Crossdressing Boyfriend

It is a shame there aren't more women out there like yourself that is willing to see the person inside and not what is on the outside. Most of us would make any woman happy if they would let us be ourselves at times. Just keep at it and allow him to dress at home and look on the world wide web at woman's fashions, I'm sure in a short amount of time he(r) will be willing to go clothes shopping or at the very least window shopping. Especially if you ordered something either to small or to large from the web then lightly tell hill it would be better to shop in person for something, or better yet find a local support group and go with him to it.

Anna, glad you could drop in!

First, let me put out the disclaimer: I am not a professional counselor or therapist.

When I was in engineering school, we had to take a certain number of Humanities courses. I chose a lot of psychology courses, but that by no means makes me an expert. However, I still remember some of the constructs and the behavior you described sounded a lot like "Approach-Avoidance Conflict". On one hand, we can be very desirous of a particular experience, but really worry about how it might look to others or what it might reveal about ourselves.

Sooner or later, many crossdressers get to the point where they have to reconcile this added facet with the rest of their lives. It's not an easy thing to do and many will struggle mightily. You have to remember that we have been given a lot of conditioning in society regarding thinking of sexuality in a binary context. That makes it tough to even consider a state beyond our traditions.

Further, many people want to assume that crossdressers are gay. Surprisingly, the largest single group is heterosexual males. For some crossdressers, the hard part is dealing with the societal perception that you are gay, regardless of what the reality may be.

You know, if it was easy somebody else would be doing it...

He needs to accept this as part of his personality and embrace it. I give him credit for having courage to at least be honest with you.

Keep being supportive and understanding and it will help him to become more confident in himself when he is or isnt dressed.

Be his rock, his guide, and biggest cheerleader and he will never leave you. He should always respect your wishes too. There is a selfish stage, work through it, and "she" will grow up into a complete person. I did with my wife

Anna,
Like the others I agree that your BF is lucky to have an understanding GF like you.

Have you ever taken him shopping for you? Let him know that you are shopping for you and not him. Ask him the same questions and you will probably see a difference in his behavior. Once you established this behavior, on later trips you can ask him if he would like that pair shoes, that nightie, that skirt.

Good luck and enjoy these experiences.