The Chance Fantastic Pt. 02 - The Roots

Disclaimer: This is part two of 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.

A few weeks had passed since I first visited Vivienne's Grotto. I had switched back to normal porn for the first week, but that didn't stick. For some reason, I couldn't get the idea of sissies out of my head. So I eventually came back. Jennifer wasn't there to greet me, but Sissy Amanda was. As was Sissy Christine. I learned that Amanda went by Manny in his everyday life, and Christine, unsurprisingly, went by Chris. Chris worked as an accountant. Manny was a university student. They were nice enough, and happy to share their favorite sissy videos with me.

I had started by exploring more of the Leynadecker series. I had figured if I started with 5, then there must be a 1-4. I think 4 was my favorite. It was set up like a video game. The sissies on the screen leveled up as they performed increasingly depraved acts. First, they got all dressed up in lingerie. Then they shaved their bodies. Then they started seducing men. And so on and so on. After I ran out of Leyendecker videos, I started asking around the chat room, and Amanda and Christine were the most eager to help.

Of course, their video recommendations came with some other recommendations too. Amanda asked me if I was wearing panties yet. When I told her no, I was really just here for the videos, she brightly responded that watching these videos in panties would be a whole different experience. When I was about to politely rebuff her again, I started thinking about that and my penis grew harder than it ever had. So instead, I just said, "Really?" and she almost immediately shot me a link to a website that sold panties for sissies. I looked at it for a bit, but just to get my heart going. There was no way I'd spend real money on panties.

Christine told me she had just shaved before hopping online today. She told me that feeling her own smooth legs turned her on so much, and that her ass never looked better. I couldn't help but check out my own ass in my mirror - it was fairly flat, and unremarkable, but the worst part was definitely the hairy asshole. Nothing could be less attractive. My legs were about the hairiest part of my body. I could see why shaving them might enhance the experience, But also, I loved to wear shorts. Of course, that wouldn't matter, as it was fall.

I heard a knock on my door. I quickly closed out of the browser. A bit flustered, because I was still rocking a boner, I opened the door. It was Greg, carrying a basketball, "Hey man, you want to go shoot around for a bit?"

"Of course, let me just change." Greg and I often did this. I was pretty terrible at basketball, despite its status as my favorite sport. I was an avid fan of the NBA, but my lack of coordination, aversion to the gym, and height always put me at a disadvantage on an actual court. Still, it was fun to go shoot around in a non-competitive environment, and Greg often used these times to engage me in philosophical, political, or ethical discussions.

It was one of the things Greg loved most about me. Greg had a natural curiosity about nearly everything, and as a sociology major in college, had just experienced a lot of different viewpoints for the first time. He would find excuses to get me alone and pick my brain. I was well-versed in a lot of different subjects, and I alone among our friend group read the newspaper daily. He would pepper me with questions about things he heard at his job, or current events, or sports, and I would do my best to answer as expansively as possible.

When I got out to the court, Greg was doing a mini-game of around the world with himself. He seemed a bit less talkative than usual. I started my usual routine of jacking up threes that I would hit at an abysmal rate, content to let Greg get the conversation flowing. Eventually, Greg said, "Did you hear about Becca?" Becca was the last girl Greg seriously dated. Or, at least, tried to seriously date. Greg was head over heels for her, but she never committed to him, for whatever reason. Becca was bright, fun, and had a winning smile. She and Greg seemed like a great match whenever they were around each other. It mystified everyone that they never really went steady, despite Greg's best efforts.

"No, I haven't. What happened?"

"She's engaged. She's only been dating him for like a month too."

"That's crazy - I didn't even know she was dating."

"You really don't spend much time on Facebook or Instagram, do you?"

"Nope - social media stopped being fun after high school."

"So I take it you haven't seen a picture of him?"

"Nope."

"He's bald, dude. Bald. Like, I'm cool that she didn't want to date me, but she could have done better than that."

I laughed. Leave it to Greg to be just a little superficial. Still, he had a point. Becca is super cute. She could have had her pick of guys. Her fiancé must have one heck of a personality. But I could tell Greg wasn't done with the conversation, "Sorry about that. I always wondered why she didn't end up with you."

