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| Rachael's legendary black dress - as I remember it. |
For this entry, I’m going back to the early summer days of 1996. I was in my mid-twenties and had just started going out with a new girlfriend, Rachael.
We’d got together quickly and unexpectedly, and we’d only spent a few evenings together before I decided to ‘come out’ and tell her about my cross-dressing. I didn’t expect to be dressed as a girl in front of her after only knowing her for just a few weeks, but that’s how things turned out.
Rachael was very intelligent, a little older than me and, ultimately, rather too serious for us to stay together for very long. But, out of all the women I’ve been out with she was the most tolerant of my need to ‘be a girl’ and she’s the only girlfriend who’s encouraged me to go out in public and do it properly rather than to simply pull some women’s underwear on with a t-shirt in a haphazard way in my room.
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| I never did get the chance to go to the club with her. |
Rachael was initially excited by the novelty of my need to cross-dress, and as soon as I’d told her about it she was buzzing with excitement. She wanted to tell her friends but I protested strongly that I didn’t want anyone except her to know about this, at least for the time being.
Rachael had another suggestion soon after: She asked me to allow her and her best friend to dress me properly (in full female drag) complete with wig and make-up so that we could go to a transvestite nightclub in Brighton. (I didn’t do this with them in the end, but it was a tempting proposition, as I’ll describe here in the full story below.)
***
By chance Rachael was a wonderfully enthusiastic tights wearer in her own right, and she’s the only girl I’ve been out with who was happy to wear a real variety of tights rather than standard opaques. I got the chance to see her in thick, dark blue control-top opaques with shorts one day and soft-sheen, neutral sheer tights with a straight skirt the next. This was tremendously exciting and sexy and I loved the way she would vary her tights to suit her mood and her outfit, often taking me by surprise by wearing ones I’d never seen her wear or buy before. She got a kick out of this and I know that for a while she did this as a way of playing to my fetish too. It was fun!
Rachael also had an arousing habit of putting on her bra, knickers and tights first thing in the morning before fixing her hair, make-up or even having her breakfast.
Sometimes she’d put her shirt on as well, but often she wouldn’t; she’d just be in her underwear meaning that I’d spend a very happy, (but often very frustrating 30 minutes) staring at her as she padded around the house – wearing tights on most work mornings and many of her weekends too. Wow! It was particularly fascinating when she was wearing some sheer 15 or 20 denier tights, as I hadn’t really seen a girl wearing them close-up before.
Rachael told me that she’d always done this – get half dressed in the morning to stop her clothes getting messed up with breakfast crumbs and make-up smears. It wasn’t for my benefit, then, but it felt like it was. Apparently her mother had done the same thing when she was growing up and it was a habit she’d naturally copied and stuck with herself.
She always popped back upstairs to get dressed just before leaving the house, and I was always amazed at how quickly she did this. I’d see her legs and bottom wrapped in some lovely brown or blue tights go up the stairs. I was always careful to be ‘coincidentally’ in position at the foot of the stairs at this particular moment each morning, so I could watch her go up and see as much of her as I could. Two or three minutes later she’d be in her work clothes or weekend dress and on her way out of the front door. Rachael knew this but never complained, and part of me loved the fact that she might have done all of this a little theatrically - emphasising her femininity and exuding effortless, everyday female glamour for my benefit as much as for her own practical reasons.
***
I do have some fond memories of Rachael (and not just because of her clothes) but I don’t think I was really in love with her, or she with me. We met at a time when we were both quite unsettled in our personal lives. We were both discontented with our jobs and we became intimate companions whose mutual situation brought us together rather than any deep emotional bond. I know a lot of people who've done something similar. By chance they've ended up in a relationship that's not really comfortable, but for a combination of reasons have stayed together with someone even though they're both fully aware that this isn't really meant to be. Rachael and I separated on good terms without tears or histrionics after we'd been together for just over a year, and if I'm honest I’ve not really thought of her a great deal since then. But, a quick glance at Facebook has reassured me that's she doing very well for herself and seems happy - much happier than at the time we were together and I'm really glad that things have worked out well for her.
