The Bucket List

Story Info
Join Frank as he introduces his gift to the world.
6.8k words
4.12
3.1k
3
0

Part 1 of the 1 part series

Updated 01/18/2024
Created 01/18/2024
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was just before 9PM as I approached the entrance of Eagle Point, by far the most prestigious neighborhood in my city. As I arrived at the gate and came to a screeching stop with brakes that should have been replaced months ago, the security guard stepped out of a guardhouse the size of an average middle-class home with a look of judgement on his face he couldn't have hidden no matter how hard he had tried, while he attempted to politely assess what business a kid driving a banged up 1991 Toyota Corolla could have possibly had in the city's most exclusive neighborhood at this hour on a Saturday night.

(Guard): Can I help you? (in a semi-rude tone)

(Me): Hi, I am going to Matt & Denise Clark's house.

(Guard): What is your name please?

(Me): Frank Purvis.

(Guard): Can I see your ID please?

As I handed the security guard my ID, he stepped back inside the guardhouse taking a few minutes to verify me on the computer before eventually stepping back out to the curb with a look of disappointment on his face as if he were somehow upset that he had to actually open the gate for me.

(Guard): Have a nice evening Mr. Purvis.

(Me): You as well.

As the large castle-like iron gates slowly finished opening, I cautiously pulled through and continued following Waze to the address Matt had provided merely an hour ago. While he certainly wasn't the nicest guy I had ever met, I quickly began to understand the security guard's skepticism of my presence as I passed houses of which I wouldn't have been able to afford in 4 lifetimes of work. Eagle Point consisted of 30 gargantuan estates with a local reputation of being somewhat of a mythical fortress which had been talked about by many, but only seen by few. Waze had me about 3 minutes away from the house, so this is probably a good time to tell you a little bit about myself and what business a guy like me could have possibly had in Eagle Point.

My name is Frank and my life is best summed up as a mostly below-average Caucasian 20-year-old introvert that used the only gift I had been given in this life for all the wrong reasons. I wasn't blessed with the looks or body of a model, the brains of an entrepreneur, wealthy parents, or a trust fund. In fact, I am just a borderline loser high school dropout living in a double-wide in Whispering Oaks Trailer Park that has somehow managed to work more jobs over the past 2 years than I could count on both hands, just to make ends meet.

The summer following my junior year of high school is one I will never forget, sparking a chain of unforeseen events that would alter my life as I knew it forever. Something really strange began happening to me as I couldn't help but think about how my life turned out to be like some fucked up inverse plot to the 1985 movie Teen Wolf in that instead of turning into a werewolf at age 18, I instead hit a second superhero-like growth spurt that somehow managed to target only my manhood. While my below-average petite 5'5", 120-pound frame remained intact, it was as if a cruel joke were being played on me as everything below my waist gradually began to grow exponentially over what seemed like a couple months' time. I struggled adapting to the curse of what had now become a 12-inch kielbasa sized cock, thick as a Red Bull can that suddenly seemed to be in a perpetual state of hardness, paired with set of gargantuan jumbo egg sized testicles to boot. At the time, I felt like a total freak and had an incredibly hard time dealing with what was happening to me.

While I would very soon come to realize the blessing of my transformation, that certainly was not the case initially. In addition to leaving multiple urologist's baffled, my newfound growth spurt had a major psychological impact on me, as things I took for granted mere months ago suddenly became completely flipped on their head. My shorts and underwear no longer fit what seemed to be a perpetually unpredictable gigantic hardon that became impossible to hide in every day clothes, and orgasms I would previously describe as below-average all of a sudden turned into forces of nature, lasting up to a half-minute. I thought something was wrong with me, and the difficulty I had coping with the freakshow I had seemingly become overnight ended up fast tracking a difficult decision I had been pondering over the past year, which was to drop out of high school.

