NOTE 1: This is a Halloween 2011 Contest Entry so please vote!
NOTE 2: A special thanks goes to Estragon for his copy editing work! A massive rewrite occurred in Dec 2018 by Tex Beethoven.
Until I began reading stories on Literotica I had no idea how many sons had fantasies… or sometimes even realities… of having sex with their Mother. I mean it isn’t really a conversation one has with his buddies. Imagine this:
“Dude, you know who I would really like to fuck?”
“Anyone who moves, I imagine.”
“True. But do you know who is the most constant late-night focus of my daily stroke-fest sessions?”
“Beth, the head cheerleader?”
“She’s in the top five, no doubt.”
“Well, who would be number one then?”
“Promise you won’t judge?”
“No, you do some crazy shit; so do I.”
“Seriously, this is really embarrassing.”
“Fine, I promise not to ridicule you too badly.”
“That’s not so bad. I was expecting Big Bertha or Old Woman Burgess. First, your Mom is ridiculously hot and second, I’ve stroked about my Mom lots of times.”
“Of course, and my Mom is nowhere as hot as your Mom.”
“So it doesn’t make me a freak?”
“Oh, it makes you a freak all right. It even makes you a perverted little freak. But hey, at our age every guy is a perverted little freak. Christ, even Hamlet was supposed to have a thing for his Mother. Remember the Ophelia song? ‘Ah, ah, when I was young, I, I should’ve known better.’ He’s got to be singing about his Mom!”
Anyway the point is simple. The older I got the more obsessed I became with the thought of sleeping with my Mother. My fantasies shifted from cheerleaders and hot blondes to my forty-three-year-old, blue-eyed, chestnut-brown-haired Mother with the big tits.
As far as calming me down she wasn’t any help, either. She was a real estate agent and always dressed in skirts, hose and heels. All three of which had become fetishes of mine, probably because I’d grown up seeing them worn on the hottest woman I knew. I was sixteen when I started giving my Mom foot massages after a hard day at work. She always kept her stockings on and my cock always rose whenever her stocking-clad legs were resting on my lap. She had to know what it was doing to me, but she never let on and it never progressed any further than a son giving his Mother a respectful foot massage, at least not outside my own fevered brain.
Mom knew she was still hot. She flirted with my friends and loved the compliments they threw back at her. She was a MILF and she knew it, she even revelled in it. That said, I never thought I’d ever have the chance to do more than just her feet…but then that Halloween happened.
Every Halloween my parents would get dressed up as a sexy matching couple and go to some big party. (Mom was sexy anyway, speaking as a hetero guy I don’t think there’s anything a man can do to look sexy.) Every year I could see their excitement growing for the big day; Mom’s creative juices always came alive for Halloween. She always designed and made the two costumes, often starting months in advance. I can’t recall all the outfits but do remember a few recent ones: Bonnie and Clyde with Mom dressed as a hot flapper (Mom looked stunning in fishnets and the cute bob haircut with her toy tommy gun and an evil grin ready to shoot someone’s balls off), Fred and Wilma Flintstone, which had my dick thinking Bam Bam all night (Mom as Wilma with her tattered neck- and hemlines with almost a nipple and almost her naughty bits showing was memorialised in a photo still hidden under my bed for stroke sessions), her fifties icons Marilyn Monroe and James Dean (which I also have a picture of hidden for play time), and last year she was Princess Leia while Dad was Luke Skywalker (her diaphanous, almost transparent white dress with no underwear that year kept my light sabre erect for months). This year they were going as Beauty and the Beast. As always, Mom refused to reveal her costume to anyone until Halloween Eve, if that phrase isn’t redundant.
I have always been a believer in whichever you like to call it… destiny or fate. And it could only have been through destiny that the dominos could have tumbled the way they did…giving me the perfect opportunity to fuck my Mother and live to tell the tale (to you, I don’t kiss and go around shooting my mouth off). First off, my Dad phoned at five o’clock to tell Mom that due to some late bargaining (Dad is a high-powered mediator…the guy you hire to negotiate the ends of long-standing feuds), he wasn’t going to make it home in time, although he might get in early enough to join her at the party later. Mom was furious, because this was the night she always looked forward to, and had put hours upon hours into making the costumes perfect for. Although she was mad at Dad, she still planned to stomp out the door and attend the party and make the best of things she could.
