My Halloween Fairy

Another in my fantasy genre, same premise as my Easter Bunny and Cupid stories but a requested Halloween version. Hope you enjoy! Brief mention of anal but not included.

Halloween was fast approaching and decorations were going up everywhere. It was my favorite holiday of them all, mostly for the wonderfully slutty costumes the girls would wear for their parties. My sister, Amber, had a few friends that would hang out with her, pre gaming with whatever cheap liquor they could swipe before heading to whoever had a free house that year. I had just turned 19, my sister was only 20 so wasn't legally allowed to drink but it never stopped her. Our parents were gone for the long weekend, they were going to a friend's lake house for their annual party. Amber and I suspected our parents were swingers but it was something we never spoke about and just carried on with our lives.

As for me? I didn't have a lot of friends really. I was really into my horror and sci-fi movies, didn't work out beyond my cycling everywhere and got really shy around people, especially women. I was pretty sure I'd be that 35-year-old virgin working at the video store if they hadn't all vanished in favor of streaming but I didn't care too much. I also had a pretty unhealthy obsession with Amber. She definitely lucked out when it came to looks. She was taller that most girls, amazing breasts that just complimented her slim body and guys would melt when she smiled, her pretty face and bright blue eyes seeming to mesmerize them. I may be exaggerating but to me she was the goddess who I'd likely compare beauty to and probably one of the reasons I was single. She had caught me trying to spy on her more than once so our relationship wasn't cozy. I know she loved me though, she was fiercely protective of me and wouldn't let anyone pick on me at school or our technical college we were both going to.

I was sitting watching porn, getting ready to jerk off one afternoon when she knocked on my door. I quickly minimized my windows and hid the secret picture of her in a bikini I had and said she could come in. She looked at me like she knew what I was doing, pretty sure she was suppressing an eye roll but didn't say anything.

"Hey, Zelda got out, can you help me find her please?" she asked me.

"Again, thought Dad fixed the fence?" I replied.

"He did but the delivery guy forgot to latch the gate. Please, it's getting late and she hates the dark."

"Fine."

Zelda was my sister's toy poodle. It was the only thing I didn't like about her. She loved that dog more than anything and it only liked her. No matter how nice I was or how hard anyone else in the family tried, it hated anyone that wasn't Amber. I got up and put sneakers on, she knew I'd never refuse her anything and we set out looking for her.

"Are you sure you saw her go in there?" said Amber. A kid said he saw the dog go into an old house.

"Yea, pink collar with a bow on the front. She looked pretty scared but wouldn't come to me," he replied.

"Okay, thank you."

The old house was one all the neighborhood kids feared. Stories of long-ago murders and bodies in the basement circulated but in reality, it was just a neglected Victorian style house that nobody wanted to buy. The door was long gone, our town never had a problem with homeless or junkies but it was unsafe and people just knew to stay away. Amber didn't care, she needed her dog.

"Are you coming in with me?" she asked, already headed to the door.

"Of course, the stories are all bullshit," I replied.

"Well, use your phone's flashlight and be careful."

We split up when we got inside. With the windows all boarded up and the sun starting to set, it was pretty dark inside and we made our way in. The bare wooden floors creaked as we walked over them, calling the dog's name then listening for any sounds. I heard a noise coming from the basement and looked down, darker than anything and scary as hell looking of course. I made sure I had enough battery to sustain my phone's light and gingerly made my way down the steps, calling the dog as I went.

I don't remember falling. I had one hand on the rail and my phone in the other hand but I woke up and my phone was in pieces beside me and the dog was cowering in the corner, just looking at me as it shivered. I tried to sit up but everything hurt.

"Easy now, you're in a bad way," said the voice.

I couldn't see who spoke. The voice was soft like you'd imagine from an Angel.

"Wh... who's there?" I replied.

"I can show you but you shouldn't be afraid, I promise I won't hurt you."

"O... Okay."

A hand came out of the darkness holding something that lit up the basement. The dog whimpered but stayed put and I'm pretty sure I pissed my pants. From the corner a creature came towards me, I couldn't move so I couldn't run anyway but I was terrified. It was at least 7 feet tall, large claw hands like all the movie werewolves and its wolf looking face barely able to hide all the razor-sharp looking teeth. It got close to me and sat down, I prepared myself for the end.

