What Mom Doesn't Know Will Fuck Herbysilkstockingslover©
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!
What Mommy Doesn't Know Will Fuck Her
Until I read stories on Literotica, I had no idea how many sons had fantasies...or sometimes realities...of having sex with their Mother. I mean, it is not 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 my 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?"
"Seriously, this is really embarrassing."
"Fine, I promise not to ridicule you too bad."
"That's not so bad. I was expecting Big Bertha or Old Woman Burgess. First, your Mom is ridiculously hot and second I have stroked about my Mom many 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. A perverted little freak. But hey, at our age, every guy is a perverted little freak. Christ, even Hamlet supposedly had a thing with his Mother."
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.
She didn't help any either. She was a real estate agent and always dressed-up in skirts and heels. Both of which had become fetishes of mine, probably because I grew up seeing them on the hottest woman I knew. I was a sixteen when I started giving my Mom foot massages after a day at work. She always kept on her stockings and my cock always rose when her stocking-clad legs were on my lap. She had to have known what it did to me, but she never let on and it never went any further then a son giving his Mother a gentle foot massage.
She also knew she was still hot. She flirted with my friends and loved the compliments my friends threw at her. She was a MILF and she knew it, and she revelled in it. That said, I never thought I would have the chance to do more than just her feet...and then Halloween occurred.
Every Halloween my parents got dressed up as a sweet couple and went to some big party. Every year you could see their excitement for the big day. Mom's creative juices always came alive for Halloween too. She always designed and made the costumes, often starting months in advance. I can't recall all the outfits but do remember a few: Bonnie and Clyde with Mom dressed as a very hot flapper girl (Mom looked stunning in fishnets and the cute bob haircut), Fred and Wilma Flintstone, which had my dick thinking Bam Bam all night (to this day I still have a photo of Mom as Wilma hidden under my bed for stroke sessions), her fifties theme 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 (that 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 until Halloween Eve.
Now I have always been a believer in destiny or fate. And it could only have been through destiny that the dominos would have fallen the way they did...giving me the perfect opportunity to fuck my Mother. First off, my Dad phoned at five o'clock to tell Mom that due to late bargaining (my Dad is a high powered mediator...the guy you hire to end long standing feuds), he wasn't going to make it home in time, although he might get in late enough to meet her at the party. Mom was furious, because this was a night she always looked forward to, and had put hours upon hours into making the costumes perfect. Although clearly mad at Dad, she still planned to go to the party.
A couple of hours later, Mom came downstairs in her Belle costume. My cock was instantly stiff. I have always secretly thought Belle was the hottest cartoon character, in the same way I think Betty is easily the hottest Archie girl. But my Mom dressed as Belle, in the blue dress, her hair exactly the same and the darkest brown pantyhose I have seen, other than Hooter's waitresses, was the sexiest moment of my young life.
I did what I always seemed to do when talking to 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 rather 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 will make it back."
She shrugged, gave me a kiss on the cheek, like she always did. And she was off.
All the stars lined up perfectly. Even the fact I was home in the first place was a long string of fateful moments. Now usually I go out to a Halloween party as well, but truthfully just didn't feel like it. I had been dumped a couple of weeks before by my girlfriend of eight months, Pamela, and didn't really want to see her. So I was watching "Halloween" for the umpteenth time when the phone rang.
"Is your Mom still home?" dad asked.
"She left an hour ago," I replied.
"Shit," he swore, "was she mad?"
"Think PMS time cubed and you may be close," I warned.
"Double shit," he cursed, "I tried her cell and she didn't answer."
I walked over to the kitchen and saw it sitting in the charger. "She wouldn't. It is being charged."
"Triple shit," he swore, knowing he was indeed in deep shit. After a pause, "Well, can you leave her a note? This is going to be an all-nighter."
"Shit," I repeated, which got a nervous chuckle.
Mom was sexy, and caring, but you never wanted to be on her bad side.
"I 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 where she was headed.
"Better be a whole garden. This year's costumes were her best yet."
We said our goodbyes and I returned to watching TV. About ten minutes later, a light bulb in my head flickered. A few seconds later the light bulb shined bright as the sun.
I went upstairs into my parents' room. Lying on the bed was Dad's Beast costume.
I put it on and was shocked at how comfortable the costume was. My Mom had thought of everything as it even had two battery-powered mini-fans in it to keep you cool. I also noticed that she had created a velcro opening at the privates, so you could take a piss without completely taking off the costume. I looked in the mirror. 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; and I had the same voice as my father. I went downstairs, grabbed the address, jumped into Dad's Mercedes and drove to the party.
