This is my true sissy confession. Ever since I was sixteen, I have worn women's clothing. It started innocently enough with a pair of shiny black high heels that I found left by the front door. My eyes widened as the sunlight reflected off the patent leather, quickly I grabbed the shoes and rushed off to my room to try them on in secret.

Not long after this, I began to notice my sisters' lingerie and garments laying around the house, curiously trying on my first pair of pantyhose and relishing the feeling as the sheer nylon stretched against my smooth legs. Soon after, I began to try on full sets of underwear, nylons, panties, and bras, and before long I had advanced to wearing dresses and makeup.

I would always feel a small sense of shame and guilt when I wore women's clothing, only ever dressing alone, in secret, or when I thought no one would catch me. I began to notice women more meticulously, admiring their clothing, developing a sense of jealousy towards them. Wishing I could dress and look just like them.

The first time I ever came was in my aunty's house. I'd been left alone for the day and decided to take a look in her bedroom. Tucked away in the back of her dresser drawers were dozens of vintage lingerie items from her younger days. After trying them on, I lay on the bed and began rolling around, dry-humping the soft mattress and feeling the silk sheets rub against my slippery body.

Suddenly, I felt an overwhelming rush of euphoria as waves of pleasure ran through my body; followed by jolts of elation as my hips shuddered, releasing streams of come all over the silk garments. When I finally stopped trembling, I noticed the wet patch covering the panties, and quickly raced to the bathroom to clean up.

After several months, I realized my habit had become an addiction. I would spend my days fantasizing and dreaming of being alone, dressing in secret at any opportunity. By this time, I started to dress more and more slutty, admiring my clothing as I stood jerking off in front of the mirror, staring at my sexy body.

This continued for a few years until I decided to stop dressing up altogether. I had met a girl and wanted to have sex as a man, attempting to become "normal". The first time we had sex, I remember staring at her body, admiring her feminine curves and beautiful but tiny breasts.

Losing my virginity wasn't exactly anything to write home about. In truth, it was very ordinary. Kissing on the bed, fondling her small breasts, while I slide off her jeans and panties. Then, after removing my clothes, I laid on top of her, slid my cock inside her pussy, pumped for a few minutes, and came almost immediately.

I remember, the last thought I had before ejaculating, noticing her bra and panties on the side of the bed and imagining wearing them myself. Within seconds, I came and that was the end of that. She seemed disappointed and quickly left soon after. We broke up not long after that and I never saw her again.

Several months later, I met another girl and began to have sex more regularly. Most of the time, I would go down on her first to try and make her come before penetration. During sex, I would fixate on her clothes or imagine the situation being reversed while we fucked, and would always come extremely quickly.

Sometimes, she would ask me to go down on her again, after I came, and I remember, vividly, the taste of my own come as I licked her pussy. I really enjoyed giving her oral pleasure, making her squirm and moan. Something about pleasuring another person was so exciting and sexy to me.

Eventually, after a year or so, she broke up with me. Citing the fact that she wanted to travel and knew she would be tempted to fuck other guys while away. We stayed friends and she even asked me to house-sit for her parents while they were all away on holiday.

Literally, on the first day, after feeding the cat, I ventured upstairs into her room and began to look through her wardrobe, trying on a variety of her clothes.

By the time I realized what was happening, I was dressed from head to toe in her lingerie, jerking off on her parents' king-size bed. Screaming like a girl as I came, shooting come all over my face and licking off every drop.

For the remainder of their holiday, I spent every moment dressing up, discovering her moms' naughty drawer, full of luscious lingerie and sex toys.

When the experience was finally over, I was left feeling empty and alone.

I tried again to purge my feelings, dating a few more women, which usually ended with me being dumped shortly after the first sexual encounter. The worst experience was when I met an Italian girl called Sofia. She was so sexy, always wearing fashionable and luxurious outfits, with perfect makeup.

For the first time, I truly felt attracted to a woman as a man. I wanted to fuck her with my hard cock and make her come over and over again. At her birthday party, after a lot of flirtation from her, and a steady flow of drinks, I thought we might actually get together. But after a short trip to the restroom, I saw her leaving with one of my friends.

