I'm Jack. Life doesn't work out. I could never seem to get my drivers license. I just seemed to freeze up when I took the driver’s test. It was weird. I could never figure it out. I had taken some driving lessons from my dad a few times but that never worked for some reason. It was like a curse. A horrible curse. So one day I was sitting at the table trying to figure out what to do.

“Are you still beating yourself up over your car fright?” My dad Bill asked.

“Yes. It just drives me nuts. I'm 21 now, why can't I get over this? Why is it so damn hard?” I asked.

“Well I couldn't tell you that. But shit happens you know. Just like getting up on stage. Some people have stage freight and others have car freight I guess. But you can't let it get you down,” Bill replied.

“I know. But still, I got that car just waiting for me, and I can't drive it unless you are in the car with me, and it just sucks. Not to sound like a downer,” I said.

“Well, it didn't work out with me teaching you anything, but I got an idea for you. I have a friend that is a driving instructor. She's been doing this for years now. So she has a lot more experience at teaching people how to drive. And I think you may just be more relaxed honestly. She is really nice and beautiful,” Bill replied.

Then I thought about it for a minute. Maybe he was right. I would be more relaxed with a female driving instructor than driving around with my dad. I thought about it and decided that it was at least worth a try. I mean what did I have to lose? Nothing.

“Well OK dad, if you think that would be good for me. I think I'll do it. You wouldn't steer me the wrong way would you?” I asked.

“Well if I was, I wouldn't tell you the truth. But no I'm not steering you the wrong way. I just think she will loosen up your emotions a little. And things will just go smoother,” Bill replied.

“OK then. Give her a call. Let me know when she can come by or I can come over there,” I said.

“Consider it done. She is nice and not one of those ones where you have to be perfect about every little thing they have you do. Like parallel parking. So consider yourself lucky dude,” Bill replied.

“I'll keep that in mind dad. And thanks,” I said.

So that was nice of him. I didn't even ask him if he had any friends in that department. So the next day, she showed up at our house to pick me up and teach me a few things. I didn't know what she looked like exactly though. So I just waited for a few minutes and I saw a maroon car coming down the street. I thought that might be her. So she came down street and parked. Then she got out.

“Hi I'm Pam. You must be Jack. Your dad said you'd be waiting out here,” Pam said as she shook my hand.

Pam was hot for being 49. She had nice C-cup breasts. She looked like she could be a fashion model. She was that hot honestly.

“Well, are you ready Jack?” Pam asked.

“Yes. I'm... ready,” I replied.

I was just beyond nervous. She was beyond beautiful and she was going to teach me a few things about driving? Well I couldn't help but be nervous. So we both got into my car. She saw that I was more than a little nervous. I think she really noticed that I was attracted to her as well.

“Don't be nervous Jack. I'll make sure we don't go off a cliff or anything like that. So just turn the on the engine and of course put your seat belt on first,” Pam said.

So I put on my seat belt first and turned on the engine.

“Now put it in 'drive' and then we can start driving. Just breathe in and out though. Otherwise we won't be able to get through this,” Pam said.

Then I put it in 'drive' and we started driving. I drove to about the end of the block OK.

“Now turn here,” Pam said.

So I turned as she said to. I drove us around for quite awhile. But of course I was still nervous. And I made a few looks at Pam. She was so hot, I couldn't help it at all. But it was OK. It was better driving with her than it would have been driving with my dad. Nothing personal against him. But it was nice to have her. Although I was still nervous.

“Are you still nervous Jack?” Pam asked.

“Yes a bit nervous honestly. I thought I'd be a little more relaxed than this honestly. But I think I'll be OK,” I replied.

“You just think you will be?” Pam asked.

“Yes. But just be a little patient with me, I'll be OK,” I replied.

Then she did something I didn't expect at all. She kissed me on the cheek. I was beyond surprised by that. Where did that come from exactly?

“Whoa, what was that Pam?” I asked.

