Darien pt 16 (C)

Andrew lifted it, as if presenting it to a high priest.

Darien took the shoe, turned it around and – then staring at Andrew – rubbed the toe of the shoe gently against his pantyhose, right where Andrew’s cock might go.

Andrew moaned, almost whimpered as he watched Darien continue to rub the tip of the shoe up and down his hose. Then with a grin, Darien flipped the shoe, rubbing the thin heel over his crotch too.

“Is this the kind of thing you imagined?” he whispered to Andrew, who barely nodded. “What else? Have you thought about fucking a woman with a shoe?”

Andrew froze, as if Darien had just spoken his darkest secrets. He allowed himself a curt nod, a quick acknowledgement.

Darien wondered just how deep this young man was going to take Emily.

“You mean to tell me,” Darien said, “you have thought about taking the heel of a shoe – like this one – and then pushing it inside a woman?” Darien kept his voice businesslike, even. This was an adult discussion, not kink-shaming.

Andrew nodded again, his eyes fixed on the shoe in Darien’s feminine hand.

This, Darien thought, I have to try.

“Well then,” he said, looking at the shoe carefully. “Let’s see if we can make that happen.”

While keeping his eyes locked on Andrew for his reaction, Darien opened his mouth and slid the heel of the shoe across his outstretched tongue, moistening it. Then he turned the shoe and let it move inside his mouth, lips closing around the heel’s thin diameter. As he did this he moaned, recalling the moment earlier when Emily’s lips had closed around Andrew’s cock. After several thrusts in and out, Darien pulled the heel out and presented the shoe to Andrew.

“Now you,” he said simply, wondering for a moment if Andrew would do it.

He shouldn’t have wondered. Andrew took the shoe eagerly, opening his mouth – and after the smallest of pauses, letting the heel inside, sucking on it just as ‘Emily’ had. Darien smiled Emily’s smile, encouraging with an element of arousal. “That’s it,” he said. “Take it in, lover. All the way.”

Andrew’s eyes widened for a moment as he likely felt the heel press into the deeper recesses of his mouth. Darien let his own eyes widen in faked shock, perhaps approval. “Does that feel good?” he asked. “Are you thinking about where this heel is going to go?”

Andrew nodded, still slurping at the heel.

“Are you imagining how your cock would feel inside me, hmm? Are you jealous of this heel that’s going to get to fuck me?”

The boy nodded again. Darien nodded too, a tacit approval of their sexual contract, then plucked the shoe from Andrew’s hand. Now thoroughly coated in both of their saliva, he was no longer concerned about it sliding inside Emily’s fake pussy.

“Give me some room, lover,” he said, making Andrew back away on his knees quickly.

Pinching the pantyhose at his crotch, Darien pulled at it until it ripped, making a hole large enough to be accessible. Then he slipped his hand inside the hose and pulled the panties that Andrew had selected to one side, exposing the trimmed hair of his false cunt.

“Think she can take it?”

Darien didn’t wait for Andrew to answer. Instead, rather theatrically, he turned the shoe around and slowly pushed the end of the heel directly inside his fake pussy, giving out an elongated, exaggerated moan as it slipped inside, saliva acting as an excellent lubricant.

“Mmm, oh my,” he said, narrowing his eyes even though he felt nothing between his legs. “That’s better than I expected, baby. It actually feels… very good.”

Andrew looked like he was about ready to burst. His cock was fully erect, up like a flagpole between his legs. Darien wondered for a second if he could manage to make someone cum without even touching them. He was also a little confused that Andrew wasn’t jerking off already, but figured he’d give it time.

Being careful not to scrape at the interior of his faked female anatomy, Darien pulled the heel out a little then slowly sank it back in, half-watching for Andrew’s reaction. The boy’s eyes were fixed on Darien’s hands, on the shoe itself.

For a second Darien wondered if Andrew would notice the heel wasn’t getting any more wet, the surface not glistening as it came out. Beyond the remnants of saliva, the only moisture would come from Darien’s leaking pre-cum, an amount nowhere near what a woman might produce. Still, Darien felt relatively confident that Andrew wouldn’t know the difference, and was probably blinded by the fact a deeply-held fantasy was coming true before his eyes.

