undefinedI have been a cross-dresser since I was 9 years old. Years and years of dressing up in private, feeling ashamed whilst dressing in women's/girls clothes; feeling humiliated athe tought of being caught or seen whilst sexually sroused at how I was dressed have probably caused me to associate humiliation and sexual arousal.
My early efforts at going out dressed left a lot to be desired, with lots of sniggers, laughs and bemused looks. As I got better at dressing, the looks, the sniggers and the embarassment began to fade.
Eventually I came to realise that the embarassment and the taboo of being picked as a man or boy in womens' clothes was as much, if sometimes not more, the cause of turn on than the clothes and makeup themselves.
So started to do things that made it obvious I was a sissy male.
At first I started going out shopping and to gay bars with pantyhose and no socks under my trousers and light pink nail polish. Very little reaction - I might as well not have bothered.
I summoned the courage to take progessively greater risks. Addimg light touches of makeup and some girly jewellery. I sometimes left my shirt unbuttoned enough to show of my satin and lace bra or camisole. I began to get at least a few smirks and knowing glances as I presented my purchases of female items to the shop assistants.
Once, when I was about 19, I wore a pair of tan pantyhose and a diamante ankle bracelet into a womens' shoe shop, under a pair of womens' jeans with a white loose fitting T-shirt. My white bra was vivble if you looked, but not obvious.
An attractive sales assistant in her 20's asked if she could help me. I asked her for a pair of taupe boots and white 4.5 inch stiletto courts in a size 10.
She looked at me a little perplexed and then smiled and said she would have a look. She came out with a box of each.
Here was the telling moment! Would I buy them with the possibility of them being the wrong size, or would I have the courage to do waht I really wanted to do - try thme on.
I gulped and stared at her for a few moments and then indicated that they were for me and asked if I could try them on. There. I'd done it. I stood there bright red in the face, becoming very aroused in my panties as she politely smiled and motioned me towards a seat. She said she get get me a stocking to try them on with. I lifted my left trouser leg, revealing my stockinged ankle and ankle bracelet and said quietly and ashamedly that that wouldn't be necessary.
She smiled again and complemented me on my ankle bracelet. I was in seventh heaven. As she helped me zip up the boots, her fingers gently brushed my stockinged ankles. I almost erupted there and then.
It was also highly embarassing as I paraded around the store on womens high heeld courts and the boots, an obvious male,with other women watching on bemusedly.
I bought both, thanked the assistant and let the store.
Next I started to take further risks. I started going shopping and out to gay bars dressed in white or powder blue jogging shorts and matching t-shirt or sportshirt with tan pantyhose and light blue panties underneath - usually with light pink painted nails and light mascara and light pink lipstick.
My first step into a crowded shopping mall with my leg very visibly encased in tan pantyhose had me weak at the knees
Later I graduated to wearing the same outfit with ultra shimmery lycra pantyhose, Wolford Neon 40's. They were much more noticeable - especially in the sunlight
I would delight in people, especially young, attractive females remarking things like "Hey there's a guy wearing pantyhose" or somewhat more rarely schoolgirls or boys, being a little less sensitive or discreet, would say quite loudly = look at that sissy in pantyhose. I wouls spend hours walking around shopping malls, catching trains going to bars like that. I loved sitting in outdoor malls with the sun highlighting the shimmery hose. I loved going into stores and trying on womens shoes and boots. The more sniggers and stares; the more comments the better.
I went on to wearing darker, more noticeable pantyhose, and even black fishnets with tight denim shorts or even a kilt or a skirt with womens boots and shoes - but that's a story for another day
Originally Posted by Tesstv
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