Girl Wedgie Story

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Girl Wedgie Story
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"You actually did that?" Hannah Hunter asked incredulously, staring up from her burrito bowl. Ashley Rose nodded, chuckling through a sip of her iced tea. "I mean, I deleted the picture eventually and made up with the guy, but that image is burned into my brain, clear as day. I was a mean girl back in the day." "No kidding," Hannah remarked, her gaze drifing away from the table as if trying to visualize it for herself. "An atomic wedgie. I thought that was just something they made up for 80's high school movies." "Nope," Ashley confirmed. "We've got fifteen minutes, by the way," she added, returning her attention to the last of her fajitas. "Does boys' underwear even stretch that much?" continued Hannah. "Does *anyone's* underwear stretch that much?" Ashley swallowed her bite of fajita. "You tell me," she answered, wiping her mouth with her napkin. "Right, right," Hannah answered, apparently having already forgotten the incident that led them to this conversation in the first place.
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Your friend Damion stands up and walks away from the table, picking up his open beer and taking a swig to polish off whatever trace amounts remained at the bottom of the can.
“C’moooooon!” begs Grace, attempting to be cute. “Just one more round. It’ll be fuuuuun!”
“Nope,” he reaffirms, pitching his empty can into the trash bag tied to a kitchen drawer handle, a cheap, nearly-full bag that was functioning as your recycling bin for the weekend. “It’s a wrap. I’m beat. This game is childish anyway.”
Grace huffs. “’Childish?’ What are you, a lame old geezer?”
Damion turns to you. “Can you do something about this? She’s your girl.”
“She’s not ‘his,’ Dame,” Ashley chimes in, putting down her Solo cup of water and leaning back in a chair next to Grace. “She’s her own person. And you know HE’S not gonna say anything, anyway.”
You jump in to defend yourself. “Hey, that’s not-“
“NO,” Grace says, raising her voice. “I AM his. And he DOES say stuff. He wears the pants in this relationship, don’t you baby?
“Yeah,” Damion says to you, raising his voice. “*Don’t* you, baaaaaby?”
“Do I get to talk now?” you ask, annoyed.
“I dunno pants boy, do ya?” Ashley cracks.
Grace snorts out a laugh, perhaps unaware that she was being teased as much as you were. “Pants boy! That’s too funny.”
At least one of you was having fun.
You had a few goals with your weekend getaway with your friends and your new girlfriend Grace Carpenter at a cabin outside town. One: get closer with Grace, the cute, red-headed girl you'd been dating for just about two months now.
Second: have a good time with your friends Damion, Elissa, Cal, and Ashley Rose. They all knew you were dating Grace, but this was the first time they’d be spending an extended period with her. You wanted them to like her…or at least not hate her.
And lastly…you wanted to get *closer* with Grace. Not long after the two of you started going out, you learned that Grace came from a very conservative family. You were her first “real” boyfriend, and she wanted to take things slow. Very slow. And you understood that…mostly. You liked Grace a lot and didn’t want to push her to do anything she wasn’t ready for, but at the same time, you were hoping to do something with her this weekend besides, say, making out in the back of a movie theater like a high-school sophomore. And your room was far enough away from everyone else’s that you thought you might get to enjoy a nice post-partying evening alone with her.
But the day wasn’t quite going to plan. Grace was a little younger than you and most of your friends, and her bubbly and somewhat innocent personality wasn’t jiving with your older and somewhat more cynical peer group. The only person close to Grace’s age was your close friend Ashley, a pretty Vietnamese girl with black hair and green eyes who was in your year of college but had graduated high school two years early. Though Ashley had agreed to “go easy on Grace” per your request, she was having a hard time containing her annoyance with your perky-to-a-fault girlfriend.
Then, after a long day of you trying to make your friends see what it was you saw in her, Grace decided she wanted to try a beer that night. A single beer, no more or less, to see “what the big freaking deal is.”
“Are…are you sure?” you’d asked. Having had your first beer late in your own freshman year, you were a little happy she was loosening up.
“I want to! C’mon, I know people do it all the time. Well, everyone but Ashley,” she added, laughing.
Ashley, already in a plain black T-shirt top and gray pajama bottoms, rolled her eyes from the kitchen, but turned and opened the fridge to reveal a half-drank case of light beer.
“All yours, kiddo,” she quipped, despite the two of them being about the same age.
