Grabbing the Brass Ring

It was probably a terrible thing to do, but I was much younger then, which is the only reason that I would commit this sordid act to paper. Most of the characters in this story are no longer with us and I think the others might just marvel at how it all came to be or thinking "Why didn't I think of that?" I'm about to describe a scheme that allowed me to take advantage of a family member in the worst imaginable manner and purely to satisfy my own craven lust.

I wanted to fuck her and this would be the best possibility. We were always close but certainly not in that sexual way. Recently, we'd been spending more time together and sharing little intimacies, and I was sure that I was gaining her trust. That would make it so much easier to seduce her and finally to have sex with her.

My name is Martin. At the time I was 22 years-old and unremarkable in most ways. Standing 6'1" and a chunky 190 pounds, I had light brown hair and brown eyes. Essentially, I would blend into any crowd and in a lineup, I would be the guy that everyone had seen, all over the place. But my grandmother Evelyn was dramatically different. She was brought-up in a different age and had a Patrician "air" about her. She was raised and educated around "old money," however most of that cash was squandered long before she reached adulthood. We have an established family name that is posted on buildings and avenues, that's why I won't mention it.

This was a different age, far removed from today's hectic pace. An era of "Free-love" and first sending men into space. Before the concept of cellphones and when you needed to get off your ass to change the channel on the TV. And when terrible assassinations practically bookended the decade and shattered our blissful lives. There was a style and class to this chapter of America that ended with tie-dyed shirts and bell bottom pants. Wealth was still aspired to but became much less ostentatious. The family-first mentality was transitioning to a me-first ethos. Stars were no longer exotic or "bombshell-types" and younger women wanted the androgynous, a-sexual, amorphous look of Twiggy and others. Glamour was staging its last stand.

Evie learned proper etiquette and style while it still mattered, but she was not snooty enough to let it deter her from having fun. As an older woman in her mid-60s she continued to dress and entertain with a certain flamboyance, taking parts of her staid past and always injecting the most modern touches, just to stimulate or antagonize her peers and the younger folks in the family. She wore her platinum-blonde hair in a full display of weaves, bobs or cascading down her back, to fit whatever mood that she was in. Her accessories were as likely to be "mood rings" and bangles dangling from her ears, as the pearls at her throat or diamonds from her many past suiters.

She had what was called a statuesque figure. In her bare feet, which occurred whenever she kicked her heels to the side, signaling to everyone that "Grandma was ready to relax," she stood about 5'10" -tall for the time- and her 130-pound frame was dominated by her 36-inch bust and long, shapely legs. Both of which were often captured in period photos from the beach or in "High-Society." She had a sassy combination of a runway model's elegance with the boldness of Mae West.

Those tits of hers, caught my eye early because women her age didn't wear low-cut tops or prance around the house braless with impressionable people sneaking sideways glances and using those illicit visions for masturbation material. She had the classic 36-23-36 measurements that shifted slightly with the years, but when draped and dressed correctly, was still the ideal for young men of any age. For her fiftieth birthday, she got a tattoo of the "lips and tongue" icon, made famous by a rock band, just above her left breast. When I could see that symbol clearly, I knew that Grandma was wearing an outfit that the rest of the family might view as obscene. I liked it!

I was not the only grandchild, and family photos often featured a herd of kids surrounding her. But I was the one who, starting from a young age, ran errands for her and sat to hear her stories and asked about the trinkets and the fashions of the past ages, so naturally became her favorite. She knew fantastic people and was a member of the jet-set class. She could regale me with insider stories of the rise and fall of so many "Big-Name characters." I enjoyed spending time with her and she was teaching more than I could ever get in school.

Growing up, she lived in a gaudy suite on Fifth Avenue and I was always anxious to help her with little chores just to see the rich trappings, but before I could drive, she had downsized to a far-less swanky apartment near our suburban neighborhood with fewer gilded touches but much easier maintenance for a single senior citizen. Still, I would always be there if furniture needed moved or leaves raked, and she entertained me with stories about galas or upper-crust weddings that she remembered from her childhood and would occasionally fill me with bawdy stories of "Speakeasies" and clandestine affairs featuring film stars and moguls.

