My Halloween Threesome

All characters are over the age of 18. The characters and events present are created from my own overactive imagination and any resemblance to anyone is accidental. This was originally meant as a submission for the Halloween 2019 competition featuring characters from my Nude Day story Friendly Neighbourhood Succubus. However, it ended up taking longer to complete than I had anticipated so I am releasing it now! I hope you enjoy.

"Pleeease!" I pleaded.

"No." She refused.

"Pleaaaasssse!"

"No!"

"Puhleeeaaaasssee?"

Her responses stopped.

"Pretty, pretty, pretty please with a cherry on my nipple!" Lili's eyes fixed upon me at the sexual turning of the phrase, before turning back to the washing up.

"Not happening."

"But why!!!" I pleaded.

"Jane! Quit it. It's not happening because Kass is a friend of mine not just someone for you to use for sex."

"I'm not just using her for sex!" I cried offended. "It's tentacle sex Lili! Tentacle sex!" I implored leaning towards her.

Lili turned to me with exaggerated anger her eyes obviously not appreciating my humour, possibly because tentacle sex was far less exotic for her than it was for me, possibly because I was joking about having sex with a very close friend of hers. While her look was mostly exasperation and false anger, the soapy kitchen knife she brandished in my direction forced me to slow down. Noticing my eyes flick to it, she gently placed it down on the counter and turned to me drying her hands, giving the conversation her full attention.

"Jane, you know I don't mind you have sex with other people. Hell, part of the original contract was me encouraging you into sex with other people."

"You mean the contract where once a month you requested I do sexual stuff that turns me on so you get to feed off the energy that my horniness generates with your succubussy powers?"

"Yes, that contract."

"The one which led to us dating after one of your requests was for me to be naked for an entire day and you couldn't resist me?"

She sighed. "That's the one."

"The one we annulled, when we started dating five months ago, because I was willing to do way more than just one thing a month for you and you no longer needed any excuse to get sexual pleasure and relationship assistance...because I started a relationship with a very sexually active succubus?"

Her sigh was deeper this time as she turned away. "Yes, that is the contract I am referring to."

I leaned into her and pressed my nude form against her. We were always mostly naked in the house when alone, it tends to be easier when you date a demonic woman who can draw out an orgasm from you with a look or hand gesture. Frequent nudity has cut down on the cost of washing clothes considerably and I truly recommend it if you are starting your relationship with a succubic, demonic, paranormal or otherwise otherworldly entity.

With my body against her I continued my pleading, "Lili, we annulled the contract so this could be an equal relationship, so of course I don't want to do anything you aren't one hundred percent comfortable with buuuuttt..."

She looked at me with a slightly softer face.

"...but?"

I looked at her sheepishly with my shoulders slightly raised. "...but I would really enjoy it if your friend would tentacle fuck me on Halloween night."

Lili closed her eyes momentarily. Which hurt. Her eyes really were the window into her heart, more so than most. They were so expressive due to the magical changes that could alter their form and I could always gain some glimmer into what she was thinking when I looked into them. When they fluttered open, she had a resigned look on her face and her eyes were a pale, slowly swirling blue. Not a twinkle like a midnight sea, or a bright Summer sky, they were just pastel blue. I interrupted her before she could speak.

"I don't like that look. I'm sorry. Forget I said anything. I didn't mean to upset-"

"No Jane, it is fine-"

"No, no. Ignore it. Forget about it."

"No Jane. I-"

"I shouldn't have mentioned it."

"Jane!" Her irritated expression softened after she accidentally raised her voice in anger.

She composed herself and began again, "Listen, Jane, I know you would really enjoy yourself. It's a fantasy of yours, I know it is. I've seen your dreams remember." She tapped her finger to my nose as she gazed down at me. "Not to mention your search history." I blushed deeply in response to that one.

Lili pulled away from me slowly whilst caressing my arms. "And if I am honest, I know Kass would be very willing to have a cute little thing like you at her mercy." There was a bit of hungry and faraway look in her eyes now as if seeing into the future of a night that me and Kass might spend together.