"I'm sorry, I know I look scary but this isn't my true form. I was punished for using my powers innapropriately and have to stay this way until I can complete my task," it said.

"Wh... what are you?" I asked.

"Hmm, closest thing to your reality, a fairy. I can tell you more but you're really hurt. I've paused time to let us talk but if I don't help you, I'm not sure you'll make it out of here."

"Are you going to eat me?"

"No, we don't eat the same way humans do." it said with a laugh.

"Wh... what do you want from me?"

"Do I have permission to help you? Helping you doubles my quota but you're a good kid. I see how much you care about people; how happy you make your Grandma with your weekly visits and you don't feel hate to anyone. That's pretty rare, especially how most treat you. Ooh, I see how much you care about Amber, naughty boy," it said, smiling to reveal even more sharp teeth.

"Wh.. what do I have to do?"

"Let me help you, just say you give permission. In return, all I need is one hundred orgasms caused by you. And no, jerking off won't do before you ask, I know how often you spank it."

"Y.. you can read my mind?"

"Yes, how else would I know about that bikini picture. Amber does look pretty sexy in that one but she's your sister."

"I'm a virgin, how am I going to do that?"

"You also can't get past Amber can you. Fine, do you want it to be her?"

"Y... yes."

"Then give me permission."

"There's no way she'd let me touch her, never mind let me give her an orgasm."

"Leave that to me."

"Marcus!!" screamed Amber.

"Stay where you are, the stairs there are not safe," said the fairy. It's voice had changed to a deeper and menacing one.

"Who are you?" replied Amber.

"I can help him but my help comes with a price. He won't make it without me."

"I can't even see you, who the fuck are you?"

"Try not to scream."

The fairy stepped into the light and Amber just sucked in her breath.

"You can save him? He's bleeding pretty badly."

"I can. He's agreed to my price but you have to be the one. He has to cause 100 orgasms, the energy caused by them from my magic will help me regain my true form and return to my own realm."

"I'll do whatever you want, yes I agree."

"Good."

I don't recall blacking out again but I was being tended to by a firefighter. He was checking me for serious injury as another was setting up a stretcher on a pulley they'd set up.

"You're okay kid, pretty nasty bump on the head and a few scratches but you'll live. Hand me the dog, I'll pass it up to your sister," he said to me.

I didn't realize I was holding Zelda, she was just looking up at me, shaking.

The firefighters put me on the stretcher then I was lifted up to the ground floor. Amber was waiting outside, she had tears running down her face and came running over to me.

"He's okay ma'am, a few superficial cuts and a bump on the head but he'll be fine. He may have a concussion so I want to take him to hospital," said the firefighter.

"Of course. I'll take the dog home and come to you," she said to me.

They drove me to the hospital where I was checked over. They said I had a mild concussion and wanted to keep me overnight but I was otherwise fine. A Police officer came to talk to me, asked about the house but was satisfied with my explanation that I'd went in with Amber to get the dog. She came to see me after he'd left.

"I couldn't get a hold of Mom or Dad, are you okay?" she said to me, a look of concern on her face.

"I've felt better but these drugs they gave me are fun. What happened?" I replied.

"You fell through the stairs. I could see you but it looked pretty dangerous so they sent rescue down. They boarded up the door, they need to tear that place down."

"I didn't imagine it right?"

"What do you mean?"

"The thing that helped me."

Amber looked at me and didn't say anything for what felt like forever.

"I thought I imagined it," she said quietly.

"Don't worry, I won't show myself but I'm very real. I had to fix him up but he had a big splinter right through his ribs, a cut on his neck that barely missed the jugular but was still losing a lot of blood and wouldn't have made it despite how fast the Firefighters got there," said the voice.

The tv clicked on and it was a view of the basement. My broken body was being brought up through the broken stairs and Amber was standing watching, screaming and being held back. She turned the tv off.

"So, I... I have to cum 100 times with him to repay you?" asked Amber.

"Yes."

Amber looked at me, looked into my eyes.

"Okay."

I was discharged from the hospital the next morning. Amber was waiting for me in her car and we drove home quietly. I took a shower but I felt really good and was even shocked when Zelda came to see me with her tail wagging when I forgot to close my door. She jumped onto my bed and was letting me pet her, something I'd get a quick bite for before.

