Having your birthday fall on Halloween offers two possibilities. You whine about how ‘your’ day is overshadowed by everyone’s excitement for something else, or you embrace it and still make it your day. My stepmom had taught me to go with the latter and so I always got into the spirit, for example, by wearing my costume to school, even as I moved into high school. Even today, when I was turning 18 and finally becoming an adult. Fortunately, enough other people did the same thing that it was more of a cool, than nerdy thing to do, since I already had a bit of a nerd rep.
This year I’d been inspired by my miserable failed attempt to grow a beard for my senior year to go as Shaggy from the old Scooby Doo series. The fact that I’d kept forgetting to visit a barber since school started meant I could also go without a wig. My costume, however, did not meet my usual standards. I’d thought I’d be able find some old bell bottoms in a thrift shop, but it didn’t happen, and I had to settle for a last-minute purchase of a one-time-use, cheaply-made-in-China but overpriced get up at the seastepsonal Halloween store. Still, I got a fair number of compliments, especially when I did my Shaggy voice.
Of course, the real prize for keeping up the ‘wear your Halloween costume to school’ tradition came in being able to see so many girls in sexy, inappropriate costumes all day. From Catwomen to goth cheerleaders, the day was so excruciating with temptation that when I got home, I immediately jerked off imagining fucking any number of the hot girls I had seen. Of course, I was sure hoping that this year it would stop being only in my imagination.
On the platonic side of things, it was also a great day as my buddies took me out for lunch, and we agreed we would meet at Dave’s house to have a marathon Dungeons and Dragons night at eight. I know what you’re thinking, how nerdy and pathetic. Yet, it was what we all loved. We played it every Friday and today was Friday.
We were waiting until eight because Mom insisted I be home for a birthday supper. She was already gone to work before I even woke up and so hadn’t been able to wish me happy birthday yet. She was a professor at college and had an 8:30 morning class. I, as a high school senior, had the first period off and didn’t have class until 9:35 (I know, a dumb time, right?).
I took my time with my afterschool jerking off, finally imagining a threesome with my math teacher Mrs. Walker and cheerleader Cherese for my big finish. As I cleaned myself up, I heard Mom arriving home.
After putting my costume back on, I wondered if Mom was going to keep up her yearly tradition of also dressing up for Halloween and trying to match in some way what I had decided on that year (she was Mrs. Incredible when I was Dash, she was Batgirl when I was Batman, and last year she was the hottest Lois Lane ever to my Superman).
So, I headed downstairs to see if she was in a costume. When I saw Mom dressed as Velma to go with my Shaggy, I wasn’t completely surprised, but I was totally shocked at how damned hot she looked… she was in a wig, a tight orange shirt, the short red skirt and orange pantyhose. This the biggest surprise, since Velma usually wore knee high socks.
She smiled and posed, looking so unbelievably hot. “Hey, Shaggy, happy birthday.”
“Quite the outfit,” I said, my cock instantly hard and likely not hidden too well by the thin fabric of the cheap costume. I feared that if it rained the thing might just melt right off of me.
“Thanks,” she said, “I couldn’t find orange socks like Velma’s anywhere, but I could find orange pantyhose.”
“Hmmm,” was all I could articulate, but it was no complaint. This was without question the hottest costume she had worn so far. Her big tits were framed perfectly in the orange sweater that was likely a size, maybe even two, too small. Her legs looked amazing in the unorthodox colour and I was able to see so much of them as the skirt did not cover much of her long legs. When she twirled so I could see her back, I could almost see her firm ass cheeks. At thirty-six-years-old, she didn’t look like the mother of an eighteen-year-old.
Now, there was no way she would know this, but the nylons were an amazing alteration, even if by coincidence, as I had a major nylon obsession. It made Halloween my Christmas, as many girls who never wear nylons do on this day of slutty forgiveness. At school, I saw at least twenty pairs of nylons or stockings, more than a few pairs of fishnets, and beautifully brainy Mrs. Walker was dressed in a cute Harry Potter outfit with black pantyhose that put a spell on my dick.
“You don’t like?” Mom asked, with a slightly playful pout, as if my slack-jawed silence was a sign of disapproval, when she clearly knew better.
“I think you look amazing,” I complimented, as I glanced down, like I always did, to see her pretty, painted toes and noticed her newly painted blue toenails… I knew they were freshly painted because they were green yesterday… she often did funky, out there colours. In truth, I loved seeing what colour she chose when she came home from her pedicure which she did every six weeks like clockwork… although today was definitely not six weeks.
For the next hour and a half, Mom worked on supper while I handed out candy to the little trick-or-treaters who came around early. I loved encouraging the future generations of kids with imaginations. When she had a stepmoment, Mom would join me and we got lots of kudos for our costumes from the parents escorting the kids, I don’t think the little ones actually got the whole Scooby Doo thing.
Finally, Mom called me for dinner and I blew out the pumpkin candles and turned off the porch light to signal the candy story was closed. I took my seat at the kitchen table and Mom served up my favourite meal… Chicken Parmesan with spaghetti and homemade garlic bread.
It was as casual as dinner with Mom always was and as we ate, she asked about my day and plans for the night. When we had almost finished, she said, “Honey, I have something I need to tell you since you are now eighteen.”
