The Chance Fantastic Pt. 01

Disclaimer: This is a long short story, maybe even a novella, if I knew what the requirements of a novella were. While each chapter includes sexual content, this is about slow escalation. Events building on one another, leading to greater and greater payoff. It only gets more intense with each chapter. So if you want to get to know characters, and be plunged into a world that is a shade more believable that your standard porn set-up, I promise you, the payoff is worth it. I plan on adding a few more chapters as I go forward. Big thanks to brewster926 for some steady story editing.

The Chance Fantastic Pt. 1 - The Seed

I felt that familiar feeling as Church entered its third hour. It was a restless, bored, unfocused sort of feeling. It happened almost every week. I swear I don't have ADD, but long period of sitting and listening to someone drone on, with the occasional self-righteous show-off telling a personal story about how they "overcame" temptation, always caused my mind to wander. During these times, I couldn't focus on one thing if I tried. And I tried.

I would try reading ahead in the lesson. I would try counting down the seconds ticking away. I would turn each second into a fraction of how much time was left, and turn that into a percentage, and try to get up to 50% of the time passing me by. I would try to plan my week, or organize my thoughts on what needed to be done before work started again the next day. Inevitably, I would try daydreaming. It used to be my favorite activity, writing epic stories in my head starring none other than yours truly. Even as I got older, and the daydreams became less fanciful (but possibly more romantic), I can still drift off on a good car ride or if I was ever having trouble sleeping.

However, in Church, when my focus was at its lowest, these daydreams would often turn from the bright and hopeful to the degenerate and naughty. Now, I don't think that's unusual for a young 20-something single male. But I don't know why my mind would go to those places while sitting in a Church specifically. Maybe it was because the lessons so often told me I couldn't think about those things. A classic case of "don't think about elephants."

And so, I started thinking about porn. I had been watching porn fairly regularly since I was fairly young. I know some guys got started earlier, and some later, and some lucky guys, whether because of dutiful commitment to their decent upbringing or because they were so empowered in real life they had no need to fall back on manufactured fantasies, never got started at all. But for me, in my conservative household, it was relatively early. A friend at school had mentioned how if you changed a letter in a popular website, it would bring you to a pornographic domain. I had to try it as soon as I got home. When my parents found it in my search history, I got the dressing down of my life, and a considerable grounding to boot. My parents, at the time, harbored hopes that would be the end of it. I think I did too. Needless to say, it wasn't. It was just the beginning.

And the funny thing was, at the time, I didn't go onto that website because I needed to see naked women. Naked women were almost tangential to my exploration of that website. As soon as Isaac mentioned it, I felt the thrill of adrenaline race through my body. It was honestly the taboo that got me. It was my chance to do something I wasn't supposed to do, a chance I had rarely gotten at that point. And that feeling never went away for me.

It drove me back to porn a few short weeks after the first incident, this time armed with knowledge of search histories and how to clear them. Eventually, it drove me from naked pictures to short video trailers featuring naked women. Then I discovered true lesbian porn. After I had mastered the art of something, be it accessing porn without my parents finding me out, reading porn stories on my ancient flip phone, or downloading 30-second porn trailers over my parents basic dial-up without them finding out, I would soon feel that the porn had lost something of its edge. So I would level up my game, and try again.

Sometimes I got caught. Most times I didn't. And that's the story of how I became a regular consumer of increasingly more hardcore pornography. My sexuality had gotten tied up in the taboo nature of porn, especially in my household and my Church. It didn't help that I went to a university funded by my Church. I think that just reinforced my desire to be "edgy," even if no one else knew I was doing anything. Because I am anything but edgy in all other facets of my life.

