A Story of My Confession

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A man recounts his life and how he was forced to dress.
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Lexavier
Lexavier
21 Followers

Dear Reader,

This story is unlike that which I've written before. There's a tiny sprinkle of my own life in here but the majority that you read is that of a fabulous friend with a kinky fantasy. Please enjoy. Everyone in this story is 18 or older. Beautifully edited by taz23girl who did an excellent job.

Lexavier

Part 1

I feel the need to justify myself, vindication pure and simple. A last plea for understanding before I... well, let's not jump too far ahead.

Who am I?

Maybe you can help me answer that question by the end of this. Unfortunately to fully understand, we have to start right at the beginning. I hope you can bear with me; the fun stuff will be happening soon. If you want to skip ahead, feel free, we'll see you again in part 2.

I can't really pick one defining moment of my life where I can say, "There. That's the moment everything started." My perception of sex shifted and changed, like a river carving its way down a mountain. How much of what I did was simply normal exploration... and how much was I lying to myself? I still don't know.

I think in College I was pretty normal. One thing to my advantage was that, at an average build, you could never accuse me of being fat. I wasn't ugly, but I wasn't handsome either. The girls would often call me cute. That didn't stop me being ridiculously shy around them though, which was probably why I had relationship after relationship that never lasted more than a week. I struggled to make the first move, and they got sick of waiting.

I was active online though, watching porn and chatting up the ladies in forums, even enjoying some sexy exploits, courtesy of the chat rooms in the various Yahoo online games, back in the day. I was always a keen writer, and I found it relatively easy to find eager partners... that didn't last though, more on that later.

Meanwhile, I began a real life relationship which would come to last. To protect her I've changed her name, let's call her Laura. Laura was a member of the orchestra, same as me. She wasn't drop dead gorgeous, even plain in some lights, but then there were moments when she took my breath away with how amazing she looked; the Spring Ball specifically comes to mind. Personality wise, she matched me through and through. She laughed, a lot, and she had a sharp mind... and she liked me. For the first time, I had found someone who actually took steps to help me overcome my shyness. Our first goodbye kiss was initiated by her wrapping her arms around me and pressing her lips to mine in a fleeting embrace that I'll never forget.

We were both virgins though, and neither of us had any experience with even the most basic stuff. It was a year before our first sexual experience and it didn't go very well. There was a lot of pain for her, even tears rolled down from her eyes. Not what you want, right? The next time was better, but not by much. In fact to this day, our sex could only be categorized as 'OK'. It seems like she won't even try, and I'm running out of ideas. We make love maybe once or twice a year, and it's always quick, leaving me crest fallen with a sense of frustration. That's when it actually works, a lot of the time during foreplay she stops me and she never initiates, she just lays there like she doesn't know what to do... can you tell that I'm bitter?

I guess it was during this period of frustration that I started to branch out on-line a little more, striving to discover new ways to self-pleasure so I didn't have this feeling of regret welling up inside. I loved her... I still love her. But I needed more. The first thing I did was get back into on-line role-playing and cyber-sex. I discovered a particular chat website where I set up an account. But this new and mature scene was harder and more demanding. I wasn't getting noticed, despite my improving writing skills.

I was also looking for other physical sensations as well. In the shower I explored my body, I even found my Mother's vibrator, a basic model that only had an on and off switch. I had read that, if a certain spot was massaged anally, it'd be the best orgasm a man could have. Perhaps I was doing it wrong, or the smooth plastic wasn't really designed for what I was using it for but I could never find that sweet spot.

So desperate was I for a blow job, (Laura would never give me one), that I even tried to bend or roll over. I could only ever manage to lick the very tip of my cock, tasting my pre-cum, and only with much discomfort. Not exactly what I was hoping for.

A while later I found Literotica, and later yet, the forums. The role-playing there was in a different class altogether, but once again I found it difficult to find willing partners. The website and the people on the forums inspired me to write my first erotic story. It was mediocre, but I poured my passion and heart into it and I was proud of it. The problem came with how to distribute it? If I posted it, would it be as ignored as I was?

