Plucky Penny And The Demon Of Doom

An

Angels & Demons

novelette

Part of the

Virtual Literotica Convention 2025

event

— — —

PLUCKY PENNY & THE DEMON OF DOOM

by Emily Miller &

Penny Thompson

— — —

Where had my demon girlfriend got to? Fiancée, I corrected myself, glancing at the diamond on my ring finger. It was so pretty; even - I thought - under the rather too yellowly lights of the Grand City Hotel ballroom. Shiny things can distract me; particularly sentimental shiny things. I pulled myself together and went back to scanning the crowd.

There were all sorts. Precisely what you'd expect a bunch of horny writers to create. Attire ranged from the suggestive to the close to arrestable, and that was just the men. Unlike most of the happily oblivious throng, I knew who I was, and what I was doing here; aside from looking for my errant partner, that is.

Emma and I were on yet another mission. It was part of our positions in the Earthly Chapter of The Avenging Angels [also incorporating Demons], or - more prosaically - Emma's Escorts. I was out on official ECOTAA[AID] business when Emma had been briefed about our task. She'd not exactly been forthcoming about things. She liked to be enigmatic, when given the opportunity. She-demons, right? Gotta love 'em.

Before we left? My girlfriend said that there was no time to explain. En route? Well at least I didn't have to carry Emma anymore - now that Lucy had given her back her wings - but the wind noise didn't make for easy conversation. All I'd been able to make out was that we were flying to a convention featuring characters from erotic literature; weird, right? And that someone there needed our help.

Once we had landed and both absorbed our wings, Emma finally revealed that she had to find someone important. And - rather mysteriously - added that, while most delegates would be having a blast, my job was to keep an eye out for anyone who seemed to be out of sorts.

"This is really important, Lily. If you come across an attendee who is getting all depressed, or existential, or nihilistic, find a way to make them feel better about life, OK?"

"Sure," I replied, "but what... and why...?"

"No time to explain," said Emma annoyingly. "You'll think of something. Gotta go, but remember," she added, portentously, "their lives - all of our lives - could depend on this one thing."

"No, no, no!" It took a lot to get me riled, but Emma could do it if anyone could. "I need more info than that, what if something happens to you? Spill, OK?"

So Emma spilled. She spilled quickly, and what she told me left me in no doubt about the true severity of the situation.

"Got it now?" she asked.

I nodded, still absorbing the news that my girlfriend had imparted. "But... don't we need back-up? Elena, or Agrat, or... maybe even Lucy herself?"

"No time, they are all busy, or too far away. Now I really gotta go. We good?"

"Yeah, we're good," I answered reluctantly.

I let my partner kiss my cheek, and with that the vexatious devil was gone. She vanished into the sea of milling unrealistic sexual fantasies - sorry, what I meant to say was, of course, the sea of finely-drawn and emotionally rounded characters. Angels aren't bitchy, unlike... well I don't like to say.

Angels? Yeah, that's me. Lily White, daughter of two archangels; one deceased, one missing, presumed crazed. Banished to Earth for a crime I let Emma commit. Well not really. I now understood that both Em and I had been hidden by our respective, remaining relatives. Hidden from the vengeful machinations of the Dark Lord, Asmodeus.

Asmodeus, the true reason I was parentless. Mom and Dad had both strayed into his webs, and never found a way out. He had been Head of Hell's Administrative Council, and was now awaiting trial for treason in one of Lucy Morningstar's least pleasant pits. I'd done my bit to take the scum down, but his incarceration - gratifying as it was - couldn't bring back my loved ones.

You still awake? Good. A warning, there might be some more exposition coming up. Sorry about that.

Anyway, I wasn't meant to be here. Not really. I looked at my convention ID:

Lily White - Creator: EmilyMiller

Well no, that was a lie; or at least a twisted version of the truth. Of course Emily had interviewed both me and Emma at length; she researched her biographical works thoroughly. Maybe she had embellished things a little, she's an author after all. But magical powers holding together good and evil, the dark side and the light. Crazy thing is... it's true. Angels, Demons... All of it. It's all true. Emily just documented it.

Tonight, Emma and I were once more undercover, only undercover as... ourselves. Yeah, it had confused me too. Bear with me, it may become clearer later. Let's hope so!

