Ever since I can remember, I’ve been drawn towards femininity, from wearing my mum’s silk nightdress when I was just four, tottering around in oversized heels and making a colourful mess of my face at the dressing table. It was good, it was girly, it was me… but it was wrong, or so I thought! I was a boy, and dressing up with makeup was for girls. But it was also so very right for the crossdressing transvestite within me. So my anxieties didn’t stop me from my early experimentation, trying different lipsticks, playing with eye shadows and mascara, and looking on enviously as girls got to wear the clothes that I wanted to wear.
The only girl’s clothes in the house belonged to my mum, and they were far too big: not right the crossdressing transvestite clothes for me. Even then I just wanted to feel absolutely right as a girl: truly feminine and stylish. I remember growing up not knowing anything about being a crossdressing transvestite. I just remember liking girl stuff. Then, I saw a film on the television: to this day I don’t know the name of the film, but it’s had a long-lasting impression on me. It was about a man, who met and befriended some crossdressers. It was set in the 1930s. He was ‘straight’ (whatever that means), and they slowly brought him into their world with a little peer pressure, bit by bit.
For him being a crossdressing transvestite started with a loan of a lipstick; he tried it, enjoyed it, and was a little turned on. When they met, they’d ask questions, and lipstick became mascara, blusher, eye shadow … he tried a dress for the first time, stirring those crossdressing transvestite emotions deep within him: it was exciting, now for heels, lingerie, the hair and nails … eventually, he was meeting his friends as a woman, he had ‘changed’ and it was natural. This moment was a life changing not just for the man in the film but for me too. I didn’t know other people felt the same; I hadn’t heard of a crossdressing transvestite before and certainly didn’t connect myself to being one. I needed to know more about this incredible world.
These were the days before the Internet. The mere thought of being a crossdressing transvestite was taboo. Alone with only the memories of the film and a growing urge to become more feminine myself. But I wasn’t gay: I don’t fancy men. I was confused and didn’t understand. I always had a strange feeling of being a woman in a previous life, and drawn to a certain style of crossdressing transvestite clothes: long skirts, corsetry, long hair pulled back. Then I saw crossdressing transvestite adverts in papers: telephone numbers to call and speak to someone like me. This was too much to resist and I started calling other crossdressing transvestites just to chat.
I’d dress up as a crossdressing transvestite as much as I could, when my parents were out the house, and just enjoy feeling complete. Then as I grew up, and started going out with girls, I’d be dating the girls I wanted to be! My crossdressing transvestite dream girls! I’d be attracted by their hair, clothes and makeup, and at times, and sometimes even tried some of their clothes without them knowing.
I got a job and started earning money, but I couldn’t buy my own crossdressing transvestite clothes. I had nowhere to put them. All the time, I was still one of the lads, I had many girlfriends and I kept my crossdressing transvestite secret hidden. I suppressed it for a while.
I got married and have a wonderful wife and a couple of great kids. I love them dearly, but I still have the same inner feelings! I now know so much more of this crossdressing transvestite world. It’s helped me understand that I’m not alone, and that it’s ok!! However, being a crossdressing transvestite is not something I’m willing to share with anyone – there’s just too much for me to lose! I’ve tried the occasional dressing service for a makeover. I’ve bought makeup and heels the occasional dress, and become my true identity ‘Cassie’ every now and again when I’m in a hotel overnight away with work. But I always get a guilty feeling, a thought of I shouldn’t be doing this. And when I look in the mirror, it’s not the same crossdressing transvestite girl that’s in my head.
I want to enjoy my crossdressing transvestite life; and it’s not hurting anyone if they don’t know! But it’s really difficult not being able to share Cassie with anyone! I’ve often had a fantasy of being kidnapped, and transformed into a woman against my will, and having to live my life out as Cassie: my delicious crossdressing transvestite dream! I’d stumbled across feminization hypnosis by chance, and saw a link to JJ at ‘Dress Me Up’. Well, my first thought was, “She’s absolutely stunning; she wears clothes that I could only dream about and her makeup is to die for.” I realised at that moment that I would have to meet her.