A couple hours later, seven o’clock, Mom came downstairs in her Belle costume, making my cock want to be her guest (id you know that song)
I’ve always secretly thought Belle was the hottest cartoon character, in the same way I think Betty is easily the hottest Archie girl. But seeing my Mom dressed as Belle, in an off-shoulder blue peasant dress displaying a generous expanse of her flawless upper chest, although nothing quite illegal if she remained upright, her hair exactly the same shade as Belle’s, plus wearing the darkest brown pantyhose I’ve ever seen other than on Hooters waitresses, was the sexiest moment of my young life.
I did what I always did when talking to my Mom. I complimented her. “Wow Mom, you could be the real-life Belle. This is your best costume yet!”
“You think so?” she asked, smiling and posing seductively.
“I know so. Dad would have loved it.”
My Mom’s smile faded. “I can’t believe he ditched me for a transportation union of all things.”
“I’m sure he’ll make it back soon.”
She shrugged and snorted, “He’d better!’ but then relented and told me, “But it’s not your fault honey, it was sweet of you to say that.” She gave me a kiss on the cheek and let me kiss hers like she always did and was off, leaving me standing there in a cloud of testosterone.
All the stars were lined up perfectly, even though I didn’t know that. Even the fact I was home in the first place was because of a string of fateful moments. Usually after seeing my parents off (not ever wanting to miss how my Mom would look that year) I would usually leave for a Halloween party as well, but this year I just didn’t feel like it. I’d been dumped a couple weeks before by my girlfriend of eight months Pamela and didn’t really want to see her there. So I was watching Halloween for the umpteenth time when the phone rang again.
“Is your Mom still home?” Dad asked nervously.
“She left an hour ago,” I replied.
“Shit,” he swore, “was she mad?”
“Think PMS cubed and you may be close,” I warned.
“Double shit,” he cursed, “I tried her cell and she didn’t answer.”
I walked into the kitchen and saw it sitting in the charger. “She couldn’t. It’s right here being charged.”
“Triple shit,” he swore, knowing he was indeed wading in deep shit. After a pause, “Well, can you leave her a note? This is going to be an all-nighter.”
“Shit,” I parroted, which got me a nervous chuckle from Dad.
Mom was sexy and caring, but you never wanted to get on her bad side.
“I’d better get her some flowers,” he rationalized. I noticed an address on a pad of paper in my Mom’s handwriting and assumed that was to tell Dad where she was.
“Better get her a whole garden. This year’s costume was her best yet!”
We said our goodbyes and I returned to watching TV. About ten minutes later, a light bulb flickered on in my head. A few seconds after that and the bulb was shining bright as the sun!
I dashed upstairs and into my parents’ room. Laid out on the bed was Dad’s Beast costume.
I stripped to my undershorts and put it on and was pleased at how comfortable it was. My Mom had thought of everything as it even had two battery-powered mini-fans in it to keep the beast inside the Beast cool. I also noticed she’d created a Velcro opening at the privates so Dad… no, so I… could take a piss without removing the costume. I looked in the mirror through a mask that was covering my entire head (with cut-outs for my eyes and ears, the ear holes covered by long Beast-hair). No one would have a clue it was me. I was the same height as my father; I had the same blue eyes as my father; I even had the same voice as my father. I went downstairs, grabbed the address, jumped into Dad’s Mercedes (the first thing a good negotiator negotiates is his fee) and sped off to the party.
I arrived at the party a few minutes after nine-thirty and was met at the door by the hostess of the party Gloria, dressed in a Snow White costume improved by a deep scoop neckline. Her face brightened when she saw me. In her usual giddy voice she said, “If Alexis is Belle, you must be Ted. Thank God you’re here, Alexis is really mad at you!”
“I know,” I acknowledged, “That’s why I hightailed it over here as soon as I got home.”
“She’s had a few glasses of wine and you know how she gets when she’s into her wine,” she warned me with a wink.
Thinking about the few times I’ve seen my Mom intoxicated, usually on New Year’s Eve, I recalled my Mom being extra touchy feely and very flirty, even with me. The sexual innuendo wasn’t remotely subtle. I responded vaguely, “Tell me about it.”
