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Chapter 7
by ChaosRiderWolf
Pick a time, or pussy out?
You need to sleep on it. Aim for tomorrow.
You shake your head. "I... I can't do it. Not today, anyhow. Uh... tomorrow, should be fine?"
Sasha nods. "Like I said, no worries. Meet me in the gym, early. Probably around six or so, and make absolutely certain you've got your day clear. It's gonna be a long one." You nod nervously, and Sasha pinches your cheek, shaking it, then walking away, and disappearing around the corner. You blinked a few times. That... that just happened. And now you had agreed to something you couldn't easily walk away from. Fuuuuuuuck. You decided to head home, give yourself time to think things over. And you still had history! How had this happened? Your walk home is uneventful, though a bad step reveals you had forgotten about your wedgie, leaving your panties stuck in your ass all the way home. You make it home, flopping your bag onto the floor and your body onto the bed. You reach back, finally able to pull the silk back into place, and then lay there a few minutes, contemplating what the next morning would bring. You sigh, and bury your face into your pillows, before managing to pull yourself out of bed. You decide some time on the computer might distract you before you had to go to history later.
A few hours later finds you in history. And many more after finds you in bed, laundry done, restless with anticipation and anxiety. Why the gym? Why so early? Why did it have to involve the whole day? You manage to drift off, but that's not a respite for you, as your dreams are invaded by visions of you riding Sasha reverse cowgirl style in the gym in front of a roaring crowd. Your pink silk panties are hanging around one of your ankles. Sasha slams into you, hilt deep, emptying her balls into you and causing you to give up on supporting yourself with your legs, falling onto her cock fully. You reach to stroke your dick, so close to cumming, but Sasha grips your wrists, ready to start pounding again. You were so cloooose....
BEEP. BEEP. BEEP. BEEP. Mother. Fucker. Your eyes open lazily, pawing at your phone, managing to get the alarm off. Ugh... why did this have to be so early? You look closer at your phone, and your heart sinks. That wasn't your first alarm, you'd slept through a couple. Fuck, you'd have to hurry a bit to make it there by six. You scurry into your shower, still horny from your dream. Frustratingly, you wouldn't have time to deal with it. You hoped that whatever was in your future, you'd at least get to cum... you shake your head, and clean up. Your routine today is somewhat rushed. A snacky breakfast, and a thrown together outfit. You picked something less... risky, this time, one of your only pairs of boxers, a t-shirt of Astolfo, and some normal jeans, as opposed to a tighter pair. Some short socks and your sneakers round it out. Even if you still looked pretty girly, at least your outfit wouldn't be as much of a problem going into this. You hesitated, considering whether you wanted it to a problem or not... but you're low on time, and leave, ultimately deciding it may not even matter. Sasha had already seen your panties, and you may not be keeping your clothes anyhow.
It's a chilly, lonely walk to the gym, though your brisk pace at least keeps you somewhat warm. You make your way there unimpeded, and look through the windows on the main doors. She's there already, with a handful of other girls. Other soccer players, you guessed. They were sitting on the bleachers, just talking with each other, a duffel bag next to them. You steadied your nerve, and opened up the doors. The girls turned to look, some of them grinning, none as wide as Sasha though. She alone stood up, waving you over. "Few minutes late, that's a surprise, honestly. Figured you'd get here early. Maybe I had you wrong, at least a bit?" You nodded, deciding that sounded better than just having missed some alarms. "Well, either way, you're here. Ready to take care of your debt?" You nod again, eager to get on with this... to uh, get rid of the video, of course. Nothing more. "Good. First, get all that off. You've got a different outfit for today."
Well, that answered that. What you'd worn here hadn't mattered in the slightest. You dropped your bag, stripping your first few pieces of clothing slowly, but picking up as you revealed more, wanting to be covered up again. You got a few boos as you revealed your boxers. Sasha must have told the girls about your... other, underwear choice. Sasha just smiled and shook her head. "Figured you could dodge some embarrassment with normal underwear? Good try, but we came prepared." As you stand there naked, Sasha opens her duffel bag, and withdraws a number of items, each one more concerning. Some pure white panties, white high thigh stockings, a very short schoolgirl's skirt, a white bra with padding, and a white button down blouse seemed to be your outfit of the day. However, there was also duct tape, two dildos, a bottle of lube, and some handcuffs. "Alright, turn around and bend over. Step by step, ya know?" You stare, wide-eyed at the spread of things in front of you, before eventually, slowly doing as instructed. You held your knees for support, and a cool sensation hit your ass, the lube being squirted and spread into your ass, and the dildo is slipped inside. You moan, legs shaking slightly, and Sasha grabs your hair, yanking you to your feet.