But, back in those first moments of novelty and discovery with Rachael and myself when we tumbled into intimacy with each back in 1996, things promised a lot more than a painless, awkward separation. For a while I thought the gateway to cross-dressing peace of mind had been opened by this curious and pretty young woman.
*****
As I mentioned earlier, it was after knowing Rachael a very short time, on our third or fourth date that I told her about my love of tights. We’d spent the evening talking on the sofa, drinking red wine, smoking Marlboro Lights and telling each other our interesting stories. As the evening wore on we become more daring and flirtatious, and we inevitably arrived at our biggest secrets.
Rachael’s big secret was a surprise – and again, I’m aware that this sounds like male wish fulfilment, but this is again true. Rachael admitted that she’d once slept with a girl when she was at college. She was confident now that she wasn’t really gay or bisexual, and if she was honest she hadn’t really fancied the other girl, but one evening, thanks to a combination of drink, circumstances and a desire to cast convention aside, she’s allowed herself to get flirtatious with a friend and things had escalated into a full blown night together where plenty of sexy things happened.
I was fascinated of course, but Rachael wouldn’t be drawn on too many details and said that I was one of the only people she’d ever mentioned it to. She wasn’t embarrassed about the gay aspect, but rather she regretted it as you would any one-night-stand with a close friend. After she’d been so honest, I knew I had to be too.
*****
The words came a lot more easily than I’d thought, and it was a lot less traumatic than when I’d told Katie several years before. I simply told Rachael the truth: That I loved women’s clothes, but tights in particular were my real obsession, and had been since I was a little boy when I’d first wanted to wear them.
This is the conversation, in as much detail as I can remember. It’s not verbatim of course, but I’d like to think of it as a tissue of truths:
“You mean you’re a tranny? Do you dress up as a woman?”
Rachael was clearly more curious than shocked - her voice suggesting intrigue, not fear or surprise. She was, (unsurprising considering her personality) rather detached and analytical about what I’d told her. I went on:
“Well I’ve never been out in public but I am a bit of a ‘tranny’ I suppose. I’ve got some tights and a few female clothes of my own that I wear around the house. I don’t go out though.”
“Really?” She giggled. “I’m really surprised, I’d never have thought that you’d be into anything like that. Well, you hear about it and read about it don’t you! I’ve always wondered about why a man would want to do it. God I’d love to tell Bronwyn, (her best friend – a slight eccentric character and a real fag-hag) she absolutely loves drag queens.” Pause, then a concerned expression. “You’re not gay are you?”
“No, it’s nothing to do with fancying men. I just get this burning urge to wear women’s clothes, it’s like an addiction. When I feel that I need to get dressed it’s really hard to ignore it, especially when I want to wear tights. But I only do it here by myself.”
“Does anyone else know? Did you do this at university?”
“No one except Katie (my ex), and she’s promised not to tell anyone else. You’re not going to tell Bronwyn are you?”
“No, no, not if you don’t want me to. But I didn’t see that coming, that’s just so weird. Why do you like tights so much, I can’t imagine why you’d like them. (My last boyfriend) ….hated me wearing tights and said that they made me look like an old lady.”
“Well, it all started at primary school when…. “
I told the tale, as written up in all of my blog entries about my earliest stirrings of transvestism.
“Have you worn anything of mine without telling me?”
“No, of course not.”
“Do you want to wear something of mine? Oh my God, I’ve got to see you wear something now that you’ve said that.”
“No, I’m too embarrassed, I’m not really ready now.”
“Are you really a tranny? I want you to wear something for me.”
*****
It felt as though Rachael didn’t believe me, that my personality was so mundane and unflamboyant that she’s didn’t believe I was capable of cross-dressing- something she had in her mind as something really camp and outrageous.
So, whilst I wasn’t entirely in the mood to do it, I got dressed in front of her that night with her guiding me and egging me on. It turned out to be fun rather than arousing.