Maybe you could say this was the beginning. Maybe when I created the female account, based on someone I had met on-line, that I was really projecting my deepest desire... or some psychology crap. I don't know. What I do know is that it worked. I got good reviews, good comments, and begs for more. For the first time I was receiving sexual acceptance. Believe me, it felt amazing.

So where to go from here? Writing on my own was hard work... so I used my new found account and moved across to the forums. A new world of literary adventure opened up to me, or should I say to Alice, my new Pseudonym. Alice had adventure, she flirted and made friends, and she fucked hard. For the briefest of moments, I was fulfilled, I was happy. I even wrote a second story, with the help of my new friends, and this one did even better. My physical sex life didn't seem so bad, now I had this amazing virtual one.

But the feeling ebbed slowly, and I was once again left with a cloying sense that I was missing something in my life. Role-playing grew stale and my on-line friends fell away, especially as I started University and my time on-line became shorter and shorter. I was still exploring other aspects of my sexuality. I started to poke through Laura's drawer, the one she had at mine and found a pair of her panties, soft silk and frilly cotton and lace that felt smooth and velvety when pressed against my aching cock. It was only a small transition between wrapping it around my member to actually wearing the garment. The thin material disappeared between my ass cheeks, pressing naughtily against my anus. I would always cum in moments, then feel guilty and ashamed as I ripped them off and put them back in her drawer where I found them, as neatly folded as I could.

Another jump came when she left her bra at mine. I wondered how it would feel, what it would look like. Sad as it sounds, I half hoped it'd make my chest look like real breasts so I could imagine touching them. Laura is fairly petite and relatively flat chested so her bra was tight around my body, but with a little help from a pair of socks, it didn't look half bad. Out came the panties again and when I tucked my cock between my legs, I almost looked feminine. I felt silly and ashamed. I left it there for a bit, thinking I had passed that stage of exploration. Why would I need to dress up again?

It wasn't until my Brother came to stay with his wife that I did it again. All alone in the house, I found my Sister-in-law's opaque tights. They made my legs wonderfully smooth and the dark colour hid my leg hair. Out came the panties and bra again, and with some skimpy pajamas, I felt like quite a hot piece of ass. How to prove it though? There was no-way I'd ever let anyone see me like this.

It was a random chat webcam website that allowed me to show off my body while keeping my face hidden. The compliments I got sent shivers through my body. Many of them thought I was a real woman! Of course I could never show them what they really wanted, and once they realized I wouldn't take my clothes off, they left rapidly. I still felt like a straight guy, even after everything. Even though the woman I was fantasizing about was actually me... does that make any sense? Well, apparently it did to me at the time. That's where it stopped though. My interest in the couple pieces of clothes I had started to wane and I soon forgot all about cross dressing.

It was around this time that I met him. Who knew the words 'Hey there' and the innocent praise of my story could grow into such a strong bond. We talked, and we talked. Paul was a friend, someone who I...Alice could confide in, share my lack of experience and live through him as he told me of his swinging lifestyle and fuck buddies. It mollified me a little bit, seeing the images and hearing the stories, getting me through the tough years of Uni and into the first year of my job. I even moved in with Laura during this time, the sex life we never had becoming increasingly more uncomfortable, as night after night she would fall asleep as soon as her head hit the pillow.

I strove to keep my online life a secret. Paul never asked anything of me, never wanted proof of who I was. Obviously questions came up and I answered suitably, even creating situations and experiences that never happened. It was like he didn't care about who I really was. He trusted me, and I cherished that feeling. I still believed I was straight, even at this moment. Our stories always included a woman, whether it was about how he'd gotten together with someone, or it was just us sharing porn videos and other stories that took our fancy... I never had a sexual attraction to him, but there was an emotional connection growing there that I wasn't exactly aware of.

The more I talked with Paul, the further afield our conversations ventured. We discussed all aspects of porn, from animals to aliens. One of the things that struck me was the subject of transsexuals and she-males; he even sent me some videos showing some gorgeous girls, I mean stunning! Women you wouldn't expect to be packing a sleek, thick cock. I have to admit, I grew curious. The more I thought about those cocks, the more the curiosity at what it would feel like to take one in my mouth. Would I be good at it? The idea that it would be a man behind it didn't interest me. I still wasn't attracted to men. But a fascination of playing with a dick took root. I even started watching bisexual porn, the ones where the man would be pounding a woman from above, his cock slicing in rhythm to her screaming moans while he grunted as his own ass was being brutally used by a man, or perhaps a woman with a strap on. But that's all it was, a fantasy, to go along with all my other unfulfilled dreams. I put all that aside, for the love of Laura.

