Halloween 365 Days A Year

This is a copyrighted original work by the author. All rights reserved.

All characters featured herein are at least eighteen years of age, even if not expressly stated. Any resemblance between actual persons, living or dead is entirely coincidental. Any children referred to in this are purely for story plot. Thanks, Dean.

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Here we go again. It is the 30th of October and my mom is getting costumes ready for Halloween. I don't mind it so much except for the fact that I am a 19 years old, male, and the thought to having to take my little sister and brother trick or treating and through the haunted house just grates on my nerves. Mom remarried after my father's death and started a second family of sorts. I love the kids to death but going out with them in costume is almost more than I can bear. The only saving grace is that in costume no one can see who I am.

We spent an hour chasing after candy and of course in order to keep the little twerps at bay I had to give what candy I got to them. You would think if I had to endure this I could at least keep the candy. I was ready to do something else when mom chimed in, "It's time to go to the haunted house." This was met by a chorus of cheers from the twerps and a groan from me. Mom gave me a dirty look and I yelled, "Oh yippee we are going to the haunted house." As I jumped up and down acting like a 9 year old. Again I got a look from my mother.

Maybe I would get lucky and lose them in the thing since its pitch black. I could be so lucky. Mom drove us over to the haunted house, which was held in an old school. Three floors and a basement of people yelling at you trying to get you to pee your pants and then this would be over and I could go home.

We paid at the door and started to go in with another group of people who arrived when we got there. Mom thankfully took each of the kids' hands and kept them with her. We got in and the kids screamed and yelled and mom told them it would be okay countless times and we had only started the first floor.

We got to the second floor and it started to get much more realistic. They told us it was scarier as you went and you could take the stairs at each end if you wanted to go back down and exit. Mom started to head that way and both kids screamed they wanted more. She turned and started up to the next level and of course I groaned again.

We were just getting started on the second level when someone grabbed my hand and I knew it was not my mother. All I heard was "Rob lets duck in here." I was pulled behind a curtain and into another room that was just as dark as the one we had left. I could not see who I was with and I knew my name was definitely not "Rob," but I kept my mouth shut and just held her hand.

We had just started to leave the area through the curtains when I heard someone say, "Tiffany where did you go?"

I at least knew her name but that was all I knew. Once we got into the dark room she turned to me and took off my mask and said, "Well you have been waiting for a special surprise and tonight is you lucky night. I know being away at college has been tough for both of us since it's my first year but tonight we are going to do something that we have never done before."

I just stood there and never said a word. I wanted to know what the special surprise was and talking would have given me away so I just kept looking her direction. She asked me if I was ready and I just mumbled, "uh huh," and kept looking at her. I could just finally make out where she was at but other than that it could have been a guy for all I could tell.

"Well here we go and I hope you like it."

As soon as she said it I felt the bottoms of my costume slide down my legs and then warm fingers grab my briefs and yank them to the floor. A warm hand reached out and grabbed onto my cock and began to stroke it and I fell in love. Well maybe not in love but I was well into lust by that point. When she had just gotten me hard I felt her move forward and placed her mouth on the head of my cock and her tongue swirl around the head causing me to groan. "Oh you like that do you?" she said as she pulled her lips away.

She immediately went back to sucking on my cock and stroking it into her mouth in long even strokes. She began to pick up speed and then reached through with her hand and cupped my balls before squeezing them slightly causing me to moan again. She pulled her head away and then said, "Are you ready to return the favor Rob?"

I moaned another "uh huh," as she laid back. I followed her to the floor and grabbed ahold of her skirt flipping it up and over her so that I could get to her pussy. She had nothing on under the skirt and she spread her legs apart giving me complete access to her. I almost dove into her I wanted to taste her so bad. This girl was a real wench and I wanted her all too myself if only for tonight. My mouth planted right at the center of her pussy and I stuck my tongue out as long and hard as I could make it as I moved through her slit trying to give her as much pleasure as she had given me.

I continued to plunge my tongue into her and then switched to circling her clit until she started to moan. She began to shake a little and then her legs came up and she pushed her knees together trapping my head between her thighs as she came in a shudder. It was the neatest thing I had ever witnessed in my life. I continued to push my tongue into her and then began to run it up and down her slit again. Thinking that she wanted me to put my cock into her I moved up and grabbed my cock and aimed it at her pussy. I touched her outer lips when she said, "You know I am not on the pill and we can't do that but I still have a present for you. You have been so patient waiting for me knowing that I wasn't ready yet.

I think my heart sank at hearing those words until she said, "I am ready for this."

She rolled over and stuck her ass in the air and said, "I hope my ass will do sweetheart."

My heart did a flip flop on hearing that. Will it do, will it do, this woman had to be crazy if she thought I would say no.

As I approached her she looked back over her shoulder at me in the faint light and said, "I have thought about this for weeks and tonight I decided it was going to happen. I already lubed myself so that I would be ready for you."

I placed my cock at her entrance and could feel her pucker moving in and out. I told her to push a little and then I pushed the head of my cock past her entrance as she moaned, "Oh my God that feels huge, go slow."

I did go slow as I pressed my cock into her ass. Once I was completely in she reached back under, grabbed my balls and squeezed them a little, before beginning to slowly massage her clit.

I began slowly stroking in and out of her ass and while I could not see it or her very well for that matter it felt like something I had only thought of in my dreams. Her ass was so tight and she was squeezing my cock with her ass as I stroked into her. She told me to pick up the pace and I began to pick up speed. I could just begin to feel my balls slapping her ass. I told her I could not last much longer and she said, "I want you to grab my hips and pump for all your worth till you come. Don't you dare pull out I want to feel you come in my ass."

I grabbed ahold and pumped until my cock began to spurt into her. Once I was finished I stayed in her ass until she finished fingering her clit until she came a short time later. I could feel each contraction around my cock and she finally pushed my cock out.

She didn't move right away so I massaged her back and ass until she laid forward and then said, "We better get dressed and get out of here before someone comes looking for us."

It was only then that I remembered my mother and the twerps. I hoped that my mom hadn't really missed me going through the rest of the haunted house. We dressed and started through the rest of the second floor still unable to see each other and then headed down the stairs to where they served refreshments at the end.

When we got to where everyone was at I could see my mother giving the twerps some cookies and juice and Tiffany turned to me with a smile on her face. She just looked at me and said, "I knew you not Rob from the time I grabbed your cock. Your bigger than he is and I had a great time." I just smiled at her when she said it and gave her a kiss on the cheek. My mom hollered to tell me that they were there and I looked at Tiffany again and she said, "Let me guess out with the little brother and sister." I nodded yes and she laughed.

"Mine are right over there." She pointed to three kids with their mother as we both began to laugh.

"I know this is awkward but I do have a question for you." She said as she reached into her pocket and took out a piece of paper.

"Here is my phone number and I just wanted to know if you might be interested in celebrating Halloween 365 days this year?"

"I kissed her on the cheek and then wrote down my name and number on it and gave it to her as I said, "I think Halloween just became my favorite Holiday of the year, I will call you when I get home."