"Moan again. It's funny, and kinda hot." She smacks your ass, hard, hand still gripping your hair, and you can't help but oblige her. The moan is cut this time, another of the girls stuffing the other dildo into your mouth. It's flared enough to allow it to lodge in your mouth without **** you, and you moan as the rest of the girls begin manhandling you, everyone helping get you ready. The panties are slipped on, a couple of odd, plasticy protrusions going along with the cotton, but you don't have time to think about it as the rest of your outfit is placed on you. Once you're clad in everything, your arms are dragged behind your back and cuffed together at the wrist, and your mouth is covered in duct tape, further keeping the dildo you were sucking on in place. Your blouse was left unbuttoned, and your bra was loosened, threatening to slip from covering your nipples. The skirt also isn't tight, likely to fall off if you didn't focus on keeping it around your hips. Sasha stepped back, snapping a picture with her phone, showing it to you. You looked like a fetishized schoolgirl, bullied and ready for use. Mouth taped up, hands incapable of covering up, bra threatening to reveal your chest. Thigh high stockings to accentuate your long legs, highlighting your inner thighs. Your skirt was a joke, your panties were clearly visible to anyone, and so was your tiny bulge. You'd gone hard a while ago, and were trying to ignore that fact, but knowing how obvious it would be to anyone that looked at you was... incredibly arousing. Clearly you were much more of an exhibitionist than you thought.
Sasha gives you plenty of time to look, before putting it away, and nodding at one of the girls still behind you. "Yep. That's what everyone's gonna be looking at. Sexy, right?" Your eyes widen. Wasn't the point to avoid more people seeing you? Your world went dark as a blindfold is tied around your eyes. Now you couldn't see a damn thing, and that only heightened the sensations you were feeling. "Now, let's get you moving. I'll explain how this'll work along the way." Wait, were you going to have to do something? How? You were completely helpless! You give a muffled squeak as the back of your panties are yanked up, driving the dildo inside you deeper, and reminding you of the mysterious plastic feeling. You started to be dragged, and stumbled along, trying to keep up with whoever was holding your impromptu leash. As you walked, you also had to focus on Sasha explaining what was about to happen. You'd be on display, apparently, and the excuse was to raise awareness and money for anti-bullying stuff? You had trouble believing the college would go for that... but you guessed sports stars had a bit more pull than your average student, so maybe it'd work. Didn't matter much to you, you'd have to deal with at least part of it. If you raised a lot of money, you'd be off the hook. A decent amount, and you'd have one more thing to do. A little, or none at all? You were in big trouble. You weren't sure how you were supposed to affect the amount you earned. Look pretty and bullied, you guess?
Sasha's explanation stopped about when your little journey did. You knew you were outside, the cold air was testament to that. The grip on your panties was shifted, and you felt them get tugged a bit higher. You felt strong hands ruffle your hair, and then you were lifted into the air by your panties, legs kicking wildly from the intense wedgie, cotton flying up your ass. You cried out, and you heard the girls laughing amongst themselves. Sasha called out as you ascended. "Don't worry, you won't be going up too high! But we've got a whole flagpole, and your panties are strong, so it'll be just high enough to be a good decoration!" A flagpole wedgie? You'd never imagined being the recipient of one, and the thought of being treated to such a classic form of humiliation left you harder than ever, despite the cold air. Your nipples hardened as well, and the motion of you being raised into the air caused the bra to slip off them, leaving it as mere decoration on your torso. You squirmed, horny as hell already. Your motion halted, and you started swaying lightly, the breeze not too strong, thankfully.
Sasha called out one last time. "Alright, you're all set. See you in a while, so settle in and enjoy! Oh, right, one last thing, so you're not too bored...." The mystery of the plastic in your panties was finally solved. An egg vibrator on the underside of your dick came to life. The other piece must have been its battery. Luckily, and unluckily, it wasn't much stimulation, just enough to tease you even more. Oh god, you hoped it picked up. If it was going to edge you for hours, you might lose your mind. You moaned, and kicked your stocking-clad legs, trying to bring yourself a little closer to orgasm. The fact that there was no laughter told you you were without an audience at the moment. This was going to be a very, very long day.
How much do you earn?
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The Wrong Day to Wear Panties
A college femboy accidentally reveals he's wearing panties to the wrong person....
You might enjoy the softness of panties on your less than impressive cock, but wearing them was always a danger. That filled you with a thrill... will it still be worth it when a jerk of a jock finds out and abuses that fact? First story, bully's gender is up to you. Two versions, one where you make every single decision, having total control, and one where you make some, and some are out of your hands, leaving you a little more helpless.
Updated on Mar 31, 2022
by ChaosRiderWolf
Created on Nov 27, 2021
by ChaosRiderWolf
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