Certain Ch. 01

Certain Ch.1

Foreword

Hi all,

This is a story about me losing my virginity, but only the start of a story about my journey to self-discovery and self-actualization as a crossdressing sissy. As such, every event described here is at least 90% rooted in truth. Of course, to make for a hotter story for Literotica, some creative licenses have been taken. Additionally, names/facts have been omitted for privacy reasons. I hope those who read it find it a pleasurable experience, and I welcome all feedback and comments!

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My path to sissyhood was one I've never read about. I didn't try on my mother or sister's lingerie out of curiosity. I was not a straight man until I was seduced or hypnotized by cock. I was also not teased relentlessly for being unmanly before falling into the rabbit hole.

Instead, I grew up in a devout Catholic Asian family. I realized before my teen years that I was attracted to men, but I never really acted on those urges. My religious upbringing, fear of being outed, and just my general lack of strong sexual desire more or less stopped me from doing more. Catholic school isn't brainwashing and not all their lessons sunk in, including the bit about the sins of masturbation. I didn't have a high sex drive, but even when I did, I easily took care of the issue with a bit of internet exploration, where I satisfied myself with videos of big, muscular men taking out their sexuality on skinny, powerless boys.

I was 5'6", 140 pounds soaking wet, and thin. I played sports that avoided physical contact like track. When possible, I avoided sports entirely. My thin face and soft features completed the look. Partially due to genetics and partially due to diet and exercise, I increasingly felt more like the overpowered bottoms in the porn I watched, and my quiet personality warped around it to make me an ideal bottom twink.

But, by the time I graduated high school, my only brush with gay sex had been an awkward session of frotting and "just the tip" oral with an acquaintance at a sleepover that neither of us spoke of again. I remained closeted, attending prom with a girl and doing things guys my age were supposed to do, but I knew better than ever that I wanted to experience sex on my terms.

This all changed in the COVID years. I had been accepted to a university on the East Coast in a much larger city than what I grew up in, not to mention among students with a lot more experience and openness about sex. My newfound freedom and the anonymity a larger pool of potential partners excited me. I was ready to truly live life and know pleasure as any person deserves.

I had slowly fallen down the transgender porn rabbit hole over the years, and had slowly began to see myself in the girls on screen. One particular porn channel, BecomingFemme, soon attracted my attention. It's male star, ChristianXXX, looked a lot like authority figures of my childhood, and I yearned to be like the sissy girls taking his hard cock. When COVID hit and many students left campus housing, I began to experiment, first buying a pair of yoga pants to accentuate my ass, then a little black dress to feel sexy in. By the second month I had escalated to a wig, lingerie, and stockings. I also began fingering myself a little and soon my masturbation sessions were incomplete without at least a finger up my inexperienced hole. Each time I cum, I would go through a cycle of purging where I feared I would be outed and judged for all the perverted experience i've had. But after a while, I would come crawling back to my feminine urge.

I started posting pictures of myself in various outfits on Fetlife, fishing for affirmation and attention. I knew I wasn't looking for love, but instead looking for a very specific type of affirmation - I wanted a man to message me, flirt with me, and then fuck me. Fortunately, I did not have to look far.

As a beginner crossdresser, I hadn't really practiced all the necessities of femininity like makeup and hair removal. I wasn't sure how to attract men, so I started showing off my body in various suggestive poses. A few months in, I received a message from an older gentleman who offered, essentially, to transform me into "a beautiful girl". Browsing his profile, I saw that he had a treasure trove of outfits, wigs, heels, and other accessories on hand, and that he had experience - in every image he was penetrating and taking another sissy. Other girls like me.

First, I was afraid. This was a strange man on the internet, a creep for all I knew, and I was afraid that meeting him would expose my shameful secret or worse. But as I browsed the profiles of his friends and of him, I understood that this guy was legit. An experienced admirer of sissies and crossdressers. And he wanted to meet me, dress me up, and who knows what else! This was my chance to meet my very own ChristianXXX, fulfill my sexual dreams, and maybe gain a little fame and notoriety in my own right.