I blushed but I didn't want to get my way just because Lili knew I would enjoy it. She had some reservations for this particular instance of sex outside of our relationship for a reason, I was sure. "Tentacle sex is a fantasy for a lot of people Lili. I guess I got a little carried away because it actually could be a reality for me. But a fantasy is unrelated to reality normally. If you don't want me and Kass to get together because of your friendship and our relationship then that is okay. Your friends should be people to me first not just an assortment of supernatural fetishes waiting to happen."

Lili turned to me with a knowing but compassionate smile and placed a long finger underneath my chin. "So, you'll never think about Kass' tentacles again. Even if I invite her for dinner? Never squirm in your chair when she uses one to lift her glass?"

My shiver in response gave me away completely. Lili laughed and went to resume the washing up.

"Oh my dear, that shiver just gave you away completely..." Knew it!

"...If you quiver like that with the thought then maybe I should give you over to her. Tie you down to the kitchen table and turn off all the lights. Invite her in and ease the door open-"

I smacked her arm. "Don't toy with me."

"What don't toy with you like she would?" She smiled over her shoulder at me. "She is incredibly strong you know. And not all of them are slimy. Some are soft, and sensitive. But indeed, some are strong, and firm, and would never lose their grip upon your little frame."

My mouth salivated. "Stop it!"

I groaned mildly annoyed and I went to swipe at her arm again but a lightning quick hand shot out and held my arm in place.

Sharp nails bit gently into my flesh as she turned toward me once again. Her eyes had that hunger for the future burning in them again. She pushed me back. Her presence forcing me to move far more than any of the strength in her arm.

"Some however, are slippery that is true. Wet and damp. They slither along your body, up and down every limb."

I gulped. "S- Sounds like you've had some experience." Was my feeble squeak of a reply. My legs hit the sofa before I had even realised we had crossed into the living room. Still she kept coming. A firm leg pressed between mine and her chest kept coming. I bent backwards at her approach, leaning over the sofa's back.

"Oh, I have. Maybe that is why I am a little concerned about giving you over to her. Not any human worries like jealousy, or concern about an ex, oh no."

She was leaning over me now with her eyes holding me fixed in position. Eyes burning deep inside me and lips inches from my own. Her knee ground against my suddenly aching crotch as the world behind her melted into inky blackness. Her jet-black wings had emerged from her back and encompassed the entire area around us. They expanded to fill the space as per her wish and I was soon inside a cocoon of her making. All that I could see was the faint outline of her body lit up by the glow of orange rings around her irises. Smooth, curled grey horns protruded from Lili's head, lit up in the fiery glow of her eyes. They split the shadowy wisps of her deep purple hair and seemed to twist their points towards me.

She had released my hand without me realising and it lay limp at my side. Her free hands climbed up towards me and one reached around to my back as her left clasped my chin, directing my full focus toward her. As though she did not already have it. Black, smoky substance began to trail across my skin and float in front of my eyes.

"No, my dear Jane. I am only worried that once you get a littletaste." She punctuated her word with a lick upon my neck. "Mmm. After that taste, I worry that you won't be able to break free. I worry that my little lamb will be lost forever."

"Addicted." A kiss upon my cheek.

"Obsessed." Lips placed upon my own and removed just as quick.

"Taken into a covenant you could not hope to escape from." Her eyes stared into mine, only millimetres away.

"Stolen from me by an eldritch being with power you... cannot... understand." Her breath alone parted my lips.

"Cum pet." She commanded.

And so, I did. In the cocoon of her wings and surrounded in her embrace, I orgasmed. With her bronze eyes burning through my soul and her knee pushing deep into my core, I came. My body shattered and exploded with barely a movement on the outside as my mind was flooded with images of nights of passion from the past and those in a future yet possible. A groan poured out of my mouth as my juices flowed down my bare legs and over her own. I gasped and hissed expelling all the air I could from my lungs as if my orgasm required all the space I could afford it.

My eyes snapped open as I sensed the atmosphere change and I blinked to confirm it.

Instead of orange and terrifying eyes staring into my own I was met with swollen, blue irises that surprised me. They seemed to pour into my mind and search out reassurance. Lili pressed her lips into me deeply and kissed me with a passion I was amazed at. Not hunger. Not sexual force common in our young relationship. But that of intense, overwhelming love and caring.

