Your GF Hates When You Wear Clothes Ch. 02

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...

Reluctantly, he pulled his hands aside, causing his morning wood to spring forth and bouncily settle in front of him. The sight of it caused Eleanor to audibly gasp in pleasure.

"There's my favorite toy!" she gushed, the hand she had on John's head moving to give it a grab. He jumped in surprise but then melted into her touch as she held the head of his cock in her fist, thumb on top rubbing the tip of his mushroom. The hand on his back lowered to his butt, giving his cheek a squeeze. "Mmm... So nice havin' this beautiful willy in my hand again. Feast for the eyes, too! Welp, deals a deal, cowboy!"

She stood to her full height, reaching for the bottom hem of her tank top. With an upward pull, her massive tits fell out and settle onto her chest like pendulous beanbags. She pulled the garment off, depositing it into the rear basket of her commuter bike behind her. Topless once again, she kneeled in front of John, grinning and unashamed of her public exposure.

"Still like 'em, cowboy?" she asked, a cheeky smile on her freckled face.

John just nodded, the fact his hard dick was still fully exposed in the suburban air completely leaving his mind at the sight of Eleanor's massive funbags.

The southern belle giggled, ripples going through her fatty titflesh. "I love that reaction! Finally, a man who recognizes the quality a these county fair blue ribbon watermelons!" She lifted her pillow assets in both hands, presenting them. "Wanna touch 'em, cowboy? Oh, please touch 'em!"

She didn't let him respond. Grabbing John's hand, she placed it on her soft, warm titflesh. His fingers sunk deeply into the mass of it, the huge breast downright dwarfing his dainty hand and lithe fingers. If there were ever an eighth modern wonder of the world, Eleanor's tits would be a top contender!

"Mmmm, that feels good, having your hand on my boob, cowboy," she cooed, her freckled cheeks tinted pink. "Hey, cowboy. I got'n offer for ya!"

Said 'cowboy' cocked an elegant brow at her, listening to her moan as he gave her tit a squeeze. "Yeah?"

"I'll pick y'all up at two PM for the movie. If'n ya stay naked from now until I come pick ya up, I'll give y'all unlimited boob access for the date!" she offered, a mischievous grin on her pretty face.

He couldn't help but frown at that. "Unlimited boob access?"

She nodded. "Yup yup! Anytime y'all want, ya can touch n' rub my boobies or make me take my top off! But only if ya stay skyclad from now 'til I pick ya up at two!"

Hmmm... eleven AM to two PM. He'd have to refrain from getting dressed for three hours and he'd get unlimited prior consent to play with Eleanor's tits, clothed or bare, during their first date.

"How will you know I'll be naked all that time, though?" he asked, skeptical.

"I trust y'all!" she said, a big smile on her face despite the blush from John's hand squeezing her sensitive tit.

Three hours of nudity for unlimited boob access? Well shit, John knew a good deal when he saw it. Maintaining composure, he sighed and rolled his eyes, hands still playing with Eleanor's massive tits. "Fine. It's a deal."

The buxom blonde let out an ear-piercing squeal of delight. She scooped John's naked body up in her arms, holding him to her huge bare tits and showering his head and face with kisses. "That's my cowboy!" she gushed between kisses. He could feel his hard dick against her skirt, the fabric rubbing along his glans and upper shaft and causing an involuntary shudder.

When she was done kissing and titty-smothering him, she deposited John back on the sidewalk, causing him to stumble a bit as his bare feet landed on the concrete and struggled for balance. His hard cock swung and bobbed with his movements, drawing Eleanor's sparkling blue eyes.

She gave John's penis one last pat, as if she were saying goodbye to a domesticated animal, before climbing onto her bicycle. Still topless, he noticed. He weren't sure if it was deliberate or if the slightly scatterbrained girl just forgot. She put her helmet on, but still didn't seem to notice her own toplessness. "See y'all in three hours, cowboy!" Kicking her kickstand away, Eleanor blew him a kiss and rode her bike down the street. Suddenly acutely aware of his public suburban nudity, John hastily covered his hard cock with his hands and scurried back into his house, locking the door behind him.