My responses was, in hindsight, a bit much. I thanked him profusely for noticing me and practically begged him to take my virginity. But his positive response soon soothed my nerves. I told him about my inexperience, my need for guidance, and my excitement at his offer. He stopped short of promising he'd fuck me, but assured me he'd doll me up and make me feel as sexy as can be. I became far more trusting, sending him a sexy shoot of some newly acquired lingerie, not even taking the effort to hide my face. After all, he was going to see it anyway when he fucked me, I hoped.

After some flirtatious poking and prodding, we set a date in a week's time. I thought it would give me time to prepare, mentally and physically. Over the years I had learned all the steps to prepare for an anal fucking - the douching, the preparing with dildos, yada yada. Afraid to order the toys online, I rushed to a local sex shop and bought myself a small-ish dildo, a douche, lube, and a bejeweled butt plug. For a desperate and closeted sissy, I really was underprepared.

For the next few days I prepped myself. I shaved the little body hair I had. I read articles that taught me to take the lead, start by riding him, use plenty of lube, douche properly, everything to make my first experience a good time. But when I came to actually physically preparing, I realized I was afraid. My inexperience and understanding of sex through the lens of porn meant I didn't really get anal penetration. While I could douche just fine, even finger myself a bit, when it came to actually fucking myself with a dildo, I could never push the tip in. Something was keeping me from mustering the strength to properly penetrate myself with anything that big, no matter how hard I tried. When the day finally came, I realized that I had no experience actually taking cock. But I didn't want to back out. The morning I was supposed to meet him, I put on my panties, garters, and a new pair of fishnet stockings. I looked at myself in my full-body mirror. The fishnets accentuated my legs, while the matching lacy bra and panties covered my clitty and gave the impression of me having some small breasts. Feeling my breath quicken, I packed a bag of some necessities, lubed and inserted my thin plug, and headed out to meet my taker.

He met me at a bus stop and introduced himself. While I was not fully dressed, I put on my best feminine voice and let him guide me to his waiting car. I knew I was nervous and jittery, and that probably made me seem more quiet and submissive, which actually was a plus. On the way we chatted, he asked about my studies, my background, all comfortable topics that further put me at ease. We soon arrived at his house, where he let me in and offered me a drink. Then, he led me to a walk-in closet, where he offered me the chance to dress and pick an outfit from his collection. Doing my best to act sultry and submissive, I offered with a wink, "Dress me, I'm all yours."

A few minutes later, I admired myself in the mirror. He had given me a black lace top, lacey gloves, and a a pair of stripper heels. I also wore a little skirt around my waist and a masque to hide my eyes. The wig's flowing locks of dark brown hair framed my face perfectly, like a real woman's would. True to his promise, I felt sexy, like I had fulfilled a lifelong destiny, and was finally seeing who I could be. But that was not all. He took me to a different room with carpeted floors and a comfortable bed, a massive mirror as the headboard, and another mirror on the side, offering its occupants a full view of whatever debauchery occurred in it. I also saw the condom and lube on the nightstand. Here, he took me one step further, putting me in sexy poses and taking pictures to "remember the occasion." He also put on a sissy hypno video, which turned me on to no end. The girls in the video were being dominated, used, and were loving every moment of it. My mind swirled with what would soon become of me.

The alcohol had begun to kick in, and I found myself feeling braver. Remembering the internet advice to take charge and guide the process, I knelt down on the floor before him as he was setting up the next shot. He immediately understood, and pulled down his pants. It was only now that I got a good look at his cock: around six to seven inches, and thick. Bigger than the dildo I couldn't take. Still, I took him into my mouth and felt him stiffen. I'd never felt another man's arousal so close or smelled the musk so clearly. I was getting ready for my deflowering.

I sucked his cock diligently, sloppily, and a little unsteadily. First, I was careful, taking in the tip, the head, and licking him like a lollipop. But my body burned for more, and before I knew it, I was trying my best to take as much as I can into my mouth. He soon sat down on the bed and allowed me to slobber all over his crotch, apparently enjoying my very first proper blowjob. I tasted on my tongue his salty precum, felt his tip reach the back of my throat, and instantly gagged. I pulled back slightly, expecting a break. Instead, he grabbed the back of my head, and began gently thrusting into my mouth.

