Darien pt 16 (B)

(Note: Yes, there's more coming. As I finish this out, I wanted to keep posting pieces rather than hold it back for one huge post. Hopefully that's okay with you! Zero doubt though, this story will officially be done this week. 😅 )

He pressed his hands down on Andrew’s head, increasing the urgency of his acting. He’d show him just how much his tongue was ‘working’ on Emily.

“Fuck yes, oh fuck yes, Andrew,” Darien moaned, being careful to maintain Emily’s voice. “You’re doing so well honey, so fucking well – you’re a natural, just like I knew you would be. Keep going, keep licking out my pussy, baby!”

Andrew moaned even louder, acknowledging the praise, tongue pressing harder on Darien’s fake vagina through the thin hose. Darien ran his female hands over Andrew’s head, messing up his hair, nails digging in slightly as he felt Andrew press with his tongue. He still felt very little, but Andrew didn’t know that. To simulate Emily’s rising excitement he pushed his hips forward, encouraging Andrew, moaning over and over with every thrust he made.

A few more minutes passed with them locked together, Darien sneaking sideways glances at his phone camera, thinking about the footage he’d see later, how he’d remember Andrew for a long time after today. Andrew would remember it too, he was certain of that – after all, the recorded footage wasn’t just for Darien’s benefit. He groaned as he thought about how he was going to send Andrew the video too, edited a little perhaps, to remind him of the time that a young woman allowed him to fuck her in the ass, right here at his store.

Fooling boys like Andrew was incredible, but part of Darien relished the illusion of memory even more. Andrew would remember one thing, Darien another – a split perspective unique to Darien’s disguises.

For a second his mind went back to the moment he’d walked into Jimmy’s high school class for the first time as Ellen Spiller, knowing that only Jimmy himself knew the truth about who their new substitute really was. Everyone else in that classroom would remember ‘Miss Spiller’ standing in front of the chalkboard, writing her name in large, flowing script as she introduced herself. Only Darien would remember the feeling of the disguise on his body, wondering as he moved if any of the boys beyond Jimmy were paying attention to his Ellen impersonation.

There was one, of course. One who would, like Darien, remember that week with ‘Miss Spiller’ very differently. Tony Kincer.

Tony, Tony, Tony… even though he was with Andrew that second, Darien couldn’t help but smile when he thought of Tony. If Darien hadn’t had such a long, unrequited crush on Jimmy, he really thought Tony would have been a willing target for Darien’s version of Ellen Spiller. As it was, he’d had to settle for using Tony as his ‘practice’ for seducing Jimmy, which had started outside that classroom when he’d forced Tony to admit that he’d been staring at ‘Miss Spiller’ for the entire lesson and had commented on ‘her’ ass. Getting Tony to admit that in person, completely subverting his expectations of what the relationship should be between student and teacher… it was an incredible turn-on for Darien, a moment he still thought of.

In fact, as he thought of it, he realized he was getting turned on again.

Just the memory of Tony was enough to arouse him, remembering the moment when Tony had discovered Ellen’s secret, when he’d found Darien unmasked – then later when he’d been so eager to watch Darien disguise himself as he slipped back into Ellen’s life. In many ways Tony’s reaction to Darien’s disguise was exactly what he wanted from Jimmy, but Darien had been too desperate to seduce Jimmy that he hadn’t even thought about Tony at the time.

Tony had certainly thought about Darien, though. As soon as he knew that his substitute teacher was in fact a classmate in disguise, Tony began to make his move. It had started with a hand on Darien’s leg, but quickly escalated into a full-on seduction. Darien may have led the way but Tony took the reins soon enough.

That was what Darien was missing with Andrew, he suddenly realized. Tony’s take-charge attitude. His burning desire. Perhaps it was because Tony knew, despite the disguise, that “Ellen” was really a peer, another young man, whereas the oblivious Andrew thought he was pleasing a seductive older woman. There was a key difference in power dynamic there, Darien knew – perhaps that kept Andrew from moving too fast. Tony, by contrast, had ultimately driven Darien to climax in much the same way that Andrew was attempting, except Tony knew his hand wasn’t just pressing down on pantyhose and underwear, but in fact on Darien’s hidden cock.

Andrew was never going to take charge like that, Darien knew, just as he was never going to know Darien’s secret. He could tell Andrew exactly what he needed to do to get ‘Emily’ off, but it wouldn’t be the same, wouldn’t feel (ironically enough) ‘real’. He wanted to have that feeling again, of being desired, of being with a man who knew what he wanted.

Darien’s thoughts were straying so far from the present moment that he was startled when Andrew looked up, breaking contact with Darien’s crotch.

“Is this okay?” Andrew asked.

Darien snapped back to the present, back to maintaining a perfect facade. “Yes, of course!”

“You kind of, uh… stopped making noise,” Andrew said.

“Oh, sorry,” Darien replied, mentally kicking himself for getting distracted. “I was concerned that other people might hear us.”

