(Writer's note: The below story is a work of fiction, but the characters and back story are real. This story
introduces Jennie. She was my first love, my muse, and now the spirit of my 2021 WINTER HOLIDAY
STORY. Jennie and I fell in love at a young age, but lost each other in the 1980's. I am convinced it would
have been one hell of a ride if we could have somehow re-discovered each other before the baggage of life
had settled upon us. The following is just one vision of the possibilities... Happy Holidays and enjoy the
story. I know I enjoyed writing it!! Also, this is my entry into the WINTER HOLIDAY 2021 contest --
Please vote)
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"Wow, what a fucked-up year that was", I mumbled to myself. Calendar year 2020, PLEASE go the fuck away and never return! That was my thought as I jumped into bed on the last night of December 2020. Certainly, the biggest story of the year was the Covid-19 Pandemic, and the resulting tragedies of death, sickness, and social strangulation. No restaurants, no bars, no ballgames, and no gatherings of more than ten persons, etc., etc. Thus, my New Year's Eve celebration options were relegated to zoom calls (fuck that) or a lonely night in bed. (my choice). The goal of the game was now survival until the vaccine could be distributed, and hopefully a return to life as we knew it.
As I settled into bed, I did a little mental review of the year that had just passed, and was truly astounded at
the actual depth of how terrible the year 2020 was. As stated, the pandemic was the lead story; millions infected by the virus, and by year end over 320,000 Americans were dead because of it. But the residual carnage may have been worse than the disease. Violent political confrontations, decimated industries, personal financial ruin, evictions, homelessness, loneliness, and incalculable mental and emotional stress. A terrible ordeal for so many!
But sadly, the Covid shit was just the tip of the 2020 iceberg. While enduring the pandemic, we also fought
through the horrendous effects of climate change such as wildfires, hurricanes, and tornadoes. Fuck; it
seemed to me that the entire State of Louisiana was either blowing away, or under water for most of the year.
And forget about California and Australia; they both seemed to have burned to the ground this year.
Then add in the accelerant of the Trump administration and the entire side-show that that entailed, and it
seemed as if everything in the world was either sick, dying, fighting for its life, on fire, or under water.
Calendar year 2020 also included the stories of Jeffrey Epstein, Black Lives Matter, Me Too, The
Presidential Election, Stop the Steal, Kobe's helicopter, the loss of the inimitable RBG, and not insignificant,
my fucking Philadelphia Eagles losing in embarrassing fashion to the stinking Cowboys with the division
championship in clear view. FUCK, the whole year was a disaster.
But as I settled into bed on this special night, I tried to clear my head of all that noise. I was going to wake
up in 2021 with an unblemished future ahead of me. Covid going away, politics changing, climate change
out, vaccine in, la de da... It was all going to work out. So, as I fired up my kindle, I transitioned my thoughts from Covid and politics to my reading options before the New Year's nap. Newspaper, book, or
porn were my standard go-to options. Not surprising, I selected the porn category. But, instead of my usual
preference for videos featuring thin blondes in high heels getting fucked by dudes with insanely large dicks, I
chose to read erotic stories on Literotica.com.
Literotica is a great website. A free, and easy-to-use forum, whereby writers of erotic stories can publish
their tales on-line to a virtually limitless audience. Literotica will publish virtually any story, featuring near
any kink or desire, with only a few of the most devious perversions outlawed. The stories can be searched
by date, writer, fetish, or genre, and no matter what makes your dick hard, or your pussy wet, there is
someone writing a story about just such a thing. I truly love the Literotica website. Tonight, I found
myself browsing newly submitted stories under the general heading of "mature". The new offerings were
many, but included stories about old women lesbians, teachers fucking students, a dude fucking his friends
grand-mom, and a fascinating story about a maintenance worker at a 55 and over development who was
fucking the entire female population of the community one broken appliance at a time. But, what I finally
settled on, was a story about old high school lovers re-acquainting at their 25th annual class reunion.
The story itself was cliché but certainly relatable. An ex-high school jock meets his old cheer squad
girlfriend at their 25
th
high school reunion. Both still look good, married with kids and lives, but having
an itch for each other that somehow never managed to get scratched. They spent the evening flirting,
dancing, and remembering the way they used to feel. When the lights came on, and they contemplate
final goodbyes, they realize that both are checked in at the upstairs hotel. What followed was a well written
night of glorious love, sex, and passion that left me with a hard-on and nothing to do but stroke it...
