Wendy (Patreon)

Hey everyone. I know I'm gonna start doing shorter-form stories but what better way to end the tradition than with my longest story to date? Well, hope you enjoy! 

“b there in just a few go ahead and hop the fence w/o me”

That’s what the text I got a few minutes ago said. As I made my way through the midnight, barely-lit streets of Gravity Falls, I almost couldn’t believe my fortune. Illegal after-dark swimming at the pool with none other than Wendy Corduroy? It was every dude in town’s dream.

Per her instruction, I take a few steps and climb over the chain link fence around the pool and take a seat to wait for her. It was an interminable few minutes of sitting on a lawn chair by the poolside. I scroll absentmindedly through my phone, fearing the worst. Did she ditch me? Was the whole thing a prank?  

But soon enough, I hear a rustling from the other side of the pool, and soon enough, the red-headed goddess herself hopped over the fence with a smile, dressed in her trademark green flannel and black jeans.

“Hey dude, sorry I’m late. You know how it is,”  she said, landing with grace. Let’s get changed and go for a dip!” Wendy beamed at me.

She made her way into the locker room. I had worn my trunks to the pool, so all I had to do was take my shirt off.

Wendy, on the other hand, re-emerged from the locker room in a tight, bright red bikini that showed virtually every flawless curve of her body. It took all my willpower not to shamelessly ogle her, but I couldn’t help but steal glances.

“C’mon, lets get in!” She makes a running start for the pool and makes a feet-first jump into the deep end. I, on the other hand, make a more cautious entrance.  

We splash around for a while, laughing at each other’s jokes and making innocent conversation, when suddenly, a spark of realization lights up on Wendy’s face.  

“Hang on, I’ve got a great idea!” She chirped, climbing out of the pool and bolting to the locker room once again. She came back, for some reason, holding a basketball.
 

“Wanna shoot some hoops?” She indicated the water basketball hoop at the far end of the pool, which I had failed to notice, probably because I had spent my whole time there staring at either my
phone or Wendy’s body.
 

I kinda stammered out something about how not-good at sports I was. I don’t really remember what I said, but I’ll never forget what Wendy said next.

“Well in that case, wanna make it a little more… interesting?”  

“Interesting?” Was she gonna put money on the game or something?

“You have to make a shot all the way from the other side of the pool.” She began dribbling the ball as she explained. “If you make the shot, I’ll lose my top.” She shot me a sly grin.  

I froze. Well, she was right, that was definitely more interesting. I immediately reach for the ball, but she snatches it away over her head.  

 “But!” she continued. “If you miss, you have to lose your shorts!” Her grin expanded even wider.

I look at the pool. It’s pretty damn big. I guessed the odds of me making the shot are about 50/50. I started to contemplate though, I’d spent a good amount of time in the pool. I might have had some… shrinkage? Not the most impressive thing to show off to Wendy. But in all fairness, any chance to have Wendy Corduroy get her tits out for me wasn’t one I was gonna pass up, regardless of what the penalty was!
 

“You’re on!” I exclaim. Wendy thrusts the ball firmly at my chest that I nearly fail to catch.  

“Off to a good start.” She chuckled at me.  

I walk to the opposite end of the pool than the one the hoop is on. I stare at my target. It seems so much farther away than I thought it’d be.  

I check the ball a few times. Was that what it was called when you dribble it before a throw? I’d seen people do it so it seems like a thing regardless. I pick up the ball and begin to line up my shot, taking my time. I only get one shot at this.  

“Stalling will get you nowhere!” shouted Wendy, calling me out.

“Fine.” I sigh. Here goes nothin’.
 

With much trepidation, I throw the ball. It has a beautiful arc, making contact with the backboard. It rolls around the edge of the rim…

And rolls off the edge, splashing down into the water below.

“Bummer, dude.” Wendy says, a giggle in her voice.  

“Oh, c’mon, one more try!” I plead.

“Sorry dude, that was a clean shot, no mulligans.” She smirked, awaiting your humiliation.

 “Ugh, fine… How do you want to do this, should I-” I began to say, but didn’t get to finish. Wendy tucked a hand in the front of my trunks and yanked downward, sending them to the floor with a wet plop.
 

She gazed downward. All that was there to witness was a shriveled raisin A smile formed on her face, which she quickly covered with her hand. A few loud snorting snickers escape her nose as she stared unblinking at the freshly exposed sight of pool-shrunken genitals. She could contain herself no longer and she broke into full blown belly laughter.  

“Holy jeez, dude. I’ve fooled around with like, most of the town, and I don’t think I’ve ever seen a wiener that small!” She blurted.  

“I- uh- it’s shrinkage from being in the pool!” is the defense of myself I’m able to muster up. I mean hey, it’s the standard sitcom defense.

“Pff, nice try, dude. I know cocks, and there’s no way that thing expands into anything that can hit a g-spot.” She manages to pronounce now that her giggle fit was subsiding.
 

“Oh, I’m pretty sure you’d find it gets plenty big enough.” I say unconvincingly.

“Well then, let’s see about that.” Before I can ask what she meant, Wendy had untied her bikini top and sent it to the ground with the second wet plop of the night, leaving her remarkable bosom there for the world to see. Her wet flesh glistened tantalizingly in the moonlight and the chill in the night air had left her skin goosebumpy and her nipples as stiff as they could be. A sight to behold.

Speaking of stiffness, the same thing began happening to my shrunken package, almost instantly expanding into it’s full ‘glory.’ Wendy, once again, was far from impressed.  

“Pff, yeah, it’s what, three inches? No way that’s hitting anyone’s g-spot.” She grinned. “But, I’ll let you try.”  

“What?” I blurt.

“You heard me. I’m no tease. I showed you my tits, and you got a boner. The least I can do is let you… evacuate the troops.” She chuckles. “Besides, not like it’ll take you long. Haha!”  

I was stunned, despite all the teasing, Wendy was about to let me fuck her? How unreal was this?

While I was too stunned to do anything, she bent herself over one of the poolside chairs and slipped off her bottoms, to reveal her cute little pussy between her creamy white thighs.  

“Ready when you are. Just lemme know when it’s in, I don’t think I’ll be able to tell, haha!” she teased. Boy, as nice as she was, she was also merciless.
 

I kneel down. I take hold of her hips, line myself up, and slide it as deep as I can go in her warm, wet, inviting crevasse. The soft, inviting flesh sends a shockwave of pleasure through me. Wendy doesn’t flinch. I don’t move.

“C’mon, put it in already!” She teasingly suggests, turning around. Until she sees I already have.
 

“Oh? Looks like I was right!” She smiled.
 

The eye contact of her smiling face was too much for me to bear. My entire body quaked as I fired one off, balls deep, yet not deep enough for her to even feel.  

“Ooh, looks like that did the trick.” She giggled again, pulling herself off you and getting up. “I’ll keep your little secret, emphasis on little, but don’t expect me to ever let you live this down! Hahaha!