Weird Wild Weekend - Freaky Friday

Author's note: This is a work of fiction and, as such, does not reflect any actual events. Character resemblance to any persons, living or dead, is entirely coincidental. If depictions of any form of non- or semi-consensual sex offends or bothers you in any way, perhaps consider that the phrase "Reader Discretion Advised" may apply to you. The author does not condone any of his demented fantasies being played out in reality unless all parties involved are of legal age, sound mind and fully agreeable to the scenario beforehand. Please, remember it's just a story and try to not take it too seriously. Thanks for reading and happy fapping!

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I confess I've only recently lost my virginity. Really recently. As in, just last weekend. It was such an utterly insane experience and I can't tell anyone about it for real. No one could possibly believe me, and if anyone did believe me, my family would disown me and it would ruin my life forever. So I'm just going to make a post on the internet through an anonymous account. None of you will think it's real anyway, so I feel safe telling the whole truth. Here's the story of how I had sex with my own mother.

First, I suppose, I should give you a bit about myself. I'll say my name is Jim. I want to lie and describe myself as a smooth, cool ladies man with a winning boyish smile, the body of a teen Adonis and a dick so big it would make a porn-star jealous. I want to say that I've had at least a dozen girlfriends and know my way around a pussy like a lesbian. But, sadly, I'm just a plain, normal, slightly out-of-shape, reasonably decent-looking guy. My dick is a bit bigger than average when it's hard, about six or seven inches long and thick enough that my fingers only just touch when I grip it, but it's what you'd call a grow-er, not a show-er. Soft it looks something like a wad of gum that's fallen into a wastebasket at a barber's shop. It's probably part of why I don't feel very confident with girls. I dread them seeing me relaxed and naked. I do have the nice smile, though.

I live in a tiny, one-horse mid-western farm town that's finally grown big enough to qualify for a second horse, but still isn't big enough for a Red Lobster. I'm almost nineteen years old and because I'm something of a nerdy gamer stereotype, I've never been very good with girls. I'm a very average five-foot-nine inches tall and while I do have a bit of a belly, I'm not really fat...I just don't like exercise very much. Thankfully, I don't really eat much, either. I'm pretty pale because I don't go out often. I have short, dark brown hair I wear parted on the left and dark brown eyes that have never needed glasses. I got my dad's squashed nose and quirky sense of humor and my mom's small hands, elvish ears and penchant for sunburns.

I like to wear blue jeans and tee shirts and cheap sneakers with velcro instead of laces. Normal in almost every way physically, I do not stand out in a crowd at all. And, honestly, I kind of like it that way. Most people in my hometown don't like comic books and video games and Dungeons and Dragons like I do, so my circle of friends is small and tight. We've known each other since grade school pretty much and have kept ourselves mostly insulated from normal folks. Normal folks don't care about the quality of arcade ports, or covet the Wand of Orcus or know why they should always carry a towel. And we find tractors and touchdowns and twangy music mind-numbingly boring.

I'm not a total sad dweebie loser, however. I did have a girlfriend. In tenth grade. For a couple of months. Sarah Everstone was a pretty, if mousy little blonde with big glasses, small, perky tits and long, tight skirts that sat in front of me in math and was the student council secretary. Her dad was a security guard for one of the local grade schools and her mom sold Amway or Mary Kay or something like that. We used to study together and just sort of agreed without really saying anything that we were dating after I starting coming to her house to work on our algebra equations and she'd kiss my cheek when I left. We'd walk together in the halls holding hands and hang out at lunchtime or in the library and she'd let me copy her notes when I missed a day of class. I even took her out to dinner and a movie once. Yeah, she was that sort of girl. We never even so much as french kissed. She was adamant about "saving herself for marriage"...as her mother loved to remind me every time I came over. We broke up over the summer and they moved away a few months into eleventh grade. The rumor going around was that a member of the basketball team got her pregnant, but no one actually knew for sure why they moved.

