Bucket List of Sex Ch. 01

Story Info
Bishop's time is short, so he hires an escort to gain manhood.
4.4k words
4.33
4.6k
2

Part 1 of the 1 part series

Updated 10/22/2023
Created 10/22/2023
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Bishop waited in the doctor's office anxious for what awaited him, for the past few months every time he woke up, ate, or did anything it was met with a long arduous cough. His chest ached thinking about it. Even though he always had an uncertain feeling whenever the doctors were mentioned to him. He couldn't wait any longer, he needed to see them, and today was the latest checkup for a long bout against his tattered lungs.

An RN pierced through the awkward silence of the waiting room, she reviewed the name on the checkerboard before speaking. "Bishop Walker?"

He arose adjusting his polo shirt pulling on the seams so a little bit of his sides weren't exposed from the tugging of the belt.

"T-Thats me," Bishop spoke with an awkward stammer.

"Right this way please," The nurse didn't think anything of it, and she spun, guiding them both into the depths of the chambers of life and death, as well as the minor physical.

Bishop noticed her short hair wave at him as she turned. Her light shade of brunette sparkled under the bright fluorescent lights, and the shine guided his eyes to the rest of her. It took a little bit of willpower to not have a slight eagerness to look at her ass, which had a perfect shape and fit to her already well-worn scrubs.

"Okay, here is the room your doctor will meet with you any moment."

Bishop just nodded. He always hated these moments. Those pieces of time catch you at an odd time, between readiness and uncertainty. His friends and family kept telling him that it was maybe a case of bronchitis or a fit of asthma that he never realized was even there. In the back of his mind, however, it felt more than that, something inescapable.

"Hello, Bishop is it?" The doctor entered, carrying a stack of papers more so than any usual check-up.

"Correct."

The doctor nodded, forming a slight grimace as he sat down.

"So what did the tests say? Bronchitis? Asthma? What is it?"

The doctor sighed looking at the papers again. "I don't know how to tell you this Bishop but... You have a growing case of lung cancer...From the looks of it."

Bishop licked his lips and nodded, Even though it wasn't the punch in the gut like he was expecting. He still felt a sly hint of defeat.

"Now we can try and get you on chemo, get you on meds but that will only relieve your pain for some time."

Bishop looked away, feeling the coarseness of his hands. "I don't think I will be able to afford that, I only do construction... Do you think I can give it some thought?"

The doctor made a grimace looking as if he was afraid of that response. From what Bishop figured, if a patient said this, they weren't coming back. Which is what he had in mind.

'Of course," his doctor responded, "You know your way out."

Bishop nodded trying to hold back a few lines of water streaking from his eye. He didn't know what he was supposed to do anymore. As a matter of fact, from what he remembers from his life he isn't sure he had done anything at all.

He hasn't seen his friends and family for years due to his job, alongside this, he was practically a virgin. Only really ever having his shaft played with at the end of prom. Bishop thought of all the things he wanted to do. All the things he could do. And it struck him.

He was losing his virginity this weekend.

The moment Bishop returned home he was already booting up his laptop... Looking for the best, and most reliable site for an escort.

"There isn't enough time for me to try my luck at a bar or library." Is what he thought. Clicking on the first link he found when he typed the line 'Best escort site' in the search bar. He could have sworn that he was probably flagged by his local police for looking for a viable woman to spend the night with. But he didn't care.

It didn't even take a second for him to guide his pointer to the link of lust and desire. He took a moment to read the website description

Precious Comforts: For all your feelings that reside under the table.

Bishop felt like he was in the right place.

It seemed like hours for how many pages he scrolled through. Looking at every single member who was willing to fulfill his wishes.

First, there was a supposed shy but lovable companion. Bishop noticed that she had all the right angles to make someone stop for a moment. Even just enough to click on the link. From her profile. She was a petite Hispanic woman, with small curves and small perfect bumps breasts, which was just enough to make Bishop tug on his pants. Then another woman was right up his alley. She was a light skin woman with a nice round ass that jumped out of the frames of her profile pictures. And from the look of her profile. She was open to everyone and everything.