I arrived at the party a few minutes after eleven and was met at the door by my Mom's best friend Gloria, dressed in a Snow White costume. Her face brightened when she saw me. In her usual giddy voice, she said, "Thank God, you are here Ted, Alexis is really mad at you."
"I know," I acknowledged, "That's why I hightailed it here."
"She's had a few glasses of wine and you know how she gets when she gets into her wine," she warned me.
Thinking about the few times I have seen my Mom intoxicated, usually on New Year's Eve, I recall my Mom bring extra touchy feely and very flirty, even with me. The sexual innuendo isn'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 people I recognized from many of my parents' gatherings. It also seemed to be a Disney Princess themed party. The dark skinned Elma, who worked in real estate with my Mom, was ridiculously hot, dressed as Mulan. Mom's assistant, the chunky, but very pretty Cassidy, was wearing a too-tight Cinderella costume, but the blonde wig really brought out her blue eyes and dimples. The wife of Dad's partner, a trophy wife twenty years younger than him, was dressed as Ariel with mermaid legs and everything. Her vibrant red hair and hypnotic green eyes stood out even more in her mermaid costume. My dick was so stiff I desperately wanted to give it 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 costume.
Wearing the always hot Jasmine outfit was my Mom's old college roommate, the big-busted high school teacher, Ellie. Whenever Mom and her got together they were incredibly touchy feely and I had many stroke fantasies of them in college munching on each other's cunts. When they are together they talked like drunken sailors and hint at a time when they were 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 was when she was horny from me fingering, licking or fucking her pussy. I couldn't see Ellie's hand and I wondered hopefully that my sick imagination was right. Just then one more girl walked in from the bathroom. My mouth dropped. It was our locally famous weather girl Miranda Collington. Dressed as Jessica Rabbit, who I don't think is a Disney princess, but who the fuck cares. Dressed in black thigh highs and I think five inch pumps, I looked at her and was weak at the knees.
Miranda had been 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 pantyhose, which was 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, I barely noticed when Gloria announced my arrival. "Look who has graced us with his presence."
Everyone looked up and I was greeted warmly. My Mom got off the gorgeous Ellie and staggered towards me. She fell into me and hugged me tight. She slurred slightly, "You made it, honey."
Attempting to sound just like my Father, I replied slyly, "Baby, I never planned to miss this."
She grabbed my hand and whispered into my ear, "You are soooooo lucky you showed up, 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. Pushing the envelope, I asked, "How did she get you so horny, honey?"
Mom just shrugged.
Stunned by Mom's forwardness, I asked, "So what is the plan now?"
Before my Mom could answer, with so many nasty possibilities spinning in my head, Gloria announced, "Charades time."
My Mom smiled and said, "I guess your blow-job will have to wait." She gave a quick subtle squeeze of my already stiff and eager cock and wiggled away. My Mom sat back with Ellie and padded the couch implying I should join her. I obeyed, like an obedient puppy dog, sitting beside my Mom, who was back on Ellie's lap. I hummed and hawed whether I should put my hand on my Mom's silk stocking legs. The decision was made for me a minute later when Mom grabbed my hand and put it on her silky leg. I had touched and massaged her nylon feet many times, always fantasizing of my hands being on her thighs and now it was happening. I just sat back and enjoyed the moment.
The game started and it was couples. I vaguely watched as the other couples acted things out. When it was our turn, Gloria called me up and handed me a card, I looked at it. Mine was 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, her tone dripping in sexual innuendo, "I 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 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 in such a way that she was leaning on me at an angle that completely hid what she was about to do. She slipped her hand inside my costume and fished my cock out of my underwear. I thought I might come right then, but luckily I didn't.
She gave me an odd look and said, "Interesting."
I asked, suddenly nervous, "How so?"
There was a long silence where my Mom seemed to space out before asking me, seemingly sincere, as she gave 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."
She kept her hand slowly playing with my cock until Ellie returned to the couch. Mom gave one last squeeze before whispering, "We aren't done here, baby."
I tried to calm down, my head spinning from the fact Mom was just playing with my cock. The next few minutes I watched others play charades and, now more confident, put my hand back on my Mom's thigh. I moved my hand 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 act.
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 the time began, she made the film symbol and fell to her knees and crawled towards me. It was incredibly erotic. Once she got to me, she stood up 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. Her ass ground on my lap and I whimpered in pleasure. Suddenly the answer was obvious and I shouted-moaned Dirty Dancing. She stood up, squeezed my cock with her hand slyly, and flirted, "I hope you are ready for some dirty fucking, baby."
One of the guys high-fived me after that comment and Mom leaned into me 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 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 was not her husband. My cock-head doing the thinking for me, I felt myself standing up and heading to the bathroom.
