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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Today you can march into a store and buy any lingerie and clothing you want. Tell the clerk it is for you. They will help and advise you, PC rules darling!
 
Today you can march into a store and buy any lingerie and clothing you want. Tell the clerk it is for you. They will help and advise you, PC rules darling!
LOL, no, at my age, those days are past me.. although my wife enjoy buying very cheap outfits from discount stores for me every now and again. For her, the tackier the style or color... the cheaper it looks and cheaper to purchase. Bought me a really bad looking sheer, lime green baby doll nightie for $2 once, its still her fave :)
 
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