Sissification 101: Ch. 01

Summary: Straight guy is caught watching sissy porn and...

Note 1: Thanks to Eric who requested and helped plot this lengthy story.

Note 2: Thanks to Tex Beethoven and Robert for editing.

Note 3: All characters are at least 18 years old.

Sissification 101: Ch. 01

1. MY SISSY CURIOSITY

I've always liked nylons. I grew up when they were still popular and worn by many teachers (unlike now), plus by most cheerleaders, and some of the nerdy girls... it wasn't as great as the wild fashion of the eighties, but still better than the bare-legs laziness to date so far in the 21^st Century.

I loved looking at women's legs in nylons, especially if they had a sheer shine to them.

I was drawn even more to nylon-clad feet. If a girl was sitting at a desk within my view, I'd just stare at her feet, praying for her to slip her feet out of her shoes. Although I loved seeing legs in nylons, I liked seeing feet in nylons even better. I couldn't explain it then, I can't explain it now. Just the sight of someone's feet and toes in nylons, regardless of the woman's age, and I get hard. (Yes, that's still true today.) If I see a teenager's feet in nylons, I instantly get erect. If I see my girlfriend's feet in nylons, I instantly want to fuck her. If I see a grandma's feet in nylons, I still get turned on. The truth is pretty simple... nylons, and especially nylon-clad feet, are my sexual kryptonite.

They always have been.

Back when I was in school and I saw a teacher or another student in pantyhose, I'd daydream about rubbing my hands on their legs, or about having them rubbing their feet on my cock. Sometimes, but only in private of course, I even wore them myself.

Truth was, occasionally I even wished I was a girl. Being a guy, I was automatically disqualified from wearing pantyhose, or any other variety of nylon hosiery... at least so anyone could tell... which I thought was very unfair.

As I got older, I pushed these fantasies out of my head. The 2000s arrived, and somehow we dodged the bullet of the massive Y2K electronic meltdown everyone had predicted, but the new century did seem to eliminate silk hosiery as a fashionable accessory.

Spying a woman wearing hosiery became rare, and seeing a woman's feet in hosiery became almost as rare as stumbling across a needle in a haystack (although far less painful).

Thankfully, what the 2000s did herald was porn going mainstream, and throughout my twenties although I dated a few girls, some of them semi-seriously, and one I even thought for a while I might marry, I spent way too much time online.

Doing what online?

Watching porn.

Watching lots of porn.

Online, I could be anonymous.

Online, I could find women wearing nylons.

Online, I discovered I wasn't alone in my nylon fetish.

Online, I found there were fetish websites for pretty much every possible kink... many I hadn't even known existed.

But thankfully, there were many people like me, perhaps not in percentages but certainly in numbers, and therefore many websites that catered to people like me with a nylon fetish.

I've also always been an avid reader. I hid a couple adult sex books in my room as a teenager, had a couple dozen on hand during college, but once the internet exploded, I could read story after story online and not need to worry about someone finding my stash under my mattress. One of my favourite online authors was silkstockingslover, aka Jasmine Walker, a female writer who not only had an unabashed fetish for wearing nylons, but also for seeing other people wearing nylons, and best, who also wrote stories in a variety of categories that turned me on. Because almost all of them featured characters who were wearing nylons, and who made a big deal about doing so.

But I didn't always read porn, frequently I watched it instead. At first, I watched M/F porn and F/F porn, always searching out scenes where the girl was in pantyhose, or thigh highs, or stockings and a garter... and best, scenes where the heels were eventually slipped off.

Yet I also flew through silkstockingslover's extensive collection, or at least the straight, lesbian and incest stories. (I would never do incest, and I was physically incapable of doing lesbian, but they were still kinky to read about.) Eventually I'd read them all... most of them more than a couple of times.

Yet then, I don't know why, other than I just loved the her writing and her captivating characters, and occasionally her clever repartee between characters, plus there being the odd gay-like scene or story (gay themes but not really, such as pegging, cross-dressing, and even guys sucking or being reamed by cocks still without quite being gay, go figure), which made me curious about wearing pantyhose for real. I'd resisted the temptation my entire life because it wasn't considered manly, it seemed to be a gender issue, or maybe a gender identity issue, but suddenly I was discovering there was a whole subculture where men not only wore nylons, but sometimes dressed entirely as women (and wore women's makeup or not, depending).

