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 mak
e
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