I was a good student and am a good employee. I call my parents at least once a week. I visit my grandmother regularly. Friends know they can count on me, and I never get involved in the drama that often occurs in other people's lives. I'm polite, don't cuss, eat fairly healthy, don't drink or smoke or do drugs, and I don't really like extreme sports. I invest a substantial portion of my income into my HSA and Roth accounts. I pay off my credit cards every week. I avoid the stock market because I don't like the risk. I have plenty of friends because I'm easy to get along with, and no girlfriend because I almost never put my feelings on the line. I'm average height and weight, white, Christian, and middle-class. I'm even a middle child. No, there's nothing risky or edgy about me at all, which is why it confuses me that sitting in church makes me think of girls and guys getting fucked in the ass.

Anal had been my most recent category of choice of porn. I particularly enjoyed casting videos that pretended to be a girl's first time receiving anal. They would put the camera in front of her face, and another one behind her so that you could see her facial expressions side by side with the actual ass-fucking. I had been in this phase for a while, which meant that I had started to push the boundaries of what was to be included in the category. And that had led me to the discovery of pegging.

Now, I'm sure some people got the appeal immediately, but I didn't. I didn't know why I couldn't tear my eyes away from a hot girl in leather, with straps perfectly framing her round ass, pounding the hairy ass of some random dude. Porn had always been about the girl for me. It's why lesbian porn was my first go-to - no dicks involved at all.

Eventually I conceded that having a guy there made things hotter and more intense, but I still wanted his role minimized. I didn't want to hear him, I wanted him fairly clean-shaven, and I mostly only wanted to see his dick, particularly while it was in the act of pounding a hot girl's mouth, pussy or asshole. But pegging put the whole guy front and center, and it seemed wrong to the intellectual part of my brain.

The instinctual, primal part of my brain, however, couldn't have been more turned on. I was still mostly focused on the girl, but now for some reason I could see myself there, in the room. There was something intoxicating about the idea of a girl dominating me like the guy in the video. Maybe my lack of dating success had subconsciously convinced me that the only way a girl would accept me is if I was nothing more than a piece of meat in front of her, a groveling man who worshiped her body and strap-on appendage.

And so my brain ran off in this direction while the Church lesson slogged on. I was thinking about what sort of searches I would do to find more and better pegging videos when my friend Greg nudged me, breaking my heated reverie. Hoping my cheeks weren't too flushed, I subtly shook my head to try to wake myself back up to reality before turning to look at what he was trying to show me.

Greg was a fun guy, full stop. He was roommates with my best friend from back home, but now I hung out with him more than Jordan. Greg was a kid at heart. He was always doing stupid things, like making bets with girls that he could beat them at tennis using his off hand, or trying to get other friends to kiss their crush by shooting a basketball at half court. Greg was a serial dater, with a new girl every week. Now, because both of us belonged to a religion that didn't believe in sex before marriage, the worst Greg ever did with these girls was make out with them, but boy, had he made out with quite a few girls.

Greg was a little taller than me, about 5'10, and in shape. He was an avid long-distance runner, and he loved any sort of game or sport, even if he could only be described as above average at best at any of them. He had dark hair, looked a bit stocky for his height, and he always had something of a twinkle in his green eyes. His hair was neatly combed, he had a small goatee, and, like me, at the time, he was wearing a white shirt and tie with some dark slacks.

Greg, unlike me, was what I liked to call an instigator. He had ideas for fun things to do, and then he got people to go and do the fun things with him. It was the reason he and I got along so well. Although I never instigated, Greg knew that I was flexible, and could be roped into doing pretty much anything. For my part, I enjoyed it when someone else carried the burden of making sure the day was fun. I just like to go along for the ride.

That was probably why Greg was showing me that Brad Paisley was coming to town. I was not really a country music fan, but I enjoyed a good concert regardless of genre. I told him as much.

"Brad puts on amazing concerts - they're more like shows. Plus, he's really funny. We should go," Greg whispered excitedly.

"I'm down. I never have anything planned that far in advance, so I have no conflicts. Let me know what the tickets cost."

I probably should be more judicious with my money, but I worked as a paralegal for a rapidly growing tech company, and, as a single guy with inexpensive tastes, I always had enough to go around. Greg grinned at me and proceeded to use the rest of the class to buy the tickets. I was just happy that it was almost over. I had a fantasy to get back to.