As I surveyed the myriad faces, one stood out. First, as it was elevated somewhat from the group she was talking to. Second, as the young woman kept staring at me before bashfully averting her eyes.

Given that Emma was nowhere to be seen, and that I was a little hazy about some of the details of our mission, I decided to be sociable.

As I walked toward her, I saw that she was wearing a pretty yellow, floral dress, with spaghetti straps showing off toned shoulders. And her legs? They seemed to go on forever. Or at least until they terminated in a cute pair of espadrille flats.

At my approach, she had lowered her face, and I could see her cheeks flush red. In something close to astonishment, I noticed that she had more freckles than me. They formed single spies on her chest and arms, and battalions on her face. There are clearly more things in Heaven and Earth...

"Hi," I said brightly, extending my hand and looking up to meet her eyes, more than a foot above me. "I'm Lily. Who are you?"

— — —

There was a look of surprise on the young woman's face, and she was indeed blushing furiously. But she nevertheless took my hand, and I was treated to a broad and genuine smile. I'd considered giving her a dose of my calming angel influence, but I figured being a bit shy was cute, and her handshake was firm.

"Hi, my name is Penny." She glanced down at her ID, I could see it read:

Penny Thompson - Creator: PennyThompson

"You're an author?" I asked.

"Yeah, just started out. But..." Here she looked confused. "But that's the other Penny... writer Penny. I'm... I'm one of her characters. At least I think."

She looked at me rather hopelessly, conveying a feeling close to distress. Maybe I'd need my angelic balm after all.

"Hey, it's weird right?" I decided some world class subterfuge was in order. I held up my own card. "I'm Emily's character. I get it."

Penny screwed up her stippled face, her nose wrinkling in a desperately appealing manner. "It just... it feels... off."

"Off?" I inquired.

"Yeah, off. Like something isn't quite right. I mean a convention for authors, that makes sense. But for characters? What's up with that? They... me included... aren't... well, real."

I thought to myself that maybe it wasn't just me and Emma who understood the true nature of this gathering. Then everyone else seemed perfectly relaxed and at ease. But I could sense that Penny was getting a little agitated.

"Maybe we could sit down... sit down and discuss it. OK?" I suggested.

Penny nodded, and together we made for one of the tables that had been set up around the edge of the ballroom. Sitting together, with a little separation from the hubbub, Penny seemed happier. It also made the height difference between us less obvious.

Penny spoke quietly. "I was wondering, maybe if my feelings had something to do with author Penny and me. Like all the other... characters... seem happy, having a good time, not worrying too much about anything. So why am I a mess? I thought about it, and I wondered whether it was because I - Penny, that is - was an author too. Maybe that's some crazy, messed up way to be; neither one thing nor another."

"Maybe," I replied, with respect in my voice, while thinking that Penny was a pretty insightful and smart woman.

"That's why... I'm sure you noticed, and that's why you came over... why I was looking at you."

"OK..." I replied noncommittally.

"I wanted to talk to another author-character. Freya was the obvious choice, but she's so busy. I guess 'cause it's her gig. Then I saw Emily Miller, and I thought, she might feel the same, she might understand."

I nodded encouragingly and went as far as to take Penny's hand in mine.

"As she's an author and a character, I thought... just like me... But then she was gone."

Suddenly it dawned on me. "And you thought I was her, right?"

"Well you do look pretty much identical. What's up with that as well?"

I had an option. Emma had taught me some of her demon mind tricks, I could wipe the last fifteen minutes from Penny's memory, and get back to searching for my fiancée.

But something about how Penny looked at me with her big emerald eyes, and the clear, honest consternation behind them, made me reconsider. It was against Emma's Escorts protocols, then I was a principal of the organization, and could probably write my own protocols. I went with my gut and took a chance.

I extended my hand to her. "Penny, come with me, if you want to live."

She looked at me in something close to horror. "What? Am I in danger?" she asked, glancing around her.

"No, well not immediately. I just... just always wanted to say that," I replied slightly sheepishly. "How about if I change that to, 'Cum with me, if you want to live?'" I looked at the young woman expectantly.

"Huh?" replied Penny.

"It's a homophone," I grinned. "You know? Come / cum."

The penny dropped with Penny. "Oh... you mean...?"

