by
sleeper
@ 07/10/2005 - 09:45:28
[Retrospective: January 2005] - This story was written in February for posting on a different site.
I've found a quiet moment to write about last Saturday, my first outing as Penny, something I have dreamed about since I was 10 years old.
Initially, when G invited me to the Hastings do, I declined. The reason I gave was that I had the worries of shutting down my company to deal with! Anyway, after some thought, it became clear to me that this was mainly cowardice so I decided that this would be a good way to take my mind off business problems. Well the combined effect on my sleep of both issues was catastrophic! During the entire week before the fateful day, I must have slept a total of about 20 hours, all of which did nothing for my looks (dire at the best of times). 
My wife and I talked a little about my trip, but not about the detail, more about my need to go etc. I gave her the final sanction, but even though she is deeply troubled by my cross-dressing, she didn't use it. Bless that sweet woman!
Well, I soon realised how much preparation I had to do for a real night out. I made a list of things I had to get, things I had to take, times that were available to do certain things (like shave my legs again). What a palaver! I'm beginning to understand why so many women have trouble with punctuality.
Since I'd never been out before, I didn't have a handbag. I've never put nail varnish on, so I had to buy some. Planning ahead for the return home, I discovered that my wife had run out of NV remover. What a good job I checked, otherwise I would have had to spend Sunday with my hands in gloves to avoid awkward questions from the children!
Anyway, the fateful hour arrived, and after making tea for the children I slipped away, taking the keys to the office where I was to change. Stupidly, I thought 40 minutes would be ample to get dressed and put on my face, but I needed every last second of it! Since I have only recently "come out", and the storage for my kit is still under a creaky floorboard (no kidding), my options were limited to two outfits. The dress is too much of a party thing and would have meant shaving under my arms, a step too far at this stage. I opted for the short black skirt (BHS) which I love and the black top from Next. For underwear, I chose a black "Comfort fit", lace-trimmed Charnos body which is delicious to slink into and helps keep things in control.
When I opened the new pair of black, hold-up stockings I had bought specially for the occasion, I was SO disappointed. I hadn't been able to find the usual brand and these weren't up to the standard. Luckily I had packed a pair of the freshly laundered ones which turned out to be in good condition, so I used them, smoothing the lined skirt down over my stocking-tops. Sigh.
Makeup wasn't too bad until I got to the eyeliner and I very nearly blinded myself I was shaking so badly! I was also in trouble trying to paint my nails for the first time ever. By now I only had 5 minutes before I had to set off and I knew that it took at least 5 minutes for the varnish to dry. This meant I had precisely 0 seconds to do them all. The tip of the brush was shaking like a palm-tree in a hurricane, and I came close to up-ending the whole bottle all over my skirt. Somehow I managed it with minus 5 minutes to spare! Then, with nail varnish still not quite set, I tried to put everyting away in my carry-case and a couple of things into the tiny handbag I got from a charity shop. Then came a moment of pure girly panic as I couldn't find the keys, and then my phone, and then I lost my keys again and very nearly burst into tears. :-)
Finally, I collected my wits and set off for the rendezvous at a pace that, whilst fast, recognised that now was not a good time to be involved in an RTA or get caught for speeding! I sensibly opted not to wear my Bally shoes while driving, they are very femme and only a demure 2 inch heel, but a size too small. OK for a while, but not for a serious night out.
I was only about 4 minutes late arriving at the pickup point for G and A. I slipped into my shoes, stepped onto the street for my first time ever as a woman. Giddy with the thrill of it all, I click-clacked up the drive and knocked on the door. It opened, and then, for the first time ever, someone sees Penny. Wow, heady stuff. It's C, the partner (genetic girl) of A and later on I learned that she made some complimentary remarks about me...glow, glow! The two other girls, G and A are soon ready and we set off for Hastings. G and A are marvelous! They're so naturally feminine and they put me at ease.
Once we arrive, there's a short walk from the car to the house in my heels...oh what joy! Inside there's a great finger buffet with booze for some, and coffee and orange juice for me as I'm the driver. Probably just as well, because I'm on nature's high anyway. The event was well attended, and since there were loads of conversations going on, it was only natural for me to get chatting too.
I actually love talking to people, even total strangers, and whilst it would be a lie to say I felt totally at ease (my short skirt made absolutely sure of that as I had to keep tugging it into a more decent position), I did manage to get into a couple of good discussions. E, is a single, very convincing TV, M is a lovely post-op TS and C is a cheerful married girl. C had an awesome cleavage that just made my jaw drop, so I was delighted when she took me under her wing and was very sisterly and full of advice, even giving me a couple of items from her wardrobe which didn't fit her. We went upstairs and I tried one of them on there and then. While we were there, one of the hostesses, K, looked in and gave me some advice on my wig (which to be honest, I struggle with) helping to make it look more natural!
G, A and I headed home at around midnight and all in all it was a wonderful evening. Even if I still felt a teensy bit like an outsider, I know that the next time, I'll just drop straight into the fun of it all. After all, there are 28 years of pent-up femininity inside me waiting for release!
I got home just after 1:30am and rushed into the house just in case the neighbours were all watching, waiting to see me! I rememebered to bring in the big bouquet of flowers I bought the previous day for my wife. 20 minutes of makeup removal and I was tucked up in bed beside my darling wife by 2am....and slept for about 3 hours!