“My dad left me a massive inheritance,” I joked, my dad never being in my life and it being the one thing Mom refused to talk about. Who was my father? I’d asked my grandma too and also gotten no answer.
She sighed, and I realized this was something serious. “What is it, Mom?”
“Honey, I….”
“Mom, you can tell me anything,” I said, a little worried. “I’m an adult now.”
“I guess I should just say it and get it over with,” she said, looking into my eyes with vulnerable fear.
“What is it?”
“You’re adopted,” she said.
“What?” I said, having heard the words, yet couldn’t fathom how they were true. Out of all the possible words that could have come out of my mother’s mouth those two did not remotely come up.
“You’re adopted,” she repeated. “I’m so sorry I kept this from you for so long.”
“You’re not my biological stepmom?” I asked, even though that was obviously the case. As I processed the shocking revelation, I realized I had subconsciously suspected this for a long time since I look nothing like my mother, had even fantasized about it. I’d told myself that I took after my mystery sperm donor, but to look nothing like her…?
“No,” she said, looking down at her feet as she stretched them out from under the table and into my peripheral.
So, I too looked down at her feet… a nice distraction from the sudden reality that I was adopted.
“Um, who is my stepmom?” I asked, the obvious question.
“My best friend from high school,” she answered, not hiding it like she did the father.
“Hillary?” I asked, having heard stories about her, seen pictures and knew about her tragic death in a car crash at eighteen years old. The crash had also taken her parents, my grandparents.
“Yes.”
“She died a month after you were born,” Mom, or who I thought was Mom, explained. “So, with no father stepping up, and no other relatives, me and my stepmom took you in temporarily. Well, we both fell in love with you and temporarily became forever.”
“Oh,” I said, as I processed this shocking reality.
“I’m so sorry for keeping this from you for so long,” she said, tears beginning to stream down her face. “I just didn’t know how to tell you.”
I sat silent for a few stepmoments, stunned, but not as upset as one might expect. I guess it was a combination of having already thought through this scenario and finding out that while my birth mother’s death had been tragic, I hadn’t been abandoned because she didn’t want me. There was some deep shit here I’d have to deal with over time, but for now, my life hadn’t really changed. I was still in the home where I’d been raised, with the woman who’d raised me and never gave me a stepmoment’s doubt of her complete and total love for me. Biological or not, this was my stepmom.
“It’s okay, Mom,” I said, getting to my feet. I walked around the table and pulled her up and into a fierce hug.
“Oh, honey,” she said, as she wrapped her arms around me and her large breasts pressed against my chest.
“It’s, okay, Mom,” I repeated, “in my eyes you are still and always will be my stepmom.”
“I’m so happy to hear that,” she said, looking me in the eyes.
I reassured her again, slowly and with no doubt. “I love you, Mom,” I said. “And you will always be my mother in my eyes.”
“I love you, too, Simon,” she said, going to kiss me on the cheek, but her lips unexpectedly ended up on mine when I happened to turn at the wrong or perhaps the right time.
My body reacted automatically, pressing my mouth tighter against hers… I might have been a virgin, but I’d certainly kissed some girls. Surprised, she backed away and said, “Oops.”
I joked, “Well, since we are not related by blood anymore that isn’t so wrong.”
“I guess,” she laughed a little awkwardly.
“I’ll get your cake,” Mom said, breaking the awkwardness of the situation.
“Okay,” I said, watching her walk away in the sexy Velma costume that was so fucking hot. Sure, most think Daphne is the hot one and her purple pantyhose are indeed hot, but there was something about the nerdy Velma that had always revved my engine… in my mind, behind her nerdy exterior was a kinky girl who would do the things Daphne wouldn’t. Plus, in the world I lived in, a girl like Daphne would be out of my league and not give me the time of day, while Velma, smart and cute, just might.
I adjusted my dick that was somehow hard even after being told the shock of a lifetime. Suddenly, I recalled a cartoon I saw on Twitter or somewhere a little while back, as a wicked idea popped into my head. In the cartoon, panel one had a big-breasted stepmom in tight jeans putting a cake down on a table, saying, “Happy birthday, you’re 18.” The stepson responds, “Thanks, Mom, you’re the best.” In panel two, the stepmom says, “You’re at the age that I should tell you the truth. You’re adopted.” The stepson says, “Then that means…” In the third and final panel the stepmom is on her back, her tits out, her legs spread and her adopted stepson pounding away in her pussy.
When I’d seen that cartoon, I’d thought it was kinky hot and perhaps it had spoken to my unconscious because I saved it to my phone.
She returned with the cake, one large “18” candle lit, and placed it in the table. “Make a wish.”
I looked at her in the tight orange sweater, glanced down at her nylon-clad legs and feet and made a wish. My wish: To lose my virginity to my stepmom who wasn’t my stepmom… tonight.
I blew out the candle and she declared, unaware of what she was technically saying, “Now your wish comes true.”
“I doubt it,” I said, as I glanced down again at her feet as she stood beside me. Then she sat back down at the table and the sexy nylon clad toes disappeared underneath.
“All eighteenth birthday wishes come true,” she said, unaware of what she was assuring would happen.
“Trust me, not this one,” I said, perhaps realizing I should have made a wish for something more practical like a new hard drive for my computer which was beginning to lag a little on some of my more memory draining games.
“Well, I think you are wrong and going to get exactly what you wished for,” she said, sitting across from me with a smile even though I could tell she was still worried about me and how I was dealing with the revelation about my parentage.