Greg, surprisingly, looked a little abashed, "There were just some things that didn't work between us."

"I don't mean to pry man - you don't have to tell me anything you don't want to."

Greg stopped shooting. After a moment, he started again, clearly ready to talk some more, "Nah, it's ok. I trust you. There were just some things I needed to work on. I wasn't ready to be in a serious relationship, I guess."

Now, that statement, out of context, could mean a lot of things, most likely among them that Greg just had some growing up to do. And I suppose that could still be true. But in my Church, in my culture, "needing to work on things" generally meant one thing: Greg had a pornography problem. Pornography was strictly forbidden by my Church. In fact, any sexual act before marriage was forbidden. And while girls were pretty good at toeing that line, it was common knowledge that pornography and masturbation were widespread among the male youth of the Church.

The funny thing was, no one talked about it. You could hear statistics saying that over half the guys in a congregation partook in pornography regularly, but everyone in that room would act as if it were the most disgusting thing in the world, and that they would rather be caught dead than look at pornography.

It was easy to explain the dissonance. Sexual sins were considered the third worst sin you could commit by my Church. For context, the second worst sin was murder. It was worse than alcoholism, stealing, or ordinary violence. It was a sin that required a confession to a bishop, and, post-confession, a host of consequences. If you confessed to viewing pornography to a bishop, you would be forbidden from going to the temple or from partaking in the sacrament on Sundays. These were public events, which meant that if you didn't eat that little piece of bread, everyone would know that you were some sort of big sinner. And the temple thing was even worse: marriages were supposed to take place in a temple, so if you couldn't go in, you essentially couldn't get married. And a girl who wanted a family was unlikely to wait around for some serial masturbator to get his act together when she could have her pick of liars who kept their sins hidden.

All this helped explain Baldy and Becca a little better too. She had finally found someone to take her to the temple. Maybe that's why she wanted to get married so fast - that way, he wouldn't have time to screw things up. I tried my best to console Greg without letting on that I knew too much, "Yeah, that happens. It's just timing when it comes down to it. You'll find someone soon who appreciates you as you are now - that's really what you need to be in a relationship. I hate it when a girl dates a guy hoping he'll become someone else soon."

"I know, right?" Greg seemed energized by my comment. "Like, I want to change, and I want to be better - who doesn't? It's just hard. All I want to do is get married, and have a family, but I know I can't until I change. But the longer it takes for me to change, the less hope I have to get married and have a family, which makes me less motivated to change. It just sucks."

"Yeah, the vicious cycle. And the real pernicious thing about all of this? The best way to change is to be open and honest with others around you about what you need to change, but as soon as you do that, those people leave you. But you'll get it, man. Like I said, sometimes it's just a matter of timing."

Greg looked thoughtful. He had stopped shooting again. "You know what I'm talking about, right?" Apparently, I had played my hand a little too strongly.

"Yeah, I mean, it's not exactly uncommon, is it? And don't worry, I don't think any differently about you."

He looked doubtful, shrugged, and turned to shoot again. I could tell he wasn't exactly comfortable with me knowing about his problem. I had to level the playing field somehow. Looks like it was time to take my own advice, "Yeah, I mean, not to make you too uncomfortable, but I have the same problem. It happens - you work through it, and deal with the consequences when you screw up. It's nothing to be ashamed about."

It worked. Greg relaxed. We obviously didn't want to stay on the subject too long, so we soon started talking about sports, and before long, we both called it a day. It was getting dark anyway. I said goodbye and he went to his apartment as I tromped up the stairs to mine. I was thinking of maybe throwing on a movie before dinner.