I was almost a little horrified. I held onto his thighs and braced myself, trying to anticipate his thrusts. I felt a muffled voice cry out within me. But each time he hit the back of my throat, I gagged and gasped. But I tried my best to soldier on. I could hear him moaning with pleasure, and I felt my own clitty stir. Deep down I always knew that my mouth was for pleasuring cock. I had come here dressed in fishnets and garters and plugged because I wanted to get fucked. I put on a wig and a bra because I wanted to be fucked like a woman. So my eyes watered and I retched a little, but I carried on. This was the hottest thing I had ever had happen to me up until that point in my life.

After God knows how long, he slowed his assault on my face. Spit trailed from my mouth to his beautiful cock as I pulled up, coughing and gasping. I felt used, sexy, humiliated, fulfilled, all at once. I looked up at him. He hadn't cum. He was saving that for later.

"Do you want to get on the bed?"

It was phrased like it was an actual question, but he was holding my hand and slowly guiding me to the bed already. At that point we both knew I was willing. Anyone who tolerated and even slightly enjoyed that face-fucking was ready for whatever came next. I enthusiastically got up on the bed on all fours. Face down, ass up, just as I had seen in the videos, in the hypno, and in my imagination a million times before then. I was about to be deflowered.

He sat next to me, admiring my ass, complimenting my shape and submission. It mattered little to me, but it's the thought that counts. I had had enough of the admiration and flowery words. I wanted him to prove to me exactly how sexy he thought I was. He slapped my ass playfully, and I wiggled teasingly. He tugged my panties aside and pulled on my plug, which gave way with little resistance, popping out to reveal my unguarded, virgin hole. He kissed it. I instantly puckered up. Whether because it was an unexpected if not unpleasant sensation or because he had a beard that tickled, I'm not sure. He then planted his face in my cheeks and began rimming my hole.

I could feel my whole body lurch towards him, eager to let him continue his oral invasion, inviting him to do more, faster, stronger, rougher. My back arched to take advantage of his loving kisses. But he held me in place, tasting me carefully and inviting my moans and gasps. I felt his talented tongue circling my rim, testing my boundaries by probing a little further every now and then. Between licks he mumbled curses and praise. I made out few words, but I was in heaven and no amount of Catholic teaching could convince me otherwise.

But he soon pulled away, leaving my hole winking for him. From the nightstand he grabbed the lube, and began generously lubing my entrance. It was gentle, cool, and a little numbing. He started to probe me with his fingers, not just for my willingness but my cleanliness and my readiness. The new, rougher invasion of my hole began. I gripped the sheets. A finger or two didn't exactly bring me pleasure or pain, but I knew what came next. He slowly worked up to three fingers, which hurt a little but stretched me out. Before long, his finger-fucking stopped and he withdrew. I inhaled sharply as i felt my hole relax and tighten.

He stood up on the bed. I braced physically and mentally. I could hear him stroke himself, pouring lube as he went. I also knew the condom was still on the nightstand. I didn't ask him to use a condom, but I knew from all the articles I read that it was a must. I had to ask him to put it on, or better yet, put it on for him in a gesture of caution and submission. Yet I didn't move. I wanted him to take me raw, I wanted to feel the texture and power of his cock as it pushed into me, and I wanted, above all, to feel him finish inside me, conquering me with his seed and wiping away my purity once and for all.

As he lined up his cock to my entrance and began to push, I instantly regretted everything. It hurt! Every decision I made leading up to this began swimming through my mind. What would my friends and family say, seeing me here, dressed as a sissy, face down, ass up, with the throbbing ready cock if an older man penetrating my virgin hole? Was it worth it? Why didn't I start by riding him, like those blogs told me to, so I could control his push? I didn't know it in the moment, but my whole body had tensed up like never before, and as he started pushing harder, began to emit a groan. A strained, almost guttural sound of pain. He stopped pushing.

"Are you ok? Need a minute?" He asked. I turned my head to say yes, catching a glimpse of myself in the bedside mirror. My face was flushed, in fact, my whole body was. My knuckles were practically white as they gripped the sheets. But my legs were spread open, inviting, ready, and he towered over me, physically demanding my submission. His thick cock rested between my cheeks, peeking out above like a periscope, gauging my reaction. I saw in that moment that I was a sexual being, one who had been deprived for too long out of fear and lack of respect for my own desires. As if by reflex, I took a deep breath and relaxed. Then I started to push back against him.

