Sissy Whiteboys

I started thinking about my own sissy transformation when I had to go and start organizing my old "dirty" file pictures. I have a folder full of the pics I use on Grindr and here and it's gotten full over the years. my first gay hookup was back in 2014 and I found the pics I used in college on CRAIGSLIST of all places. its wild to look at the pics I posted then when I was trying to find a guy. Jockstraps, cocks, naked ass.....

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To now. Sissified, chastity whore. the transformation happened slowly, but im so happy it did.

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I started thinking about my own sissy transformation when I had to go and start organizing my old "dirty" file pictures. I have a folder full of the pics I use on Grindr and here and it's gotten full over the years. my first gay hookup was back in 2014 and I found the pics I used in college on CRAIGSLIST of all places. its wild to look at the pics I posted then when I was trying to find a guy. Jockstraps, cocks, naked ass.....

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To now. Sissified, chastity whore. the transformation happened slowly, but im so happy it did.

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You look amazing
 
I started thinking about my own sissy transformation when I had to go and start organizing my old "dirty" file pictures. I have a folder full of the pics I use on Grindr and here and it's gotten full over the years. my first gay hookup was back in 2014 and I found the pics I used in college on CRAIGSLIST of all places. its wild to look at the pics I posted then when I was trying to find a guy. Jockstraps, cocks, naked ass.....

View attachment 6294463View attachment 6294464View attachment 6294465View attachment 6294466


To now. Sissified, chastity whore. the transformation happened slowly, but im so happy it did.

View attachment 6294479View attachment 6294481View attachment 6294482View attachment 6294483View attachment 6294485
no cage?
 


I was slow to finding the joys of chastity. I didn't see the point at first, but that is like so many other things in the sissy journey. I didn't like stockings, then loved them. Didn't see the point in wearing a bra, now I love it. At various points, I said "never a wig, never a dress, never heels, never jewelry, never temp tattoos, etc" but now I love all of those things.

For chastity, it was a girl that pegged me that introduced me to it. I remember telling her that I would NEVER do it, then she just convinced me to try it. I was literally hooked the minute I put it on myself. I remember seeing how small it kept me, and comparing it to one of my dildos when I was by myself. now I can't imagine fucking without it. its VERY rare I go without chastity now and I have to be in a very special mood with a guy who makes me feel like I don't need it.

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Me white sissyboy
 

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The topic is often discussed in the cuckolding style. Final humiliation, submission to black men. True or a false image of the Whiteboys?
True. I want my final submission to be something like that, dressed like a slut and bent over ready for a Black Stud to turn me into his BBC Slut.
:blackheart: :lips::blackheart:
 

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The topic is often discussed in the cuckolding style. Final humiliation, submission to black men. True or a false image of the Whiteboys?
Gorgeous.. stunning artwork. 😍
I wonder what the reactions are in the hospital, doctors clinic, physio or other places where stripping to underwear and exposing this beautiful truth would be 🤷🏻☺️
 
I am a 53 year old cuckold whose wife turned into a sissy! I am so thankful for her guidance and willingness to train me to be a completely submissive sissy.
 

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