"Little traitor!" said Amber as she walked into my room.

"Did you drug her or something? She never lets anyone pet her but you," I said.

"I'm guessing she's grateful for her rescue."

"Well, I'm not trying to steal her. I've always been nice to her."

"Do you want to get started?"

I wondered what she meant for a minute until I notice what she was wearing. She had on a pretty pink negligee that looked spectacular on her. I could see her lacy bra and white panties she had on underneath it. I could feel my cock getting hard.

"A... are you sure?" I asked.

"You're my brother and this is wrong in so many ways but you saw the tv, we both did. We don't have to fall in love, just make me cum and go about our day until I've had 100," she replied.

I could feel my heart pounding in my chest. She had me lay back on the bed after dropping my towel to the floor and stepped out of her panties. She looked down at my already hard cock and smiled.

"That from me just in lingerie?" she said.

"Y.. yes. You're really beautiful," I stammered.

"I'm still your sister. You are not small, are you," she said, gently touching my cock.

I couldn't think of anything to say, I was worried I'd ruin the moment. Amber got onto the bed and straddled me. She looked down at me then rubbed herself before taking my cock in her hand and placed it at the entrance of her pussy. I looked up at her pretty face and gasped as she lowered herself onto me, breathing harder as I inched inside her with her thrusts. She stopped for a second when she was resting on my balls then began to slowly ride me. I was in heaven. I'd dreamed and imagined what it would be like for the first time. Feeling her warmth, her tight pussy glide over my cock with her juices felt amazing and before she really got into a rhythm I groaned and pushed up as my cock exploded, swelling as I sprayed my seed into her. She gasped then took me up to the hilt as I shuddered then smiled at me when I was finally spent.

"That was a lot of cum, little brother. Was this your first time?" she said.

"Y... yes. I'm sorry," I replied.

"For what?"

"N... not making you cum."

"If I'd known it was your first time, I'd have blown you or something first but it's okay, we have all morning. Let me clean up and we can try again."

Amber got off me and let my still hard cock flop against my stomach. She went into my bathroom and came out a few minutes later with a damp cloth for me that she used to clean my cock. She'd stripped off too, I watched her breasts shake with her every move and I was soon throbbing hard again.

"You like these don't you. I figured it would help you get it up again," she said.

She got onto the bed again and got onto all fours and looked at me with a smile. I got behind her and eagerly pushed my cock into her again and was soon thrusting deep into her.

"M... Marcus. Stop honey," she said to me.

"Am I doing it wrong?" I replied, I was horrified.

"No, let's start over okay. I want us both to enjoy this but you need to relax."

Amber had me lay down beside her and held me.

"Hey, don't be sad, I should have slowed down. The more relaxed I am, the more I'll cum. Touch me," she said.

Amber laid on her back and smiled at me as I put my hand on her. I was shaking and just rubbed her stomach but she giggled and moved my hand to her breast. She took her time with me and showed me how to fondle her breast then led my hand down to her pussy. I was still shaking but she showed me how to finger her and had her breathing heavily as I rubbed her clit.

"Okay, now get on top of me, take your time," she said.

I did as she said and slowly pushed my cock inside her again. It felt as wonderful as the first time and with her guidance, I was giving her slow and deep thrusts. Her breathing got heavier again and watching her facial expressions change as I increased my pace was amazing.

"Th.. that's it, right there baby.... FFFFUUUUUUCCCKKKKKKKK," she yelled when she climaxed.

I kept thrusting and felt her nails dig into my back as she writhed beneath me. I felt the tingling in my balls again and after a few more thrusts, I came too and sprayed what seed I had left inside her. I stayed inside her until I was spent then rolled off her as we both caught our breath. She smiled and touched my face.

"See, didn't that feel better?" she said to me.

"It felt amazing," I replied, grinning.

"My ex didn't like to be told what to do, that's the first time I've cum without rubbing myself while he fucked me."

"I don't mind being told what to do, I'll do anything you want."

Amber looked at me.

"Honey, I want you to enjoy this. It's pretty mandatory that I do but don't get attached. I'm your sister, I made a deal to save you and this is our price. I'll teach you and help you find a sweet girlfriend but when we're done, we won't do this again, okay?" she said, softly.

