A Taboo Fantasy Pt. 02

Part 2 - The Start

2020 was moving along in about the same manner for me as it was for everyone else: torturously. By March the COVID-19 pandemic had reached my part of the US and I was sent home from my job as a Project Manager at a large engineering firm. While I was partially overseeing projects all over the United States and some internationally, I was stuck at home in Oregon with no way to safely travel to visit them, so all work was being done remotely. I'd set up a home office to work from, even equipped with my business cards that read "Ryan Michaels -- Project Manager"

At first, I viewed it as a nice opportunity to spend a week or two working from home and living the easy life! I was able to spend my workdays on my couch while wearing sweatpants as opposed to the semi-formal attire that my usual work environment required (not to mention no need for the occasional day spent torturing my feet in steel toed boots on job sites), while monitoring sports via my TV that was muted but displaying all of the days highlights. Not to mention the added bonus of extra time to sleep, which as a 27-year-old was something that I still craved like a teenager would.

Like so many others during this time, I also found the added freedom of working from home to be liberating in that any time a random sexual curiosity arose in my often-perverted mind I was able to find time to step away and indulge it. Whether it was a simple search on my phone, a blatant "self-adjustment" that I allowed myself to enjoy for a moment or two (after ensuring my camera is covered of course), or even the occasional time where I'd set my chat app to "busy" and completely drift away into a fantasy. Whether it was brought on by a memory or an online video, I was free to bask in the moment and casually masturbate during the day. It's nothing to be proud of, but we all had to adjust to our new normal in our own ways, right?

This newfound freedom fueled my imagination, albeit almost in a problematic way. My wandering mind made it so that after a few weeks I was struggling to get any work done as my brain started to blur the lines between when was, and when wasn't appropriate to ponder the depths of my deepest-rooted fantasies. Time in between meetings that had previously been spent accomplishing work was now being gradually filled with porn, erotic literature, general fantasizing, and of course, getting myself off.

The more I looked the more I found myself digging deeper and deeper into a fantasy that I'd always had, but purposely attempted to ignore. As time passed and each day's thought process grew slightly more perverse, I quickly found that my searches (and thus my fantasies) revolved around two specific topics: mature women, and incest.

Ever since I was a young man and started "feeling things" about the opposite sex, I had always found myself enamored with the figure of mature women. The beautiful curves of large natural breasts balanced by a robust backside caught my attention immediately. At such a young age I naturally found myself fascinated by (and probably obviously ogling because of it) mature women around me such as teachers, neighbors, and family friends. That is, until one illuminating moment when everything changed.

When I had just turned 18 and was attending a family reunion at my Grandparent's ranch in Montana during the summer after my senior year of high school. My Grandfather had done well for himself in real estate and they had retired to a large ranch in the highlands west of Big Sky where they had a large home built with a focus on entertaining. During this gathering, most of my family including myself and my parents had found available rooms in the main house. My Aunt and her three children would be staying in the guest house that was detached from the main house on account of my niece being just a few months old at the time. We all said it was to give them extra privacy...but the reality was that everyone else was grown and didn't want to be awoken by a crying infant.

One evening we were enjoying a pleasant evening of conversation on their large patio while steaks slowly cooked to a perfect medium rare on their grill. Somehow, such a beautiful setting surrounded by mountains made everything, even the smell of the food, somehow more enhanced. My senses were heightened as I took everything in, partially inspired by the remarkable vacation settings around me but also by a mild buzz from two glasses of wine that my Grandmother not-so-secretly poured for me while my parents rolled their eyes. As my Grandfather pulled the steaks off the grill and called everyone to eat, he turned to me and nodded towards the guest house in the backyard. "Go let your Aunt Lisa know that dinner is ready. I think she went back to check on Anna." Being a good Grandson I replied with a friendly, "Sure thing, Gramps!" and strolled down a neat gravel walkway toward the entrance of the guest house.

