Your GF Hates When You Wear Clothes

It was nearing the end of his senior year of high school, several months after he'd turned 18, that John first met Ellie. Looking back, it hardly seems real. The whirlwind of events that led to them dating. Despite how surreal it feels in retrospect though, he remembers it like it was yesterday.

There was this cute girl, Shirley, who had just broken up with Nathan. Nathan, or "Nuke" as he was often called, was the captain of the football team. Much to the surprise of everyone, rather than a hot cheerleader, Nuke had asked out Shirley, the school's frizzy-haired, homely nerd. The shallower of the school thought it was doomed to failure, and just three days before the big game, she dumped him.

...or so everyone thought. In reality, Nuke had dumped Shirley. And John Bennett found out why when Shirley invited him to meet her in the locker room. They had a few classes together so he thought she wanted someone safe to talk about Nuke with. He didn't have anything better to do that night, so he went to meet her.

Shirley waved at him from inside the locker room as he entered, but he was jumped by members of the second string the moment he entered. Being a short, scrawny guy, the beefy football players were easily able to restrain him by the arms.

"What the fuck?!" John exclaimed.

Shirley gave an innocent wave. "It's the last big game of our senior year. I figured I'd make it memorable."

"What? How?!"

He got his answer. The big guy on the right lifted his shirt up over his head, trapping his arms. John kicked and growled while the other second stringer repositioned himself to get his sandals and shorts off. They slipped down his legs along with his underwear, then with a hearty yank and forceful untangling of his arms, John was stark naked!

His hands cupped his penis. It wasn't small, but... Well, it was below-average and only looked medium-size because he was such a small guy. So yeah, he wasn't exactly happy with others seeing it thanks to one-too-many teasings as a child. Brow furrowing in anger, his eyes flicked to where one of the second stringers shoved his clothes in a locker and locked it up while Shirley studied his naked body from behind her round, geeky glasses with a perfectly practiced innocent smile.

"I figured a streaker would spice up our last game of the year."

"Why me?!"

She shrugged. "You're small, weak, and cute. I just thought you'd be an easy target."

Wow... what a two-faced bitch! One of the second string gave John a pat on his bare, bubbly butt. "Best get a move on!" he said.

Fuck! No way was he streaking the game! But he wasn't sticking around and getting some ultimatum from asking for his clothes back! He'd take his chances outside! Turning on his heel, John ran, pounding barefoot out of the locker rooms and into the school hallways. With the cover of night and the big game going on, the halls were empty, but he knew he could run into anyone! His hands tightly hid his manhood as he dashed through the halls, trying to think of what he could do to cover himself. He was absolutely pissed, and when he was this pissed...

"Sniff! Hic!"

Dammit... Now here came the tears. A bit desperate at how pitiful he looked, he redoubled his mad dash down the hallway, turning the corner...

And smacking right into something soft and warm that blocked out his vision.

"Whoa! Hey, little guy! What are y'all..."

John looked up, realizing he was in the bosom of Eleanor Fairbreast, generally considered the nicest and bustiest girl in school. She was a senior like him, but he never had any classes with her. John saw her around, but he never felt any interest in talking to her. She was sexy and he couldn't deny liking her mammoth tits, but that was the limit of his thoughts on her.

The Southern Bell was wearing a simple white camisole, pink pleated miniskirt, and feminine light blue sandals. Her long blonde hair was done up in a high, perky ponytail with a big light blue ribbon. Pretty blue eyes looked down at him through thick-framed horn-rimmed glasses perched on a freckle-covered little nose above her full pink lips. Her camisole was thin and low-cut enough that John's chin was against bare breastflesh.

The impact had caused one of the straps of her top to fall off her shoulder and she didn't seem to notice because of the look she was giving him... The collision also resulted in Eleanor reflexively wrapping her arms around him. This combined with the hand on each bare bubble buck cheek meant it only took her a mere moment to figure things out.

There was a fascinated look in her eyes as she realized the boy in her arms was naked... Her pale, freckled cheeks were flushed pink as her fingers gave the dusky skin of John's bubble butt a subconscious squeeze. Being in the cleavage of such a busty blonde, he also felt his cock give a lurch...

"He ran this way, Shirley!"

"Looks like he needs another push!"

Uh oh... Shirley and her goons had followed him! Eleanor looked at John's face, then down the hall, her mind hard at work analyzing what was going on based on the clues. But as the footsteps got closer, protective instincts took over. Eleanor looked both ways before she hefted John's nude body into her arms, holding him against her massive breasts as she ran for the nearest bathroom.

