Tag Archives: Oliver Wilson-Shaw

Sissy Diary Entry: Oliver The lingerie LOVER

Today’s posting is was submitted by Oliver ~ A secret but not so secret closeted crossdressor. One that adores the look and feel of sexy lingerie. Oliver is dying for the opprotunity to share and discuss his true passion – prancing around in lingerie. Would you like to have a discussion with him?

Oliver’s Twitter: @tart_boy


Hi. I’m Oliver.

I’m actually a straight guy who is married.

I’m exposed quite a bit as you can see from my Twitter profile.

Oliver Wilson-Shaw
Oliver Wilson-Shaw, a sissy crossdressing straight male with an obsession for lingerie.

I would love some more exposure if you can see fit to find the time.

I already have one friend following me on my twitter account but she is in on it.

I would find it such a thrill to log in one day and find a vanilla friend has found out and messaged me privately to ask me what this is all about. I would then be forced to tell them all about my life long lingerie fetish and how it’s crippling my marriage.

I’m happy to have my face exposed and whatever contact details you deem appropriate. I regularly post photos on my twitter from work.

I’ll visit the toilets on a break and take humiliating pictures of my current panties.

I’m not a wannabee cocksucker like a lot of other sissies. It’s the lingerie and the thrill of explosive that get me off.

I have been into lingerie and panties for as long as I can remember. I found a pair of satin frilly tangas when I was about 14.

The feel of them changed my life. As soon as I put them on I knew what I was meant to wear.

I suffered with the shame.for a long time and I couldn’t even count the number of purges of knickers I’ve had in my life from the guilt of wearing something I “shouldn’t”.

I now have an entire draw full of exciting and mostly satin underwear. I only have one or two pairs of boxers for in case I absolutely need them but I wear knickers all the time now.


The urge to purge will hit every sissy out there from time to time, it is not just sissies it hits but it does seem to hit them a bit harder. There is a tinge of guilt that forces you to purge, and then the guilt when you inevitably come back to it. You will ALWAYS come back ~ yes, ALWAYS. It is who you are.

For Oliver Wilson-Shaw, he is a sissy crossdressing straight male with an obsession for lingerie.


Interested in sending in a submission to possibly be posted on Sissy Diaries? Click here (make sure to read/follow the rules or it won’t be posted)