Can I Watch?

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.

"Why what'd he do this time sweetie?"

"Oh because I was talking with Katie for no more than 5 minutes, his jealous ass made me clean out the janitor's closet and do inventory."

"I see....Well what if I talk with him at the party?"

"The party!? You mean he's going too!?"

"Yes he's actually one of Mr. Maven's friends on Facebook and I saw he was amongst some of the people going. He commented on it."

"Shit...."

"Come on sweetie I hope you're still going, Sheryl said you two picked out costumes and that Katie was going as well. So how about I talk with him and get him to lay off you, I am a supervisor as well."

"Mom I have to warn you though, Jason he's...."

"What a perv? I've dealt with guys like him before don't worry. After I talk with him everything will be alright. Now dinner's in the oven, go take a shower and settled down, it should be ready by then."

I gave her a hug, leaving for the shower hoping Mom could come through on her promise.

————

In the mean time college classes were kicking my ass. I had two papers due by November 5th. I'm a big procrastinator, surprise! I started a little bit on one and then would quit and switch to the other. Back and forth until all together on my day off from work school I had only a page done for each class that was due.

I decided to say screw it and masturbate instead. I loaded up my favorite Lexi Luna movie and went at it thinking I had the house to myself since Mom and Dad were at work. I had my earbuds in on my phone and must not of closed the door because as Lexi was taking a stud doggy style my sister came barging into the room.

Shit! I grabbed a blanket and tried covering myself up but my 7" erection was still apparent.

"Get the fuck out!!!" I shouted.

"Oh no need to be shy, like I haven't accidentally seen it before."

"What the fuck do you want?"

"I need cigs and you're the only one that can drive me so...."

"Give me an hour"

"An hour, wow, most guys I know only last 15 minutes. How 'bout I give you a hand?" She said as she tore the blanket off and revealed my penis.

"Wow, I knew you were hung but I've never seen it up close like this." She then wrapped her hands around my dick and stroked.

I just sat there silently as my sister began jerking me off. I was in shock.

I was getting close as I kept my eyes glued to Sheryl.

"Just tell me when you're about to cum."

I nodded nearly out of breath.

I was getting close and muttered "I'm...I'm"

Sheryl surprised me again by taking me in her mouth as I came, shooting loads down her throat.

"Done...now take me to go get cigs. Oh and by the way you taste good. Katie's a lucky girl."

My mind was buzzing as I rolled up my jeans, turned off my porn and left to take my sister up the street to the gas station for cigarettes.

————

October 31st the night of the party.

I could barely sleep the last night because I was so excited to for this "Adults Only" party at Mom's and Sheryl's boss Mr. Maven's house. I was going to see Katie and possibly get laid. Hoping to.

I put my sexy Pirate costume on. The tights fit snug so much that my junk was practically on display. I didn't want to pull a Lenny Kravitz so I put briefs on underneath. The vest was the only chest covering so I brought a hoodie with me in the car, just in case.

I stepped out of my room and headed downstairs. Sheryl was in her stewardess costume standing outside smoking a cig on the back porch. I was reminded of how she got me to get her that pack she was smoking. A cold chill ran up my spine.

I turned the corner to the family room and I saw Mom in her costume. I was stunned. She was standing up flipping through the channels on the tv dressed as a sexy Velma from Scooby-Doo! A tight orange shirt that stretched across her large breasts with an outcropping that left her breasts practically popping out and her stomach bare. She was wearing a red skirt that was way too short and loose. A wig and thick black glasses. Orange knee high socks and black clogs.

"Mom!?"

"Hey Jack Sparrow! Ready for the party?"

"Mom you need to change people I know will be there!"

"Oh hush honey, I your Father already got a good look at me and HE approves, so so should you. Everything's covered up so don't worry. You don't have a problem with Sheryl's costume, so why not mine?"

"Because your my MOTHER...You know what fine, just don't get drunk and embarrass me. Please!"

"Oh don't worry about that, but I will be imbibing because your father shouldn't be the only one having fun. I'm sure he's living it up right now as we speak."

Sheryl came in from smoking.

"Mom you taking me or what?"

"You coming with us or driving yourself sweetie?" Mom asked.

"I'll drive myself, you two will likely be getting a cab home anyway."

"Ok Sheryl, let's go, see you soon sweetie!"

——

As I arrived to the large mansion-like house there were two 10 Foot plastic skeletons in front guarding the door. The lawn decorated with smaller skeletons and headstones.

A guy dressed as Riff Raff from The Rocky Horror Picture Show answered the door. "ID pLeASe!" he said in a creepy voice. I was let in and smoke filled the air. The smell of pot was in the air and thick. Peter Pan and Harry Potter were on the couch smoking a bong. There was a sexy school girl, a shirtless male Angel, two hot nuns, Cleopatra and so much more. I found Mr. Maven a short fat man dressed as the Godfather. I gave him a hands shake and asked him where my Mom, Sheryl and Katie were.

"You're Mom's out by the pool, Sheryl's upstairs and I don't know who Katie is son."

I politely bowed down and kissed his large ring.

I went outside by the pool and found Mom talking with Darth Vader. Mom was drinking from a red solo cup and she appeared fine. Nodding her head and smiling. I went upstairs to find Sheryl to see if she'd seen Katie.

I opened one door: Mickey Mouse and Little Bo Peep were fucking on a bed missionary style.

I tried the next room: No one.

The next room: Sheryl was sitting on the bed making out with Brian; Mr. Maven's son who was dressed like a cop.

