tagFirst TimeYour First

Your First

byRiven___Caulfield©

The following story is true. It contains nothing unusual. Nothing that hasn't happened a million times to a million people. This story's not really mine, and I will give credit where credit is due. It's the story of a teenager jerkin' off. That's about it.

My family moved around a lot. Now once upon a time, we lived in Saskatoon, Saskatchewan. Despite popular myth, Saskatoon's not a bad town. Though, not a great town for a teenage kid with nothing but Home Schooling and a mountain bike.

Yes, fine, I was home-schooled. And I do regret it's rendered me socially maladjusted, but that comes with a satisfaction that only the socially maladjusted can know.

Now, this story begins with my older brother.

Upon cleaning his room one day, my mother discovered his stash of porno magazines. She demanded he throw them out, but throw them out he did not. Oh, he threw out ten or so, just so as not to raise suspicion. The rest he tucked neatly under the front steps – a huge hollow box-like stair of concrete.

I learned none of this, until I noticed a shiny cover jutting from under the porch one day. I got down on my hands and knees and dug away at the gravel until I could pull it out.

Gallery magazine.

My gut tightened – I felt sick with nerves. I tucked it under my pants and pulled my shirt over top, and dashed through the front door and up into…

Hey, we all know where this story goes. The bathroom had a lock.

Now I must admit, I was quite enchanted with the sight of a woman's full-fledged features for the first time. I recall my favorite spread; a redhead who I swear was natural. Looked like a girl-next-door, posing against one of those ancient Chevy trucks. Her pale skin glowing before the chrome and candy-apple shine. Wet marks on the leather seats.

But this story's not about her, either. This story is about the first sex story I ever read. I can't take credit for it. It's not even a story – supposedly, it's true. It's one of those letters people send in to stroke mags.

I can't remember any names. Or the title. But phrases. Images, are burned in my memory. I'll try to recreate it here for you now, as best I can. The letter was first-person, but I'll give you third;

Jimmy. Jimmy's a young lad of eighteen years, living in a small town in the American Midwest in the late fifties. He wears wool pants and swell checkered shirts. He's had a girlfriend or two, but never gotten further than first base.

Now that's not to say Jimmy's some loser. He's any guy just like you or me or your brother or your dad. He just hasn't been laid. He's on the football team – though he's just the guy who kicks the ball. And it's such a small town, no one really gives a shit about the sports anyway.

So back to Jimmy. Now Jimmy was hoping to cruise off with his friends for the summer between his graduation from high school and induction into college. But Jimmy's mother wasn't havin' it. Before he even got to throw his grad cap, she'd arranged a nice little job with the lady down the street – we'll call her Mrs. Robinson. He'd be mowing her lawn, doing odd jobs for her for the rest of the summer.

(cough cough)

So off Jimmy goes to Mrs. Robinson's. Here's to you, Mrs. Robinson. Jesus loves you more than you will know / whoah whoah whoah / whoah whoah whoah.

When he arrives, she meets him at the door in a t-shirt and sweat pants. He swears that even through that baggy shirt, he can see her nipples. Her breasts are so full, her hips so curvy, he starts a sweat just following her through the house as she pointed to this and that, explaining his duties.

Soon he was indeed working his ass off, but staring at her the entire time. He'd be vacuuming, making sure she didn't see the way his less-than-docile hardon was nearly succeeding in busting its way through his jeans.

It became apparent that she had no interest in him, and he contents himself with jerking off at night to the etched-and-burned glances of her in her swimsuit, sunbathing. Her in her robe. Her smiling at him, while his dick screamed at him. Throbbing so hard it hurt.

One day, Mrs. Robinson is sunbathing in the backyard. As he gathers some tools for the garden in the garage, he suddenly finds that in this dark and secluded place that he has the ideal location to 'peep' on her, as he called it, without her knowledge through a small window.

He goes on to explain in great detail that she wasn't what you'd call beautiful, but she was very, very sexy. Her body, apparently, was the sort that Marilyn Monroe might have wished to possess. And as she laid back in that bikini, her breasts overflowing the flimsy top, he shoved his cutoffs down and started stroking his cock. Spitting on the head, he rubbed and stroked and stared at her body. She wasn't what you'd call beautiful, but she had become his version of perfect.

Trying to make it last as long as possible, he takes twenty minutes or so. He goes fast sometimes, so his hand becomes a blur. Sometimes he just strokes the shaft with two fingers. He has eight different techniques or so, but he never moves his eyes from her. From her hips. Curvy legs. Thick, dark hair. Full lips. And he wants her so goddamn bad. He's aching for it.

Stroking, stroking. Teasing himself. But he takes twenty minutes or so, and before he squirts she leaves the backyard and goes into the house.

He waits, patiently. Sweating in the dark, his cutoffs and tightie whities at his ankles, he nervously strokes his cock and waits for her to come back. He won't take any more chances, he decides. When he comes back he'll just get off and be done with it.

Click – the garage lights turn on and he spins in time to see her in a terrycloth robe. And he spins fast enough to trip on his cutoffs and tightie whities, and fall flat on his rock-hard cock.

"Just what are you doing?" she demands as he manages to get to his feet. He reaches for his cutoffs, but "Never mind those," she tells him. "On second thought, it's obvious that you were peeking at me and playing with yourself, is that right?"

"Y-yes'm," is all he can say. He looks at him strangely.

"Don't you have a girlfriend to do it to?" she asks. He shakes his head. "You mean you've never had that thing in a girl at all?" He shakes his head.

"Oh," she says. "Your prick looks so nice and hard, and it is a little bigger than my husband's. I'd love to let you stick it in me, but I'm married."

She lets the robe fall open a bit. Enough to see she's not wearing anything underneath.

"Alright," she says. "Touch it." And now, propping herself up on the dryer, she says; "Go ahead – fuck your fist while you look at me."

And what can Jimmy do, but keep on jerking his dick in front of curvy Mrs. Robinson? Soon, she's spread her legs, and he can see the pearls of moisture under the thick curls of dark hair.

She asks him how she compares to girls his age. He says he hasn't seen many of them naked, but she's the most beautiful woman he's ever seen.

She tells him to come closer, and spreads her legs.

Gripping his cock, she strokes it. This guy's in Heaven. And now she works it through her pussy hair, making it slick with her juices. And this guy's bouncing between cloud Nine and Thirteen.

"Oh," she's mewing. She pushes it against the flat of her pelvic bone. Her skin is so hot. "Oh," she says, rubbing it against her belly. "Look how far in me it would go!"

His head is spinning. He barely knows what the fuck is going on, but when she tells him to take his cock and stroke her pussy with it, he does.

And soon she's moaning, and squirming against him.

"Oh Jimmy," she says, "Your prick feels so good rubbing my pussy, but let me show you where it ought to be." And then she grabs him with her ankles and pulls him in. She's so hot and wet that he begins to come practically on contact, and she's not helping; "Fuck me, Jimmy! Fuck my pussy! Your prick's so hard! Fuck me!" And so within three thrusts or so he's yelling and coming and squirting all over the place. But Mrs. Robinson's not done – she keeps on humping him until she lets out a shriek, and falls back limp.

Then she tells him to get dressed and return to his work, and threatens him storely to never tell on her. He promised not to, and swears he never did until he wrote the letter.

I didn't write that story, and looking back now it is pretty cliché. But I guess you never forget your first stroke story. Just thought I'd share mine.

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byRiven___Caulfield© 0 comments/ 157750 views/ 0 favorites

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