What do you think lead to you becoming a crossdresser.
For me…I used to chat with mum and watch her while she put her makeup on, and one day, when she left for work, leaving a lipstick open in frontvof me, I tried it on.
I then went in her wardrobe and tried her denim skirt on.
She occasionally used to ask if I liked how her makeup looked too!
Also, at a young age…Mum buying, in error a girl’s blouse, thinking it was a boy’s, when I was young and asking me if I would wear it anyway. I did, but attached no importance to it.
I think the start of it for me was when I was very young my sister and I had a dressing up box and there was a red dress in there which somehow always found its way onto me. I don’t know whether it was me that wanted it on or if I was forced to put it on by my sister but I must’ve liked it cos I love wearing anything feminine now.
I’ve crossdressed for so long it is hard to remember but we too had a dressing up box too and there was a lovely peach dress that i loved and wore a lot.Then when my friend admitted he loved wearing stockings which he bought from his parents shop i just had to try myself.I bought a suspender belt and stockings from there which he got for me and when i got home with everyone out for the evening i tried them on.I think i wanked myself off three or four times that evening before my family arrived back home and from then on i was totally hooked.I dress now both for a sexual thing but also because it feels so lovely and also natural for me.
It happened very late in life for me and came about very gradually.
We entered into a male chastity relationship about 5 years ago which gradually became a domme/sub dynamic.
My subservience, coupled with my wife’s Parkinsons disease meant that I was taking on all the traditional female roles in terms of housekeeping and daily chores. Sexually she stopped being penetrated vaginally and anally and began to use toys to satisfy herself. At the same time she began pegging me regularly and that is now my favoured route to sexual satisfaction. Domestically and sexually then our roles became reversed.
Since I was now effectively the female partner in our relationships I began wearing knickers and a gaff (fake vagina) covering my penis 24/7. Since then I have moved on to stockings, suspenders, suspender tights and in the last couple of weeks I have begun to wear women’s bras (mens bras are awful). I also remove all my body hair from the neck down for a more feminine appearance.
My mum used to regularly buy stuff from the catalogues where you pay so much each week back in the 70’s/80’s… I was fascinated by the lingerie sections, women wearing basques, suspenders, stockings etc… I never though anything of it…
In the mid 80’s while feigning illness to get out of school and being left home alone i felt the urge to try my sisters communion dress… It was far too small but i tried anyway and loved it.
After that any chance i got i would try on my mums or older sisters clothes and my dressing has continued ever since!!
The closest I’ve ever got to cross dressing is trying to waddle in my mums heels as a toddler and running around the house pinging my nana’s giant bra and knickers about while she was on holiday, until one day saw there was a stain in one of them and that put an end to that!
I think the first time I tried on a girlfriend’s panties , I was so turned on that from then on I was hooked . Over many years I gradually worked my way up to my present level . I wear sexy women undergarments around the house only . With the exception of panties . The feeling of lace or silky panties on my hair free cock and balls is just too nice . For Halloween many years ago my wife dressed me up in a sexy blue dress , " made me " wear her lace stockings and panties . Then did my makeup . She and I thought I looked pretty good . Totally freaked out my neighbor . My wife said it was because I looked 5 times hotter than his wife . As a foot note , when we got home it was a wild night of sex .
I wouldn’t necessarily describe myself as a crossdresser in the fullest sense, but I do very much get a thrill from wearing certain items of female clothing - panties, thongs etc, stockings and suspenders, baby dolls, bodies.
It is difficult to pinpoint what spurred this interest initially. It has definitely been there for a long time and I do remember trying on a few things some years ago . Also, images of women’s lingerie in magazines etc. also held my interest, as @ajs72 similarly mentions. I guess that some men, to a greater or lesser extent, have a feminine side to them and this will no doubt play a part.
It is only very recently though that I have been actively pursuing this interest and have begun purchasing items of female lingerie. I am finding it a very exhilarating experience I have to say. I find it hugely exciting knowing that I am wearing items that are also being worn by women with the purpose of looking and feeling sexy. Everyone needs some sexy lingerie in their life!
I definitely have an underwear fetish love seeing women In stockings and so on …… so after some time I’ve stuck a pair of stockings on and love to feel to so it’s gone from there
Although I wouldn’t call myself a crossdresser at all more a man trying to look sexy in sexy underwear
I thought of this song this morning and thought you all might enjoy it . It is over 10 years old , done by one of our local Dee Jays . Note he put out some great Christmas songs . Hope you enjoy this .
I’ve not really paid attention to this thread but it’s interesting to hear how you all got into it. Not really the same for women, I love wearing sexy lingerie and a very occassional, glammed up, night out with the dress and killer heels but 99% of the time I’m sans makeup, on the farm with wellies and work jeans… wouldn’t really class it as cross dressing though and I’m still in woman’s pants and bra underneath.
I’ve never heard of men’s bras specifically. Are they practicle for keeping larger moobs in check or fashion accessories? What makes them awful?
Also, @Oldman , I hope you don’t mind, I’ve edited your post ever so slightly so that the song plays in situ rather than having to link through to YouTube. Great version of a classic!
