Take it all the way (Darien pt 13)

As his fingers curled around Andrew’s cock, Darien couldn’t help but think about how this innocent young boy’s life was about to change. This was clearly a first for him, there was no doubt in Darien’s mind. Andrew was too nervous, too twitchy, too excited. He was a bomb about to go off, which Darien had no intention of defusing… but also wasn’t about to trigger, not just yet.

After one last seductive glance at Andrew’s flushed face, the final note in Darien’s carefully played prelude, he opened up his mouth and took the head of Andrew’s cock inside. It was a decent size, circumcised, with a tiny drop of pre-cum on the end. Darien lapped that up quickly as he let the boy’s dick slide inside “Emily’s” mouth.

Darien let out a perfect Emily moan as his mouth sank down Andrew’s cock. He only had to fake Emily’s tones, not the emotion; that was real and genuine. In truth, he was more turned on than he’d been in a long time.

Ever since Darien had walked into the store and seen this naive looking kid, he’d wanted to seduce him. His look and overall demeanor reminded Darien far too much of Jimmy, who’d so desperately lusted after him when disguised as Ellen Spiller. But Jimmy wasn’t an easy seduction; Darien had to bide his time. With Andrew, he wasn’t going to wait.

Slowly he allowed Andrew’s cock all the way inside his mouth, taking the boy’s member in, tighter and tighter. As he felt the tip press into the back of his throat, Darien opened up, the way he’d practiced so many times by himself, sliding dildos deep inside him. His practice was rewarded with an even greater moan from Andrew, who reached out and grabbed the blond wig attached to Darien’s mask, pushing just slightly on Darien’s head as Emily’s lips practically touched Andrew’s balls. Andrew was already becoming more confident, Darien thought.

Another Emily moan, a slight rise up on Andrew’s pole and then Darien sunk again, tongue working along the length of Andrew’s shaft.

Beneath the dress Andrew had brought him, beneath the pantyhose, beneath the silky panties and beneath the layers of latex and silicone that made up his female disguise, Darien felt his own cock throb, echoing Andrew’s arousal as he guided his female alter ego to pleasure this teenager in ways he’d never been pleasured before.

“Fuck, oh god, oh god, fuck fuck,” Andrew muttered, fingers digging in to Emily’s fake scalp, pushing Darien’s head down. Darien responded by both sinking Andrew’s cock as deep into his mouth as he could, but also by lifting one hand to cup Andrew’s balls for a second. Andrew almost spasmed in response, knees giving way, but Darien snaked his other arm around to encourage the boy to keep standing.

“Don’t go off just yet,” he whispered in Emily’s sultry tones, pulling back from Andrew’s dick for a second. “We can have a lot more fun.”

Andrew nodded in response, so Darien gave him more of what he wanted, diving onto his cock again, tongue circling, hand fondling. He moaned himself, turned on not just by the feeling of a teenager’s cock in his mouth, but much more by the fact that this teen totally believed the sexy blond in front of him was exactly what she seemed – a woman who’d walked into his store by accident, and wanted nothing more than to suck his dick to completion. The power Darien wielded in this moment was, as always, intoxicating.

Slowly Andrew was beginning to take control, as he thrust in and out of Darien’s mouth. Darien responded with some encouraging grunts and moans, allowing Andrew’s cock to push at the inside of his cheek, then bury itself in Darien’s throat once more. One hand still remained on Andrew’s balls, stroking and cupping them, but the other now moved around his body and slid shiny red fingernails between the cheeks of Andrew’s ass.

“You’re going to love this,” he whispered, before his fingertips found Andrew’s asshole. One nailed finger pushed inside. He didn’t go too fast, not wanting to alarm or even scare this boy; instead he just allowed the nail and the very tip of his finger to go in, finding Andrew’s sweet spot.

Sure enough, Andrew groaned even louder, thrusting with his hips, pushing his cock hard into Darien’s mouth. In response Darien pushed his finger in deep, probing at Andrew’s asshole, showing him that there were many ways to please a man, and that Emily knew them all.

Gradually as he worked Andrew’s asshole, balls and cock at the same time, the boy began to grow more confident, more excited. He was thrusting quickly now, Darien having to work hard to keep his lips wrapped around him. Clearly he was going to explode in Darien’s mouth before too long, which Darien had no problem with – but he didn’t want Andrew to collapse from exhaustion too soon.

Which is why he suddenly pulled out his finger, dropped his hand and came off Andrew’s dick with a soft ‘pop’.

“Let’s keep it going, hot stuff,” Emily whispered to Andrew’s incredulous face. Darien wiped away a small trace of pre-cum from around his masked mouth, knowing Emily’s lipstick was probably smeared, but also knowing that Andrew wouldn’t care.

He got to his feet, regaining his balance in the heels Andrew had picked. Putting his arms around Andrew’s neck, he leaned in and let the boy kiss this woman that he’d created, slowly pushing his tongue into the boy’s mouth, allowing him to know how a “real woman” kissed. Andrew moaned and grabbed Darien’s head, making him smile on the inside as he pushed back, separating the two of them, smiling reassuringly to Andrew.

“What did you think of your bonus, hmm?”

Andrew grinned – he had a surprisingly cute smile. “I love it,” he said. “Although I didn’t get to, uh, ‘deposit my check’ just yet.”

Darien gave an Emily giggle. “The bank’s not open yet, that’s why.”

He turned to the chair Andrew had selected for him. It had already served its purpose, allowing Darien to see just how much of a foot and shoe freak Andrew was; now it was going to help him once again.