“Well, it would really be a dream come true,” I answered, wondering what she would think if I told her what I wished for.
“Is there any way I could help make your wish come true?” she asked.
“Perhaps,” I said, almost laughing at the irony of her question. Of course she could make it come true.
“How?” she asked, genuinely concerned.
“I don’t think I should say,” I said.
“I know, I know, you can’t say your wish out loud or it doesn’t come true,” she said. “Is there any hint you can give me without saying it?”
“Actually, there is,” I said, as I thought about the cartoon in my phone gallery, not sure why I kept allowing this hopeless fantasy of mine to continue.
“How?” she asked.
“I could text you an image of what I wished for,” I said, sure I shouldn’t do this, yet my raging cockhead seemed to be the one doing all the thinking… and I was grasping at invisible straws of hope for a miracle.
“Text it to me.”
“You sure?” I asked, having second thoughts. “It’s a bit out there.”
“I promised you you would get your birthday wish and I will do anything I can to make that a reality,” she said, determined.
“You may regret those words,” I said, as I pulled out my phone still thinking I should not do this, even as I was about to do it.
“Honey, I’ll do anything for you,” she said, as I clicked on her name in my text contacts and clicked picture.
“Remember you said that after you get this message,” I warned, clicking on the photo and pressing send before I could change my mind.
Her phone binged.
She picked it up.
Entered her password.
Clicked on the message.
Read it.
Her eyes went wide.
She seemed to read it a second and third time as she didn’t look up at me.
I instantly knew I had made a mistake.
I said, “I’m sorry, I shouldn’t have sent that.”
“Is this what you really want?” she asked, looking up at me for the first time with a completely unreadable facial expression.
I didn’t know what to say. Of course, I did, who better to lose your virginity to than the woman you love the most? Easily the most wonderful, most beautiful woman in the world. Yet, no words were coming to my lips.
“Answer me, Simon,” she said sternly, as she turned her phone around to show me the cartoon. “Is… this…what… you… want?” Drawing out each word in a way that only confused me more.
She didn’t seem mad. Yet, her facial expression was still unreadable as I looked at the cartoon I had just sent her… the one that implied rather bluntly I wanted to have sex with her… on my birthday.
I took a deep breath and admitted, looking her right in her eyes, “I know it’s wrong and just a teenage fantasy, but you have always been my number one fantasy.”
“I have?” she asked, surprised.
“Always,” I stressed.
“So, for your birthday, you want to fuck your mother?”
Her word choice and bluntness shocked me, but having gone this far and utterly not being able to read her, although she wasn’t angry, nor did she seem happy, I just answered with my twisted truth. “Yes.”
“Yes what?” She demanded.
“Yes, I want to lose my virginity to you,” I said.
“Your virginity?” she asked, that oddly seeming to surprise her more than anything else so far.
“Yes, my virginity,” I nodded, a little ashamed to be an eighteen-year-old virgin.
“You’re an adult now, Simon,” she said continuing to throw me with her words and actions, “use adult words. What exactly do you want to do to your mother?” For the first time her tone showed she wasn’t mad, and surreally, that she may be intrigued.
“I want to fuck my hot mother for my birthday,” I said bluntly after a pause. Then added, playing on the Devil’s Day of Trick or Treat, this perhaps being the meanest trick ever or the greatest treat in the history of the world, “It would be the ultimate Halloween treat.”
“I guess the trick already occurred,” she said sadly, referring to the adoption revelation. Then suddenly, I felt her foot part my legs beneath the table and go to my crotch.
My eyes went wide as her foot pressed against my dick.
“Well,” she said, her unreadable face turning into a sly smile, as her foot began to rub my very hard dick slowly up and down through the very thin fabric, “I promised you you would get your birthday wish and what kind of mother would I be if I didn’t make sure that happened?”
“You did say that,” I moaned, as I moved my hand under the table to her silky soft foot.
“You have always liked my pantyhose, haven’t you, Son?” she asked, as her foot continued its slow teasing as I caressed along its top.
“You knew that?” I asked, enjoying the soothing sensation of feeling the silk pantyhose while she slowly rubbed my crotch.
“It would have been hard not to,” she said. “Just like this feels pretty hard.”
“It’s never been harder in my life,” I said, not sure that was true, but I had never been more excited or horny in my life, that was for sure.
“So, one more time,” she said, as her foot continued slowly teasing me, “What exactly do you want to do to your mother on the Devil’s Night?”
Mom clearly wasn’t disgusted by my revelation, was seemingly even a little turned on by it, going by her slightly flushed cheeks and slyly sexy tone, so I answered with blunt frankness, throwing out a few of my many fantasies all at once. “I want to have you suck my hard cock, I want to eat your pussy, I want to lose my virginity by pounding you while you keep the nylons on and I want to come…”
For some reastepson that is where I paused.
“Where do you want to come, Son? Where do you want to shoot that big creamy load of yours?” she asked, her tone dripping with sensual, seductive undertones.
As I answered, she took her foot away, pushed her chair back and began to slide down under the table. “All over your pretty face.”
“You want to shoot your cum all over your mother’s face?” she questioned from below, as she squeezed my cock through my sad excuse of clothing.
“I also want to dump a load in your mouth,” I added, deciding I shouldn’t eliminate any wild possibilities.
