An SO and struggling with where my boundaries are

[Gillian Gigs]

It is the thoughts and intents of our hearts, motives, that are of importance. Whatever both of you do in the privacy of your own home is your business, as long as you both agreement to it. Think of it this way, when you are dead, what can you take with you into the next life? Your can't take money, or your wardrobe, only what is found within your soul. So, what is found within your soul, your character, thats what. Don't get hung up in small issues, look at the bigger picture, and work at becoming people of good character. The best character example in the bible was all found in one man...guess who, I will leave you to read on.

[KatieOnTheKeys (GG)]

It's not the actual make up lorileah, it's the thing that dressed in female clothing, while wearing makeup, possible a feminine hair do and high heals would make him look female (I think he could easily pass in public ) and because he doesn't see himself as female, I feel that would be a deception :/ if he wanted to transition, or even just saw himself as female when dressed, I'd be completely fine with him going the hog... Does that make sense?

[Lorileah]

I get what you are saying however the point was made after my post that by going out without makeup or wig, he would actually be more noticeable, Just because he doesn't see himself as a woman doesn't mean he can't "blend" a little better. But it depends on his mindset. He would be a huge target and would get a lot of comments (some positive I am sure but most negative). With minimal make up, people will be more willing to "ignore" him....if he is blatant man in dress...they will feel more free to say things

[S. Lisa Smith]

It's not the actual make up lorileah, it's the thing that dressed in female clothing, while wearing makeup, possible a feminine hair do and high heals would make him look female (I think he could easily pass in public ) and because he doesn't see himself as female, I feel that would be a deception :/ if he wanted to transition, or even just saw himself as female when dressed, I'd be completely fine with him going the hog... Does that make sense?

I guess it is from your point of view. I don't see myself as female, as in I don't think I am a woman born in the wrong body, I do see myself as presenting as female. I love all the female "things" shopping while dressed, enjoying the company of females and being seen as one. In my mind, I am not deceiving anyone in that if someone asked me if I were male, I'd tell them I was. If someone glances at me and they think, "what a tall woman (or what an ugly woman or whatever)" they are making an assumption. I don't feel that I am deceiving them. Perhaps it is because I am playing a role and don't seek to profit at someone else's expense I personally don't think I'm deceiving anyone.