You finally convinced Kristy to go out with you, mostly by impressing her with the suggestion that you owned a boat. I mean, sure, it’s just a little tinny, and technically it belongs to your uncle, but still, a boat’s a boat. The weather was unseasonably warm, but even so you were more than a little surprised when Kristy turned up in a skimpy red bikini.
“Ready to go?” She asked sweetly.
“Uh, yeah...” You replied, feeling ready to go in more ways than she realised. The sight of her massive, soft breasts barely contained by that little top sent the blood surging to your cock. It sprang to life in seconds, and only a quick turn to the boat kept Kristy from noticing the bulge in your trunks. You climbed aboard, and stretched out your hand to help her in. As her fingers brushed yours, you felt a little electric thrill run through you, setting your stomach fluttering and your cock twitching.
“I thought we’d just cruise up the river to this little dockside bar,” You say, just managing to avoid leering down her top. You search through your backpack for the pair of mirror-shades you know are in there somewhere, glancing up to try and make occasional eye-contact with her.
“Sounds good,” She smiled and looked around at the scenery, “You know, I’ve always really enjoyed boating, and...” She kept talking, but her words disappeared into the dull roar of blood in your ears. With the mirror-shades firmly on, you were availing yourself to a more detailed look at the boobs you had been dreaming about for months. Large, soft. perfectly formed... You were lost in the depths of her cleavage, aware only of the incredible sight of her enormous breasts, and the aching hardness of your cock straining against the fabric of your shorts.
“...So lets get going!” She flounced back onto her bench, her breasts bouncing and wobbling as she did so. You groan and fold over, doubled-in-two by the sudden surge of pleasure in your cock, afraid that you were going to go over the edge and explode in your pants right there. You manage to pull yourself back from a huge orgasm, feeling the precum leaking out of your cock as you slowly return to a sitting position, every fractional rub of the fabric of your trunks sending another tremor through you. Kristy has a concerned look on her face: “Are you okay?” She asks.
“Y-yeah...” You manage, “Just... A little seasick, I think...”
“Seasick!” She laughs, but only teasingly, “We haven’t even left the pier yet!”
“I know, it’s terrible. I just need to...” You reach into your backpack, and mime taking something, making a show of swallowing. “There, I’ll be okay now.”
“Good, I’d hate for our little outing to be over before it really began...” She smiled coyly at him, “Let’s get going.”
As you busied yourself preparing the boat to cast-off, you used the distraction to calm yourself down. It works... At least, it was working, until Kristy leaned back in her part of the boat and began applying suncream to her neck and chest. You feel your erection start to swell again. With a final kick you push the boat away, and start off down the river at a nice, gentle pace. The outboard is old, and your uncle has warned you time and again against pushing it. You exchange smalltalk for a while: siblings, sports, gossip from work. The whole time you struggle - and fail - to keep your eyes off Kristy’s breasts as they gently bounce and jiggle with the movements of the boat. After a while you lapse into an almost comfortable silence.
“Hey,” Kristy says after a few minutes, and you jump, snapped out of your breast-induced reverie; had she finally noticed... “How fast can this thing go?”
“Uh, pretty fast, I think...” You struggle to remember, shifting in your seat to try and relieve the pressure on your stiff cock. It was trapped up against the waistband, every movement running the head of your penis against the ribbed fabric of the swimwear, sending waves of ecstasy through your groin.
“Let’s take it up a notch. I want to feel the wind...” She grins at you and clicks her fingers, the motion causing her breasts to jiggle even harder. You swallow and nod, your cock in agony. As you increase the throttle and the boat speeds up, it starts to hit the small waves harder, with each hit your cock is forced harder against the fabric of your shorts, and Kristy’s breasts jump a little more in her small red bikini.
You push the throttle a little harder. Kristy has thrown her head back, letting the breeze wash through her scalp, her chest pushed out towards you. Your cock is pressed even harder, the rubbing has become semi-regular, and you feel it start to twitch even between the waves. Her glorious boobs are in a constant state of motion, bouncing in her top, jiggling seductively... Luckily this part of the river is clear, because you can’t take your eyes off them.
The faster you go, the more her breasts leap in her bikini top, and the better your cock feels. You push the throttle harder. It feels so good. She’s so sexy. You push it harder, go faster, feeling better, her tits bouncing more and more and more...
Then it all happens at once. You hit an especially hard wave, and the force causes the boat to leap out of the water for a moment... The millisecond of freefall is enough to cause Kristy’s bikini to fall away, exposing her boobs to the wind. That second burns into your consciousness, every detail perfectly clear, bypassing your brain and going straight to your cock: The soft contours of her breasts, the pert pink nipples hardened by the cold wind and the excitement of the ride, everything looking so good, so fuckable...
Then the boat hits the water again, and your cock is forced into a few seconds of constant contact with your ribbed waistband. The pleasure crests and almost pushes you over the edge. You clench your thighs and try to hold it, and succeed for a second, for a second... Kristy claps her hands over her breasts, and tries to fondle them back into her top, her hands having trouble finding traction on the soft, supple skin made slick by water and suncream. You’re clenching everything, you can’t... you won’t...
“Shiiiiiiii-...”
You lose it. Cum shoots out of your cock and fills your trunks, soaking through them in seconds. The force of the orgasm both doubles you over and forces your legs out, and you can’t stop your hips from thrusting as you dry-hump your own shorts, your aching cock hungry for more sensation. Trying to delay it only heightened the sensation, and you’re cumming more than you can ever remember. You grab your dick through your shorts to try and stop it, only to see a creamy glob of your own semen push its way through the crotch of your trunks, immediately followed by another as your dick keeps pumping your pants full of cum. You glance at Kristy, her tits once again hidden in her top, hoping, somehow, that she hasn’t noticed... But her face is aghast.
Then the old outboard cuts out, stranding the two of you in the middle of the river. You turn and try to kick it over again, your face is burning, your cock rapidly shrinking in your sticky trunks, too ashamed to face Kristy, but the outboard has had it... It won’t turn over... Eventually, you turn to face her, humiliatingly aware of the massive stain on the front of your shorts. You’ll have to swim for shore. This date is definitely over...
“So...” She smiles, her tone caught somewhere between teasing and mocking, “Does everything you own give out prematurely, or..?”