I read one that triggered me completely, and started me on this wild journey of exploring my sexuality, "Curiosity Fucked the Straight Guy". After that, I read every quasi-gay story she wrote, almost all of them about straight white or Asian guys (I'm Asian) who ended up succumbing to their sudden (or perhaps eventual, but in either case) irresistible fascination with black cock.

Here are a few pornographic themes that appealed to me the most. And in retrospect, I can now see which also influenced me the most.

a. White men submitting to black men.

This was a theme that fascinated me, as I'd always felt myself inferior to black men, and I wanted to know whether that was really the case. It was certainly possible. They were all built stronger than me (with or without serious exercise), and they all had massive cocks... all of them so much bigger than mine. Or at least so I thought, and for some reason felt the need to find out.

I was 1¼ inches soft, and 4½ inches hard. According to my non-scientific research so far, black cocks were almost without fail, double my size, or even more. And whether that was generally the case or not, according to everything I'd seen in porn, that was always the case.

I was so envious of those big black cocks.

So jealous of those big black cocks.

So in awe of how fascinated and lustful the girls got when they saw their first big black cock. The screams they made as that big black cock slid inside them. Their nasty talk and begging as they were fucked by that big black cock; and that wasn't just their first time, that was every time.

No girl had ever done any of those things for me!

I didn't immediately begin to wonder what it would be like to suck a big black cock... no, that never occurred to me at the time... but the seed had been planted in my subconscious, and it would slowly grow inside me, without my knowledge or consent.

b. Married men being pegged.

I wasn't sure whether I ever wanted to get ass fucked... but my curiosity had been awakened by the vivid descriptions in some of silkstockingslover's stories.

I wondered what it would be like to be the girl.

Bent over and fucked.

Dominated by a woman.

I'd always felt inadequate because of my dick size, I assumed women often faked it with me, and pegging was a new kink that had me questioning my sexuality.

c. Crossdressing

Jasmine only had a couple stories featuring crossdressing, but the way she wrote them seemed so liberating... both for me and the characters in the stories.

It led me to go to the mall.

It led me finally, after all these years, to buy a few pairs of sheer pantyhose.

It led me to finally summon up the courage to put a pair on.

I wasn't yet intrigued by the idea of dressing completely as a woman... but again, unbeknownst to me, that seed too was planted in my head and began taking root.

I wasn't bold enough to wear my brave new acquisitions outside, or to work... but the moment I got home, I peeled out of my suit and climbed into a pair of sheer hosiery... which I experimented with during the next number of days... concluding that I usually preferred wearing them without underwear... and I loved slowly rubbing my legs and my cock in the sheer nylons, and I always ended up rubbing myself to orgasm after a few videos and a few stories and coming in my pantyhose.

D. THEN I READ A SISSY HYPNOSIS STORY.

Even after years and countless hours of watching porn online, I had no idea sissy hypnosis was a thing.

Then even after reading Jasmine's vivid, detailed, HypnoSissy series, I still didn't know it was a real thing.

Of course I then googled it... and found on Pornhub that not only was it a thing... it was an entire sub-culture.

There were hypno-sissy videos.

There were hypno-sissy audios.

There were hypno-sissy websites and Mistresses.

There were hypno-sissy captions where actual women portrayed themselves as cross-dressed men.

It was all so surreal.

So captivating.

I'd finally found a place where I belonged.

Sure, it was just the internet... but it was mine. Just like how some shy or insecure or nerdish kids who get bullied at school can feel all mighty and powerful online by playing something like Street Fighter... I felt I could be myself online.

I entered chatrooms and took part.

I watched every hypno-sissy video I could find.

I took to heart hundreds. if not thousands, of sissy captions... all while wearing pantyhose.

I developed, without my realizing it was happening, a massive submissive mentality, as I (now consciously) began fostering an increasingly undeniable desire to be transformed into a sissy slut... for real... to suck a big black cock... for real... to be caged by a strong female personality... for real... to be pegged... to be spit-roasted by big black cocks... to be cuckolded by a woman I loved as she got herself fucked by big black dicks and made me eat her creampies... to be completely sissified... to be coated in cum... to be the center of an orgy and dominated by big dicked black men... all not as online fantasies, but absolutely, factually, for real.