She broke the kiss first and I felt drool fall against my bottom lip and chin. Lili was panting hard, far harder than me despite my recent orgasm.

"I love you Jane. I really, really love you. I want to spend Halloween night with you. I won't say no to you spending time with Kass but I need to be there with you on Halloween." She was getting almost frantic now and I could see her eyes dampening.

"I am sorry. You couldn't be expected to know. Halloween it- it is special for all of us. Supernatural thoughts. They are so heightened during Halloween. The holiday it has become. Millions of people all thinking about you. Your being. Your presence. So many of us feed upon that experience. It's insane and crazy and overwhelming and... I need-". Her arms had faltered now and she was no longer controlling me with her arms but using them to steady herself. She was struggling to compose herself but she took a shaky breath.

"I need to be with you on that night."

The search for approval I saw in her eyes was something I had never seen on her before. She was shaking and her strong form was clinging to me for support.

"You idiot." I sighed with a smile on my face. She looked up at me in shock. "It means so much to you but you tried not to tell me." Her lip quivered as she looked at me.

"I'm not going to leave you. Not today. Not on a day that is special to you. Not ever. If I ever go away, I will always, always come back to you. I love you Lili. So, so much." It was then that she began sobbing into my arms. Light returned to us as her formidable wings dissolved away behind her into nothingness. Her nails returned from the claws they had transformed into and her horns slowly disappeared into the cute little nubs they normally were, hidden beneath her hair.

We stayed for some time like that, in a post-orgasmic -- turned intimately tearful embrace. The swell of her shuddery breaths pushed her chest into mine until they gradually calmed their rhythm. Her sniffs calmed after she made a tissue fly from the box across the room to dab her eyes and nose. Her dark eye makeup was miraculously returning to an unsmeared state and I started to feel a comical sense of jealousy at the speed of her recovery from that emotional release. She would barely need to wash her face. She did struggle to work up the strength of her voice after her sobs but gradually, it returned.

"About Halloween...sniff about Kass."

"Forget it Lili. Don't worry-"

"No, no. I want it. I want it." She pleaded.

"Lili..!" I tried to interrupt.

"But I will be there too."

That stopped me for a moment.

"A-are you sure?"

"Jane. Halloween is when my power and Kass' power will be at it utmost. It will be overwhelming for a human to experience being near us. Your mind will melt and refuse every few seconds."

"Um...well that-" I stammered; equal parts happy to see the light return to Lili's eyes as she looked up to me with a slightly meek smile but also mildly concerned by the content of her speech.

"The absolute height of our power. Filled to the brim with power. Of course, using it all would bring about Armageddon..." She trailed off for a second while looking into the middle distance. "...but a fraction of our powers...that wouldn't be too bad." She mused while returning her eyes to me.

"You can bring about Armageddon?"

"Um, Kass and I can but that is not important."

"I dunno. This feels pretty important to me-"

"The rise in the media's portrayal of succubi and tentacle equipped creatures really has had an impact but I have not had a chance to test it fully."

"You just said testing it fully would bring the end of the world so maybe we don't-"

"Nonsense, I said Armageddon not the end of the world but that is hardly a concern."

"You realise I live here on Earth, it is a concern-"

"Oh, my lord, you are going to break. It will be awesome!"

"Lili can we go back to saying how we love each other and will never hurt each other?"

She looked deep into me. Her eyes still a little puffy but a renewed life burned distantly behind her them. "Don't worry lover. Me and Kass' power will be so incredible we will be sure to put you back together, good as new. More or less."

"More or less? Wait Lili!" I cried as she pulled me towards the bedroom obviously becoming rapidly aroused by the frankly terrifying idea, she seemed to have concocted.

Laughing she turned back to me. "Oh, I think I am starting to get excited too Jane. This Halloween is going to be sooooo much fun!"

Being offered a threesome with your girlfriend and her friend is a surprising thing to be sure. Being told that on one particular night of the year, your supernatural girlfriend and her tentacle monster friend may gain the power to cause the end of the world is straying into slightly more alarming, rather than surprising, territory.

