Leo's brow furrowed with confusion, both because of the odd request and the fact that Ben had actually physically stopped him from doing something, which was... uncharacteristically assertive. The boy always seemed to be walking on eggshells around him... So if this was serious enough to warrant that, he might as well hear it out. "...Alright, then. What's this about?" Leo finally asked, letting his hand come down to rest beside him.
It was far too dark to make out any sort of detail, butLeo could at least make out Ben's presence beside the bed as he shuffled awkwardly for a moment, before taking a deep breath and letting it out with a sigh. "Ann- Your daughter and I, Sir- we're not really... dating." He eventually managed. "It's more like she's... covering for me... If you get what I mean." He elaborated, voice strained.
Leo's brow furrowed, the gears in his mind grinding to a halt as this new information fell into the machinery like a stray wrench. The stray thought rattled around in his skull for a moment before he recognized it as not a wrench, but a cog! "Oh. OH!" Leo muttered as the new cog clicked into place, sliding perfectly into the clockwork, the missing piece that fit into the mechanism related to the ongoing question of Ben. The gears chugged into motion once more, and finally, the Ben mechanism turned smoothly, no strain, no hitching, no grinding...
"So... You're- it's 'gay', right? That's the right word?" Leo asked. His eyes were beginning to adjust to the darkness, at least, enough to see the boy nod. He caught a glimpse of something shiny at the boy's ear... and he thought he saw a gleam at his chest, too. "Good to know. So, uh... Well, I want you to know I support you. I don't think it's wrong or immoral or anything, or that you're going to hell, it's just part of who you are, and you're a good kid. Your secret's safe with me. And if you ever, like, help with something, or to talk about it, I'm here." He offered, trying to sound more prepared for this than he actually was, then paused, blinking. "Wait, then, is Ann..."
Ben shook his head. "No, Sir. She's definitely straight. It's, um, kind of a- a 'common interest' for us, you know?"
Leo nodded. "Okay. Good. I mean- not that there'd be anything bad if she was, just..." He rambled on for a moment. It all made so much sense now. This was why he'd never seen the two kiss, the reason their dates didn't seem exactly romantic... Who goes to see 'Dance of Death 3' on a date? "...Wait a minute. Have you two been just hanging out and calling them 'dates' to get around her curfew?" Leo asked, narrowing his eyes at the darkness.
The shape in the darkness shifted, uncomfortably. "There's- There's one more thing, Sir." Ben said, abruptly changing the subject. "O-or maybe... show you?" He added, his voice trembling for a moment. There was a moment's pause, then Ben spoke again, his voice a little more resolute. "You- you can turn on the light, now, Sir. If- if you want."
Leo wasn't sure what he was expecting when he reached over to the bedside lamp and flicked the switch, but it certainly wasn't what he saw when the lamp lit up the room. Ben stood there, a few feet back from the edge of the bed. His aqua-blue hair, jaw-length on top and shaved close on the sides, was swept to one side, falling down over his face like a waterfall, half-covering one of the boy's big, bright blue eyes. His eye makeup was expertly applied, dark blue at the outer corners, then fading toward the center to electric blue, then finally a pale, almost-white-blue at the inner corner, sparkling glitter spread all throughout. His cheeks were contoured and dusted with blush, silver stud earrings gleamed in his earlobes, and his lips were painted the same aqua as his hair, the color rich, smooth, and glossy. His front teeth sank into the lower lip slightly as he nervously stared at Leo, trying to gauge his reaction.
Leo's gaze roamed down from ben's face. He was barely dressed, the a cropped tank top of transparent turquoise mesh leaving nothing to the imagination. His chest was slender and smooth, either shaven or hairless, he couldn't tell, but his dime-sized nipples were pierced through with a pair of gleaming silver barbells. The short top left his stomach exposed, slim and supple, only a hint of muscle underneath the soft, smooth skin. His nails were painted to match the rest of his theme, aqua blue. Leo's eyes went further down, and found the teenage boy's lower half clothed in a pair of long, aqua-blue thigh-high stockings, trimmed in white, lacy frills and connected to a matching garter belt. His modesty was preserved, though barely, by a pair of lacy, blue-green panties, an obvious bulge in the material as they tried to contain what they were never meant to. Looking even further down, Leo could see he tottered on a pair of tall stiletto heels, to complete the look.
"I'm a- a perverted, crossdressing sissy, Sir." Ben announced, drawing Leo's gaze back up to his face. "And I... I want to be... your bitch. I want you to- to MAKE me your bitch. P-please, Sir, you don't have to worry about my- my penis, you don't have to- to touch it, or anything, it doesn't matter, I just- I just want to- to worship your cock... a REAL man's cock. It would be so hot... you're so- so strong, and- and manly and... BIG... Oh, god, I haven't been able to forget your cock since I saw it in the showers... I just-" Ben rambled, his expression pleading, rapidly growing desperate. "Please, Sir, I- I don't even know if- if you LIKE guys, but I- I promise I'll do good, I'll do- do anything you want, ANYTHING, I swear, I- I can just- just suck you while you watch porn, you can even- even sell me, Sir, I- I'll make sure they wear condoms and- and bring you all the money, just- just let me- Oh god, this- this was a huge m- mistake..." He whimpered, his voice faltering as he began to tremble. "Of- of COURSE this wouldn't work, I'm so STUPID, I just- I wanted it for so long, I thought if- if I showed up like this, you might- you might... use me..." He hastily tried to explain, knees turning in as his hands moved to cover himself, tears beading at the corners of his eyes. "I'm so sorry, please, please don't hate me, Sir-"
Ben went abruptly silent as Leo suddenly rose to his feet, his massive, muscular frame looming over the younger boy, a wall of earthy brown muscle, arms like tree trunks reaching toward him with rough, calloused hands that looked like they could snap his neck without even trying... He flinched in fear, squeezing his eyes shut, only to feel those massive, rough hands land on his shoulders, gripping firmly. He froze for a moment, before cracking his eyelids open, those big blue eyes slowly following Leo's thickly muscled arms up toward Leo's, his expression uncertain and afraid, only growing more so as they found Leo's chiseled face unreadable.
Leo leaned down until his lips were at the boy's ear. "We are going to have a long talk about this, boy." He half-whispered, his voice deep and rumbling, his tone leaving no question in Ben's mind that this was not a suggestion. "But in the meantime... I think I can put that mouth to a better use." He added, and suddenly, Ben felt the hands on his shoulders push, hard. His legs buckled in an instant, and he fell, landing heavily on his stocking-clad knees. The carpet softened the impact somewhat, but it still hurt. The pain was swiftly forgotten, though, as the sheets that had still clung to Leo's hips fell away, revealing the tight black boxer-briefs he wore, and the truly massive bulge contained within.
Ben swallowed, nervously, as his eyes locked on Leo's bulge. "...Yes, Sir." He muttered. The shape twitched under the fabric.