SO jumped the gun on a second conversation.
First a little back story. About 8 years ago I told my girlfriend at the time now fiancee that I had tried on women's underwear a handful of times in my life and liked wearing them. She said that it wouldn't bother her too much if I did as long as I didn't wear her's and I didn't wear them when we were around friends or family. After about 4 years of underdressing I started to wonder what it would be like to wear other women's clothes as well. While my girlfriend was away on a trip I bought a few items and tried them out and found that I liked wearing them. A little while after she got back I brought it up with her because I didn't want it to be a secret. I knew it had the potential to be a rough discussion because she had mentioned in the past that she had issues even as a kid with men dressed like women. Couldn't even watch Mrs. Doubtfire. After a very emotional conversation where I tried to address as much of her fears as I possibly could without knowing where all of it was going we settled on a DADT out of sight, out of mind agreement. After about a year, we had to live in separate households in separate states due to the availability of work. This was great for me being able to explore this aspect of myself but the long distance was really hard on both of us. That came to an end late last year when we were finally able to be under the same roof again. Since then, I've been wanting to broach the subject again, just because I have a much clearer picture of what I do and don't want to do and to make sure and reestablish comfortable boundaries for us both. She goes through periods at work where she works hellish hours, 10-12 hours a day six days a week, so I had been waiting until she was on one of the slow periods so that she wouldn't be as tired when I asked her to talk about it. We recently had one of our cats come down very sick, most likely doesn't have long to live so she's been spending a majority of her time in the bedroom where he tends to hangout. I tend to go through periods where I wear women's underwear several days in a row but then don't for awhile. But with her in the bedroom, she was able to see exactly how many days in a row I was wearing them which prompted the ubiquitous...
"Do you have more women's underwear than I do???"
I responded a sheepish, "Yes." and told her that I had gone through a period where I was buying a lot, every VS sale that came around and then finally realized that whoa, I had way more than I needed, considering I don't wear them out as fast. I told her that I had slowed down my underwear purchasing since then and limited myself to only buying a pair if I really liked the design. I also mentioned that I had been wanting to talk to her more about my crossdressing but was waiting until she wasn't so busy with work. She said we could go ahead and talk about it right then as she had brought it up. For the most part it went really well. I was able to give definite answers on some of the major concerns. That I don't want to make any permanent physical changes, no surgery or hormones. I talked about the limited sexual fantasies I had about being dressed in women's clothes, both of which involve her. I told her that I wasn't asking her to fulfill them but just wanted her to know so that there wasn't room for doubts to creep in on what kind of crazy stuff I might want to do. Told her that I didn't have any fantasies involving me being dressed like a woman and being with other men. I told her that I like wearing all kinds of women's clothes and that I liked the idea of makeup but was pretty rubbish at putting it on. We talked about how often I get the urge to dress.
I told her that I don't think I would care if other people knew that I was a crossdresser but that I was in no real need of being out of the closet about it. The one really rough patch came when we talked about going out dressed. I expressed that it was a curiosity but not something that I felt strongly about needing to do. That if I did do it, I would want it to be some sort of socially acceptable place, Halloween, a crossdressing convention, or an LGBT bar or club. She started crying at this point and said that she doesn't think she could be with someone that went out publicly crossdressed, that it would be too embarrassing for her, and that she realized it was a very bigoted view to have but didn't know if she could ever change it. I reassured her that going out dressed wasn't something that was at all high on my priority list. She said that if it was, we shouldn't get married, even though I'm her best friend and she loves me very much. I told her that if it was I wouldn't go through with the marriage, that I wouldn't put her through that. We talked about underdressing. That I enjoyed wearing women's underwear under my guy clothes but I never wore them around friends and family and had extended that to her coworkers as well. She said she wasn't really comfortable with me wearing underwear outside of the house, that she would be embarrassed if someone saw, if say my pants slipped down. I said that in all the years I had been doing it I had never heard any comments or snickers and she said that it must not happen often as she has never been able to tell when I was wearing them and when I wasn't when we were out. I agreed to not wear them out though if it was going to make her uncomfortable. More on that later.
I mentioned how I loved shopping with her both in stores and when she's looking at stuff online and when she asks me what I think about stuff. I told her about how when I first started crossdressing I always felt really awkward about expressing my opinions on the clothes because I didn't want her to be uncomfortable but now that I was more ok with it all that I was having an easier time giving more enthusiastic and detailed replies, which she has been smiling a lot about lately. I told her that I really like that connection we have and being able to do that with her and that was thanks to the crossdressing. She laughed and smiled at that. She told me she didn't think she could ever buy me anything and I told her that if she ever did it would be so incredibly amazing and would mean a lot to me.
Lastly, we talked about DADT and keeping stuff out of sight and out of mind. She said that she didn't really want to see me dressed but maybe it would be a possibility in a few years as some sort of bedroom role play but not a guarantee. I told her that I would like to have a closet to hang stuff up in and put shoes in instead of having all my stuff crammed in a few drawers and my shoes in a cardboard box in the closet. I told her that I wouldn't care if she looked in the closet but at least she would know where everything was if she wanted to avoid it. She was agreeable to that. I asked her whether I should keep a separate laundry basket for the clothes, she said she didn't really care about the underwear being in the joint laundry but that seeing dresses in there would probably bother her. I brought up three things that I enjoy doing that are easy to keep out of public eyes but would be near impossible from keeping out of her sight, which were shaving my armpits and legs and painting my toenails. I told her that I tended to keep my armpits shaved pretty regularly but only shaved my legs now and then because it took me forever to shave them. She laughed and said, "I know! Right?" I mentioned that she might not see the toenails because I tend to wear socks most of the time when I'm home but I couldn't guarantee she wouldn't ever see them. She said she didn't care about the shaving and that she wasn't sure about the toenails, that it might bother her if she saw them, but that we could play it by ear. We ended the conversation on a good note.
The next morning I realized that not wearing underwear out of the house was actually kind of a big deal for me and decided that I would ask her to reconsider. That day was kind of a rough work day so I put it off until this morning. I explained that it was the one thing we had taken a step backwards on and that I really enjoyed doing it. That I would stick to not wearing them if I knew we were going to be around family, friends or her coworkers and re-iterated that after all these years of wearing them out of the house no one had ever made a comment about it. She consented and I told her that I tended to be pretty cautious about making sure they wouldn't show but that if she ever did see them showing to let me know because I don't want them to.
After all of this, she's her typical happy self and no change in how she reacts to me in general. My armpits are shaved for the first time in several months and I picked up a couple new bottles of nail polish. Will wait awhile before I shave my legs and paint my nails though. Don't want to overwhelm with a bunch of stuff right off the bat.
For those of you that have read this far, thank you very much. It feels good to be able to say all this.
And for those of you who feel you might need to comment about her bigoted leanings, a few days prior to this she was ranting about how awful the NC bathroom law was. "Do I contradict myself? Very well, then I contradict myself, I am large, I contain multitudes." ~Walt Whitman