Andrew looked alarmed. “Did you hear other people? Is there anyone else in the store?”

“No, no – I think we’re still alone,” Darien said. “Force of habit I guess.”

Andrew smiled. “So you do this often?”

“No, not really. In fact, you’re my first.” Darien couldn’t help but smile at his double meaning. Andrew blushed, clearly proud of himself, so Darien decided to double down. “Was this ever a fantasy you had? A random woman walks into your store and… well, you know what happened next.”

Andrew opened his mouth to say something, then paused, as if he had multiple fantasies to choose from. Finally he said “Honestly? Not really. It just never occurred to me that someone would come into the store, and, uh–”

“Let you fuck her in the ass?” Darien finished, enjoying the sight of Andrew blushing once more.

“I guess so,” he said sheepishly. “Now it’s happened, I mean… I still can’t really believe it.”

Darien nodded, then took Andrew’s face between his hands, lifting him up for a soft, sensuous kiss.

“I believe it,” Darien whispered. “It definitely happened.”

Andrew looked back down between Darien’s legs. “Do you want me to keep going?”

Darien bit his lip, unsure. “Actually, no. And not because it isn’t fun, it is. It’s just–”

“We could take your hose off,” Andrew interrupted. “I mean, you look great in it, but that way I could get, you know, closer.”

Darien shook his head. “No, I’d rather keep dressed for now. That said… there is, maybe, another way you could please me.”

In his mind, Darien felt Tony Kincer’s hand pressing down between his thighs, rubbing at his fake pussy, massaging his growing cock. He wanted that again. He needed that again.

Taking hold of Andrew’s hand, Darien placed it on his thigh, then moved it upwards, dragging Andrew’s palm across the hose. Andrew took the hint, moving his hand between Darien’s thighs, lingering over his crotch area. Glancing at ‘Emily’ he pressed down, the hose rasping under his skin. Darien’s moan was real now, his eyes locking with Andrew, knowing that this could definitely work for him.

“Oh yeah,” he muttered, one hand gripping Andrew’s arm, ensuring it stayed just where it was. “That’s it. Your hand can do much more than your tongue, baby.”

Andrew’s eyes lit up. “Who are you?” he said quietly.

Darien didn’t respond, thinking this was a rhetorical question, the awed query of someone who can’t believe their luck.

“Do you live here?” Andrew added.

Realizing these were actual questions, Darien slowly nodded his head. “I live in the area, yeah. And you know my name, Andrew. It’s Emily.” He winked. “That’s all you get, though.”

“Will I see you again?” Andrew asked, his hand moving, something deep within Darien’s disguise reacting to his touch. Darien moaned again, but managed to answer.

“It’s a little complicated,” he said, which was true enough. “I guess it's possible you might see me again, but – probably not like this.”

Andrew nodded, his eyes suggesting he expected that answer. “But you do live around here, so we might run into each other. It’s kind of a small town.”

Darien half nodded. “I guess it’s possible,” he said, while thinking it all depended on what mask he chose to wear. He knew he could return to the store tomorrow, even be served by Andrew again, but as a totally different person. Perhaps Ellen Spiller. Gina Talavera. Or some other identity. Andrew wouldn’t have a clue, but Darien would know. The reminder of this fact made his cock twitch.

“What do you do?” Andrew asked.

A little annoyed, Darien cast a look at his crotch. “Aren’t you supposed to be doing something else right now, instead of interrogating me?” He smiled so Andrew would know he wasn’t really annoyed, but definitely wanted to change the subject.

“Sorry,” Andrew said, blushing one more time. He continued slowly stroking and massaging between Darien’s legs.

The truth was Darien knew exactly what Emily did, or rather would do. There was still paperwork to be worked on, interviews to happen, but he felt confident – both in Emily’s future career, and in his own disguise skills. Confident enough to admit the ‘truth’ to Andrew. “I'm a teacher, since you asked.”

“Really? Like, high school?”

Darien nodded.

Andrew looked like he wanted to say “I’m still in high school!” but then realized at the last second that perhaps his credibility as a lover might suffer if he admitted it.

Darien changed the subject. “So, have you ever had a teacher that looks like me?”

Andrew shook his head. “Of course not.”

“Would you like a teacher that looks like me?”

“Well, obviously,” Andrew said, chuckling.

“Would you like to fuck a teacher that looks like me?”

Andrew’s hand pressed hard enough that it connected deeply with Darien’s hidden cock. “Yes,” he said. “I would very much like that.”

“Can you imagine it?” Darien said, starting to feel his fantasy take over. “Me, being your teacher?”

Darien could certainly imagine it, thinking back to the classes he’d taken as Ellen Spiller’s literal substitute. He remembered the fresh young faces in front of him, some of them bored, some of them engaged, none of them aware that the face beneath the mask mirrored their own. As he walked around the classroom wearing the actual clothing Ellen wore, displaying his deception for all of them to see, his confidence and excitement was hard to contain. Even Jimmy and Tony would have been clueless if the real Ellen Spiller hadn’t insisted that Darien tell his best friend what was going on.