He needed little encouragement after that. I felt his tip push through my opening, stretching me out more than I've ever been. Every inch that pushed into me was painful as he took me, slowly, self-assuredly, stretching me out to accommodate him. I let out an involuntary moan, not because it was particularly pleasurable, but because I was a submissive, submitting to him. "Good girl," he whispered in my ear. It made my whole body shudder.

He started pulling back out. It hurt every inch of the way, but as he pushed back in, it hurt a little less. I loosened my grip on the sheets and stretched out before myself. I could feel his grip on my hips tighten as he rocked slowly back and forth in my tight passage. I felt his body heat inside me, his cock stirring my insides in a way I will never forget. As he slowly rocked on and out, I began to warm up to him. My pain subsided. I moaned again, this time in pleasure. I found myself pushing back against him, begging for more.

As if hearing my muffled moans, he slowly began fucking me. What started as a gentle rocking became a steady pistoning, transitioning to a rabid assault on my newly deflowered hole. I could hear my involuntary cries of "oh!" each time he's hips met my ass and he sunk his sword into my willing sheath. The room was filled with the sounds of my moans and of a rapid slapping, first of him slamming into me from behind, then of him leaving red palm prints on my ass to remind me of the place. Each time he thrust into me, I threw my ass back, eager to feel him take his sexuality out on me. I moaned loudly, maybe unwomanly, but I didn't care. I was finally being fucked. An unfamiliar pressure was building in my loins, and I knew instinctively that it was a result of the fucking I was receiving. I had lost my virginity to a man nearly three times my age, who was now fucking my ass in doggy style. Not a romantic, slow lovemaking in missionary that I had dreamed of in my yourh, but an anonymous, hookup style doggy fucking that degraded my existence to a piece of meat, being used for his pleasure. And it drove me wild out of my mind.

Soon his pace slowed, and he pulled out without coming back in. Thinking he might be taking a break, I turned over onto my side and met his eyes. It was filled with lust for my body. I knew he was not finished. I was now on my back with my legs spread, staring up at him in like a doe in headlights. He stood over me, practically covered me with his body, and pushed back in. I yelped loudly as he sucked at my neck, forcing my legs open as he threw his body weight into dominating my helpless body. I pulled my legs aside, giving him free rein into my hole. This position felt different. It still hurt getting pounded with such force, but it felt like there was a string being pulled taut inside me, building up pressure, ready to snap. "Please don't stop, daddy." I could hear a voice beg, one that I barely recognized. "Please fuck me harder, oh God, I need it, please don't stop daddy!" It sounded like a corny porno, but the voice sounded so earnest, so desperate. He grunted as he met my enthusiasm with renewed force. I could not help but begin playing with my own, practically limp clitty as the tension built up inside me.

I exploded, one hand on my clitty, the other raised above me, grabbing whatever leverage I could get from the sheets. My back arched up, my mouth open in a silent scream of ecstasy. My mind was full of static, as if it had just lost its signal from reality, and my hearted was about ready to leap right out of my chest. I had cum, forcefully, beautifully, all over my hand and on the clothes my deflowerer had so generously loaned me.

With that, I came crashing back down to Earth. Post-nut clarity hit like a truck, and I was immediately aware of the situation I was in. I was fucking, no, being fucked, by a much older man who still had more stamina. In fact, he slowed only briefly to scoop up a bit of my cum with his finger, then fed it to me like I was a baby bird. I latched on, surprising myself, suckling on his finger and tasting the sweet and earthy fluid. Then he picked up the pace again. I hardly knew what to do except that I was no longer taking any pleasure. I was just being penetrated, my ass expanding repeatedly to accommodate his cock.

I looked up at him, bewildered. His chest rose and fell with his thrusts. He stared back at me, and I knew he understood. I was not necessarily into it anymore. Every man knows post-nut clarity, and knows the disgust that could accompany a particularly shameful session. He held my gaze with a steely stare, slowly pulling out of my ass. But, instead of moving off me, he continued to hold me down, and kept his cock right at my entrance. He wanted more, and was waiting to see if I'd blink first.