It was a very memorable third date to say the least.
This happened back when I was 17. I started dating this boy named Robert. We had kissed the first time on our second date and it was a good night kiss when he brought me home. The next weekend we again had a date. During the evening we shared a kiss off and on all evening.
My house was several hundred feet from the street. When Robert got me home this time our good night kiss just went on and on and both of us were sure feeling it. After a while I felt Robert's hand on one of my tits squeezing on it. It felt so good. I'd never had a boy touch me this way before.
A few minutes later Robert reached up taking my hand and he moved it down to his lap area and on his very hard penis. It felt so big to me as I'd never felt a boy there before. Only babies and very young boys while baby sitting. Robert then told me 'oh Jamie. You're driving me crazy. Feel what you're doing to me'. I wrapped my hand around his penis through his pants. It felt so hard. Robert then said 'Jamie, I need to get off so bad. Will you do it'? I asked him 'what do you want me to do?' not knowing any better. Robert then said 'you know. Jack me off'. I told him 'I'll try'. I soon learned this was sure a stupid thing to say.
Robert reached down and undid his belt and pants and lowered them. He then pulled down his briefs. There was enough light in the car from the street lights that I could easily see his very erect member. Robert looked at me and said 'please do it'. I slowly reached over feeling a real live erect penis for the very first time. It felt so smooth. As I touched it and put my hand around it Robert said 'oh yes! That feels so good'. He put his hand over mine showing me how he wanted it held which was just below the head. He then showed me the up and down motion and then removed his hand from mine. I felt quite excited at the time as here I was giving a boy a hand job for the first time. It wasn't long and Robert went to thrusting his hips some and making some groan sounds and finally a grunting sound as the first of the squirts of cum shot from his penis and ended up on his shirt. Then another and another. I was so thrilled at seeing this for the first time knowing that it was me that got him so aroused. And of course this was the first time I'd ever seen a boy's cum. It also covered my hand.
We wiped off the best we could with some tissue and Robert pulled his pants back up. This then became a regular part of our dating and I also reciprocated showing Robert how to use his fingers and get me off. For a while Robert couldn't keep his hand from up my skirt as he was constantly wanting to feel my legs. This really aroused him. He has now calmed down some but when the time is right he is a real animal down there. And he loves to have me rub his penis against my inner thigh and let him cover it with his cum. And to think this all started on that third date.