“That was a kiss on your cheek. I thought you might like it. I know you are still nervous and that would help you a little. Why, have I offended you?” Pam asked.

I got to say it did help me out a bit. I was less nervous then. Maybe that was why she was so popular.

“Well no, I'm not offended, I'm just surprised. I completely didn't see that coming,” I replied.

“Well, I just thought you would be OK. I hoped it help you out,” Pam said.

“Well, can I have another kiss please?” I asked.

Then she leaned over and gave me another kiss on the cheek. And that helped even more honestly. I don't know why, other than her being very hot. But on the other hand she was nearly 30 years older than me.

“Well thank you for that Pam I appreciate that. But do you kiss all of the people you instruct on the cheek?” I asked.

“No I do not. I've just kissed the one guy that I've really liked,” Pam replied.

Then I did the math on that. Did she really mean just me?

“Do you mean just me?” I asked.

“Bingo,” Pam replied just before she kissed me on the cheek once again.

Then we drove around a little more. Then I really wasn't too nervous anymore. I think that might have been just the trick. So after about another 20 minutes, we made it back to my house.

“Well, I think you did good. Not great, but good. I'm going to recommend that we go out at least one more time. When would be a good time?” Pam asked.

“I guess tomorrow. I'm not busy at all. So is tomorrow good for you too Pam?” I asked.

“Yes Jack. I can squeeze you in tomorrow. How about at 4:00?” Pam asked.

“That's good for me. I guess I'll see you tomorrow then,” I replied.

And just as I was about to get out, she grabbed my hand.

“Wait a minute,” Pam said.

“Yes?” I asked.

“Can we keep that one thing on the down low?” Pam asked.

“You mean you kissing me on the cheek?” I asked.

“Yes that. At least for a little while. That's all I ask,” Pam replied.

Then I thought about that for a minute.

“Well I'm going to want something in return,” I said.

“And what would that be?” Pam asked.

“Can you kiss me one more time?” I asked.

Then she leaned over and gave me a kiss on the lips.

Of course it lasted for more than a few seconds.

“I just meant on the cheek,” I said.

“I know. See you tomorrow,” Pam replied.

Then we both got out of the car and she went over to her car. I watched her drive away and I went inside. I had a big grin on my face though.

“And just what are you grinning at?” Bill asked.

“Nothing, just a good lesson,” I replied.

I think he might have had an idea what had happened. But he couldn't prove anything though. Then we both sat down on the couch.

“OK then. So what does she think?” Bill asked.

“Well she thinks we need at least one more lesson. So she is going to come back tomorrow at 4:00. And we're going to go out again,” I replied.

“OK then. Well at least you had a good first lesson,” Bill said.

Then the next day I was out there at about 4:00. I waited a few minutes for her and she finally showed up. She pulled up and got out.

“I almost thought you were standing me up. I was about to send out a search party,” I said.

“Well I'm an excellent hider though. They'd never find me,” Pam replied.

“Is that a fact?” I asked we both got into my car.

“Yes as a matter of fact,” Pam replied.

Then she gave me another kiss on the cheek.

“Thank you for that. That's most appreciated,” I said as I started driving.

I drove in the same places. But unfortunately I was still pretty nervous. Even though what happened yesterday and she that she gave me another kiss on the cheek.

“So are you still nervous Jack?” Pam asked.

“Yes a little nervous. But certainly better than yesterday though,” I replied.

Then she leaned over and kissed me on the cheek. And that helped once again. But I was still a little nervous, having a sexy lady kiss you on the cheek still doesn't make you invisible to all the other drivers on the road. And Pam really seemed to notice my attraction to her.

“Well, how about you pull over to this parking lot. I think I can help you out with something,” Pam said.

“OK, what can you do exactly to help out?” I asked.

“Well something. You'll find out soon enough. Just drive towards to the back and park there,” Pam replied.

