All characters engaging in sex are 18+
This story is fiction.
*
Halloween. For me it's the best time of the year. I love the decorations, I love the days becoming cooler, I love the haunted houses and I love the parties. Not to mention that it's a given that there WILL be women dressed in slutty costumes at some point. Don't get me wrong I'll miss the warm weather, the bikini clad women, swimming and longer days of summer...but Halloween season is my favorite.
In case you were wondering my name is Allen. I'm 18 and I started community college recently because I'm a lousy student and I couldn't get into any Universities. I work part-time as a grocery clerk and unfortunately I lost most of my friends after graduation. They went their separate ways to different colleges while I stayed back. I still talk to them as they regale about their university adventures on campus. They're all getting laid. I'm still a virgin. I had my dick sucked once but that was the closet I got.
I've currently got my eyes on Katie, a dirty blonde with hazel eyes and the whitest smile. She's 24 and works as a Full-Time deli clerk along with a Part-Time job at a nail salon to pay the rent. She's got medium sized breasts that are still a handful but her real feature is her ass. When she leaves my eyes can't help but stay glued to it. I just want to rub my hands all over it. Fat chance she's interested in me despite us talking and goofing off when possible. One day I'll have the courage to ask her out.
I hate work sometimes because my supervisor; Jason is a real jackass. He's 25 with a bachelor's degree in business management. My major is history, a "useless" degree according to him. His Father is district manager and he gets special treatment. He loves giving me and everyone extra tasks to do before the end our shifts. I work Part-Time. He treats me like I get Full-Time benefits and I want this to be my career. I'll only be here through college and then from there who knows but it certainly won't be working for him. He's also a creepy perv who's been eyeing up Katie despite her telling me she feels uncomfortable around him. He's just one of those guys who gets off on power.
I live at home with my Mom and Dad; Diana and Matthew. Dad works as a representative for a liquor company in the city. He has to travel a lot for his job but manages to bring back gifts whenever possible for me and my older sister Sheryl. He's tall with greying hair. Reminiscent of Ty Burrell of Modern Family.
Mom works as a manager at a crafts supplies store in town. She's got long dark hair and fills out quite nicely due to the fact that she's into fitness. She's my height at 6 feet. She used to be heavier when I was younger, but after my Dad went on a diet and exercise routine, Mom followed suite not wanting to lose Dad to a younger woman I guess. My friends would chastise me in middle and high school over my "MILF" mom. Her bra says "38 D" and her ass is quite big and "juicy" according to them. To me she's just Mom.
Sheryl had a rough time in High School after being bullied through graduation. She too attended Community College to get her degree in English Literature but dropped out because she got into abusing amphetamines. She went into rehab, got clean allegedly. She works with Mom at the store Full-Time. Mom and Dad are giving her a year to get straight. She's 5'8 with short dark hair, kinda looks the Bond girl from License To Kill. She's always telling me to get contact lenses, that I'll get more girls without glasses. I can't put my fingers in my eyes. Ew.
It was the 14th of October, a Saturday and I had just come from a morning shift and I was bored. Mom and Dad were gone on a trip out of state to shop and Sheryl was home because she doesn't drive. Mom takes her to work.
"Why you so down?" said Sheryl
"Katie and I got caught talking so Jason made me clean the men's bathroom. He's such an asshole. Oh and I've got nothing else to do now that I'm home. So aside from a shitty day I'm now bored." I replied.
"Well I know what we could do bro. We should go pick out costumes for the party."
"What party?" I questioned.
"My boss is throwing a party on Halloween, it's ADULTS ONLY!"
"Mr. Maven? Isn't he 50?"
"Yes but he's divorced and lonely, plus his son is coming back from his trip to Europe for it. I think I might fuck him."
"You would. And who is taking you, Ms. Car-less? You walking?"
"No dumbass me and Mom are going!"
"Mom? What about Dad?"
"Another trip, this time to Vegas."
"Why can't he take Mom?"
"Mom can't take time off, the trip to Vegas is two weeks long because something about visiting a new plant, blah blah boring blah."
"I'm sure Mom's jealous."
"Oooooh she is dude. Very jealous."
"So why am I going?" I asked her.
"You AND Katie are dumbass."
"We are?"
"Yes, she already said she was on Facebook dumbass." She said as her eyes rolled.
"Awesome! We've got to go get costumes now before they sell out."
Me and Sheryl hopped in my truck and drove to the Costume Store that used to be a Lazy Boy store.
—————
As we walked in the store me and Sheryl played with the giant decorations and took selfies with them because "why not" we're still young and stupid.
Then we focused on picking out costumes.
I chose a blow up T Rex suit and showed it to Sheryl.
"Dumbass, NO!"
"Why Sis, it's hilarious."
She then came closer and whispered: "How are you supposed to fuck Katie in a blow up costume?"
She was right. At the very least I wanted to kiss and make out with her. I couldn't do that in that costume.
"Got any suggestions?"
"Sexy pirate."
"What!?"
"You've already look a bit like Johnny Depp when you take those stupid glasses off."
She was holding up an outfit with just a vest, brown tights, belt, boots, a fake goatee and a headband with built in dreads. There was a plastic sword to the right of the costume to go along with it.
"What are you going as then?"
"Give me ten minutes to change and I'll show you!"
I waited outside the changing room for twenty minutes getting irritated. Then the door clicked and she brazenly walked out in her costume. Both me and the older woman working the register had our jaws on the floor. It was a sexy stewardess costume with a gap in the outfit between her ample breasts showing off major cleavage and the skirt portion of the outfit barely covered her crotch and ass. She wore high heels and topped of the costume with a vintage stewardess cap.
I never really thought of my older sister as sexy until this moment. I have to admit a bulge was starting to form in my jeans.
"So...What do ya think LITTLE BROTHER?"
"Well if you're looking to get pregnant and make me an Uncle...."
"Oh shut up, you know I look hot. Mr. Maven's stud of a son won't know what hit him. Going to let him join the mile-"
"I get it sis! Let's just buy our costumes and leave before anyone else comes in the store."
"Mom look!" a little boy entered the store and pointed at Sheryl. The mother quickly covered his eyes. Sheryl sucked in the dressing room and luckily got changed.
We paid and left the store with our sexy and super slutty outfits in hand.
————
"Fuck him!"
"Wha-What!?" My mother said as I walked through the front door, back from work.
She was in a blue robe that came down to just below her cheeks. I don't know if she had anything else on underneath as clearly she had gotten out of the shower given her hair was still wet.
"Oh it's just work Mom, Jason is giving me problems again. Why can't I have a little conversation with Katie while we're both free and not get punished for it?"
I sat down on the couch next to Mom as she began rubbing my back.
