Lilith

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"Morning," she said, with the biggest smile I had seen on her face, in forever.

"Morning," I replied.

"How was work?"

"Work...work was incredible," she laughed.

That was unusual...mom never spoke like this. Not since dad left, at least. I pulled out a seat across from her and sat down, lighting up a cigarette and taking a long drag from it.

"I met someone."

I almost missed what she had said, asking her to repeat herself and sure enough, she said exactly what I thought. "Who?"

"His name is Michael," she explained. "He's such a nice man...he came in for a cup of coffee last night and the restaurant was practically empty. I took my break and we ended up talking. He's a lawyer...very wealthy. He has a son of his own."

"You learned all of that about him, over one cup of coffee?"

"We just clicked really easily," she shrugged.

"I can't explain it but, once we started talking, we couldn't stop."

"You only like him cause of the money?"

Mom laughed, putting her cigarette out and shook her head. That wasn't the only reason, she explained. Mom described Michael as a very handsome man, who has a great sense of humor and apparently...he had asked her to go out with him.

They were going out later that night and she was very excited about it. I have to admit, it took me a moment but I was starting to feel happy for her. Mom hadn't even spoken about dating, since dad left and I was glad to see she was finally moving forward. Was this because of Lilith?

Maybe this was the start of the wish that I had made...maybe she was giving me just a small taste, of the happiness we could have, if I would say yes to her.

I cooked breakfast and mom went to work. I spent the rest of the day thinking about everything; Lilith, mom, the wish, my soul. By the time the sun went down, I had made up my mind...I was going to say yes, to Lilith. I was going to give her what she wanted and in exchange, Lilith would give me what I wanted. Besides, if sex with Lilith felt nearly as good as it had in that dream I had last night, I figured eternity would be pretty good.

I spent that night online, listening to music and waiting anxiously for midnight to come. Mom got home from work around 7:30 and took a quick shower, before heading out on her date with Michael.

She called me later that night and told me that she would be staying out for the night...she didn't have to explain why. I could pretty much assume, what was happening with her and her new "friend."

At 11:45 I stood from my computer chair and stretched. Taking a deep breath, I pulled my shirt over my head and tossed it to the floor. Then, I sat on the foot of my bed and stared at the clock, starting the countdown in my head; ten minutes to midnight.

Five minutes to midnight...

Three minutes...

One minute...

The clock struck twelve and I blinked, expecting Lilith to just be there, standing in the corner of my room...she was. The room suddenly turned freezing cold and my light started flickering.

Standing right in front of my bedroom door, like in my dream, Lilith was smiling back at me.

"So, Jimmy boy...what's it going to be?"

"I have a few questions," I said, in response.

"Ask away."

I took a moment, then cleared my throat. "Did you do that...with that guy Michael? Did you set all that up?"

Lilith winked, "You're guess is a good one. It's just a little sample of the life, that I can provide you in exchange for your soul."

"I figured as much," I smiled.

"Um...how does this work? I mean...are you taking me to hell?"

"Not yet," she shook her head. "You get ten years. Ten years to enjoy your own piece of the good life, and then I'll come for what's mine. Sound fair?"

Actually, it was a pretty good deal. I thought once the deal was made, it went into effect right off the bat. Figured that Lilith would snatch me up and drag me to hell...I was a bit relieved to know, that this was not the case.

"It's a deal then," I said, finally.

Lilith's eyes lit up and a wicked grin sprawled across her face.

"I knew you couldn't turn me down," she said, stepping forward.

I was still sitting on the edge of my bed, as Lilith reached out and stroked my cheek.

"Now, it's time to make it official."

Lilith raised her dress, revealing her thick cock; fully erect and pointing straight at me, just like in that dream I had.

I could practically feel the heat radiating from her member, as I licked my lips and opened my mouth. Before I could say a word, Lilith rammed her dick down my throat and I gagged.

My eyes filled with tears as my throat squeezed around her cock, my body jumping as I gagged each time she thrust into my mouth. She pushed all the way into my throat and I could feel her heavy balls, pressing against my chin. Long fingers moved slowly through my hair, taking a fistful of it and forcing my head up and down.