Time to test the theory.

Locking eyes with Andrew, Darien pushed the heel back inside him, letting it sink in deeper than before – one inch, two inches, three – until the sole of the shoe lay flat against Darien’s lower abdomen, like a circus trick for Andrew’s appreciation. Darien slid the heel back out again then thrust it in once more, a little faster, a little more aggressive – but still careful, knowing one false move could rip his disguise in half.

On the third thrust, all the way in, the tip of the heel connected with the base of his cock. The groan Darien gave then was absolutely real.

“Oh my god, fuck! What – god that feels good!”

Tempering his own surprise, Darien focused on his performance, remembering he was Emily, a woman, a woman inserting something into her vagina to get herself off. Searching for similar moments in the past, he remembered experimenting with using a vibrator, mostly for research; he’d tried non-vibrating dildos too, which this was much more similar to, except not quite as broad, or designed for this particular hole.

Improvising a sex toy was worth it though, for the enraptured look on Andrew’s face.

“Is this what you want? Is this what you fantasized about?” Darien asked, beginning to speed up his movements with the heel, pushing it in, pulling it out, feeling a sudden surge of excitement every time it connected with his cock. “Can you imagine your teacher doing this, hmm? Can you imagine your teacher sitting on her desk, legs spread wide, pantyhose ripped open, fucking herself with the heel of her shoe? Is that what you want her to do?”

Andrew nodded, practically panting. Darien noticed his arms were almost quivering, like an invisible force was holding him back.

“God, that’s so fucking hot,” Darien said, still looking at Andrew’s arms and overall stance. “You’re so fucking filthy, Andrew,” he added, wondering if somehow his dirty talk wasn’t enough for this boy. But Andrew blushed crimson red at that remark and his cock throbbed noticeably, so Darien pressed on, feeling the pressure of the heel on his cock each time the shoe went all the way in. The tip would press down, cutting off his blood flow, stimulating his erection in much the same way a cock ring might. He knew it would make him cum, likely soon – and while he felt no guilt at allowing ‘Emily’ to finally find release, he also wanted Andrew more involved than he was.

“I really do want to be your teacher,” Darien said, knowing it would never happen, but happy to push Andrew’s fantasy. “It’d be amazing, coming to work every day, wearing heels like this, knowing you’re staring at my every movement. Do you think you’d make a move on me, Andrew? Or would you just go home every night and jerk off thinking about these shoes?”

Still not touching his engorged cock, Andrew looked a little flustered at the question, but managed to nod. “I think – I hope I would,” he said. “You’re too hot to ignore. I’d have to ask you out for a drink.”

Darien laughed, somewhat unintentionally. “I’m pretty sure you’re below drinking age, Andrew.”

Again, Andrew looked embarrassed. “Well – what about a movie?”

Darien shrugged, sliding the heel back inside his pussy again. “What kind of movie are we talking about, honey?”

“Some boring Hollywood thing,” Andrew said.

“Or maybe we could just… Netflix and chill,” Darien suggested. “You know what that means, don't you?” Andrew nodded. “Maybe we can find some fun movies with sexy ladies in hot shoes. Or perhaps we could just make those movies… ourselves.”

Andrew’s arms twitched, like he wanted to leap forward or grab Darien, but he didn’t move – until Darien reached out. It was time. He wanted to climax and he wanted to see if Andrew would, at least once more. That meant he needed to take things to the next logical level.

Darien let go of the shoe, leaving it hanging improbably out of Emily’s pussy for a moment. He took Andrew’s hand, pulling it from his side like it was glued there, and guided Andrew back to the shoe.

“Now,” Darien said in a low Emily voice. “I want you to fuck me with this. You need to be very careful, Andrew. You need to do exactly what I say. Understood?”

Andrew nodded, his eyes wide, a bead of sweat forming on his brow.

Darien guided his hand, mimicking his own movements, showing Andrew just how deep he could go. Andrew copied those movements once, twice before Darien dropped his own hand, letting Andrew go solo. Darien placed his hands on each of his hose-clad thighs and lifted his ass so that Emily’s cunt was front and center, allowing Andrew full access to realize his foot fetish fantasy.

