Wanting to go out

[Gwinnie]

This all started when I was real young and I would dress up in my mom's clothes. I thought okay, that's fun. Then when I got older it was more of a sexual thing. I still kept it hidden. I finally told my wife about it. She seems to be okay with it. But now I feel like I want to go out of the house and around town while dressed. Thing is, I want her to go with me. Kind of like a girl's night out date type thing. I found the dress, hair, and shoes I want to wear. It's a long maxi dress so legs would be mostly covered. Also found a shrug with puffy sleeves. Cause, I have to have puffy sleeves.She says she thinks she would be okay with it as long as I wasn't self conscious about it the whole time. Yeah like I couldn't be. Also a bit worried about running into someone we know. But really, we go out often and rarely run into someone we know. But of course this would be the time. One other problem I see is that the hair I want looks very similar to hers. Any advice?

[Jessica Who]

When it comes to going out, my advice would be to wear what other women in your area typically wear and start small. You're going to be self-conscious for at the least the first few times, so maybe get a little practice before you bring your wife.

[Sandra1746]

Going out dressed is fun and perfectly OK. The only thing you have to remember is to be prepared to run into someone you know from almost any venue you frequent. If someone recognizes your wife and comes over to say "hi" your hiding under the table is only going to attract attention. Chances are you will do just fine and have fun but just prepare for the "outing"; in more ways than one.

Don't let fear keep you in the closet,
Sandra1746

[franlee]

Jessica gave you the answer to the dilemma. I will add that when I did it years ago, went out of our immediate area and where it was congested with people. I stayed with my wife so as she could do any talking and we stayed out of any kind of focal point. It was great and now that she has passed away it is more than special memories, but were before too. Don't let fear stop your best chances to live, just plan it out and use a little common sense.

[Gwinnie]

Another thing that concerns me is that my wife and I are very touchy feely with each other. Always holding hands or running into each other on purpose. (It's cuter than it sounds) I wonder how she would feel about either being the same way with me looking like a girl, or trying to be hands-off. I don't think I would want that. As for wearing what other girls wear, around here right now they could wear about anything. We got 9" of snow on Monday and it's supposed to be 60 this weekend. I was looking for a long maxi dress with a little white shrug. Puffy sleeves of course. Then some wedge shoes, wig and maybe a headband or flower.

[kimdl93]

Sounds like you have set your mind on the outfit. I would run it past your wife for her opinion and be open to any changes she may suggest. And for this first time out, perhaps go somewhere just a little farther from your normal stomping grounds. You'll relax more.

[Gwinnie]

Yeah. She mentioned she wanted to buy me the dress. Of course the store doesn't have my size anymore. I'm not sure where we will go exactly. I thought of taking her somewhere to take her shopping and dinner or something

[Jenniferathome]

... She seems to be okay with it. Any advice?

i would start here. have a long and detailed conversation and then KNOW she is ok with it or understand her fears before you ask her out.

[Chari]

Great that you are planning a "girls night out"! Previous suggestions are good advice! Also consider "blending in" not only with your clothing, but with your make-up too. Be sure to try on everything, including make-up, and practice walking, sitting, and general feminine movements to be comfortable BEFORE you go out. This outing can be a most enjoyable learning experience. Be sure to take some pics too. Thanx for sharing.

[Suzanne F]

My first trip out was last week with my wife and a girl friend. We had a great time! It was a little scary but I am so glad I did it. It was great to be so supported by my wife and friend. My wife could not keep her hands off of me!

[slamddoger]

so what stoping both of you for going out? do you live in small town if you do then go to the next town over

[Beverley Sims]

Steve, you have the opportunity and all you need to do is overcome your fears.
Drive to another town and start there.
There are a lot of opportunities.
If your wife is willing to help, assist her by overcoming those fears.