How Alice Came to be a Reality

In my twenties, sex finally stopped being a mystery and started to become a reality. After a spell living like a monk in my early twenties, my mid-to-late twenties brought a kind of sexual renaissance. I was meeting more women, feeling more confident and embarking on an exploration of my mind and body I hadn't dared to before.

Then came Melissa, she was a game-changer, a woman of wit, sensuality, and boldness. We met at a house party and I was immediately drawn to her unapologetic charm. I bit back to her sharp barbs and she looked shocked, implying that she'd never experienced that before. I was so turned on by her and our mutual flirting led to us later snogging and then having sex, struggling to keep our hands off each other.

Melissa had no inhibitions. She would saunter naked around my flat, and tease me into doing the same. Her ease with her body was revelationary, but it also threw a spotlight on my own restraint. While she was open, bold, and curious, I was still shackled by secrets I hadn't dared to say aloud.

One night, I slid my fingers between her legs, feeling her wetness as she spread herself eagerly for me. She guided my hand, whispering, "put one finger in my ass." I hesitated, but she reached down, dipped my finger into her arousal, and pressed it back to her rear. I followed her lead and the feeling of her tight ring of muscle squeezing around my finger made my cock twitch with need. As I savoured this new experience, I also wanted to feel the same for myself and feel her finger inside me.

I couldn't ask, not yet, as I was worried about the shame of my past and ghosts that had lain dormant for a while. Despite snogging girls, by eighteen, and the period between school and university I was still a virgin. Many of my peers from school were, the unpleasant product of single-sex schools. During one evening at home, while my parents were out, a friend and I fooled around, getting aroused by fondling each other's cocks and with me eventually taking his in my mouth. First I licked it, then swallowed it and finally alternating the fellating and wanking to allow him to have his own climax. He wanted to fuck me, but despite feeling his salty taste on my tongue and disappearing down my throat, I said no. I feared this would make me gay, something my then homophobia told me was all wrong. In the period that followed, I felt guilty and worried that women wouldn't want me if they knew.

"Would you like me to do the same to you?" she asked me in almost a whisper after I had rubbed her and stimulated her button making her achieve her own orgasm. I froze as I worried that she could read my mind but decided that if she could be carefree when it came to sex, why couldn't I and nodded to signify that I would. Her smile widened as she reached over to remove a tube of lube. She rolled me onto my stomach and her warm slippery fingers gently parted my cheeks as she sought her target. The first touch of my hole sent a shiver through me and I tensed, but then gave way, allowing her inside. The feeling of her inside me, that tight forbidden space finally being opened was overwhelming. As she massaged my prostate, my body arched and I exploded in release, moaning into the pillow whilst my cock was untouched. Melissa finished and as I drifted off to sleep I felt her gently kissing my back and whispering, "you're beautiful like this."

The next morning I confessed to how much I had enjoyed it and in response, her eyes sparkled as she removed a rubber dildo from the drawer. She skillfully eased me onto my side and worked the rubber phallus against my opening, making me part and allow it inside. The stretch was far more intense compared to a finger, far more painful at first, but as she coached me, telling me to push against it, the pain gave way to something deeper, please desire and submission.

A week later Melissa greeted me at the door and in the privacy of her home, parted her gown to reveal the rubber dildo hanging down between her legs, attached to a harness around her waist and thighs. She made me follow her up to her bedroom, undressed me and pushed me naked onto my back, placing my soles on her shoulders as she crawled towards me, lining herself up. Her entry was slow, met with my own thrusts, gasps and moans as I opened up my body for her. Being pegged by Melissa unlocked a physical pleasure and something else, something I had kept hidden for even longer, the desire to dress as a woman.

The concept of wearing women's clothing had lain in my mind for years. As a teen, I had sneaked touches of dresses when I could, but I had never dared to fully dress and the fantasy remained just that, a dream, until Melissa. We were out looking at outfits for Melissa for a fancy dress party and as we flipped through various costumes and I let my hands brush over the satins, lace and leather, my hand stopped when I noticed and then stared at an Alice in Wonderland costume. My hand touched the petticoat tulle and it felt like an electric shock coursed through my fingers and unlocked something in my mind.