At the door, I took one last deep breath, one last brief hesitation, before I knocked on the door. Mom immediately opened the door and pulled me in.
She smiled, making her even more beautiful and dropped to get knees. I watched, frozen in shock, while she pulled my fully-erect cock out of my the very 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 my cock. Pamela never gave me head for more than a couple of minutes, 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 my dick whole.
After only a couple of minutes of constant deep-throat cocksucking, I could feel my balls bubbling, I warned, "I'm going to come soon."
She took her luscious lips off my cock and smiled, "Do you want me to swallow it Baby or would you like to jerk off and shoot your cum on my face?"
I couldn't believe the choice I was just given. I had come in a couple of girls' mouths, but had never had a chance to be a part of every guy's fantasy, the porn movie finale. I mumbled like a first time teenager, worried I could have given myself away, "Can I come on your face?"
She smiled, "Tell me when you are close, Baby." She took my cock back in her mouth and bopped back and forth, even with more reckless abandon than before.
She sucked my cock furiously fast, seemingly desperate to get me off. It didn't take long before my balls were boiling and I moaned, "I'm gonna come soon."
She took my cock out and jerked me off with her left hand. Her nasty words both shocked me and led to my final vision, "Come on, Baby, shoot that hot cum of yours all over my slutty face. Come on me, Baby, coat my face with your hot cum." I spasmed, and shot a pretty large load all over my Mom's beautiful face. My cum landed on her hair, her forehead, her nose and her chin. Once I finished spraying her face, she took my cock back in her mouth. After a couple of minutes, my cock was still fully erect. She took my cock out of her mouth and smiled, while standing back up, "Fuck I love your cock, baby."
I replied, shocking myself, "And I love your cocksucking lips."
She said, "We better get back, Baby. But when I get you home you owe me a good tongue lashing."
I stammered, "O-o-of course," while pushing my still erect cock into my costume.
Mom asked, while trying to clean my cum from her face, "Still hard, honey. What has got into you? You're like your old 18-year-old self."
Wanting to end this conversation before she caught on to what she had just did, I answered, "You bring out the best in me, Honey," and opened the door, leaving her to finish freshening up.
Returning to the party, all eyes looked at me. I went and grabbed a drink from the bar and Ellie came up behind me and whispered, "Fuck Ted, I was so close to seducing your wife."
"What?" I asked, confused by the proclamation.
"I am going to fuck her again one day, Ted, that is a promise," she guaranteed, before walking away and going directly to my Mom.
The next hour was excruciating. All I wanted to do was get home and hopefully fuck my Mom. Instead we played bobbing for Barbie parts and actually, believe it or not, attempted to do the Thriller dance as a group, which was either damn funny or ridiculously absurd, depending on how you looked at it.
Finally, my Mom, who had ignored me for the rest of the night, came over to me all flirty and asked, "So big boy, are you ready to take me home?"
I briefly flinched, as big boy was the name she called me when I was young. I stammered, "L-l-let's go."
She winked at me and said, "I'll meet you at the car in five."
She gave my still rigid cock a squeeze and went to say her goodbyes. I did my thirty-second byes and waited outside. Each second felt like an eternity as I waited for my Mom to come and be an unknowing accomplice to incest.
Finally, she arrived and instead of getting in the car, grabbed my hand-paw, and led me to the back-yard. As soon as we were in a secluded spot, she lay on the grass, lifted up her skirt and begged, "Get down here, Baby, I need to come so fucking bad and I want that expert tongue munching on my pussy." She pulled her pantyhose apart ripping them open to reveal she was not wearing underwear, and I was now staring at my Mom's cunt.
Realizing this was probably a once-in-a-lifetime opportunity, I tried to make every fantasy I ever had come true. Instead of diving into her glistening shaved pussy, with a sexy trimmed patch above, even better than I ever thought it would look, I took off her heels and took her stocking-covered foot into my hand and began to give her one of my famous foot massages. After I started doing it, I worried she would realize it was her son and not her husband.
She moaned, "Oh Baby, that is so nice."
Instead of talking, I lifted my head off just enough so I could take her stocking-clad toes in my mouth. Something I had fantasized doing to my Mother so many times.
"Oh my Baby, that feels so fucking good," my Mom purred, her breathing changing slightly.
I spent a few minutes kissing, licking, nibbling and massaging my mother's perfect silk-covered feet before I slowly moved up her leg, my tongue moving up, ever so softly, wanting this fantasy-come-true to never end. I reached her pussy, her scent giving away her excitement. My tongue grazed her clit and she involuntarily shook. She begged, "Please Baby, lick my cunt. I need to come so fucking bad."