Being offered a threesome with said demonic girlfriend and said tentacled friend on a night where their power is so intense they could cause the end of the world, while being assured that this power will be channelled into your body during said threesome... is more than a little panic inducing.

Am I ashamed that I had sex directly following that offer without questioning it further? Maybe a little.

Would anyone else have maintained rational thought while a succubus dragged them to the bedroom after offering a mind-blowing threesome with someone who fulfils a very intimate kink you have? I would say no, so don't judge me.

Lili was not forthcoming with much information over the next week in the lead up to Halloween but I knew she had spoken to Kass. Since there was no talk of a change in plans, I was sure that Lili's adaptation of my original plan was being put into effect. I was going to be involved in a threesome with my succubus girlfriend and her tentacled old flame.

Yeah that did make me a bit wary. Lili had hinted before that her and Kass had been together, although she had been vague about their relationship and I hadn't pushed it. Since I made my request however, Lili had been more forthcoming.

Kass and Lili had never entered into a romantic relationship. Instead they had experienced several centuries being sexually active with each other in a way no mortal could ever contend with. Almost more intimidating than her just being her ex-girlfriend, right?

How was I supposed to compare to some kind of eldritch being in the bedroom? What was to stop Kass and Lili wearing me out on the first round and then spending another few centuries lovemaking while I was left to sneak out the door? That said, how did I even compare now to Kass?

I thought of myself as relatively plain even in the mortal world, how could I hold a candle to a being from Lili's realm? I occasionally had thoughts about Lili's past, and about how I was a really just a blink of the eye of her life. Lili did not have an infinite lifespan, but I knew that she had existed since before humanity and would likely outlast it. I spent that pre-Halloween week concerned that Lili was seriously lacking fulfilment due to my lack of any superhuman ability.

I dwelled on these thoughts even more due to the lack of contact with Lili through that week. She had to work extra shifts (yes she has a job, she wanted to pay rent) to get the time off for Halloween, which irritatingly landed in the middle of the week. We had both booked the Thursday of Halloween and the Friday following it. Lili had been very serious when she told me I would need the entire weekend free and even then, I may not be fully recovered come Monday. I was never truly ready for Mondays but Lili's seriousness made be believe this would be different from a hangover.

"You said you would put me back together again good as new right? I mean what are you actually going to do to me?" I had responded to her.

"Putting you back together is not the same as removing any damage." She claimed, urging me to understand the workings of her incomprehensible magical world. "We are going to bring your experience to another plain of existence Jane! And we will not be wiping your memory of it afterwards. We can easily repair you physically but you're going to need a long time to recover from such an incredible experience. I am actually rather jealous. The power gap between me and Kass is high but nothing like the gap between the two of us and you."

She framed it as a glorious thing with twinkles in her eyes but once again all I heard was separation. I wasn't on their level. That was clear and plain to see and the admiration for Kass that I heard in Lili's voice wounded me further. As the day before Halloween arrived my thoughts had darkened so much. I was millimetres from calling it off. Cancelling what I myself had asked for.

I had started to feel hypocritical. A week ago, I was begging Lili to give me my kinky time with her friend but now I would be getting a threesome including my girlfriend I was worried I would be left out?

I had resolved that going ahead with it would be for the best regardless of the outcome. When I inevitably couldn't keep up with the two otherworldly beings I dared inhabit a bed with, it might just expose some of the issues with mine and Lili's relationship. Was that what I wanted? To be proven right? To be proven inadequate?

Staring into the mirror I nearly tussled my neatly curled, relatively-recently-dyed-blonde hair in frustration but it had taken half an hour to style. I was upset but I wasn't about to ruin the time I was taking to get ready for this terrifying night.

I heard a short knock at the door. I called for her to enter and pulled my towel tighter around my body. Lili entered holding a little paper bag. I knew what it was.

Lili had informed me she had prepared my costume half-way through the week and now she pranced into the bedroom carrying it. She stood naked and with her horns slightly showing, her face shining. Gently she pulled the outfit out of the bag and held out in her arms in front of her. Despite her many years of life, her immaturity in demonic time scales showed as she stood like a proud child about to say "Ta-da!". She grinned excitedly at my reaction.