I held out my hand again, Penny took it, and we made for the suite that Emma had booked.

— — —

It felt nice holding hands in the elevator. Penny didn't say much, but she squeezed my fingers hard once, accompanied by a sideways look and half a smile. It was enough to prevent me from doing anything magical to improve her mood.

We were on the seventh floor, room 711. As the pair of us walked past the adjoining suite, we heard some unmistakable sounds. Flesh colliding with flesh repeatedly, and the mewling and cries of an impassioned woman.

This was all very quotidian for me, but Penny said quietly, "Sounds like they are having fun."

I stopped outside the next door suite. "Want to join them? I could ask nicely..."

Penny shook her head hurriedly.

"Too shy?" I inquired.

"Maybe," Penny replied, clearly with something else on her mind. "And..."

"And...?" I said as encouragingly as I could manage.

Blushing didn't really cover it anymore, my tall friend was verging on traffic light red.

"And..." she stuttered, "I thought maybe me... and... well... you...?"

She turned the last word into something resembling a plea. I'd already found Penny very sweet, but this was too much, even for an angel. Stretching up to my full 5'1", I just about managed to reach her lips, as Penny dipped her head to meet mine.

I was kinda used to electricity coursing through my body - despite my Uncle having tried hard to recalibrate the congenital spermatozoatropism that had been problematic for me at times - but the caress of Penny's half open mouth had a not dissimilar effect. 'Hey! You're meant to be the one making her feel better,' I told myself. Though I didn't really see any harm in turning our interaction into a win-win.

Out loud I said, "Whatever you desire."

Penny kissed me back, and breathed, "Thank you, you're a real angel."

"Wait! How did you...? Oh right, never mind."

I unlocked the door and had Penny to myself.

— — —

As Penny looked around the living room and took in the view, I gave myself a stern talking to. 'You know the stakes, girl. Just do what you need to do. Don't start getting carried away, Emma might need you.'

Then Penny turned to me with the most spontaneous, uncomplicated smile, her green eyes sparkling in anticipation, and it was too much to resist. Much, much too much.

I basically flung myself at her. While tall, Penny was skinny, and even my modest momentum was enough to send us both into one of the bedrooms and topple her onto the bed, with me ending up on top of her. Not a bad outcome, I told myself.

I bent forward and kissed Penny, getting a giggle that only made me kiss her harder. I'd forsworn my calming rays, but I was now powerless to prevent my arousing force from bathing her. It was wholly involuntary, and only mirroring my own desire.

Penny's eyes grew wider and her face was once more flushed. She'd been smoothing down her short dress, but now abandoned the effort. I could hear her quickened breathing, feel her racing heart, and she began to wriggle under me. Then, as her body moved, I felt something else... not something I had been expecting.

I pulled up, a confused look on my face.

"Um..." said Penny, biting her lip.

I raised my eyebrows, and she went on, "I'm... not quite like... other girls. I... um... well I'm, I guess you could say... special maybe?"

Penny shrugged, well she did her best to do so, given she was lying on her back.

"So I can feel," I replied, pushing my crotch down onto the unanticipated hardness with some interest. I sensed her uncertainty and quickly added, "It's cool, no problem. I like girls and boys, and..."

"Oh," said Penny, in an almost matter-of-fact way, "I have all the... um...

traditional

cis girl parts down there! I just have... a little extra."

"Feels more like a

lot

extra..." I mused. And I couldn't resist rubbing myself a little on her.

Penny nodded rapidly, clearly looking to gauge my reaction.

"It's all good," I smiled. "My girlfriend has one too, or at least sometimes."

"Sometimes?" It was now Penny's turn to look quizzical.

I realized I'd been too open, maintaining proper security was

so

not my thing. Time to do something. A distraction maybe, and - conveniently - what I really wanted to do in any case. Actions spoke louder than words, right?

— — —

I moved backward down the rather substantial length of my new friend's body. White boy shorts were already peeping out from where her dress had rucked up. I lifted the hem, fully exposing both Penny's underwear, and a taut abdomen with a cute 'outie' navel. But it was what her cotton panties were totally failing to contain that most took my interest.

That and, a little further down, a darker patch on her crotch. One that seemed to almost be growing in size as I looked on. The distinctive aroma of an aroused woman reached my nostrils. Then I suspected I smelled pretty much the same as her right now.

