My situation

[Miss_Roslyn]

So it had been years since I had done anything in the way of cross dressing but this past summer I found a pair of my girlfriends underwear mixed up in my freshly washed laundry. I couldn't resist the urge to try them on so it did. Over the next couple of months when she would go to work I would try on her things and put on her makeup. It was quite the rush. But now she is moving back to England with the rest of her family. Her parents are already over there and she is leaving in about two weeks. I feel like I will go through a rather natural depression from missing her. I have been with her for one year and 10 months and I love her so much I cannot wait for the day to marry her but being as we are young and neither of us have finished college we feel we should wait before we tie the knot. But that brings me to my current situation she is leaving and I will get depressed but I was thinking that instead of my usual routine of when things get bad of drinking and partying. I would channel my inner girl and get to know "roslyn" a bit better. And I would do this except I have a room mate which also happens to be a real good friend who also happens to be gay. The gay thing isn't that important he's gay, I'm not and it doesn't bother me what he does. I was thinking about telling him this plan and of my curiosity with cross dressing. But I'm scared it will change our friend ship or if I piss him off he might throw it in my face or he might slip and tell someone. Any advice girls?

[Karren H]

Yeah! And tell your room mate.... He will understand .. And tell your girl friend before she leaves. She may not.

[kimdl93]

I don't see any reason not to be open and honest with your room mate. My guess is he'll be understanding. Then of course there's the question of sorting out your interest in CDing. If you think this is just a momentary thing - a way to deal with being lonesome, that is fine, but its possible, perhaps even likely, that CDing may be a larger part of who you are. In that case, you'll need to talk about it with your GF before you "tie the knot".

[Marleena]

Great advice so far. I'm pretty sure your room mate will be fine with it.

You need to find out if CDing is a part of you that you can't give up. I suspect it is since you had a reawakening. If you can't give it up, your future wife needs to know.

[DonnaT]

I don't think now is the time to tell your GF. The time to tell is when you determine, while apart, you want to take things to a more serious, possibly permanent, level.

getting to know "Roslyn" a bit better, may take more than alone time, and instead you may want to be able to interact with others to get to know yourself better.

So it might be best to tell you room mate, especially if the chance of getting caught dressed is highly likely.

[Leilani]

I would encourage you to tell your girlfriend of this. I know that I did not tell mine until a number of years after we were together and it hurt her a great deal as she felt lied to and very confused. It also made her think that if I could hide something from her for that long what else could I be hiding from her. You relationship has gone on for almost 2 years so with the benefit of hindsight I would say you are already about a year and a half late. I think telling your roomate might not be a bad idea since he will probably be a little more understanding of the issue than others. Could be an assumption on my part but that is how I would guess the situation is. It still depends though on how he is as a person so use your judgement. Finally I would like to say that you should not be wearing her clothes without asking. Although a lot of girlfriends do wear their boyfriends shirts, boxers etc... without asking since it makes them feel close to him (because it smells like/reminds her of the boyfriend), I tend to see this as different. Their are concerns and confusions that arise for women with regards to this issue and I think it makes them feel more violated than anything else. Unless of course they know about and support the issue and have said it is fine to do so. I could be wrong please feel free to let me know if I am. Just my thoughts

[Miss_Roslyn]

You all have great advice and perspectives. But as some of you mentioned I'm still not sure if this is a lifestyle for me or a phase? I don't want to tell my girlfriend just in case it is a phase. If it becomes more, which I don't see happening, I will tell her but something tells me that she has a clue. As I stated, she is moving well while she was going through her clothes he asked me if I wanted some pairs of her old underwear. I asked "like, for what?" ad she just kinda went quiet. It was kinda awkward. And one time after putting on mascara, I thought I got it all off but she made a comment on how pretty my eyelashes look. I think her being a girl knows something up. Bu she knows me and knows how embarrassed I get over the smallest things so for my pride sake she's not bringing it up. She really is great. And yes it was wrong to try on her clothes with out her permission but it was an urge that I couldn't fight. So that's we're I'm at. I feel if this is just a phase my gay roommate would be chill with it. And maybe we could go out to gay bars he's single and even though I'm not interested in guys. Gay clubs are more accepting to cross dressers?!?

[IamSara]

Tell the room mate and the GF. You will be able to explore whether you really are a CD or are just interested in it for a short time. Honesty is the best way. I learned the hard way.