I remember the look on her face as she walked out the door, her arm draped over his strong shoulder. The look of certainty in her eye, the expression that told me everything. She was going to fuck him so hard tonight. My heart shattered with regret as I thought about how much of a pathetic loser I was.

Of course, within days I had ordered my first full set of lingerie from the sears catalog, aching to dress up again and free myself from these hurtful emotions. Dressing up, was so much fun, and made the problems in life just melt away.

By this time, I had begun to experiment with anal play. Fingering my ass and moaning like a girl each time I came. It was the early 2000's and porn was now so easy to access online. At the click of a button I could watch any act I desired, chatting with strangers and sharing pictures of my slender body, dressed in the slutty of outfits.

I loved pretending to be a girl, driving men wild with lust as they sent me compliments and messages. I loved flirting with them online, making them jerk their cocks to pictures of me, while we sent dirty chats to each other.

I'd begun to dress up regularly and enjoyed playing with dildos, coming from anal play and moaning like a girl as I fantasized about being fucked. I had no intention of ever acting on these fantasies, not in real life, anyway.

For the next few months, I spent most of my time in my apartment, role-playing and dressing up, taking seductive pictures, and flirting with people online. Porn had become a big part of my daily routine, watching sissy hypno videos and following the instructions. I'd gone from simply trying on clothes and masturbating, to dressing fully en femme, make-up, and well-fitted wigs.

I'd heard that sissies were supposed to only come from anal play and that they should learn to enjoy the taste of come. After learning this revelation, I made sure to only come with a dildo or vibrator in my ass, licking up every drop each and every time I came.

This continued for the next year or so until I met Katey. My first long-term relationship with a girl. Katey and I started dating and soon after, moved in together. I had hidden all of my sissy items in a suitcase, locked safely away in the attic, and was feeling optimistic about things this time around.

Katey used to be a lesbian but had decided that she was now bisexual.

She really enjoyed soft and sensual sex, and she loved it when I went down on her, which I did a lot. For the first time in my life, sex began to feel good. The foreplay was amazing and she would often climax from me giving her oral pleasure. This made it easier when I prematurely ejaculated during sex.

However, it wasn't to last. Within months, our sex began to decrease and I found myself masturbating more often, sometimes while wearing her panties or bras to help me come. One day I stumbled across her web history, which she had obviously forgotten to delete. Her browser was full of lesbian porn and there were web chats saved with dirty messages from other girls.

Eventually, I confronted her about it, and she admitted to still liking women more than men and wanting to have sex with girls. It ended soon after and I always wished I had told her about my sissy fetish. Believing that somehow it would have helped if she could have imagined me as a girl.

It was then that I reverted back to my former self. Dressing slutty and pretending to be a girl, spending days alone in my room, yearning to become a sissy whore. I would photograph myself in various positions, wearing risque outfits and sluttish lingerie. Hoping that someone would tell me how cute I looked, or send me a naughty message inviting me to play.

Every day I dressed up, watched sissy Hypno, and fantasized about being fucked like a girl. My mouth and ass yearned for cock and my female alter ego was starting to take over. I could feel her breaking through, making me do naughty and degrading things, especially in the heat of the moment.

I found that when I was en femme, I became subservient, submissive, and corruptible. My male ego disappeared and what shred of self-respect I had left, would dissipate at the mere mention of a sissy suggestion. If I received a message from someone, instructing me to perform an activity, I obeyed their command.

This spiraled over several years and continues to today when I lay on my bed, dressed in black stockings, a silk basque, and five-inch platform heels, my hair and makeup all done up. Just waiting for the next message from an admirer.

So, this is my confession. Ever since I was a teen I have worn women's clothing. My debauched mind is addicted by intense sissy cravings and like the weak-willed sissy I am, I have allowed my cravings to take control.

I have shown disrespect, and have violated the women in my life by stealing and wearing their clothing and now deserve to be punished. My days are spent dreaming of becoming a sissy slut. Whenever I close my eyes, I see big strong cocks, and wish for an alpha male to take my sissy virginity.

I humbly and pathetically ask for forgiveness, hoping that I will soon live to please my Mistress and Master. To fulfill my destiny and become the good little sissy I dream to be.

This is my true sissy confession.