It was a Friday night when Ellie had first met John during the big game. Upon slipping under the gate and heading inside, he ran to his room and collapsed on the bed. He was tired and it was late, so he didn't even bother getting dressed. he needed his sleep.
His dreams were... interesting. Naked in public, with a tall, buxom blonde rubbing his hard cock in front of the crowd, holding his clothes up in a game of keep-away, and kissing him all over. Like most dreams, it seemed like he was viewing everything through a mental haze and the faces were all indistinct. Still, he couldn't deny that it was erotic...
Until he woke up to a hot, wet mess forming between him and his comforter. John shot his head up, finding that, yes, for the first time since he was barely-pubescent, he'd been woken up by a wet dream!
"Ewwww!" he growled, standing up and padding naked to the bathroom down the hall to clean up.
He wiped what cum he could off his stomach and dick, then went to grab his comforter and toss it into the laundry shoot in his room. It was at that moment that he heard repeated tapping on the window. Investigating, he was 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.
He opened the window, screen included, and stuck his head out. "Eleanor?"
"Hi, cowboy!" she called up with that recognizable southern twang.
"What time is it?" he groaned.
"Eleven A.M.! Sorry, I know it's early for a Saturday, but I realized that I forgot to give ya 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 he 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. Of course, she also wore her usual glasses. John had to admit, while the way they 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 him, for some reason! He never really had many prospects due to not actively looking for a girlfriend or boyfriend. He was in no hurry, after all. Not with college courses. Still, he kinda owed the curvy southern belle for saving him from that two-faced bitch... And jacking him off with her tits. Hey, even if he didn't owe her, he could definitely take Eleanor up on this date and see if it led anywhere good.
...Wait, eleven? He'd been asleep over twelve hours! John groaned, rubbing at his forehead. He was still half-asleep. As a result, he didn't realize that not only was he still stark naked but he was 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 him.
"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," he called down to the buxom blonde, making no effort to hide the fact that he staring right at her deep cleavage. To be fair, she was making no effort to hide the fact she was staring at his bare chest and hard cock, but... he sure as hell didn't know that!
"Sounds good to me, darlin'!" she called up. "How about... Oh, how about the pool?" Eleanor called up.
Seeing Eleanor in a bikini on the first date? "No way. Too much," he called down. "Let's start small. Dinner and a movie."
"Awww..." Eleanor pouted, her plan of seeing John in a tight speedo or loose trunks foiled. "Sure thing, darlin'! There's a new superhero flick down at the ol' Silver Screen Sinema! It's at 3pm n' we could hit up this nice burger shop nearby!"
Sounded simple enough. He shrugged. "Sure. Lemme get you my number."
John closed his window and headed for his desk, grabbing a sticky note and writing his number down. With surprising lack of personal and situational awareness, he headed out of his room still naked and with his morning wood bobbing in front of him, mind on his date with this odd country girl. He reached the front door and opened it, perplexed at the delight Eleanor had at the sight of him. His boner still bouncing in the late morning air, he padded barefoot down the short walkway from his front step to where Eleanor was standing on the sidewalk.
John held up the sticky note for her to take."There ya go, that's my number," he said. But the buxom blonde didn't take it. She had a mischievous grin on her face as she looked down at him, a lustful mist in her blue eyes even through her glasses... and it was at that moment John felt the breeze between his legs and morning sun on his bare skin.
"Shit!" he exclaimed, thrusting his hands over his rigid cock. He was below-average in dick size, but his small hands definitely weren't adequate enough to completely cover the shaft, let alone the balls hanging below it!
Eleanor giggled at his embarrassment, kneeling down to ruffle his hair with one hand and rub his bare back with the other. "Awww, how sweet a' y'all to come out here dressed in your best for little ol' me!" she teased.
"Best nothin'! I was sleeping when you got here and forgot I was naked!" John growled up at her. With her kneeling in front of him like this, he had a great view down her braless cleavage, which certainly wasn't helping his erection! Neither was her touching him, for that matter!
She waggled her eyebrows. "Y'all sleep in the buff, huh?"
"No! I mean, not usually, just... Grah!" He groaned, stamping his feet in frustration.
"Awww, don't be like that, darlin'! There ain't no one around! It's just me here on this street, and I already seen y'all naked! Cute little cowboy like you ain't got nothin' to be ashamed of! In fact, coverin' up that pretty skin should be a crime! C'mon, let's get your hands off that beautiful thing, lemme see it again!"
"What? No way!" John barked, despite how much his body un-tensed at Eleanor's gentle rubs on his back and hair.
"Awww, c'mon... Please? I been thinkin' 'bout it ever since last night! Can't get your beautiful penis outta my brain-pan!" she pleaded, pouting complete with lower lip extended. "I'll let y'all see my boobs again!"
Eleanor was so forceful... But, well. He had more to gain out of this than lose. Yeah, no one was around the suburbs at that time. He could just run back inside after she had left. She'd already seen his cock and even given it a titfuck last night, it was old news to her. He'd get to see her tits again. And it would certainly make the girl he was going on a date with later today happy...
