SissyBecky Ch. 01

The moment my Amazon delivery arrived, my heart started pounding with excitement. I was barely nineteen, and my mother was away for the weekend with her boyfriend, leaving me home alone. The parcels were a collection of personal items I'd bought with my birthday money, items that would turn me into the girl I longed to be.

I took the parcels up to my bedroom and tore into them eagerly, my hands trembling with anticipation as I laid the contents out on my bed. No more wearing my mothers lingerie and stuffing her bras with tissue paper. I now had my own collection, in my own chosen style and sizes. I couldn't wait.

I'd bought a baby pink lace lingerie set, a pair of pink, glossy stilettos, DD silicone breast forms that felt surprisingly real, a chastity device with a vagina front, a long, wavy platinum blonde wig, false nails and eyelashes, a full makeup kit, and the kind of pink dress that only a slut would wear.

I stood in front of my mirror, my five-nine, slender frame, short blonde hair and blue eyes, reflecting back at me. But not for long. Soon, I'd be Becky, not Ben. I started with the lingerie, sliding the bra and panties over my smooth skin, feeling the delicate lace against my flat chest, hugging my tight buttocks, and hiding my small shaven bits.

Next, I secured the breast forms in place, adjusting them until they sat perfectly, giving me the cleavage I'd always dreamed of. I then locked the hard plastic chastity vagina in place with a terrifying click, a reminder of my desire to be a good sissy.

After parading around my bedroom with a beaming smile, I sat at my computer desk in front of the mirror and opened the makeup kit. The array of colours, cosmetics, and brushes excited me further. I began by cleansing and moisturising my skin, before preparing with a smooth canvas of primer.

I then applied foundation, evening out my skin tone and providing a base. I'd watched so many tutorials and practiced with my mothers makeup. I covered any blemishes and dark shadows with concealer. Added warmth to my face with bronzer. It felt amazing. I then added blush, applying colour to my cheeks for that feminine glow.

"Hello there, Becky," I smiled at my reflection, next adding a luminous sheen to the high points of my face with highlighter.

Then came my favourite but most difficult part. My eyes. I applied a base colour of eyeshadow to my lids, then layered other shades, recognising I still needed practice. Next, I defined my blue orbs with eyeliner. Then I darkened my natural lashes with mascara, before attaching the falsies. I finished by shaping my brows with a pencil.

Pleased with my handiwork, an hour later, I moved down to my lips, defining their shape before smearing crimson lipstick. I blew Becky a kiss in the mirror and giggled, then used setting spray to preserve the makeup for longer. The final touch, French false nails. I'm sure I looked amateurish compared to a real girl, but I felt very alive and feminine.

I reached for the long, platinum blonde wig, brushing it gently before placing it on my head like a crown, a halo liberating me from my manhood. It was a sweet feeling that I savoured for a few moments. I then sat before down again and squeezed my feet into the brand new, four-inch, pink heels.

They hurt and would need time to break in, but seeing them shine on my feet made every bit of the pain worth it.

I examined myself in the mirror, seeing only Becky. The DD cup breast forms added a curvaceous touch, helping to create the illusion, along with everything else. I think the platinum waves cascading from my head, and framing my sissy doll face, was my favourite, or maybe it was the fake tits and heels. In truth, I loved all of it.

It was only midday, yet when I slipped on the short, low cut pink dress, I felt ready to go clubbing. A girl can dream, I thought, smoothing my feminine hands and false nails over the tight fabric as it clung to my body. Although I'd never been with a man before, only the dildo I'd previously bought from Amazon, I wished I had a sexy guy in my bedroom with me, giving me his opinion.

Would he approve of Becky, a vision of femininity, a sissy slut with big tits and a confident smile? Or would he just see a silly little boy playing dress up? I felt a rush of excitement at the thought of meeting a man as Becky, a man who'd understand me, perhaps better than I understood myself.

