Girlfriend dilemma... PLEASE HELP!!!

[Jessifox85]

It feels good to be back to such a great site again! So I'll cut to the chase. I stepped away from crossdressing a while ago and it was of my own choice. Met a girl and let it go right? Fast forward to 8 months ago and the relationship falls apart and I reconnected with a new girl from my not so distant past. ( never dated but knew each other for about 2 years prior.) We started dating.and everything has been great. Till yesterday.. she asked me if I was into crossdressing. In which I kind of brushed off but she said she should tell the answer is yes. Later in the evening she asked me to tell her a secret. So my question is do I tell her? If so what do I say? I desperately miss CDing, but I don't wanna mess up a good thing. And even if I do say anything it doesn't mean I would get to anyways. I'm rambling so I'll shorten it up, should I tell or not? I've never told a single soul before. And if I do how should I plan for the onslaught of questions? I should add I enjoy the feminine figure. ( and in the breast and buttocks) the most. Then the clothing. It is sexual in a manner in a way in my head but not that I'm looking to approach my partner in any sexual manner with my crossdressing. Thankyou so much for help and advice on this I'm very lost here.

[JulieC]

Only you can know your own situation. It's hard to give advice. There's factors that play in here. Will she tell your friends? Family? Co-workers? Can you expect she'll keep the secret?

Even so, if you expect to have a full relationship with this person that might even lead to marriage, then telling her is the absolutely right thing to do. Do you really want to go down that path WITHOUT telling her? Do you really want to spend the rest of your life living in secrecy? Many women, on finding out about their partners being crossdressers, are more mad about the dishonesty in not having been told than they are in the crossdressing itself. I'd recommend telling her as soon as you can.

[JenniferZ]

Yeah I don't feel I can give advice.
For me, the first time I kept it a secret - used to dress at the office. The second time - the first ended in divorce I made up my mind that if she couldn't accept me as is then it wasn't going to work. I'm so happy I did.
Good luck with your decision.

[Jessifox85]

That's kind of what I need to hear. I've kept this secret almost 30 years. I have to decide if now is the time. I feel like this girl is special but I don't know for sure how she'll react or if it will remain in secrecy. But I do trust her if that means anything these days. But might gut says two things. One, She knows something I don't, as in she's found something or seen something. She is the investigative type. And two, I'm terrified at the thought of saying something to anyone. so I'd rather brush it off and move on. But I will say one last thing if there's anything I do know it's I believe her when she tells me she loves everything about me good and bad. So I think she'd understand at least a little.

[Di]

That's kind of what I need to hear. I've kept this secret almost 30 years. I have to decide if now is the time. I feel like this girl is special but I don't know for sure how she'll react or if it will remain in secrecy. But I do trust her if that means anything these days.

It does NOT matter how she would react.
Only thing is she someone you see as a serious relationship.
If you do then you need to be real.
If you think your relationship is serious be upfront.
Anything but that will be much worse down the line.
You can read here all the ones that were AFRAID to be real to sort this out with a partner and hide it and how it is an uphill battle regaining trust .
So my answer if it is a serious relationship/ most definitely yes.

[Jane P]

You said that she is asking you if you cd , I must assume that she has her reasons to ask this and I can only suggest that you be honest with her. To lie at this point is useless (she?s either interested or not)

Good luck with everything!

[Ricky Rayne]

I agree with what DI says. If you feel this is turning into a serious relationship, then YES be upfront about it. Let her ask her questions whatever they maybe. And you answer honestly. If she backs away then she is not the girl for you. Why would you want to stay in a relationship where you cant be you too? There are plenty of women out there that are ok with it and enjoy and participate with it.. So she asked, maybe she has a idea you do, Or MAYBE she is into it and hope you are to.. The only way to know is to communicate. Once you start the dialog about it with her you will probably find out that the "onslaught" of questions really are not that bad. And you might actually feel a sigh of relief for getting it of your chest.

[Jenn A116]

Agree with the PP's that its time to be open. She already knows something of your CD'ing. Be honest and open now. It may save you a lot of anguish later.

