One of [M]any [F]un Stories (somewhat lengthy) | 2016

So, I briefly touched on this young lady we'll call 'Naomi' here, and this is just one of our many experiences together.

I'll add the oft-used "if you like, I'll post more"... but chances are I'll add a few more because a) I've literally told no one of this little relationship we carried on. Why? No clue, you'd think being in your 20s banging a hot MILF would be serious bragging material... but at the same time I'm fairly private...and b) it feels good to finally let someone in on this little secret... Sooo, yea. Ok. On with the show...

Naomi and I met via Craigslist back in 2006. I was fresh out of college, fresh out of a Freshman-to-Senior year relationship, ready to cut loose as an "adult". Initially I was looking for a place to rent, but stumbled upon "that" section and decided to give it a go.

Naomi was in her early 30s, I was early 20s. She's about 5'5, milky white skin. Curly red hair, piercing bluish green eyes, and nice C, almost D cups.

This particular meeting we decided to check out a new bar near where she was living. I mentioned to her I'd always wanted to double-team her with another guy, and she mentioned she used to "hang out" with one of the bartenders. Perfect. We get there, drinking, smoking cigarettes... having a good old time. The bartender is kinda short (I'm 6'4ish, so nearly everyone is "short" to me), stocky, kinda like a NFL running back. He hooks us up, comes and talks to us off and on. We're flirting with her heavily, she flashes a boob here and there. Playfully rubs my crotch and whatnot.

I'm getting horny, he doesn't get off for another couple hours... we decide to bail, and he understood.

We get to her place, driveway goes up, and it's pretty steep into a carport. I pull in, and by this point I'm feeling frisky, and bold. We get out, I sit her on the trunk of my car, and we start making out. Grabbing her hair, boobs... all out.

Come to find out... no panties on under that skirt.

I start fingering her... she's wet as wet can get. I pull a finger out, start to lick it, so tasty... she pulls my hand towards her mouth and sucks on it a bit.

She hops down, pulls my pants down and my hard-as-steel cock flips out, nearly smacking her in the face... she slowly starts to lick around the head, simultaneously stroking the base and playing with my balls.

My knees are getting weak... feels so damn good. I grab the back of her head and tilt it up towards me:

"show me how deep you can get it"

She smiles, takes a deep breath, grabs the base tightly with her left hand, braces herself with the right on my thigh and starts to slowly swallow my dick. It's going in.... little by little, she's getting a lot in there... feeling the back of her throat start to expand, slight gagging is HOT. Probably one of the best feelings out there.

She nearly gets me all the way in, then pulls back, gasping for air, some drool running down her chin. She wipes it off, "you like?" Me: "do you really have to ask?" We laugh a bit. I sit her back on the trunk and spread her legs.

Sidenote... while it's well past midnight and we're fairly secluded, being outside and "in public" about to enter her is really turning me on.

I slide in with ease, considering how wet she is and how well-lubed my cock is with her spit. She grabs my neck, I have a leg in either hand... I start out fairly slow and steady (it wins the race), pulling her a bit closer, feeling my balls slap against her ass... the sound gets louder as I speed up, her wetness dripping everywhere.

She pulls herself up a bit closer "you are so bad. shy boy fucking me on the trunk of his car in my drive way?"

Me: "I'm full of surprises"

I speed up, thrusting a bit harder each time... she's moaning, squeezing my neck tighter... her tighter grip is encouraging me to keep the intense pounding up. The moans turning into "oh shit" and little screams. I feel her pussy start to squeeze the life outta my cock, eyes roll in the back of her head... and her cute little grunt that signals orgasm... followed by a fairly loud "holy shit"...

At this point, I feel like I'm gonna explode and also getting kinda nervous that her yelling might alert someone to our little escapade.

I pull out, my cock is glistening.. I waddle inside with my pants around my ankles.

We get to her room, both get naked, I turn her over on all fours, push her head into the pillow as I enter her pussy from behind, smacking that cute little ass, not much longer after that "shit I'm gonna cum" she perks up "cum on my tits, no tank top this time" (in a previous encounter where she gave me amazing head, I shot all over her chest, kinda drenched the tank top she had on).

I laugh, "well turn your ass over".

She turns over, lays back, one hand playing with her pussy, the other squeezing a nipple "c'mon, show me how much you can shoot this time"

All this encouragement sends me through the roof... 5 or 6 strokes of my cock "here it comes!"

She sits up a bit, pushes her tits together, I stumble closer, hitting my shin on the bedside... but I don't flinch, and just unload a hot sticky mess on her tits, arms, some on the bed... so fucking hot.

She loves it, giggling, licking some off her arm.

I jump on the bed and lay next to her "damn I hit my leg on your bed"

Her "well, was it at least worth it?" Me (sarcastically)"well, I guess"

We laugh and talk a bit more, I leave about an hour later.

The end!

Also: I was a bit disappointed the threesome didn't happen that night, however, based on everything we DID do, I considered it a win.

Hope you liked!