That feeling of being completely in control, of becoming a completely different person, someone who was sometimes respected, sometimes desired by others of Darien’s age… it had always been intoxicating to him. A heady concoction of deception, teenage adolescence, the balance of power between teachers and pupils and a lingering, almost tangible sexuality.

“Tell me,” Darien continued, feeling breathless, “what it would be like if I was your teacher?”

“It’d be amazing,” Andrew said. “To have someone like you in class? I’d be there for sure.” He frowned for a second, knowing he might have given himself away, but Darien didn’t react.

“And in class – what would you want to see me wearing?”

Instantly Andrew replied, “Something like this, of course.”

Darien chuckled at the suggestion. “It’s probably not very practical for school. Maybe there’s something else here that might be more suitable.”

Andrew grinned. “I’m sure there is, if you want to go try something on?”

Darien shook his head. “Sorry, but I don’t have time for more clothes shopping today. Maybe in the future. In the meantime… please continue and tell me about being seduced by your teacher.” Andrew smiled and nodded. “Oh, and don’t stop doing what you’re doing… down there.”

Andrew pressed his hand firmly between Darien’s legs, fingertips brushing against his hose. Beneath the layers of his disguise, Darien could feel his pliant rubber pussy being pushed against his cock. He groaned in Emily’s tones, making sure his young lover knew exactly what he needed to do to turn ‘Emily’ on.

“Considering this is my fantasy,” Andrew said, “I think I should get to dress you anyway I like. So yeah, I want you to be in this outfit – or something even sexier.”

“Okay,” Darien said. “So I walk into school in this outfit – maybe I’m your substitute for the day?”

Andrew nodded. “Yeah, that’s right. You can substitute for my boring old chemistry teacher or whatever.”

“Sorry, chemistry’s not my specialist subject. Is history okay?”

“Sure.” Andrew said with a smile. “That’s boring too.”

Darien laughed, feeling both turned on and weirdly comfortable with Andrew now. He placed his hand on top of Andrew’s hand, encouraging him to keep rubbing, to keep Emily happy.

“So I walk into your history class,” Darien said. “I’m wearing this outfit, heels and all. Let me guess, you can’t stop looking at my legs?”

Andrew nodded. “And you’d have to walk past my desk,” he said. “The entrance is at the back, so you’d have to go that way.”

“Meaning you can get a good look at my legs and heels on the way, hmm?”

Andrew blushed a little, but couldn’t stop his smile.

“Would you like me to stop, maybe bend over? Perhaps you’ve dropped a pencil right in front of your desk.”

“Sure, why not?” Andrew said, grinning. “Do you think I’d be able to see up your skirt?”

“You’d better not be looking that close, or it’s detention for you, young man,” Darien said, smiling back. He issued another feminine groan as Andrew pressed down with his fingers, beginning to establish a rhythm with his movements.

“I keep walking,” Darien continued, “and then I turn around and I sit on the edge of the desk… and I cross my legs. You can’t keep your eyes off them, can you?”

“No,” Andrew said, his voice sounding slightly hoarse.

“But really, you’re staring at my heels, aren’t you, Andrew? Staring at my heels and imagining them in your hands. Isn’t that right?”

“Yes,” Andrew admitted.

“Tell me, sometimes – when you’re all alone in the store – do you go and find these shoes? Grab them from your special, personal stock?”

Andrew could only nod.

“And then what do you do with them, Andrew?”

“I touch them,” Andrew said, his voice barely a whisper.

“Is that all? You just touch them?”

“I rub them,” Andrew admitted.

“And then what?” Darien looked into Andrew’s eyes, meaning what he said. “It’s okay, Andrew. You can tell me. Your secret’s safe with me.”

Andrew looked away, almost taking his hand with it, but Darien pressed down, keeping him held. “Tell me,” he said, in an insistent tone for Emily.

“Sometimes… I jerk off while I'm touching them.”

“Ahh,” Darien said, “now we finally get to it. I thought you had a thing for these shoes. Or is it just heels in general?”

Andrew looked downwards, apparently embarrassed. Darien took hold of his chin and made him look into his eyes. “I told you, your secret is safe,” Darien said. “I assume if you like shoes, you like feet and legs.”

Andrew nodded again. “I couldn’t believe how good you looked coming in here,” he said. “Getting to put these shoes on you, it was like a dream come true.”

“Do you want to do anything with these shoes now?” Darien said.

Andrew looked slightly confused, maybe concerned.

“It’s alright,” Darien said. “I don’t mind. In fact, maybe I can give you some tips.”

Andrew said “Sure,” and tentatively drew his hand back, which Darien allowed.

“Take them off me, to start,” Darien said, smiling as Andrew practically collapsed to the floor. His hands cradled the heels as if they were holy relics. Darien smiled as Andrew slipped off the first shoe. Andrew was sharing his innermost secrets, all the while not knowing about ’Emily’s’ own secret.

“Give me the shoe,” Darien said.