[char GG]

There must be a reason she asked if you were into CDing. That is not a typical question that crosses most GG's minds unless they know someone who is into CDing. Did she know of your interest in CDing or have some idea from your prior relationship with her?

So, as others have said, if you plan to go ahead further with this relationship, tell her the truth. It sounds like maybe she knows more about you than you think she does.

It's not a good idea to begin a new or renewed relationship with an outright lie.

[kimdl93]

She appears to already know the answer to her question. Welcome the onslaught of questions. If you know the answers, speak truthfully. If there are some things you are unsure about, just say so. That will do more to cement the relationship than trying to avoid answering the questions you know she has.

[Heather76]

As others have said, there's a reason she asked. Don't start your relationship out based on a lie. Tell her the truth and then ask if that's a problem for her. If it is, move on and be thankful you didn't spend a lot of time and effort nurturing a relationship that was likely to fail at some future time. If it isn't a problem for her, cherish her.

[Geena75]

Maybe you could test the waters. She brought up the subject of cross dressing -- go with that and ask if she has a problem with it, or what she thinks about it in general.

[Kris Burton]

Go for full disclosure. You have the opening, and if she does not have a problem with it, you get to live a truthful life. If she does, you still get to live a truthful life. My hopes for the former for both of you.

[Mary Loo]

Everyone has already provided you consensus. You need to answer truly. You didn’t tell us how she asked you, but my guess was maybe with a bit of a wry smile or smirk, aka, she will possibly be very understanding and on possibly into it. The suspicion is she already learned the truth somehow. If however she asked you in a derogatory or demeaning way, you should still come clean and be similar to many of us here and either learn to compromise OR truly be prepared to give up dressing. Regardless of the fact that the rewards outweigh the risks, it is usually best to be truthful.

We all will be anxious to hear the result.

[AmandaM]

She knows, lol. Just tell her. Act casual, even flippant. Don't act like it's some dark, creepy secret and set the wrong tone.

[Sandra_Dodds]

Are you into crossdressing is a very unusual question and I can only think of two explanations. The first is that she has either heard from someone that you do or has her suspicions based on something you have said or done. Alternatively...and this is every CDers dream; you have found someone who is into seeing her man wearing female attire and she is testing your willingness to participate. Only you can decide which one it is and whether to share your story.

[Sandi Beech]

In your own words - I desperately miss CD?ing. Obviously it is important to you, so it makes sense to disclose your desire to dress before BOTH of you invest a lot into the relationship. Worse case maybe you crash and burn, but better now than later. You might get lucky and have a keeper.

For those of us who did not know we wanted to dress up until after we got married, we never knew to bring it up beforehand. You know beforehand so it will only get more difficult the longer you wait.

Sandi

[Karren H]

Tell her!

[DianeT]

Jessi, if we go by the Ask-a-GG section recommendations, and like many have advised above, you should tell her when things become serious between you and you both start committing to a long term relationship. Before that, your choice.

[docrobbysherry]

I'm a CD. I only tell people on a "need to know" basis!:straightface:

If you're:
Planning to come out, getting engaged, or moving in together? TELL HER!

If u can wait? Wait! I lost a female friend I had for 40 years after telling her!:doh:

[prene]

My thoughts are:
If you're:
Planning to come out, getting serious, or moving in together? TELL HER!

careul though , I have also lost a bunch of GF's when I came out to soon.

[Helen_Highwater]

She knows. As she knows it hasn't stopped her walking away from the relationship. This may well be the golden opportunity so so many dream of. A supportive other and the chance to dress.

You might like to turn it around though. "You asked about crossdressing, why?"

[Jessifox85]

Update. I've told her. Last night in bed I broke it to her slowly and she took it very well it seems. I'm sure she has some processing to do. But she even let me put something on to show her. So I think she understands better than I could expect. She says she's known for about 4 months. She saw a picture on my phone that had her wondering. But it's still a great feeling to get this off my chest.. both silicone and hairy. It's something I've held inside for 30 years.

[Crystal120]

Nice! Glad everything came out ok and hopefully expands now to greater things. You may be able to dress now as you like and maybe with her help.