Greg and I walked back together, joined by Jordan and his girlfriend. Jordan's girlfriend Abby was another reason Greg and I had been spending more and more time together. See, Abby was Greg's younger sister, which made it a little awkward for them to hang out. Besides, they wanted to be alone as often as not, so Greg and I just moved on without them - he without his sister and me without my best friend. Still, we enjoyed their company on the nice day. Jordan flatly turned down the offer of going to the concert. He wouldn't be caught dead at a country music event. Abby didn't have the money to go, and wasn't interested in going without Jordan anyway.

As we got back to the apartment, Greg declared it was time for his afternoon nap. Jordan, still in the midst of getting his business degree, said he had some homework to do. That freed me up to head up to my room for some private time.

I lived two floors above Greg and Jordan (their third roommate, Will, was almost never around). My roommates Johnny and Stewart both helped out after Church with planning activities for the congregation for the next week, so they weren't home yet. Even with an empty apartment, I made sure to discreetly lock my bedroom door so that I wouldn't have any unexpected visitors.

Out of habit, I turned the lock slowly enough so that it wouldn't make noise - that was something else I learned growing up. The click of a lock, unless it was for the bathroom door, was awfully suspicious.

After changing into something more comfortable, I fired up my laptop. Pulling up an incognito browser, I typed into search bar "gurl pounding guy." It wasn't my most imaginative search yet, but I was still beginning this new fascination. I didn't bother correcting the typo. Google always had my back with those things.

I scrolled through the search results. I almost never clicked on the first link these days. It was always one of three main free porn sites. I liked to search for something a little different, a little less mainstream. However, that meant developing an eye for shady, low-quality products that would deliver essentially the same thing as the big websites, but with an extra helping of viruses for your computer. So I scrolled for a little bit, glancing at descriptions, but not settling on anything in particular on the first page of results.

On the second page, something grabbed my eye. It was a reddit list of rooms where you could watch porn videos anonymously with strangers. The idea of the room initially struck me as odd, like a porn movie theater or a porn shop. You know, public places where people go to be titillated. I never understood the concept.

Masturbation was an inherently private act; why go and do that in a room full of equally pathetic people? Wouldn't seeing them remind you how pathetic you looked in the moment? Wouldn't that kill the vibe?

But then I thought a little more about this website. It wouldn't be like masturbating in public. I'd still be here, in my room, alone, with no one to see me. The videos on the screen would be the same. The only difference is there'd be a chat function where I could see how other people thought. Maybe they could give me some ideas on where to look next for porn.

Because I lived in a repressed society that actively discouraged talking about sex with other people, an open conversation with strangers about porn sounded kind of nice. I decided to give it a try. Clicking on the link, I found that the page was astoundingly pink, which surprised me. Without much context, I clicked on the first link, innocently entitled Vivienne's Grotto, without looking at any of the others.

A video opened on my screen, with a chat box next to it. I was automatically entitled "Guest27," though I had the option to change it if I wanted. The videos apparently played on a endless shuffled loop, and the most recent video was coming to an end. A new one started right after, and I felt that familiar surge of adrenaline as I anticipated the depraved acts that some incredibly hot, curvaceous women would inflict on some poor sadsack.

The video first showed a title screen, and it was just called "Leynadecker05." I assumed Leyna was the mistress in this video. It started with some hot girls dancing in lingerie at the beginning. A techno beat played in the background. It was different from what I was used to - dungeons, bad acting, leather - but not unpleasant. As the images went by, I started to hear a whispering in the background, but I didn't bother to make out the words. Soon, the girls were rubbing themselves.

Suddenly, I thought I saw something strange. It looked like one girl was doing the action of stroking her cock. The image was gone in an instant. But soon another one happened like that. I started to feel my pulse pounding - the strapons were coming out. After a few seconds of rapid images, of girls rubbing themselves in lingerie, stroking their strapons, techno beats, and whispering, a new, unmistakable image popped on the screen.