In my eighteenth year she also introduced me to Martinis and Marijuana while watching "16mm blue movies" and looking at naughty postcards from the age. There was never any concern about corruption because I was a serious student with few bad habits but to Evie's view, "A little decadence is good for the soul." Later visits brought Jell-o Shots and "Deepthroat." As the drinks flowed and the laughter increased, she would often joke that "You're too young and I'm too old, to be doing this but 'boy' if we ever got together, hold-on to your socks!"

Evie emphasized that only bold people advanced in rough times. Scared or timid people were like attendants at filling stations, watching the cars go by. And when opportunity presented itself, the clock began ticking. take a chance or get trampled. One of her favorite sayings was, "You don't get poor by taking." But she often cautioned me about knowing the difference between boldness and rashness. "Use the talents that you have but be ready to justify your actions," She always advised.

She spoke with unerring majesty in elegant settings but when informal gatherings or just with me, she could sling swear words with the gusto of a stevedore. If drinking or laughing and her guard was down, she had a raspy, throaty timbre to her voice that allowed me to envision whore-house madams that she used to tell me about. With a twinkle in her electric-blue orbs, she could slice someone to ribbons without them catching the sarcasm in her voice. And she had a habit of leaning into me to whisper naughty details, while pressing her bodacious bosom into me and gripping my thigh with the painted nails of her searching digits.

Her tales of "The Roaring Twenties," or of "The Great Depression" and the pre- and post-war years filled me with a certain nostalgia and of having missed-out in times that really set this country on its upward trajectory. Unlike any grandmother I have ever seen or heard of, Evie would drop a remark about some low-level lounge singer from the 40's and then mention with a winsome charm that he was "Hung like a bull." "Honey," she stage-whispered as if I weren't the only person in the room, "They were always attracted to these," and she would shake her prodigious front porch," watching my naive eyes pinball back and forth, "but they had to get past this," and she would point to her head. She always taught me something that the history books left out and there was always a moral lesson to be learned. She made things exciting but she never sugar-coated the bad points. "I spread my legs for a few of them, just for the fun of it," she cackled in her trademarked husky laugh, "But most of them, once it got down to it, were just scared little boys playing at a game beyond their talents." Then she would finger the jewelry that adorned her ears, neck or fingers. And announce her primary warning. "The losers always had to pay the price."

It was about that time, that I started noticing her figure and understanding in a crude and incestuous fashion, that she was much more than just my grandmother living with memories of the past, there was still a wild woman with a nice body aching to revisit her youth. A youth that was constrained with the puritan morality of the age but with whispered indiscretions that hinted at a "Flapper-Age" mentality encroaching on a "Bobby-Soxer" era. I was graduating college by the time most of this story took place. There was a gleam in her cool blue eyes when she felt that she was letting me in on timeless secrets or in exercising her former ability to dominate someone with a word or a look. I remember when she instructed me to meet a certain VP of a bank for an interview, she recommended that I mention her name, and she then intoned, "If that doesn't open doors, ask him to call me and I can share some stories about his old man."

There would be evenings when I would drive her to a reception and I could imagine her looking regal in the chauffer-driven sedans she often mentioned, she would look sharp and sexy in a sequined sheath, slit up one side and her bounteous decolletage dripping with jewels. She would toss her blonde hair and flash that killer smile. The fiery gemstones sparkled from her wrists and neck. Then an almost bare leg would appear from the car and her wrap would slide down her shoulder, revealing a hint of that generous bustline that triggered so many lusty thoughts. Every gentleman and wanna-be diplomat would rush to offer an arm or clear the path. She always turned heads and caught every eye. This was a sixty year-old woman that the shallow ingenues could only hope to become. I could just imagine her in her youth. She maintained the same brassy attitude but was no longer confined by convention. She once told me that when she was young she had "fuck you money," those were the days she said, when her name alone, "got her in." She didn't regret that those days ended, only that she got old.

