I was without a date for nine months. I don't think that had much to do with what happened. I had several offers but not from anyone I wanted to go out with.
Jerry got off at three but his carpool did not pick him up till five. I let him wait at my place. It seemed natural. It certainly was not sexual; he was far too young for my taste. I would get him a soda or a small snack and we would watch TV together.
Jerry started checking out my breasts. I am a B cup, so they don't usually get that much attention. I like to think with me it is the total package, height, weight, measurements all well proportioned. Jerry's attention to my breasts amused me the first couple of days. When I would catch him, he would look away and even blush. But a few minutes later he was stealing another glance. I was sure he was not only shy but inexperienced too.
I tease him some but only a little. I let him get a few peeks down my blouse and posed a little. But even then I would have a full bra on and would not hold the pose long. No big deal just a tiny bit of teasing.
After about two weeks of this, I got a call that his ride wouldn't get there till eight or later. I knew the driver. Eight or later meant about ten or eleven. I started to think about being alone with Jerry for that many hours. I wonder if I should tease him some more, just for fun. I decided against this idea. Then changed my mind twenty minutes before he came. I was going to show him cleavage a lot. Then right before he arrived, I changed my mind and my blouse again. My bra was back on when Jerry got there.
When he arrived, I couldn't help but think how cute he was. His build was small, just a little taller than me. I started stealing glances, he was just too cute. I made some sandwiches and brought in some cola. When I put the sandwiches on the tea table, he tried to steal a look down my blouse. At that point, I wished I had at least left an extra button open!!
I was covered from ankle to neck. I thought about changing into something less covering. It would just be teasing. I would really be helping him get over his shyness or so I told myself. I sat closer to him. I started a conversation about nothing.
I told him his ride was going to be very late. He just nodded. I asked him if was afraid of being alone with a woman that long. He smiled and said no. I really had no idea what I was going with this.
'Are you sure? I may try to kiss you. Would that be OK?' I had no idea I was going to say that. I laughed to make it light.
A few moments went by. OMG! Then he looked at me, 'No, I wouldn't be afraid. Why should I?'
'Are you sure?' from me. 'Yes' from him. I leaned in. We kissed. We held it for several seconds. It was on the lips but otherwise chaste. 'Still not afraid?' I asked but as a joke. He said no and put his arm around my shoulder. I wondered how far he would go.
'Want to kiss again?' he asked. I told him 'Don't talk, do.'
I cannot believe it now but I was actually telling myself I was just helping him get over his shyness. I did it;he was no longer shy. He kissed me. His tongue was in my mouth;his hand was on my breast. He tried to climb on top of me!
I think I would have taken his virginity if I had protection. We ended up with his mouth on my bare boobs, my hand on his small very hard dick and me sitting on his knee. Between the nipple licks and rubbing against his knee, I exploded.
He had not. I brought him to the bedroom and stripped him. I played with him for twenty minutes before I let him get off. He was naked the rest of the night.
Yes, it happened again.