Dear Carole -
Remember all my carefully-laid plans about not getting involved with another woman for a while? Scratch them!
As you know, I split with my partner in mid-September, and as time was short before my 'window of opportunity' for a holiday (basically late October), I decided to spend two weeks at the same place that we'd been to as a couple last year - it's an all-inclusive resort in Grenada called La Source. It also had the advantage that I knew the place and the staff, and the fact that they cater for singles (even though to a limited extent), so I wouldn't be completely thrown in at the deep end.
Being on something of a mission - as you'd expect - I'd painted all my nails pearlescent pink before leaving home. Naturally, many of the other guests in the resort noticed this, and soon began asking the staff what I was up to. Some even asked if I was gay. Well, as I already knew most of the staff from last year, I'd confided in a number of them as soon as I'd arrived, and they all thought it was rather fun. In fact, I'd taken Sally's photo album with me for this very purpose! They were therefore able to fend off inquisitive questions on my behalf, and a few of the braver guests even came and spoke to me directly, which was nice.
As it happened, last year, I'd had some hassle from the restaurant staff for wearing tailored shorts to dinner. I'd ignored their request to wear trousers, claiming that it was discrimination, and adding that, if shorts were good enough for corporate Britain, then they're certainly good enough for a holiday resort. However, this year, I decided to take their "casual elegant" dress code into consideration, and from day five, at the suggestion of a number of the staff and some of the guests whom I'd got to know, I wore a long skirt instead. When the initial fascination with this had died down, I was persuaded to wear my high-heeled strappy sandals as well, although I don't think anyone was unduly surprised at anything I did by this time! Curiously, the restaurant staff didn't seem to have a problem with it either - they'd probably given me up as a lost cause! However, there was one macho-moron critic who said that I looked "unmasculine", and that it was "suspect" for a guy to behave this way - so I publicly embarrassed him, then re-painted my nails bright blue, and took every opportunity to openly flirt with his wife for the rest of the holiday. I don't suppose he'll try that again in a hurry! In fact, it was one evening when I was wearing all my femme clothes that I got the chance to play the piano with a reggae band in the bar - their name was 'Minimum Wage' (a reflection on what they were paid, apparently), and the drummer was the resort owner, Leon, so I gather from that that I was totally accepted by the people who matter. But there was one other thing which occurred as a direct result of how I was dressed - it certainly hadn't been on my list of things to do ......
They have a 'singles' table in the resort dining room (for dinner only) which my partner and I had sat at last year because the people were more varied and interesting. I also sat there most evenings this year, although several guests were interested in my reasons for wearing a skirt, and I was occasionally invited to sit elsewhere. Meanwhile during the daytime, I'd completed my Open Water Scuba Diving course (which I specifically wanted to do this year) on 29th October, and subsequently decided that I was probably ready to go home - maybe 14 days had been a bit too long? Then the next day, a youngish woman and an older man flew in from the US and sat at the singles table with me and a couple of the resort staff. The man (Dick) turned out to be a closet gay, and, having seen the way I was dressed - and also having had a look through Sally's photo album - he felt free enough to 'come out' to me, which was nice. He subsequently also confided in the woman (Kim), so I must've gotten my message across just a bit. That evening was fun - the three of us had a common interest in classical music, so there was plenty to talk about. But the next evening, a retired European Studies professor from England joined us, and proceeded to bore us stupid with tales of where he'd been and what he'd done. Dick was interested in comparing notes, so Kim went to bed, and I went into the bar.
At lunch the following day, I saw Kim sitting on her own, so I asked to join her. Amazingly, we spent more than two hours talking about all sorts of things, and made arrangements to sit together for dinner to avoid a repeat of the previous ghastly evening! At dinner, we again talked non-stop for nearly three hours, by which time it'd become obvious to us both that there was a strong sexual chemistry between us. Now, I'd already told Kim my situation - namely that I was recently separated, and didn't want to begin another serious relationship. She was currently trying to rekindle a dying relationship of her own back home, and we'd discussed the possibility of spending the night together for comfort and companionship, but remaining just friends. I'd really believed it was possible ...... By now, the restaurant staff were getting agitated about wanting to shut the place up and go home, so Kim and I went for a walk, ending up back at her room, sitting face to face on the bed wondering what to do. Well, it was obvious, really - we just hadn't been brave enough to face it ......
After that night, we both felt so good at being loved (or even just lusted over!) that we took every available opportunity we could to be together over the next two days until I had to leave. Of course, everyone had noticed me in my skirts, with my painted nails, etc., and so gossip about us spread round the resort like wildfire! Kim liked being the focus of attention too, and the resort staff were really pleased that the singles table had finally brought two people together - I suspect they already had us married off! But according to staff members who confided in us, many of the male guests (and especially my favourite critic) couldn't handle the fact that an attractive woman like Kim would want to be seen with (never mind want to sleep with) a man who looked so femme - although I know that it was this, together with my openness, honesty, and courage to be what I wanted to be, which had first attracted me to her. Such a positive reaction to something which most people find slightly dubious counts for a hell of a lot in my book; it's just such a pity that we met so late on in my holiday!
Kim is 38, works as a professional musician, and lives in a part of New Jersey where my unconventional lifestyle wouldn't be welcome. We've therefore made tentative plans for her to come and stay with me for a week in the Spring - we want to play some music together (obviously), go to a classical concert, a jazz club, a tranny club, and anywhere else which takes our fancy. She also wants us to "explore cross-dressing together" - I'm not sure what she means by that, but it sounds good anyway! If all goes well, maybe we'll arrange to meet up on holiday again next year. Then who knows? In any event, we've swapped phone numbers, e-mail addresses, and home addresses, and we'll definitely keep in touch.
This is the sort of stuff that fairy tales are made of, isn't it? I'm tempted to believe that there really is someone up there smiling down on me ......
From a personal letter.