I wasn't terribly interested in girls my own age, anyway. Oh, don't get me wrong, I'd have happily fucked any of them that offered. Hell, I was so used to being friend-zoned, if you were a girl in my peer group, I'd have probably fingered you for an hour and got you off a half dozen times even though I knew you'd just send me home with blueballs so I could sniff my finger while jerking off later if you'd have let me. I'm just a guy, after all. But an actual relationship? Like actually being interested in their shoes or trying to explain any of my hobbies? Introducing them to my friends? Ugh! Way more hassle than it's worth. So much drama and celebrity worship and childish nonsense and stupid teen angst. Older women seem much easier to deal with...they have all that mess together and aren't all uptight about not being seen as sluts. Well, maybe they are, but not in the same way.

Anyhow, between the day to day grind of my homework, my part-time job to pay for my car and gaming habit, spending most all of my free time in some fantasy land or other with my gamer friends and never really understanding girls anyhow, I was a pretty typical geeky, teen-aged, virginal mid-western boy. I know...a regular walking cliche, right? So how did I wind up with my mom? Relax, I'm getting to that. First, let me tell you about her.

I'm not sure exactly when she went from being "mom" to being a "milf", but it feels like those thoughts have always been there, vaguely wandering around the back of my mind. I was an only child and I was breastfed, so that may have played into it, especially since my mom's highly affectionate and loving. My father was never afraid to slap her ass or grope her huge boobs in front of me, either. And she's always been a bit uninhibited about not wearing all her clothes in the house when it's just us family, so there was a constant, subtle sort of low-level sexuality in the air when I was growing up. It was really easy to get good, long looks at all her most womanly parts sometimes, so as puberty kicked in and I discovered masturbation, she became prime jerk-off fantasy material. My erotic daydreams could be weirdly vivid, too, because my dad basically looks like a much older, taller version of me with facial hair.

She started to tuck it all away a little more as I got older and she began to notice my lingering gazes, so naturally I starting finding ways to get my looks in when she didn't know I was looking. Peeping on her getting in and out of the shower or dressing for work or catching her and dad having sex became a bit of an obsession some weeks. Sometimes I'd sneak into their bedroom late at night to watch her sleep. Occasionally, I'd even work up the courage to lift the blanket to take a peek and try to talk myself into touching her voluptuous body as she quietly snored. I have a real thing for the sexy, innocent vulnerability of sleeping girls. And to catch her in bed when she thought she was truly all alone and she got her little pink toy out of it's hiding place under the nightshirts in the back corner of her dresser's bottom drawer...well, that was one of my fondest dreams.

She was just perfect in my eyes. Exactly what a woman should be. When I properly hugged her close, she fit right up under my chin, which I felt was the best height for a girl. Her auburn hair was lusciously thick and fell past her waist when she didn't have it up in some fetching style. Her sharp nose, finely chiseled features and pale skin held a hint of ancient nobility and her intense green eyes could go from glittering gemstones to stormy rain-forest shadows with changes in her mood. The plush, feminine curves of her body said she'd worked hard to reclaim her figure after having a kid, but she had earned the right to the occasional cheeseburger and beer without feeling ashamed about it. She liked to wear tight shirts and loose skirts, didn't like to wear panties too often and only strapped her plump boobs into her 36DD bras when she had to go out in public. Yeah, I know what size bra my mom wears...are you really surprised?

I can still remember the feel of her heavy, warm breasts smooshing against my chest when she'd lean down to kiss me while tucking me into bed. And the way her shapely figure was silhouetted by the hallway light as she left my room, the gossamer fabric of her silken nightgown clinging to her lush curves. Or watching her as she moved about the house doing chores and cleaning up wearing nothing but a pair of panties and one of dad's shirts, her tits shifting and hanging and bouncing with gravity, her round bottom stretching her undies taut when she bent over and her thick mound teasing me behind the thin cloth with that heady aroma of light sweat and pussy juice wafting through the air while I pretended to play a video game. She kept her dense bush tidy in a neatly trimmed triangle and I don't think I'll ever be able to like a shaved girl...real women have hair down there.

Now, to get to what you really want to hear about: losing my virginity to my mother. It all started last Friday night. I had just gotten home from my job at the local game store and was trying to decide if it was a night for hacking orcs or blasting aliens. I went upstairs to my room, as usual, and had just kicked my shoes off and set my backpack down next to my desk when I heard my mom's voice float in from the hallway behind me.

"Jim? Is that you, sweetie?"

"Yeah, mom," I called out, sitting down to boot up my computer. "Ms. Kelly had me rearranging storage and doing inventory, so I'm pretty worn out."