I was gradually starting to adjust, stretching my jaw wider then I ever would have thought possible.

Lilith pulled back and I gasped for air, taking in a deep breath as she slapped her dick against my face a few times.

"Good boy," she said. "Now, let's get rid of those clothes."

She snapped her fingers and I blinked; my clothes were gone. Vanished, into thin air, as though they had never even been there to begin with. I opened my mouth to ask what had happened, but Lilith shoved me back onto the bed and climbed on top of me. Much like in the dream, my new Demon Mistress began kissing me all over.

On my neck, my chest, my forehead and my lips. I groaned, as she sucked and licked at my nipples and took both my cock and hers in her hand and started stroking them together.

Suddenly, she grabbed me by my hips and flipped me onto my stomach. Her tits pressing down against my back and pushing me into the mattress, I could feel her cock poking at my asshole. My heart was pounding and I was panting and sweating; I wanted this. I wanted her cock in my ass...I couldn't believe the way that she was making me feel.

It was as if Lilith had some strange spell over me, like she was controlling my emotions.

Sucking on my neck, Lilith probed my hole with her cock, humping me and teasing me for a few long moments. Just when I thought she was finally about to take the plunge, Lilith climbed off of me and flipped me onto my back again.

She grabbed my head and pulled it into her lap, feeding me her huge cock once again.

Forcing my head all the way down, Lilith began fucking my mouth with a desire for one thing and one thing only; to blow her load in my mouth. She got exactly what she wanted, as her cock swelled up nice and good and with a growl, she erupted and flooded my mouth with her burning hot cum.

I choked, swallowing the best that I could and gagging a little, too.

It was thick, it was creamy and it burned going down. It tasted good though; sweet, like candy and I savored the taste, never wanting it to go away. Once I had swallowed every drop of her cum, Lilith pulled her dick from my mouth and shoved me back onto the bed and smiled down at me.

"It's a deal."

With that, she was gone. I was getting a bit tired of her just appearing and disappearing without warning and I wished, that she had of stayed a bit longer. I wanted to do so much more, then just suck her cock...my ass burned, eager to feel her deep inside of me.

What was this fucking effect that she had over me?

In any case, the deal had been made...it wouldn't take long for me to start seeing results.

Mom came home the next day and told me all about her night with Michael; as suspected, she had slept with him. Of course, she didn't straight up tell me that...but I could tell. They went out on another date a week later and another the week after that. Soon, they were going out together practically every Friday and Saturday night and I had never seen mom so happy before.

Days turned into weeks and weeks into months, and before long, mom and Michael had been dating for half a year. I had met the guy on a few occasions myself and honestly, he really was as nice as mom said he was. I also met his son, Jake, who seemed like a really decent kid himself.

Jake was about a year younger then I was and didn't seem like a very social person; that didn't change the fact that he was an alright guy though.

Just after the six month mark, Michael asked mom to move in with him; of course, she said yes right away. He also offered to let me come with her and stay there as well. Of course, I said yes too and a week later, we had both moved into what I could consider to be the biggest house, I have ever seen.

Michael must have had like six bedrooms, three bathrooms and a huge backyard and basement.

If there were a heaven, surely this was the place. Mom quit both of her jobs and took on the house wife role; she deserved it. Michael treated her like gold and that was really, all I could ask for. Lilith had really held true to her word and her end of the bargain.

Every night after the night that we made the deal, I continued dreaming about Lilith. These dreams were always so vivid, so realistic, that it felt like Lilith was actually there with me.

There was always sex, in every single one of these dreams and I always woke up covered in sweat, my boxers drenched with cum. It was starting to get out of hand now though, because I was constantly horny. If I wasn't dreaming about Lilith, I was locked in my bedroom and jerking off, any chance I could get to myself.

I was going crazy! I even wound up going out and buying a dildo, though I'm not quite proud to admit to that.

