All Comments on 'What Might Have Been'

You have to be a special type of "gurl" to carry this sort of thing off convincingly. My late cuckold looked dreadful on the occasions that I dressed him, but he adored the humiliation, and almost inevitably leaked into the panties I'd put on him, despite also wearing a cock lock.

My current sissy slut is far more convincing dressed, so I have to devise scenarios in which 'she' could possibly be outed. I've only done so twice up to know, and self isolation and the Covid pandemic have restricted our play time together, but as someone famous once said, "all things must pass" and hopefully, we'll soon be able to resume our interaction.

This 'real life' story is a refreshing change from a lot of the fiction here. I enjoyed it. Thanks for sharing it DeanaBard.

Great story, definitely can imagine that scenario playing out - only I hope this fictional character gets a second chance to find out what it would feel like! :) While he ends by wondering what might have been, there's still time!

[Sorry to hear about your dear friend's brother though - hope he had a happy life at least]