Note 1: This is a 2011 Halloween entry, please vote!
Note 2: Special thanks to Estragon for the copy-editing work! Tex Beethoven underwent an extensive rewrite in December 2018.
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Before I started reading stories at Literotica, I had no idea how many sons fantasized about having sex with their mothers… and sometimes even actually felt it. I mean, this isn’t really a conversation between a boy and his friends. Think about this:
“Dude, you know who I want to fuck the most?”
“Anyone who moves, I guess.”
“That’s true. But do you know what gets the most attention late into the night during my daily stroke sessions?”
“Beth, the cheerleader?”
“He’s in the top five, no question.”
“So, who’s going to be number one?”
“Promise you won’t judge?”
“No, you did something crazy; I did the same thing.”
“It was really embarrassing, to be honest.”
“Okay, I promise I won’t laugh at you too much.”
“My mother.”
“It’s not bad. I was hoping it would be Big Bertha or Old Lady Burgess. First of all, your mom is so sexy, and second of all, I’ve touched my mom so many times.”
“do you have one?”
“Of course, and my mom isn’t as hot as yours.”
“So doesn’t that make me weird?”
“Oh, that makes you a freak. It also makes you a perverted little freak. But hey, in our age, everyone is a perverted little freak. Hell, even Hamlet should be interested in his mother. He should sing about his mother!”
…..
Anyway, the point is simple. As I got older, I became more and more obsessed with sleeping with my mom. My fantasies changed from cheerleaders and hot blondes to my forty-three-year-old, blue-eyed, brown-haired, big-breasted mother.
She was no help as far as calming me down. She was a real estate agent and always wore skirts, stockings and high heels. These three have become obsessions of mine, probably because I grew up seeing the sexiest women I knew wearing them. At the age of sixteen I started giving my mom foot massages after a hard day’s work. She always wore stockings and my cock always got hard whenever her stockinged feet touched mine. She had to know what it was doing to me, but she never showed it, and it never went beyond a son respectfully giving his mother a foot massage, at least outside of my fevered brain.
Mom knew she was still hot. She flirts with my friends and loves to compliment them. She’s a mom, she knows that, and she enjoys it. That said, I never thought I’d get to do anything other than her feet…but then Halloween happened.
Every Halloween, my parents would dress up as a sexy couple and go to a big party. (Mom is hot anyway, and as a straight guy, I don’t think men can look any sexier .) Every year I watch their excitement grow for the big day, Mom’s creativity always comes alive on Halloween; she always designs and makes both costumes, often starting months in advance. I don’t remember all the costumes, but some recent ones: Bonnie and Clyde and mom dressed as a sexy mod girl (mom in fishnets, with a beautiful bob haircut, and holding a toy Tommy gun, with a devilish smile on her face, ready to shoot someone else’s child, mom playing Wilma with a ripped neckline and a skirt that almost reveals her naughty parts, in a photo that was still hidden under my bed), her fifties idols were Marilyn Monroe and James Dean (I also have a hidden photo of them during the game), last year she was Princess Leia and her dad was Luke Skywalker Walker (her transparent white dress, no underwear, kept my lightsaber straight for months). This year they will star in Beauty and the Beast. As true, mom refused to show her costume to anyone until Halloween, if that sentence is not superfluous.
Whatever you call it…fate or destiny, I’ve always believed in it. It could only be fate that the dominoes fell the way they did…giving me the perfect opportunity to fuck my mom and live to tell the tale (for you, I’m not going to kiss the baby and kick his ass around with his mouth shut). First, my dad called my mom at five to tell her that he wouldn’t be back in time due to some late bargaining (dad was a high powered mediator…the person you appoint to negotiate a long running feud) home, although he could arrive early to attend a party with her later. Mom was angry because this was the night she had been waiting for and she spent a lot of time making out the perfect outfit . Even though she was angry at her dad, she was still going to get out of the house, go to the party and do whatever it took to make it happen.