Before bed almost every night, I would strip down, shower, return to my room and pull out the nine inch dildo from it's hiding spot in the back of my closet. I would lube up, get in bed and carefully slide the large rubber dong into my tight little ass. The first time that I did it, hurt like hell but it was worth it in the end.

After a few minutes of messing around and pushing through the pain and discomfort, it wound up feeling really good. I rode the dildo good and hard, fantasizing that it was actually Lilith fucking my tight ass and I had probably the most intense orgasm of my life; it still wasn't good enough though.

I still couldn't shake the feeling, that as good as a rubber dildo felt, the real thing would feel a hundred times different...for better or for worse.

The more I thought about it, the more I realized...I didn't want to have to wait the entire ten years, just to start doing these things with Lilith. Of course, I was in no hurry to die and go to some other dimension and leave everything behind; I did really want to fuck Lilith though. Finally, I decided...I had to have her.

So, one night when my mom and Michael were out on a date together, I grabbed the book from my drawer where I had been keeping it hidden...and made my way into the basement.

For the first time in six months, I drew the chalk pentagram, set up the candles, spilled some of my own blood and summoned Lilith.

Just like the first time I had called her, I found myself sitting there and waiting impatiently for her to appear. My heart kept pounding and I was starting to wonder if maybe she wouldn't come. Maybe this spell only worked one time, for you to make a deal with her and after that, it was useless.

I sighed, not wanting to give it up just yet...

"Fancy meeting you here."

I jumped, startled by her voice and pushed myself to my feet. Spinning around on my heels, I found myself staring at Lilith who was no more then a few feet away from me.

"You do know, you only get one wish Jimmy."

"I know," I replied, nodding my head. "I just...that's not what I called you here."

"Oh? Then, what's the meaning of all of this?"

I stepped forward nervously and reached out to her, placing my hand on her hip and she looked down at my hand and back up at me. "What are you doing, boy?"

"Lilith...I um...was wondering if maybe, we could rearrange our deal? Just slightly."

"Hmm, sorry kiddo; no can do. Why would you want to do that anyway? You've got everything you wanted, right?"

"Right, of course! I didn't mean to cancel it or anything like that. What I meant was...well...what if you took me as your slave right now?"

She cocked her head and grinned, clearly surprised but not entirely against what I was suggesting. "Yes, that's right," she said softly.

"I've been watching you...I know the dirty things you've been doing. The fantasies you've been having about me, coming to your room and ravaging you...dirty, dirty boy."

"I don't know what you did to me," I said, my breath catching in my throat for a moment. "But, I can't stop thinking about you."

"That's good..."

Lilith took my hand and moved it down under her dress, just like last time. I wrapped my hand around her cock, gently stroking it and feeling it grow harder and harder in my grip.

"You want my cock, don't you boy?"

"Y-Yes Mistress."

"I know you do," she whispered. "Get on your knees."

I wasted no time, obediently dropping to my knees right in front of her. Lilith lifted her dress and her massive cock sprang free, standing fully erect. I opened my mouth and wrapped my hungry lips around her,taking her right into my throat and Lilith let out a soft, satisfied moan.

"That's good, Jimmy boy. You really love my cock, don't you?"

I gave a muffled "Mmhm" and continued sucking, attempting to deep throat but gagging and having to pull back for a moment.

I didn't wait for long before taking her again though, pushing myself to try and deep throat her again. As my mouth adjusted to her large size and my gag reflex began to relax, I found myself slowly getting better and better. Within a few moments, I was taking the entire thing and deep throating like I had been doing it for years.

Lilith was beyond satisfied with my actions, running her hands through my hair and forcing my head up and down. Then, I felt her twitch and swell up, and without any verbal warning, Lilith pumped what felt like a gallon of her cum down my throat. I had missed that taste...that sweet flavor, burning my throat as I swallowed it down.

It felt like taking a sip of very hot tea. It burns when you drink it down, but the burning sensation in your chest is almost...soothing.

When she finished, Lilith pushed me back and her cock slid out of my mouth with a loud, audible pop.

"You're such a little cock sucker, aren't you?"

"Yes Mistress," I said, staying on my knees and gazing up at her lustfully.

