When I was 16 years old I went on a blind date with a friend Bill and his girlfriend. He was a very handsome guy and was sexually active, which I was not. I was still a virgin.
Bill was half Hispanic and very good looking, so he attracted very beautiful girlfriends too. He had set me up with his cousin, a gal named Wina. He apparently knew her well enough to tell me that if I 'played my cards right, I might get lucky'.
We were all going to go in my car, so I picked up Bill his girl and Wina, who was at Bills house. Wina was a gorgeous gal; plump and with huge creamy white boobs protruding from her low cut dress. However, she was very quiet and shy.
On the way to the party we were going to, Bill told us that another girl we knew, Vicky, had recently broken up with her boyfriend, and that we ought to take her too; that she needed to be cheered up. So we went to Vicky's house and she came with us too. It was, as I recall, known by bill that Vicky and her now ex boyfriend had been having sex too, As it would turn out, I was the only virgin in the group.
The party was in full swing when we got there, and everyone was dancing in the dimly lit living room. I asked Wina to dance a 'slow dance' with me and she did. To my surprise, when I held her to me, she immediately began to rub herself against my leg!
At first I thought I was imagining things but she got even more aggressive as we danced; grinding herself into me!
It was to the point that some other couples were looking at us, and I got embarrassed. So I stopped dancing and took her by the hand into the kitchen.
It went from more to a lot more there. She pretty much pinned me against the refrigerator and began french kissing me like crazy! I apparently was playing my cards right!
When we eventually went to go home, Wina asked me if I'd let Bill drive so we could sit in the back seat, to which I agreed. Bill, his date and Vicky all sat up front while Wina literally jumped on me in the back seat, again french kissing me and grinding against me, which gave me an erection.
Wina felt it and was busily humping her self through her dress against it!
Too soon, however, we were at Bill's house, where everyone but Vicky got out. I had to get out to get to the driver's seat, and it was embarrassing for me because I had this huge hard on and didn't want the others to see it.
Wina wasn't helping, as she wanted a few more french kisses and grinds before saying goodnight. As she kissed me, Bill and his gal just laughed and said something like 'way to go Ken'.
I was really overpowered by Wina, she was way too aggressive for me, and I knew I wasn't ready for her. I got in and started to drive Vicky home.
What had been the 'sexiest' night of my young life wasn't over, however, as it was about to get way better!
I had always been very attracted to Vicky, but never really thought about it because she was dating another friend. She was a short gal, and plump too, but built like crazy with the cutest face and very outgoing personality.
As soon as we left Bills, Vicky says to me 'After all that, you must really need to jack off; I saw your hard on!
I couldn't believe my ears and was speechless, just nodding my head in affirmation!
She immediately went on to say 'If you want to do it when we get to my house, it's ok with me; I know you'll feel much better', and 'I used to watch Phil do it all the time'
It was most obvious that she liked the subject and wanted me to do it for her!
My thoughts and heart was racing! I was half scared to death and excited at the same time!
When we pulled into her driveway, she matter of factly asked again 'do you want to jack off?'
I couldn't contain my heavy breathing and arousal at the thought, but I was speechless. She just kept looking down at my crotch saying 'It's OK.. you'll feel a lot better'.
With a shaking hand I slowly reached down and unzipped my pants. I lifted my butt and slid my pants and underwear down, allowing my penis to pop out. I took myself in hand and began to stroke it in front of her.
She went into her purse and got some tissues, saying 'here, do it into this' and held the tissues in front of my rapidly moving hand, resting her hand on the steering wheel just in front of what I was doing.
Sometimes if I get too excited, I can't cum and I was certainly that, so it took quite a while to get close to orgasm. My hand would brush against hers and the head of my penis against the waiting tissues. Vicky could sense my frustration at not cumming and soothingly said 'it's OK, just relax.. just let it happen' still holding the tissues in anticipation of what they would ultimately catch.
It was the most sensually exciting thing that I have ever done, even to this day. I have masturbated a thousand times remembering her sitting there, by the 'dashboard light' watching me and knowing that I was going to release in front of her.
When finally I started to feel my orgasm coming, my breathing turned to muffled moans as Vicky gave me 'last minute instructions'.. 'you're almost there, just let it happen.. let it cum'.
Most of my cum hit the tissues but a lot didn't. Some went on her arm, and about everywhere else; it just kept flinging out!
She had to get more tissues to clean me and that which got on her arm up, exclaiming 'boy, I guess you really did need to do that!'
Vicky started dating another guy after that and we were never together again, but I'll always remember that 'blind date', and I know how much fun her new boyfriend was having!