Grace held fast to her one-beer rule. Unfortunately, one light beer was plenty for Grace, who spent the next hour or so excitedly telling everyone who would listen (and some who wouldn’t) about how the beer wasn’t affecting her at all. She then demanded the group play Truth or Dare, which received an audible groan out of Damion but a surprising defense from Ashley.
“C’mon guys,” she said, turning to you with a familiar grin on her face. “I think it’ll be fun, don’t you, friend?”
You were not thrilled about that look paired with those words.
You’d only gotten one fairly dull round in before Cal and Elissa bowed out. And now, with Damion departing, it was just you, Ashley and Grace. The night was not going according to plan, and you were ready to check out.
“Maybe we should wrap it up then,” you suggest. “It’s not gonna be any fun with just three of us.”
“Awwww, when did you get so lame?” Grace pouts.
Ashley, completely cool with watching you squirm despite being one of your closest friends, chimes in. “Yeah, Lame Pants Boy, what’s with you?”
Grace snorts again. “Lame Pants Boy! You’re so funny Ashley.”
“C’mon Pablo, just one more round, pleeeeaaaase,” Grace begs, calling you by the name you went by in the Spanish class the two of you met in. “I’m having fun! Don’t you want to have fun too?”
You sigh and decide to be a good sport. “Okay, whose turn is-“
“MIIIIINE!” Grace declares. “PABLO! Truth or dare?”
“Okay, truth! How many girlfriends did you have before me?”
You’re surprised to find yourself blushing at the question. What did you have to hide? Not much.
“J-just one,” you say. (Really, you didn’t have much to hide)
“Really? Wow.” Grace looks conflicted, as if both happy and disappointed you weren’t a serial dater.
“Way to go, Casanova,” Ashley snarks.
“Okay then Ashley, you asked for it. Truth or dare?”
“I dare you to pick anyone but me.”
“C’mon, pick me!” Grace jumps in. “Nobody asked me anything yet! Plus, I asked you something fun, now you’ve gotta ask me something fun.” She lowers her eyelids and reaches her head slightly across the table, a playful grin on her face. That look coupled with her flattering if simple nightwear (a snug white tank top and short, teal pajama shorts) made you swoon.
“Truth.” Her expression doesn’t change, her eyes locked with yours.
Somehow, you saw a faint light at the end of the “Get Past First Base with Grace” tunnel, either tonight or further down the line. But you already knew she never dated before you, so what kind of quest-
“What color underwear are you wearing?”
The question is out before your brain has a chance to remind you that it wasn’t just you and Grace playing.
Grace turns beet red. “What...color?”
“I’m sorry, I'm sorry, you don’t have to-“
“No no, it’s fine. I, uh…” Grace looks down as if about to pull the waistband of her teal pajama shorts out to check what she’d put on, then remembers. “Pink. For both."
“Aw, cute,” Ashley remarks. Grace smiles, as if wondering what she had been so embarrassed about.
“Hold on, Grace. After what he just asked you? You’ve gotta get him back for that.”
“You know what? You’re right Ashley. You!” Grace turns back to face you. “Truth or dare?”
You’re about to say “truth,” but Ashley interrupts.
“He picks ‘dare.’ We haven’t had any dares tonight and you owe him some payback.”
“Wait, no!”
“Yeah, you’re doing a dare!” concurs Grace, clearly enjoying the prospect of playfully getting you back. “I dare you to-“
“Wait,” Ashley stops her. “I have an idea.”
Ashley leans over and whispers into Grace’s ear. Grace listens intently, then furrows her brow.
Ashley repeats the whisper, then adds an audible “It’ll be fun.”
You were very aware of what Ashley's idea of "fun was." Your butt cheeks clench.
Your girlfriend turns back to you and gives you a devilish look.
"Am I holding them right?" Grace asks.
The three of you had moved just outside the cabin since, as Ashley so eloquently put it, "everyone's gonna get real pissed if we wake them up with all the shrieking he's about to do." Though it was quite dark outside, the light from the cabin gave Grace just enough visibility to place her right hand down the back of your dark gray sweatpants tentatively grasp the waistband of your white briefs. She'd giggled at the sight of them as she pulled them up just slightly over your sweats. You notice a bead of sweat form on your forehead as you stare out into the woods with Grace and Ashley behind you.
"Nah, you've gotta go two hands," says Ashley. "And not too far apart either. You want them in the middle, near his butt crack."
