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On ThePornDude Hall-of-Fame
Felt cute, might delete. But I can’t.
I went through a sissy phase when I was younger. I came across some sissy porn online and before I knew it I was putting on makeup and clothes.
Following the instructions in videos I decided to get a dildo and would take pictures and videos of myself posing with it in my ass. I even posted a few to some sites to see the comments
Once this phase was over I settled down with a girlfriend, never spoke of it and I’m happily with her. However, if I ever Google image search any Sissy porn Captions I’ll see this picture of younger me all made up in nice lingerie with a massive dildo in my ass. There are obviously copies of it as there are a few different versions with different captions.
There is no way my girl would search for it or even know it was me if she did. But I wish I hadn’t posted it back then as it’s out there now.
Have you tried mentioning it to her? You'd be surprised how many women are into having a crossdressing boyfriend. I'm a crossdresser myself and I always seem to find 'em.
If it helps I reckon I’ve probably jerked off and cum to (or even on) your picture many times. If you ever want to make another, let me know.