It was surprisingly easy to just hang around his house casually naked. It actually made him think that those home nudists were onto something. John did some housework, studied a bit, played some games, all completely bare-ass naked and with his below-average dick transitioning in and out of hard to semi-hard throughout the activities, only going flaccid for brief moments at a time. It actually surprised him how much hanging around his home in the buff would stimulate his erections. He spent quite a bit of time lying on his stomach on the sofa as he played on his phone or Switch, just to enjoy his hard cock wedged between his stomach and the couch cushion.

About an hour in, he heard his phone go off with a text message. A glance showed it was from Eleanor! He opened it, curious if it was about their date. Instead, his jaw dropped.

She'd sent him a selfie!

Eleanor was standing completely topless in what looked to be her front yard, the street visible behind her. She'd also removed her glasses but due to the photo cutting off at her midriff, he didn't know the full extent of her bareness. Still, the illusion of total nudity created by the the way the selfie was taken was enough to cause John's cock to expand to an absolutely raging, rock-hard boner. It took several moments before he snapped out of his sexual stupor to actually read the text. He tried to ignore the line of pre-cum flowing down his shaft and onto the balls and sofa cushion between his legs.

<"I road toples all the way hom 4 ya cowboi">

John could only respond with a thumbs up emoji, too stunned to formulate a snarky or more intelligent response to his surprisingly sexually forward girlfriend.

An hour later and he realized he'd officially spent two hours totally naked and drifting in and out of turgidity. It was an hour before Eleanor would be here for their date, but John was playing some Dark Souls until that time. It was actually kind of amusing, playing such a skill-intensive game with a bobbing erection between his legs. As much as John didn't want to admit it... he could get used to this. Having his balls and hard cock swinging free around the house was surprisingly freeing and he couldn't say he hated when it rubbed up against things he walked by. Hell, even the things he sat on felt good against his bare bubbly booty.

Just then, as if on clockwork with the top of the hour, the doorbell rang. He double-checked the clock just in case, but it was an hour until Eleanor would arrive for their first date. Maybe she came early just to enjoy some time with him before the movie? Or she came an hour early to make sure he hadn't gotten dressed to cheat their nude-for-tit deal. John set his controller down on the coffee table and hopped off the sofa, padding barefoot out of the living room and to the foyer. His erect member bobbed and his bare balls swung in front of him as he went to the front door, swinging it open in the hopes of surprising Eleanor.

...And seeing the opposite of Eleanor instead.

It was Sasha Dae-hyun, a girl he actually knew from art class back in high school! She only lived a block away, though he never considered her a friend, just an acquaintance. She worked as a part-time courier for a local parcel center and she'd delivered packages to his house before though, so she certainly knew him!

Whereas Eleanor was tall, curvy, buxom, slightly tanned, freckled, blonde, blue-eyed, and vivaciously outgoing, Sasha was everything the southern bell wasn't. She was only a bit taller than John, with clear skin so pale it was like she didn't get any sun. Her jet black hair hung in her face unevenly while her grey eyes had constant bags under them. She was petite in every sense of the word and had a gloomy aura every time John saw her. Despite the warmth of the end of the school year and approaching summer, she was dressed in a thick hooded sweatshirt and sweatpants, both black and slightly moist with sweat. Her ever-present black choker was there as her signature accessory, which clashed with the bright red uniform hat for her place of work. Her bicycle was probably parked just at the sidewalk.

As the sight of John's hard member and nude body, Sasha let out a shriek, raising the package she was holding up to shield her face. He simply replied with a "Shit!" and ducked away out of the doorframe, hands shooting to his exposed penis.

"Wait!"