Well... I thought I had.

Paul surprised me, shocked me is more the word. With no strings attached, he bought me a voucher for a sex toy store. It's not something I had ever contemplated before, sex toys were always too expensive, especially the male ones. I didn't use it for ages, thinking that there was some hidden catch that I wasn't seeing. In the end though, I relented.

I had within my grasp the ability to simulate some of those hidden fantasies, without putting myself in any risk, without putting any pressure on me... I bought a Fleshlight, essentially a pussy in a case, a prostate massager and anal lube, and an 8 inch fake cock. Of course Paul wanted to hear all about my purchase so I did have to embellish the truth once more. I bought the cock so I could lie... I told myself... but that didn't stop me slipping the realistic looking rubbery thing past my lips...

I explored, I experimented, and I satisfied myself. It was the best experience I'd had to date, barring the first few sexual experiences with Laura. I even tried anal several times with the dildo. It stuck to the wall and after applying a lot of lube, I was able to fuck it. It was more of an emotional high than a physical one as I still struggled, even with the massager, to hit the right spots.

I think this event lead me straight back into cross dressing. I had a whole wardrobe to explore and plenty of time to play. I found a couple of outfits that worked well and did a few more on-line webcam experiences. I started to admit I might be bisexual, but I found it was only when I had this feminine mind-set. Looking back, I think I was looking for a more submissive relationship. During sex with Laura, I was always clumsy, always the one that had to lead, and always not being able to control myself. Of course I didn't let it develop. I dressed up a little bit and not very often, and I chatted on-line but never more than that, I didn't know I ever wanted more than that...

Part 2

Well thank you for staying with me through that. Some of that was hard to put to paper, but I'm feeling better and we can move on. Hello people who skipped that, I still love you, let's get to the meat of this story together.

Laura was working late, as she had a tendency to do on and off throughout the week, and I was just settling in for an evening of porn. It had been a long week of work and I hadn't done much video searching recently, so I was quite looking forward to it. I started as I always did with checking my emails, seeing if anyone had any messages for Alice. Paul did... because I hadn't spoken to him enough at work. I always loved how in the same conversation we could talk about sex and the latest series of The Walking Dead. He was innocuously asking me what I was up to, nothing unusual, so I told him that I was all alone and in the mood for something naughty.

I started my search, bringing up my favourite website when my email pinged almost instantly. That was quick, even for Paul. It was like he'd been waiting for my reply. It was just him asking why I was alone, like he'd forgotten the rest of the conversation to focus on this one fact. I paused, frowning. He didn't know I had a partner, he thought I lived with a friend. I told him she was at work and wouldn't get back till late, shrugged and clicked back to my search. It was a great website. It had thousands of videos, handily categorized, with teasing images of each channel on the main page. I realise I just described nearly every porn website, but I found it worked best for me. I half expected another instant email but it didn't ping this time.

I was just bringing up an interesting looking video entitled "Cum Slut Compilation" when a knock on the door made me jump. I sighed heavily and shifted the laptop from my lap and pulled down my t-shirt to try and cover the semi that had grown in my jeans. I scratched my short hair idly as I shuffled over to the door. The dark evening of winter was all I could see through the frosted glass. I unlocked the door first, leaving the chain to last, an ingrained routine from childhood. Good thing too because as soon as the lock clicked, the door was jarred open to the maximum reach of the silver chain. Shock took over and I instantly tried to press the door shut again, but whoever was on the other side was strong and with a hard kick, the door crashed open. I was sent stumbling back along with the shards of plaster from where the chain had been ripped from the wall.