[Mary Loo]

Great job! So glad to hear confirmation that she already knew. Hopefully she will come to accept it well. Good luck both in the CD category as well as your relationship. Thanks for the update.

[Kelli_cd]

It's good that you told her. I feel that such a specific question deserves a specific and honest answer. Good luck with your relationship!

[alwayshave]

Jessi, I'm glad that you told your GF. and it came out well. I did not want to say come out or not to you from your original post, as I would not want to feel responsible for a negative outcome.

[Kris Burton]

Jessi - spectacular news! Of course it will take a bit to process for her, but if you don't try to move too fast I think it looks like it is going to be fine. All is in the open, and you are both free to develop your relationship with honesty. It's got to feel great!

[Jenn A116]

Happy to hear that it seems to be working out! Now comes the even harder part - don't let it take over your relationship. Let her take the info as it comes up. She will have questions as she thinks more about it. Encourage her to ask questions and answer them honestly. Also, do something nice for her. Show her how you appreciate her acceptance. Maybe a special little gift. Or a hand written note.

[dan.dan]

I have read many stories of thier wives/girlfriends accepting, only to no longer accept. It does not end well. With that scenario, I'm not sure how to fix that, just be aware that it could turn on you at some point.

[Jillian Faith]

I'm glad you told her, now you can move forward to see where this relationship will go, wishing both of you the best of luck.

[DeeDee67]

She already knows, to me it sounds Iike she's asking you to be honest with her. IMHO

[Stephanie47]

If I was in your predicament I would ask her why she thinks I am a cross dresser. There must have been some clue to make that assumption. Then, I would ask her if it would matter to her. If I were to confirm her suspicions I'd tell her my cross dressing is a private affair. I know there is always the peril of being led on, and, then have everything blow up in your face. If you expect to have a serious relationship with her, then I think both of you need to up upfront.

[Marissa Q]

I have read many stories of thier wives/girlfriends accepting, only to no longer accept. It does not end well. With that scenario, I'm not sure how to fix that, just be aware that it could turn on you at some point.

Plenty of good advice in this thread, but I hope the above bit isn't ignored. There are plenty of spouses (male spouses as well) who accept at first, but subconsciously believe they'll be able to -- at some point -- "fix" what in their minds is "the problem". Too often, the acceptance is temporary and statically connected to the idea that the CD'ing won't go any further (when we all know it does). Stay on the alert and don't let your own confirmation bias take over when it comes to acceptance; we all tend to hear only what we want to hear and it's downhill from there once all objectivity is lost.

[char GG]

Good that you told the truth, because she already knew the truth.

[WandaRae2009]

I would not deny it. You wouldn't want to start your relationship with a lie. That would bring up a major trust issue if she ever did find out the truth. As most of us here will attest to, this is something that we just can't stop doing forever. We may dig a hole and bury it or lock the closet door for a while, but it will come back and usually with a real vengeance. Since she brought it up, it doesn't seem that it would be a deal breaker in your relationship, otherwise she would have ghosted you when she suspected. Who knows, maybe she would be supportive and participating. You could end up with a relationship with your SO that many of us only dream about.

Whatever happens, I wish you the best of luck, and please keep us updated on the outcome.

[Leslie Langford]

Take a deep breath, step back, and do a reality check.

You are a crossdresser, and so are we. You're far from being alone in this and it is 2022. We may appear "odd" to some people, but most are aware that we exist and won't head for the hills in shock while clutching their pearls when hearing this. As for the "haters"...well, "haters gonna hate" as the saying goes, so pay them no mind.

If you're new in this relationship and your recent girlfriend has no axe to grind (yet?), why would you worry about her "outing" you? If anything, she will probably appreciate being told before getting too deep into your relationship while she still has a chance to back out if she has an issue with your crossdressing.

I myself am in a DADT relationship with my wife, so it may seem disingenuous of me to give that type of advice. But I've also been married for 50 years and grew up in an era when "transvestites" were seen to occupy a place in society just behind "homosexuals" and slightly ahead of pedophiles on the "Ewwwww...gross" scale. Those prejudices also influenced my wife's world views, and while she has struggled mightily to overcome those in the past years, some old habits and attitudes die hard.