As I began to play with my dick on this final night of the worst year I could remember, I thought of my old
high school girlfriend Jennie. Jennie was the most beautiful girl I have ever seen. Back in our high school
days (I was class of '75 -- Jennie was '76) She was about 5'6" tall, weighed about 110 lbs., straight blonde
hair down to the middle of her back, beautiful B (maybe C) cup tits, long legs, and the sweetest disposition
of anyone I have ever met before or since. Envisioning her sensitive small titties with her inverted nipples,
and her fragrant pussy, demurely hidden by a thin coat of blonde hair, took my penis into full raging hard-on mode.
In high school, I While in high school, I truly was the football and baseball playing jock and Jennie really was the teen-angel cheering me on. Both of us were very inexperienced sexually, but over the years as our relationship developed, we pretty much learned about sex from each other. Memories of us being locked inside my bedroom, with a large tub of Vaseline and just exploring all the possibilities came flooding back to me. The vision of Jennie in her cork sole platform sandals, denim hot pants, and braless halter top; or Jennie dressed to the nines in her low cut, yellow prom gown and matching yellow heels, made me tighten the grip on my cock and stroke it a little faster. And the memories of beautiful Jennie with my dick in her mouth, or with my cock squirt covering her hand, face, or titties took me near the edge tonight. But what took me over the top, was the vision of Jennie cumming. I remembered how I would slowly finger-fuck her wet cunt with my thumb, while at the same time gently sliding my index and fuck-fingers into her ass. Slowly and gently fucking both of her holes while trying to match the rhythm playing in her head; increasing the pace of my fucking to match the increasing tempo of her thrusting hips, each thrust quicker than the last, until the music reached its climax and she exploded in orgasm. As I watched this scene play out in full virtual reality in my mind, my own body went rigid, and my dick exploded in orgasm with sperm blasting all over my belly and hand. Oh, Jennie what could have been, was my last thought before drifting off to sleep?
Cue the dream sequence music... Fuck, I'm running late! Tonight, was Jennie's wedding shower, and I
promised I would pick her up at the hall at 9pm to help get her, her mom, and the gifts home. And due to an
extra-innings softball game, requisite beers, and then a shower, I didn't arrive till near 10pm. Thankfully,
both Jennie and her mom are the forgiving sort, and I found them sitting happily at the bar, getting smashed,
and sharing all the gossip they learned from the girls throughout the evening.
Jennie and her mom are both beautiful women, albeit at different stages of life. As described above, Jennie
is a classic beauty in the springtime of life. Tonight, she was wearing a little black dress, sleeveless, with
high collar, open back, and mid-thigh in length. She left her legs bare, and paired them with matching
strappy, black, 4" heels on her feet, and absolutely no underwear below (Jennie loves the commando feel).
A great look for her! And oddly, I noticed her mother was looking rather delicious tonight as well. Ina was
a classic Italian beauty, albeit in the late summer of her life. She was not heavy, but curvaceous for sure,
with a lush, full head of auburn hair that she uniquely parted on one side, and casually flipped over to the
other, so that it all fell down the one side of her face in a very sexy kind of way. Full breasts, full ass, and a
full personality put her high-up on the pedestal of great mother-in-laws to-be. Tonight, she wore a flowered,
off-white, chiffon top that was slightly see-through, a wide, red belt which helped accentuate her heavy tits,
an off-white, (without the flowers) narrow skirt, with a hem line just above the knee and a 6" teaser-slit. She
also went bare legged but wore a sexy pair of red heels to match her belt and red flowers. I didn't know
the status of Mom's underwear but was hoping that going without might be a family tradition.
I sat down and shared a drink with the ladies and truly enjoyed their happy banter about the shower, and
gossip about the other ladies in attendance. Thankfully, it appeared that Jennie, Mom, and the whole lot of
woman all had a fun evening. Jennie was effusive about the generosity of her family and friends in the gift
offerings, and assured me, there was nothing left for the house that we needed to buy. As I sat listening to
Jennie and her mom chatting, my dirty mind drifted to how radiant and happy Jennie looked tonight. A
happy, slightly drunk, and elegantly dressed woman might be the sexiest thing I can imagine. Tonight,
Jennie was clearly happy, certainly drunk, and very nicely dressed. Oh, the possibilities! "OK ladies, why
don't you both finish your drinks, then do whatever bathroom things you might need to do, while I load up
the truck. Then we'll meet at the front door and head home", I suggested as both nodded in compliance.
As we drove, it occurred to me that all of us were at some point on the drunk spectrum, and that I would have
to drive ten miles past our house to take Mom home. Thus, it was agreed that Mom was going to have a
sleep over tonight, and I would take her home in the morning. Upon arrival at our house, the plan was for
Mom to sleep in the spare bedroom, and Jennie and I to sleep in our usual spot on the king size bed in the
master bedroom. That seemed simple and clear enough. Well, I don't know what happened while I was
unloading the truck and walking the dog, but when I finally got up to the bedroom, Mom was partially