I looked up at Penny. "May I?"' As I spoke, I tilted my eyes down to indicate the subject of my question.

I got a bitten lip and a couple of quick nods in response.

Looping my fingers under the elastic of Penny's shorts, I eased them down her narrow hips. Supernatural beings love to sport oversized organs, but even I was rather taken aback by what sprung out from its cotton prison.

"That's... kinda impressive," I gasped, in something close to awe at the size of her uncut appendage.

"Um... thanks, I guess." Penny's large girl cock twitched as she spoke. "Lily, this is Nine. Nine, meet Lily." Nine bobbed in greeting.

"Hi... er... Nine," I replied, not having saluted a penis that many times before. "Why the name?"

Penny tilted her head on one side, raised her eyebrows, and just waited silently for me to catch up.

"Oh... right... of course. Sorry," I said, rather flustered at my own ineptitude, but also at the enticing prospect of getting to know Nine a little better.

"And, I know Nine is kinda hard to ignore, but there is this also." Penny reached down past her monolithic erection to part the lips of the cutest pussy I had ever seen.

"I... I..." I stuttered, my customary angelic serenity deserting me for the moment.

"Don't know where to start?" asked Penny. "It's OK, I'm kinda used to that reaction. Maybe you could start here, and see how we go."

Still lying on the bed, she dragged her dress up and over her head, revealing breasts that were pert, adorable, and - for once - didn't make me feel inadequate. Her freckles extended to cover the two modest mounds of pale flesh, with only her puffy areolae free of them. If I wasn't an engaged angel in a committed - albeit polyamorous - relationship, this could be love.

"So... maybe, you could..." Penny cupped her breasts, "and, then... well it seems like only one of us is naked..."

— — —

Much as the idea of paying some close attention to Penny's nipples was appealing, I felt she had a good point about attire. I had kicked my Keds off as soon as we entered the room, now I stood and unbuttoned my jeans, dragging them down. Reaching behind my neck, I undid the halter of the backless shirt I had selected as convenient for flying, and undid it.

"Ooh!" squealed Penny, "Another IBTC member! We should do the secret handshake."

I still struggled with human customs, and jokes could be a mystery to me on occasion, but Penny made me laugh. "Yeah, how does that go again?"

"Never mind," said Penny. "Just lose the panties."

She suddenly looked shocked, as if her own forwardness was unaccustomed, but I got that big smile again when I wriggled out of my thong; noting that - as expected - it was kinda damp and a little sticky.

— — —

I was pretty comfortable in my own skin, but something about this young woman made me feel a little shy and even uncertain. But I was certain of one thing. I wanted her. I wanted her an awful lot.

I crawled back onto the bed and placed my hands either side of Penny's expectant face, looking down at her. As she returned my gaze, Penny parted her lips just a little. I could see the blood pumping in her graceful, long neck. But it was her expressive eyes that really had me. Behind them was sweetness, curiosity and perhaps a desire to please. But I saw something else: desire. Desire that was beginning to overwhelm her. I shared the feeling, which the sensation of Nine brushing against my naked thigh did nothing to quell.

Without a word, our lips met. Not in soft caress, but with urgent, fiery pressure. Penny's tongue curled deliciously into my welcoming mouth. I felt something else on my other thigh, fingertips dancing up to an obvious destination. I shivered as she made contact with my vulva, gently stroking my now throbbing flesh.

Remembering her request, I broke from Penny's lips, and moved sideways to her ear, breathing softly into it, then nibbling on her lobe. I tracked downward, placing soft kisses on her neck, which made my new lover tense and wriggle under me; eyes closed, breath quickening.

I paused my descent briefly, with a little gasp, as Penny's fingers found my clit. Centering myself, and accepting the electricity she was sending through my nerves, I moved on determinedly. The side of her neck, her collarbone, then across to her sternum, always moving down.

I gave a soft yelp as Penny's digits - two I thought - slipped oh so easily into my warm wetness. I could tease my friend no longer. Taking her left nipple in my mouth and feeling it stiffen, I suckled her. Penny began to moan as I switched to little bites. I reached back between my legs. Nine was obstructing her girl bits, so I settled for stroking its quivering length.