"Hey real quick Sis, you seen Katie anywhere? "

"Next room bro"

I quickly ran to the next room. The room was empty but it had an attached bathroom with the door open.

I found Katie dressed as a schoolgirl passed out in the tub next to a bottle of vodka. No sign of foul play. I checked her pulse. Fine, just sleeping. Suddenly I heard voices come into the room. It was Mom and Darth Vader. They sat on the the bed.

"See he's a good boy, could you just lay off of him. He works hard and has been struggling with college recently..."

"I could if you have something to offer"

What was this? Who is she talking to?

"I do."

Mom then tore off her orange shirt leaving her in just her bra. She then reached behind and unclasped her bra leaving her tits bare. I was shocked. They were so huge with tiny areola and pointing hard nipples.

"You can feel them if you want."

Vader reached out with his long black gloves and fondled each breast.

"Lick them baby" Mom said.

Darth Vader then removed his mask only to find out that in shock it was Jason!

I wanted storm into the room and beat the shit out of him but I was hard as a rock. My hand betrayed me as it started stroking my dick.

Mom then reached out and grabbed ahold of his pants and pulled them down revealing his penis. It was six inches but thicker than mine. She started stroking him as Jason continued fondling my Mom's tits. Jason then let go as Mom bent forward taking him in her mouth and started bobbing.

After 15 minutes Mom's mouth let go of Jason's penis with a pop.

She lifted her skirt revealing a red pair of lace panties and pulled them down then off, flinging them at him with a laugh.

"Ready to return the favor?" She asked.

Jason just nodded and got between her legs, licking her pussy up and down. When Jason found her clit Mom yelped.

"Oooh fuck Jason, lick it and suck my clit!"

Her head tilted back and her eyes rolled to the back of her head. Her body shook and face went flush.

Mom then got up and reached out for her panties, but Jason shook his finger at her.

"This isn't over yet, get on your hands and knees."

"No wait....We've done too much already, isn't that enough?"

"You want Allen fired? I can get him fired. Then I can I tell him his Mom sucked my dick."

"No I don't want him fired....Just, just pull out when you're ready"

With that she got on her hands and knees. I saw my Mom's trimmed pussy in all it's glory. I took out my cock and kept stroking. To my surprise though another hand grasped it! I looked down to see Katie who had her finger to her mouth in a "shush" gesture.

Jason then lined his cock up and slammed into my Mom with one thrust. Her scream was deafened by the music outside.

He began thrusting like a piston into her. Her breasts swinging like a pendulum.

Katie then began sucking on my dick. I was in heaven and hell at the same time. I was watching the girl I've been admiring for a year suck my dick while the boss from hell was screwing my mother.

"Fuck you're tight, tell me how much you love my cock bitch!"

"Uhhhh fuck! I love you're fucking cock Jason, fuck me hard!"

Holy shit! Was my Mom enjoying this asshole?

Katie then got up out of the tub and got on her hands and knees. She peeped out the door along with me.

"Holy shit that's Jason." She whispered

"He's hung but not like you...Lift up my skirt and pull my panties down, I want you to fuck me."

Allen needed no further instruction. He lined his penis up with her pussy and entered his first vagina. It was tight, wet and overwhelmingly warm. It was pure heaven. He went slow at first and then began ramping up his thrusts as Jason started smacking his Mom's ass in the room.

"Fuck me, fuck me Jason! You're so much better than my husband!"

"Mmmm that's it Allen, now reach under me and rub my clit."

After trying to find it, Katie guided his hand to it and he began rubbing frantically.

"Oh yes Jason! Fuck me! Fuck me and spank me!

*Smack* *Smack* *Smack*

"Fuck me harder!" Katie said

"Who's that!?" Allen's Mom asked

"Who cares I'm almost there bitch."

"Aweeee shiiiiiiiiit!" His Mom's muscles contracted and spasmed around Jason's cock as Jason grunted.

"Take it! I'm cumming!" Jason said as he unloaded into my Mom.

"No! I told you to pull out!" She said trying to push Jason's cum out to no avail.

Allen slammed harder into Katie, grabbing her breasts.

"That's it squeeze them hard....oh god I'm cumming Allen!"

Her pussy grabbed and clamped down on my dick hard, causing me to lose control and cum deep inside her. Spurting rope after rope into her womb. My Dick then slipped from Katie's pussy.

"Allen!?" Mom said looking at us looking at them through the door. Jason walked over and opened the door, exposing us.

"I see you've had yourself a good time"

I got up and swung at Jason landing a shot on his chin that sent back to the floor. I got on top of Jason and began punching him relentlessly.

"I quit and if you ever come near Katie or my mother again I'll fucking KILL YOU!"

"Allen....I'm so sorry" Mom was muttering.

"Don't."

"Allen was that you're Mom? That was so hot. Jason, leave already!!! Read the room!"

Jason pulled up his pants crying and scurrying out of the room.

"Mrs..."

"Diana" Mom replied.

"Mrs. Diana that was so hot, you're so beautiful. I mean it's a shame that it was with Jason but you fuck like a champ"

"Why didn't you stop him Allen?" Mom said crying.

"He was too busy attending to me, isn't that right Allen?" Katie said with a wink.

"Yes and you seemed like you sure were liking it."

"Look Allen, you're Dad, he's been cheating on me...For a while now, I found the texts and pictures on his phone."

"So this was a revenge fuck?"

"No this was to help you out with Jason sweetie. I didn't think it'd go this far."