Prologue

Relationships are complicated at the best of times. And in my experience they have been made all the more difficult because of my irresolute compulsion to crossdress. No matter how hard I tried (and, believe me, I TRIED), I could never bury my desires deep enough for them never to resurface. In the end I stopped trying to deny who I was. That was probably the best thing I could do for ME, but it certainly did not help my love life.

I had been with my first girlfriend, Cindy, since the first year of university. Our courtship spanned 7 years until we were both in our mid-twenties. It was aged 21 that I first discovered my desire to crossdress: I began sneaking a pair of her panties from her drawer every so often and wearing her dresses whenever I was home alone. I tried oh so hard to resist the temptation to wear her clothes but after every occasion on which I successfully restrained myself the longing only resurrected itself more powerfully.

Eventually, I resolved not to wear her clothing as I recognised the boundary that I had crossed by doing that; so, I bought my own stuff, online, which I housed in the attic of our rented apartment. For four years I added slowly to this collection and indulged in my wont only when I was certain that I was to be left on my own in the flat for more than a couple of hours. My dressing escalated to breast forms, panty gaffs, a long brown wig, makeup, and even some jewellery, all of which I learned to apply through YouTube tutorials. Sure, I was unconvincing at first, but slowly and surely I acquired the skills to present myself as a passable woman.

It was as I became more assured in my dressing that my desire increased from wanting to just dress occasionally to wanting to do it more often. I began to resent the time I spent with my girlfriend as it invariably meant that I was confined to my male self. I found myself delighted whenever she left me alone. This was causing a strain on our relationship; though she was unaware of the cause on my end, the strain nevertheless became apparent to her, too.

One day we had a heart to heart. She asked if I could feel us drifting apart. I said that I could. She asked if it was anything she had done. I said no, as it wasn't her in the slightest. She then asked if it was another woman. In a way, I suppose it was...but that other woman was me! I said no to her question.

She then asked what is was. She implored me to tell her. So I did. I had no prior intention to do so, but the moment felt opportune. And it was only fair, for her and for me too, I suppose.

I cannot remember the words I chose to describe how I was feeling, but I made it clear how I felt: I wanted to crossdress and do so without hiding it from her any longer. She sat stunned for a bit not saying anything. Then she said that she had to leave, to spend some time away from me and digest what I had just told her.

For two nights I was left to stew in my own thoughts wondering if I had irrevocably broken our relationship with my revelation. I even wondered if she'd ever return at all. But she did return: she said that though it wasn't easy to understand my desires, she still loved me for who I was and wanted to continue our relationship. If that involved accepting my crossdressing habits, so be it.

I was overjoyed not to have lost her. We continued our relationship for a little while hence. She refused to have intercourse while I was dressed which I accepted, but I was free to spend as much time dressed around the apartment as I wanted. However, I was not to dress in front of anybody else, and certainly was not to venture out into public crossdressed. I accepted these terms: I had no intention of going public with my secret nor for anyone else to find out.

I thought I had hit the jackpot, but it became obvious not too long after that this arrangement wouldn't survive long-term. Even though I never dressed on such occasions, we were having sex on a less and less frequent basis. And when I was dressed around the house, she became increasingly cold and hostile. It was perhaps three months in when we called it a day: well, I say "we", in reality it was her who called things off.

To say I was heartbroken would be an understatement. But, in some way, I think I understood her. She had grown to love me as a man; seeing me as a woman must have been so conflicting for her. In the end, we just grew too separate and our relationship was never going to survive that. She broke things off with all the cliches: "it's not you it's me" and "we'll still be friends". But neither of those things were true and I knew so immediately: it was because of me and my dressing that she was breaking things off, and we wouldn't be friends or stay in touch - I don't think she ever looked at me the same way again after I revealed to her my secret. Upset but accepting of the situation, I asked just one thing of her: please don't tell anyone about my crossdressing.

She agreed to this but I'll never know if she upheld her end of that bargain. The split was amicable so I hope that she did. But, deep in my gut, I knew that she may let slip, particularly in some drunken stupor while out with friends. That thought, and the idea of being outed to people who knew me, haunted me. It haunted me so much that I moved city. I decided that I needed a fresh start as well as a place where I could be my female self, Mandy, whenever and wherever I wanted.

I found a nice flat and a new job and got settled into things quite quickly. It was a relief to be in a new place with new prospects and no history. Things were great for a good few months, until I began to feel lonely.

The answer I thought of: dating. The catch: my crossdressing.