So of course I was a little sceptical. I wasn't sure what she meant exactly. But I just went with it, because I was still nervous. So I pulled into the parking lot and drove towards the back. I parked as well and turned to her.

“Turn the engine off,” Pam said.

So I turned it the off. She leaned across to me and gave another really nice kiss on the lips. We actually started making out for a few minutes. I wasn't sure what was happening exactly. She started kissing me once again, but now she was making out with me? I was making out with an older lady?

“So would you say this is helping?” Pam asked.

“I think so. But let's not just stop now, let's find out how good it can make me feel,” I replied.

“Fair enough,” Pam said.

Then we started making out a bit more. I was getting really turned on at that moment. I mean really turned on. I had no idea where this was heading, but wherever it was heading, I was going along for the ride. So she had put my hands onto her very nice boobs.

“Oh wow, that is a good rack. And these are C-cups?” I asked.

“Damn right they are. Do you like them?” Pam asked.

Then I put both if my hands on her nice C-cup breasts. They felt absolutely great to say the least.

“Yes I do. I love them. I wish one of my girlfriends had a rack like this. I mean damn, have you had some plastic surgery or something like that?” I asked.

“Hell no. These babies are all natural. Pretty good for my age right?” Pam asked.

“Yes, very good Pam. If I just felt these boobs and didn't know how old you were, I'd say you were like 15 years younger. That's how sexy these tits are,” I replied.

“Well, you are a good kisser too you know,” Pam said.

Then we started making out once again. I still had my hands on her really nice boobs. Her boobs were probably the best tits I ever felt in my life honestly.

“Well, sense you got to feel my breasts, I think I should be able to feel something as well. Does that sound fair?” Pam asked.

“Yes. What would you like to feel?” I asked.

Then she put her hand down onto the huge bulge that was sticking out of my pants. She grabbed onto it and held it firmly.

“Oh you want to feel that?” I asked.

Then my dick was getting harder and harder by the second. A nice older lady was grabbing my large dick. I was breathing in and out steadily.

“So does that mean that you like that Jack? Do you like having a nice MILF grabbing on your dick like that?” Pam asked.

I could barely answer that question. I was just dealing with my heart beating very quickly. I had never ever been with a MILF before. Then she began undoing my pants. Then she pulled my very hard dick out. She began stroking it very slowly.

“Holy shit Pam, that is good,” I said.

“Your dick feels really good in my hand. Have you had a lot of sex in the past?” Pam asked.

“Some. But never with a MILF before though,” I replied.

“Well I'll make sure your first time is good,” Pam said.

Then she really started stroking it. She went rather fast. I just laid back and closed my eyes. I couldn't believe what was happening exactly. It felt absolutely amazing to say the least and I had no idea why exactly why she was doing this for me. It couldn't just be to make me not so nervous. I really started getting sweaty then. And so did she. She hand was getting a little slippery.

“Shit Pam, that feels like an angel is stroking my dick,” I said.

“I know, I'm a naughty angel though,” Pam replied.

Then we both laughed a little and she continued stroking my dick like madness. But I knew I couldn't hold my cum forever. So I just sat there and did my best to do so. She kissed me a couple times as she was giving me the best hand job that I ever received.

“Holy fucking shit, you are going to make me cum, I'm going to cum soon Pam,” I said.

Then she came in for another kiss as she was still stroking my dick. Then of course I couldn't hold it anymore. I came everywhere. Her hand was completely wet.

“Holy shit Jack. You came like a fountain to say the least,” Pam said.

“I know thank you. I appreciate that. I think I'm good now,” I replied.

Then we kissed again and we finished the lesson. As we got back to my house again, I made sure not to get out right away.

“Well, call me crazy, but I think we should put in a couple more lessons before you go for the driver’s test again,” Pam said.

“Sounds good to me,” I replied.

Then we kissed again and she got out. I went inside and once again had a grin on my face.

“If I didn't know any better I'd say you had sex,” Bill said as I walked in.