Grace giggles again at "butt crack." "Okay, I got it." She slides her right hand closer to the center of your back and places her left hand right next to it, shifting to a two-handed grab.
"Ready?" Grace asks. Before you can respond-
"YOWCH!"
An exuberant Grace jumps into the air, your tighty whities still in her grasp. Your entire body jolts up along with her, the quick but cutting pain of your own underwear being forced into your rear shocking your senses. Your butt cheeks flare in pain from the friction of the briefs rubbing against them as they're yanked into your crack.
"How was that?" Grace asks Ashley, excitedly.
"Eh, not bad. But you don't want to just yank them up once. You want to hold it as long as you can before you let go and pull again. Kinda like you're playing tug-of-war with his undies."
Grace yanks up again, this time holding your waistband aloft for several seconds. Though Grace was a fairly petite girl, she was plenty strong enough to stretch your waistband halfway up your back in just two pulls. Your groin was pinned against your body by the front of your briefs. You find yourself gasping for air, the two sharp yanks knocking the wind out of you.
"*Much* better," Ashley commends her over the sound of cotton fibers tearing and stretching beyond their usual limits. "The key with boys' briefs is to stretch them out as much as possible without ripping them entirely so you've got more material to work with. Wouldn't you agree, friend?"
"Are you done coaching her?" you wheeze, barely keeping your footing as Grace maintains the wedgie.
"Well, I owe it to her to teach her what I know," Ashley teases as she walks around your right side, a wide grin adorning her face as she looks at you.
"You're the absolute worst," you mumble.
"What's that?" Ashley asks loudly. "You bet Grace can't pull your underwear above your head? Wow, why would you say that? Sounds like a dare to me."
"Oh yeah?" Grace says in what you hope is still a playful taunt and not a vengeful one. Now fully committed, she gives your tighties yet another titanic pull upward, then another, then one more, her small, fair hands managing to pull your waistband up above your shoulders. Each pull is punctuated by an "OWCH" or something comporable from you. You feebly swat at the taut section of underwear protruding out of your sweatpants in a feeble attempt to get the wedgie out as Grace continues to pull.
"You know, I really never get to see this angle," Ashley says, observing you from the front and holding her fingers out in a rectangle shape as if framing a photo. "The sweaty red face, the crossed eyes, the waistband riding up the front, the shifting around trying to get free...it's a whole new perspective. I like it!"
From behind, though, you can hear Grace begin to breathe heavier as well, beginning to tire out. Ashley gives her a worried look.
"Are you okay, Gracey?" Ashley asks. If you weren't focused on your own underwear once again becoming your worst nightmare, you'd be happy that Ashley seemed to be genuinely concerned for Grace.
"Yeah Grace!" you add in a high-pitched voice. "Anytime you want to stop is fiiiiiiine with me, you know!"
"Y-yeah," Grace says between breathes. "Alright, I just..." She pauses. Though you can still feel her pulling tightly on your waistband, you sense her moving as if looking around. "Wait! I've got an idea." You groan, the chances of you finally escaping the brutal wedgie having seemingly disappeared.
Ashley chuckles. "Okay, well, don't overdo it, ok? We're just messing around here."
Grace takes two steps backwards and one step to her right, pulling you helplessly along by your waistband. Then-
Apparently, Grace's "idea" involved a picnic table just a few paces away from where you stood. With your expanded undies in tow, she'd stepped onto the bench of the table and gained a ton of newfound leverage. You feel your briefs lodge themselves even deeper into your rear. You stumble as you feel your feet get pulled slightly off the ground. Your body leans forward as almost your entire body weight is being held up by the strained part of your briefs that remains pinned to your groin. You feel like you might get split in two.
"Woo! I did it!" Grace exclaims, still firmly in control of your briefs as your tippy-toes try their hardest to remain grounded. "Whatcha think, Ashley?"
Ashley can't contain her laughter. She covers her mouth and begins slapping her leg in delight at the sight of a guy struggling to keep his footing while being hoisted into the air by his tighty whities, held aloft by a small, unassuming red-haired girl standing on a picnic table. Frankly, if you weren't the guy in question, you'd probably find the visual just as hilarious.
"That's so---ahahaha! That's so awesome," Ashley finally replies.
"Mmmmm, I dunno," Grace asks. Her voice has enough seriousness for you to briefly panic that she might just hold you like this the rest of the night. "What do you think Ashley?"
Her laughter finally quelled, Ashley leans forward and looks you directly in the eyes, with a satisfied smile bigger than any you've ever seen on her.