High school was not a particularly good time for me, nor was I any good at it. I was your quintessential bullied introvert with no friends and had already been extremely self-conscious about my petite physical stature as it was. The anxiety and psychological impact of my newfound transformation was simply icing on the cake in a decision that had already been made months ago. While my parents were aware of my horrible grades, I purposely kept them in the dark about the social anxiety I faced every single day, so they were naturally distraught and vehemently disagreed with my decision. Sparing you the details and making a long story short, things escalated rapidly as my decision ultimately angered my parents to the point of asking me move out of the house less than two weeks later, forcing me to find a place of my own with an insulting stipend until I was able to find a job to support myself.

Getting kicked out of my parent's house had initially been a massive shock to my system, but ended up becoming the blessing in disguise that would lead to me finally discovering my worth in this world. Things could not have escalated more rapidly as I began to discover my newfound independence while settling into my crappy stipend funded double-wide trailer in crime-ridden Whispering Oaks Trailer Park, eventually making Door Dash deliveries in my spare time just to make ends meet. A computer previously reserved solely for high school homework had now turned into an introvert recluse' weapon for introducing his unique gift to the world. Escalating porn habits quickly expedited an awareness of the gift I had been blessed with leading almost immediately to jumping head first into the online hookup scene where I suddenly realized that what I had at first interpreted as a curse had ultimately been a blessing all along.

My morale tank had nearly emptied over the next two years as I transitioned from a bullied virgin that had never attracted even the slightest attention from the opposite sex, to a professional sex craved bucket list item for size-queen obsessed women from all walks of life whom would have never given me a second glance in public on my best day. Every negative aspect of my life had now been negated by the picture perfect footlong homewrecker between my legs as my trashy $350 a month double-wide suddenly became ground zero for women spanning every social, professional, and economic class whom were willing to do whatever it took to get their fix. I finally understood what my purpose in life was, and I was very good at it. Inflicting brain damaging orgasms on otherwise happily married soccer moms and trophy wives of whom were physically way out of my league provided a God-like complex I never could have imagined, and eventually led to the added thrill of approving husbands looking on as their significant others had the time of their lives fulfilling a bucket list item. It became like an addicting drug as mostly cooperative ill-prepared men helplessly looked on while their size-queen addict wives, most of multiple decades, turned into unrecognizable lunatics with a total stranger before their very eyes.

Matt and Denise, although a benign experience compared to others, were one of my favorite couples to this day. They were a seemingly happily married high school sweetheart couple of 25 years in their late-40's and brand new to dipping their toes into this lifestyle. Their story was a tale as old as time in this world as years of size-queen curiosity had finally reached the boiling point of turning fantasy into reality. While the dynamic of every couple varied, first time couples were always interesting in the sense that you never really knew which individual had been the main driver in the life altering journey they were about to embark on. In this case, I quickly learned that Matt had never really been on board with the idea, but had somehow finally succumbed to Denise' porn induced decade long obsession of sucking on a monster cock as somewhat of a 50th birthday present to her.

The journey from introduction to meetup typically followed a predictable script consisting of picture exchange, small talk, rules of engagement, and then finally logistics. The picture exchange was always a fun part of the process for me as this is when things actually became real for first timers like Matt and Denise. Denise likely provided her best effort showing restraint to the strategic arsenal of pictures I had unloaded into the chat, as fantasy collided head first with reality while poor Matt sat under an umbrella of regret almost immediately realizing they were inching toward a point of no return. I could imagine an aspiring size-queen like Denise struggling to find a balance between remaining cognizant of Matt's feelings all while having already played out in her head what she intended to do to the footlong salami gracing her screen.

As it became their turn to send pictures, Matt emphasized that they were very private people and was adamant about not sending any face pictures, to which I didn't mind and obviously respected. After a minute or two of silence, I saw a nude picture of Denise from the neck down show up in the chat that immediately screamed "trophy wife" as her smoking hot body resembled that of someone in their late 20's rather than someone close to turning 50. Denise looked petite and likely weighed 115 pounds at most with perfectly shaped man-made D-cup tits that looked even larger than that on her petite body, and clearly defined tan lines that indicated the majority of her free time had been spent on a tennis court. While I had never been overly picky about the appearance of the women I had met, a smoking hot wife that clearly maintained herself like Denise was always an added bonus.

