With a quick decision, he decides he'd rather do it naked. "It might end up more comfortable for both of us if I do this..."
He felt embarrassed, as he stripped down in front of his childhood friend. If it wasn't for the circumstances, he'd never even think about doing this. He pulled down his underwear last, revealing his full birthday suit for Emily to see.
He could see how red her face was. "A-Alright, l-let's get this over with." "Y-yeah... It's embarrassing to be like this, but a-at least I'll see a good amount of you in return..." He smiled as he finished that. With that out of the way, he decided to ask her. "Though... Where do you want me to go?"
Her face brightened, and she stuttered out her response. "W-well... I-It'd be less embarrassing i-if I just..." She leaned back on his bed, and lifted his skirt off. He saw her skin-tight leggings, but also the thick bulge around her crotch. "Wait... You mean..."
Jeff was shocked. "Wait... How long have you been wearing these?" "M-My whole life... H-Have you really n-not known?" "Uhh... No?"
He walked forward, standing right next to her. Sitting down on the bed, he attempted to pull out the waist as far as he could. "This is going to be tight... Oh well, In we go."
He pulled her leggings down, and crawled right in, trying not to focus too much on his surroundings. He can feel when he's completely inside, as Emily closed the waistband over him. He can also feel as the leggings are pulled back up
He tries to adjust his position a bit, specifically turning around so he's not near her butt. He's able to hear Emily giggling above, and the skin-tight leggings are pressing it on all sides of him, and she's sitting directly on his stomach, making it hard to move.