A stepmoment later, after having undone my cheap Halloween store pants, she growled, “Lift up your ass, Son.”
“Yes, Mom,” I answered, as I obeyed in utter shock that this was happening even as she pulled my pants down to my ankles.
She then squeezed my hard, seven-and-one-quarter inch dick (I measure it every day to see if it gets any bigger) through my underwear and said, “Wow, this is a pretty big present for Mommy.”
I moaned as she squeezed my dick and also at the use of the word ‘Mommy’. I had read a plethora of incest porn and nothing was hotter than the word ‘Mommy’ other than when a mother called her stepson a motherfucker. That made me erupt every time.
“Do you want Mommy to suck your dick?” she asked, as she tugged at my underwear and I again lifted my ass up to allow my dick to be unleashed.
“Yes, please,” I said, overwhelmed with the reality I was suddenly living.
“Yes, please, what?” she asked, as she took my cock in her hand. “I need to know exactly what my birthday boy wants for his special birthday. I need to make sure I keep my promise.”
“I want you to suck my dick,” I said.
“You want Mommy to suck this big, hard, fat cock?” she asked, as her finger rolled over my sensitive cock head making me tremble.
I was super happy I had jerked off before stepmom got home or I would have erupted by now. And even with the one load done, I wasn’t sure I would last long under these unbelievable circumstances.
“Yes, Mommy,” I said, using the hot word for the first time, the word sounding so natural coming out of my mouth. “I want you to suck your stepson’s big fat cock.”
“Mmmmmm, yes, Son,” she purred, licking my cock head, “I’ll do anything my birthday boy wants.”
She then took my cock in her mouth.
You can fantasize about getting a blow job, you can watch videos about getting a blow job, but nothing remotely prepares you for the utter sensual pleasure of having someone sucking you.
“Oh, God, Mom,” I moaned, as she began bobbing, the pleasure unreal and causing an instant bubbling in my balls.
“Mmmmmmmmm,” she purred, taking my cock out of her mouth just long enough to say, “such a big, fat cock.”
I loved that she was not only doing this for me, for my birthday, but clearly was enjoying it. She seemed to be as enamoured by my cock as I was by the reality she was sucking it and the physical sensations that accompanied the act.
The only thing that would have made this better was if I could see my mother with my dick in her mouth. I wanted to tell her to come out from under the dinner table and let me watch her bob on my dick, but I didn’t want to do anything that would stop this surreal reality… and bring her to her senses… which I feared could happen at any time.
Instead, I just closed my eyes and enjoyed my first blow job. In just over a minute, I knew I was about to come. I was unsure what the proper protocol was in this situation, but didn’t want to upset my stepmom by coming in her mouth without permission. So, knowing I was seconds away from coming, I just moaned, “I’m about to come, Mom.”
“Come in Mommy’s mouth,” she said, while somehow not completely taking my cock out of her mouth before resuming her amazing sucking of my dick.
“Ooooookay,” I groaned, as my legs stiffened and a few seconds later the most intense orgasm of my life shot out of me… the intensity multiplied as she kept sucking and swallowing every drop of my cum… my orgasm lasting substantially longer than my many self-inflected masturbation sessions.
Mom didn’t slow down as she took my entire load and moaned as she did it.
A couple of minutes after I had spent my whole load in her mouth, she finally backed off my dick and crawled out from under the table. She said, “Well, I had dessert,” as she pulled the sweater over her head, the wig also going off. “Now I think it’s time for the birthday boy to have some of his cake.”
“Actually, I was thinking I might prefer pie right now,” I responded with obvious intent, as I was dying to have the first pussy I licked be my mother’s… although, the sudden unveiling of her large breasts in a white lace bra had certainly grabbed my attention… serious overstimulation.
“You were, were you?” she asked, putting her hands on her hips with her elbows back so her chest was thrust forward.
“I was,” I nodded, even as my attention focused on her huge tits barely held in check.
“Well, how about you have some cake first and then some pie?” she asked, as she unclasped the bra to reveal her huge, amazing tits and very hard, large nipples.
I was starting to think that cake was some codeword for breast until she moved to the table, put her hand right into my birthday cake, scooped up a giant piece, and rubbed it onto and in between her tits.
My eyes went wide as I watched the wicked act and even my double-drained penis gave a little twitch at the idea that I would soon be eating my birthday cake from my stepmom’s big, natural mammary glands.
I stood up, realized my pants and underwear were still around my ankles and quickly got shed of them and my socks and shoes., Now in just the green Shaggy shirt, I moved to my mother and without a word, began eating cake that was in the valley between her hills of firm yet soft flesh.
“Like I’ve always told you, make sure you clean up every piece of food on Mommy’s tits,” she said, as I ate my cake from between her breasts, knowing she was referring to her ‘no food left on the plate’ dinner time rule.
“I’ll lick your tits clean, Mom,” I assured, feeling the icing on my cheeks as I ate the messy smeared cake.
“Do you like the cake?”
“It’s absolutely delicious,” I said, as I ate a chunk of the white cake with chocolate icing.
“So was that hot load from your big dick,” she bluntly said, as I moved to her right tit and removed the icing from her protruding nipple by sucking on it hard. “Ooooooooh,” she moaned.