“That’s it,” Darien said encouragingly, but truthfully. Andrew was managing to press the heel pretty close to where Darien had been pressing it. “A little to the left – yep, ahh, yes…”

Andrew looked extremely focused, which Darien appreciated, but he was still aware the boy had a hand free. “Don’t you want to touch yourself?” he finally asked.

“Fuck yes – but if I do I’ll explode–”

Darien understood. He laughed in Emily’s sexiest tones. “Don’t worry. That’ll improve as you get older.” Andrew shifted his grip slightly. “Oh, yeah that’s it, that’s it honey… just like that.”

It was obvious from the look on Andrew’s face that he both wanted to touch himself, and to keep his fantasy going. One wasn’t incompatible with the other in Darien’s eyes, but he knew once Andrew came again he likely wasn’t going to want to keep “pleasuring Emily”, which meant he needed to finish things off, while also giving Andrew what he desperately wanted.

“Andrew, I want you to do me a favor,” Darien said. “I want you to hold that shoe still, okay? And then I want you to touch your cock for me. Will you do that? I want you to cum again, only this time I’ll get to see it, get to feel your jizz all over me. Will you do that?”

Naturally, Andrew nodded. He slid the shoe out a little, switched hands and then held it still. His right grabbed his cock, making him groan in anticipation.

“That’s it,” Darien said encouragingly. “Now hold tight honey, because I’m going to fuck myself with that shoe and I don’t want it to move.” Andrew nodded, his focus clearly on his cock now.

Darien held Andrew’s wrist and lifted up his hips, allowing the heel of the shoe Andrew held to sink into his fake pussy once more. After a couple of experimental moves, he found his sweet spot. The moment when the heel pressed into his cock, right at the base, forcing the blood to flow and increase his arousal with every movement.

Meanwhile Andrew was stroking himself, slowly gathering speed. His moaning was near constant now, his breath coming in gasps.

“Can’t stop thinking about walking into your classroom,” Darien said as he lifted his hips once more, impaling himself on the heel, the proxy cock of Andrew’s that was fucking Emily. “Wearing heels like this, or maybe some tight, tight boots, god yes, Italian boots with a stiletto heel that are tight on my calves, baby–”

Darien was lost in his own fantasies now, the images he’d always craved of different faces, different women that he would portray, facing him in a mirror, smiling knowingly at him, completely aware that their appearance was turning him on. They’d turn and glance at him, sometimes more than once, then maybe if he was good they’d slide up their skirts and let Darien see their lingerie, their hosiery. And every now and again, that slow reveal would show something unexpected. A young man’s cock, hard, rigid with excitement, nestled between ‘her’ legs, a surreal sight next to a pair of black stockings or an expensive pair of crotchless hose. He wished right then that was exactly what was between his legs, a hard cock that Andrew would worship like he’d worshipped Darien’s feet, like he’d licked the heel of those shoes… but that wasn’t going to happen, because Darien had fooled this young man, fooled him like he would fool so many others with this new disguise, this new face.

The thought of that was what was driving Darien to the edge, taking him to climax. He wasn’t even sure what he was saying now, only knowing that he was saying it as Emily. “You’d fuck me in the classroom wouldn’t you,” he said. “Take me while I’m wearing those boots, or some heels, or some other fucking slutty outfit, isn’t that right Andrew?” Grunting and moaning was all Darien heard in reply. “I could be your secret slut teacher Andrew, your secret lover, the person you’d enjoy all your fetishes with, who’d buy the shoes, wear the boots and – ohh fuck, god, yes I’d do all of that, fuck me fuck me yessss!”

It finally happened, Darien’s climax overwhelming him, welling upwards to overwhelm his fake crotch, channeling through the rubber to leak outwards, covering the heel he was still fucking with his sticky, warm cum. At the same time Andrew shouted aloud as he came once again, fist pumping, his own stream of cum bursting forth, spattering the heel, Andrew’s hand and Darien with white translucent liquid.