And at her home on hot days, we would sit on the balcony, me in cut-off jeans and a tank-top, trying desperately to hide the bulging erection that had become a near-constant companion to our private get-togethers. Her in slinky hip-hugging shorts and the sheerest of blouses, often with her nipples poking through as we drank spiked lemonade and she fanned her ample bosom. Sweat would soak our clothes and skin, making her tops almost transparent. She seemed to like me watching her when she would slide an ice cube between her generous cleavage to cool her down. We both wore dark lenses which hid our roving eyes but the twitching mouths and raised brows, revealed the leering ogles that couldn't be denied.

These days started a trend of her wearing conspicuously less clothing. Not many sixty-year-old women could fill-out a bikini the way she did, and she did it just for me. I don't mean literally, but I was the sole audience, when others happened by, she scrambled to cover her sensuous anatomy with a cloth robe or ducked inside to put-on clothes. She was winding down her social appearances and she even toned-down her outfits infront of family. The men missed the deep cleavage and the women were always fascinated with her accessories but she had been pressed for years to "act her age" and the crowd got what they wished for, they hadn't realized what they would be missing. But I felt special. She knew that some members of our clan thought that she was a bit ditzy or an embarrassment. And it hurt her deeply. But to me, she didn't try to disguise who she was. Evie was also a natural born tease and always enjoyed the attention that it brought. Now though, except for my amusement she was stepping on the brakes. It was time to appear a bit more mature.

On any of those occasions, I often asked why she never remarried or let some of those distinguished men squire her around. She would bark in that husky, whiskey laugh and say that the love of her life died before I was born and for me never to forget, that having money doesn't buy class. She would admit once in a while, that she missed having sex. And that "her kitten" as she called it, still demanded attention. Intimating to me in the most obvious manner, that the same thoughts that I had after watching the dirty movies, often lingered in her mind when she crawled into bed, too.

When I suggested that some older escort might be able to help her with that feeling, she answered that "Some old goat loaded-up on Viagra and looking to make a name for himself or a young pretty-boy stud wanting another pelt as a trophy," would only ruin her reputation and cause a scandal to the family name. Then she arched her brows and exclaimed with a hardy laugh, "Besides, one glimpse of these babies and they'd faint dead away." And she jiggled her firm breasts and licked her lips like a seductress. She raised her eyebrow and gave my body a quick thorough inspection, then said that if there were more like me, maybe she could "drop her drawers and let some fresh air in." We both would smile, but I for one, considered the possibilities. "'till then, I'll stick to my magic wand," her pet-name for the variable-speed vibrator she so proudly spoke of. Most of the family assumed she was being silly or being crazy. I knew better.

As the years wore on and Evie hit retirement age without ever having had a job, she did slow down. Her public engagements were limited to ribbon-cuttings or political functions where the family name still held sway. The family believed she had finally decided to quit shocking them with her bawdy language and dredged-up stories with illicit ties to the underworld or bordellos. She respected her place in society and was growing much more demure in public. Nowadays, her entertaining was reserved to family dinners and holiday gatherings, where for most of the night, she was the most gracious of hostesses and set the standard for decorum. She usually let the other ladies do the cooking, but in her own kitchen she would hustle people out or use them as waiters and prepare most of the food herself. Later in the evenings after the youngsters and the fogies departed, she would slip-off her heels and unzip or loosen the ties on her tight bodice and her guests would put their feet up and have that third drink, then more reminiscences would begin. To some, this was a chore or an obligation. For me, it was furthering my education.

The men would get that wistful look, like they wished that they'd had youth and money like in Grandma's day. The women would feign their "Tsk-tsks" as she described scenes of debauchery and orgies that even "modern" women had to frown at. My mother in particular, hated when Evie discussed sex, she often warned me to keep my distance from her but not lose contact. Though Grandma's money was mostly depleted and we never had any, her name still carried weight in business circles and my mother was desperate to enter society. My father just drank her rare scotch and shook his head like she was a "crazy old bat" and wanted nothing more to do with her. She really was trying her best to appear more matronly and to be the respected matriarch of the family. Lower heels and looser gowns became more common.