Built on a "tiny" footprint, the back guesthouse wasn't much at all, but it did provide a nice space for guests who may need a little extra time away from the larger group. Being that it was so small, my grandparents built it to incorporate lots of windows to make it feel brighter and larger. As I approached the guesthouse I noticed that most of the shades on those windows had been pulled, but I didn't think much of it as we had all been in the backyard and my Aunt Lisa had been trying to get my niece Anna to sleep. Pulling the shades to mute the noise and light made perfect sense. I stepped up to the "front door" and raised my hand to knock when I froze.

While most of the windows in the guesthouse had blinds, three small decorative windows on the door had no covering and allowed for a view into the space that was illuminated with lights as dusk had fallen. What had stopped me in my tracks was the view I had through the door of my Aunt Lisa. A woman who at 40 was a mother of three and stood at about 5'2" while carrying the accentuated curves of being slightly overweight along with the swollen drooping breasts of a lactating aging mother. There she stood, topless. Having just finished a breastfeeding session, her swollen erect nipples visibly stood out from large dark pink areolas still gleaming from leaking droplets of breastmilk, she stood in the main room of the guesthouse scrolling through her phone with one hand while casually tossing her hair with her other, completely unaware of my unrelenting stare. She eventually tossed her phone on the couch, pulled a maternity bra over her shoulders and tossed an oversized sweater on. I quickly composed myself, knocked, and poked my head inside to let her know that dinner was ready. She greeted me with a warm smile and an "Oh thank you honey!" that assured me that she was completely unaware of what I had just seen.

As I walked back to the main house my knees felt weak and my heart was racing. Part of me felt guilty for not looking away from a moment that was intended to be private, but I couldn't deny that a part of me felt an excitement that I'd never experienced before. Seeing something so overtly sexual as naked breasts and yet so forbidden in that they belonged to my Aunt created a curious sexual dilemma that I couldn't get enough of. That entire vacation turned into a haze of sexual self-reflection that eventually led me to undeniable truth. Not only was I attracted to mature women, but I had an incest fetish of some sort as well.

Time passed after that vacation and I'm guessing that everyone moved on, but a part of me never did. For years that memory of my Aunt's breasts was the sole focus of every fantasy I had. No matter what imagery was in my head or what porn I was looking at, anytime I would masturbate her image would almost magically pop into my head. During my college years and well into my professional days, if I found myself struggling to finish with a partner a quick flashback in my memory would almost always be enough to overcome whatever had been holding me back. I found myself completely entranced by erotic literature and porn themed around incest and multi-generational sexual encounters.

The months of 2020 gradually filled with images and fantasies of mature women, relatives and others, each one more sexually visceral than the last. As the grave and harsh reality of COVID set in, I became more cognizant of my own mortality and realized that if I don't live for today, I could end up with mountains of life regrets in the forms of plans that never materialized. While there were practical applications for this train of thought (such as career motivations, financial goals, etc.), it also applied to my personal life. I had lived a relatively reserved life sexually, but it was time to break that mold and become more adventurous. Even in such a strange time as 2020, I needed to explore and see what was out there. I needed to live out my fantasies.

As a single millennial in 2020, I was no stranger to dating apps. I had used many of them and had met several women from them. Though all of them had been women my own age. I was about to throw all of these app algorithms a curveball and try my luck searching for mature women. All of them have their unique attributes which can be good and bad, but I figured I would start simple. Tinder. I opened my profile and navigated to my search settings which were currently seeking women around my age of 27. I grabbed the cursor with my thumb and started sliding. Minimum age: 50. If I was going to do this, I was going to do it right.

As I returned to the "swipe" screen, I was initially met by a few profiles of women in their 50's who had undoubtedly spent years and likely tens of thousands of dollars attempting to keep their appearance like that of a 25-year-old. Badly aging boob jobs, fake tanned skin that's been torqued countless times during facelifts, and stick thin figures. All left swipes for me. I wanted a REAL mature woman. Someone unassuming who has a natural figure and a natural confidence to go with it.

There were a few right swipes that looked promising, but mostly it was all the "plastic" women who just didn't fit what I was seeking.