A few hours later, at seven, mom came down in her Belle costume and wanted to make my cock her guest (do you know that song)
I always secretly thought Bella was the hottest cartoon character, just like I thought Betty was easily the hottest Archie girl. But seeing my mom dressed like Belle, wearing a strapless blue peasant dress that showed off her flawless upper chest, though there was nothing illegal about it if she stayed straight, and her hair was the exact same color as Belle’s, plus wearing the darkest brown pantyhose I’ve ever seen on a waitress outside of a Hooters restaurant, was the sexiest moment of my young life.
I did what I always do when talking to my mom. I complimented her. “Wow mom, you could be Belle in real life. This is the best costume you’ve ever worn!”
“Do you think so?” she asked, smiling and striking a seductive pose.
“I know it is. Daddy would love it.”
Mother’s smile slowly disappeared. “I can’t believe he betrayed me for the All-Transportation Alliance .”
“I’m sure he’ll be back soon.”
He shrugged and said, “He’s the best!” But then he said to me: “But it’s not your fault, dear, and you said it was great.” He kissed me for a moment, then let go. I kissed his cheek as usual and then walked away, leaving me standing there.
All the stars were perfectly aligned, even if I didn’t know it. Even my homecoming at first resulted in several unfortunate moments. Normally after saying goodbye to my parents (not wanting to give up what my mother looked like that year) I usually go to the Halloween party as well, but this year I didn’t feel like it. My girlfriend of eight months, Pamela, had left me a few weeks earlier and I really didn’t want her there. Just as I was watching Halloween for the umpteenth time, the phone rang again.
“Is your mom still there?” Dad asked nervously.
“She left an hour ago,” I replied.
“Hey,” he cursed, “is he crazy?”
“Think of PMS, and you might be close to it,” I warned.
“Hey,” he cursed, “I tried his phone and he didn’t answer.”
I went into the kitchen and saw it sitting on the charger. “She can’t. It’s charged right here.”
“Triple fuck,” he cursed, knowing he was sinking really deep into shit. There was a pause, “Okay, can you leave a note for her? It’s going to be all night.”
“Shit,” I parroted, causing Dad to laugh nervously.
Mom is sexy and caring, but you never want to upset her.
“I’d better buy her some flowers,” he reasoned. I saw an address in my mother’s handwriting on a piece of paper and I assumed it was to let Dad know where she was.
“Better buy her a whole garden. This year’s costume is her best one yet!”
We said goodbye and I went back to watching TV. After about ten minutes, a light bulb went off in my head. After a few seconds, the bulb shined brightly like the sun!
I ran upstairs and went into my parents room. The bed was covered with Dad’s Beast costume.
I took off my panties and put it on, I was so pleased with how comfortable it was. My mom has thought of everything because it even has two battery-powered mini fans to keep the animal cool. I also noticed that it had a devil-like hole in its private parts so that daddy… no, so that I… could pee without taking off the costume. I looked in the mirror through the mask that covered my whole head (there were cutouts for the eyes and ears, and the ear holes were covered with long animal hair). No one will know it’s me. I’m as tall as my dad; my eyes are as blue as my dad’s; even my voice is the same as my dad’s. I went down, got the address, jumped into dad’s Mercedes (the first thing a good negotiator does is negotiate his fee), and set off to the party.
I arrived at the party a few minutes after nine-thirty and was greeted at the door by Gloria, the party hostess, wearing a Snow White dress with a deep scoop neckline. Her face lit up when she saw me. She said in her usual lisp, “If Alexis is Belle, you must be Ted. Thank God you’re here, Alexis is really mad at you!”
“I know,” I admitted, “that’s why I ran here as soon as I got home.”
“She’s had a few drinks, you know how she reacts when she’s drunk,” he warned me, winking at me.
Thinking back on the few occasions when I saw my mother drunk, usually on New Year’s Eve, I remember my mother being particularly sensitive and very flirtatious, even with me. The sexual hints are nothing more than subtle. I replied vaguely: “Tell me.”