But none stood out more than the last profile he had seen. Her name was Iris, just Iris. Most escorts make it an unspoken rule to go by an alias if they aren't well-established. But it seemed like Iris was new, and she didn't care who knew her name or not. Bishop rested on her profile just respecting her honesty and openness:

I'm Iris. No, it's not some kind of sly nickname, my name is Iris. Let's cut to the chase. You wanna have sex with someone on this website. And like having it so why not pay me to do so? Hit me up if you ever wanna chat. Later.

Iris was not only open but was goddamn beautiful in Bishop's eyes. She was a curvy Asian woman whose light brown eyes struck right at the camera. Her lips were plump and glossy pink. And her hips were bountiful with an ass to boot. Which made itself known from the royal purple lingerie that she wore for her profile pictures.

In every sense of the word Bishop knew she was the one. He wanted her in every sense of the word. And so, he sent her a message. Hoping for a response


Bishop bounced his leg against the table's supports. It took an awkward back and forth for a few days to even find the time to meet each other. The two settled on the first Saturday of the month. At a local coffee shop.

"It's already 11:15 she's late," Bishop spoke to himself. Sipping his coffee. He pursed his lips together feeling the aftertaste. He wasn't much of a coffee person, favoring energy drinks more since they were more convenient for his job. Plus, he didn't like doing the dishes.

Once he pressed his mug back down he felt a tap on his shoulder.

"Hey, Bishop right?" A rough but gentle voice spoke out.

"-yeah, yeah you Iris?" He nearly choked on the rest of his coffee

"Well, who else would it be?" She said in a curt tone.

She exited Bishop's peripheral before reentering to sit at the chair across from him.

"You're late by the way. You said noon, it's currently 11:17 a.m." Bishop opened up.

"Well... it's a good thing you haven't paid me yet." She said before pausing "So why do you want this?"

Bishop pushed his coffee to the side, attempting to add sweetener "Want what?"

"Come on man you want me to spell it out for you? THIS." Iris gestured to herself letting the edges of her fingers rest at her cleavage poking from her jacket.

"Are you sick of your wife or something?"

"I'm not married, and what does it matter you're getting paid right."

"Of course, I simply like to know why my clients have... well this desire."

Bishop paused a little wondering if he should tell her the reason "It's personal."

Iris scoffed "okay... okay... Interesting motive."

Bishop raised an eyebrow "What about you? Why are you in this profession?"

"It's personal," She responded pressing her tongue to her cheek

"Touche."

They both paused a little each taking sips of their drinks

"Alright well here's my ground rules," Iris spoke up

"You wear a condom, I don't wanna get an STD when I'm just getting started.

Bishop nodded and she continued "It's $140 upfront, and it's only Incall. After we're all done it's another $240 got it?"

Bishop was quite surprised at how cheap it was. Every other escort had a set amount of money for every hour on the hour and they all ranged above the price she was asking for. Even including the deposit this was far less than what Bishop was expecting.

"Deal," He said, taking out his wallet. "Cash only correct?"

Iris nodded, watching Bishop count the 20s stopping at 7. She was still fixated on the extra forest still residing in his leather wallet.

"Here 14-," Bishop spoke before a violent cough itched from his lungs and lingered in front of both of them

"Geez dude you alright?" Iris asked

"It-It's nothing, don't worry about it," He said, coughing a little more.

Iris looked at Bishop a little longer before wiping it from her mind "All right, I'll send you my address as soon as I leave. But be ready with everything. Capiche?"

Bishop sat silent rubbing his throat and giving her the o-okay sign. Iris gave a sly smile before leaving a 10 dollar bill on the table and wandering off "See you then," she said

Bishop couldn't help but look as she walked, her arms in her jacket pockets and ass and hips swaying from the side before blending into the crowd

It was then at that moment Bishop received a text message

"1874 Grover Ct NW, come tomorrow night, 9 pm."

"Noted, see you then." Bishop responded. He felt a little weird talking like this. It felt like he was going to a normal hang-out with an old friend he hadn't seen in a while, but he guessed that was the magic of the escort industry.


Bishop grew anxious as the special moment he prepared for himself came to greet him. He was 30 minutes away. Yet now, the biggest thing he was concerned with was his attire.

"No... too casual... Not too formal..." He said throwing clothing after clothing on his bed. He eventually settled on a pair of Linen trousers and a white t-shirt.

As he set to leave, the clock grew closer and closer to 9. Stopping at a pharmacy to grab a pack of condoms. The old lady gritted her teeth a little as he scanned the 10-pack of condoms.

