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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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RARBG Handjob

Imagine this scenario. Your dick gets hard, and you are in the right mindset, just ready to rub one out. You hop on the net and find the perfect porno to strut your stuff to. As you get to the best bit, your video starts buffering, your net starts bugging, and your day is ruined. I am pretty sure that we have all been there, and this is why I am introducing a website that will never let that happen.I mean, videos that are downloaded will never buffer, right? So, if you are ready to make a nice...

Handjob Porn Sites
4 years ago
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Hitchhiker

It was Sunday afternoon, around three or so and I was headed back from Manhattan Beach. Imperial Avenue runs all the way from the beach into Inglewood and beyond. I have my thumb out, looking for a ride. Now you might ask why is a fourteen-year-old hitchhiking in a major city, crime being what it is. Well there is a good answer; I just started smoking last year, when I was in the 8th grade and because I am a minor I can't just go buy a pack, so I hitchhike rides and beg cigarettes from...

2 years ago
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A Young Hitchhiker In A Blue Satin Dress

“Fuck you, Robbie!” Anna screamed as she stormed off. She and her boyfriend Robbie, along with her friend Carrie, had been drinking a bottle of vodka stolen from her dad’s liquor cabinet. They sat in the cool, dry grass on the edge of the school football field, Robbie in between the two girls, and as the moon rose they began to get drunk for the first time. They were each twelve years old. Across the field, beyond the bleachers, music emanated from the gym where the junior high dance...

1 year ago
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Lesbian Hitchhiker Part 1

Hello, my name is Megan. Though I don't usualy make a habit of hitchhiking, let me tell you a story about one of the times that I had to, and it led to the greatest decision of my life. My car had broken down one day, so I was stuck there on the side of the road hitchhiking, when a car actualy pulled up. Inside was a beautiful woman, she had perfect DD breasts and long blonde hair, though I have C breasts, I felt a little inadequate. "Need a ride?" She asks, looking me over. "Okay," I say, and...

Lesbian
2 years ago
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The Hitchhiker Chapter 1 Surprise Encounter

My excitement is building as I head out in my SUV and the grocery store is my first stop. I walk through the grocery store and admire all the women as they go about their business. As they pass me in the isle I like to stare obviously at their tits if they are alone. They never say anything but I like how uncomfortable it makes them and causes them to pull a sweater closed to cover their tits. This always makes my cock start to get hard and I hurry through the rest of my shopping and other...

2 years ago
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The Hitchhiker2

A mouth hungrily sucking my nipple and a hand pinching and pulling the other awakened me. I cracked one eye open, trying to orient myself as to where I was and who I was in bed with. There was a little light peeking through the curtains but not enough for me to see who I was in bed with, but then it hit me. I was on my way to California and had hitched a ride with a man name Dak, short for Dakota. Funny thing is, I had no last name to associate with him nor was I even sure his name was Dakota....

Hardcore
2 years ago
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Harley and the Hitchhiker Chapter 1

My wife and I were married forty years, until her passing away from a brain tumor three years ago. Being avid bikers, we were members of a club. After her death, I lost interest in riding and eventually sold our bikes. Our three married children, their spouses along with my three grandchildren have been very supportive. Around six months ago, they began encouraging me to get a bike and go riding again. I politely listened and told them I was not ready to ride yet.oOoToday is my sixtieth...

Mature
2 years ago
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Picking Up A Pretty Hitchhiker

It was a foggy night, while I was driving on the interstate. I had been driving for a few hours and was kind of feeling a little tired. I was listening to the radio and trying to keep myself awake. I had stopped about forty miles back to have a coffee and a bagel, but wanted to get a little further along before stopping for the night. I was a little sleepy, but aware of the road. I wanted to drive a little while longer, before retiring for the night. All of a sudden, I saw a young woman waving...

Mature
2 years ago
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Hitchhiker

On my way home from work one summer evening, traffic was horrendous so I decide to to take a route along the ocean to avoid the congestion. This route takes me by a very popular beach, its a little longer but never any traffic. Cruising along a the beach highway is somewhat desolate, but a scenic easy drive. I see up ahead a young woman in a bikini top and very short cutoff shorts. She has her thumb out hitchhiking, being the gentleman that I am, and not seeing anyone else around, I pull over...

