I was 19 and Diane was 15, we were out on a date at the drive-in movies (remember those), we had gone out many  times and never did get past her groping my dict through my pants and our making out, she never did let me feel her up even. Both her and I were virgins (at least I was a virgin with a girl, but that's another story).

About a half hour into the movie, Saturday Night Fever believe it or not, when we hopped into the back seat which we  had done many times before and started to make out she grabbed my cock through my jeans like she had done in the past and of course I figured that was as far as she would go as usual, but to my surprise after a few minutes she unzipped my jeans and to it out through my underware and started to stroke it. I figured maybe this time she might let me at least feel her up so I ran my hand up to her shirt and started to rub her nice tiny tits (I had always had a thing for small tits and still do) and she seemed to like it so I unbuttoned her shirt and took of her bra to uncover the most beautiful set I have ever seen, she kind of moaned as I started sucking on her hard nipples. I had always been a little shy about anyone seeing my dick since I was always small, back then only about 3 1/2" and am still only 4" now, but she either didn't seem to care or didn't know any better that many were much bigger. She started to sttroke my cock with her tiny hands which felt so good and to .

We were still making out, she started playing with my balls and I thought I would explode, it was then that I decided to see just how far she would let me go. I took my other hand that wasn't playing with her tits and stared to rub her through her shorts and she let me, after about a couple of minutes I started to unzip them and play with her through her underware, my god she they were soaked. I then put my hand into them and got feel of my first pussy oh what a feeling. She asked me to take off my pants and if I would she would let me take hers off, didn't have to aske me twice. When I saw her for the first time I was amazed at how sexy it was, she  had a nice small path of hair and such pink lips. I started to rub her pussy and then I stuck my middle finger in her, she had a very small pussy and it was fairly tight with just the finger. After a little while she asked me if I liked her "lovehole' as she called it, I told her it must be the best in the world.

 We did this for a while me fingering her and she stroking me, when she asked me if I loved her, well we all know I told her yes. She then asked me if I wanted to rub my thing against her lovehole which I jumped at since I have been waiting to pop her cherry for a long time and I wanted to see what fucking felt like.

While rubbing it up against her I got it to slide into her pussy, I almost pulled out because I didn't think she would let me but didn't since she didn't say anything. Icouldn't get over the fact that she was letting me do this. She started pumping up against me as I drew it up she would push up hard like she was worried I would take it out of her. I will say this she was and still is the tightest I have ever had and remember I am small and don't fill up a lot of girls.

 After a few minutes I started to cum inside of her and we just fell into each others arms, that must have been the biggest load I ever shot.

We did it several more times during the next couple months, on the third time she asked me if I would lick her pussy but this is also another story.

She broke up with me but I will never forget her and believe it or not although I told her I loved her that night so I could get laid, I realized that I did indeed love her and still miss her to this day.

But boy was that night great :).