A mere 2 days had passed since our introduction when that eventual message from Matt came much sooner than I had ever expected. "So, how does this work?" it read, almost as a hostage note, as it was apparent things at home had escalated at a much more rapid pace than Matt was likely prepared for. The small talk, Q&A, and rules of engagement flew by as I did my best to ease a clearly anxious man of the life changing decision he was about to green light. While it had been a new and likely uncomfortable position of pimping out your wife to a horse hung stranger on the internet, men like Matt were at least smart enough to read the room and understand that this was likely going to happen with or without them, so he may as well do his best to embrace it. As we got into the logistics, he was originally hesitant about hosting the festivities, but I was able to convince him that this was the best way forward based on my previous experience. We eventually landed on the upcoming Saturday at 9PM four days from then, as Matt told me he would give me directions on Saturday evening.

Back in the present moment, Waze informed me I was arriving at my destination when I saw a monstrosity of a house suddenly come into view on my right-hand side. While it had already been pretty clear from the time the words "Eagle Point" entered the conversation, it now made sense as to why Matt had been hesitant about hosting tonight's festivities. I cautiously turned into the property and slowly began what looked to be a football field length trek up a beautiful paver driveway backdropped by one of the most beautiful homes I had ever laid eyes on. As I approached the top of the driveway and came to a squealing stop, I immediately took notice of the Maserati and Lamborghini SUV, which I didn't even realize existed at the time, sitting mere inches from the dented bumper of my 91' Corolla. I began playing with myself through the white biker shorts I had jokingly decided to wear to really accentuate my colossal gift as I remained in my still running car for a few minutes collecting my thoughts while taking the time to soak in my current situation. While playing the role of bucket list item to size queened upper-class women in front of their husbands had become a routine activity for me, I still couldn't believe an underachieving loser like me had somehow managed to make it inside the fortress that was Eagle Point.

The structural integrity of the bike short spandex was being tested by what was now a fully erect 12-inch kielbasa struggling to coexist with the semen filled grapefruit sized ball sack that filled my shorts like an inflated party balloon. I turned off and got out of my car which had probably already leaked a pint of oil onto their beautiful paver driveway, and began making my way up the long winding sidewalk. I arrived at the double front doors that must have been 12 feet tall, looking more like the entrance to a castle than a house, and proceeded to ring the doorbell without hesitation. From experience, I never expected a first-time couple like this to answer the door immediately. I knew Matt and Denise were sitting nervously somewhere in that gigantic house with their lips glued to glasses filled with wine that probably cost more than my car trying to process if this was really happening. I could recite the conversation with high accuracy that was taking place as the doorbell echoed throughout the halls of their 10-million-dollar estate. "Do you really want to do this?" likely came out of Matt's mouth at least 3 times before the echo of the doorbell had even subsided through the house. I never bothered to ring the doorbell a second time because part of the fun for me was thinking about what they were doing at that exact moment as Matt was likely making a last-ditch effort and pleading with Denise that it wasn't too late to just ignore the door and pretend like this was all just some crazy dream.

An additional 30 seconds had passed as I immediately snapped back into alpha mode when I suddenly saw a shadowy figure approach the front door through the frosted glass which stood there for about 10 seconds before finally unlatching the door lock. As the door slowly began to open, Matt looked like he was in shock as his eyes were immediately drawn downward to the spandex about to burst at its seams while urgently inviting me in, as if he were afraid of somebody seeing me. I entered the very dimly lit foyer and turned around to see Matt still with his head poked out the door, likely observing the piece of shit car that was already reducing his property value just by being in the driveway. The white noise from the outside immediately disappeared as Matt finally closed the front door and hesitantly turned around, nervously putting his hand out, stuck in the awkward phase of trying not to look down at my crotch while at the same time being too embarrassed to look me in the eyes of a man about to fulfill his wife's fantasy. Matt looked like the stereotypical late-40's business man who was "dressed down" in shorts and a tucked in golf shirt.

(Matt): Matt, nice to meet you.