Gloria, my second MILF apoplectic fantasy, took me by the hand and led me into her house and downstairs to her party room. There were about a dozen people there, all of whom I recognized from my parents’ party. It appeared to be a sexy Disney princess-themed party, with each sexy MILF costume more revealing than the last. Dark-skinned Irma, who worked in real estate with my mom, was so sexy that, like Mulan, she was covered in just a few layers of transparent material so that if there was enough light you could see right down to her milk chocolate. Mom’s assistant, the fat but very pretty Cassidy, wore a very tight Cinderella costume, a long ball gown with a slit on one side up to her waist, and her blonde wig really accentuated her blue eyes and dimples. What legs! There was no trace of buttocks exposed by underwear. Dad’s partner’s wife is a trophy wife who is twenty years younger than him and dresses up like Ariel, a mermaid who has no legs so she has to hold him whenever she needs to go somewhere and gets a shower of wet kisses in return. Her bright red hair, brilliant green eyes and bright green lipstick look even more alluring in her mermaid costume. But her upper body is the best: covered only in several shades of aqua body paint, there’s no mystery. There was a reason my cock was so hard everywhere I looked and I was desperate to get some attention for it. My dad’s best friend’s wife, Katie, was six months pregnant and dressed like Sleeping Beauty. She looked extremely uncomfortable in that ill-fitting, wrinkled nightgown (unless she’s been doing something else in bed for the last hundred years). Wouldn’t it be great for the troubled Prince Philip to kiss Aurora awake when she’s two-thirds through labor and make her his bride? Would such a child become the crown prince or be called “His Majesty’s illegitimate son”? It makes sense like a Disney soap opera!
Always wearing the hot Jasmine harem girl outfit that doesn’t hide much if you prefer to look rather than dress around , it’s my mom’s old college roommate, sexy high school teacher Ellie. They act super sensual whenever mom is with them and I have often imagined them chewing each other’s pussy in college. Whenever they get together, they talk like drunken sailors and hint that they were truly crazy once. Now my mom was sitting on Ellie’s lap, still wearing the extremely revealing outfit and giggling drunkenly. Her face was as red as it was when Pamela (my most recent ex-girlfriend) got turned on by me fingering, licking or fucking her pussy. I couldn’t see where Ellie’s left hand was, and I wondered if my morbid imagination was correct. Just then, another sex object (objectification is inevitable at such a party) comes in from the bathroom. The corners of my mouth drooped. This is Miranda Clinton, our famous local weather forecaster. Tonight, she’s wearing a Jessica Rabbit paint costume (not actual body paint this time) that will leave you (well, me) surprised. I don’t think Jessica Rabbit is a Disney princess, but who cares? Wearing black stockings, one of which went so high above the top that I thought they must be five-inch heels, I took one look at her and went weak in the knees (yes, breathless).
Miranda has been the local weather forecaster since 1988, when she was 18. Like my mother, she has been the focus of my stroke care.
Even in the beautiful sea, Miranda stood out and I was so distracted that I barely noticed Gloria announcing my arrival. “Ta-dah! Look at this beast man, he graces us with his presence!”
Everyone looked up and I was greeted warmly, often with a teasing tone. My mother got off the beautiful Ellie and walked towards me. She fell on top of me and hugged me tightly. She said vaguely: “My dear, you finally succeeded.”
Trying to sound like my dad, I smartly replied, “Baby, I never wanted to miss it. I got here as fast as I could!”
He grabbed my hand and whispered in my ear, “You’re lucky you showed up; Ellie makes me so horny!”
My cock got hard as I listened to my mom talking so sexually, confirming my long-held assumptions and nostalgic fantasies about her and Eli. I pushed the envelope further and asked, “Honey, how does she make you so horny?”
Mom just shrugged. “You know how he got it.”
Surprised but pleased by my mom’s attention, I asked, “So what are your plans now?”
Before her mother could answer, Gloria announced, “It’s puzzle time!”
My mom smiled and whispered, “I guess your blowjob will have to wait.” She gave my already hard and eager cock a quick, subtle squeeze, gave me a quizzical look, and shrugged and walked away. My mom sat back on Ellie’s lap and patted the couch to indicate that I should follow her. I was as obedient as an obedient puppy and sat down next to my mom. I was hesitating whether to put my hand on my mom’s stockinged legs. A minute later, when mom took my hand and put it there herself, my decision was made! I had touched and massaged her nylon legs so many times, always imagining my hands on her thighs, and now she had just put one of her hands there! It’s happening! I just sat down, caressing my mom’s smooth, soft legs and enjoying the moment.