"You did a very good job, sucking my dick Jimmy. Do you want a reward for your good job?"

I wasn't sure what she had in mind, but I nodded my head and waited for whatever else she wanted me to do.

"Do you want me to fuck that sweet little ass of yours, since you did such a good job sucking my cock?"

"Yes Mistress, please!"

"Yes Mistress, what?"

"Yes Mistress...I want you fuck my ass, please!"

Lilith snapped her fingers and suddenly, we were no longer in the basement; we were in my room, on my bed. I was lying face down and Lilith was sitting on my legs. I could feel her huge cock against my ass crack, the hot head probing my hole as she leaned forward and kissed the back of my neck.

She whispered softly in my ear, "Are you ready to be mine?"

"Yes," I replied, panting heavily.

Lilith pushed forward and I felt the tension, from her cock pressing against my hole, straining and trying to worm it's way into me. I wasn't too tight, since I had been practicing with that dildo but the difference between the dildo and Lilith's cock, was immediately noticeable once she got the head inside. I gasped, then moaned softly and pushed my ass back against her, my hole swallowing more of her cock as I pushed back.

Impressed at my eager attitude, Lilith gave my ass a hard smack and giggled, as the sound of her hand connecting with my flesh echoed through my bedroom. She pushed forward and the rest of her cock sank into my ass, bottoming out and grabbing me by the hips.

All bets were off now. I could feel her balls pressing against me, she was so deep inside of me that it seemed impossible. Lilith pulled back about halfway and in one swift motion, she slammed right back into me again.

She repeated this, over and over again, hammering away at my ass and I was amazed to find that there was pretty much zero pain; it must have been something she was doing, to make sure it didn't hurt. Even with all the practice, I had thought for sure that it would be a little painful.

I felt Lilith's hand on the back of my head, pushing my face into the pillow and she smacked my ass again, harder this time as she rode me hard. It didn't take long, before I felt her cock start to swell up and it gave a twitch, before starting to pulsate and throb inside of me.

Lilith moaned, her hard nipples poking at my back as she continued riding my ass and started to cum.

The sensation was strange, similar to when I swallowed her cum, it burned my ass when she came inside of me. It was red hot as she pumped it deep inside of me and despite the intense heat, it was incredibly arousing. My own cock swelled up to the point where it was almost painful, before it burst and sprayed the sheets underneath of me with cum.

Lying next to her just minutes later, I stared up at the ceiling as Lilith sat on the edge of the bed and smiled down at me. My ass was still gaping, wet with her cum and I was drenched in sweat.

"So...that's what I have to look forward to, once you take my soul?"

"A whole eternity, of this big demon cock in that tight little ass."

"I think that sounds good," I said and Lilith laughed.

"You could always come with me early, if you wanted."

I thought about it for a moment, but decided against it...we had a deal and I wanted my full ten years.

"I didn't think so," Lilith said, smiling.

"Just remember though. I may have given you ten years, but that doesn't mean you'll get the whole ten; accidents do happen."

She gave me a funny look and I shuttered, wondering what exactly that meant. Before I could ask her though, Lilith had disappeared once again and I was left alone in my bed to wonder.

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  • COMMENTS
17 Comments
LeeIIILeeIIIabout 4 years ago
great story

I love this story I can't wait to see how the rest of them end up.

mrsreadermrsreaderover 5 years ago
great start

Loving the story already

BiSexFiendBiSexFiendover 7 years ago
More Chapters!!!!

This is honestly one of the best stories I've read about a demonic transexual, I hope you write more. Maybe include him eating her ass, or Lilith takes human form and they go on vacation for a day or two, the whole time she's dominating him. And show him going to hell and being her top slave and she rewards him some way. Just please please write more than 2 chapters WhiskeyIsGood.

WhiskeyIsGoodWhiskeyIsGoodover 7 years agoAuthor
Thanks everyone

I'm working on a part two right now. Don't think it's going to go any further then two chapters, though. Then again...who knows?

addyftwaddyftwover 7 years ago
Standard Whiskey Quality!

Another amazing story from Whiskey!

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