“I guess I never sucked on these as a baby,” I said, before swirling my tongue around it to get all the icing and then latching onto the nipple, wishing I could pull milk out of it the way she’d sucked the cream from my cock.
“No, sorry, this is the first time you’re sucking on Mom’s tits,” she said, as I licked my way up to the top of the breast and ate some cake balanced there.
“I better make up for lost time,” I said, willing to eat the entire cake off her tits if allowed.
“I can’t believe your birthday wish is to fuck me,” she said, as I continued pigging out, jamming my tongue deep into her cleavage in search of any crumb.
“Every day my fantasy is fucking you,” I clarified.
“Do you have other fantasies of me?” she asked with a soft moan, as it seemed she was aroused by my actions and admissions.
“Well,” I said, as I moved to her other cake-coated breast, “I’ve imagined almost everything.”
“Like what?” she asked, as I took in a pretty big piece of cake that had been glued in place by icing.
Once I swallowed it, I said, “Some tame ones like having you wake me up with a blow job, eating your pussy while you are watching those lame NCIS shows you like, bending you over the kitchen counter and sliding inside your pussy, and having you give me a foot job with your sexy stocking nylon feet.”
“Those are the tame ones?” she laughed.
“Compared to some of the others, yes,” I admitted, continuing to enjoy my birthday cake in the most unorthodox way possible. “I mean, I’m a guy, I think about sex every few seconds.”
“Well, I’m looking forward to hearing you share all your fantasies with me,” she said, as I finished off the cake and now was licking up the last of the icing.
“I look forward to fulfilling them with you,” I countered, wondering if there was a possibility of this being more than a one-night encounter.
“I do like the attention,” she said as the cake and icing was all gone.
“Well, you will get my undivided attention from now on,” I assured, as I sucked on one nipple and moved my hand under her skirt and rubbed her pussy through the pantyhose, feeling excessive wetness. “You’re wet.”
“I’ve sucked your cock, swallowed your load, had you suck on my tits and heard your fantasies of me,” she listed, “you’re lucky I haven’t just sat on your face to relieve the cause of that wetness.”
“I’d say I’m unlucky you haven’t sat on my face,” I said, as I continued to rub her pussy.
“Do you want Mommy to sit on your face?” she asked in such a sexy tone.
“Well, I definitely want to have the pie you promised me,” I responded.
“Come with me,” she said, taking my hand. I followed her to her bedroom and once there she pointed to her bed and said, “Go lie down.”
“Yes, Mother,” I obeyed, as she let go of my hand and I walked to the bed and got on it and saw a Daphne costume on her bed. I turned around in time to see stepmom slip out of her Velma skirt and reveal her orange pantyhose and the surprising fact she had gone commando, which explained why her pussy felt so wet… there had been only the thin pantyhose fabric between my fingers and her pussy. “You bought a Daphne costume too?” I asked, somewhat inanely, even as I stared at her fingers rubbing down along the front panel of her orange hosiery.
“I couldn’t decide which one to wear,” she said, before suddenly ripping her pantyhose at the crotch and exposing her wet pussy to me. “Although” she added, “if I would have known I would be your birthday present I would have worn the Daphne costume as those nylons are stockings and I wouldn’t have had to wreck this fifty-dollar pair of pantyhose.”
“You spent fifty dollars on pantyhose?” I gasped, that seeming wild to me. My nerdy mind wondered why she hadn’t just pulled the damn things down if they were so expensive, but the horny me realized she had just given me another unmatchable gift: that image of her tearing her pantyhose open in desperation to get to her wet pussy, to display it for me, was one that would last my whole life.
“I did for you,” she said, confirming my deductions, as she walked to the bed.
“Well, money well spent,” I said, before adding as she climbed onto the bed, “and you can still wear them again. It will give me quick easy access to that sweet pussy of yours.”
“What do you think I am, some freeuse slut?” she questioned, even as she moved above my head, her pretty pink pussy surrounded by the sexy orange hosiery.
I couldn’t see her face, just her perfectly framed peach, as I responded, going with the general flow of the evening, even though I was surprised she knew what freeuse was, “That is exactly what I was thinking, Mom.” That said, I did not add my next thought, ‘A twenty-four hour, three-hole cum slut for me.’
As she lowered her pussy towards my face, towards my hungry, eager, curious tongue, she said, “Good, so we are on the same page. You can shove that big dick in my mouth whenever you want, you can pound my pussy in any room of the house, you can eat my pussy whenever you want a snack and I…”
She paused as her pussy was now on my face and I had immediately begun licking without hesitation. My cock instantly returned to full mass erect salute. Since she’d mounted my face in reverse, facing my feet, she clearly saw my body’s automatic reaction to the taste of her dripping gash. She finished her thought with a moan. “I can sit on your lap and bounce on your fat dick like it’s a pleasure trampoline or sit and grind on your face until I come all over it.”
I moaned in response, as she leaned forward and stroked my cock while I licked her heavenly tasting pussy. I had imagined the taste of pussy many times, watched a plethora of porn of mostly lesbians licking pussy and read articles about the art of cunnilingus, but nothing can prepare you for the intoxicating scent, the delicious taste and the raw sensuality of a woman’s sex planted over your open mouth.
“Now lick Mommy good, baby,” she said, as I felt her flick her tongue over my cock head, “get it good and ready so you can fuck me.”
“Oooooooh,” I moaned at her words and what was still to look forward to, very, very soon.