That was the last word he expected to hear, but the suddenness of it caused John to reflexively halt to a stop, hard dick wagging a bit before he hastily cupped his insufficient hands over it. Despite his faulter, he was quick to launch into an explanation.

"I'm not some kinda flasher! I was just hanging around after a shower since I was going out soon and figured I'd get dressed when-"

"No, please!" Those words confused him. Sasha lowered the package, her pale face bright red as she looked at John's hand-protected crotch with her head turned to the side. "U-Um... Y-You don't have t-to hide. I-I-I... I like it."

He cocked an eyebrow at her. "You like what?"

She raised the package again, letting out a little whimper. "I-I-I mean, I've never seen a naked boy before! I-I'm... I'm glad it was you! A-And I think... I think I like what I s-ohhhh, it's so ha-I mean, this is so hard! Words are hard!" the meek, gloomy girl cried.

...Well, this was a development. He'd totally forgotten that he ordered a blu-ray from Amazon the other day and it was scheduled to arrive around this time. At least Sasha wasn't mad and going to call the police, he supposed?

John raised his head skyward (while skyclad) and let out a groan. "Look, let's just forget this ever happened. I'm gonna go get dressed and-"

"N-No!"

Her sudden objection again gave him pause. She had the package in front of her chest, looking at the naked young man with a desperate expression. Her sneaker-clad feet fidgeted nervously on his front step.

"Um... Uh, c-can I... Can I see it? Up close?"

"It? You mean my dick?" he asked.

Sasha's blush deepened at the word. She clenched her lips shut and just shakily nodded, too nervous to voice her newfound desires.

Well, Ellie wasn't technically his girlfriend right now, right? They'd yet to have their first date. But it still felt weird, having a girl he barely knew, but still knew enough to recognize and name, see his penis just an hour before a date with another girl.

"Yeah, no. Lemme just-"

"Please?!" she cried, her arms trembling. She looked close to breaking out into tears. "I've never seen a boy's p-penis before now! I-I-I want to get a better look! Please? I-I-I'll let you see my... my... my... my pussy! Y-You can see my pussy! I-I'll even disrobe before you uncover so you know I'm not bluffing! Just..." The meek girl looked down at the sidewalk. Shit, she was like a wounded puppy. "I'm not sure if I'll ever get a chance to see one again outside of hentai after this... Please? I promise, I won't tell anyone... No one would believe me, anyway..."

Well crap. She was so pitiful... It was really tugging at John's heartstrings. Should he pity this shy virgin? Maybe Ellie would understand...

"Fine." John moved his hands, only to find Sasha was already dropping trou. Her sweatpants and little black cotton panties fell to the doorstep and she lifted her hoodie up so that John could get a clear view of her completely shaven little white pussy. That took the young man aback at first, especially when the site of a bit of pink caused a mighty throb to his member. This didn't go unnoticed by Sasha, who despite her neves, opened one eye just in time to see a string of precum fling from John's penis. She gasped and one sentence emerged from her thin lips, barely a whisper as the sight of John's penile spasm was burned into her mind.

"Did I cause that..?"

Panicking now, Sasha shoved the package into John's hands, nearly pushing him back. Turning to run, she tripped and fell face-first onto John's front walkway, giving him a clear view of her surprisingly cute, milky white bubble butt and pleasingly curved hips, the upward motion of her legs causing her black sandals to fly off. After a brief moment to contemplate every mistake that led her to this moment, Sasha scrambled to her feet, abandoning her pants and panties and running barefoot and bottomless out of John's yard and down to the corner where she'd parked her bike.

...Well, that was bizarre. Sighing, John closed his front door, idly worried about Sasha's bottomless trip down to the corner. She'd come back for her clothes when she realized, right?

-o-

Ellie rode her bike down the street an hour before her first date with John, eager to surprise him early. She knew he'd be naked like he promised, so spending a bit of extra time with her new naked boyfriend was a definite intentional bonus.