You keep your underwear, but lose your dignity.

Ashley was quick to prove herself as the worst person to be stuck naked around. She would constantly speed up or slow down to make you trip over the tiny piece of cloth wrapped tight around your ankles.
It became a game. One that was win-win for her and lose-lose for you. Either you managed to keep your briefs from slipping, but trip up and often times press up against her. This always resulted in a hard grope of whatever body part she felt needed the attention of her free hand. Or you managed to adjust your pace and feel your last defense slip slightly farther down your feet.

"Wow! What's that!" Ashley said as she suddenly went from a brisk walk to a dead stop. Predictably you weren't able to adjust fast enough and walked right into her. Apparently you where predictable enough for the keen girl to line up her hand in the perfect position to cup your penis as you pressed against her.

"What? What was what?" You ask worried that someone may be in sight of you two. Too worried to acknowledge the feeling of the soft hand hiding your dignity.

"Hmm?" Ashley hummed before giving your junk a good squeeze. Jumping to your toes you press yourself further into her grip as she let out a good laugh at your expense. "You're so jumpy John. Calm down."

"You just squeezed my dick! What did you expect, for me to stand still? And you also just scared me stiff. What the hell where where you talking about?" You say in your defense as you backed up. As you pulled out of her hand your member flopped out in a far stiffer state than it entered. Whether that was from the rush of fear or the feeling of having a girl roughly caressing it is up to debate, but the reaction from Ashley was all the same.

"Ha, ha, ha! Looks like I really did scare you stiff! You sure are bitching a lot for a guy who's getting off to this." The green haired girl laughed as she gave your boner a playful swat to send it bouncing around.

The swat sent you flying backwards. At least as far back as you could move without letting go of her hand.

"I-I'm not getting off to this! You just basically gave me a handjob, what did you expect?!"

"Pfft! That was not a handjob dude. I just felt up your dick, and gave it a nice squeeze. I'm suprised after everything that's happened to you so far that was what finally got you to pop a boner."

Something clicked in Ashley's head as her eyes lit up.

"Wait, don't tell me you're one of those guys who gets off to a girl hurting you!"

"What?! No! It's just-"

Before you could respond Ashley decided to test her theory with a hard slap on your bare ass. An echo shot through the halls of the school as you struggled to not drop her bag as you flinched.

With no free hands to rub your sore ass you instead thrusted your hips forward to alleviate the stinging sensation. In the process fully advertising that your dick was now harder than ever before. Twitching in sync to the throbbing sensation on your cheek.

"HA! That's one hell of a boner for someone who's not enjoying this!"

"S-Shut up!" Was all you could muster. Unable to explain why your body was betraying you like this.

"Man they should make it illegal for guys to wear clothes. You're so much easier to read with your cock hanging out in the open!"

You blush and recompose yourself as Ashley continued walking. The act of trying to balance your briefs between your ankles had you moving your legs in often exaggerated ways. This was bad before as it made you look like a nude marching band member, but with the addition of your impressively stiff member it was a sight to behold you walking down the halls.

Bullets of sweat dripped down your forehead as your eyes darted around. This had to be the worst position for anyone to spot you in, and it seemed Ashley also was taking notice. She gradually kept increasing pace, making your leg movement more exaggerated, and making your cock dance in a more and more humiliating way.

Eventually you made it to the door of Ms. White's classroom. Thankfully no one got to see you're march through the school. Ashley seemed a bit disappointed, but was still glowing with joy none the less.
A sigh of relief also escaped your lips as you glanced down to see that your underwear was still in tact.

"Well that was a fun first date John." Ashley said as she let go of your hand and took her bag back. "You should join me in the skatepark some time. I would love to see you get all hot and sweaty in that new uniform of yours."

"Ha! Like that will ever happen." You laugh as you're finally able to reach down and pull up your underwear. You felt a wave of relief as the tight garment made it's way back up your legs. Thank god you didn't have to worry about being seen totally naked anymore.

Or at least that's what you thought was going to happen. Once your briefs where pulled all the way up your erection erupted through the fly — unable to be contained by the tiny piece of clothing.

"No... No way! Come on fit!" You say in a panic as you tried to readjust yourself, but nothing worked. Every time you shoved your dick back in it just burst out the front or top.

"Hahaha! I love that uniform dude. Have a good time in English. Tell Chloe and Michele I said hello." Ashley said before giving you a parting spank. Hitting the exposed flesh your underwear failed to cover hard enough to send ripples through it and cause your cock to throb again.

You heard Ashley's footsteps grow distant as she laughed to herself. She was clearly very happy with the amount of humiliation she managed to squeeze out of you in such a short amount of time, and something tells you this is far from the last time she'll want to mess with you.

Now's not the time to think about that. Right now Ashley has left you with a parting gift in the shape of her hand printed onto your ass, and that gift is making your dick throb harder than ever.

'Please let there be enough time for me to settle down...' You say to yourself as you glance inside the classroom to look at the time on the clock.