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The Opportunity

a journey from gentle travestism to anal slut




I suppose looking back, that my childhood was to blame, that is if there was any real blame to be attached. It could have just been my inherited genes so I can happily blame my mother and father for being the smallest in the class, but I somehow also got left out when the popularity genes were issued, I became a loner and spent far too much time in my own company for any real good to come of it.

I loved the movies, the actresses were goddesses with their beautiful make-up and cultured coiffure, the long golden limbs and neatly manicured nails and toes   I watched opened mouthed in admiration accompanied by my own obligatory little stiffy.


Anyway I’d made it finally to my own living space, my own bijou, one bedroom apartment.

There was no need to hide anymore, no sneaky visits to my sisters’ underwear drawer and make-up bag, no more squalid stolen minutes with part of me on the alert for the sound of keys in the latch and unexpected footsteps.


I thought I had been very brave it was the one job I wasn’t happy with doing myself, I had attended a nail parlour in a town far enough away, that I didn’t care whether or not they believed story about my part that required long nails in the charity Christmas panto, in fact the young girl had probably guessed when I chose the more subtle coral pink varnish rather than the garish bright red tarts gloss that would have been more akin to my non-existent role in the non-existent panto


I was home, my nails done, a pair of strappy high heels purchased, using the same excuse, from a local branch of Dolcis, size seven the largest size they sold but perfect for me and no need to use any of the specialist London transformation shops, yes I read all the adverts over and over again. Me and my little stiffy. I loved shoe shopping, I loved the variety. The pure sex of the stiletto heels, the knee-high shiny black leather boots, the party sandals. Please don’t misunderstand I wasn’t gay I just wished I could have breasts and wear make-up and I wanted some sex other than by masturbation.


I was in heaven, I’d grown my hair long, dark brown chestnut hair to my shoulders, clean & shiny, centre parted. I depilated all my body hair, applied a fake tan and had painted my toe nails. I was five six, five nine in my stilettos, nine stone and for the first time in my life I was going to be a woman,



I applied a thin veneer of foundation, lipstick and mascara and paraded myself shamelessly in front of the full-length mirror, my tiny cock and balls free of any hair, my nipples erect and sensitive. My long tanned lightly muscled legs balanced on the heels as a tribute to the movie stars. I wore a thin very short tee-shirt dress, no panties to complete the effect.


The doorbell rang, I jumped!


I knew who it was. I answered quickly.


The girl was petite quite tiny, in fact. She was wearing a short pleated skirt and a tiny tee shirt displaying her navel and that she was bra-less, her nipples poking through the thin fabric.


I’m not proud that I’d hired an escort, but you have to understand I was 28 and still a virgin I dealt with the cash side of things and had explained on the phone that I was a transvestite, there I’ve said it! It’s such an ugly word and Dani was happy to play along


She let me kiss her ………….softly, slowly, gently, tenderly, we touched tongues, the sweet wetness of her mouth


I wanted to lick and kiss her pussy more than anything else, we removed her clothing, stripped the tiny g string from her to reveal the sweetest shaven pussy, I wanted one of those!

I kissed her moist folds finding her hidden tiny bud, with a gentle investigatory thrust of my tongue . “Please no fingers” she said as I continued   to massage her slippery sex with the tip of my tongue, Dani began to respond, gently bucking her hips to the rhythm of my caresses. She moved her head and found my smooth balls with the warmth of her tongue , lapping gently at my tiny manhood,


  I came!!              Shit!!        Double Shit!!                 I came so fast, one big gush, showered the poor girl just one surge of warmth through my loins


She pulled her head away so fast, it was all over…………….



After that disaster, I was still a virgin


but Dani became my friend.


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