So when did it happen, sissy?

[sirtheocean]

Wow this was really sexy and hit close to home. I'm still not 100% sure I'm a sissy but I've definitely recently started to enjoy the feeling of being emasculated. That humiliation any guy feels for not being 'man enough' has started to cross into my sexual desires.

I was checking out a hot gym girl's instagram and saw a pic with her boyfriend grabbing her ass. This guy was just a huge muscle bound stud, the kind you can't compete with, and I thought 'wow now there's a real man'. I looked for a few more pics with him in when I was suddenly like 'wait, am I jealous of him or of her '.

These feelings of not being 'man enough' led to me trying on a pair of my girlfriends panties and I could not believe how my butt looked in them. It could have been a girl's butt! It was one thing to feel that I wasn't a man but to feel sexy like a girl was a whole new level of emasculation. So that's maybe when it happened and I thought 'omg am I actually a sissy?'

It sounds like you opened the sissy pandora's box with the instagram, and then trying on panties and realizing you looked good in them. Most of the callers that I talk to that are into feminization, have admitted to feeling that mix of humiliation and excitement, to wearing panties and women's clothing. Thank you for sharing

Yes Mistress a sissy pandora's box feels about the right way to put it. As a straight guy, I think we all still know a stud when we see one. But almost giving into that feeling of inferiority to him, imagining my girl posing with him, and enjoying how it felt was definitely a pandora's box moment.

Now that box has led to me dressed up in my girl's lingerie imagining myself posing with him

[Sissy_Carter]

Thank you for the question. For me it was a very gradual realization. I was a late bloomer, not hitting puberty until after all the other guys. And by then I was already into digital exploration of myself. I would "masturbate" until I was leaking fluid and I thought that was normal. Then came the panties, stolen from my friends cupcake. My first pair were satin and very pink with frill trim along the top. My cupcake caught me wearing them once. Over the years I've tried to embrace the masculine side, but have learned that is a role I play, to fit into what others think of me. A few years ago I stumbled upon some sissy captions and fell in love. I wish I had not tried to fight it so long. But I can take these steps now even though I've known my whole life I'm not like other guys.

[EnchantrixRachel]

Thank you for the question. For me it was a very gradual realization. I was a late bloomer, not hitting puberty until after all the other guys. And by then I was already into digital exploration of myself. I would "masturbate" until I was leaking fluid and I thought that was normal. Then came the panties, stolen from my friends cupcake. My first pair were satin and very pink with frill trim along the top. My cupcake caught me wearing them once. Over the years I've tried to embrace the masculine side, but have learned that is a role I play, to fit into what others think of me. A few years ago I stumbled upon some sissy captions and fell in love. I wish I had not tried to fight it so long. But I can take these steps now even though I've known my whole life I'm not like other guys.

Such a weight is lifted off when W/e embrace who W/e are!

[Sissy_Carter]

Thank you, Enchantrix Rachel. I hope I am replying to these posts correctly and following community guidelines. Please let me know if there are corrections needed. Embracing my femininization has been so liberating. It's wonderful!

Thank you for the question. For me it was a very gradual realization. I was a late bloomer, not hitting puberty until after all the other guys. And by then I was already into digital exploration of myself. I would "masturbate" until I was leaking fluid and I thought that was normal. Then came the panties, stolen from my friends cupcake. My first pair were satin and very pink with frill trim along the top. My cupcake caught me wearing them once. Over the years I've tried to embrace the masculine side, but have learned that is a role I play, to fit into what others think of me. A few years ago I stumbled upon some sissy captions and fell in love. I wish I had not tried to fight it so long. But I can take these steps now even though I've known my whole life I'm not like other guys.

Such a weight is lifted off when W/e embrace who W/e are!

[EnchantrixRachel]

Thank you, Enchantrix Rachel. I hope I am replying to these posts correctly and following community guidelines. Please let me know if there are corrections needed. Embracing my femininization has been so liberating. It's wonderful!

You're doing great, Carter!

[Sissy_Carter]

Thank you for the encouragement Miss Rachel

[EnchantrixRachel]