I heard the door creak wider open and turned to ask my mom about dinner, but my words collapsed into a gibberish pile on my tongue and I blinked in astonishment. My mother looked gorgeous. Even more so than usual!

She had her thick, reddish-brown locks tied up in the sort of loose, carefree bun that can only be achieved with a great deal of time and care. Her makeup was subtle, but striking; the winged tips at the corners of her thick-lashed, emerald eyes lent her a vaguely cat-like appearance while the deep crimson stain on her plump, pouting lips begged to be smeared from rough kisses and sloppy blowjobs. The delicate crystalline sparkles that dangled at her earlobes caused fairies of rainbow light to dance and play around the sides of her porcelain face. A wide, black velvet choker held a tiny, antique cameo clasped around her narrow throat, it's aged, yellowed surface making it impossible to tell if the brooch was made from bone, or ivory or well-worn stone. The clinging, noodle-strapped, black dress she wore had a subtly sheer quality to it that gave the impression the right lighting conditions could render it transparent and I was almost certain she wasn't wearing a bra underneath. The nearly hip-high slit in the side of the garment showed off great lengths of her nylon-clad left leg, and occasional teases of the fastener for one of my favorite bits of lingerie peeked out of the tempting shadows within. Her simple, dark, silken high-heeled shoes pushed her calves, thighs and bottom up into a gloriously round, bouncy shape and I was hard pressed to remember how to breathe as my eyes hungrily raked up and down this fertility goddess standing before me.

My mouth felt full of dust and several expressions from confusion to mild panic to outright lust fought for control of my facial muscles. My cock tried to surge to life within the confines of my jeans, throbbing uncomfortably in the suddenly constricted space. Had I gotten so exhausted at work that I had passed out in the breakroom and this was all just an erotic fever dream? My brain was almost entirely shut down by the ancient caveman instincts demanding that I take this woman for my own and crush any who would dare stand in my way. I tried to remember what words were, how they could be fashioned together to transmit a coherent thought to the outside world, how language functioned at all, but I failed miserably, and instead merely croaked out a tiny, awe-struck "wow!"

My mom finished adjusting one of her earrings and smiled broadly. "You like it? Your father's taking me out for our anniversary tonight, so I thought I'd try on one of my old dresses." She held her arms out and twisted her body this way and that, then spun in a slow, tight circle, showing off the way the diaphanous fabric shifted and hugged at her curves. "I can't believe it still fits me after all these years. Not too bad for thirty-nine, eh?"

I blinked rapidly and shook my head, trying to kickstart my higher functions into coming back online. "Umm, y-yeah. Yes! Definitely!" I smiled back, hoping she hadn't noticed me eye-fucking her just now, and said, "you look amazing, mom!"

A concerned expression knitted her eyebrows. "Are you alright? You're not getting sick, are you? You look flushed."

"N-no!" I finger-combed my dark hair back from my forehead, trying to regain my composure. "No, I'm fine. Just tired from work and you caught me off guard."

She looked dubious for a moment, but relented. "Anyway...I know you're fine on your own, kiddo. We're going to be out late, so don't wait up for us."

"Yeah, I'm just going to play a bit of something, take a shower and go to bed. Anything in the kitchen I can make myself for dinner?"

"I've left some money on the counter so you can order a pizza or something. Okay?"

"Sounds good. I'll try not to have too much fun." She turned away at the sound of dad's voice calling up the stairs that their cab was here, which gave me a chance to adjust the lump in my pants so I could stand up without embarrassment. "Hang on, I want a hug before you go," I said.

She stepped across the room and wrapped her arms around me, gently resting her head against my shoulder. I held her close, crushing her ample bosom against me and felt the bulge in my pants brush against the soft flesh of her belly. She looked up and puckered her lips at me, wordlessly asking for a smooch. As much as I wanted to get a fistful of her hair and plaster a kiss on her mouth that would kick off a fiery night of intense, passionate lovemaking, I wisely held back with a simple, quick peck and released her. "G'night, Jim. Love you. Be good," she said as she left, tossing me a wave over her shoulder.

"Love you, too," I said following her out into the hall. I leaned over the rail and watched mom glide down the stairs to settle herself into place at dad's right elbow. "Love you, dad! Have a good time."