Being a member of the younger generation you no longer face those same challenges, so just tell your girlfriend with no hint of shame on your part because you shouldn't feel any. Just do it at a time and place where you have her undivided attention, she is in a receptive mood, and be prepared to answer all of her questions honestly and in a forthright manner...the first two most likely being "Are you gay?" and "Do you actually want to become a woman"?

[docrobbysherry]

I hope that works out for u. My old girlfriend of 40 years said she was fine with my dressing, too.:thumbsup:

Then, a year later she said she was SO SICK of hearing about and seeing pics of Sherry, she wanted to break off contact with me. That was about 10 years ago and we haven't been in contact since.:sad:

[Pumped]

Jessi, any idea where she got the idea that you might be a CD'er?

Ok, I missed the picture on the phone!

[AmandaM]

Now that she knows, take it slow. Don't hurdle into the Pink Fog. She may love it, or she may just accept it if she gets her guy-time, etc. In the oft chance that you have more inside you - you may decide you are TS, you may decide you want to dress during intimacy, or even decide you want to expand your sexual experiences, etc. Perhaps, she would accept these. But, if you railroad it all at once, she may get overwhelmed. So, no matter what your needs are, remain compassionate to her needs. Hopefully, they'll be the same thing. :)

[Aunt Kelly]

If the relationship is based on your partner not knowing something about you that is this important, it's already "messed up". If you are serious about the relationship, have "the talk".

[Adelaide]

OK. Now that she knows and that she told you where she got the idea that you were a CD, WHAT'S NEXT? Is she OK with it? Her reaction will dictate the future of your relationship.....She needs to fully understand and appreciate you for who you really are.... If she can't, then you know what to do.....

[kimdl93]

Ok, so she has known for 4 months. Not just suspected, but has seen the picture. So now how to proceed. Best advice is to let her choose the path forward. If, when, what and how often. If the relationship held together for those 4 months after her discovery, its possible that things could work out for the long run. But take nothing for granted.

[Amy Lynn3]

As Char GG said. Women do not ask questions like that unless they already know the answer. Remember to put her first in your life and CDing should be in the background. Allow things to move slow at her leading. It will be wonderful to have a soul mate that loves you for what you are. Di had a relationship like that and gave good advice.

[Ricky Rayne]

I am glad you opened up about it. Its sound as if she had a very similar reaction as mine did, and its positive. Also let her know that its ok to tell you if you are doing something that is too much or over her boundaries. She has to know that you are open to HER feelings, opinions, and comfort zone too. As exciting as this sounds and as new as it is for you, Don't dress everyday even though you will want to, remember to also be the person she was attracted to in the first place. Just don't overwhelm the situation... Good Luck, I'm happy for you, as always keep us posted!

[Natalie5004]

I would say to let her think on this for a while. The jury is still out on this.

Women can take months to process this.

Do not push.

[JulieC]

Congrats Jessifox! She probably appreciates your honesty, given that she already knew.

[Heather76]

So glad you told her. Wouldn't you have hated being caught in an obvious lie when she already knew the truth? The fact she was willing to let you show her is really quite impressive. Good luck going forward.

[DianeT]

For members still asking how she knew or advising about telling/not telling, you may be interested to know that Jessi has already responded to these questions in his third post.

[Jessifox85]

Yes I have told her. And it did go very well. She is very supportive and does have a lot of questions. Personally I've decided to take the long approach to this I don't want to rush her into it. Deep down I would like this to bloom into her being involved somehow but if not I'm okay with that. Thankyou all so much for such great advice and the encouragement more than anything!

[SaraLin]

It's good that you told her.
It's good that she didn't run for the hills.

But

I'm a little bit worried about her "finding" the picture on your phone. I say this because I'll bet that she didn't get your "OK" first.
IMO She either has boundary issues - with no respect for your privacy, OR she has trust issues and feels the need to "check up" on you.
How do you think she would react if she found out you'd gone through her phone and discovered some secret of hers?

Still - I wish the two of you all the best and I hope you find nothing but happiness.

