Words of warning and welcome:

This is very much my blog, so don't be surprised if this doesn't follow accepted patterns and norms. Obviously it started out as a blog about my cross-dressing but it has developed a great deal since then. It is a place where I can be anonymous and honest, and I appreciate that.

It will deal with many things and new readers would do well to check out the New Readers' Page above this and the tag down there on the right. Although there's nothing too bad in here there will be adult language, so be careful. If you think this needs a greater control, please let me know. Thank you!

Saturday, 19 April 2014


I think I have documented pretty much every aspect of my history now, but it's all over the place and doesn't make for easy reading. So, far be it from me to remain difficult, I thought I'd try putting everything in one place. Not sure if this counts as TMI or not, so I haven't listed it as such, nevertheless, I have included a line break to save the eyes of those visitors who dislike walls of text.

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.


Time I held up female clothes to myself and wished I could wear them:
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.
Bizarrely, this may have two points. Around my GCSEs, study leave, so I would have been 15. I found a stash of very short and far from functional pinnies. Kinda like really small aprons. These were all obviously home made and had been made sometime in the late seventies or very early eighties if the fabric was any indication. They were beneath the tea towels in the kitchen. This would have been about two years after my father left, give or take, and it was clear that these had not been used at least in that time. I forget what I was doing to find them but when study leave rolled around and I had the house to myself for six or seven hours at a time I was pretty obsessed with them. One of them was a floral design fabric and very short, if you tied it above the waist it barely reached far enough to be decent, if you know what I mean. No way this was a functional garment. Probably something for my mother.

Of course I wore it. Many times. Sometimes, most times, just the pinny. I masturbated in it a lot. I used string to create handcuffs or a leash. I would tie myself to the taps above the sink in the kitchen to do the dishes and would listen to Missing whilst doing so. I think this may also count as the first time I masturbated outside of a toilet as it was in the kitchen. Luckily the floor was linoleum. At some point in that long summer I took it out to the shed and attached a ring hook to the ceiling in there, tied my hands behind my back and attached a string leash to the hook. It was almost too effective as I managed to do it in such a way that I couldn't untighten the slip knots on my wrists and spent a most exciting/terrifying twenty minutes trying to get free. Of course I managed. It didn't diminish the feeling.

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
University. I was barely eighteen. My floor mates had decided to test my resolve and ardour for my very new girlfriend by sending a fake note that was accompanied by a single red rose and a scented pair of knickers that I now know was a thong. I did not know that then. After ascertaining that this was fake (and trust me, I checked, the floor mates never admitted it) I threw away the rose. I kept the note a while, because it too was scented, and then discarded it. I kept the knickers. In the run up to the Christmas holidays I wore them for the first time. I did this maybe five times before I masturbated in them. Then I wore them to the toilet and masturbated there (public stalls so a bit of a risk - well, no, that's wrong. I think I went to the single loo round the corner). Then I threw them out.

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.
Birthday party for Toby. Part of a schoolgirl outfit attempt. I say attempt because the skirt was pretty professional and the blouse a bit grown up for a schoolgirl effect. I also wore a bra for the first time (having bought it specially for the occasion) and tights (also specially bought) with make up and a wig. I loved the mascara in particular. I did not look good. The sight of myself in a mirror was not alluring. But the feeling was nice. I also wore Toby's glasses for most of the night to the point where my vision was blurry without them. I enjoyed that sensation the most on a night that was full of nice sensations. I was about 24.

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.

Day dressed:
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.

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