And then, I found her.

Her name was Kelly. A 60-year-old divorcee who lived in a blue collar suburb about 15 miles north of town. Standing at about 5'4" with a figure that was decorated with about 190 pounds of sensual curves. Her hair kept relatively short and layered showed hints of blonde and red though a natural grey had swept in to become the dominant trait. She stated in her profile that after being divorced and an empty nester, she was looking to meet new people and expand her horizons. All her pictures showed her dressed very conservatively either in a sweater, jacket, or some other bulky top which revealed little of her figure other than failing to hide the curvature of her supple (what I would later learn to be) DD cup natural breasts, along with jeans that did not flatter, but did display the magnitude of curves in her mature hips. Aside from the uncomplimentary nature of her clothing, it was not a shock to see in her profile that she also described herself as "Definitely not a Barbie doll...I consider myself a BBW. Please don't swipe right if you aren't aware of that."

While unassuming, she was perfect. She was the example of the "every day" mature woman that I craved so much. The bitter reality was that I was at a proverbial intersection that so many men have found themselves in. About to swipe right on a gorgeous woman and have her profile disappear, only to hope that she'll swipe right as well. I took one last look at her gorgeous photos, swiped right, and closed the app. It was a Sunday night and a fresh week of work waited ahead so I needed to get some sleep. After another restless night of trying to quiet the perverted thoughts in my mind, I was finally able to drift off.

The Fall morning came too soon as my phone blared it's alarm to jolt me into Monday. As I rolled over in bed to wearily reach for the snooze button I snickered as I felt definitive morning wood tugging at my comforter and was brought back to my teenage days when this was a daily occurrence. Clearly my fantasy thoughts about what could be with an ideal mature woman hadn't ventured far from my mind during the overnight hours.

I lazily tossed on sweatpants and a hoodie while sliding into a pair of slippers to stay warm as my condo had cooled overnight. I grabbed my phone and began trudging to the kitchen to start a pot of coffee as was my daily pattern on a weekday. A quick glance down at my phone to confirm the time brought the morning to an abrupt halt. There was an alert from Tinder on my phone's home screen.

"You matched with Kelly!"

Somehow feeling skeptical that even Tinder was screwing with me, I cautiously opened the app to see if this was in fact THE Kelly that I had seen last night. I clicked on my matches, and there she was. Her profile picture displayed an almost timid smile of hers that acted as a dare. A smile that felt like it was telling me she'd take a chance on matching, but I would have to prove myself from there.

Still groggy at 6:15 AM and while attempting to assure myself that Kelly had in fact intentionally swiped right on me and that it wasn't some sort of mistake, I felt an urge to reach out to her quickly and take the initiative. I combed my brain for the most cohesive and suave greeting that I could muster.

"Good morning!"

I've never been a morning person, but after hitting send on that most generic and unthoughtful message even I felt a wave of fear unlike anything else by potentially getting this conversation started with a non-starter. I sat down at my kitchen counter berating myself for my own stupidity when I saw the "bubble" appear. She was replying.

"Good morning to you too, handsome!"

I was in. I couldn't believe it, but I was in. Feeling slightly more awake and lucid at this point, I was able to put together a slightly more endearing second message by saying, "Today was already off to a good start, but receiving a compliment like that from someone as sexy as you is really unexpected!"

The reply was nearly instant.

"Sexy? You sure know how to make an older woman blush, Ryan."

The smile that crept across my face from that message stayed in place nearly the entire day. I went through the motions of work, sending and receiving emails, updating budgets for stalled projects, and revising timelines of projects on hold due to COVID, but ultimately my mind was elsewhere. Kelly and I spent that day exchanging messages on Tinder, some flirtatious in nature and even a few with distinct sexual undertones, but for the most part it was two people getting to know each other. Our conversation flowed naturally, and we found ourselves messaging well into the evening hours.

As the night wore on Kelly mentioned that she was getting ready for bed but followed it with, "I know we've just been talking for a day, but if you'd like to text me instead of using this app, my number is 555-0132."

