The Chance Fantastic Pt. 03

Disclaimer: This is part 3 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.

The Chance Fantastic Pt. 3 - The Sprout

I really tried to get away from it, I did. Sure enough, after I changed into my thong and fell asleep with the silk nestled between my pale ass cheeks, I woke up feeling disgusted with myself. I couldn't believe I had spent so much time just watching porn and masturbating last night - almost 3 hours worth of it when all was said and done. I needed to clean my dildo, which was just abhorrent to me in the morning light. Dried lube and...other stuff...on a fake cock was not at all attractive to me now that I wasn't horny.

After showering, and cleaning my room, I very nearly through all my recent purchases away. In my head, I had experimented, and it just wasn't worth it. Sure, I partook in porn regularly, but I was still a regular guy who wanted to live his life, make money, get a girlfriend, and maybe eventually get married. I didn't want to become some sick porn addict, or worse, a sissy. But as I held my frilly pink panties in my hands, I just couldn't bring myself to do it. I had invested too much into this. Could I really throw away all that money I spent on these things after just one night of fun? Could I even discretely throw these things away without being caught by a roommate?

I'm not sure if I decided to keep everything or just decided to make the decision later. Regardless, I instead found a dark corner of my closet and hid my clothes and dildo in there, where they were sure not to be found by visiting friends. And then I moved on with my day, going to work, socializing, finishing the day with a normal movie. I avoided porn altogether that first day, and the day after. When I did return to my habits, I tried to watch more vanilla stuff. A casting couch video here, some stepmom porn there. It worked. It wasn't great, but I got off, and that was all I needed. I moved on with my life.

One day, about a week later, I was hanging out in Greg and Jordan's apartment with them. Jordan was getting on Greg's case for not coming to the gym with him. I suppose now would be a good time to explain my and Jordan's history. You would never guess that we were best friends growing up. We couldn't have been more different. In high school, I was skinny, with a shock of long brown, unkempt hair. I was ostensibly a nerd, but a charming and socially competent one that everyone seemed to like. Jordan, on the other hand, at first blush, was your classic jock. Blonde hair, blue eyes, three sports. Jordan was good-looking, a good student, and fairly normal. And yet, whether because he didn't try as hard as me, or because he was just a little awkward, Jordan seemed to depend on me for his social status, as opposed to the other way around.

We almost became friends by accident. We went to the same church, and due to being close in age, always ended up doing things together. We would give each other a hard time as part of an ongoing game to see who could get the better of the other. I would make fun of his intelligence and awkwardness (though he really wasn't stupid or awkward) and he would make fun of me for being skinny and unathletic (which were totally true, but I couldn't care less about them).

Jordan had long ago tried to convince me to work out with him, but I had better uses for my time, those "uses" being almost anything other than going to the gym. I was of the mind that exercise was bad for your health. I mean, anything that made you feel that physically bad could not be good for you. The runner's high was a myth. Exercise was just a ploy by the government to keep the masses mollified. Needless tosay, I had convinced Jordan to give up trying to convince me to go with him a long time ago.

So, instead he went with Greg. Greg did not hate the gym as I did. What Greg did hate was getting up early, and Jordan liked to get a workout in before his 8 am classes. Apparently, Greg had officially given up.

"Oh, come on, you really won't go anymore?" Jordan was asking.

"I'll make you a deal: I'll get up in the morning when he starts coming with us," Greg quickly retorted, nodding in my general direction.

Jordan looked at me, "Great. Now you're infecting all my gym buddies."

Taking on an air of mock offense, I replied, "Sure, I'm the problem. You're the one that insists on getting up at an ungodly hour, and then jogging to a gym in below-freezing weather. I'm fairly certain that's a classic case of torture, per the Geneva Convention."

But secretly, I had been toying with an idea recently. Going to the gym could actually be good for me. I knew that working out was linked to releasing all sorts of endorphins, and instilling some healthy habits in myself could only help me resist my unhealthier habits. "But hey, I'm feeling a little masochistic recently. I think you could convince me to go."

"Really?" Jordan sat up. "You know I leave at 6 am."