The game began, one versus one. I vaguely saw the other couples performing. When our turn came, Gloria called me and gave me a card on which was written: “Two heads are better than one.” I was happy to get a simple head. As soon as my time began, I went to work and my mother quickly finished the task.
My mother slyly said to the room, her tone dripping with sexual innuendos, “I’ve always thought that two, or three heads, are better than one.” Everyone laughed, and mom winked at me. Winking and hearing my mother give such innuendos made me want her even more.
Ellie got up to go to the bathroom and I sat back down next to my princess mom and she positioned herself in front of me so that her full skirt completely covered what she was about to do. She slowly undid the Velcro so it didn’t sound too fairytale, reached into my dress and pulled my cock out of my underwear! I thought I might come right away, but for some reason I couldn’t.
He gave me another weird look and said, “Interesting.”
I suddenly panicked, worried that he would know it was me, and asked, “How is this possible?”
After a long silence, my mother seemed to be getting nervous, then she squeezed me tight and asked me, she looked serious, “Hello, do I feel that bad, baby?”
I confirmed without hesitation: “It’s all you, Alexis.”
She smiled brightly and quietly and unconsciously started giving her son a hand job. “Baby, your cock is so hard .” I looked around the room, I couldn’t really confirm anything specific, but it seemed like a few other couples had similar engagements .
She continued to gently play with my cock until Ellie returned to the couch. Mom squeezed me one last time and whispered, “Baby, we’re not done yet.”
I tried to calm down but my head was spinning from the way Mom had just played with my cock. I spent the next few minutes watching the others play pretend, and now feeling more confident, I placed my hand back on Mom’s thigh. I moved it up and down slowly, the feel of her pantyhose covered legs was extreme teasing. This erotic teasing continued until it was Mom’s turn to play with me…I mean play on me.
She smiled and winked at me as she saw the card. This sent another jolt down the line. As soon as her time started, she gave the movie cues, then got down on her knees and started crawling towards me sensually like a panther in heat. It’s incredibly erotic. As soon as she reached me, she pushed herself onto my thighs and started dirty dancing in front of me. I was so amazed by my mom’s naughty antics that I forgot we were playing a game! She turned around and started rubbing her ass against my legs, making me squeal with pleasure. Suddenly the answer was obvious and I yelled/groaned “Dirty Dancing!” She stood up, slyly cupping my cock with her hand, flirting with me over and over again, fluttering her eyelashes and moaning, “I hope you’re ready for something dirty. Now fuck me, baby.”
One of them gave me a high-five at the suggestion, and Mom was the first to lean in toward my cleavage and whisper, “Meet me in the bathroom upstairs in a few minutes.”
My mom walked away and I took a deep breath. If I wanted to, I could just walk up and fuck my mom! Most of me is screaming ‘ come on! ‘ However my conscience reminded me that she was my mom, she was drunk and didn’t know I wasn’t her husband. The head of my cock did the thinking for me and I felt myself stand up and casually (yeah, right) walk upstairs to the bathroom.
At the door, I took one last deep breath, one last brief hesitation, and then knocked. Mom opened the door and pulled me in.
She smiled, making herself look more beautiful, and dropped to her knees. I watched in amazement as she pulled my fully erect cock out of its convenient Velcro hole and took it into her mouth.
As I enjoyed the best blowjob of my young life, I considered the obvious: Mom thought she was sucking her husband’s cock. I tried to wrap my head around this amazing development, but it was too hard to wrap Mom’s lips around a cock that stole all the blood from my brain. Pamela never gave me head for more than a few minutes and never finished me off, so Mom’s eager blowjob was fantastic. I just watched from above as my beautiful mother slithered up and down my cock, swallowing it whole.
After a few minutes of continuous deepthroating and cock sucking, I felt my balls bubbling and warned, “I’m going to cum soon!”