The girl ducked inside the girls' room and, for good measure, headed into a stall and sat on the toilet. The busty blonde pulled her legs up into a pretzel position, placing John's naked butt into her lap. Despite being a bit dazed at how she so easily manhandled him there, John still had enough self-awareness to shoot his hands into his lap to cover his dick. As if eager for security (giving or receiving), Eleanor wrapped her arms around his flat, androgynous chest, hugging him close to her softness. It was an oddly secure feeling, like he could feel safe in her arms.

Neither of them made a sound as they heard stomping in the hallway outside. It got louder, then faded as the two-faced geek and her second string lackeys passed the bathroom by. John couldn't deny that his heart was pounding in his chest. He couldn't believe this girl he didn't even know and barely acknowledged the existence of just rescued him!

"Uh... thanks..." he whispered. He turned to look up at the girl he was in the lap of, surprised at how flushed her face was and how heavy her breathing was. Despite how strained and warm she looked, she smiled, her arms giving John a squeeze like he was a teddy bear or body pillow.

"Dunno what happened, but... Just happy ya'll are safe, darlin'!" she chirped, grinning despite sounding out-of-breath.

"Uh... yeah. Why'd you save me?" he asked. John had always been something of a loner... He wasn't some misanthrope, but it still felt odd to have some girl he didn't know rescue him like that.

She shrugged. "Oh, ya know... Just the right and proper thing to do, right? Cute little darlin' like y'all, runnin' scared, in the school..." she swallowed hard. "Completely naked." A shudder ran through her body.

The thicc blonde sat up, scooping John into her arms and stepping out of the stall. She placed him on the counter, between two of the sinks. His shapely chocolate legs dangled off the end of the counter, too short to reach the floor, and he hastily cupped his hands to his bare penis. Despite the manhandling, he only felt mild trepidation.

He watched Eleanor curiously as she grabbed a paper towel from the dispenser and wet it in the sink. She returned to him, using the warm and damp towel to wipe some of the tears from his cheeks. It was a really tender and nurturing gesture... one he wasn't used to as a latchkey kid.

"So, tell me... How'd y'all wind up naked and chased by them folk?" she asked. She was smiling sympathetically at him, but he couldn't help but notice the erect nipples tenting her thin, white camisole.

"Oh, uh..." he was momentarily distracted. She was bending forward, wiping at his cheeks. In addition to the deep cleavage she was showing him, her pendulous tits were swinging and wiggling, making it all the more painfully clear she was braless under her camisole. "Shirley wanted me to streak the big game... She thought I was an easy target."

"Easy target? Aww, darlin'..." Eleanor tossed the wet paper towel into the trash, then used a dry one to dry his cheeks. "I think you're a cutie! You're small, but lookit that skin! So smooth and chocolatey..." She gave an inhale. "And y'all smell good, too!"

She tossed the towel she used to dry his cheeks over in the trash. Smiling, she spread her arms and stepped forward. John braced himself, but instantly relaxed when she wrapped him in a big, warm hug, pushing his face into her tits. It was odd, sitting on a counter while a girl his age but twice his size hugged him, let alone naked like this!

"Oh~ Awww, you're blushin'! Ya'll don't need to be shy, sweetheart!" She giggled. "Your hair is so nice! Do them dreadlocks yourself? Mmmm..." Her hand ran down his bare back., causing a sexual shudder to run through his body. God, what was this woman doing to his libido? "Such soft n' supple skin... Flawless, no blemishes or scars... Aw, darlin', you're such a beautiful angel! Mm, such a cute lil' thing!"

"Uh... Thanks?" he mumbled from within Eleanor's cleavage. He jumped when her hands found his bare bum on the counter, giving his butt cheek a little pinch.

"Such a sweet lil' candy ass... Darlin', how'd ya get such a bubble butt?" She inhaled his hair, another shudder going through his body. He wasn't sure if he felt like a rabbit being tasted by a predator or a bunny being cared for by a mother cub. One of her hands found his leg, running along his shapely thigh. "Darlin', y'all shouldn't be so embarrassed to be buck-ass... Such a..." She moaned, rocking him a bit in his marshmallow prison. "Such a beautiful darlin'... Downright shame to hide such a gorgeous body under yucky, icky clothes..."

His penis was hard. He wasn't used to girls showering him with praise for his appearance! To his embarrassment, John's cock rose and hit the underside of Eleanor's breasts.

She noticed. "Oh! Oh, goodness! Are y'all startin' to get stiff for me already? Aw, you are eager, huh baby?"