"Yeah, I don't have to be at work until 9. It works out. And even I'll admit, I'm super out of shape. I may even have to drop the 'skinniest' qualifier from my title of 'skinniest fat man alive.'" That last part had been an inside joke with me, Jordan, and his younger sister. We had once gone to the beach together, and she was wondering why I hadn't taken off my shirt. I explained that even though I looked skinny with my clothes on, due to my extremely poor BMI, I still looked fat when I took them off. I was the skinniest fat man alive.

"Alright, you want me to come get you up?"

"Nah, just unlock your door when you get up, and I'll come down when I'm ready."

"That means you're in, right Greg?"

"Come on, Riley, you screwed up my plan. We'll see if I get up."

The next morning, I woke up at 6, threw on some sweats, and went downstairs. In high school, anytime I actually convinced myself to go with Jordan to the gym, it was always with vague hopes of building a more masculine set of shoulders. I had essentially no upper body strength.

Now, however, I was old enough and wise enough to know that I would never have the discipline to stick to a weightlifting routine. Besides, I hated protein powder, and I didn't really know how to "bulk up." But I didn't hate running quite as much as I did fruitlessly trying to build muscle. This time, I just wanted to lose a few pounds, and get in good enough shape not to die every time down the court in basketball.

I sat in the dark on Jordan's couch. I could hear him getting ready in his room. I heard him go into Greg's room. When he came out alone, I figured he had failed to rouse the beast. So he and I just set off on our own.

It was freezing outside. The gym was only about a mile and a half away. I say 'only' as if I was in shape like Jordan. It was a killer jog for me. It didn't help that I had a touch of cold-induced asthma. Jordan, of course, hardly looked winded by the time we got to the gym. At the gym, I got out my headphones, let him know that I was just going to be doing some more cardio, and we parted. Getting the treadmill up to the speed I wanted, I started to drift off.

As always in a public place, I couldn't help but scope out if there were any hot girls around. The gym wasn't packed at this hour, but it also wasn't empty. And there were a few hot girls. I won't lie, girls in workout clothes were a major turn-on for me.

I had never been that fashionable a person. I definitely prioritized comfort in my own wardrobe. When a girl also wore similar comfy clothes - leggings, sweats, a t-shirt, etc. - I think I related to her better. So a girl could be wearing a super modern or fashionable outfit, and it wouldn't do much for me. But put a girl in a pair of leggings or bike shots and slap a t-shirt on her, and I couldn't stop staring. It was the one good thing about the gym.

I watched this one girl for a while. She was skinny and had a dancer's build. She had long, almost waist-length platinum blond hair. She wore a black sports bra and bright pink leggings. She was doing some sort of squats while holding some dumbbells. She had one leg back, on a small bench. After a while, she would switch legs. Then, she stopped using the bench, and let the dumbbells between her legs, bending at the knee. It really pushed out and emphasized her ass. I was quite appreciative.

Soon, she laid down on a mat, put a dumbbell on her waist, and thrust up. If she was a guy, it would look like she was practicing fucking someone riding her cowgirl. Next were a series of bodyweight exercises that involved kicking and moving each leg in circles. Almost before I knew it, a half hour had passed and I was still watching the girl in pink leggings. Time never went that quickly for me while running, but it had flown by this time. She had been a much better distractor than my music. I started my cool down, and went to look for Jordan.

The rest of the day passed normally. At night, I couldn't get pink leggings girl out of my head. She wore fairly heavy makeup. She had a passing resemblance to petite blond pornstars, the kind that always starred in teen movies as your horny stepsister. Pink leggings girl seemed more genuinely innocent than that, but I couldn't stop thinking about the curve of her ass as she worked so hard at sculpting it. The leggings looked tight, but comfortable, like a second skin. I would love to wear leggings.

And with that thought, I figured out why I couldn't get that girl out of my head: I was jealous of her. She was hot. I wanted to be hot. I wanted to go to a gym in pink leggings, and have the people around me appreciate my body. For the first time in a little over a week, I fired up my computer, and returned to Vivienne's Grotto. As a video started playing telling me to bimbo-ify my body, I chose a username: rjsissygurl.