2 years ago
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the hitchhiker

"Shit it's hot."She stood on the side of the road, looking towards the oncoming traffic and wondering if any of those sons of bitches in their air conditioned cars were ever going to stop and give her a lift.When the job offer came through she had to jump at it - one problem - it was a thousand clicks away and she had no way of getting there except on her thumb.Her sports bag was on the ground between her feet, her legs slightly parted and she could feel a slow trickle of sweat running down the...

2 years ago
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The Hitchhiker

It is difficult to tell with hitchhikers. I mean you only get about 10 seconds to suss them out, before you are past and on to the next one. (I do like the way they space themselves out on the slip road, though.) I usually go for a girl. No, not for the reasons you are thinking. God, when I look back; ten years on the road; hundreds of towns, and thousands of miles. Christ knows how many hikers and how often have I gotten lucky? Two one night stands; you know, great at the time, but the...

4 years ago
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Picking Up a Pretty Hitchhiker

It was a foggy night, while I was driving on the interstate. I had been driving for a few hours and was kind of feeling a little tired. I was listening to the radio and trying to keep myself awake. I had stopped about forty miles back to have a coffee and a bagel, but wanted to get a little further along before stopping for the night. I was a little sleepy, but aware of the road. I wanted to drive a little while longer, before retiring for the night. All of a sudden, I saw a young woman waving...

1 year ago
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Hitchhiker

Irene Tamford drove slowly in the early morning sunlight towards the national park; her eyes scanned the road for hitchhikers as she always did at weekends. In the summer she was nearly always lucky, she felt a tense excitement it was always a thrill to pick up a young adolesent male and her plan seldom failed. Irene pulled up and a tall well built teenager put his rucksack in the back and climbed into the front seat. "Its mighty kind of you to stop I've about ten miles to go to the youth...

Swinger
2 years ago
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Dating My Daughter 8211 Part 29 Amy8217s First Handjob

Hello ISS readers. I am back with this series. My quick intro. My name is Aafi. This is a fantasy fictional story. I’m a divorced 41-year-old guy who has a beautiful and young daughter, Amy. She just turned 19 and I haven’t seen Amy in almost 10 years. But now she has come down to meet me. So this is what happened next. After jerking myself, I was too tired. Amy and I both fell asleep pretty quickly. But it looked like Amy couldn’t sleep. She was thinking about what just happened. This thinking...

Incest
1 year ago
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Handjobs

Reddit Handjobs, aka r/Handjobs! I know many of you guys like blowjobs way more than you enjoy handjobs, but if we were to just give handjobs a shot at fascinating us, I think that most of us would feel more than grateful that handjobs exist. I don’t believe that these wonderful things get enough attention from people. So to compensate for that and perhaps give handjobs a little bit of love, I’m going to introduce you guys to a subreddit that is all about handjobs. It’s called, well,...

Reddit NSFW List
4 years ago
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Heres How I Give a Handjob

Let's go over the title of this piece, shall we? It's how I do it. It's not about how you do it or your girlfriend or your wife or both. Not about how your Aunt Lucy did it or that girl in middle school, what was her name? Now, I consider myself a master masturbator. Every guy I have jacked-off begs for me to do it again and again. It's a sex technique that I dearly enjoy and dearly love to do. I love it all but I love seeing the cum spurt up out of his trembling cock more than...

2 years ago
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Fireside handjob

Since the cold weather has come, s*s, hubby and I have been hanging out inside. At night we like to gather around the fire on the couch in the darkness of the winter’s evening and enjoy the its warmth on our bodies. It is so romantic cozying up in each other’s arms while sipping a nice glass of wine. One evening recently, I was curled up under hubby’s arm in front of the fireplace. We were both naked. It was so comfortable sitting there with his arm around me and my breasts pressed up against...

3 years ago
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My first Handjob

My first Handjob.Still school days. Young horny and dating a rather pretty shy brunette girl. We were dating for a few months, having lots of fun as a young couple would have, exchanging passionate kisses, touching each other etc. It was holidays both my parents working as well as my girlfriend Amanda's parents were working. We stayed about a 45 min walk away from each other. Both being home alone, we spent quite a bit of time chatting sexually to each other over MXIT ( sure a lot of you will...

3 years ago
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Fireside handjob

Since the cold weather has come, s*s, hubby and I have been hanging out inside. At night we like to gather around the fire on the couch in the darkness of the winter’s evening and enjoy the its warmth on our bodies. It is so romantic cozying up in each other’s arms while sipping a nice glass of wine.One evening recently, I was curled up under hubby’s arm in front of the fireplace. We were both naked. It was so comfortable sitting there with his arm around me and my breasts pressed up...

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