Pulling away just a bit, Eleanor looked down. Her freckled face lit up at what she found, blue eyes sparkling with delight at the sight of his erect cock poking out from his lap.

"Whoa... Darlin', your penis is so cute! This's big for a cowboy your size! Is this for me?"

He blushed, hands trying to cover it. "I-It's not that big... I'm below average, it's just that the rest of me is small..."

She kneeled down, mouth level with John's boner as she giggled and gently guided his hands away from his hard prick, strong yet feminine hands surprisingly forceful despite her gentleness. He wasn't sure why he let her, but John felt his face heat up as his stiff rod sprang up and bobbed in front of Eleanor's face.

"It's perfect, darlin'. There's plenty for me to work with here," she cooed as she placed a hand on each of his knees. Shit, he could feel her breath on it. It was making it throb. The curvy girl reached her hand up, fingers reverently teasing at the side of his shaft. The young man felt a shudder go through him.

"Here, let me help y'all out a little... I'm just gonna lightly tickle your perfect little cock... There we go... Just like that... tracin' ya... squeezin' ya, ever so gently with soft, warm hands... pressin' and rubbin' my forefinger up against your sensitive tip..."

Oh god, he couldn't remember the last time he was this turned on! His cock was at its full size, beating in time with his heartbeat and oozing precum down its length.

"Mmm... This looks so hard... Must be uncomfortable... So, can Ellie take care a this for ya?"

Wait, was she asking to relieve him? Uh, brain shutting down... Unable to fully process this situation, he just dumbly nodded, his mouth hanging open and his face flushed.

The thicc blonde giggled, reaching up to ruffle the hair on the top of his head. "Awww, good boy! That's a good boy! No need to blush, darlin'! Sexy stud like y'all should be naked 24/7! Hee hee!"

Her blue, glasses-covered eyes focused on his hard, throbbing cock sticking out from between his thighs, licking her plump pink lips at the sight of it. Her hand, which hadn't actually left his dick during the headpatting her other hand did, started to gently rub and massage his length. Her nails were long and he gave a jump when she used them to softly scratch along his length. He was surprised by how good it felt!

"There we go, sweetheart. That's it. Ohhh~, baby, that feels nice, don't it? And ya may be little, but your balls are so full~" Eleanor cooed in a teasing lilt. She cupped one of his brown balls, gently jiggling it a bit with a naughty grin on her face. "Lemme give 'em a nice, long squeeze. Ohhh~... There we go. Mmm..." She leaned in a bit, giving him another glorious view down her camisole. "Good boy~," she whispered, her voice surprisingly husky.

John couldn't believe this was happening... The bustiest girl in school, bigger than even the MILF-iest of the teachers, here in the girls' restroom with his naked as a jaybird ass on the counter and having his cock and balls teased and worshiped by her! He never thought this possible, never even thought to fantasize it! Despite how embarrassing it was to be appraised by such a gorgeous girl, even positively, John couldn't deny he'd never been this aroused before!

"Oh! You're leakin' so much pre-cum for me! You're spillin' and droolin' all over my fingers!" Eleanor gushed, sounding absolutely delighted. "You're gonna make a lotta yummy cummies, aren't ya my sweet little cowboy?" She giggled. "Mmmhmm~ Yes you are!"

His head swam with a fuzzy heat, the sheer amount of arousal clouding his higher reasoning. He was at the mercy of this buxom blonde. She had him by the balls in a sense both figurative and literal!

"I'm gonna make a slippery little ring with my forefinger and thumb now, okay? And I'm gonna wrap them tight around your stiff cock, right here at the base, and gently squeeze it allllll the way down... all the way down to your sensitive tip."

A series of shudders ran through his body. Involuntarily, he leaned forward.

"Oh, you're shakin'! It's okay baby, I've got you, I've got you. I'm just gonna stroke your back as I jerk this perfect, stiff penis. Oooh~, good boy... good boy!"

Her free hand rubbed his bare back, regularly dipping low enough to run a finger along his butt crack. Eleanor's thinly-covered breasts squished into his knees as her other hand continued to give him a steady handjob.

"Up and down... Up and down..." She cooed. John gave a strangled cry and lurched backwards, Eleanor's hand steadying him. "Ssh, ssh, sssshhh~ I've got ya... Ellie's got ya... Ya'll can trust me. Just leave it to Ellie, okay cowboy?"

Shivers ran through him. He was so hot with lust, he could barely think. Only Eleanor's southern twang kept him grounded enough to not have his mind go white.