A dark figure, black mask, black coat and thick black leather gloves pressed his advantage and gave me a sharp kick to the stomach. My breath left my body in a wheeze and my legs collapsed. I sat on my backside heavily and tried to draw in air. I looked up at the intruder and only just managed to raise my arms in time to block the punch aimed at my head. I rolled hard to my left, back into the room and scrambled to my feet. I had almost regained my balance when the man bowled into me, knocking me to the couch. With surprising strength, he gripped my wrists and straddled my waist. I thrashed and writhed and even tried to reach up and bite him but nothing could break his hold.

Another figure, slighter and more shapely, but garbed in the same concealing clothes appeared in my view waving a needle. I panicked and kicked out, pleading and begging but all the man had to do was hold onto my arm tightly and in went the needle, injecting the clear liquid straight into my veins. I could feel the power to fight ebb immediately, my vision grew hazy and in seconds I was gone.

No time passed. That's what it felt like. I closed my eyes for a second and my whole world had changed. Gone was my comfortable living room, here was... where was I? Questions seemed to rise to my consciousness first as my eyes flickered open. I was greeted by the sight of a stark white ceiling. I didn't know what I was laying on, as I found that I couldn't feel anything throughout my body. In fact I couldn't move, not even a little bit. My eyes rolled in my head, and I let out a helpless groan that reverberated from frozen lips. Someone was there. I could sense them, just out of the periphery of my vision. I could hear the slight shuffle of clothes, the quiet exhalation of someone watching. I tried to cry out for help, but all that would come out was a single beleaguered moan. The sound of a door closing softly caught my attention, and I listened hard to every footstep of their high heels approaching.

I was stunned, not only physically, but mentally, by how sultry the woman was who appeared above me. She regarded me coolly as she leant against whatever I was laying on. With a little toss of her head, she flicked the dirty-blonde hair from her face and her painted red lips curled as she noticed my eyes drop to the tight black corset that pushed her breasts up to form wonderfully soft mounds. I made another groan as I attempted to speak but she lifted a red tipped finger and pressed it softly against my lips. The woman was beautiful in her own way, not movie star gorgeous, not air brushed perfection, but striking. Her carefully contained curves and just the way she held herself, the confident, self-assured smirk gave her an undeniable attraction.

She glanced somewhere beyond me and nodded her head once.

"He's awake." Her voice, smooth like silk, made it difficult for me to register that there was someone else in the room with me.

"Good", the reply was warm and masculine. I didn't recognize it. I think anyone would be as terrified as I was at this point. I genuinely thought my organs were going to be harvested. My panic was only just contained by the fact I couldn't move a single muscle.

"You know..." came the voice, right by my ear. I'd have jumped if I could, "You're a bad man." The voice grew slightly distant again as whoever it was straightened up. "You lie; you deceive, all for your own personal gain. Your girlfriend, you love her right? You treat her well?" My heart pounded in my chest as he went on his tirade like he knew every detail about me. "Wrong. The life you made with her is fake, it doesn't exist. There's only one time where you ever tell the truth, the only time... you are real... I think you know what I'm talking about... Alice."

Alice

Oh God

"How long has it been, four, five years now? I shared my life with you, I let you in and what do I find. I find I'm being deceived, being used by some bitch with fantasies he can't fulfill"

...Paul...?

The man walked round to stand beside the woman, who slipped her arm about his waist. Her eyes sparkled mischievously as she clung to him, watching the one sided exchange. I widened my eyes as I looked upon a face I'd seen so often in hundreds of photos, in videos. Paul, the man I had been emailing, the man I thought was my friend, the man who had shared his life, his experiences and asked for nothing... He'd found me and he knew the truth...

"Glad to see you recognize me Alice. You should." I fought, I concentrated so hard that I thought my head would explode, I just wanted to run, to get out of there, to stop these people but I couldn't... It wasn't a hateful expression on Paul's face, not even cold. He seemed happy, like two friends meeting in a social circumstance. His hair always looked the same as in all his photos - black and short at the sides with a casual rough look on top that was meticulously crafted everyday with hair product. His brown eyes were large and had long black eyelashes that he'd said were the envy of all women. His face was roundish and he had a couple of scars, one on his neck from shaving and a small one on his temple that stood out against his toffee-caramel skin. Overall he wasn't a bad looking guy all told; he must have been alright to live the life he did.

Lexavier
Lexavier
21 Followers