(Me): You as well.

I knew seconds felt like minutes to Matt, who must have been 6'5", towering over me by a complete foot and at least 75 pounds in bodyweight as he finally succumbed to human nature, locking eyes on the absurd spandex wrapped mass that that would shortly turn Denise' decade long fantasy into reality. Likely a man of power and control in his day job, he couldn't have been more of a nervous wreck standing there attempting to make small talk with a guy who wouldn't have been qualified to even intern at the company he ran, wearing a pair of ridiculous bike shorts with a tucked in t-shirt in his foyer.

(Matt): How's it going?

(Me): Doing great, thanks. Beautiful house you guys have here.

(Matt): Thank you.

I really enjoyed watching him struggle to maintain small talk in the 30-foot-tall foyer as if it were somehow going to delay the inevitable outcome of that evening. There was nothing to talk about, as we had absolutely nothing in common, and when it became clear that the small talk had finally run its course, he reluctantly led me into the living room right off of the foyer where I saw Denise sitting on the couch with a glass of white wine as the monster diamond on her finger nearly blinded me as it caught the light. It was my first time seeing her above the neck and while she may have had the body of a 25-year-old, her face looked a little closer to her age and was somewhat of a butterface that had seen its share of surgery and Botox injections, with shoulder length blonde hair. While I couldn't initially put my finger on it, I realized Denise was a spitting image of a classic porn star named Tami Monroe I had become fond of during my early porn watching days. Matt couldn't even offer an introduction before her eyes immediately locked onto my bike shorts as she was caught between mouthing an involuntary "wow" blended with a slight chuckle at what I had been wearing.

I could tell how nervous she was by just looking at her and could also tell she was torn on whether she should get up and greet me or just remain seated. I didn't want things to be any more awkward for them than they already were at that moment, so I approached her from behind the couch as she remained seated and reached out my hand to introduce myself, catching a bird's eye view of the gigantic bra-less fake tits peeking out the top of the black tank top she was wearing.

(Me): Hey Denise, nice to meet you.

(Denise): You too, Frank. (nervously)

The tension in the room was so thick, you could cut it with a knife as she nervously shook my hand, trying as hard as possible to maintain eye contact while openly fighting the urge to look at the clearly defined spandex wrapped gigantic mushroom head pressed firmly against my hip encircled in a pre-cum wet spot a mere 6-inches from her face. Matt hadn't been comfortable from our first chat and certainly wasn't any more comfortable now as he finally came around the couch from where he had been standing between the living room and foyer, taking a seat on the couch a few feet away from Denise. There was a loveseat positioned directly across from the couch they had been sitting on with a table in-between, which I decided to make my way over to, but instead of sitting down, I just stood there with my hands on my hips and a giant grin on my face giving them both an unobstructed view at the real-life version of the pictures Denise had likely orgasmed to all week.

I never saw the point of fake pleasantries or awkward small talk in situations like this. I wasn't here to make friends or pretend people 30 years apart in age could possibly have anything in common. There was no value in pretending I cared about them or they cared about me. I wasn't even old to legally partake in the sharing of a beverage with them, so there was no use of putting them in the awkward situation of offering one. Outside of maybe the first time doing this, I was never again in denial that I was simply an emotionless piece of meat that was here to fulfill a fantasy.

With zero hesitation I took my shirt off and kicked my flipflops off one by one as Denise' eyes remained locked onto my shorts like a fighter jet onto its target. While I wasn't typically one to enjoy taunting, I would be lying if I said I wasn't moderately enjoying how uncomfortable Matt appeared to be in this moment. The dynamic of meeting up with rich people like Matt and Denise turned me on more than usual as I knew I was providing a priceless service that all the money in the world couldn't have purchased. With essentially no other place to look, Matt was all but forced to study my colossal spandex wrapped anatomy alongside his wife as I stood there with the giant grin that never left my face. There were a lot of directions I could have gone at this point and perhaps would have gone with another couple, but ripping the proverbial band-aid off seemed like the best path forward with a first-time couple like Matt and Denise.

12