Gloria, another of my MILF stroke fantasies, took my hand and led me into her house and downstairs into her party room. There were a dozen people there, all of whom I recognized from my parents’ gatherings. It seemed to be a sexy Disney Princess theme party, each sexy MILF costume more outrageous than the last. The dark-skinned Elma who worked in real estate with my Mom was ridiculously hot, came as Mulan, covered only in with several layers of diaphanous material which, if the light was just so, you could peer all the way through to her milk chocolate skin. Mom’s assistant, the chunky but very pretty Cassidy, was wearing a too-tight Cinderella costume with a slit in one side of her long ballroom gown up to her waist, and her blonde wig really brought out her blue eyes and dimples. Nice leg! No sign on the exposed hip of any panties. The wife of Dad’s partner, a trophy wife twenty years younger than he, was dressed as Ariel with mermaid non-legs and everything, so whenever she needed to go anywhere she had to be carried, a service she rewarded with wet kisses. Her vibrant red hair, hypnotic green eyes and bright green lipstick stood out even more in her mermaid costume. But her upper body was best: it was covered only by multi-hued aqua body paint which kept no secrets. Everywhere I looked were reasons for my dick to get so stiff I desperately wanted to give it some attention. My Dad’s best friend’s wife, Katie, six months pregnant, was dressed as Sleeping Beauty. She looked incredibly uncomfortable in the ill-fitting sleep-rumpled costume (unless she’d been doing something else in bed for the past hundred years). Would it be neat for thorny Prince Phillip to kiss awake an Aurora who was already two thirds of the way to delivering a baby and to make her his bride? Could such a baby become crown prince or would he be known as His Highness the Royal Bastard? The implications were like a Disney soap opera!
Wearing the always hot Jasmine harem girl outfit which also didn’t conceal much if you enjoyed looking through as opposed to around fabric, was my Mom’s old college roommate, the big-busted high school teacher Ellie. Whenever Mom and she got together they were incredibly touchy feely and I’d had many a stroke fantasy picturing them in college munching on each other’s cunts. Whenever they got together they talked like drunken sailors and hinted at a time when they’d been really crazy. Right now my Mom, still in her fucking hot Belle costume, was sitting on Ellie’s lap and giggling drunkenly. Her face was flushed in the same way Pamela (my recent ex) had always gotten when she was horny from my fingering, licking or fucking her pussy. I couldn’t see where Ellie’s left hand was and I wondered hopefully whether my sick imagination was right. Just then one more sex object (at a party like this, objectification was unavoidable) walked in from the bathroom. My mouth dropped. It was our locally famous weather girl Miranda Collington. Tonight she was dressed in a painted-on Jessica Rabbit costume (not actual body paint this time) that took your (all right, my) breath away. I don’t think Jessica Rabbit is a Disney princess, but who the fuck cares? Dressed in black thigh highs, one of them showing way past the top, and I think they must have been five-inch pumps, I took one look at her and got weak at the knees (yes, and breathless).
Miranda had been the local weather girl since she was eighteen, back in 1988. She was famous for her long legs which were always, and I mean always, in hosiery, which had been pretty common in the eighties but was incredibly rare in 2011. Like my Mother, she was a constant focus of my stroke sessions.
Distracted by the sight of Miranda, who stood out even in that sea of pulchritude, I barely noticed when Gloria announced my arrival. “Ta-Dah! Look at the beastly man who has graced us with his presence!”
Everyone looked up and I was greeted warmly, and in many cases flirtatiously. My Mom got off the gorgeous Ellie and wobbled towards me. She fell into me and hugged me tight. She slurred slightly, “You finally made it, honey.”
Attempting to sound just like my Father, I replied slyly, “Baby, I never planned to miss this. I got here as soon as I could!”
She grabbed my hand and whispered into my ear, “You are soooooo lucky you showed up when you did; Ellie has me so fucking horny!”
My cock flinched at hearing my MILF Mother talking so slutty and confirming a long-held assumption and stroke fantasy about her and Ellie. Pushing the envelope, I asked, “How did she get you so horny, honey?”
Mom just shrugged. “You know how she gets.”
Stunned but delighted by Mom’s clingy attentions, I asked, “So what’s the plan now?”
Before my Mom could answer, and interrupting so many nasty possibilities spinning in my head, Gloria announced, “Charades time!”