*****
I admitted that her short, black shift dress from Next (a UK clothing store) was my favourite of hers, as were her very shiny black opaques. She asked me to pick out knickers as well, and I chose her full, control-top style Sloggi briefs. Rachael loved the fact that I liked these ‘mommy-knickers’ more than her skimpier or lacier ones.
“This is a weird thing to say, but if we ever split up I’ve got loads of clothes you can have if you want! I’ll leave them behind for you.”
So, in my living room, with the curtains drawn one late Saturday evening in the summer of 1996 with my new girlfriend’s help, I dressed up as a girl: Knickers, bra (stuffed with tissues), black glossy opaque tights and a black cotton dress. Rachael zipped me up at the back and asked me to walk up and down the room. I did find this special, I must admit.
Rachael enjoyed seeing me get dressed, not with a sense of sexual excitement but out of the novelty of seeing a man wear women’s clothes so willingly and out of choice. After chatting about it briefly she soon realised that I was serious – I knew so much about tights - knowing all about the different styles, denier numbers and materials, as well as a great deal about knickers, skirts and women’s fashions that I Rachael knew that I definitely wasn’t doing this as a joke or novelty. After that, things carried on as they had before:
She sat with me on the sofa and the conversation carried on into the night. After a while I forgot, as much as it’s possible to under the circumstances that I was dressed up at all.
*****
I stayed dressed up for another hour or so. The most exciting part for me wasn’t so much the cross dressing, as I was still a little bit self-conscious and it was all a little sudden and overpowering to be fully dressed just ten minutes after coming out.
The thrill came when Rachael pushed back the hem of my dress with her hand. I watched her eyes, and they moved down to look at my smooth, black shiny knees, and then peer up my skirt. She asked me to lie down opposite her on the sofa; we were lying toe to toe. Before we went to bed and the intimacy of the evening drew us towards the bedroom, Rachael’s foot was lodged between my legs, pulsing gently. (I know what it feels like to have someone go up my skirt!) My excitement gathered, as did hers, leading us to undress. I went upstairs with her – but without the female clothes.
The dress, underwear and tights sat in a guilty heap on the carpet the next morning and neither of us mentioned the cross-dressing again for a few days.
*****
That was pretty much that, and despite this promising start, the mutual dressing didn’t really happen again. There were a few isolated occasions where Rachael asked me if I wanted to have her tights before she threw them out, but I said no because she was offering me her torn or laddered tights. The fact that they weren’t perfect was a little bit of a turn off; I wanted my tights to be as new and as nice as her best ones. I can understand where she was coming from though.
*****
Once, after a horrible day at work I sat in a bit of a daze at home trying to come to terms with things. I was in a bad mood and Rachael seemed keen cheer me up. After disappearing for an hour, she reappeared with a gift for me that she know would lift my spirits. She’d been out to buy me a pair of 40 denier black tights.
I almost cried when she handed them to me. This was one of the most thoughtful things anyone had ever done and I was incredibly grateful. She had given me a big smile before watching me unwrap the package she’d even gift-wrapped for me. It certainly did cheer me up, and she urged me to go and put them on for the night to relax and feel better. It worked!
*****
The planned trip to the transvestite club in Brighton never happened. Rachael mentioned it once or twice on our earlier days together (and I’m pretty sure she did tell her friend Bronwyn about my cross-dressing). There was a discussion about going down for the weekend and visiting the club too for a fun night out.
If Rachael had prompted me and actually organised the weekend, I might well have been brave and gone with her and her friend in full drag. Brighton was miles from my home, and there would be no one there who could possibly recognise me. One afternoon we even went to a local charity shop to buy an outfit for my female alter ego. It seemed that the Brighton weekend was coming very soon.
Or, that had been the plan, but somewhere the idea quietly disappeared. Rachael bought a denim skirt and a top for herself at the charity shop that afternoon and that was all. My feminine self wasn’t to be treated to any clothes from Rachael again, and within a year; we would be living in different countries in the knowledge that we’d never see each other again.
I was sad, but, as I mentioned, there were no tears; and despite an earlier promise that she’d leave her old clothes behind for me, she didn’t. They all went to Canada with her.
It was time for a new start, once again.