I went downstairs for a light bite to eat, walking around my mothers house like I owned it, the high heels striking the hard flooring as I practised my walk. God, it near killed me. My calves burned like hell and my toes were crushed, but I persevered. I couldn't walk past a mirror without stoping to examine myself, either. It wasn't vanity. It was pure excitement.

Late afternoon, I grabbed my six inch, realistic dildo from my drawer, it's thick girth making my heart pound, and sat at my computer desk. I logged on and went straight to the sissy-hypnosis porn, the videos that had driven me to bring Becky to life. As soon as the dominant, feminine voice began speaking to me, her tone sexy and commanding, I felt home, truly home.

"You are a sissy," she said to me, as a kaleidoscope of flashing visuals and hypnotic spirals pulled me deeper into the fantasy. "A submissive sissy slut." I melted into my chair and licked my realistic dildo.

The video then began to show the most beautiful women and sissies sucking big, thick cocks. Their mouths stretched by masculine hardness, their saliva coating the men as they worshipped them. God, I wanted to experience it. To be on my knees, tasting and satisfying a real man, a big one.

"As a sissy slut, you are desperate to please, to serve and obey. You are desperate to be used." The woman's voice spoke the truth as if she was my mind speaking to me.

"Yes," I sighed my obedience, wrapping my eager red sissy lips around the dildo, sucking it deeper into my warm, wet mouth as my little dick throbbed inside its cage.

"Say your name, sissy," the woman instructed.

"Becky," I gasped, sucking the defined head of my dildo.

"Say it loud and proud, sissy. Obey your desires and submit to the girl you really are."

"Becky!" I exclaimed, then filled my mouth with hard, thick silicone as I watched big cocks being sucked and pleasured.

"You were born to be a sissy, to suck cock and drink cum. It's all your docile brain can think about it, isn't it, sissy?" The woman's voice taunted me with the truth. "You crave it. You want to taste and worship real men."

"Yes," I agreed. "I want to get fucked like a girl."

Drowning in lust and desire, consumed by my fantasies, I lubed the dildo and my sissy hole, then slowly sat down on the sex toy, cupping my fake tits over the lace bra, once the head was inside me. Closing my eyes, I gradually took it down to the realistic balls, groaning as I listened to the videos.

"I'm a sissy slut," I moaned. "I'm Becky. I crave cock and cum. Oh fuck, yes," I cried out, bouncing up and down on the dildo that was stuck to my chair, squeezing my tits, wishing they were real feminine flesh.

I needed more. I needed release. Being the untrained sissy that I was, I unlocked my dick and moved to my bed, the sissy hypnosis porn still playing on my computer. I shoved the dildo deep inside my body, clenching my inner walls around the girth like a real girl would do, and raised my legs high above my head, stroking in the direction of my face.

"Oh fuck, yes! You can do this, Becky!" I urged, feeling my orgasm building.

Moaning and whimpering on my bed, my tight hole twitching around the dildo, I felt a moment of trepidation, of doubt. But it was too late. My body convulsed as I came, my warm cum splattering onto my face for the first time. It's salty splash went inside my mouth. I tasted it, tasted myself in disgust.

It was a very sobering experience. My bedroom fell deathly silent. The porn had stopped, leaving only the hum of my computer. I lay there, covered in my own sperm, the dildo still inside me. I pulled it out, took off the high heels, and stood up, feeling deeply, deeply ashamed of myself.

My reflection in the mirror was a mess. The wig was askew, my makeup ruined, my face glistening with my own release. Shame washed over me like a wave, drowning out the euphoria of the whole experience. What the hell was I doing? I was disgusting, gross.

I'd gone from crossdressing out of curiosity, masturbating in lingerie, pretending I was a girl, to spending all of my birthday money on sissy wear. And for what? To satisfy a weird fantasy. To explore a fetish that I now wished I never had, wished I'd never discovered.

I undressed and dumped everything onto my bed, then stumbled into the bathroom, scrubbing my skin raw in the shower, trying to wash away the evidence of what I'd done. When I returned to my room, the lingerie, dress, heels, and accessories, reminded me of my failure as a young man. I dried myself with a towel, vowing to never do it again.