My Mom smiled and whispered, “I guess your blow job will have to wait.” She gave a quick subtle squeeze to my already stiff and eager cock, looked at me with a strange look and wiggled away. My Mom sat back down in Ellie’s lap and patted the couch, indicating I should join her. I obeyed like an obedient puppy dog, sitting beside my Mom. I hemmed and hawed whether I should put my hand on my Mom’s silk-stockinged legs. The decision was made for me a minute later when Mom grabbed my hand and put it there herself! I had touched and massaged her nylon feet many times, always fantasizing about my hands being all the way up on her thighs and now she’d just put one there! It was happening! I just sat back, stroked my Mom’s smooth soft leg and enjoyed the moment.
The game started and it was couple against couple. I watched vaguely as the other couples acted things out. When it was our turn, Gloria called me up and handed me a card displaying a quote: ‘two heads are better than one.’ I was happy to get an easy one. As soon as my time began I went to work and Mom quickly got it right.
My Mom slyly added to the room, her tone dripping in sexual innuendo, “I’ve always thought two, even three heads were better than one.” Everyone laughed and Mom winked at me. The wink and hearing my Mother use such an innuendo made me want her even more.
Ellie got up to go to the washroom and I sat back down beside my Mommy princess and she repositioned herself to lean on me in such a way that her voluminous skirts completely hid what she was about to do. She slowly ripped open the Velcro so it wouldn’t make that telltale noise, slipped her hand inside my costume and fished my cock out of my underwear! I thought I might come right then, but somehow I didn’t.
She gave me an odd look again and said, “Interesting.”
I asked, suddenly nervous, as I worried she knew it was me, “How so?”
There was a long silence where my Mom seemed to space out before asking me, seemingly sincere, as she gave me a solid how-do-you-do squeeze, “Did I get you that hard, Baby?”
Without hesitation I confirmed, “It’s all you Alexis.”
Her smile went wide and she began to slyly and unknowingly give her son a hand job. “Baby, your cock is so fucking hard.” I looked around the room and I can’t actually testify to anything specific, but it appeared as if various other couples might be similarly engaged.
She kept gently playing with my cock until Ellie returned to the couch. Mom gave me one last squeeze before whispering, “We aren’t done here, Baby.”
I tried to calm down, my head spinning from the fact Mom had just been playing with my cock. For the next few minutes I watched others play out their charades and now more confident, I put my hand back on my Mom’s thigh. I moved it up and down gently, the touch of her pantyhose-covered legs the ultimate tease. The sensual tease continued until it was Mom’s turn to do me… I mean to act out a charade for me.
As soon as she looked at the card she laughed and gave me a wink. This led to yet another twitch down below. As soon as her time began, she made the film symbol before falling to her knees and crawling sensuously towards me like a panther in heat. It was incredibly erotic. Once she got to me she used my thighs to push herself to her feet and started dirty dancing in front of me. I was so in awe of my Mom’s naughty moves I forgot we were playing a game! She turned around to grind her ass on my lap and I whimpered in pleasure. Suddenly the answer was obvious and I shouted/moaned “Dirty Dancing!” She stood up, slyly squeezed my cock with her hand and gave me a full-on flirt, fluttering eyelashes and all, moaning, “I hope now you’re ready for some dirty fucking, Baby.”
One of the guys high-fived me after hearing that offer and Mom leaned into me cleavage first and whispered, “Meet me in the upstairs bathroom in a couple of minutes.”
My MILF Mom walked away and I took a deep breath. If I wanted, I could just waltz upstairs and fuck my Mom! The majority of me was screaming ‘Go for it!‘ while my conscience reminded me she was my Mother and drunk and unaware that I wasn’t her husband. My cock-head doing the thinking for me, I felt myself standing up and heading nonchalantly (yeah, right) upstairs to the bathroom.
At the door I took one last deep breath, one last brief hesitation, before I knocked on the door. Mom opened it and tugged me in.
She smiled, making her look even more beautiful, and dropped to her knees. I watched, frozen in shock, while she pulled my fully-erect cock out of my convenient Velcro opening and took it in her mouth.
While I enjoyed the best blow job of my young life, I pondered the obvious fact that Mom thought she was sucking her husband’s cock. I tried to get my head wrapped around this stunning development, but it was very difficult with Mom’s lips wrapped around a cock that had stolen all the blood from my brain. Pamela had never given me head for more than a couple of minutes and had never finished me, so Mom’s eager blow job was amazing. I just watched from above as my beautiful Mom bobbed up and down on my cock, devouring it whole.
After only a couple of minutes of constant deep-throat cock sucking, I could feel my balls bubbling, I warned, “I’m going to come soon!”