The following story was supposed to be my entry into the 2023 Halloween Contest. But timing is everything sometimes, and I missed the entry deadline. But I like the story, so it is being submitted anyway. I truly hope you enjoy it as well!! It was originally written for the Toys and Masturbation category, but it ended more as a mature story, and thus it has been submitted in that category. Full disclaimer - it also includes a few quirky fetishes and includes an interesting visit with a trans-woman. Also, all characters in this story are fictional and over the age of 18. No exceptions. Please enjoy the story, and this spooky season!!
Halloween is a weird holiday. I've always thought that. I find it amazing the extent that mature adults will go to celebrate their macabre fantasies. I do think Halloween is a special treat for children, however. Dressing up in pretend costumes, bonding with neighbors, and friends, for trick or treating, or fun parties. Then sharing the sugar-bounty with family for subsequent weeks on end, until alas, the bowl of candy is empty; usually just in time to restock with fresh Christmas treats.
But, despite my opinions, Halloween thrives! It seems to me, folks in the USA now decorate with ghosts, goblins, orange lights, faux spider webs, witches, and other things scary, almost as much as they do for Christmas. I don't get it, but Halloween is a big deal. But my opinion on the significance of Halloween is unimportant. As long as it's enjoyable, my wish is that everyone celebrates whatever holiday they want, however they want.
What I would like to share with this story, is a very pleasant memory of a Halloween of long ago. An amazing night that I've relived in fantasy many times over. A night of shared pleasure, with a few surprised, and grateful friends, that helped me understand the challenging conditions of aging, loneliness, and fleeting happiness.
As I write this story, I am sitting naked in my little apartment, in the quasi-assisted living facility for senior adults, that I now call home. The residents here are seniors, generally in our 70's, 80's, and most still healthy enough to get around with limited support. Mostly, I like it here. The staff is generally pleasant, the neighbors mostly kind and sharing, and the facility is just right for aging adults, who do not want to become a burden to their children.
Thankfully, at this point I'm healthier than most, and still get around as I need to keep myself entertained and stocked. Now being in my eighth decade, I've learned a few things, and am quite happy to be at this point in my life. Age, and experience, come with wisdom. So, as long as I'm healthy (a big qualifier I know) I am quite content with my senior status in life. In the great circle of life, I know my circle is approaching full closure, but I'm good with that. A beginning and end to everything, and all that.
Sorry for drifting. Let me get back on point. I am sitting here at my little desk, naked as stated, and writing out my memories of a special Halloween from long ago. As I write, I occasionally stop to diddle myself, which, while certainly pleasurable, also helps me remember pleasurable things to write. One of the things I've learned about aging is that one never gets too old to diddle yourself. So, masturbation helps me write, and writing helps me masturbate. Is that perfect or what?
Anyway, this tale begins with a 21- year-old me (Ellie), working part-time, weekend night shifts, at a senior citizens assisted living facility, similar to the one I live in now. I was struggling my way through college, without much money, guidance, or purpose, hoping to stumble upon something better in life. The job paid OK, for a part-time gig, but night-shift weekends was not the most attractive shift for a young lady to work. But the responsibility was minimal, the place was local, and the residents were generally appreciative and welcoming.
I was there to respond to any overnight emergency, which meant calling for immediate medical support, or janitorial cleanup. Clean-up being the much more frequent need. Secondarily, I was expected to make twice nightly rounds of the resident areas, ensuring that nothing out of the ordinary was occurring. Over time, I came to know many of the residents, especially those who stayed up late. Virtually all were glad to stop and talk, share info about their families, or facility gossip, or politics, and I came to truly enjoy the banter with many of them.
Interestingly, the first round of the night tended more towards social chatter and gossip. The 3am tour more frequently included chit-chat about personal problems, death, and most interesting, about sex and the senior citizen. Let me state firmly that while the physical sex drive of senior citizens may be in decline, the mental sex drive is at full throttle. Senior citizens love sex as much as teenagers. Believe it!
As I did my rounds, I learned where to look to find action. Of those awake at 3am, pornographic magazines were the preferred reading, (the 1980's pre-dated laptops, phones and other devices) and Masturbation was rampant. It seemed to me that on any given night, half the residents were performing self-service activities. Mutual masturbation with a friend, or group of friends was also prevalent, and seemed the optimal way to spend an evening at the senior center. Man and woman watching each other rub one out was probably the standard combination, but there was no shortage of man watching man, or woman watching woman, while masturbating. On rare occasions I'd catch a view of oral sex, straight or gay didn't seem to matter, and on very rare occasions I'd see actual fucking. But mostly it was masturbation, in one form or another, that kept the residents occupied late at night.
Initially, my participation in any of the activities was nil. Mostly I tried to support the fun by commandeering the necessary lubricant, or clean towels, or helping residents get from room to room, or perform a subtle clean-up of any mess before morning. But being a horny little slut, as my familiarity and comfort level grew, so too did my desire to get a little closer to the action. I liked to watch the oldsters going at it and I was not averse to diddling myself while I watched when the opportunity presented itself.