Dad waved in my general direction, but didn't look up, obviously enthralled by the succubus he had summoned to his side, and said, "yeah, later, son." Mom squeaked cutely and giggled when he pushed her through the front door using a tightly-squeezed handful of her ass cheek.

I allowed myself to stand there and seethe with jealous anger for a few moments after the door clicked shut, silently cursing my dad's good fortune for getting to have my mom as a playmate. Tawdry, lurid visions of what they would be doing together tonight surged and danced through my mind, taunting me as I firmly gnashed my teeth. "Fuck!" I growled, thumping the rail with my fist. I stomped off to the bathroom and twisted the knobs in the shower roughly, furiously wishing I could trade places with him for just one night.

Needless to say, I rubbed one out while washing myself. After drying off, I ordered my pizza and fucked about online, checking my email and Facebook and stuff while I waited for it to arrive. I ate and played some games, working out my frustrations on many digital bug-eyed monsters, and eventually passed out in my chair sometime after midnight.

I was jarred awake by the sound of our front door thumping shut and my mom and dad's inebriated voices laughing and shushing each other. I pried my head up off my keyboard, wiped some drool from my chin, and looked blearily around, taking a moment to get my bearings, then quickly stood up out of my chair and silently tip-toed across my computer-lit room to peek at them through my slightly open door.

Mom and dad were smiling and stumbling together up the stairs, the single fixture in the ceiling illuminating their steps. They were obviously quite drunk judging by the way they leaned on each other for support and struggled with every lurching movement. Dad was carrying mom's shoes with his arm around her shoulders, his tie undone and his unbuttoned shirt wide open. His hair was messy and much of mom's lipstick was all over his lips and neck. Mom's hair had fallen into a disheveled tangle around her oval-shaped face and one of her breasts was bouncing free from the confines of her slinky dress as she clung to the railing with her free hand. They collapsed, standing and giggling together against the wall opposite my door, dad crushing mom underneath him as he roughly squeezed her bare boob and kissed her.

"Quiet," mom huffed out between smooches, "we don't...want...to wake...Jim."

Dad raised his hand to wrap it around mom's throat and pressed his forehead to hers. "Then I'll just have to figure out how to keep you from making noise while I'm fucking you."

Mom gripped his wrist and groaned deeply, her eyelids fluttering as she surrendered to my dad's rough handling, her knees buckling as she rode up and down against the leg he had wedged between her thighs. Dad growled and leaned in to bite on her neck. She blindly felt behind herself along the wall til her fingers encountered the doorknob she was searching for, then she turned it and pushed the door open.

My awakened cock pulsed and throbbed to aching stiffness as I watched them tumble into their bedroom and shove the door closed behind them. I stood there, irritably glaring at the white wooden slab between me and their hot sex. I had to figure out how to watch them! I figured I should probably give them a few minutes to get into things so I wouldn't be noticed, but I was far too impatient and didn't want to risk missing any of the action. Uncertainty froze my hand to my doorknob and I grit my teeth, quietly debating with myself. I really wanted to just barge across the hall and pry their door open, toss my dad to the floor and take mom for myself, but that would be virtual suicide. 'Maybe they would let me join them?' I shook with silent humorless laughter at the thought. 'Yeah, right.'

The door to their room suddenly swung back open and dad stepped into view, his semi-hard dong tenting the front of his boxer shorts. "Hang on, sweetheart! I gotta piss," his words slurred towards the darkened room behind him. He wobbled his way up the hall, easing and leaning along the walls towards the bathroom. There was some thumping and shuffling sounds as another door opened, a liquid rush of splashing noises and then the flushing whoosh, a squeak, a clatter and a hard, whumping thud followed by silence.

'What the hell? What did he just knock over?' I waited for a few moments, expecting to see him go back to his bedroom, but nothing happened. After nothing continued to happen for another couple of seconds, I started to worry that noise might have been something serious. The seconds collected into minutes and I decided I should check on him. I eased out of my room and around the corner. I could see dad's feet sticking out into the hall. A few mincing steps closer revealed his entire mostly-nude form, splayed out face down in front of the toilet, mom's basket of lotions, perfumes and makeup samples scattered around him. I rushed over and shook his shoulder, frantically looking around for signs of injury. I urgently whispered at him. "Dad? Are you okay?"