"Okay," I replied.

"Fuck, I'm sorry, your face looks like I just dumped you. I just don't want you getting hurt. Your first time is special, I get it but don't be following me round like a puppy. Outside this room we are just siblings again."

Amber kissed me on the cheek then got up from my bed. She got her clothes from the bathroom then left me alone. I couldn't help grinning, I had finally made love to a woman and I felt amazing. I probably spent the rest of the day smiling too, Amber went to see her friend but came back at dinner time with takeout food. She laughed when she caught me gazing at her.

"Have you had that grin on your face all day?" she said.

"Probably, I'm pretty happy," I replied.

"Well good, after dinner we can go again, I'll teach you how to eat my pussy."

I probably inhaled the rest of my food, Amber laughed when I got the hiccups but she took me to my room and closed the door behind us. She pulled up my laptop and had me go to a site and searched for lesbian porn. After scrolling a little she found a video and watched it with me.

"All women are different but this one shows the general idea. Explore with your tongue, listen to the woman's moans and enjoy it. You felt my clit when you fingered me this morning, right?"

"Yes," I replied.

"Well, don't just go straight for it. When I'm aroused it will get more prominent but the area around it feels good too."

We stripped off again and seeing her naked had me hard in seconds. She laid back on the bed and opened her legs, I got between them and gazed at her shaven pussy.

"Explore me remember. Start at my breasts, I know you love them. Get me relaxed and aroused," she said softly.

I did as she asked. I wanted to just slide deep into her and keep going until I was sore but she was right, I still had over 90 climaxes to give her and I was in no rush to be done. I kissed her neck then kissed a trial down her body. I licked and sucked one nipple while I sucked the other then when I'd sucked both I kissed my way down her body again. Facing her pussy for the first time was amazing. She was already a little wet but I took queues from the video and licked and explored her, tasting her juices and listening to her moans. When her breathing got pretty heavy, I focused on her clit and rasped it with my tongue and only stopped when she'd cum a second time.

"Th.. That was good. You can fuck me now," she said with a grin.

I placed my cock at the entrance of her pussy then pushed inside her. She felt so good and I soon worked up a nice pace, pushing deep inside with each thrust. I lost count of how many times she came for me. I was a little sore from our morning session but with her legs wrapped round my waist and my balls slapping against her ass, I groaned as I climaxed, spraying my cum deep inside her. She grabbed my face and kissed me on the lips after I rolled off her then went to the bathroom.

I expected her to just leave but she put on her panties and climbed back onto the bed with me.

"I fucking enjoyed that. Your cock is really nice," she said to me.

"I enjoyed it too," I replied.

She snuggled close to me and laid her head on my chest, after a few minutes she fell asleep. I looked down at her body and felt my cock getting hard again but I just enjoyed her closeness and dozed off myself.

I wasn't sure how long I was asleep. When I woke up, Amber was already riding me.

"Y... you were out cold, I just had to lick you a little and you got hard," she said.

She rode me until she came a couple of times then got onto all fours.

"Remember, make me enjoy it my love," she said, looking back at me.

I held on to her slim waist as I pushed inside her again. I managed to make her cum before I climaxed again, I'm sure I didn't spray much in her but I loved that position.

We slept in the same bed that night. We'd wake up, have sex then fall asleep again and I loved it. Her friend was due round the next day though, we had one more session of me eating her then doggy then she got in the shower.

"We shall continue this tonight," she said with a smile then left my room.

When my fairy appeared a few hours later, I about jumped out my skin.

"I'm sorry, I forgot to ask you both not to tell anyone about me. Ooooh, too late, Look," she said.

I could see into Amber's room as If I was there.

"No way, you only get that glow when you've been really fucked hard. You dumped Josh, he never got you there anyways. Who's the new guy?" said her friend.

"I'm telling you, I just masturbated. I was in a mood," replied Amber.

"Amber, we've fucked remember. I know what your masturbated afterglow looks like and I know what your, 'I just got railed by a stud for two hours' face looks like too."

"It doesn't matter, if you could just drop it?"

"No, I tell you everything. You tell me everything, it's our rules."

"Well, this is different."