"Yeah, I think that's enough for one night," she finally answers.
Grace abruplty relinquishes her grip. You fall to the ground, landing on your face and chest.
"Ooh! Are you okay, babe?" Grace asks, noticing the impact of your fall. As she asks, your now-massive underwear flutters through the air before landing gently in a pile on top of your butt.
"Imf fwine," you reply into the grass.
"Well, have you learned your lesson?" Ashley asks.
"A *lesson?* What *lesson* was I supposed to get from that? 'Stop wearing underwear?'" you snap, adjusting yourself as the three of you walk back to the cabin. (Grace and Ashley were walking; you were more so waddling as you tried to both cram your underwear back into your sweatpants while also prying out the cotton that remained stuffed up your ass)
"Ew, no. Grace says, scrunching her face. "That's worse than tighty whities." You blush at your girlfriend's critique of your underwear choice.
"The *lesson*," Ashley interjects, eager to get the conversation away from you going commando, "is to not ask your girlfriend embarassing questions like that in public! What's the matter with you, man?"
You sigh, remembering the sequence of events that led you to being hoisted airborne by your briefs like you were in high school again.
"Alright, alright. Grace, I'm sorry."
"It's ok!" Grace turns around and smooches your cheek. "It was a little weird, but it's OK."
"I just thought that you were trying to be...you know..."
Grace stops walking and turns back to you. Ashley takes a few more steps before realizing what had happened.
"You know..." you trail off, hoping Grace would fill in the blanks. She instead folds her arms and waits for you to finish.
"I-I thought you were trying to be sexy!" you finish.
"I thought we might-" you continue.
"THOUGHT WE MIGHT WHAT?" Grace shouts in a tone of voice you'd never heard from her before.
"We talked about this already! You *know* how I feel about that."
"I *know*, I *know*, but-"
"So wait," Ashley interjects. "Are you saying you were trying to get with Grace after she had her first beer?"
"What??? No!!!" You hadn't even thought about that part. After all, Grace had only had one light beer. "I mean, technically, yes, but that's not-"
You feel your face grow pale. You begin to instinctively backpedal. Grace and Ashley walk towards you menacingly, matching you step for step, eyes boring holes through you.
"C'mon guys, this is a huge mis-WHOA!"
You trip over a root sticking out of the ground, stumbling backwards until you fall hard on your still-throbbing ass. You try to push yourself backwards with your feet, but not fast enough to escape Grace and Ashley as they each reach their hands out to grab you.
"So is there anything else to this show besides a bunch of hot idiots running around the island making out?" Ashley asks, gazing at the TV as the credits begin to roll.
"Nope, that's it," Grace answers, sitting next to Ashley on the couch while holding a Solo cup full of water. "It's great, isn't it?"
"It's trash," Ashley replies, taking a sip of water out of her own cup.
"Yeah, but it's *good* trash," Grace clarifies. "You need that sometimes, you know?"
Ashley cracks a smile. "You know, you're not too bad, Carpenter."
Grace smiles back. The two "clink" their plastic cups and sip, sharing the world's most benign toast.
You, of course, can't see any of this, though you can hear the conversation faintly through the window. Outside the cabin, you hang from a sturdy tree branch with your underwear covering your entire face, making it hard to see *anything* through the thick white cotton. A sturdy tree branch runs underneath the piece of fabric between your head and your rear, putting you in both a hanging wedgie *and* an atomic wedgie simultaneously. The girls had spent enough time yanking your underwear that there was plenty of material for them to work with; still, you weren't quite sure how they'd pulled this off even now.
At first, you'd struggled to get free, swinging your arms and legs to and fro, but each movement just made things worse. After a few minutes, you simply sighed and sank into the wedgie. Your body weight slowly stretched the underwear out so your feet were now just three feet from the ground; even still, it would be some time before it stretched out enough for your feet to touch ground. Your best bet was for the girls to decide you'd been punished enough, and with their show ending, you were hoping that would come soon.
"Think we should get him down?" Ashley asks. "It's getting pretty late, and I'm sure he's *really* learned his lesson now."
Grace looked at her watch, then looked outside the window to the spot in the dark where she and Ashley had hung you up by your underwear. She thought for a moment, then turned back to Ashley smirking.
"Oh, I think we can get one more episode in first."
Amazing as always. I'm glad our protagonist finally has a girlfriend (though we'll have to se
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