This, of course, was all just fantasy and gave me great orgasms... but I never imagined it would ever be anything more than just fantasy....

Then... over the course of a crazy year... everything listed above came true... once I met Joan.

Joan was, no she is, an amazing woman.

They say opposites attract, and that theory was proven true when we started dating.

She's vivacious; I'm shy.

She's white; I'm Asian.

She's 5'7", which is fairly tall for a woman; I'm 5'5", which is fairly short for a man.

She has big, hypnotic, blue eyes that draw you in; I have bland, undistinctive, brown eyes that are as unnoticeable as they come.

She has lovely, wavy, brown hair that seems to adapt and change colour to best enhance her accessories; I have dull, straight, black hair just like every other Asian (except for the gorgeous ones).

She's athletic and works out every day; my idea of a good workout is masturbating.

She has an amazing slender body; I'm slightly chubby.

She's very pretty, with a few attractive freckles under her eyes, and high cheekbones; me? Well, I'm literally non-descript, with no particular features to set me apart from any other mid-30s Asian guy.

She has a sexy smile; I can't smile without looking a little creepy.

She's confident in who she is, while I'm completely insecure.

It was obvious she was way out of my league and yet, after some coaxing from my coworkers, I asked her out, and she astounded me by accepting.

What we had in common, just looking at the surface for now, was we were both geeky, both passionate about our work, both loved cooking and fine dining, and both were (and still are) very thoughtful, pragmatic people.

Less obvious at first, we also had one more thing in common... we both loved nylons. She wore them to work every day, and on most of our dates when we first started dating, and on all of our dates once I confessed to I having a thing for them. She even wore thigh highs, or a garter-belt and stockings, whenever she came over for sex, or I went to her house for sex.

So, although at first I didn't think I had a chance with such a beautiful woman... we really hit it off, largely because we both loved trying new restaurants, and thus I began living a dual life.

One side of me was: a caring, compassionate, attentive boyfriend with an amazing girlfriend who liked giving head, loved swallowing cum, had an insatiable sexual appetite, and seemed okay with my small dick... although I compensated for that by going down on her even more than she went down on me. I had learned early on that the best way to keep a woman was to treat her well, to respect her, to listen to her carefully and caringly, and frequently to get her off with my tongue better than any man or woman ever had, prior to me.

The other side of me was a pantyhose-wearing sissy whenever I was alone at home. I also watched hypno sissy videos for at least a couple of hours each night. I parroted the degrading words of faceless women with seductive voices, thus degrading myself. I frequently watched BBC porn, focusing more on the big black cock than on the hot woman taking it in any of her three holes. The minute I got home, I cast aside my boring suit (well, that was a bit overdramatic; actually I hung it up neatly), thus exiting that part of my life, and put on pantyhose and nothing else for the rest of the night, as I entered my other life.

This kinky pattern of behaviour became the trigger that changed everything... in a single moment of time. One moment of sexual serendipity... if you believe in that sort of thing... I believed prior to this crazy night, and what happened next, confirmed my belief).

2. CAUGHT YOU IN THE ACT

MONDAY

I was in my home office, in my high end gaming chair (when you spend as much time in a chair as I do, it's well worth the money), watching my favourite BBC hypno-sissy video on my computer screen (24 inches, lol), where every few seconds, a different big black cock was fucking a different mouth, pussy or ass, while the most seductive female voice I'd ever heard constantly ordered me to repeat after her a wide variety of derogatory, submissive, and racially fueled descriptions of myself.

So, I was naked except for my expensive pantyhose (I'd ordered a dozen pairs of luxurious sandalfoot sheer silk pantyhose from Europe six months prior, and had eight pairs still in great shape), slowly rubbing my raging four-and-a-half-inch cock (if a cock as small as mine can be said to rage), parroting in a loud voice saying, "I'm a sissy begging for big black cock and a load of dominant cum," when I suddenly froze, realizing I wasn't alone.

"Oh my," Joan said, her tone sounding as shocked as I instantly felt.

