Roadhead from My Cheerleader Crush over Christmas [MF]

There’s only so much time you can spend with your extended family before it starts to drive you nuts. I was home for Christmas from the city a few hundred miles away where I went to college. I’d had just about enough of White Christmas and playing legos with my cousins so I hopped in my truck and drove out to a roadside bar that hadn’t paid too much attention to our fake IDs when I was underage.

It was decently packed, I figured I’d run into some of the old crew so I picked an open seat at the bar, ordered a longneck and took in the room. Seemed like most of the people were in the same boat as me, escaping from too much family time to the noisy confines of a dive bar.

“Oh my god! Hi!” Lilly wrapped her arms around my neck from behind and gave me a squeeze.

“Hey stranger!” I turned to look at her. She still looked amazing. In highschool, Lilly was the bubbly cheerleader with the long string of disappointing white-trash boyfriends. She was probably 5’8″, with a toned athlete’s body, wearing cowboy boots, jeans that accentuated her perky, firm ass and a snap-button western shirt that was unbuttoned enough to show her pert b-cups.

I must have stammered as I took her in because she winked at me and said, “You look great! It’s been a minute!” I have mentioned in some of my other stories what I look like, think Jason Momoa but not insanely jacked. Back then I was at my fighting weight, though, and probably in the best shape of my life.

She led me over to a table of some folks from highschool, most of whom I wasn’t particularly interested in talking to, but in the interest of hanging out with her I made small talk about school and the city and whatnot. Lilly and I had become friends when we were lab partners in 10th grade and, although we were fairly opposite, maintained a flirty if completely platonic relationship until I moved away.

The bartender gave last call, we polished off our drinks and walked outside. It was cold, a light dusting of snow falling. She put her arms around one of mine and pulled close, “Give me a ride home?” she asked. We headed for my truck and when we reached the passenger’s side door I figured I had had just enough liquid courage to go for it. Reaching for the door handle, I leaned in close and kissed her.

She had, of course, been expecting this probably since the moment she wrapped her arms around me in the bar and melted into me for a moment. Feeling her body pressing into mine was like a dam bursting open, I had felt the attraction between us growing all night and suddenly we had both given into it.

Lilly broke away, “We better get out of this bar parking lot before we get chased out by the bartender,” she said with a sly look in her eye. I jumped in the driver’s seat and we took off. She told me she was still living at her parents’ place to save money while she was in school so I started heading in that direction, taking country roads to avoid arousing suspicion.

Turning on the radio, Lilly was clearly enjoying our little hayride through the backroads. A few more buttons had come unsnapped on her shirt and I could see a black, lacy bra as she gyrated to the music in her seat. She reached over and lightly ran a finger over my ear and down my neck, slowly tracing down my shirt until she hit my jeans. “It’s been too long,” she murmured as she started tracing the outline of my already hardening cock through my jeans.

Attempting to keep my eyes at least somewhat on the road, I groaned as she grabbed my cock through the denim and made a low “mmm” sound.

“Can I see it?” she asked, coyly.

Still trying to not drive us off the road, I said, “Uh huh,” and she undid my beltbuckle, unzipped my pants and let my shaft spring free. There was a slight intake of breath as she looked at my dick in the winter moonlight. The moment hung there between us for a second, me driving with my hard cock out of my jeans and her staring at it. And then she said something I’ll never forget:

“Why didn’t I know your cock was this big in highschool?”

“It just never came up, I guess,” I responded, nonchalantly.

For another beat there was silence between us, just the music on the radio playing softly in the background. Then, as if on cue, we both burst into laughter. After a solid minute of chuckles died down into light cooing, she said, “Well…if I had known, I wouldn’t have bothered with all those other boys…” and she leaned over and wrapped her lips around the head of my dick, swirling her tongue as she did so.

I groaned, swerving a little on the gravel as she took me deeper and deeper into her mouth. I could see in the dim dashboard lights that she had unsnapped her shirt all the way and taken her tits out of her bra as she continued to work my cock, gagging a little bit as she took me as deep as she could get. After hours of flirting and sexual tension, I knew it wasn’t going to be long and I felt the tension building in my balls after a couple minutes.

“Oh fuck, I’m gonna cum,” I said. She kept going, spit dripping from her mouth down onto my balls. As my cock started to throb she sank her mouth onto my cock and I shot rope after rope of hot cum down her throat. She swallowed every bit and cleaned my cock with her tongue afterwards.

Sitting up in the passenger’s seat, she unbuttoned her jeans and wriggled them down a bit, taking my right hand and guiding it into her silky panties and over her freshly shaven mound. “I’m so fucking horny right now,” she said as I slipped a finger inside of her drenched pussy. Slowly I started running my finger over her clit, down her lips and into her pussy. She reached over and started playing with my half-mast cock as I rubbed her with one hand, keeping the other on the wheel.

Whimpers turned into low moans which began to be punctuated with, “Oh god”s and “Fuck”s and, after a fairly short time she clamped her thighs over my hand and rode out a shuddering orgasm on my fingers, moaning my name into my ear.

By this point my dick had reawakened and was standing at attention. After a moment to get her bearings, Lilly reached over and started playing with it again. “Somebody’s ready for round two, I guess,” she said as she leaned back over again and took my cock in her mouth once more. We drove another half mile or so before I realized I wanted it all.

“I’m gonna pull over,” I said.

“Oh yeah? And then what?” She asked, raising her head from my lap.

“And then I’m gonna come around, bend you over the seat and fuck you six ways to Sunday.” I said, already pulling my truck to a small turnout in the wheat field we had been driving through. By the time I got to the passenger’s side door, Lilly was already standing outside in the cold, winter moonlight, her jeans and panties pulled down to her knees. We kissed passionately and she grabbed my cock firmly and said, “Fuck me, baby.”

I spun her around, bending her over the passenger’s seat of the truck and rubbing the head of my cock over her drenched slit. Her tight jeans were holding her knees together as I slid into her, grabbing her by the hips and pulling her towards me.

As I sunk my full length inside of her she groaned loudly into the seat of the truck. I looked around at our surroundings for just a moment, taking it in as I pushed into her over and over again, the moon was full and illuminating the light dusting of snow on the dead wheat. The storied flatness of our midwestern hometown meant that I could see for miles in any direction and there wasn’t a headlight in sight. We were out in the world, a chill wind blowing, fucking eachother’s brains out.

Lilly’s moans escalated to screams, I felt her body start to tense up so I reached up and grabbed a fistful of her hair and pulled her head back lightly and said, “Are you gonna cum all over my cock, baby?”

“Oh fuck, fuck, yes, I’m gonna fucking cum, I’m gonna cum all over your big fat cock daddy,” she shouted into the empty night sky before letting out a long wail and clamping her pussy down on the full length of my shaft. This sent me over the edge and I felt my own orgasm starting to build, “I’m gonna cum baby,” I said, “where do you want it?”

“Cum in me, fill up my pussy, baby,” was all I needed to hear before I sank as deep as I could go inside of her and unleashed another torrent of cum as she rode out the tail end of her own orgasm. When everything had subsided, we stayed like that for a moment, breathing jets of steam like two horses that had just run a race in the cold night air.

A few miles down the road, I dropped her off at her parents’ house. “Let’s do it again sometime, cowboy,” she said and I watched her ass in those tight jeans swaying up the driveway in my headlights.

Source: reddit.com/r/gonewildstories/comments/ea7iv0/roadhead_from_my_cheerleader_crush_over_christmas