Sister-in Law Caught Me in a Skirt

[Jere Oneil]

This past Friday, I was out in the back yard, raking the area where they had had to dig up my septic tank(cost me over $600, but that's another story) the evening before. I was wearing a below the knee length denim skirt. I heard my wife's Boston terriers barking and figured they wanted to go out, so I put the rake aside and headed inside. When I walked in, my wife's sister was sitting in the living room. Her only comment was, you look nice in that skirt. She had stopped by on the way home from one of her frequent business trips to drop off some things for my wife. I hadn't heard her pull up, and, neither her nor we think much about just walking in the door to each other's homes and saying hello as we enter. Upon sitting down to talk with her I discovered that my wife had told her about my skirt wearing a couple of years ago, so although she had never seen me in any skirtlike garment, other than a kilt, she knew I also wear women's skirts at home. I didn't ask, but now I wonder if she knows about my lingerie wearing too.

[Christina Louise]

It's probably got back to your wife already so why not ask her what just what she's told her sister about you. Or just enjoy the slight thrill of not knowing.

[Michelle-NC]

I would bet that she knows more than you think. Sisters tend to be tight and share everything...

[Bobby Anne]

I often either fantasize or wear a simple skirt just to be comfy while the rest f me is all man in appearance. I think if all at once men could wear skirts in public without ridicule , them I might wear one more often.

As a point of info. I am 65 and no longer dress full tilt, makeup, hair and all the rest of the doo dads. I spent 50 years dressing on and off. It all ended last Summer as I went through Chemo and radiation treatments.

Still once a month or so I take a day to dress up privately at home and relax. The desire lasts about a 4 hours and I am satisfied.

I do dream about wearing a cute skirt and walking freely in public as a guy. Still wishing for that overall acceptance I guess.

Bobby Anne

[serinalynn]

I'll bet she does! Both of my wife's sisters know i crossdresss (don't get much help from them) and evey year for my birthday and for christmas I get $25.00 gift cards to The Lane Bryant Store.

[Jere Oneil]

I often either fantasize or wear a simple skirt just to be comfy while the rest f me is all man in appearance. I think if all at once men could wear skirts in public without ridicule , them I might wear one more often.

As a point of info. I am 65 and no longer dress full tilt, makeup, hair and all the rest of the doo dads. I spent 50 years dressing on and off. It all ended last Summer as I went through Chemo and radiation treatments.

Still once a month or so I take a day to dress up privately at home and relax. The desire lasts about a 4 hours and I am satisfied.



I do dream about wearing a cute skirt and walking freely in public as a guy. Still wishing for that overall acceptance I guess.

Bobby Anne

I turn 65 next month, and I underwent the Chemo thing about 10 years ago now. I haven't done the full tilt dressing thing since I was around 14. Then I started putting on muscle and developed more of a fullback's body instead of the cheerleader one I would have rather had. It was about 4 or 5 years ago that I started wearing skirts just about all the time at home. On talking with my wife(she came home while her sister was still there) I found out that she talked with her sister shortly after I first started. Like you, I dream of the day when I as a male can go wherever I want, wearing a skirt and not be considered abnormal. Of course at our age, we are eccentric and not abnormal.

[Emma England]

I often either fantasize or wear a simple skirt just to be comfy while the rest f me is all man in appearance. I think if all at once men could wear skirts in public without ridicule , them I might wear one more often.

As a point of info. I am 65 and no longer dress full tilt, makeup, hair and all the rest of the doo dads. I spent 50 years dressing on and off. It all ended last Summer as I went through Chemo and radiation treatments.

Still once a month or so I take a day to dress up privately at home and relax. The desire lasts about a 4 hours and I am satisfied.

I do dream about wearing a cute skirt and walking freely in public as a guy. Still wishing for that overall acceptance I guess.

Bobby Anne



Well I do wear a skirt in guy mode.

Last April, in the UK it was hot enough for me to wear a knee-length denim skirt to school (one of my cleaning jobs). Certainly too hot to wear jeans at the time.

A couple of weeks later, the employer (a beautiful gg) that I have at a holiday park (another cleaning job) asked me about it.

She said "Dave, were you wearing a skirt to school the other day?" I said I might have done (I couldn't remember as it was 2 weeks previous).

Ellen asked me whether I was gay. So I said no. She said "you just like wearing skirts? Well women wear trousers don't they? Where did you get it from?"

I replied by saying Warehouse (which is a fashionable ladies clothing retailer).

Then Ellen asked me what types of shoes I wear with it. So I mentioned my trainers (assuming that I am in casual mode).

I have not actually worn any skirt in front of her. She has invited me back this year to clean the caravans again.

Do you think this is acceptance or not? Should I wear a skirt to my job when the weather gets warmer?

She is quite attractive (married already unfortunately!!) and she can look at my smooth legs anytime!

Oh by the way, my age is 33 so I am young and confident. My legs look as good in a skirt as any girl. I have never understood why it is not socially acceptable for boys to wear skirts?

[JoAnnDallas]

I would say if she invited you back, she is OK with you wearing a skirt.

[Nicole Erin]

So she knows you CD. Normally people don't pry as to what degree we dress.
I doubt she will be asking for a full list of women's items you like to wear.