The Modern White Boy

I was in the same boat, in my late teens, mid 1980's no internet and was starting to explore sissy sex. So desperately wanted a girlfriend, but lived in a very blue collar, working class suburb... and the girls had no interest at all in effeminate, arty, emo types. Plus I was worried sick, that if I dated one and they discovered I had a tiny cock, if we broke up they'd tell the world. So, in desperation for sexual contact, I accepted an offer from a single middle aged man in our suburb, to have a place to watch porn & masturbate together... and soon enough started having sex with him.

I remember how hard it was to just buy lingerie at department stores and pretending it was for 'my girlfriend' and trying to hurry up with the purchase, before I died of embarrassment or a friend of my parents may see me. The relief I felt when he offered to buy it for me, if I wore it for him was huge, plus he was able to go to x-rated bookstores and buy me ' sissy slut' outfits that i adored.
To be in this situation today, with the internet, would be a game changer and young sissies today would have it much easier, even just to be able to play together, which I would have loved.

I have a few old photos he took of me when I was about 19yo... nothing x rated, but we wanted some to advertise in some swingers mags, and he owned a polaroid camera :) I look at this pic, and wonder if I had have been well hung, did get to date girls.. would I have taken a different road in life, and would I have ended up as a cuckold.

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I used the 'girlfriend ' excuse when buying lingerie. Now I'm trans.
 
I used the 'girlfriend ' excuse when buying lingerie. Now I'm trans.
Same I doubt I would've fooled the middle aged female sales assistant when telling her my 'my girlfriend' was about my size. Lingerie was the easy one, slutty heels were much harder to obtain :(
 
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