New to cross dressing

[tony]

I need a little help with just what to do. I recently started wondering what it would be like to wear womens underwear because to me mens are somewhat uncomfortable. I talked it over with my fiance and she said all I can do is try it. So we went out and bought me some and I now where them on a daily basis. Now I have been talking to her about breastforms and a bra. She is ok with all of it which helps me out tremendously, but then i find myself questioning it. I know i'm a guy and prefer to stay that way, but then I can't help but wonder what it is like to be all dolled up. I don't care for the make up and I don't care to do it in public, but i find myself with these urges and don't know how to react. I know that from what I have read that it can help with stress and calm you and that may be part of why i want to do it. I'm scared of liking it and wanting to take it further. My fiance keeps telling me to see if I like it and we will go from there and to do what makes me feel is who I am. I'm just not sure and I need a little input before I start to take my cross dressing any farther.
                    Tony

[Robyn]

Well, since you have a supportive SO, give it a try in the privacy of your own home.  Maybe she would go with you to a thrift store to pick up a few things.  Thrift stores are a great way to find your sizes and styles without breaking the bank.  Sometimes they even have some wigs. 

Robyn

[Louise]

I know i'm a guy and prefer to stay that way, but then I can't help but wonder what it is like to be all dolled up. I don't care for the make up and I don't care to do it in public, but i find myself with these urges and don't know how to react.

Tony,
Most of us crossdressers are neither gay nor transsexual.  I have had the urge to crossdress all my life and have been doing it at home on a weekly basis for the last ten years.  My wife knows and is supportive, so count yourself lucky that you have a supportive SO.  There are all sorts of theories as to why men have the urge to crossdress, and there is probably no single good explanation that fits all of us.  Why we do this is not as important as realizing that this is a part of us that will not go away and it needs to be accepted.

Having said that, what I suggest is that you experiment.  This can be an expensive "hobby", so I suggest going slow.  Try going shopping at a second hand store with your SO.  Pick out what you think you'd like to try.  Once you find what you like and what suits your style, then you can invest in better clothes.  Personally I like nice clothes, but I buy one or two new outfits a year.

You also need to experiment to see what comfort zone you and your SO need to establish.  My advice here is to go slow and keep the lines of communication open.

Louise

[tony]

Thanks for the help. I'm new to this and just want to know what to do or how I should do it.

[robinhayes]

I need a little help with just what to do. I recently started wondering what it would be like to wear womens underwear because to me mens are somewhat uncomfortable. I talked it over with my fiance and she said all I can do is try it. So we went out and bought me some and I now where them on a daily basis. Now I have been talking to her about breastforms and a bra. She is ok with all of it which helps me out tremendously, but then i find myself questioning it. I know i'm a guy and prefer to stay that way, but then I can't help but wonder what it is like to be all dolled up. I don't care for the make up and I don't care to do it in public, but i find myself with these urges and don't know how to react. I know that from what I have read that it can help with stress and calm you and that may be part of why i want to do it. I'm scared of liking it and wanting to take it further. My fiance keeps telling me to see if I like it and we will go from there and to do what makes me feel is who I am. I'm just not sure and I need a little input before I start to take my cross dressing any farther.
                    Tony

Tony - as long as you approach it in a healthy manner, exploring, then there's nothing to worry about.  Especially if your fiancee is supportive, since she can be a "second set of eyes" to make sure you aren't getting carried away.

That said, what you describe is in my opinion a logical progression.  If you have any internal shame about crossdressing, then it's easier to take baby steps and see what you enjoy and don't enjoy.  Some people also find the "naughtiness" of it appealing -- either sexually or as a game with a partner -- which is also OK.

The important thing is to be willing to experiment, to realize that you are in control, and that you have a partner who will help you as you decide what you (and she!) are comfortable with.

The other thing I'd add is that you're REALLY smart to have told her early on in the relationship.  I waited until after I had been married several years, and that made the whole thing much worse.  We're still working out our boundaries and so on, but universally people who tell their partners before they get married have much better luck no matter where on the TG spectrum they wind up at the end.

Regards!
Robin