Guys ever been dressed as a girl? I was.

[ben0510]

Hi all. when I was about 15 I went to a fancy dress dressed as a girl. my older sis helped me dress and also did my make up, hair etc. I was quite slim n petite for a boy. also not very hairy so I passed as a girl quite easily. it was an interesting experience and I've often wondered how many people at that party that didn't actually know me, thought I was actually a girl.
any one else had similar experience?.

 

[goodniteswearer89]

I’ve never dressed up as a girl and gone out in public but I have done it at home a few times. When I was younger I would take some of my sisters things like her bikinis or her panties and bras and even a jean skirt and I would put them on but I never went out in public with them on. I think the closest I have gone is wearing some of my girlfriend’s panties under my clothes when I went out but that is it.

 

[ben0510]

I’ve never dressed up as a girl and gone out in public but I have done it at home a few times. When I was younger I would take some of my sisters things like her bikinis or her panties and bras and even a jean skirt and I would put them on but I never went out in public with them on. I think the closest I have gone is wearing some of my girlfriend’s panties under my clothes when I went out but that is it.

did your sister ever catch you wearing her stuff?

 

[goodniteswearer89]

did your sister ever catch you wearing her stuff?

No she didn’t thankfully.

 

[princessarya]

Technically I was a witch for Halloween when I was a child and wore a dress. Sadly no pictures exist.

 

[Diapersntights]

Hi all. when I was about 15 I went to a fancy dress dressed as a girl. my older sis helped me dress and also did my make up, hair etc. I was quite slim n petite for a boy. also not very hairy so I passed as a girl quite easily. it was an interesting experience and I've often wondered how many people at that party that didn't actually know me, thought I was actually a girl.
any one else had similar experience?.

Sounds wonderful fun - I'm sure having a big sister helps that situation happen more easily. Without a big sister I've been a much slower developer as a CD/sissy. Went out once to a fancy dress birthday party once when I was at uni - none of us were ever going to pass, so it was just a laugh, but the girls who were there loved us dressed up like that and we had a great night. I've gone out for the thrill of it late at night under the cover of darkness dressed, just walking around the block and that's the interesting experience for me - the vulnerability I feel dressed en femme - if cornered could I run and escape (probably not) - so I have to really keep my wits about me and feel massively alive while I'm doing it.

 

[Millbay]

When I was a child was dressed as a girl to make up numbers in the school Netball team!

 

[Ali123]

When I was a child was dressed as a girl to make up numbers in the school Netball team!

Oh wow. Why did the netball teacher pick you to join in with the girls? Did she make you wear gym knickers under your netball skirt?

 

[Ali123]

I’ve never dressed up as a girl and gone out in public but I have done it at home a few times. When I was younger I would take some of my sisters things like her bikinis or her panties and bras and even a jean skirt and I would put them on but I never went out in public with them on. I think the closest I have gone is wearing some of my girlfriend’s panties under my clothes when I went out but that is it.

Did your girlfriend know you had her panties on?

 

[Ali123]

Hi all. when I was about 15 I went to a fancy dress dressed as a girl. my older sis helped me dress and also did my make up, hair etc. I was quite slim n petite for a boy. also not very hairy so I passed as a girl quite easily. it was an interesting experience and I've often wondered how many people at that party that didn't actually know me, thought I was actually a girl.
any one else had similar experience?.

What outfit did you wear?

My sister had a fancy dress party for her birthday one year, and I had to go as the White Rabbit, because Lucy wanted to go as Alice.

The outfit was white tights, a white leotard and a red waistcoat. It was so embarrassing.

 

[goodniteswearer89]

Did your girlfriend know you had her panties on?

No she doesn’t know I wear her panties I usually do it when she isn’t home

 

[Ali123]

No she doesn’t know I wear her panties I usually do it when she isn’t home

I don’t wear my girlfriend’s panties unless she says so. I’m sure she’d be able to tell if I just took them and wore them.

 

[googlyeyes467]

When I lived in California I went out as a girl to Halloween and to party a few times but now i just incorporate whatever gender clothes into my wardrobe. It feels more natural for me to be a mix.

 

[goodniteswearer89]

I don’t wear my girlfriend’s panties unless she says so. I’m sure she’d be able to tell if I just took them and wore them.

I’m lucky enough that my girlfriend can’t tell since she is just a little bigger than me and I try to make sure it looks like I haven’t worn her panties. Although I have cummed in a pair of her dirty panties and I don’t think she has noticed but then again I do most of our laundry so she probably hasn’t noticed.

 

[Diapersntights]

What outfit did you wear?

My sister had a fancy dress party for her birthday one year, and I had to go as the White Rabbit, because Lucy wanted to go as Alice.

The outfit was white tights, a white leotard and a red waistcoat. It was so embarrassing.

Having to wear tights - sounds wonderful!

 

[Ali123]

Having to wear tights - sounds wonderful!

Wonderful now. Very embarrassing as a ten year old boy.

 

[Diapersntights]

When I lived in California I went out as a girl to Halloween and to party a few times but now i just incorporate whatever gender clothes into my wardrobe. It feels more natural for me to be a mix.

Congratulations on getting to this utopian situation. The days before Halloween and Valentine's are the great times of year it feels less embarrassing to buy women's clothes in shops!

 

[Diapersntights]

Wonderful now. Very embarrassing as a ten year old boy.

Oh yes, could well have been mortifying back then!

 

[googlyeyes467]

Congratulations on getting to this utopian situation. The days before Halloween and Valentine's are the great times of year it feels less embarrassing to buy women's clothes in shops!

Haha now I wouldn't say it's a "utopian" situation. It's more of like a constant "do I actually look good in this or am I just kidding myself?" but thanks.

 

[Diapersntights]

Haha now I wouldn't say it's a "utopian" situation. It's more of like a constant "do I actually look good in this or am I just kidding myself?" but thanks.

hey, if you've got the confidence to wear it and feel liberated enough to be free to ignore traditional gender boundaries and just worry about what you look good in, then you're doing great. Either way - enjoy it!