Wore "Skirt" in front of SO for the first time!!! Kind of.

[Gabby6790]

So, had a weird funny thing happen. First a little background. I am 100% in the closet with SO. I have been dropping hints and pushing some boundaries over the past couple of months. Some of the more metrosexual things have been actually very well received by the SO. But a lot of the hints just get passed off as my not so good sense of humor. Part of that sense of humor is I sometimes do silly things with clothes. This annoys the SO for some reason so of course I do it a lot. Things like pulling my pants up to my chest and things like that.

So, anyway, I am not a morning person. This morning I woke up and and was in a daze getting dressed in my wake up clothes. I was putting on a pair of under armour shorts that are super soft material kind of like their shirts but super stretchy. I always have problems putting them on like by my big feet catching on them and just stretch so much its kind of annoying. So, this morning I am putting them on and I do the old both feet in one hole deal. I was so annoyed and feeling a little goofy so I just pulled them up and walked downstairs. I swear I had no idea what I was doing when my SO saw me and just looked at me. I mumbled some explanation and then she said "your wearing a skirt". That is when I looked down and and amazingly it looked like I was wearing a super cute stretchy skirt. I kind of panicked but played it off. Then we went outside to enjoy our morning coffee and sit down. It was so much more obvious of course cause I wasn't wearing underwear. Maybe next time I should wear panties

My description, doesn't do it justice. I have to take a pic to show you all. All kidding aside it felt wonderful to be "dressed" in front of her. Someday, I will work up the courage to come out to her. Until then, I have these little pleasures.

[Robin414]

LOL, I put my jeans on backwards once and said I twisted my back! I still do that when I'm trying to get out of mowing the lawn! 😂

[heatherdress]

Gabby - Are you going to tell her eventually? How do you think she will react? Could you tell her now? Would you say if she discovered what you do? All difficult questions best answered - by you. Seems like your approach is to continue to drop hints until you get to disclosure. Good luck. I am glad you enjoyed your little pleasure.

[Tracii G]

Might as well put a skirt on next time and act like its a revelation how comfy it is and say I need to wear skirts more often.

[Gabby6790]

Gabby - Are you going to tell her eventually? How do you think she will react? Could you tell her now? Would you say if she discovered what you do? All difficult questions best answered - by you. Seems like your approach is to continue to drop hints until you get to disclosure. Good luck. I am glad you enjoyed your little pleasure.

Am I am planning on telling her eventually. I assume the response will at least be acceptance. I could tell her now but I am still trying to figure out the answers to what I know will be her questions myself. I am probably just putting it off but I recently discovered these forums and am doing a lot of research on what to do and not to do regarding the SO. I also plan at some point to post some of my questions and concerns on here to get the groups valuable input.

[Jenniferathome]

You can't "hint" your way to disclosure. Cross dressing is not in the lexicon of the majority of people. If you want her to know, you have to tell her.

[Tracii G]

You can't "hint" your way to disclosure. Cross dressing is not in the lexicon of the majority of people. If you want her to know, you have to tell her.

I have to agree with this statement.

[Krististeph]

The little things can be a heck of a lot of fun- it shows you are getting comfortable with who you are. Best of luck in the future- do not wait too long. Not sure of the social dynamic you are in but the time is right to come out as a crossdresser or gender disphoric. Please do post pictures- you've got my interest!!!

Kristin`

[Gabby6790]

You can't "hint" your way to disclosure. Cross dressing is not in the lexicon of the majority of people. If you want her to know, you have to tell her.

I am not hinting my way to disclosure. I am hinting to test the waters while I figure some things out about myself. I only figured out about a month or two ago that I want her to know. But wanting her to know and wanting her to know right now are two entirely different things.

[kinkyboots]

I too tested the waters before coming out to my wife. One night it was going "fun" time and i asked my wife to wear some sexy stockings to bed. She asked "do i have too?" And i said that's fine I'll do it myself. When she came out of the shower i was wearing her stockings. She giggled a bit at first and warmed up to them quickly saying she liked them on me.
up until this point my dressing had been dormant for years. New and old feelings rushed to the surface and a month or two later with all my work stress i broke down and took some time off.
during my time off, i told my wife everything, but i opened with "you know that time i wore the stockings in front of you? I really enjoyed that" she responed "i noticed " with a smile and that got the conversation rolling. We like to have these talks while walking as it's away from the kids and if anyone could over hear what we were saying from thier houses would only pick up a small snippet.

[Gabby6790]

I too tested the waters before coming out to my wife. One night it was going "fun" time and i asked my wife to wear some sexy stockings to bed. She asked "do i have too?" And i said that's fine I'll do it myself. When she came out of the shower i was wearing her stockings. She giggled a bit at first and warmed up to them quickly saying she liked them on me.
up until this point my dressing had been dormant for years. New and old feelings rushed to the surface and a month or two later with all my work stress i broke down and took some time off.
during my time off, i told my wife everything, but i opened with "you know that time i wore the stockings in front of you? I really enjoyed that" she responed "i noticed " with a smile and that got the conversation rolling. We like to have these talks while walking as it's away from the kids and if anyone could over hear what we were saying from thier houses would only pick up a small snippet.

Haha, I could so seeing that happening to us but I don't know if my SO's reaction would be the same. My SO is not the girly type so I could get away with the "well fine than I will wear them thing". I get the same pushback on heels from her. I am so tempted to ask her to wear them and they say "fine, i got these 5" platforms in my size, if you wear yours I will wear mine". Although that may be a little obvious.