tagIncest/TabooFucking Mom: A Son's Virginity Lost

Fucking Mom: A Son's Virginity Lost

bysilkstockingslover©

Summary: Son learns his mother fantasizes about fucking him and....

Note 1: This is a Halloween 2017 Contest Story.

Note 2: Thanks to Tex Beethoven, thor_p, Robert, and Wayne for editing.

Fucking Mom: A Son's Virginity Lost

Dad left us two years ago to move to south Florida with a hot floozy half his age that he'd met in a bar. Mom was crushed, distraught and for almost a year felt worthless. Her path to recovery had gone through three stages:

Stage 1: Emotional breakdown

Stage 2: Anger

Stage 3: Happy Acceptance

I won't bore you with much about the first two stages as the first was pretty depressing and the second fiercely intense... but Mom got through them, with the help of my sister and me, and recently seemed to be reborn.

The happy changes started last summer.

She began working out every day.

She began to wear bikinis to go swimming in our pool instead of the one piece suits she'd always worn.

She got her first job... she'd been a stay at home mom her entire adult life. Dad was a stockbroker making more than enough for both of them to live on, and this remained true even when the family had grown twenty years ago to include my sister Cassie, and again eighteen years ago to include me, Michael. Dad had ruled the roost, and his picture of an acceptable household was the way it had been when he'd been a kid, which was 1950s Leave it To Beaver. In 1950s parlance, we were squares. The marriage was an unusual one as he was a quarter century older than my Mom, who'd been born in 1976. At forty-one she still looked great, and I loved to go out back and see her lounging next to the pool in a bikini.

Mom was now a secretary at a law firm, a job she'd gotten through her best friend Anna, who also worked there as a secretary.

Throughout it all, Cassie and I had both been there for Mom no matter what. During Stage 1 we both had constant wet shoulders from holding Mom while she wept and wept, and during Stage 2 we were constantly agreeing with her while she ranted on about what a royal bastard our father was, occasionally interjecting comments such as, "You're absolutely right Mom, and do you know what else?"

When Anna had moved in across the street from us about a year ago and she and Mom instantly became close friends, her friendship seemed to be the catalyst that began moving Mom solidly into Stage 3. Dad had never been easy to live with for any of us, and Mom had become genuinely cheerful and happy for the first time I could remember. Anna was easily one of the hottest women I'd ever met... ten years younger than mom but she lived across the street and they'd hit it off... partly because they both loved wine.

Anna had moved here from Hawaii, and you could tell that at a glance. She had dark Polynesian skin and a long mane of coal-black thick hair flowing down her back to her waist. Her face was gorgeous, slender and Caucasian in shape made exotic by her attractive dark skin. She was tall, about my and Mom's height of 5'10" and full-figured without being the least bit plump. She almost always wore loose, flowing floral dresses that on her I found far sexier than anything form-fitting or even low-cut would have been, particularly since it was obvious she never wore a bra to restrain her large soft breasts which were constantly moving and swaying freely beneath the shimmery material. Whenever she joined us for dinner, which was often, I had taken to wearing very tight underwear so I wouldn't appear to be a horny teenage boy, which of course I was.

By this time Cassie had moved a couple hours away to attend college on an Engineering scholarship, so it was always just the three of us at dinner. Our conversations were wide-ranging, thoughtful and often sexy. Both Mom and Anna always went out of their way to include me in these conversations and seek out my opinions just as much as each other's, never making me feel like a kid among adults. They also took wicked pleasure in scandalising me with crude, ribald jokes and poked fun at me whenever I blushed, but never unkindly.

A ritual that I cherished was that when she was about to leave after an evening of dinner and conversation Anna would take Mom and me, one at a time, into her arms, holding us firmly against her soft, sexy breasts and say something vanilla like, "Thank you for a lovely evening," and share a warm kiss with us. It wasn't a make out session with tongues or anything, but she gave each of us a long, warm, sensuous kiss with our bodies pressing together that I treasured (and made me glad I was wearing tight underwear).

Anna was wild, single and a partier. She wore a ubiquitous flower behind her right ear (instead of her left) a Hawaiian signal that she was single, available and approachable. Anna was the polar opposite of Mom... but somehow they meshed together... again likely the wine.

