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Early in high school I was an avid masturbator. I wish I knew just how many times I jacked off. In bed at night was probably the most common time/place but anything related to sex would trigger the urge, so I did it many other places as well including the restrooms at school.

I guess it was junior year of high school that I overcame shyness and started having more contact with girls. There were a couple that were one-time dates going to a movie, often with a quick kiss after but nothing significant.

Some time in late fall we had a class field trip that required a couple of hour long bus ride. On the way home in the late afternoon I sat next Lynn, a friend in the class, way in the back of the bus. We talked about the class and what we had seen that day, but then after awhile it had gotten dark and she leaned over and kissed me - a real kiss, not just a peck on the lips. Her lips were so soft and sensual that it immediately excited me. We separated and she smiled, we moved a little closer and then proceeded into a real makeout session. I think like any teenage boy my cock was stiff as a bone the whole time. After a bit I reached across and slowly slid my hand from her waist upward. Surprisingly to me she did not stop it. Eventually I reached her breast, and gently fondled it. She was fairly small and was wearing a bra with very soft, silky material. I was amazed how soft her breast felt, and slowly moving my fingers I found the nipple which stood out a little. Our mouths were busy, tongues engaged by that point. I was in heaven, hardly noticing my cock throbbing in my pants. After some time I decided to go for it and moved my hand downward, hoping to slide it up between her legs under her pants. She quickly sensed what was going on and grabbed my arm to stop it. I went back to fondling her breasts, as we continued to kiss. Must have gone on a half an hour before we arrived home.

As we exited the bus Lynn gave me a quick hug and with a smile said she had had fun. My boner had gone down but I noticed a distinct wet spot in my pants where precum had leaked, and I also realized that there was quite an ache down below. I had heard the term ‘blueballs’ but did not really know what it meant until then. As soon as I got home I headed for the bathroom and rubbed out a good load, which helped but did not fully relieve the ache. Lynn and I went out on dates several more times, with long makeout sessions after, each time recreating the ache. But she never did let me get my hand between her legs, and never touched me down there either. For several reasons we weren’t really compatible and parted ways, but I remember those takeout sessions.

The next girl I went out with was Jane.  She had fairly long, somewhat curly hair, had glasses, and often wore skirts or jeans.  We met at a meeting of an outdoor club (hiking, camping, etc.), and hit it off quickly. After the second meeting we attended I asked her out to a movie. We had a good time, capping it with a long kiss when I dropped her at home. We saw each other in class a couple of times, and the next weekend we went out again and had another good time.

When I drove her home I parked a little way down the block from her home, and we started making out in the car. She let me feel her breasts through her shirt, which were small but different from Lynn’s. The nipples seemed to stick out further and were quite stiff.  Of course I was hard the whole time. By the time I got home I had that familiar ache and relieved it as best I could, thinking about Jane’s breasts as I did.

The next date she let me feel between her legs as well, but she had worn pantyhose and blocked my hand when I tried to move inside them. Still, it was a big deal with feeling her pussy even that way. We made out that way for quite awhile, and after I took her home I really had sore balls. 

The next ‘advance’ for me was a couple weeks later when the group went on a camping trip.  Of course men and women were segregated into different tents.  In the evening (well after dark) we wandered out of our campsite and sat on a bench in a neighboring one.  We sat side by side for a bit and were making out. Jane stood up and straddled me, and we went back to kissing. I slid my hands up under her sweater (which was large and bulky) and it hit me that there was no bra strap. I slowly moved my hands up to her bare breasts and fondled them, softly pinching the large protruding nipples. Janes hips were subtly moving back and forth in my lap as I did this, pressing gently against my erection. After a few minutes I lifted her sweater so I could see her breasts, though it was pretty dark where we were. As I had thought from the feel, her breasts were quite small but the nipples stood way out and were very hard. We broke the kiss and I leaned over to suck on the nipples, taking each in my mouth alternately.  She moaned softly and humped against me. 

This went on for some time but it was really quite cold, and we were both shaking a bit from the combination of arousal and cold. Jane finally pulled away a bit and said we should go back to the main campsite. I was a little disappointed, but also very cold, and we wandered back hand in hand. Not long after, we said goodnight and headed into our respective tents.  I was sharing with another guy, but he was not back yet. I quickly undressed and slipped into my sleeping bag.  I was still fully erect, still excited from our encounter.  I imagined Jane in her tent also being excited and that she would be masturbating.  My hand slid down to my cock and I think it wasn’t more than 10 strokes before I had to grab my t-shirt and pumped squirt after squirt of semen into it. 

I do wonder if Jane had gotten herself off too. We went out a couple more times but I knew she had also gone out with another guy, and she decided she liked him more, so that was the end of things between us. I will never forget that first encounter with bare nipples though.