My eyes went wide; I was paralyzed from getting caught in such an act... by my girlfriend!

The female voice on the screen, blithely unaware of what was transpiring in real life, ordered, "Repeat after me. I was born to be a sissy two-hole faggot for every big black cock."

I didn't repeat that one, even though habit made me sorely want to, the idea of being a two-hole slut having become more and more intriguing as time went by, but instead I slowly turned around to see her behind me, standing just inside my office doorway, staring at the screen.

She asked, with no qualities in her voice to give away whether she was shocked, disgusted, stunned, or something else, "So tell me Eric, were you really born to be a sissy two-hole faggot for every big black cock?"

I apologized, terrified of losing the woman I believed I was meant to be with for life, "I'm so sorry Joan, this isn't what it looks like."

"It appears to me that you're watching, as well as participating in, black cock training sissy hypnosis videos," she said, as the video behind me continued to play. "If you can give me another description that makes any sense, I'll be happy to hear it."

The female voice ordered, a sentence I had long ago memorized, actually I'd memorized the entire twenty-two minute clip, having already watched it hundreds, perhaps even a thousand times, "Declare to the world that your purpose in life is to be on your white pathetic knees, worshiping the superior black race."

I frantically spun back around and halted the video, my cheeks burning with shame, having declared that statement almost every night at least a dozen times for over a year.

"Nice pantyhose," she said, although her tone continued to conceal whether she was delivering a compliment or sarcasm.

Caught in the act, I had completely forgotten I was wearing nothing but black pantyhose... compounding my humiliation.

I stammered another apology, "I-I-I'm so sorry."

"How long have you wanted to suck black dick?" she asked, ignoring my apology, and still giving me nary a clue as to what she was thinking.

On the bright side, she hadn't freaked out, thrown anything (both of my prior Asian girlfriends had literally thrown shit at me when they got mad), or stormed out in a fiery rage.

Yet she also hadn't moved a single inch from leaning against the door frame.

Her tone hadn't changed at all.

Her expression was stone cold. Which was how I first learned she had an amazing poker face.

I whispered, shame coursing through me, even though my tiny cock was still hard, "For a while."

"Since before you met me?" she asked.

"Yes," I admitted, which I didn't know was better or worse for me. Was it worse for me to have hidden it when we started dating, or for me to have discovered this twisted side of myself after we started dating? I sensed that the answer I'd just given was the better of the two, if only the lesser of two very humiliating evils.

"Have you ever really sucked a black cock?" she asked, making me a little overwhelmed to be answering such questions to the woman I'd fallen in love with. I'd never imagined this secret fantasy being revealed to anyone I knew in real life.

"No," I answered sheepishly, feeling my cheeks burning with shame.

"Have you ever sucked any cock?"

"No."

"Do you want to suck a black cock?"

I answered with the truest response I could; there was no point in lying now, "Sometimes I do."

"Sometimes?"

"Yes," I said, as I tried to find a way of explaining to her what even I didn't understand myself. Even after years of gradually becoming more and more intrigued by crossdressing, sissification, and especially fascination with black cock, I still had no idea what kept constantly drawing me into this growing obsession.

"So you're saying that sometimes you want to suck a black cock and sometimes you don't?"

I sighed and gave her my most simplistic answer to a surprisingly complex question, "Yes, I do when I'm horny."

"So you want to almost always," she summarized.

I wanted to counter her seemingly playful shot by pointing out that she was almost always horny too, but this didn't seem to be the best time to tell her that (and I sure as fuck would never complain about it. Truth was, I'd never had sex more frequently in my life than since I'd hooked up with her. She was truly insatiable).

She then asked the question I was dreading, the one where I'd see her insecurity peeking out from under cover, "So I'm not enough for you?"

This barb, (or rather reverse barb, since it was really directed at herself), made me feel even worse than getting caught in such a compromised and humiliating position. My obsession had nothing to do with her. In truth, I'd watched fewer sissy videos, been a little less obsessed with black cock, ever since we'd met... although the difference wasn't huge (as in I didn't spend eight hours over a weekend watching every sissy video ever made... usually just two or three hours). I said, "You're more than enough for me, it's just...."