As time went by, I became a little more daring. Sometimes I would go without panties to facilitate quick access to my sex. Or I might wear a butt plug up my ass to tease myself throughout the night. Occasionally, to up the ante, I wore luxurious lingerie, with expensive nylons. All done to please myself, and not for public consumption. Until...
On the evening that I unexpectedly participated in my first act of mutual masturbation at the senior facility, I was really horny. I stood in the entry alcove of a resident's unit, watching as two ladies masturbated themselves, and each other. They were dressed in sheer night gowns and high heels. One leaned against the headboard of her bed, the other sat opposite her on the lazy-boy type side chair. They rubbed their own pussies with vigor, rubbed each other's pussy with the same intensity, all while dirty talking, using all of the hard "C" words like fuck, and cunt, cock. Each eventually bent over, to tongue love the other's cunt as well. I watched, while rubbing myself, as each took the other to a powerful orgasm. As I was just about to climax myself, I heard a grunt and groan from over my shoulder and watched as a male resident standing not 10- feet behind me, shot multiple ropes of cum from his penis. For some reason, everyone was suddenly looking at me. "Oh fuck, I'm busted," I mumbled out loud.
After a few very uncomfortable moments, all four of us in the room laughed it off as a natural response to watching good sex. As the ladies pleasured each other, I was wanking myself while watching them, while at the same time, Kevin was jerking off, while watching me jerk off, as I watched the ladies jerk off. We all realized that not only was it a highly erotic situation, but it was also fucking-funny as well. Each of the seniors also commented about how nice it was to see a naked body that was still young and fresh. After, laughs all around, then a little reorganizing, the ladies invited me and Kevin in, to do it all over again. And we did. It was a wonderful group-grope, each of us cumming while watching the others, with no one in the facility being the wiser. Nice!
As time went by, and word got around that Ellie enjoyed watching, and being watched, I became a starring member of the 3am masturbator's club. Everyone wanted to catch Ellie masturbating. They'd actually set traps for me to catch them, so they could catch me. A fun and sexy game, that everyone in the club enjoyed.
There was a lot of late-night masturbation going on, but only about 12- regular 'Club Members' who liked to share the late-night masturbation experience. Generally, everything was unscheduled and unpredictable, featuring someone different, doing something different, either alone, or with someone else. I loved to watch, and I enjoyed flashing my underwear, tits, or pussy to the old folks. But to maintain some level of professionalism, I kept my own hands on my own body. Close enough to see, and be seen, and add something exciting to the experience, but always hands-off others (but for that one time). Enjoyable, but not too intrusive... Until Halloween 1989.
Most hospitals, Senior centers, or other medical type facilities encourage the staff to dress-up, decorate, and generally participate with the clients to celebrate the various holidays. Halloween was no exception. The doctors generally did not participate, but most of the nursing, attendant, and maintenance staff did participate with decorating, sharing holiday treats, and playing dress-up. Halloween was certainly the most popular dress-up event, with most of the staff wearing a costume in one form or another. And on Halloween 1989, yours truly was the star of the night.
Many of you young readers may not remember, but back in the 1980's and 90's, there was a late-night television personality named "Elvira, Mistress of the Dark". Her real name was Cassandra Peterson, but no one knew her as Cassandra. She was a former go-go dancer, and showgirl, who found true fame as "Elvira", a cult-level, late night host of a television show featuring B- grade horror films, served with a healthy dose of both comedy, and eroticism.
Her base schtick was accompanied by her fabulously sexy outfit and sexuality. Porcelain, white skin, long, deep black hair, down to her ass, but puffed up on top of her head. Luxurious black satin, evening gown, long slit up to the hip on the right side, very low-cut front, showing a huge portion of her inflated tits. Black nylons on her legs, with tall, black, patent leather heels completing her look. Unique, sexy, witty, funny, horrific, and something completely different for her late-night audience. For Halloween in 1989, your favorite writer dressed as Elvira, Mistress of the Dark, to tease and stimulate her late-night friends at the senior center. What could go wrong, right?
Now, a little about me, if I may. I would consider myself cute, but average in most every way. Average height (5'-4"), weight (120 lbs.), hair (down to mid-back, dirty brown), breasts (B- cup), eyes (gray) skin (average white with a few freckles). I think I am nice to look at, but no one has ever accused me of being beautiful. But on Halloween in 1989, when I dressed up as Elvira, I was fucking-beautiful!!
The getting ready to be Elvira was as much fun as playing the role of Elvira. To start, about a week before Halloween, I went shopping and spent way more money than a girl who works night shift at a senior center ought to, on a Halloween costume. Beauty does not come cheap! I bought the required hosiery and lingerie at Victoria's Secret. Very nice! I will not divulge how much I spent, but more than a weekly paycheck. Thankfully, I found a perfect replica dress, and black platform heels, at a second-hand store.
Friday afternoon, after my daily activities were all complete, I dyed my own hair jet-black. No wig for me, I was going full Elvira. I did buy a bouffant hair bump for the top of my head, just to assure that I conquered the look. But all told, my hair looked great when combined with the bouffant.