Mom's new job was a huge relief as it helped break Mom out of her humdrum routine of doing not much, and for me, it got her back into hosiery... something she'd quit wearing the day Dad left.

I can truthfully say I don't recall a single moment she wasn't in nylons my entire life until then. She was already dressed and in nylons when I came down for breakfast and she was still wearing them when I went to bed at night.

I knew she wore them for Dad and it was obviously his fetish... I saw him staring at her nylon-clad feet all the time... feet that were perfectly manicured at all times and never in heels (not at home anyway). And when she did go out, all her heels were open toed... only her winter boots ever hid her immaculate feet.

Of course after almost two decades of seeing her in nylons every day... it had become my fetish too. I stared at her feet constantly... often watching them as if they were their own television channel.

She also started wearing make-up... something she'd never done before at home... and only rarely and minimally when she went out.

Recently she had started going out at night, often with Anna, and every Saturday not getting home until after two am. And on Saturdays when she left she was always dressed up in some sort of unique and very sexy costume. In the eight weeks since she'd begun her Saturday nightlife she'd walked out the door in a strapless ballroom gown, a short, tight, low cut cocktail dress, a neck to ankles but so skin tight she could barely walk vampire outfit, a flapper dress with a bodice so loose I kept hoping for her to lean forward, an eighties outfit... on and on.

In short she'd had a total rebirth from her doldrums and was not only a brand new chipper self but seemed to be a completely new woman.

I was happy as she was back to wearing nylons every day and back to being the buoyant woman I loved as a mother (when Dad wasn't home and giving us all a hard time).

I couldn't help but be curious about her Saturday night rendezvous.

So I decided to hack into her phone and add a tracker app, one Saturday two-thirds through October.

She was dressed in a 1950s housewife outfit that was innocent and yet somehow sexy as hell... maybe it was the nylons... but fuck was I hard.

She was picked up by a taxi, something I hadn't noticed before, and I waited a couple of minutes, jumped in my car and followed her phone.

Twenty minutes later I was parked across the street from a large home in the middle of one of the more upper class neighbourhoods in the city, the app telling me that Mom, or at least her phone, was inside.

The house wasn't a mansion by any means, but it was a large house.

There were surprisingly no cars parked in the driveway or even on the street except mine, even though the sounds of many voices were drifting across the street.

Was Mom here by herself?

Did she have a boyfriend?

Suddenly a taxi pulled up in front of the house and a woman dressed like Marilyn Monroe got out.

I remained in my car and watched for the next twenty minutes as taxi after taxi pulled up.

Women dressed in various sexy 1950s attire.

Men dressed almost exclusively as James Dean wannabes.

A couple of couples that came in matching attire.

I also saw Anna leave a taxi dressed as a dark-skinned long-haired Betty Boop, the first time I'd ever seen her without a Hawaiian dress, but still wearing her I'm available flower behind her right ear. I think Betty Boop was more 1930s but who cares... Anna looked absolutely amazing.

The entire time I was trying to figure out what the party was.

Halloween was just over a week away, but Mom had been dressing up every Saturday.

I wanted to sneak up to the windows and peek in, but besides being creepy, it would be impossible to defend if I were caught.

Intensely curious though, I decided to drive back home and snoop through Mom's bedroom and computer in hopes of figuring out what was going on.

I know it was an invasion of privacy but I was beginning not only to get curious, but also concerned by her behaviour. Was she okay?

I sped home and went directly to Mom's room, kind of feeling like a private dick looking for evidence.

I searched her dresser drawers where besides discovering all her panties were thongs (except one), I found a whole bunch of still unopened packages of thigh high stockings in a few colours and from a brand I'd never heard of called Wolfords (an English company). I would later learn that the pantyhose were called tights and the thigh high stockings were called stay ups. The average pair was a whopping 50 bucks!

I picked up an already opened pair and felt them... these weren't anything like the cheap nylons my last girlfriend Jodie had worn for me... no, these were sheer silk that felt like heaven.

God, I wanted to feel these on Mom's legs.

I replaced the nylons exactly as I'd found them and kept searching.