[fly2188]

But

I'm a little bit worried about her "finding" the picture on your phone. I say this because I'll bet that she didn't get your "OK" first.
IMO She either has boundary issues - with no respect for your privacy, OR she has trust issues and feels the need to "check up" on you.
How do you think she would react if she found out you'd gone through her phone and discovered some secret of hers?.

Probably depends a lot on the relationship. Girlfriend of 8 months is one thing, but my wife and I freely use each others phone. Heck, we?ve programmed each other?s faces into our phones for the facial recognition to unlock them. Sometimes I want to take a photo, look something up, etc. and her phone is closer.

Nothing odd about that.

[KymG]

Well she either knows or suspects.
Id be in two minds.

Either tell her and take control of the situation, by being totally upfront and ask her if she has any questions. Perhaps open by asking why she thought you were a crossdresser?

Or, find out that she has told others. In my case, i told one person and i understand that four more now know aswell. Hmm.

[ziggie]

I'm glad things seem to be working out. It is best to be out in the open if it is possible.

[Sandra_Dodds]

She says she's known for about 4 months. She saw a picture on my phone that had her wondering.

That's what I was expecting.

[TheHiddenMe]

Actions speak louder that words.

Good that you fessed up.

Even better is that she's known for four months and she didn't run for the hills when she found out. That should tell you, at least for now, she is willing to continue the relationship with you. Obviously, there are no guarantees, but I have to assume that you being honest is a plus with her.

[mbmeen12]

Super happy for you...Now.... crawl, walk and maybe run....Make a date dress night for you two, once a month etc ...
Good luck...

[Supporter86]

Hey guys! I am the girlfriend. I really appreciate the support that you have provided Jessi during this time. As he said, I?ve known I just didn?t want to assume and I also didn?t want to embarrass him. I?m a pretty open minded person and well rounded so I think that the news was harder for him to spill than it was for me to accept. I love everything about him, male or female, and loving someone means that you stick by them and support them no matter what. And that is exactly what I will do. Seeing him dressed up as a female doesn?t weird me out. Maybe because I?ve had relations with women in the past. So for me it is like the whole package. I?m really enjoying it. I do enjoy my time with him dressed as a man, but I also enjoy it as a woman. I?m ok with 50/50. At the end of the day this opened up a huge door for us and we have enjoyed the ride. I hope we have a lifetime together to explore and be happy. His happiness is so important to me and seeing him this happy makes me just over the moon excited. Honesty and self love are very important. If you have to lie about who you are to your partner, he/she isn?t the one for you. You should be able to be the safest with your partner and the most vulnerable. I?m glad that he chose me.

[Sandi Beech]

Wow that is really cool that you joined us here - a rarity as far as I know. I mean we have a few but we do not see a lot of new GGs pop up.
I am sure you can make him happy and vice versa. It is really just a matter of finding the balance both of you are comfortable with.

Good luck to you both. Glad you stopped by. Don?t be a stranger ; )

Sandi

[Supporter86]

Thank you. He told me that this was a place that he likes to come and feel normal, and I want him to have as much as that as possible. Thank you guys for helping him find himself. I?m so thankful for him and this site. I will definitely be here more often.

[Sabine Janus]

Why did she ask that SPECIFIC question?

[Pumped]

Sabine, she saw pics on his phone.

[Valerie Louise]

Miss Supporter, you are fantastic! I think your outlook is super positive and portends a wonderful future. Jessi is darn lucky and I?m sure she knows it.

[Jessifox85]

Valerie you are absolutely right! This couldn't have gone any better. If there was a CD Olympics I'd of got the gold in comming out to someone. But she is an amazing and strong woman. I hope you reach out to others in here for advice. Especially the support groups for loved ones.
But I have to say to everyone the love and support from this woman has been more than I ever dreamed of. She has been so patient and caring. The first day or two we were trying to just understand what had happened. But since she's really trying to embrace it. I could have never asked for a better outcome, I only hope it last but I understand that that's my commitment to her and the way she feels.

[mykell]

congratz to you both.....seems you were destined to meet each other.....