I find your site informative and entertaining.
I've watched for stories that parallel an experience of mine, but so far haven't seen any, so I'll tell my story.
I 'came of age' in the mid sixties, just before the 'sexual revolution' came to the hinterlands where I lived; before birth control pills were widely available, and before 'free love' was being widely promoted. Those were the days when there were 'good girls' and 'bad girls', and in spite of that it was a prime objective every teenage boy had to lose his virginity at the first opportunity, and if successful, to repeat the experience at every opportunity.
Through locker room talk and experimentation I'd discovered masturbation relatively early, and in my late teens I seemed to always feel horny, but I was shy by nature, and my courting techniques were sorely lacking. I had great desire to 'go all the way' with girls, but was somewhat clueless as to how to best get there.
I'd gone out with a number of girls, and found quite a wide range of interest and enthusiasm for sexual experimentation among them. I'm sure there was a strong relation in all this as to how attractive the girls found me, but even when I was quite sure that the mutual attraction seemed to be at about the same level, there were lot's of differences.
I was surprised in both directions; some of those I thought would be eager and would let me 'get a long way' weren't and didn't, and some of those I didn't expect much from were pleasant surprises. All this had its limitation, however. What I'm talking about is making out and some heavy petting. Lots of kissing, some deep kissing and some fondling on my part. Squeezing breasts and on a couple of occasions getting my hands inside bras and inside panties.
I longed for some mutual attention in this regard, for the girl to do a little fondling of me. I'd heard stories from my buddies that some of their girl friends really got into petting, including mutual masturbation, but I never got close to this. I'm sure that my own sex appeal and technique, the time, the age of the girls I was going out with, and their limited knowledge and experience had something to do with this.
This story relates to the first time I sought to get beyond this level. I met up with a cute girl from a nearby community. She was sweet, but quite shy. She had long dark hair, a great face and eyes. She was rather petite, and had a trim figure and was small busted and had a really good ass. She was a lot shorter than I was, but the fact that we had some other things in common, we were serious students, and were both rather shy, got us off on the right foot when we went out.
We'd had a couple of heavy make-out sessions, and on one occasion got in the prone position, and had a great time rubbing our bodies together, although we were both fully clothed. I'm pretty sure she was aware of my erection. I sure was!
On the night this incident happened we'd been out with some friends. We were by no means steady boyfriend and girlfriend, but had been out together a few times. That night I was driving the family truck, which was not the most romantic or comfortable place to get where I hoped we might go, but we did park in a secluded place out in the woods near town, and engaged in some heavy making out.
She was a good kisser, and she was really getting into it. My hands were all over her, but when I tried to dwell on her small breasts, she was a little resistant. I now think that maybe she was self conscious about her small tits, and perhaps that's why I didn't get her bra off, or even inside it. To my great joy, however, she was not so resistant when I fondled her legs and her crotch, and it wasn't too long before I got my hand in her pants, first outside her damp panties, and then inside them. She had got very wet, and her abundant pubic hair made it a very exciting environment. She was obviously enjoying my fingers in her pussy, (and at that time I knew so little about female anatomy I wasn't consciously focusing on her clitoris), and as the night wore on, I worked her pants and panties down to her ankles, and she was rhythmically responding to my stroking with her hips. The limitations of the seat of the truck, of course, weren't lending itself to many alternatives in our positioning. It was a side-by-side, watch-out-for-the-steering wheel deal.
Needless to say, I had a boner that wouldn't quit, and it was desperate for some attention. But she showed no inclination to fondle me, beyond the great kissing I was getting, and the response I was getting from her pussy. While I was really getting frustrated, I just didn't know how to take that next step, to get my cock into the action. I had the urge to invite her to give me some attention, but was embarrassed that she might be offended, so I didn't.
Finally, we reached a point where she said we had to stop. I don't think she reached an orgasm (as I probably wasn't in the right place all the time), but her panties and pants came back on, and my aspirations were seemingly dashed again.
Out of my frustration I finally ventured a suggestion I hadn't dreamed I'd have the courage to. I explained that all our making out had got to the point that I had to have some relief. She was somewhat puzzled, and asked what I had in mind. I explained that our making out and petting had given me such a hard on that I was going to really suffer if I didn't have some relief. I asked if it would be okay if I jacked off.
She didn't seem to be sure what I was talking about, but she said I should do whatever I needed to do.
With some trepidation, I said I was going to, and with that, opened the truck door and got out. With her looking at me through the open door and me standing by the truck, I undid my belt and pants, and pulled my underwear down, for the first time exposing my cock to a girl. I was as hard as I could ever remember, and my six inch cock was straight up. There was dim light from the truck, but the moon was also shining, and our eyes had adjusted to the dark, so we could both see everything.
I started stroking my cock, and her eyes were riveted on the action. I'd backed up a little way from the open door, and as I neared ejaculation, I moved away even more. I don't think I'd ever been as excited when I was masturbating as I was then, with her watching.
I reached the point at which I could no longer hold back, and with a groan, I shot ropes of cum arching into the air and onto the ground. I'm sure the fact that it had been a while since I'd masturbated accounted for the big quantity of cum I spurted out that night, but I expect the long build-up, and the exciting circumstances contributed to the load.
I'm not sure what she was up to during my ejaculation, but when I regained some composure and looked at her, she was wide-eyed, and gave me a big grin. She said this was her first exposure to such a display, and I sheepishly said I felt better, as I pulled up my pants and re-buttoned my jeans.
I took her home, and we had another passionate kiss goodnight.
For whatever reason, she and I didn't have much contact after that, but I never sensed that she had been too put off by my 'display'.
After that, my courage with women was emboldened, and later I may relate how some of that worked out.
I've often wondered how the first female witness to one of my ejaculations felt about it. I hope she found it an instructive experience.
Keep up your stimulating educational service!