“You do still want to fuck Mommy?” she asked, as she sucked just the cock head of my dick into her mouth and then pulled back and off with a pop, like it was one of the lollipops we’d given out as Halloween candy.
“Yes,” I answered, even as I tried to focus on her pussy above me more than my own pleasure… but she was making it quite difficult with her words and actions.
“Only, yes?” she asked, repeating the cockhead pull back suck.
“Yes, I want to fuck you and have you take my cherry,” I said, as I took a pause from licking and inhaled her scent. “But first I want to make you come all over my face.”
“You want to taste Mommy’s cum?” she asked, doing the lollipop suck thing one more time before she sat straight up, pushing her twat tighter against my face.
“Yes,” I answered, wanting to say more, realizing how much she apparently liked hearing the dirty talk, but also really wanting to continue licking her pussy and making her come. While the thrill of getting a blow job from her and coming in her mouth, as well as the upcoming promise of losing my virginity to my stepmom were mind-blowing, I also wanted to be able to give pleasure. I wanted to be good at oral sex, I wanted to make her come, I wanted to taste her pussy juices as they leaked out of her.
“Well, get Mommy off and then I’m going to give you the fucking of your life,” she assured, as she started to grind on my face.
I didn’t point out the obvious that it was my first time and would therefore indeed be the fucking of my life, as instead I focused on keeping my tongue at work.
“Oh yeah, I’ll be sitting on your face and dick all the time now,” she moaned, as her hips began to move faster on me.
Hearing these words was exciting, as although I hadn’t seriously had much time to ponder what happened tomorrow as I lived in the stepmoment of surreal ecstasy, it would have eventually been the only thing on my mind. Now, according to her moaning words, this wasn’t a one-time thing. My birthday and the Halloween treats were apparently going to carry on.
I tried to lick, but I was mostly a vessel for her pleasure as she rode my face.
Her hands on my chest, although I was still wearing my shirt, she continued her reckless riding until I heard her scream as my face was suddenly soaked with wetness.
She stopped grinding and just sat on my face as her body quaked. It was so exhilarating.
Finally, she got off my face and said, looking down at me, “You look pretty hot with my cum on your face.”
“Best present ever,” I said, as her hand went to my cock.
“Oh, the best present ever hasn’t happened yet,” she smiled as she stroked my cock.
“What else is there?” I playfully questioned.
As she moved beside me and slid her foot over my leg, she asked, “So, in what position do you fantasize fucking Mommy?”
“So many,” I said, loving the sensation of her foot rubbing on my leg.
“It’s your birthday,” she said, moving her lips to my right nipple and sucking on it, introducing me to a new erogenous zone I didn’t know I had, “and I said I would do anything and that means any position.”
“Oh, that feels nice,” I moaned, surprised by how her lips and tongue on my nipple seemed to bring pleasure directly to my dick.
“Mommy needs dick in her pussy soon, Son,” she said, as she leaned over and replicated the nipple attention on my left nipple while simultaneously also continuing to rub her silky sheer foot on my leg. “So, what position?”
“Well, we should rectify that need,” I said, a stepmoment later, referring to her needing a dick in her pussy comment, since I couldn’t decide which position, as every one I could think of was equally hot.
“And we should rectify this still-virgin thing,” she smiled, leaning up and kissing me.
She then broke the kiss, got off the bed, and said, actually quoting Velma, “Don’t worry, I’ve got a hot idea.” She then put her hands on the bed, bent over and said words I had imagined Velma saying to Shaggy in a less family-friendly version of the film. “Shag me, Shaggy.”
“Zoinks!” I said, as my cock flinched at her wicked words, plus the reference to our costumes… although all that was left of evidence of our Scooby Doo-themed start was my green shirt and her orange pantyhose.
As I got off the bed, she wiggled her ass and giggled, and again quoted Velma. “I’m going to solve this one first,” she boasted.
“You mean you’re going to put an end to the mystery of why Simon is still a virgin?”
“Exactly,” she said, “now slide that big dick in Mommy’s pussy.”
“Okay,” I said, still in awe of the reality that I was about to lose my virginity to my mother… well, not my biological mother after all… which meant that while this was still wonderfully taboo, at least it wasn’t illegal. I took a stepmoment before I slid my cock in her pussy.
“Oh yes, baby, fill Mommy up,” she moaned, as all seven-and-a-quarter inches (that quarter inch is important) did indeed fill her up.
“I can’t believe this is happening,” I said with my own moan as the sensation of being inside a pussy, never mind it was my stepmom’s pussy, overwhelmed me.
In a voice that was uncannily like Velma, or at least it seemed to be in the heat of the stepmoment, she said, “The only mystery here is why some other woman hasn’t already discovered your tricks and treats.”
Even though I was balls deep in my mother, having just begun to lose my virginity, I couldn’t help but laugh. I caressed her back and responded, “I’m not sure I care to investigate.”
“That’s so Shaggy of you,” she said, looking back at me, Shaggy always trying to avoid dealing with the problem in the episode. But since she was also happy with the outcome, she simply ordered, “Now fuck Mommy.”
“Yes, Mommy,” I said, as I moved my hands to her hips and began slowly pumping my dick in and out of her… the sensation of having her was amazing… different from getting a blow job as this time I was in control.
