This post will focus on the firsts for cross-dressing, as opposed to the other recent post about relationship things that were firsts. I've actually been planning it for a while but the holidays and ill kiddlies have intervened and so I just haven't got round to it. I have been playing a lot of 1066 though, and maybe something will come of that in time. First I need to finish with my marking.
This was not long after we moved, putting it in around being eleven, and was in the bathroom of the new house. I was sorting some washing to take down to my mother and found a bra. Just a bra. I held it up and wished I could wear it. I didn't. There was a set of shelves in the airing cupboard nearby and I remember that I wished I could use it as a cage about the same time. The two events are pretty closely connected in my mind anyway. Make of that what you will.
Link of dressing with sexual acts:
|On of those of which I speak was shorter than this. The top|
of the pink band short. And it was green, cream and pink
stripes. With flowers. A frill around the edge.
I sometimes wonder what became of those pinnies. I was very careful with them, I never marked them or stained them in any way and always managed to replace them whence they came as they came out. Autistic traits can help when trying to keep sexual acts secret I find.
Time I wore knickers:
|Except that the knickers were white.|
And brand new.
That's why I checked first to make sure that the
whole thing was a fake. Well, that and other
I rescued them. Wore them a few more times and threw them out again. I e-mailed the Chaplain as if from somewhere else with my first ever web-mail address and asked about religion and cross-dressing. I got a non-answer that Jesus was still supportive of me and didn't care much for the cross-dressing (as in he didn't care, not that it was wrong or right). I rescued the knickers again. They sat in a drawer. I think I wore them a few more times and then I threw them out again. I think I eventually made sure I threw out some food on top of them and took the bin bag out on the same evening to prevent me rescuing them a third time.
Time I wore a skirt:
|See what I mean?|
It was just to the knee and had a short slit
up the back.
Time I wore a mini-dress:
Not long after I moved into my second flat I ordered a dress through eBay. I wore it for the first time the second time I invited Toby back and wore it to show her. To show her what, exactly, I have never been able to explain. She wasn't taken aback and she wasn't inflamed. If anything she seemed dismissive. Indeed, as the time wore on she was actually, looking back, very uncomfortable. I should have picked up on that I guess. It was before her birthday. It cost a fiver, as it happens. A blue (dark navy) with a wide white stripe asymmetrically placed vertically. To the right if I recall. It was rather short, falling well above the knee and not far below my crotch. Far enough that I could hang free and not show but not much further. It was the one I wore out the second time I went out dressed. I liked it. I got rid of it in the most recent purge of my stuff to try and impress Tilly. The time she wasn't impressed and didn't care one way or the other.
Oh, yes, I was 24 and it was just after New Year.
Time I bought knickers:
Summer. I had spent the night at a friend's without meaning to (I had driven there and ended up having one or two pints - or the equivalent, I can't remember, the point was I wasn't driving). So I had not prepared. Toby and I weren't going out but she loaned me a t-shirt to sleep in and had spent the evening complimenting me and saying how good I would look in a dress. I had suggested that I would be interested in that in a very roundabout way. A week afterward I bought a pack of five hi-leg knickers from Morrisons. £4. I was still 23 at this point. They were black. I wore them a lot, but only after work.
Time I wore a dress:
I was just 24. Just. Toby and I skipped a party at a friend of a friend's and went to her room. I later learned it was her wedding dress. It was purple, shiny fabric and fell well past my feet. Corset effect ribbon ties did it up and it had a plunging neckline. It felt perfect. It looked pretty good too. Not on me. I didn't exactly make it look good. Mind you, can't deny the fact that I enjoyed wearing it. Over all too quickly due to my fear of being seen, caught or... something. Toby was very supportive, very complimentary and seemed to enjoy the experience.
With Toby. I wore her pink combat trousers, rainbow hooped cardigan (zipped) and a pair of handcuffs. Lovely experience. She massaged my back with oils in the evening. I passed up the opportunity to have her 'help' in the toilet. I am, and was, a dick. Still 24, after the first time in a skirt.
Time imagining myself female:
Exact date unknown. I used toilet roll to tie bows on my wrists, ankles and neck. It felt divine. I was under the bedclothes so that if my parents (just my mother?) checked they wouldn't see anything. This dates it, I know. It was the first time I'd stayed up past 11pm specifically to masturbate. It must have been a school night because I remember being worried about the effect of the late night on my performance in the morning. I mustn't have been older than 13 but I could have been as young as eleven. At this stage I didn't always ejaculate when I masturbated, didn't even know that was what one did if I'm honest as I didn't link anything I was doing to actual sex in any way. I did this time. I was quite upset about that. I managed to clean most of it up. At this stage I didn't do it much on my bed.
I don't think I was aware that ejaculation was sperm. God knows what I thought it was or what it was doing. I didn't feel that it was 'wrong' or anything, just didn't connect it at all with any of the sexual education I'd had. I mean, I knew emissions were 'normal' and hated the fact that it smelt but beyond that it was just something of mild interest. My poor mother must have known I was up to something as she was still doing all the washing. Yeah, this must have been around the age of twelve then. Okay, apparently the imagining myself as the opposite gender wasn't even the most diverting part of this particular experience. It didn't 'turn me on' so much as it was part of what I was doing at the time.