I went on a few dates as myself. I met some wonderful women, all of whom I would have been happy to pursue a relationship with. But the skeleton was always lurking in my closet and I broke it off each time before things could get serious. Maybe they would have accepted Mandy. Maybe if I'd have just opened up to them, things could have developed and blossomed. But I just wouldn't take that risk, so I'll never know.

It was after a few dates and one night stands that I began to question my sexuality. The sex I was having was ok but nothing noteworthy. Everything was vanilla and I wanted more. I decided to try the gay dating scene. I had always considered myself open-minded and adopted the mantra: "you'll never know unless you try."

I had dates with multiple men. And, I must admit, the sex was feeling a lot better. I topped and I bottomed, and enjoyed it both ways. But this was all as a man, and the elephant in the room was ever-present. Yet, for some reason, I felt more comfortable disclosing this elephant to the men I was seeing and did so on each occasion after a few dates. The result, however, was the same each time: none were interested in a crossdresser.

I found myself at a loose end with my relationships. I thought I'd never find love given my crossdressing, but being Mandy was simply not something I was willing to give up. I'd all but resigned myself to a long and lonely and loveless life.

It was at this point that I struck up a friendship with Jasmine. She lived in the same block of flats that I had moved into. One morning, she knocked at my door to ask for some sugar. We got talking, and I invited her in for a coffee. I won't bore you with all the details, but long story short we realised that we had a lot in common. The main thing was that I was lonely and she was lonely too; so, we agreed to be pals, and our relationship developed from there.

One evening, we went out for drinks at a local bar. We ended up having one too many and were kicked out at closing time. In no rush to end the festivities, we returned to Jasmine's place to continue drinking. It was as we were sat on her sofa, another half a bottle drunk between us, that we both revealed our secrets.

She went first: Jasmine is transgender. It slipped out of her mouth which she covered as soon as she said the words. She looked terrified at first. But I hugged her tight and said that I was glad that she told me. The bravery she then displayed in telling her story, how she had come out aged 18, been rejected by her friends and family, forced to move away and build her own life as a woman in a new city, was spellbinding. I was in awe of her and told her just as much. Also, I was thankful that she felt she could be so open with me. That touched me deeply.

After a little consideration I then told her my story. If she could be so brave and transparent, why couldn't I? She listened earnestly in spite of her inebriation and smiled at me reassuringly throughout. When I finished, tears were forming in my eyes. She pulled me in and hugged me tightly. Since that moment, we have been the closest of friends. I feel utterly blessed to have met such an angel on this Earth.

Five years passed between that conversation and the events of which I am about to write. It was a Sunday morning in June when I answered the knock at my door to find Jasmine standing there, a smile as wide as a mile on her face. I invited her in, made coffee, and we sat down to talk.

"I've got some great news", she said.

"What is it?"

"The Rainbow Bar is hosting a speed dating night this Friday".

"So?"

"It's perfect for you!"

"Um, thanks for thinking of me Jas but we've already been through this. No matter if I date men or women, I can never get over the "Mandy" situation."

"I know, I know, but this is different."

"How?"

"Because it's a speed dating event designed for crossdressers!"

I was processing what she was saying as she continued.

"You said you were never able to bring up Mandy to anyone you dated, right? Or that when you did, things broke off? Well, here you don't have to worry about all that. You turn up as Mandy in a club we know well, talk to a few people, and if you like any of them you just say so at the end. If they like you too - if they like Mandy - they'll say so. Match up with any of them and you could be onto a winner. If you don't, at least we can gossip about your dates afterwards."

"Gee, I don't know Jas..."

"Babe, what are you not sure about? It's a no-lose situation that you may just get a big win out of. I know you're desperate to meet someone, but, let's be honest, your current methods aren't working. I think you'll have fun. And this way your 'secret' will be out in the open from the get go. You can start a relationship on the right foot for once and not be scared of having to reveal Mandy at a later date. That sounds good, doesn't it?"

"I mean...yeah, it does."

"Absolutely too right it does!"

"But...Jas...I'm still not sure."

"Oh, please, just try this for me? I haven't done you wrong before, have I?"

"No."

"And you know I'm only ever going to push something if I think it's right for you?"

"Yeah, I suppose."

"Great, then it's agreed! I'll come by Friday around 5. It starts at 7.30, so we'll have plenty of time to get you ready."

She leant across and gave me a hug.

"I think this'll be good for you."

"If you say so."

"I know so."

With that, we drank our coffees and moved on to other conversations.

So, this is where my story really begins. That following Friday night I would be heading out for my first date (or should I say dateS!) as Mandy. A night that would truly change the course of my life!