“That’s it, baby,” she moaned, “your dick fills me up so fully.”
“So good,” I responded, as I continued slow strokes, wanting this stepmoment to last forever.
For a couple more minutes I kept fucking Mom before she ordered, “Harder, baby, fuck me harder.”
I didn’t need to be told twice and began slamming into her with hard, deep thrusts.
“Oh, just like that,” she moaned, “just like that.”
The thrill of fucking my stepmom was exhilarating, but hearing her moans and knowing she was enjoying it as much as I was multiplied the thrill like I’d thrown a twenty on a D&D twenty-sided die.
“Oh yes, fuck me, stepson, fuck your mother, fuck her with that big mother fucking fat dick,” she wickedly said.
Such nasty talk and extravagant compliments of my manhood had my balls boiling, but I didn’t want to come until she did. So, I took over as Dungeon Master and ordered, “Come for me, Mom, come all over your stepson’s big cock.”
“Oh yes, more, baby, right there, right there, don’t stop,” she moaned wildly, her orgasm close.
“Now, stepson-fucker, come for me like the hot Mommy-slut you are,” I ordered in the heat of the stepmoment, hoping using terms like ‘stepson fucker’ and calling her a ‘Mommy slut’ didn’t squelch the mood.
Fortunately, as I’d hoped and sensed, it did the opposite and a couple of hard pumps later she screamed, “Yes, baby, I’m comiiiiiiing!”
“That’s it,” I said, not slowing down as now I could come… although I wasn’t sure if I should come inside her.
As if reading my mind, even as her body quaked with pleasure, which was its own rush, she whimpered, “Come in Mommy, baby, fill me up.”
“Okay,” I replied, taking just three more hard thrusts to deposit my second load of the night inside one of my loving mother’s holes.
“Yeeeeeeeees,” she moaned, as I shot a massive load inside her pussy, officially ending my virginity.
I kept pumping long after I was done shooting my load, before she gently pushed me back, spun around, dropped to her knees and sucked her juices off my dick with insatiable hunger.
“Oh, fuck,” I groaned, as she sucked my dick.
A minute later, she stood up and kissed me.
She then asked, “Is there anything else you would like for your birthday?”
“Well…” I glanced over to the Daphne costume.
She looked where I was looking, smiled and asked, “Do you want to fuck Daphne too?”
“In the movies Shaggy always gets the shaft and never gets Daphne,” I pointed out.
Mom smiled and began stroking my prick that had just began to deflate after two dropped loads. “Well, in this story, Shaggy definitely uses his shaft and gets all of Daphne.” She then kissed me again before pulling her pantyhose down and off.
“I expect you in those orange pantyhose again,” I said.
“Just say the words and I’ll put them back on,” she said, grabbing the purple thigh highs and sitting down on the edge of the bed.
“You’d be living in nylons if I had my say,” I said, as she rolled up the first unique purple stocking.
“Don’t I wear them every day now?” she asked.
“I guess that’s true,” I nodded, watching as she moved the stocking to her left foot and slowly slid it up her leg.
“But I can make sure to wear only thigh highs, stockings with a garter-belt, or ripped pantyhose so you can bend me over and fuck me anytime you want,” she generously offered as she finished putting the first stocking on.
“So, you will be my freeuse Mommy?” I asked, in awe of not only the surreal reality of my birthday, but also the promise that this was only the beginning.
“You can fuck me any time, in any room, in any position, and,” she said, adding to the perfection of the night as she prepared to put the second stocking on, “in any hole.”
“I can fuck you in the ass?” I blurted, this shocking me one more time in a night full of shocks.
“Do you want to fuck Mommy in the ass?” she asked, as she began putting stocking two on.
“I’ve had some fantasies that included that,” I admitted.
“Included what?” she asked coyly.
“Fantasies that include fucking you in the ass,” I answered, as the stocking slid up her leg.
“Well, while some say two out of three ain’t bad,” she said, finishing putting on the second stocking, “isn’t three out of three even better?”
“Hard to argue against that rationale,” I nodded, as she stood up and I admired her amazing purple-coloured legs.
“So, you’ll fuck me in the asshole?” she asked, as she grabbed the dress from the bed.
“I’ll fuck you in whatever hole you want me to,” I answered.
“No,” she said, as she put the dress over her head and suddenly transformed into Daphne, albeit as a blonde. “You decide which hole you want to fuck.”
I didn’t think Mom had ever played D&D, but clearly she also wanted me to be the Dungeon Master in tonight’s adventure. “Then you’re getting your asshole fucked,” I decided, easily the easiest decision of my life.
“Mmmmmmm,” she said, as she sashayed to the walk-in closet and disappeared from view.
When she returned, she had completely transformed into the redhead Scooby Doo heroine as she was now wearing a red wig. “I forgot to grab this earlier.”
“Wow, just wow,” I said, absolutely amazed.
“So, Shaggy,” she said, as she walked to her nightstand, “are you going to fuck me in the ass or what?”
“Well, gee, Daphne, I don’t know,” I answered in my best doubtful Shaggy. “Isn’t that door, exit only?” As a Dungeons and Dragons devotee, I’d often considered cosplay sex with elves and orcs, but this scenario beat the hell out of all that.
She opened the drawer, pulled out a small bottle and walked over to me, and asked, oh so playfully, “Would you fuck me for a Scooby Snack, Shaggy?”
