So there I am, driving home from a business trip. I had to teach a class in a nearby city, so it ended up being easiest to just drive there, stay in a hotel for a couple of nights, and then drive back after work on the last day. It’s not too bad—I’ve done it a couple of times, and it gives me a nice chance to unwind and take a break.
Anyways, I’m probably about thirty or forty-five minutes out from home, just kind of zoning out. It’s early September, with the sun lazily in the evening sky. Probably about an hour of daylight left. There aren’t really any other cars on the interstate.
That’s when I see her: a girl naked as the day she was born walking down the side of the highway, arm and thumb outstretched in that universal gesture of a hitchhiker. She didn’t look very big, but at the speed I was driving, it was hard to actually tell. A nice, shapely ass, and straight blonde hair down below her shoulder-blades. As I pass, I can see a sad look on her face.
I decide to take pity on her, so I pull over to the side of the road a little past her, mostly because it takes a while to slow down. I watch in my rear-view and side mirror as she seems to perk up, and starts jogging up to the car. She doesn’t have much in the way of tits, I notice, but what she does have are nice and perky. It also looks like her pussy’s bald.
As she gets up to the car, I’m able to ascertain that yeah, she is a thin, petite girl—couldn’t be more than a few inches over five feet, and I’d be shocked if she weighed more than a hundred pounds—with a more youthful look on her. This was no thirty-year-old woman, for sure!
I roll down the passenger-side window as she gets close, and she gets up next to it and leans in, her pert little titties plain and obvious. “Hey,” I say.
“Hi sir,” she says kindly. Pretty voice for a pretty girl. “Can I um ... get a lift, please?”
“What happened?” I ask. I’ve already decided that I’ll help the poor girl out, but I want a little more background, just in case this was some setup or something.
She rolls her eyes. “Fucking senior ... so like, I’m a freshman in high school, just started.” She names one of the local high schools. She looked damned good for a freshman girl. “And like, our school does this buddy system, y’know?”
“Uh, sure, I guess,” I say, looking at her brilliant blue eyes for a few seconds before gazing at her nubile underaged body. Did I mention that I’m a pervert that’s always had a thing for younger girls—not like, kids or anything. That’s sick. But for teen girls, like high schoolers. I’ve never acted on it before, but doesn’t mean I didn’t enjoy thinking about it.
“They pair a senior with a freshman. Y’know, to show them the ropes. But it’s picked randomly, and like, I got the most popular girl in the school. Jenny Tanner.” She says the name with that annoying vocal fry thing all of the teen girls seem to do these days.
“And uh, what’s your name?” I ask, genuinely curious.
“Kaitlyn,” she says. Never thought of that as a blonde name, but whatever. “Anyways, so I thought it was like, going kinda well. She was kinda giving me tips on how to get popular and that sort of thing—I’m like, totally not popular, in case you couldn’t guess—and like, said she and her boyfriend were gonna do something fun with me.”
“Uh-huh,” I say, glancing about. No cars on the road. Not really surprised that a freshman girl would go along with a popular senior’s plans.
“So like, they blindfolded me and took me on a long car ride, said there was going to be a surprise at the end.” Now she got a big pout on her face. “Turns out that surprise was to strip me and leave me at the side of the road to walk or hitchhike back.”
“How’d they strip you?” If the girl’s boyfriend was involved, I already knew the answer.
“Held me down and pulled everything off,” she said. “Jeremy’s on the football team, so it wasn’t like, hard or anything.” She laughs nervously. “I’m just glad they didn’t like, rape me or anything.”
“Mmm,” I say. “So, you’re trying to hitchhike home?”
“Yeah. There haven’t been many cars, and you’re the first who’s pulled up.” She twirling a lock of blonde hair around one of her fingers. “So uhm ... are you gonna... ?”
“Hm...” I say, making a big production of thinking about it.
“I already know how I can pay you,” she says suddenly. Oh really?
“What do you mean?” I play dumb.
“Like, I’m totally ready to give you a blowjob or something,” she says. “And I won’t tell anyone, I promise. But I’m desperate to get home before my parents do ... they’ll kill me if they find out what happened!”
Yes, her lips would look fantastic wrapped around my dick, but I decide to probe just a little. “You’re underage, you know.”
She gives me a knowing smile. “Yeah, but it’s not like I haven’t seen porn. I know how this works. And like I said, I won’t tell a soul.”
“And if I want a little more than a blowjob... ?” I leave the question hanging.
“Like ... uhm ... what?”
“I haven’t gotten laid in months.” It was true—the sex life in my marriage was basically dead since the conception of our last child. “I’d be more than willing to give you a ride if you solve that little problem.”
“Uhm...” she says, contemplating that little fact. “Okay, I guess. It’s not like I have a cherry anymore—I took it with a hairbrush handle a long time ago—so that’s okay. You just gotta make sure to pull out.”
I kill the car. “Mmm,” I say noncommittally. No fucking way I’m pulling out of this teen girl if I can help it. “You just stay there, then.” I get out of the car, close the door, and walk around to where she’s leaning over, ass proudly on display.
“I’m serious,” she says as with one last look to make sure no one’s coming I drop my pants, my cock already rock hard and ready. I stroke it just a little, putting my other hand on her back. “I’m not on the pill or anything.”
“I see,” I say, rubbing between her legs with the hand I was just stroking my cock with. “You’re wet.”
“I ... uh ... kinda like being naked ... and seeing you look at me ... well ... you know...” she mumbles.
“Good,” I say, sticking a finger inside. I finger-fuck her for a little while, listening to her moans. After a little while, I can’t take it any longer, and I know she’s ready.
“I wish you had a condom,” she says as I line up my cock head with her pussy lips and begin to push.
“Never use ‘em,” I say, feeling the warm folds of her teen pussy envelop my cock. It feels like heaven, those velvety folds! And much tighter than my wife, that’s for sure!
So fucking tight I have to give another hard thrust just to get a quarter-inch of my cock in. “Oh fuck!” she yelps. I grab her hips with my hands and give another push, luxuriating in this magnificent pussy. “Oof!” she grunts. “You’ve got a big cock, sir.”
“I know.” Another thrust. My cock is almost all the way in, now.
“You are gonna pull out, right?” I don’t say anything, but give one more push, and finally sink all the way into her. I think I can feel her cervix at the tip of my cock. “I’m not on the pill,” she says as I pull back just enough to thrust deep again. “And I had my last period two weeks ago. I’m probably ovulating right now.”