As quickly as my phone and fingers could manage, I entered Kelly's contact information into my phone and sent her a text. After a few messages, she said that she was getting ready for bed, but wanted to ask me something before she said goodnight. Then, she sent the question that I knew was coming, but still wasn't sure how to handle.

"You did see my age on Tinder, correct? I'm over twice your age." Kelly said.

"I did." I replied simply and coyly.

After a brief pause, Kelly replied, "What are you doing looking for older women? Shouldn't you be chasing 20 somethings around at a bar?"

Intent on not divulging too much too quickly, I replied honestly though with restraint by stating, "I know it may seem different, but I've always been attracted to women who are older than me. I'd never taken a chance on pursuing it, but with 2020 already making dating crazy, I thought I'd take a chance at complicating it further."

I immediately followed that with, "How do you feel about it?"

Several minutes passed that felt like hours. I could feel my face becoming bright red with embarrassment as I thought I had scared her off or creeped her out beyond a point of recovery.

Eventually, the reply came.

"Ryan, you're adorable. But the difference is significant...like REALLY significant. I have kids older than you! I need to go to sleep, so let me think about it. No promises."

And with that, we said our goodnights. My assumption is that she peacefully dozed off to sleep that evening, where as my reality was far different. My mind was racing with anticipation of what could be, and I found myself scrolling through Kelly's profile pictures attempting to pick out body details in her loose clothing that would further aid my fantasy, and ultimately, my pending stroking of my cock to attempt to quell the fantasies of Kelly that had already erupted in my imagination.

Imagination was fine in private, but I had to remain cool and collected with Kelly. If only she knew how many times I came that night while staring at her G rated photos but envisioning ravaging her, I'm sure she would have never spoken to me again.

The next morning started as an exact repeat of the previous one. Alarm. Reach. Hard-on. Chuckle. I got out of bed and strolled to my kitchen with my sweatpants in full tent mode again. Coffee pot, on. Laptop, on. Camera, COVERED. And just like that, I slid into the start of my workday morning routine like I had for the prior eight months of 2020 when "normal" was completely redefined.

I was halfway through reading my companies daily COVID email update which details all of the positive tests that have occurred at various work sites, when the familiar "ding" of an incoming text message startled me away from the text. I looked over at my phone which had been casually tossed on the desk next to my laptop lit up with an alert. The text was from Kelly.

"Good morning! I hope you slept well! Regarding our conversation last night about the age difference...I need to know more."

Curiously, I replied, "Morning! Ok...what would you like to know?"

Her reply was immediate and direct, "I need to know why."

"Why what?" I replied. Quickly followed up by, "I'm not sure I know what you're asking."

Kelly came back with, "I need to know why you're attracted to older women. What is it that makes a 60-year-old so special that you need to do this? You're a young handsome man and you should be going after girls your own age! Trust me, their bodies won't look like that forever!"

I appreciated the humor in Kelly's statement but also recognized that there was real emotion behind her message and my reply might be important to the entire direction of this budding development. I took a few moments to think before replying, which was called out by Kelly with a "?" text that came 5 minutes after she sent her question. She wanted an answer. In a moment that can only be described as far outside the scope of my character, I grabbed my phone while audibly mumbling the words, "fuck it" before typing my response. It was a response that was intentionally not re-read after typing it so that it would come off as one pure stream of thought. I was going to lay it all on the table for her, and I wanted it to be genuine.

"I told you yesterday that I've always been attracted to women who are older than me. Why? I don't exactly know why. I know that from the moment my balls dropped I saw older women in a different light. Even then I didn't look at teenage girls or girls in their 20's, I saw mature women. Women all around me who were friends and family. Those were the women I was attracted to then, and that's who I'm attracted to now."

The message was marked as "read" immediately. Moments passed by at a glacial rate as I waited for a reply. Feeling terribly vulnerable after telling another person about the incestuous roots of my deepest attraction, I started to panic and needed her to reply. I didn't care what the reply was at this point, I just needed her to say something. She did.