As soon as I hit enter, a chorus of "hey rjsissygurl" and "welcome to the party" pinged through the chat. Sissy Jennifer was on. I pm-ed her: "Hey Jennifer, it's James. I don't know if you remember, but a few weeks back I was a newbie to this site and you helped answer my questions about sissies."

"So you're back, hon ;) see, I knew you'd come back. They all do. Once you find a sissy, you either become one or fuck one. And judging from your name, you're not looking to get with this hot piece of ass ;)"

"Well, I don't know. Maybe if you send me a pic I'd change my mind. But yeah, you were right. I went out and got myself some panties and a dildo, and tried it out. I didn't think much of it at the time, but now I can't seem to get being a girl out of my head."

"So are you trying to get out of the sissy life, or are you looking for some pointers on what to do next?"

I didn't even hesitate, "the latter."

I couldn't almost see her smile through the screen, "Amazing girl! If you've already got the panties and a dildo, most gurls try some of the following next: upping their toy game - you could try a butt plug or two; shaving their bodies - I highly recommend this, it feels soooo sexy; and makeup and a wig, to really complete the look. Go out and be girly!"

The list didn't surprise me. I had had fleeting thoughts of buying most of the items on it already. I had more questions: "Are there shops that cater to people like you and me?"

"Of course! They're all online - here, I can send you a link." I waited for a second before a link to a website called, somewhat unimaginatively, sissylover. She also sent me a link to an Etsy page for affordable wigs that she liked. I was appreciative of that. The only wigs I saw in Dirty Jo Punstore's adult shop were either rainbow-colored or bright pink, and I think I wanted a more natural look.

I started making myself a list. I wanted to be reasonable, like I was last time. I couldn't go and drop $100 every time I got super horny. But I could afford to shop a little. My bank account certainly wasn't lean by any stretch of the imagination. A woman's razor I could just buy at Walmart. I think I wanted to get a wig - long, natural-looking hair was a big turn-on for me, so I figure it would make the image in the mirror a bit hotter. And if I was doing the wig, I might as well try my hand at makeup. Sissylover had some fairly cheap basic sets I could buy.

"Jennifer, do you know any good makeup tutorials I could watch? I wouldn't mind a more feminine face."

"Girl, you have no idea how key that is. So many girls get all dressed up, then take one look in the mirror and just see a man dressed like a girl, and they get discouraged. I'll send you some good ones."

As I waited for her to send me the links, I kept scrolling through sissylover. First, I visited the lingerie page. I didn't really plan on buying things, but I didn't mind looking at the pictures of models. But one set did catch my eye: it was incredibly lacy and pale pink. It was a set of bra, panties, garter belt, stockings, and straps. The panties had two little black bows on them. I added it to my cart, thinking it would be nice to have a set that didn't need the schoolgirl outfit.

I next looked at the breast forms section. I thought these would be all expensive, but to my surprise, they were actually reasonably priced. I added a set of b-cups to my cart, thinking it would be nice to have something to fill my new bra. Looking at my total, I thought it would be a good time to stop. Apparently, I was wrong, according to my penis.

Before long, I had added a pair of low pink heels, a small metal butt plug with a pink jewel heart, and some cum-like lube to my cart. I tried not to look at my new total as I checked out. I knew this purchase was imprudent, but I never considered not buying the items as soon as they were in my cart. I wanted them all.

I knew it would take a few days, but there was one step I could do now - shaving. A quick trip to Walmart later, and I had my razor and a waxing kit, if I ever wanted an even smoother finish. As nobody was home, I immediately hopped into the shower. I didn't anticipate it taking as long as it did. The hair on my legs was thick, and shaving my balls took a very delicate touch. The hair on my chest presented a different problem - it was so sparse, it was hard to get the razor to pick it up. I did find that a woman's razor was much easier to use than a man's. Even though I regularly used an electric razor, and thus didn't have much practice shaving, I didn't cut myself at all.