"11.34." She spoke and was still eyeing him. Bishop didn't say a word, just moving on.

When Bishop approached Iris' home he wasn't entirely sure what he should do. He kept his car idle as he shot her a message.

"I'm here, mind letting me know if I'm in the right place or not." He messaged, waiting a little concerned he just got scammed and was pulling into some nobody's house.

That thought escaped his mind once the door opened. Light from inside the house flooded into the driveway. Illuminating his surroundings while also keeping Iris transfixed into a pleasant silhouette. He could tell all she was wearing was lingerie as the only other piece that he could point out was a nightgown, which wrapped itself firmly against her hips and figure.

"You're late by the way, it's 9:10 you were supposed to be here at 9," She opened up as Bishop exited his car

"Well considering the fact I needed to get condoms it's a good thing you got your deposit."

Iris smirked a little "touche," turning back into the house. Her ass poking just a little underneath her silk nightgown.

"Nice place you got." Bishop spoke up.

"It's rented, the furnishing is mine though" Iris responded. "Wait right here."

Iris gestured to her couch. As Bishop sat down it gave him a chance to relax and take in his surroundings.

Despite being the very cordial type, it seemed like Iris had many things that she took fondly. Plants surrounded the insides of the house, vines and floral decorations throughout. It gave a nice earthy scent that the Bishop welcomed. Compared to the ample amounts of concrete, gasoline, and oil that bonded to his sense of smell, it was a nice change. Not to mention the colorful posters of movies and bands that managed to find space in between the abundance of plants and flowers.

"Alright, are you ready?" Iris spoke

Bishop looked over to her standing between the halls. It was clear royal purple was her favorite color. As it was the same lingerie panties she wore on her profile. As well as a purple ribbon that tied a piece of her hair in the back, balanced by two long strands of her hair straightened out into the front. The strands of hair covered the most intricate parts of the breasts. Despite being a new patron on the site he found her Bishop knew she was already a master of her craft.

"Take a picture, it'll last longer," Iris spoke, blushing a bit. She walked over to him sitting at the other end of the couch trying not to move too harshly for her hair to move past her nipples. Not too far to be out of reach from one another. But just far enough to set some eagerness.

"So um... how do we start?" Bishop

"Well we can start in any way that you want... we can chat, watch a movie... kiss... I can also..." She reaches a hand over, caressing Bishop's thigh, "Suck your cock"

"I think I'd like to kiss, that works for me."

Iris nodded, sliding herself over to meet Bishop in the middle. She guided her hand over his pants nearly brushing his bulge before guiding his lips to meet hers.

Her lips were soft. Tasting like cherries which Bishop presumed to be from a lip gloss that made her lips dance in the sunlight. Iris pulled him close, moving his arms away so she could move to straddle him. If the kissing didn't send Bishop over the edge, this did and Iris was in full control. She guided his hands to her ass.

His hands pushed, squeezed, and played with read melting away

"Don't be shy," Iris spoke up "You can give it a nice spank if you'd like."

Bishop obliged, winding his hand back and letting the air glide out of his way, slapping her ass firmly with an open palm.

Iris moaned, letting out a fiery determination. Fill her once-withdrawn eyes

"Mmm mhm harder," She moaned.

Smack

"Harder..."

Smack, smack

"Fuuuuck harder."

Bishop reeled back once again, excited that he was able to overcome this obstacle of manhood. But as he was willing to come again with the full force of his hand he stopped

It was that itch again, that persistent itch in his lungs that spoke that the only destination he was to arrive in a few months was in the ground.

In the coming moments, he wished to just enjoy the feeling of finally fulfilling a long-lost wish but it needed to be put on hold for now.

"H-hold on-" Bishop mustered before following into a prolonged cough

"Oh um...okay," Iris let out feeling a little let down as it was just about to get good

"Where's your... bathroom."

Iris pointed down the hall and Bishop pressed on without a second thought. He gathered himself spitting into the sink with each cough he let out.

It wasn't till the final one where he spat out some blood that he stopped.

"Ahh, well... shit," He proclaimed entering the living room again

"Holy crap man you alright?" Iris asked wearing her robe again

"It's.... Nothing."

"Doesn't sound like nothing, what is it you got going on?"

"I said it's nothing I promise... can we just continue?"

"Sorry, I don't think so not until I know."