That girl didn't have a strapon. She had a dick. That was a real dick. I was taken aback. For the first time, I looked at the other names in the chat. They were all talking about "edging" (whatever that was) and how hot the girls wore. They had names like "Sissy Jennifer." I was about to leave the page, recognizing that this wasn't what I had started out looking for, when something in the video caught my eye.

For the first time, I understood the whispering, "You're going to be my little camwhore," it said as a "girl" onscreen stood in a miniskirt and stocking. Likes and comments started flooding in on the video of her getting complimented. Dance for us, one comment said. Spread please, said another. One simply said "strip, bitch." I felt a weird feeling, a mixture of that adrenaline and...jealousy? Did I want to be desired like the guy in the video?

I mean, I had always envied girls. They had it easier, in my opinion, when it came to dating. Sure, they didn't get to choose who pursued them, but at least they didn't have the job of pursuing. They didn't have to risk that rejection. A good looking girl would be approached, and she would know, definitively, at that point that the guy was interested, whereas the guy just approached, hoping to God that the girl found him attractive or desirable. And in my experience, more often than not, she did not find him attractive or desirable. I always wished we had lived in a more egalitarian dating society.

With trembling fingers, I decided to use the chat, typing ever so slowly "hey everyone, what's a sissy?" I felt that there was no turning back as I hit enter. It didn't take long for Jennifer to give me a response. "Welcome Guest27! Thanks for asking - it's a lifestyle. Sissies are all about sexual pleasure. We live for giving and receiving pleasure. It's what we're all about."

Jennifer came across as a lot more put together than I would have guessed, given that we're all in a room watching porn together. But I suppose if I was in a room like this, it was conceivable somebody like me was also in the room. Sometimes my ego was just too big, I admitted to myself.

"Thanks for the welcome, Jennifer. So do all sissies dress like girls?"

"Most do. Being a gurl is most of the fun! Plus, it lets us communicate our needs nonverbally - we get to dress, walk, talk, and act slutty. That puts us in more sexy situations ;) but how girly a sissy gets is up to the sissy. Some just dress up during private time, some are more committed by shaving their bodies, and others go full trans, with hormones and surgeries. What kind of sissy you are is up to you!"

"I'm not so sure I'm a sissy. I ended up in this room by accident."

"Sure, an accident ;) that's how most of us got here. But you'll soon be back, I promise. Is there a name I can call you, honey?"

Not comfortable giving out my real name to a complete stranger, I went with the first name I could think of, "James." But Jennifer had made me think. Sure, I didn't intend to end up watching this video. But here I was, nearly five minutes into it. In a normal porn session, I might have already cum by this point, but I was distracted by the chat. The video was still hot, and the buildup to an orgasm was the best part of masturbation. I had to admit, I was kind of enjoying the environment.

Maybe my ever-evolving interests would lead me back here naturally. Besides, what did it matter anyway? If I enjoyed a video, I should just sit back and enjoy it. There's no harm in that. Still, I had a few questions that were nagging at me.

"Jennifer, are all sissies gay?"

"Not at all, hon! A lot of sissies are straight, and dress up to play with their wives or girlfriend. Other sissies totally live and die for cock. Personally, for me, when I'm dressed up and in sissy mode, I'm in a total femme state of mind, and I need cock. But when I'm in my boy clothes, I am fully straight, and not attracted to guys at all. That's one of the best things about being a sissy. It fits your lifestyle, and it's all about what makes you happy."

Jennifer sounded so positive and confident. I thanked her, and went back to watching the video. The girls were hot. Other than their dicks, they looked just like real girls in all other respects: breasts of varying sizes, big round asses, smooth skin, soft features, fuckable lips. The fact that it was always anal titilated the primal part of my brain. I also couldn't help but notice that they all seemed to be having so much fun, just like Jennifer said. They really seemed to crave putting a cock in their mouths. If a girl like that approached me with that sort of eagerness, I knew I couldn't say no. The whole scene was so erotic and taboo. Now that I was done chatting, it didn't take me long to cum at all. I wondered how long it would take before I came back.