But when I soaked my hands in a bowl of warm water and pure acetone, preparing to remove the last piece of Becky, she grabbed hold of me tightly. I pulled my hands from the bowl and dried my nails. It wouldn't hurt to wear them for a bit longer, I told myself.

As day turned into evening, the shame I'd felt after ejaculating over my face gave way to those rumblings again. I began to reason with myself. I had one night left before my mother returned home. Just don't cum over your face again, I told myself, slipping everything back on. My makeup was slap dash, a few swipes of mascara and lipstick.

The guilt and shame was gone. I was Becky and horny once more, sat at my computer in chastity. No dildo. Just me and my thoughts, reading sissy erotica and sissy blogs, wishing I could juggle my thoughts and emotions, wishing I could be Becky without anyone in the world judging or caring about my choice.

My mother returned from her romantic weekend on Sunday evening, and all things Becky were securely locked away inside a suitcase under my bed. I was Ben again. I'd cleaned the house for my mother and made everything appear as if nothing weird had taken place while she was gone.

I was a college student, studying business. Around my studies, I worked at a local bookstore just to make some money. Money that I began to save and spend on Amazon, building my collection. Becky wanted a pretty pink sissy romper to sleep in, so I bought her one with matching socks.

She also wanted a sissy hoodie to lounge around in when studying in front of the computer. So I bought her one of those too. I even bought her cheap jewellery and a blonde bob wig that was practical to wear for short periods. Eventually, I'd built a sizeable collection for her. Items she could wear and remove at short notice.

I kept the makeup, nails, eyelashes and full sissy attire for when my mother stayed at her boyfriends for the weekend. When I knew my chances of getting caught were slim to none. I also grew to enjoy the taste of my own sperm, the feel of it splashing onto my face and landing inside my mouth.

I was still watching sissy hypnosis porn too. The videos were a source of pleasure and guidance, reminding me of who I really was, reinforcing my desire to be Sissy Becky. I learned to deal with the guilt and shame, to let go and stop judging myself. I wasn't hurting anyone, except for myself. But how could something that felt so right be wrong?

Sat in my pink and white romper sissy suit one evening, my long, platinum blonde wig falling down my back in waves, my face lightly made up, my clit in chastity and my sissy hole plugged with thick chrome, I logged onto a particular chat site, creating an anonymous profile. SissyBecky.

I posted a few carefully curated photos, showcasing my inner girl. The response was overwhelming, a flood of messages from horny men who were eager to engage me. I smiled, flirting with them, enjoying the attention without my face being seen.

One user in particular caught my eye. He claimed to be experienced with girls like me. Dominant but respectful. He promised that no meant no, and he seemed to understand me and my desires. As we chatted, he offered to meet up and just let me suck his cock, giving me the opportunity to explore with no pressure or expectations. My heart raced at the thought, at the possibilities.

"Forget all the sissy stereotypes, Becky. I'll treat you right," he typed. "I'll teach you how to please a man at your own pace. I'm not interested in exposing or humiliating you. I'd just love to see you in all your glory... and yeah... be your first guy."

His name was Richard and he was in his late forties. He courageously sent me a photo of himself. He was fairly handsome with a clean shaven face, and a brown, faux hawk hairstyle. We talked some more, for a couple of weeks, actually, before I sent him a photo of myself in the pink lingerie and dress. The whole nine yards, but I blurred out my eyes.

I was nineteen and naïve, hoping and preying that my naivety would favour me. I agreed to meet Richard at a motel not far from where I lived. I caught a taxi one Saturday afternoon, checking in with a bag stuffed with everything I'd need. I then set about getting ready, transforming myself.

I would get my wish to stand before a man as Becky. I just hoped I was ready for it, because if my anxiety was anything to go by, I was far from ready. Once I was dolled up as my sissy alter ego, I paced the room in my pink stilettos, fussing my long, blonde hair, trying desperately to compose myself.

God, can you ever be ready for your first time meeting a guy? I was about to find out.