[Launa]

[QUOTE=Miss_Roslyn;2700076]You all have great advice and perspectives. But as some of you mentioned I'm still not sure if this is a lifestyle for me or a phase? I don't want to tell my girlfriend just in case it is a phase. If it becomes more, which I don't see happening, I will tell her but something tells me that she has a clue. As I stated, she is moving well while she was going through her clothes he asked me if I wanted some pairs of her old underwear. I asked "like, for what?" ad she just kinda went quiet. It was kinda awkward. And one time after putting on mascara, I thought I got it all off but she made a comment on how pretty my eyelashes look. I think her being a girl knows something up. Bu she knows me and knows how embarrassed I get over the smallest things so for my pride sake she's not bringing it up. She really is great. And yes it was wrong to try on her clothes with out her permission but it was an urge that I couldn't fight. So that's we're I'm at. I feel if this is just a phase my gay roommate would be chill with it. And maybe we could go out to gay bars he's single and even though I'm not interested in guys. Gay clubs are more accepting to cross dressers?!?

I think your roomate will be fine with it just the same as all the other girls here agree. So I say go tell him and discover this side of yourself, find out how you want to make it part of your life.
As far as the girlfriend goes, I would tell her when the time is right even if you think you can surpress all of it once the 2 of you get married. I would tell her absolutley everything.
In my situation I told everything to my wife before we moved into together many years ago and at the time I was only wanting to wear dresses in private around the house and thats the way it was for years until I had a medical condition flare up. Suddenly I could not play sports anymore, then went into a major mid-life crisis and all h*ll broke loose.
Now I want to get dressed all the way into full girl mode and get out there in the world! My wife says holy sh*t, you never said you needed to go that far. I said I didn't think I needed to go that far either but now I do.
So honesty is better even if you think you can shove this thing under the carpet because you never know when it can raise its ugly head again.

[Jilmac]

Come clean to both. If your roomie is fully aware to the T in LGBT, I'm suer he won't have a problem with your dressing. If you tell your GF now it will give her time to digest the information before she returns to England. As for you treating your mourning (after she leaves), Dressnig can be just as intoxicating as alcohol, but without the hangover.

[Vickie_CDTV]

Your girlfriend probably knows something is up, otherwise she would not have offered to give you some of her underwear. Regardless, if you do become serious with her, you still have an obligation to tell her about your dressing. There is no ifs ands or buts about it, she has a right to know and for you to confirm what she already suspects.

And for goodness' sake, yes be sure to finish college before you get married! Both of you should be employable and not dependent on the other one when you marry, financial dependency could cause serious problems down the road; seen that senario way too many times in my life!

If your gay friend is trustworthy then you could tell him. But, I would be very careful and make sure he really is trustworthy with such a secret before I'd tell him.

[Lucy_Bella]

Advise,
I would hold off on telling the girlfriend, I say this because ( from reading your post ) it appears that you are just starting to explore your dressing.. Heck you don't even own any of your own things yet so how can you even begin to explain your situation with out fully knowing just how far you will go? A better understanding of yourself ,your desires and the spectrum level you may find, may end up being a better understanding for any potential mate. Most of us who do tell from the start will unknowingly miss inform our mates due to not fully understanding ourselves within our spectrum level resulting for some, to lying ( how the girl friend see's it ) about our desires.. Get to know your self better ..

You might start out as wearing her panties and some make up ..AT FIRST.. She may find that cute and innocent but watch out if that desire grows.. I have found most GG's DO NOT find that when your desires grow in dressing as being honest with them .. They fear it ! Ending in a mis understood relationship very few GG's will allow or put up with any growing desires in your dressing..So know yourself first that is being honest from the start in my opinion.

I am also a straight CDer , I have a few Gay male friends that know of my dressing and respect my sexuality. I have no doubt in trusting them with my secret ..Most every GG I have told has at one time or another threaten to out me ..

[JiveTurkeyOnRye]

I think you should tell them both, but be careful with talking to your girlfriend because you've also been massively invading her privacy and trust by wearing her clothes without her knowledge. When you do talk to her though, be very honest with exactly how you feel. Say that this is something you used to do and that the feelings have resurfaced, and you aren't sure what it means but that it is something you think you're going to explore in her absence. I think it would be unfair to keep it from her because if she's going to be back in england and keeping herself attached to you romantically despite the distance, she should know this about you. Even if this is just a phase, she shouldn't be kept in the dark about it.

[suchacutie]

I'm not quite sure what you are going to tell them. Would it be, "I've experimented a bit with wearing lingerie and applying makeup"? What does that mean?

It is unfortunate that you have broken your GFs trust by using her things without asking, so please stop that immediately. If you tell your GF something like I've mentioned above, she will have a million questions for which you will have no answer. What will she think of that? So, I don't think it's time to tell the GF. Once you've experimented a bit and begin to understand what your feminine side means to you, and you are in the same room as your GF, then you need to begin that discussion, knowing that she may "out" you at that time.

As to your roommate, you can tell him that you are interested in exploring your feminine side, and that you have no idea where that will take you.

Does this help?

tina

[Cassandra Lynn]

Hmmmm, let's see here:
"drinking and partying when things get bad" or "getting to know Roslyn".

Using alcohol to numb things is bad road to go down, while giving birth to your inner girl is a new beginning.

Decisions decisions???? I know which i'd choose.