"Would you like to try that one on," Melissa asked as she stood there, hands on hips, eyebrow cocked, like she'd been watching for a while, which she had. My heart was pounding as I felt new anticipation of what lay ahead and simply nodded replying that I would.

She marched over to the assistant asking for the dress and an appropriate long blonde wig before physically pushing me towards the changing room. My hands shook as I changed and a long desire was finally being achieved. My attempts to dress in haste were shocking which was revealed as I stepped out and was met by Melissa smirking and then bursting into laughter. Her laughter helped relax me and she came forward, showing a tender side I rarely saw but liked about her, to adjust the dress and wig before telling me to look in the mirror and told me how happy she could see I looked.

"Take off your clothes," she instructed me back at her house as she really wanted to transform me. She slid a satin robe over my shoulders and it felt sinful but also wonderful against my bare skin. She applied makeup, layering foundation, mascara and lipstick and then searched for a brunette wig, slipping it onto my head and adjusting the fit. She handed me underwear and a dress to help me finish the ensemble.

"Go on Alice," she said, handing over the final part to me. I sat there stunned, being called a name, I have now adopted, for the first time. Her words felt like an affirmation of my new persona, someone I had wanted to be for years. As Alice emerged properly for the first time, fully dressed, I nearly cried as finally I didn't look like a man in a dress and looked like someone I could love. Melissa also liked the new me, stepping in behind me, placing her hands on my shoulders resting her chin and savouring the moment.

The next weekend we went shopping, spending time in a bigger city, allowing us a degree of anonymity. Melissa led me through makeup counters, choosing the right shades and asking the right questions. She helped me pick out underwear and a wig matching my face shape. Our final stop, a charity shop, allowed me to try on and acquire the start of a wardrobe selecting dresses and footwear, which I tried on and chose what made me feel most myself.

"They see this all the time," she told me on the train home. "You're not a weirdo. You're just you." Back at her flat, we went through the transformation ritual again, but this time, she took her time. In silence, she applied makeup, fastened my bra, inserted the breast forms she'd acquired online and clipped on earrings. When I stood in front of the mirror, Alice looked back, not perfectly polished, but unmistakably real.

Despite finally starting to look physically like Alice, my female deportment needed a lot of work. She helped me practice, teaching me about posture, walking, and gestures and she displayed patience but was also flirty, gently touching me as she adjusted my poise and when we'd had enough she suggested we stay in, order a takeaway and enjoy each other's company.

Later we cuddled on the sofa and kissed slowly, enjoying the intimacy of each other and as she removed my panties, exposing me. I wanted her, I wanted to feel her inside me and as she did she called out my new name making me Alice forever and not wanting the life that had been before.

By the next morning, something had shifted. We lay in bed, tangled up in the sheets and warmth, and she looked at me like she was seeing someone new.

"You're really becoming her," she said softly, me nodding in reply. I told her I wanted to keep going with this and live as Alice more often and learn everything needed to pass myself off as a woman, going out and enjoying the pleasures that come with it. Melissa smiled but she hesitated as she did so.

"I love this part of you, but I want something else, something steady. I need a partner who is..." She started with but didn't finish as we both knew that Alice was blossoming but Melissa didn't fit into the picture. I had to admit that whilst I still loved Melissa and her body, wanting to touch her, kiss her and penetrate her, I was enjoying being her submissive or bottom more, feeling her inside me and the mind fuck that comes with being called her bitch or whore.

We didn't break up with tears or fights. It was gentle, and respectful as we transitioned into friends, occasional lovers. She taught me how to apply makeup solo, helped me build a wardrobe, and encouraged me to walk taller even when dressed. Eventually, she met someone else. We drifted apart, quietly, as I moved into a new chapter.

I started dressing more regularly. I perfected my makeup routine, learned how to tuck, how to pad, how to carry myself like a woman. Alice became more than a transformation, she became me and I started to embrace the life that lay ahead for her.