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I am very fortunate. My hairstylist and I go shopping at least once a year to the outlet mall in Williamsburg. I have befriended a number of sales associates there and go shopping at their stores. They always help me with suggestions and more importantly, vets. We have a blast. I have also gone shopping with my wife (I was not dressed) and bought clothes to wear en femme.
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Please do be cautious until you know this person and her background better.
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I go shopping quite often with my GG daughter, with me fully en-femme. It's tons of fun for both of us to get out and hit the mall for a girl's day out.
Haven't gone shopping yet with any of Ceera's GG girlfriends. Most of the GG's I know as Ceera are friends I go to happy hours with, as part of a LGBT Ladies group. I've only been on one date with a GG as Ceera - out for drinks and then a nice dinner.
A shopping trip with a GG friend other than my daughter would be fun, even if we were not romantically inclined. But most of my 'lesbian ladyfriends' aren't that into fashion or pretty shoes or jewelry.
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I'm a solo shopper, which makes me feel kind of lonely, but I still enjoy myself. I only (finally) came out to my wife last week. She has been very accepting, but is not up to going shopping with me at this point, although she hasn't fully ruled it out, but she is still processing. I wait patiently for the day when this may change!
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As I've pointed out before in the past I've shopped with various women. My wife and I have several women friends who know about me. Over the years they have moved away and a couple have passed on. We used to go to sale days at various mall department stores or discount malls. I also have gone with a few by ourselves. While shopping we didn't always hang together. Many times we have gone out and enjoyed wine or martinis afterwards. It was fun talking and showing our finds.
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I have a very good GG friend who loves to shop and going with me is so much fun for her. Our last outing we hit a consignment shop and then White House Black Market and tried a couple of outfits which did not work. We were about to move on when my friend spotted a pair of dress pants which were on the list to find on this trip. The pants were on the clearance rack and fit perfectly. Teri remarked that my painted toes really was a nice indicator of female to the casual observer. We took a break for a nice dinner and then hit the Macy's where I took several separates into the room and Teri came in to check fit. When something did not fit she would go find me something else. We found the white ruffle front blouse we were looking for and the jacket, along with a lovely off white suit. As we were heading for the check out we found the perfect black cowl neck blouse to go with the suit. We were the last one out of the store. We have done this several times and each time has been so much fun. One thing you should know is that girls do not hold the door for other girls! The first time we went out I went through the door wand was holding it when Teri whispered in my ear not to do that. That was the last macho thing I did.
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Yes, the greatest part of having an accepting wife. Lunches, dinners, movies, manicures and shopping. Wonderful.
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I've gone shopping and for pedicures with various female friends, all of whom offer invaluable advice, take pictures for the occasion (beats having to awkwardly ask a sales associate to do this), and best of all -- make amazing memories! Your femme self may be particularly vulnerable (mine is), and to have a friend give themselves to you fully, in public, taking on the world is one of the most refreshing feelings. I make sure I constantly pour back into these friendships.