The rest of her dresser drawers were uneventful except for a couple of sexy nighties.

The closet revealed nothing, other than some new clothing which definitely had a more modern look... including shorter skirts, skirts with generous side slits and dresses that seemed too small for her... both in length and breadth. I also found a Batgirl costume hanging in there... was that what she'd be wearing for Halloween? It looked like something my slutty high school peers would wear when their parents weren't around.

Of course my cock hardened at the image of Mom wearing this ultra-skimpy outfit.

Not to mention that Batman was by far my favourite superhero and Batgirl a fail-proof bone stiffener... especially Yvonne Craig from the corny Adam West 60s version, although Alicia Silverstone in that tight outfit was pretty damn hot too.

That said, this outfit was not even a third the size, nor would it cover much of my mother's body other than her breasts and pussy... her ass would definitely be on full showcase if she bent over at all.

Fuck, was I horny. I considered going to my laptop and watching one of my favourite scenes... my newest stroke fantasy the scene called Mom's Panty Bandit where the MILF Ava Addams who somewhat resembled my mom, was in amazing mocha thigh highs. Each time I watched it I imagined Mom taking off my burglar's mask and fucking me.

But I resisted as I went to Mom's laptop and entered her password which was my birthdate (which I knew from when I'd had to add some programs to her computer a couple of months ago).

I logged in and saw her e-mail was up. I didn't expect to find anything there, but wow did I ever.

The most recent email was still up and open;

The subject line was: Password for 1950s Not-so-Innocent Party

Monroe

That was it.

I kept that e-mail open as I went to look for more e-mails from the sender, MasterT.

There were three:

1. Password for Diva Divine

Flapper

2. Password for Cum Vampires

Blood



3. October Dates

Oct 7: Diva Divine... dress in your 1920s best....

Oct 14: Cum Vampires... everyone craves cum....

Oct 21: 1950s Not-so-Innocent Party... what really happened behind the doors of the white picket fences.

Oct 28: Halloween Party



Due to a onetime gate crasher, the password will be emailed two hours before each party.



As I read these, my hard cock flinched. As I had kind of thought, these were sex parties. Which of course meant that my mom was attending sex parties.

Did Mom go to these parties and fuck strangers?

Did Mom have lesbian sex? With Anna?

Did Mom participate in orgies?

Wow! Wow! Wow!

Now even more curious than before, I decided to search Mom's browser history.

To my astonishment:

a) She didn't bother to erase her browser history

b) She'd visited a few porn sites. The majority were reading ones, although after skimming through some she'd saved, I found a few titles she'd read that gave me sudden hope for a fantasy I'd never expected to be more than just a stroke fantasy: Anal Gangbang, Becoming my Daughter's Pet, and Taking My Son's Virginity... the last title really making my cock flinch, although the vision of Mom naked with my older sister Cassie was hard not to suddenly visualize.

Did Mom fantasize about having a lesbian encounter with Cassie?

Was there any possibility she wanted to actually take my virginity? If so, bring it on!

I'd gotten head from my last girlfriend Josie, and a couple of hand jobs, and I'd licked a couple of pussies too, but I had yet to have actual intercourse. To do it with my hot Mom would be a dream come true!

I searched her saved files and gasped. She'd downloaded a few videos, all with incestuous themes including My Dominant Daughter, 69 your Mommy Time, My Son's Big Cock, Backdoor Mommy and Cum 4 Mommy, just to name a few.

I clicked on the My Son's Big Cock video and watched.


A mother walked in on her son masturbating (although the actor looked a lot older than the eighteen he was supposed to be). She acted surprised as she stared at her son's large cock. The son with his eyes closed, unaware his mom was watching, kept stroking as he moaned, "That's it, Mom, suck my cock." The Mom's eyes went wide, and after a tentative pause, she removed her shoes and silently walked over to her son, climbed onto the bed and took her son's cock in her mouth. He opened his eyes, they kissed, and the obvious ensued.

That was all it took for me to shoot my load in my pants, imagining Mom doing the same thing to me.

As I tidied up, making sure I left the computer exactly how I'd found it, I tried to process Mom having incest stories and videos on her laptop. Was there a chance she was fantasizing about fucking me?

