Yes, but just a handjob

"Fine..." you muttered, looking toward the floor. "But I'll only jerk you off. I'm not putting your dick in my mouth or my pussy."

"But your ass is up for grabs? It looked pretty sweet, too."

"Definitely not," you said. He chuckled, reaching around and scooting the teacher's rolling chair around the desk and next to him. You slowly walked over and took a seat in it. Both of you sat there for a few moments, before you finally groaned. "Well? Are you gonna pull it out?"

"You're the one trying to earn a prize here," he said. You glared at him, but he made it clear he wasn't going to budge. Sighing, you rolled your sleeves back and then reached over toward him. Your fingers fumbled for a moment with his button and fly, not used to approaching them from the angle you were sitting at, but you finally got them undone. You then reached in, undid the fly of his boxers, and reached your hand in.

Your fingers found his shaft and went to work pulling it out. As you tugged at it, you could feel it hardening in your hand. Your breathing hitched and quickened, and you couldn't quite nail down why. Finally, you pulled it out and marveled at what you saw.

His dick was huge. It had to be nine inches, and it was thick, and warm, and... You shook your head. You needed to focus. This was just to get that picture deleted and not circulated around the school. You started moving your hand up and down his shaft. It was a familiar motion, you had jerked off a fair amount when you had been a guy, but made odd like undoing his pants because of the strange angle. You ran your thumb over the head of his dick, and it felt so different, softer and spongier than the hard shaft. It was kind of fun to play with...

Why were you thinking like that? You had one of these a couple of weeks ago. Running your fingers over the head coated them with some pre-cum, and you used that as lube. Your hand glided over his dick as you stroked him with more vigor, wanting this done with. Your arm movement caused your boobs to jiggle, which was uncomfortable and distracting, and served as a reminder that... "hey, you're a girl jerking off a guy."

He groaned and moaned, staring at you. "Talk dirty for me, baby," he said.

"Seriously?" you asked.

"I wanna hear what you want."

You glared at him for a moment... but if it made this faster...

"Cum for me," you said, staring at his dick. It was the better option, really. Looking into his eyes would feel too intimate, too real. "I want to feel you cum, I want your jizz running down my hand." You squeezed and stroked him again, and felt him tense. Jets of cum shot out of his dick, splattering onto the floor and then dribbling down his shaft and your hand, granting your false wish.

You pulled your hand away, nose wrinkling as you saw your dainty hand covered in spunk. You pressed fingers together and watched as a strand of cum extended between them. You could feel the sticky goo rapidly cooling. Randy grabbed a roll of paper towels, used one to wipe his dick off then handed it to you. That was kinda gross, but... well, his cum was already on your hand. You Wiped it off, then got the spots on the floor, then tossed them into the trash.

In the meantime, he had pulled his pants up and retrieved his phone.

"So... delete the picture now."

"I said I wanted a go at you."

"And then you said I could jerk you off."

"I said we could start with a handjob. We can finish the transaction later. Lunch is getting on," he said. "What's your phone number?"

"I'm not gonna give you my phone number," you said.

"Then I can send this pic to everyone whose number I do have..."

You groan, clenching your fists. Even after wiping the cum away you could feel the stickiness on it. You took a breath, then gave him your number. He grinned, texting you to make sure it was real, then said "I'll be in contact and we can chat about the next step." With that, he left the room. Leaving you alone, hand sticky and smelling of cum, and ashamed of what you'd just done.