot. He did me, and then I jerked him, right into the floorboard. My car started to smell like dried cum, I know!
The next time we did it at my house, in the shower. I got naked first and turned off the bathroom light and then told Jamie to come in. It was so much fun exploring each other's bodies in the dark of the shower. Jamie had this way of circling my clit with his two fingers and I would instantly get wet and come quickly. I jerked him off twice in the shower. He then went back into my bedroom and I put a big towel around myself and followed him. I'd only seen his body in the dark with a faint street light, and this time I got to see him naked in the light. I was too embarassed to let him see me that way, but he seemed comfortable. Jamie looked 'hairier' in the light. He had lots of hair around his balls and they hung really low when he stood up. He was still pretty hard, and the way the penis angled sideways was interesting. Jamie didn't have any hair on his chest, except a little line going up from the crotch. He had a white ass, which looked funny. I'd already jerked him off twice, but he was still hard, so I did him again.
We had so much fun. Jamie would always cum about 10-15 seconds after I began to jerk. I thought all guys came quickly. It wasn't until later I found guys could hold off a long time.
One time, late into our relationship (probably 4 months later), we double-dated with two friends, I'll call 'Jack and Jill.' They were in the back seat and we were in the front. Things got so hot and heavy at 'Grind Hill' and Jamie and I were rubbing each other through our clothes. I then noticed in the rear view mirror that our friends were already exposed. Jack had his hand into Jill's shirt and Jill was rubbing his exposed penis. This was the second real penis I saw. I looked back and said, 'What are you doing.' They laughed and said, 'Come on, don't you want to?' So Jamie and I also did it. I was embarrassed but knew they couldn't see above our front seats in their positions. I watched them for a little while and found it interesting. Jack had a great body, when he took off his shirt and had his underwear around his knees, I saw his body pretty well. Jack's dick was long and skinny and he had very little pubic hair. He also came fast.
I wouldn't let Jamie take my clothes off, but I did jerk him off, while they were in the back seat, cleaning up. That was an interesting experience. Jamie's dick was much thicker, but not nearly as long. Jack had a cut penis. At the time I didn't know what made it different, but I knew it looked different. To me the circumcised penis looks somewhat wrong, I can't explain it. Jack had really dark features and was gorgeous. I think that led me to break up with Jamie. He was my first, but I wanted to explore more with other guys. It was a fun 16th year!!
Later that year, my 12 year old brother must have started going through puberty, because I noticed his bedroom smelled like my back seat, like cum! I cornered him one night and kidded with him and asked if he was spurting yet. His answer was, 'How do you know what comes out of a peter?' I shut up. As he grew into his teen years, my brother became very free with masturbation. It was actually refreshing. I saw him several times masturbating. He would never do it in front of my parents, but if we were alone at home, he would whip it out while we were watching TV, or in his room with the door open. We never really discussed it, I just accepted it. Nothing sexual. My brother had and has a great body and he was always free (much more than I was or am) with nudity. Puberty was his rite of passage and he jerked off freely. He still has one of the most beautiful (if a penis can be beautiful) cocks I've ever seen. I am not trying to be perverted that I want to have sex with my brother, because I don't. But, he is large, and has just the right amount of pubic hair and large balls. He is about seven inches erect. I always admired his crotch. Anyway, that's my story for now.