Could she help me become the crossdressing transvestite girl I’d dreamed about my whole life? Could she help get rid of the guilty feelings and give me the feminine outlet for which I craved? I put it off a few times and then plucked up the courage to call. She so understood right away and made me feel so at ease on that first tentative telephone call, that I couldn’t wait to meet her and help find Cassie together. I booked a crossdressing transvestite appointment, and couldn’t wait to get there. I booked a day off work, but planned to travel overnight, allowing myself the luxury of going straight to a hotel after my visit.
I pulled up outside her apartment, my heart racing by this point, and called to say I’d arrived. I knocked at the door, and when it opened I met my JJ for the first time. She was gentle, supportive, understanding … and so completely sexy and appealing to all the senses: true sensuality with a wonderful clear-headed intelligence and fun-loving personality to match. We sat and talked about Cassie, who she was, what she liked, what clothes, makeup, look, feel, her deepest desires … I was in heaven, I haven’t been able to talk like this with anyone in my whole life, and I had four fabulous hours ahead of me. This was the start of my crossdressing transvestite dream becoming a reality.
I stripped from my male clothes, and stepped into the crossdressing transvestite unknown. I was guided to the bathroom, a bathroom with candles, feminine scents, perfumes, and cleansing lotions and face masks, I was about to start my journey, the crossdressing transvestite journey to find out who I am, who Cassie is. After cleansing my face, JJ had run me a luxurious bubble bath. I climbed in. I’ve had bubble baths before, but this was different, my senses were heightened with the depth of my anticipation. JJ brought me a glass of champagne and applied a facemask, to deep cleanse my face for my crossdressing transvestite makeover: delicious!
I stepped from the bath, dried myself and pulled on a beautiful and feminine silken robe, stepped into heeled slipper and I’m sure I glided into the boudoir. This was genuinely intoxicating, and I felt so at ease, chatting with JJ as if we’d been girlfriends for years. As I sat in the boudoir, we chatted about the crossdressing transvestite look I was going for. I’m a girly girl, not a tart or diva, so wanted just to feel as feminine as I could. I’d asked for some false nails, I’ve always wanted long nails, painted … so feminine. JJ had bought some for me, but didn’t have any sticking pads, only glue … acetone was used to remove them later. Well, I had business meetings the next day and had to drive to London, I couldn’t run the risk of them getting stuck!
But, at that moment, I was becoming Cassie. The crossdressing transvestite atmosphere, the femininity of JJ’s boudoir and everything about the moment said do it, be as feminine as you can be, enjoy it and live with whatever comes, it was titillating, exciting. The rush of crossdressing transvestite adrenaline I had when I said “do it” was a moment that will live with me forever! JJ asked if I was sure, but there was no turning back I wanted so much to be a woman at that point being a crossdressing transvestite scared and excited me in one go.
As each nail was applied, and glued in place, I started to feel like a girl. I changed inside, I felt Cassie taking over, I can’t describe it, JJ kept winking at me, and I loved every crossdressing transvestite minute! My nails were on, and they felt like they were never coming off, we painted them, and my toe nails, and then it was time to apply my makeup. The feeling of having foundation applied, powder, eyebrows pencilled, blusher, eye shadow, eyeliner, mascara and then lipstick was my every crossdressing transvestite fantasy, I now felt like a woman. I had desires I’d never known before. I wanted my dress and heels, I wanted my breasts to grow, and oh, how I wanted to stay like that forever.
And perhaps the strangest sensation of all: I wanted a man: I was a woman and it was utterly delicious. Being with JJ had allowed me to go beyond being a crossdressing transvestite into true femininity. Don’t ask me to explain! My time that crossdressing transvestite afternoon with my JJ was the happiest few hours I’ve had in a long time, and only JJ and I know about it. This is only the start of my journey to find Cassie, but it’s a journey I’m going to share with JJ. I can trust her, and she knows what I want, she’ll help me get there.
It was good, it was girly, it was me … and it was so right!