"Does it feel nice, cowboy? Having your own personal handjob girl? A girl to take care of ya? A sexy girl to help y'all squirt out all those hot, yummy cummies...? Mmmn~" She leaned in, whispering as her boobs squished into his knees. "I'm gonna add a few more fingers now, okay sweetheart?"

What was originally just a ring of her thumb and index finger soon became a full handjob, along with an increased pace! John began to pant and moan.

"Mm-hmm... There we go. Good boy, good boy! Good boyyy~ Hump into my hand, baby! Hump into my hand. It's okay to whimper... Go right ahead n' moan for me if'n ya need to, don't be shy now! Mmmmn~ that's a good boy~" She patted him on the back.

Involuntarily, his hips were thrusting in time with the up and down motions of Eleanor's hand. His bubbly butt left the counter briefly each time, causing him to idly realize he was sitting in a small pool of his own pre-cum by now!

"Oh, you're such a precious little thing... Is this the first time you've ever gotten jacked off by a girl...?" He feverishly nodded. "Yeah? Awww~ Well you're doin' a wonderful job, sweetie! I'm very proud of ya."

All the time he passed Eleanor in the halls... And she had this side to her? Did she do this a lot, or was there something about him, specifically? The buxom blonde southern belle was acting so... forward!

"Mmm~ that's it... up and down... up... and down... squeezin' so tenderly around your sensitive little penis... Oh you're just so adorable! I can't help but wanna spoil ya, my little cowboy... Hmm... Do you wanna see my boobs? I know you've been lookin' at 'em this whole time. It's okay, look all ya want! Ya'll don't gotta be shy!"

He was so close to cumming! He could only give a strangled noise from the back of his throat and a nod of his head.

She let out one of her light, airy giggles in response. "Here, I'll let go of your penis, just for a minute, cowboy. Don't get cold or lonely... Just be a moment, darlin'."

Admittedly, he did feel a bit cold and alone when her hands left his back and angry purple erection. Without Eleanor's warm touch, he was reminded of just how naked he was. Though this thought only existed for the briefest of moments before he saw the buxom blonde reach under her breasts and give them a lift.

"Do ya like 'em, huh? See how my huge boobies are squished together in my tight little cami?" She giggled, an action that sent ripples through her huge tracts of land. The way she was lifting them up, it caused the straps of her camisole to slacken and fall off her shoulders and made it seem like she was offering her tits to him.

"Although... it don't exactly cover up much, do it, sweetheart? Just look at that cleavage... I love showin' em off, but I don't think just this is enough for y'all."

His breath died in his throat as, with a bit of struggle, Eleanor lifted the bottom hem of her camisole up. An involuntary, gurgled gasp sounded deep in John's throat when her huge white whales flopped free of their prison, swinging around before settling weightily on her chest. The busty blonde lifted the flimsy garment up and over her head, down her arms, and tossed it aside. She grinned at him, her freckled cheeks and pale cleavage flushed a bit pink as she held her now-bare tits up, giving them a jiggle.

"There. Ya wanna touch 'em, cowboy?"

John just nodded, though his arms were too frozen to move. They didn't need to.

Grabbing one of his hands, Eleanor dumped her massive tits into his bare lap, causing a jolt to go through John as soft, warm, pillow tit slapped onto his rock-hard member and naked thighs. The sheer volume of boob overflowed out of his lap, completely enveloping his pelvis. Eleanor placed the hand she'd been holding on her tit, giving clear consent of the highest level as she pressed his palm into the cloud-like oh my god it was like his small hand was getting lost in these melons!

As if this couldn't get any more arousingly surreal, Eleanor parted her own cleavage and fished around inside. More sexual jolts went through John as she extracted the tip of his hard cock to the opening of her cleavage, oozing precum down her heavenly valley.

"Oh, you liked that, didn't you, baby! Such a helpless boy~" She giggled. The way her tits wiggled like gelatin molds around his twitching cock... John thought he might cum any second! "Your cute penis is stickin' up all straight n' stiff!"

He was gasping for breath when she leaned in to whisper in his ear again.

"Now, you just sit back and relax, my naked little cowboy..." She placed a finger on his lip before he could strangle out a word. "Hush, now, little guy... Try not to move too much, hmmm~? Just relax, and enjoy, and I'll take your slippery cock between my boobies and... oooh~"

Ohhh~ was right! If John didn't know any better, he'd swear that Eleanor was getting as aroused from squeezing and grinding her tits around his cock as he was! Her face was flushed like she had heatstroke and her breath was coming out in pants and loud, sexual moans! John realized his hand was still palming the top of her breast. Weakly, both his hands found her nipples and, managing to muster up some agency, he gave her pink nubs a pinch.