Donny Gets Caught

His heart thundering in his chest, Donny pressed the upload button and almost immediately the door to his room slammed open and his step-sister Nadine stood in the doorway. "Sprung!" she yelled victoriously, holding her phone up to show Donny the picture he had just uploaded to what he thought had been his 'secret' social media account.'

"Nadine! Um- it's not  what you-" Donny stuttered as he scrambled to cover himself. He tried to pull his too-short skirt over his panties, but ended up getting tangled in the bedsheets, leaving him completely exposed to Nadine as he struggled to free himself. But despite his efforts, the damage was already done. He knew it, and the smug smile on Nadine's face said that she knew it too.

"I KNEW you were stealing my clothes!" she said accusingly, pointing her figure at him. "I just couldn't prove it, not until now at least" she said with a grin, closing the door behind herself and sauntering confidently over to the bed.

Donny finally managed to untangle himself from the sheets and sit up, his ridiculous skirt only barely covering his still semi-hard, panty clad cock, "Please don't tell Mum and Dad" he begged, looking up at his older step-sister pleadingly, "I'll do anything!"

Nadine leaned down until her face was barely an inch from Donny's, "Oh I know little brother, don't worry. You will," she whispered. The look in her eyes gave Donny chills. "This is the beginning of a very... interesting chapter of your life" she said, her face slowly transforming into an ear-splitting grin.

"First of all Donny," Nadine said, before hesitating, "Or should I say Dani."

Alarm bells began ringing in Dani's mind as Nadine talked, but he knew he was powerless to stop her if he wanted her to keep his secret.

"I won't have an amateur for a sibling, so you're going to have to learn some new... skills" Nadine said, chuckling to herself as she knelt on the end of the bed.

"Yes Nadine, whatever you say!" he said, his voice pitched higher, in fear of what else Nadine might demand.

"Good, you can keep doing that voice, it's very feminine" Nadine complimented, ignoring the blush which rapidly spread across Donny's face as he realised what she had said.

"I think we'll start small" Nadine said, holding up a small butt plug for Dani to see.

Dani's eyes bulged. If he was being entirely honest with himself, Dani had always toyed with the idea of experimenting with anal, but had never taken the plunge by himself.

"Naughty Dani!" Nadine chided teasingly, her eyes glancing down at his crotch. Dani realised with a jolt of embarrassment that Nadine's words were making his small dick hard with anticipation, the bulge showing obviously through his exposed panties.

"Alright, turn around and lay down for me," Nadine instructed, "I want you on all fours with your chest on the bed and ass presented nicely to me" Nadine ordered crisply.

Without hesitation, Dani rolled onto his stomach and did his best to assume the position Nadine had described. He felt so vulnerable and exposed, a feeling that was only exacerbated as he felt his skirt succumbed to gravity and slid up over his hips, leaving his panty-clad ass on display for Nadine.

"This is one hell of a bubble butt Dani" Nadine complimented warmly as he felt her hands caressing his round ass enthusiastically.

"T-thank you Nadine" he mumbled into the sheets, his cheeks flaming red. He'd never had anyone compliment his body like this before and he was surprised by how good it made him feel.

Dani felt a shiver run up his spine as his step-sister's fingers slid underneath the hem of his pink panties, pulling them over his hips and leaving them taut between his thighs.

"It's very important you relax now little one" Dani heard Nadine say softly, "It might feel a little weird at first, but it'll be worth it, I promise" she explained.

Dani couldn't help but flinch slightly when he first felt her rubbing some kind of cold slick feeling substance against his virgin hole, but he slowly relaxed as Nadine made soft soothing noises under her breath, her free hand caressing his ass comfortingly.

"Now, for the main event. I've used plenty of lube, so this should slide right in" Nadine said confidently. Her fingers retreated and Dani made a conscious effort to relax as he felt the cold metal plug press gently against his tight little ring.

"Uhhh- Oooohhhh fucckkk" Dani moaned as his step-sister pushed the metal intruder slowly but smoothly deep inside him, until the head of the plug was nestled tightly between his cheeks.

"You like that Dani?" Nadine asked, amusement in her voice.

Dani only moaned in reply. He'd never felt anything like the ecstasy of being filled like this. His cock had gone from semi-flacid to rock hard in an instant and he felt like he might be close to cumming already! Nadine let her fingers trail delicately across Dani's hard cock and Dani whimpered needily.

"P-please Nadine!" be begged, his voice high pitched and feminine, "I-It feels so good" he murmured. Any thoughts of Nadine keeping his crossdressing a secret were gone, all Dani could think about were the glorious waves of ecstasy coming from his ass.

"I'm sorry little one, what was that?" Nadine asked, pressing her finger teasingly against the plug, driving it deeper inside him, "You can beg better than that can't you?"

Dani thrust his hips back towards his step-sister, desperate for more. "Please Nadine, please stroke my pathetic sissy cock, I need it, I need you!" he blurted out.

"Good girl" Nadine whispered, wrapping her slick, lube coated hand around his hard cock and began stroking rapidly.

Lasting only seconds, Dani's hips began bucking wildly under his step-sister's skillful ministrations before his small cock erupted in her hands, his whole body shaking with the amazing sensations rolling down his body. Dani collapsed sideways into a heap, his breathing coming raggedly, his body still twitching as cum continued to dribble from his cock, the plug still throbbing pleasantly in his ass.

Nadine watched on with amusement, "We have such an adventure ahead of us little one" she murmured happily, and Dani could not find it in himself to disagree.