After I finished my first leg, I couldn't believe the difference it made. My legs had gone from ugly and awful to feminine and perfect. I couldn't stop rubbing myself up and down, just marveling at my soft skin. Shaving around my cock had a similar effect. Even though my cock "stood out" more without the hairy bush around it, it still somehow looked more submissive, and feminine. I loved it. It was only after I finished that I realized I would have to be careful about how much skin I showed in public. But it was only a momentary pause. It was winter, and I had never been a big swimmer. I could keep covered up when out in public.

Soon, I was in my room masturbating with my new smooth body. Afterward, I felt that familiar pang of regret, but the damage had been done. I shrugged my shoulders, and figured I wouldn't have to deal with reconciling my behavior until the sissylover package showed up. And that's kind of how it went for me for a while.

I would get really into sissies for a few days, do something drastic, and then back off for the rest of the week. I managed to back off this first time until the sissylover package showed up. After having fun with the lube, and getting more girly than ever (even if I gave up quickly after my first disastrous makeup attempt), I came, and the next morning, I felt deflated and had to back off the lifestyle again for a few days.

I kept going to the gym, just to continue doing cardio. I secretly hoped to see pink leggings girl again as well, but she was awol. I had to settle for other girls in tight clothes as I jogged my weight down. Eventually, I started to only go every other day. I told Jordan that I just didn't want to get up early every day. The truth was that on the days I wasn't at the gym, I was doing pink leggings girl's butt workout in my room with a set of dumbbells I bought. I convinced myself it wasn't because I was a sissy. I was just doing the first workout regime that I felt motivated enough to commit to. It was healthy for me. It had nothing to do with my unhealthy obsession.

But in reality, of course it did. If I bothered to look back and have a modicum of self-reflection, I could see how much of my life had become about being a sissy. I was eating healthier because I wanted to lose weight. I had started to put on lotion every day for better skin. I wore panties more often than boxers. I shaved regularly. I had practiced deepthroating, and could now get my dildo to sit in my throat without choking. I wore a butt plug fairly regularly, just to feel naughty during the day. I was obsessed, even if I looked pretty normal on the outside most of the day most of the time.

I was also learning more about my sexual turn-ons during this period of explore and retract. Before this all started, I knew a few things about myself. I knew what type of girls I liked - typically I preferred skinnier girls to curvy ones, I liked long hair, and I was more of an ass guy than a boob guy. And I knew I loved to mix adrenaline with sex. That was it.

Being more or less a virgin, I didn't really know what my turn-ons were. Due to my religious beliefs, I had tried to keep in chaste with my highschool girlfriend. The closest I had ever got was on my 18th birthday, I had slipped inside her for a bit during a heavy make-out session. Guilt had me out of her and dressed before I could orgasm, unfortunately. But that wasn't enough to tell me what really turned me on. All that had taught me was that sex with a real person was pretty exciting.

One thing I had figured out was that I was a submissive. I had learned that even before the sissy obsession started. My attraction to pegging was a bit of a dead give-away. What I didn't know was why I was submissive. Now, I think I did. See, what really got me going, what really made the whole experience for me, was feeling sexy.

That may sound dumb or obvious, but it was a breakthrough for me. I had never considered myself particularly attractive. Historically, I didn't spend time working on my body, I never properly developed a sense of fashion, and I prioritized comfort over looking good. If people liked me, it was for my wit, charm, and easy-going sensibilities. In other words, it was for my personality.

The best thing you could say about my physical appearance was that it was unoffensive. I wasn't too fat, and I wasn't too ugly. I was plain. I had imperfections - my nose a bit too long, my chin and jaw a bit too weak, my shoulders a bit too slim, etc. But I never wowed anyone with my looks. I was found of telling people that I didn't make good first impressions or bad first impressions - I made no first impression. I thought I was ok feeling that way about myself. I was wrong.

Being a sissy was about becoming a sex object. It was about turning yourself into a vehicle for pleasure. Shaved legs, clean asshole, makeup, slimmer body, slutty clothes, all of those things were about making somebody turn their head and notice me, physically, and think, "Man, I'd like to bang her." And that's what I loved about it. I couldn't get enough of that feeling. So it wasn't all that surprising the night I finally found myself seeking an audience.