It was soon after my twenty-first birthday that sexual innuendos and flirty behavior (atleast between us,) really started to flow. Since she, as she put it, "wasn't gettin' any," she wanted to hear about my dating histories and any sexual conquests. She also said that as a birthday gift, she entered me in her will with a generous concession. Our evenings together; after I'd re-painted something or hauled something else, would end with me taking a shower while she cooked us dinner, then we would sit on the couch and talk about sex.

Evie would enquire if I had many dates or a steady girlfriend, and what kind of women I was attracted to. I was not a virgin, infact I'd gotten lucky a few times but I was developing a fetish towards older women. And one in particular. I was constantly thinking that I wanted my grandmother to suck my cock and then I wanted to fuck her. Ofcourse, I never came-out and declared that, but I wonder just how secretive I was being.

This was the first time that I actually considered a plan to carry-out my deviant, incestuous design. I told her "innocently" that younger women weren't exciting enough to really hold my attention. I felt like they had nothing to offer me or to teach me concerning sex. Ofcourse, I was lying and I wasn't sure but that she could see right through me. Though she did drop little bon mots about using my tongue for more than talking, and to make certain that the woman was satisfied and then she would feel obligated to return the favor. But the sexual conversation, mixed with the occasional adult beverage, became steamier and raunchy.

One night after settling on the couch in a darkened room, we were watching porn and sipping drinks. It often seemed like a date, (I knew that I was nervous.)

The videos were never used to instigate sex but served as a form of ice-breaker or background, to keep the conversation and tone of the evening heading in that general direction. She casually mentioned that most couples just don't know what they want or are afraid to actually admit to their base desires. She also remarked that if people could be more open, without being bothered by religious ethics or some prudish moral code, sex in any position with a consenting adult would be freer and easily accessible.

I listened carefully to her sage words and tried to discern any hidden meaning. The temperature in the room always seemed to rise and a sexual trepidation lingered in the heavy air. We always sat close, sometimes whispering for no reason, other times to allow hesitant fingers to strum on bare thighs while emphasizing a point or to subconsciously feel the heat from the other when the steamy scenes reached their climax. There would often reach a point in our own dynamic when something big was about to take place. She drained her glass and smiled at me in a curious manner. Then she said that it was time for bed. I perked-up instantly but she apparently didn't mean me. As she walked me to the door her hand gently tapped my engorged cock through my pants, and she winked, " You should learn the awesome power of this thing, and you'll be amazed how far it will take you." I gulped hard with my heart in my throat, not knowing what the next move should be.

Evie opened the door and I chastely kissed her cheek. A lewd thought raced through my head and my palms grew sweaty. She smiled sadly and withdrew. I faced a huge hurdle but now was the time to jump. "Only the bold...," echoed in my brain. When she turned to go in, I swatted her on the butt, making more of a noise than I anticipated, and said "Thanks for the advice." She instantly whipped around with her 100-watt smile and said in that sultry tone, "Anytime." But her perceptive gaze saw right through me. Though I made a bold move, I was just a scared little boy. She stifled a theatrical yawn and said that it was late. Then she closed the door and I left.

At home, I laid awake and plotted my course, wondering what exactly I had learned. Maybe I was wrong all along but my guts told me that she was teasing me and tempting me, to see how far I would go, and this last interlude was a signal for me to make a move. But I failed miserably. I replayed the last ten minutes in my head and finally discovered all of the clever comments and smooth moves I could have used to prolong the moment and to capture my prey. Her big tits were aching to be squeezed. She had a look on her face, pleading to be taken. And she needed me to seduce her just enough to fall into my arms. My cock was standing straight and throbbing with pent-up desire. I could make this happen. There was one more step. Now, do I risk my family and my future plus possibly the best friend I ever had?