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Surprise Hitchhiker Handjob.

Tags: milf, car
A quick story about a true event that occured last winter.
One Friday morning, last winter, I was running errands while the kids were in school. It was cold out, and a light snow was falling. As I was driving to the store to do some food shopping, I noticed this guy hitchhiking on the side of the road.

I normally don't stop to pick up guys thumbing, but he was young, maybe 20 or 21. I could tell that he was freezing, and, being a mom, I felt bad for him. When he got in my car, he was shaking, and his face was red from the wind.

"Cold out, huh?" I asked him.

"Freezing," he replied. "Thank you for stopping, I've been out here about an hour."

I turned the heat on high and aimed the vents toward him.

I said "This should warm you up."

I introduced myself and asked him where he was going. He said that his name was Scott and he was going to the subway station and then into the city. The station was 2 towns away, I had plenty of time so I decided to take him.

During the drive, we engaged in small talk. He told me that he didn't have a car because his insurance had expired, and he couldn't afford it, so he sold it. He was going into the city to go job hunting so he could get another car.

We talked about our families, the weather, all sorts of things. He told me that he lived at home with his parents, and that they were getting on him about going back to work and getting another car.

He was cute, maybe 5' 10" tall, average build, with black hair. He was wearing khaki pants with a blue shirt and a brown winter coat. He looked nice and was very polite. I looked a mess, my hair was messy, I had on sweatpants and a heavy sweatshirt with out a bra, with a light jacket. I hadn't showered. I had woken up about an hour before and wanted to get things done.

During the conversation, he asked me if I was married. I told him that I was divorced and had 2 young boys.

"Oh, I'm sorry." He said.

"Don't be," I replied. "I'm not, best thing that's ever happened to me."

I didn't know if it was a pick up line or just part of the conversation. We chatted more and when he asked what I did, I told him. He looked a little stunned when I told him. He abruptly changed the subject, I could tell that he was uncomfortable talking about it. We drove and talked for a little while longer when I told him that I was still half asleep, and needed a cup of coffee.

I pulled into the drive through, ordered my coffee and asked him if he wanted one. He told me that he had just enough money for train fare, so I offered to buy it for him. At this point, we were about 2 miles from the train station. Down the street is a large strip mall with alot of parking, and I asked him if it was ok if we parked for a bit while I had my coffee.

Now, my mind was already in motion, I wanted to give this kid a treat, but I had to feel him out. I asked him if I was holding him up, he said no and that he'd like to "hang out" with me for a while. I explained to him that I had stuff to do before the kids got home, but had about an hour to kill.

The parking lot was much too busy for what I wanted to do, so I suggested we find a quieter place. There is a lake in the area with 2 parking lots, a large one and a small one, I chose the small one. It was beautiful, there was light snow on the trees, the lake was frozen, and we were alone.

We sat for anothet 10 minutes or so.We talked some more when I asked him if he ever had a massage.

"A happy one?" he asked, blushing.

"Yes." I replied.

"No, I can't afford them," he said.

"If I had the time, I'd give you a free one." I told him. 

This parking lot is small, you can't see it from the street, but the freeway is right next to it, theres a big embankment, then the highway. If you look down, you can see into the cars. We had been sitting there with the engine off, and it was cold in the my car. Also, the windows had fogged up.

I turned on the engine to warm up the truck and unfog the windows. Then I opened up the glove box to grab some napkins. I leaned over and began rubbing his cock through his pants.

"Pull your pants down." I told him.

"Huh." he replied.

"Pull your pants down!" I said, in a commanding voice."I'm going to brighten up your day."

Needless to say, his khakis were down in record time. I told him to put the seat back down and lay back. I lifted my sweatshirt, exposing my breasts and went into my purse, took a small bottle of hand lotion I carry and put it on my hands. I pulled his shirt half way up, exposing his stomach.

"You look like you've had a rough morning, just relax and let me make it better." I said to him.

He couldn't believe what was happening. He laid there, looking at my tits with this bewildered look on his face.

I looked at him and said, "You can touch them."

I pulled his pants down further, below his knees, spread his legs and began rubbing his cock. It was hard almost immediately, the benefits of being 20 years old I guess. I took some lotion, poured it on the head and proceeded using long, slow strokes, from the head, down the shaft and back up to the head.

I was parked with the front of my car facing the embankment. We were alone in the lot but anyone on the highway, looking down, would be able to see what was happening. I actually heard a few beeps coming from up there.

He was gently rubbing one of my nipples while I continued, for about 2 minutes, using the long, slow strokes. I could tell, it wasn't going to take this kid long to get off.

"When's the last time a girl made you cum?" I asked him.

"This past summer." he said.

"So," I said, "I bet that you have alot built up in there, just aching to come out."

I began to stroke a little faster, gradually picking up intensity. I talked to him the whole time to relax him.

I asked him."Have you ever been with an older woman?"

"No." he replied.

"Now you can tell all of your friends that you got a handjob from a milf." I said with a smile.

He replied. "They won't believe me."

"So what..you know that it happened, that's all that matters," I said.

I poured a little more lotion on his cock and began stroking furiously.

"Now let's see if we can get all of that stuff out of there, huh." I said.

He was very close to cumming. I didn't want him to cum on my seat, or the floor, nor did I want him to come on his shirt. I grabbed some napkins and began to stroke a little faster.

"Give it to me," I commanded, "Give it to me, c'mon."

It took all of about 20 seconds.

"I'm gonna cum." he said.

I grabbed his cock and pointed it toward his belly. With my other hand, I held the napkin in front of his cock head, so he wouldn't ruin his shirt. I felt his cock expand in my hand, then shoot a massive load of cum on to the napkin, and his belly.

"All of it, give me all of it." I said.

A few more squirts came out before he finally stopped.

"Wow." he said.

"Not a bad way to start the day, huh Scott?" I asked.

I took a bottle of spring water I had, cleaned up his belly and me hands, pulled my shirt down, and told him to pull his pants up, it was time to go. On the way to the station, I gave him my card and told him that I'd give him a break. If he ever came up with $50, I'd give him a real massage at the shop.

When we got to the station, he put on his coat, leaned over and looked at me.

"Thank you." he said.

"You're welcome Scott, have a nice day."

"I already have." he said as he walked in the station.

I then continued on, did my errands, and was home in time to meet my boys at the bus stop. To this day, I don't know why I did it. I didn't wake up horny, in fact, I hadn't slept well the night before and was tired. I also don't like driving in snow, so when I left home, I wanted to get done as soon as possible.

I think it was the mom in me. I saw this young man, cold and a little wet, hitch hiking. When I spoke to him, he sounded a bit sad. I felt bad for him and wanted to brighten up his day. He hasn't come into my shop, so I don't know if he found a job, but I wouldn't mind doing it again. I hope I see him.
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