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Chapter 3 by Cyberweasel89 Cyberweasel89

[Choose Story]

[Your First Date]

The big game that you met Eleanor at was Friday night and upon slipping under the gate and heading inside, you had sneaked to your room and collapsed on the bed. You were tired and it was late, so you didn't even bother getting dressed. You needed your sleep.

Your dreams were... interesting. Naked in public, with a tall, buxom blonde rubbing your hard cock in front of the crowd, holding your clothes up in a game of keep-away, and kissing you all over. Like most dreams, it seemed like you were viewing everything through a mental haze and the faces were all indistinct. Still, you couldn't deny that it was an erotic dream...

Until you woke up to a hot, wet mess forming between you and your comforter. You shot your head up, finding that, yes, for the first time since you were barely-pubescent, you'd been woken up by a wet dream!

"Ewwww!" you growled, standing up and padding naked to the bathroom down the hall to clean up.

You wiped what cum you could off your stomach and dick, then went to grab your comforter and toss it into the laundry shoot in your room. It was at that moment that you heard repeated tapping on the window. Confused, you went to the window sill, surprised to see Eleanor down there, pebbles in hand and her familiar overly-accessorized bicycle parked on the sidewalk in front, cargo trailer and all.

You opened the window, screen included, and stuck your head out. "Eleanor?"

"Hi, cowboy!" she called up with that recognizable southern twang.

"What time is it?" you groaned.

"Eleven A.M.! Sorry, I know it's early for a Saturday, but I realized that I forgot to give ya'll my number! Figured I'd come by so we can plan our first date!"

She was wearing a pleated pink miniskirt, a white tank top that you could plainly see down from up here (no bra), and a pair of sky blue and white sneakers with white socks, likely because it's safer for cycling, and her usual glasses. You had to admit, while the way you had met was odd, she was definitely a catch... Curves for days, biggest tits in school, tall, glasses, and a blue-eyed blonde with freckles. And she was certainly into you, for some reason! You didn't exactly have many options, but neither were you really in a hurry to get a girlfriend or boyfriend. Still, you kinda owed her for saving you from that two-faced bitch... And jacking you off with her tits. And hey, even if you didn't owe her, you could definitely take Eleanor up on this date and see if it led anywhere good.

...Wait, eleven? You'd been asleep over twelve hours! You groaned, rubbing at your forehead. You were still half-asleep, and as a result, you didn't realize that, not only were you still stark naked, but you were leaning out of the window with a big black hard-on plainly visible over the window sill. In retrospect, that was probably why Eleanor looked so happy to see you.

"Look, I need some time to get ready. Just... name a time and place and you can come pick me up, okay? I'll give you my number so you can let me know when you show up. If the date goes well, I'll give you my Discord contact," you called down to the buxom blonde southern belle, making no effort to hide the fact that you were staring right at her deep cleavage. To be fair, she was making no effort to hide the fact she was staring at your bare chest and hard cock, but... you sure as hell didn't know that!

"Sounds good to me, darlin'!" she called up. "How about..."

Where did Eleanor want to go for your first date?

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