Bishop looked confused "What're you, my mom? This doesn't have anything to do with you"

Iris gritted her teeth "Look man If you want to continue this I need to know what you got, it is for my safety. You got the flu or something?"

"No..."

"Covid?"

"No".

"Fuck man HIV?"

"W-what? no!"

"Then what is it?"

"Fuck alright, cancer! It's cancer..."

Bishop looked defeated sitting back on the couch "I got diagnosed with it a week ago, even with money saved up it'll only give me about another year."

Iris caught herself "f-fuck man I'm sorry."

Bishop sighed "Don't bother, it was my decision. The reason why I never went with the treatment was because I didn't get many people to consider friends, even family. So I thought to myself why to bother giving yourself an extra year to stay alive for nobody? When I could just spend that money on doing things I wanted to do."

Iris looked a bit puzzled, glancing at herself "So have sex with an escort?"

"No actually, truth be told I'm still a virgin."

Iris' eyes sparked up, she tightened her silk gown and sat next to Bishop, closer than before. "No shit?"

"No shit."

Iris sighed a little, but it wasn't those sighs that you would catch anybody of her temperament to do. It was a sigh of catharsis and relaxation. "I live on my own because I don't have any family either." Iris opened up. "My family's real religious, and I'm just not. We never got along sooo... I decided to leave."

Bishop looked back at her "Are you a sex worker be-"

"No- it's not because I am doing it to spite my parents, I wasn't kidding in my profile. I like having sex, so I might as well get paid for it."

Bishop nodded.

"Thought since you let out your whole M.O. would only be fair to let out mine."

"Fair enough," Bishop smiled, and Iris smiled as well.

They let the silence fill the air just taking in what each other said. Bishop never really had a moment aside from his doctor to just reel in his reality. But it felt good.

They looked back at each other, sharing a different kind of want than what they had before. Originally they only wanted each other for what they could offer. But with the moment of kissing and spanking, followed by a small personal chat their needs evolved to something more... Passionate

Bishop leaned in again. Kissing Iris' soft lips again, and she let him without a second thought. His tongue knocked ready to greet each other and she obliged. Swapping spit, and breaths together.

They pulled and tugged at each other for a moment before their efforts got the best of both of them, slipping on the ground. Yet that didn't stop them, Bishop gathered himself crawling back to meet Iris, kissing up her chest and the crevices of the nightgown

"Here let me just..." Iris says releasing the grasp the nightgown has on her body. Sliding it off Bishop stops mesmerized by the soft mounds in front of him.

"Don't just sit there... go and-" Iris stops as Bishop lets his mouth play games with her nipples, flicking his tongue back and forth like a joystick.

"Ahh," Iris cooed, playing with Bishop's hair.

The Bishop's cock ached and begged to be released and it would grant its wish. As Iris tugged at the buckle.

Bishop didn't waste another second, taking his trousers and letting his boxer follow. His cock flicked up with a stringed web of precum following suit.

"Get comfortable big boy I'm about to make this the best night of your life." Iris moaned, taking the base of his shaft and stroking it with a slow yet graceful pace.

"Fuck Iris," Bishop let out feeling the pressure already

"Ahh ah you're not allowed to finish quite yet," she demanded.

Iris took the moment to relish in Bishop's discomfort before swallowing the tip of cock. Bishop could only moan and watch.

Up and down, taking him deeper.

Up and down, gliding her hand in a circular motion with her mouth.

Down, and down till she reached the base of the member.

Iris did this motion another time before pulling out with a long breath. Kissing Bishops tip for good measure. Yet she still didn't let go, pushing him to his upper limit as she massaged his mast with all her saliva.

"Holy Shit Iris..." Bishop exclaimed.

"Shhh, just don't stop looking at me" Iris responded.

Bishop focused all of his efforts on maintaining that eye contact that she so craved. Her light brown eyes, fixing a soft gaze at him were enough to set anyone over. But Bishop knew he needed to hold on.

Iris began to slow her pace down. Knowing that if she continued Bishop would be at his wits ends. Her hands were sticky. From all the mixings of precum and saliva.

"Are you ready to become a whole new man Bishop?" She smiled

Bishop nodded. He watched her stand up with this pressing firmly together creating a barrier for her whenever she tried removing her panties. She dropped those purple-laced underwear to her ankles and kicked them down the hall.

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