As I climbed into bed, laptop up ready to search my illegal movie sites for some rom-com I hadn't seen (romcoms were a guilty pleasure of mine), I thought about my conversation with Greg a little more. There was a fundamental difference in the approach we each had to the same problem. See, for Greg, it was still a problem, one that had to be solved. He was broken, and he had to be fixed. After years of struggling with a pornography addiction, and never receiving the promised help from God to help me eliminate my sin, I had given up. I understood that pornography could and probably would affect any romantic relationship, but I stopped thinking of myself as broken, as evil. Instead, I was just a normal guy, and a pretty decent one at that. I was respectful, at times charming, and a hard worker. I was generous with my time and my money. If a girl didn't like me for that, that was fine. I was sick of feeling inferior just because I had sexual urges. That giving up was a big reason why Church was such a slog these days. I really only went to maintain appearances with my family and friends. God, I needed a wider social circle.

And speaking of social circles, before I knew it, I was in Viviene's Grotto again. I hadn't even realized I was pulling it up. I didn't change my username this time. I wasn't interested in talking with Jennifer or Christine, who were both in the room. I didn't even know how long I was going to stay. I just wanted to watch some sissy ass for a bit. I edged for a bit (I finally found out what that word meant after a trip to Urban Dictionary), watching as sissies in lingerie, or naked, finger their asses, get throat-pounded, or do whatever degrading act was thrust upon them flashed by on my screen. I loved when their faces were covered in cum and spit. I loved their thick lips and round asses. I felt excited, but I also felt like an orgasm wouldn't be enough right now.

Without closing out of the Grotto, I opened a new tab, and opened Google Maps. I did a basic search for "adult stores." I don't know what had gotten into me. I think I was ready to try one of the gurls' suggestions. The nearest store was called Dirty Jo Punster, and it was about 20 minutes away. How expensive could a pair of panties be?

I felt that awesome mixture of nervousness and excitement as I picked up my keys and headed back out the door. It only got stronger as I got closer to the shop. The shop itself was old and slightly faded, part of a collection of small independent shops on an aging main street. It had a window where inside a mannequin was displayed wearing some tasteful purple lingerie. Taking a deep breath, I had that feeling I got right before I started a test of some sort. Starting was always the hardest part. I had to approach entering this store like ripping off a bandaid. In one quick motion, I opened the door and quickly slipped inside.

The store was dark, and filled to the brim with racks and displays. No one else seemed to be there, at first. However, I soon heard a friendly "Welcome! Let me know if I can help you with anything," from the back. Not wanting to talk with anyone, I just said "Thank you," and moved on, starting to explore the cramped walkways between corsets, stockings, and bras.

The front of the store seemed to be dedicated to clothing. The men's section was fairly small, as to be expected. After all, females are the object of sexual desire, not the other way around. So the vast majority of clothes were meant for women. Bras, panties, lingerie sets, fishnets, leather corsets, slutty schoolgirl outfits - it was all here. For a time, I was content just to wander, and orient myself in the store. I had to try to figure out the strange organizational system.

The panties that were more prominently displayed had a much higher price than I anticipated. I mean, $30 for a thong? That seemed ridiculous. Eventually, I found a small collection of assorted panties in a sort of exposed drawer organizer in the center of the shop that were discounted. They were still sexy, and had costs ranging only from $6 to $15. I made a mental note of where it was, but I had more shop to explore.

I hadn't intended on buying anything other than panties, but now that I was inside, I found myself wanting to look at some of the other items. I went over to a wall where they had a whole range of stockings and fishnets. There was something so sexy about a woman in pantyhose, and I couldn't help but wonder what I would look like if I put on some sheer pantyhose. After looking there for a while, and noting that the prices seemed reasonable, I moved on to a wall of boxed roleplay costumes. These, too, were less expensive than the versions displayed near the door and windows, and on the racks. Most seemed about on par with some of the slutty Halloween costumes I had seen, and I wasn't too interested in those. If you could wear them on Halloween, they weren't slutty enough to immediately invite thoughts of going to the bedroom.

I paused. What was I thinking? Why would I want to wear something that would invite someone to the bedroom? I wasn't going full sissy, was I? I just came to get a pair of panties to wear while masturbating, that was all. I just wanted to make my porn-watching sessions just a little bit hotter. I didn't want to engage in this lifestyle, right? But then again, if wearing panties got me hot, maybe wearing a garter belt and stockings would get me hotter? How far would my quest to be turned on take me?

