The Last Gentleman Caller - Cover

The Last Gentleman Caller

Copyright© 2016 by GonzoJournalist

Chapter 1

Fiction Sex Story: Chapter 1 - Nick is a 19-year-old college hipster whose only concern in life is hooking up with girls via Tinder and social media. But he gets an assignment from his school newspaper to interview his annoying, nasty old great-great-grandfather, Edward, who at 114 years old, is the oldest living World War I veteran. The two find out that they might actually have a great deal in common.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   Consensual   Romantic   Fiction   Historical   Humor   Interracial   Black Female   White Male   Size   Big Breasts   Slow   War  

Edward Jameson Calloway didn't understand the younger generation.

Nor, did he quite understand the older generation. He still called all of them "beatniks", even though his grandson Teddy, a New Year's Day baby in 1942, just turned 72.

That is, he would call them "beatniks" when he had good days, when he was able (or rather, chose) to speak.

Whenever Edward's great-great-grandson, Nick, Teddy's grandson, came to visit, the old man had a habit of knocking Nick's hipster cabby hat off of his head and smiling a mischievous, toothless grin.

"Your grandfather got over that beatnik mularkey," Edward would complain, his lips flapping and his voice creaking like an old phonograph. "And I won't have another beatnik while I'm still here!"

The 114-year-old man loved the dark comedy of saying things like that, alluding to his impending death that seemed to never come.

Edward also had a habit of flirting with his nurses when they made home health care visits, which was darkly comic in of itself.

Edward was an unabashed old pervert, enjoying the freedom that being a supercentenarian provided.

When he knew his nurses were due to visit, he'd put in his false teeth and practice his toothy grin. Even after all these years, he was able to crook his eyebrow so he could give the young nurses "the eyes." He made every effort to have "game," as his 25-year-old great-great-granddaughter Lindsey called it.

"They used to call me 'Fast Eddie, '" he'd brag to his nurses in his slow, labored drawl, "and fast was how long it would take me to get a doll like you into the sack."

He even made every nurse promise that if he could ever manage to get his old cock hard, they had to kiss it.

Each of them sweetly agreed, obviously taking it as a joke, and Edward absolutely loved that he could get away with acting like that. But, he was quick to point out, he acted like that for most of his life.

Oddly, being an old pervert endeared him to those around him. He was so full of life, whether it was being a surly old goat or ranting about the world or the President ("They've all been pussies since FDR," he'd say), that he seemed like he could live another 10 years.

On the days that he couldn't bring himself to talk, or simply didn't want to put out the effort, he'd managed to learn how to use a tablet. He'd type things out on the screen and show it to his grandson Teddy to communicate his need for food, help to the toilet, or help with a bit of exercise. He even learned how to make memes on his tablet, which, if the Internet knew that there was a 114-year-old man that would sometimes communicate to his family via memes, Twitter would absolutely break.

The thing that Edward liked the most, though, was that his tablet gave him the option to not engage with the world around him if he didn't want to.

However, as generally joyous and humorous as the super old man was with his family, he only seemed to grunt and snap at Nick. There was something about Nick that rubbed him the wrong way. Even though he was family, there were times that Edward wished he had the power to punch Nick in his stupid curlicue moustache.

Nick felt Edward's rage, so he kept his distance whenever possible. When Nick would come by to help his grandfather Teddy around the house, Nick would only grunt a "hi" to Edward before retreating to some other corner of the house.

Nick was 19, and as was the case with most 19 year olds, he was obsessed with social media and meeting women - when he wasn't studying, writing term papers or writing columns for the University student newspaper. Nick's online life gave him a good distraction to avoid most of his family, especially Edward.

Edward would often notice that Nick always had his nose in his phone, rarely ever speaking. He found it absolutely genuinely baffling. Lindsey wasn't as connected to her phone as Nick, and Edward wondered what was so interesting about Nick's phone in particular.


"Just so you know, the scent of your perfume still lingers on my pillow. Seems you leave quite an impression ;-)"

Five days ago, Nick Calloway's fingers twitched and tensed, texting out that veiled plea to Kaylee Conrad.

For five days, he'd waited.

His most recent message was the fourth in four days that he forlornly sent to Kaylee, each more casually desperate than the next.

And none warranted a response.

Monday: "I haven't heard from you. Which I wouldn't blame you for. My legs are still shaking, too ;-)"

Tuesday: "Is it in poor taste to simply text 'You up?'"

Wednesday: "Is everything okay? I had an amazing time with you last week. I'd love to see you again."

Then came Thursday's message, about the scent of her perfume, which he wrote and re-wrote for about eight minutes straight before settling on the word choice and punctuation. When Nick finally sent it, he immediately regretted it.

"It's corny," he thought, wishing he could recall it and send a different message. "It's trying too hard. It makes me sound like an idiot."

Ever since Nick sent that particular message five days ago, he had glanced at his phone every 30 minutes on the off-chance that she wrote back. Granted, if Kaylee indeed responded, his Mario Bros. coin message notification on his phone would have done the job of alerting him that she actually did want to see him again.

However, Nick's addled mind lost touch with reality days ago.

He pondered Kaylee, which he'd done countless times the previous two weeks. He had never gotten so bent out of shape over a Tinder hookup. But Kaylee was wickedly sharp. She was sarcastic and witty. Her style of dress was a throwback to the 1950s, half Bettie Page and half Audrey Hepburn. And it didn't hurt that the raven-haired, crystal-eyed goddess absolutely oozed sex; Kaylee's every casual shimmy of her hips and crooked mischievous grin reeked of raw yet regal sexuality.

