You're going to have to... This is gonna suck.

His face burning, Dawn uncrossed his arms from his chest, groaning. The Headmistress grinned, reaching up to pat the androgynous young man on the head.

"Good boy! Now, stand still," she chirped.

Dawn's face flushed as the Headmistress grabbed the hem of his tank top, raising it up and causing the black cotton to rub against his back and chest. She grabbed his arms, threading them through the straps so she could pull his tank top all the way up. The moment it cleared Dawn's head, he moved to protectively shield his flat, androgynous chest, but the Headmistress stopped him by grabbing his wrist.

"Ah, ah, ah! None of that! You're a boy, no need to be shy around me! You're not the one with boobs, after all." She stuck her tongue out and winked at Dawn.

Speaking of, those massive tits were bouncing just under Dawn's eyes. He was really starting to think she wasn't wearing a bra. Though speaking of, she was a girl... "Are you sure you're okay, stripping a guy like me?"

The Headmistress crossed her arms, squishing them into her huge tits as she pouted. "How dare! I'm the Headmistress! I've done this to a lot of students, boys included!" She lowered herself to one knee and grabbed Dawn's ankle to lift his foot out of his flip-flop. Granted, she only did so to hide her expression. In truth, she'd only done this with female students... All the male students, her secretary handled. Despite her age of twenty-four, Dean Conchita Iglesias was a total nerd. When she took over the college for her mother, she gave herself a makeover to ditch her nerdy, frumpy geek look. But at heart, she was still a shut-in loser and as a result... she'd never even had a boyfriend before, let alone a first kiss! So of course, she had no experience with naked men. She was just doing her best not to look like a deer in headlights as she gazed at this beautiful young man's naked chest and gorgeous bare legs. Gulp.

Still maintaining her composure, Connie reached for the button on Dawn's baggy camo cargo shorts. She hummed a little cheerful tune to try and suppress her own rising nerves as she unzipped the front, hoping he'd take it as her just having a song stuck in her head.

She kept her eyes off his crotch and down at the shorts as she lowered them to Dawn's ankles. She gently lifted each foot in turn, disposing of the shorts with her newest student's flip-flops and tank top on the floor behind her.

Connie stood, smiling at the young man as he stood there in just a pair of briefs. A pair of... Y-front tightie-whities. O-Oh my... Gulp!

Dawn's hands were gently shielding his package. Despite his red face, he was maintaining determined eye contact with Connie, clearly challenging her, daring her to take that final step, indignant towards her regarding his increasing nudity.

Raising her head with **** bravado and a faux-confident smirk, Connie placed her hands on either side of the elastic waistband of Dawn's undies. She felt her cheeks slightly flush as the feel of her fingers against the soft, smooth, flawless skin of his feminine hips. Relax, Connie! He's just a little guy. How bad could your first penis be?