I quickly returned to the panties. I resolved to at least get those. Besides, I had to think pragmatically as well, despite my lust-fueled mind. I needed to set myself a price limit. It had to be something that wouldn't draw too much attention on my credit card statement. Not that anyone saw those, but you have to plan for contingencies. Fifty dollars seemed appropriate. There's no way I would spend more than fifty dollars on women's underwear just to make my dick a little harder during masturbation.

But as I moved into the back of the store, I adjusted my estimate. No more than one hundred dollars, I thought to myself. The back of the store was different from the front. First of all, the store attendant was back here, organizing what looked like a new shipment of lingerie. She was a little shorter than me, and had a brunette pixie cut, glasses, and several piercings. You know, standard punk, or even manic pixie girl sort of look. She was older, probably mid-forties, and thin. She was wearing a black mesh shirt with a purple undershirt and some black jeans. She was neither attractive nor unattractive, in my evaluation. I did my best to ignore her.

Second of all, the back of the store was not dedicated to clothes. Instead, it had everything else you might seek when coming into a sex shop. Dildos and vibrators were everywhere, along with lubes, strapons, BDSM gear, fleshlights, butt plugs, anal beads, gags, the works. There was even a small section of old-fashioned pornographic DVDs. It was by far the most taboo part of the shop, and my heart was racing. I had never before been able to imagine what a store like this would look like, and the manner of advertising the various naughty tools.

I had gotten into porn that involved toys a while back. Dildos could be hot. I mean, they were used extensively in lesbian porn. Besides, having just gotten into pegging, it's not like I couldn't imagine using one on myself. Just generally, I wanted a hot girl attached to one. Before I knew it, I was standing in front of a dildo. It was flesh-colored, about eight inches long, and not too thick. It had balls attached to the base and a suction cup. It only cost about forty-five dollars. At that moment, an image appeared in my head with such force, it almost caused my cock to rip right through my pants (not really, but sometimes I get carried away with imagery).

I saw myself, dolled up like the sissies in my videos. Long hair, makeup, schoolgirl outfit, pink stockings, riding a dildo as men and women tipped me in my stream. I think every guy at some point had fantasized about what it would be like to work in the porn industry. I was just envisioning a new role for myself. But what really grabbed me was the fact that this image felt attainable. It felt real. I could never hope to achieve anything as a guy. I was too plain, too boring, too average. But as a girl, I could be hot. And then, I could sell sex for a living. And that sounded wonderful.

I quickly had to step back. I could hardly believe what I was thinking. But I was thinking it. If I wanted to try out how hot this path could make me feel, I might as well go all the way. Why make multiple trips to this store, when I could instead satiate my curiosity in one go? If I was so torn about what to buy, caught between being a normal guy just trying to get off and someone attracted to the sissy lifestyle, why not try as much of the sissy lifestyle as I could? I made up my mind. I knew what I wanted to buy.

First, the panties. I quickly found three sets I liked: a pair of red cotton boyshorts, which I always thought were sexier than people gave them credit for. Then, a pair of pink and black bikini-cut panties, with pink frills down the butt, and a pink little bow on the front. I wanted to get at least one extra girly option. Finally, I got myself a lace and silk black thong. It was the sluttiest of the three, with a lace panel in the front, and a silk string that would definitely ride inside my ass. That felt like a good variety, and enough to experience if any of them would make me feel sexy.

I then went back to the wall with the stockings and got myself a pair of neon pink fishnets. They would go great with the $20 schoolgirl outfit that came with a pink plaid miniskirt, a white crop top, and a little pink plaid choker tie. I figured I could see how my figure would look. If I was fucking myself with a dildo, I wanted the image in a mirror to seem girly. That would be much hotter than seeing a guy, just like in porn. I was tempted to buy more - a corset would give me more of an hourglass figure, heels would help lift my butt, a wig would help hide my man-hair, but I was fast approaching my monetary limit, and I had at least one more item I knew I wanted to buy.