As far as Nick was concerned, she was the complete package.

And Nick knew all this from one date and one tempestuous night. The best word to describe their two nights together was "epic," though Nick would rather gnaw through his wrists with his teeth than stoop to that overused adjective to describe anything.

Instead, while he waited and waited, there was a whole lot of "swipe left, swipe left" as he continued his search for The Next One.

Tinder was an addiction that had a very swift onset. It was a different sort of vibe for Nick, one that was in stark contrast to his otherwise humble beginnings.


Technically, Nick didn't get laid in high school. He actually waited until the Class of 2013 had already ascended the stage, snagged their diplomas and moved their tassels to the left before he finally got a girl. On graduation night, Nick, still unadorned with fresh adolescent acne and greasy hair, lost his virginity to Megan Massey at her graduation party.

The nerdy blonde girl confessed her years-long lust for Nick. His one-time lab partner in 9th grade, Megan, a chubby and quiet girl, told Nick she'd had the hots for him ever since she saw him pop a huge boner during freshman biology class. It was the type of thing that would gross out a normal girl, but Megan wasn't a normal girl. She found it hot that Nick apparently was turned on by her freshman year, and it took her all that time to voice her approval.

Blushing painfully but ridiculously curious, she told him that for the past four years, she just "wanted to see it." Nervously, he obliged.

Only three minutes later, Nick and Megan were screwing in her garage as her family-friendly graduation party continued just outside. Megan's physical pain during their coupling was enough to make it a one-time-only thing, and just two weeks later, she had left for Chicago as she prepared to start her freshman year at Northwestern University.

He tried not to let himself fall hard for Megan, but he did. He was confused as to why it was so easy for her to blow him off. Nick wondered what was wrong with him.

To avoid something like that again, Nick had to change. He made the conscious decision that, once he began college, he would do his best to impress the fairer sex by adopting a new wardrobe and amplifying his interest in offbeat music, movies and literature, all while looking more grown up.

He essentially decided that he would, in fact, become a hipster, without using that exact label. His goal was to attract attention from women, which he absolutely craved when he was in high school.

He quit shaving, letting his beard grow full. He opted for glasses instead of contacts, getting thick black Buddy Holly-esque frames. He'd often be seen wearing some combination of cabby hats, plaid dress shirts, suspenders, high-water slacks and wingtip shoes. Somehow, thanks to his boyish looks and striking emerald eyes on his olive complexion, Nick pulled it off and didn't look like a nerd. His finely-kempt beard played a big role in that.

He had to work full-time to support his lifestyle of fashion and pop culture, getting a job as a line chef's assistant at a sushi restaurant. But, even that job certainly gave him hipster cred, as the restaurant was quite the hopping hotspot for the trendy locals. His hipster cred was further fueled by his position as a critic and columnist for the University student newspaper, focusing on music columns and the occasional pop culture musing. It was quite the coup for a young freshman, but Nick did have a talent with the written word.

In his own little world, though, he was beginning to become well-known. It was in stark contrast to Nick's life in high school.

His changeover didn't pay immediate dividends socially, as he made friends with a few guys but not any women. His meetings with his buddies, usually at coffee shops near the University, were often a circle jerk of lumbersexuals desperately hoping that girls would notice them.

Despite that, for the first time in his life, he felt confident. Nick was confident enough to begin biking to class every day as well as join a local curling league that ran out of the city's ice rink. Every few weekends, he'd play in bocce ball tournaments at a local pub, which was also technically a "sport," he reasoned, as he began to get in shape. He became slim and toned in just a few months' time, benefitting from his youthful metabolism and constant biking.

But, he couldn't get any girls, try like he might. He was very reserved and wasn't the outgoing sort, and that probably played a big role.

Part of Nick's more core hipster proclivities involved being a technophobe. He avoided smartphones and social media throughout high school as a philosophical choice. He would jot down ideas, musings, poetry and lyrics in a series of notebooks that he used much like other teenagers used social media. On occasion, he'd let friends look at them, but often, it was a solitary practice.

He also avoided iPods and MP3 players. He was more of an advocate of the cassette tape mix. He used his late father's old boom box to create mixes, then design fold-up cassette tape liner notes for the mix tape cases. He'd design a cover, draw it, and transcribe lyrics, just like the tapes in his dad's old collection.

These practices made him a complete dork in high school, but as an adult, these actions served his persona quite well. Even if he didn't have a lot of his friends, for the first time in his life, Nick actually felt somewhat secure in who he was.

It wasn't until college that he took the plunge into the 21st century, finally getting an iPhone chiefly for the functional use of making phone calls. Then, by the time Christmas break came along, he opened a Tinder account.

With his new outlook on life, his first foray into Tinder was moderately successful. During his first week messing with the app, he landed himself two dates, both of which didn't lead to a second date, but at least he got that far. However, that success was combined with over 50 rejections, some being rude enough to nearly break his spirit.

Looking to improve his chances, his Tinder presence quickly prompted him to craft his online persona. He took his first selfie of his life when putting together his initial Tinder profile. Then he upgraded with another. Then another. Soon, he got prolific at taking them, realizing selfies showed off the stylish look that he so meticulously crafted, and later, showed that he might actually be datable. All of this led to his first Instagram account, as well as his decision that he would NEVER get on Facebook, only using it to authenticate his Tinder account.

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