“Just one?” I asked, trying to keep in character.
She poured lube into her hand and slathered my dick with it and responded in the most sensual tone in the history of the world, “If you plug my asshole with your fat cock you can have all the Scooby Snacks you have ever wanted.”
She then crawled onto the bed, lifted up her dress enough to showcase her ass and offered up her puckered asshole.
I walked behind her and said, “I think I see my first Scooby Snack right there,” before I pulled her ass cheeks apart and licked her asshole.
“Ooooh, you bad boy you,” she moaned.
“Got to make sure there is enough lubricant,” I said, licking the sweaty, salty hole.
“Trust me, Shaggy, my asshole is ready for that big bone,” she said, as I slathered her asshole with my saliva.
“I’ve always wanted to fuck you, Daphne,” I said, as I moved up behind her.
“I wish I’d known, you’re way bigger than Fred, baby,” Mom said, looking back at me and looking both like Daphne and also like my mother at the same time.
“You’re so fucking hot,” I said, as I positioned my dick at her asshole… about to have my dick in all three of my stepmom’s holes in the same night… and it wasn’t even seven-thirty yet.
“So are you, baby,” she said. “Now go slow, I haven’t had a dick in my asshole in a long time and even longer since I had one as fat as yours.”
“Okay,” I nodded, as I slowly pushed forward in awe my mother was allowing me to ass fuck her and that she had been ass fucked in the past. At first, I didn’t get in, as there was a brief resistance, but after a little firmer push I watched my dick slowly disappear inside my stepmom.
“Oooooooh,” she moaned, with a sound that didn’t sound like pleasure or pain, but somewhere in-between.
“You okay?” I asked, halfway inside her.
“Keep going, baby,” she answered, “it just takes some time to get used to having a big dick up my asshole.”
“Okay,” I said, slowly continuing to fill up her ass, but not wanting to hurt her or bring her discomfort… even as I was in awe of how tight and warm her ass was.
Once all in, she said, “Now just sit there for a minute and let me get used to you in me.”
“Okay.”
After about thirty seconds, she surprised me as she slowly began moving her hips and started fucking herself.
“Oh, that is so hot,” I moaned, her asshole so much tighter than her pussy and the pleasure different.
“Your dick feels so good in my asshole,” she moaned, as she slowly rode my dick.
After about a minute of slow fucking I decided to bring it back to the role play and asked, “You like my dick in your ass after I fucked Velma’s pussy?”
“You fucked that slut?” Daphne/Mom questioned, looking back at me… back in character herself.
“You’re both my sluts,” I said, as I bucked my hips forward just as she moved back onto my dick, “is that clear?”
“Yes, Shaaaaaaaggy,” she moaned, as I grabbed her hips and held her with my dick buried in her ass. “But I’m your number one slut, right?”
“Yes, you’re my number one ass slut,” I corrected, as I began fucking her ass.
“Oh yes,” she moaned, “my asshole is always available, Shaggy.”
Then for a few minutes I fucked her ass. Slowly it became less tight and she begged me to fuck her harder. “Oh, baby, hammer my asshole.”
I slammed into her as her left hand went to her pussy and she began rubbing herself frantically. Forgetting we were role playing she begged, “Don’t stop fucking Mommy’s asshole, you’re going to make me come again.”
“Come, my sexy ass slut,” I ordered, as I reamed her asshole.
“Oh yes, don’t stop, baby, don’t stop, yes, right there, right there, yes, you nasty mother fuuuuuuuucker!” she screamed after a lot of moaning… the words made my nuts which had felt so drained just a little while ago, begin swelling with a fresh load of cum.
I kept pounding away throughout her third orgasm until she fell forward and said, “You may have broken me.”
“Sorry,” I said, smiling as I watched her in raw rapture.
“Do you want to come on Daphne’s face?”
“Yes,” I nodded.
“Go wash that dick of yours off and come back here,” she instructed.
“Be right back,” I said.
I went to the washroom, washed my dick with soap, and returned.
She was leaning on her side in a sexy pose when I returned.
“Come fuck my face,” she said, rolling into her stomach, her face at the edge of the bed and knees bent, putting her nylon-clad feet in the air.
“As you wish,” I said, as I walked up to the bed and slid my dick in her open mouth while admiring her sensuously shiny purple feet.
Then I face fucked her.
Slow at first.
Then faster.
Then, when I was close, I pumped my dick all the way in her mouth, my balls bouncing off her chin, until I grunted and yelled out, borrowing my role play partner’s tag line, “Scooby Dooby Doo!”
I pulled out at the very last second to plaster her pretty face with my cum.
Once all five ropes were unloaded, I slid back in her and had her suck me clean as I softened.
Finally, I pulled out, spun around and sat back on the edge of the mattress, gasping as I recovered from my third orgasm in under ninety minutes. Mom rolled onto her back, and like a contented kitty, languidly scooped the dollops of my man-cream off her face and into her mouth. Her movement had caused her red Daphne wig to fall to the floor and I saw her for her sexy, beautiful self – my once and forever mother.
I had just seconds to reflect on my beautiful mother and now my lover, when the voice of my grandmother, well, apparently she too wasn’t blood related, said, “I sure hope you have told him you are not his real mother.”
I turned my head to see my hot grandmother dressed in an Elvira costume with her arms on her hips.
THE END