That question spun in my head all week as I stared at my mother who woke me up every morning. I mentally asked What if she wants me?

As I stared at her at the kitchen table.

As I listened to her tell me about her day.

As I glanced at her stocking-clad feet.

As I jerked off imagining my own real life mom and son video.

During the week leading to Halloween I formulated a plan... a risky plan... an unlikely to work plan... a Mission Impossible plan that seemed utterly ridiculous yet always worked plan.

I bought a Batman outfit, spending a big chunk of the money I'd got for my 18th birthday.

I checked her e-mails every day for the password.

I checked her browsing history to learn she had just favorited a story called Pet Mommy. I went to my room and looked it up on my own computer and read it. I stroked my hard cock throughout the story absorbing the idea that Mom got off reading about being treated like a slut by her son.

I chatted with her as much as I could to see if I could draw out anything abnormal... yet she still seemed like my same sweet, innocent, albeit loving mother who would be there for me no matter what.

I stared at her nylon clad feet every chance I got.

Then Saturday came.

Still no password.

I resisted jerking off all day and when Mom walked into the living room in her Batgirl outfit complete with cape and black thigh high stockings I joked, "Mom, you look like any one of the girls in my high school today."

"You think so?" she asked, looking a little uncomfortable even as she seemed also to be posing for me.

"Definitely, if I saw you like this at a high school party I'd be all over you," I continued, hinting at what I hoped was a foreshadowing for later tonight.

"You're so sweet," she said, wiggling her toes as if aware of the impact she had on me with her perfectly manicured feet and sheer nylons.

"And you're so hot," I added, not hiding the fact I was checking her out.

"Michael," she gasped, her face going red at my aggressive compliment.

"I'm serious, if you weren't my mother..." I began and stopped on purpose, wanting to see her reaction.

"Then what?" she asked playing dumb, although I could see through her... my playful sexual banter had her intrigued.

"Nothing," I said, wanting to draw her in.

"You can't say something like that and finish with nothing," she protested, even as she wiggled her toes around as if knowing my fetish.

Did she know my fetish?

"Mom, you're a MILF," I stated.

"What is that?" my Mom asked, appearing still rather innocent and stuck in the past, but I wasn't sure.

"A mother I'd like to..." I began.

"A mother you'd like to what?" she asked, either oblivious or just wanting to hear me say it. If she was reading intergenerational porn stories, it was likely she'd be familiar with the term.

"Fuck," I finished, enjoying the conversation.

"Oh!" she said, as clarity (or perhaps satisfaction) hit her. If I didn't already know what I knew, I imagine I wouldn't have put any stock into her facial expression. But since I did, I noticed her processing the words and maybe realizing that her naughty fantasy wasn't as impossible as it may have seemed. Just like I'd taken a while to process her aspirations when I found her incest secrets on her computer.

I continued on the offensive, "Plus, those thigh highs are really sexy."

"Your father liked them," she said.

"I guess that's why I have the same fetish," I revealed, wanting her to know I did, and continuing to open Pandora's Box a little wider.

"I thought you might," she said, wiggling her toes again and giving me a wink.

"I made Josie wear them every time we went out," I continued. "I love the feel of them... from the outside in of course."

"Too much information," she smiled, although I could tell she was enjoying the knowledge. She looked out the window to see that the taxi had arrived.

"I've got to go," she said, slipping on her heels.

"Have fun," I said.

"Thanks."

She then surprised me by coming and giving me a hug with her tits squeezed against me. "I love you, son."

My hard cock purposely flinched against her body... I didn't try to camouflage it... one more hint of the impact she had on me... one more hint of the interest I had in fucking her.

"I love you too, Mom," I replied, as she kissed me on the mouth very much like Anna often did, no tongues but loving and sensuous, her perfume lingering even as she walked away.

I watched her leave, I went to the window and watched her get into the taxi, then dashed up to her room and laptop.

So naïve, never ever thinking I would violate her privacy, her e-mail was open as was the message with the password.

I smirked as I read the password: Fuck or Treat.

Oh I planned to get a treat... and a fuck... and give away my virginity.

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