Just a quick survey...

[Toni Citara]

Just a quick survey... over the past couple of weeks I have re-connected with a long-time love of mine, we've been talking about "giving it a shot" - as in, dating and becoming a unit, maybe marriage... problem is she is Vanilla. What should I do? I know she would freak the hell out if she knew of this fun side of my personality, (not to mention her parents, who love the stuffing out of me!!), and honestly I would hate to lose her because she really, truly is somebody I could see being married to for the rest of my life. Yeah, I know.. that sounds corny and never in a million years would I have thought post-divorce I would ever feel like that, but the heart wants what the heart wants, and I want her in my life.

Problem is that my track-record with women is shot all to hell after I tell them about my crossdressing. I purged and gave it up for 20+ years of marriage, and after finding myself again, I hate to kill off "Toni" just so "Tony" can be happy.

So... can the two sides exist?

I gotta say - HELL NO. That's based on my past experiences. Every single time I've broached the crossdressing topic, the relationship dies.

Oh, Happy 2014 ya'll!!!

[docrobbysherry]

If crossdressing is a part of who u r, u need to discuss Toni with your potential SO. If u can give up Toni for another 20 years? Don't talk about her. However, if the latter is your choice, is that realistic? U must be who u r and an SO should accept u for who u r. As should u, her!

[jessica2009]

I feel sorry for you that you are not able to bring your other side out. I was semi lucky to have an accepting SO... So I would say "yes" it is possible to have two sides exist, just gotta find that special someone. I know you haven't had a good record on coming out to your SO's but it WILL happen. just gotta have faith and let the right person come along :)

[heatherdress]

Seems like you are in a post divorce relationship and should not be thinking about marriage. Seems like you might need to simply maintain Vanilla's friendship at this point.

Maybe Vanilla is not the right person for you to be with the rest of your life, maybe Vanilla would surprise you if you tell her, maybe you can live happily with Vanilla without Toni or maybe there is someone else who would be happy to be with Tony and Toni.

But give yourself some time.

You did ask if the two sides can exist - yes they can. I went thru several relationships after my divorce and I found someone who loves me and fully accepts my crossdressing.

[Stephanie47]

I'm kind of with Heather on the timing. You state "reconnecting" within the last several weeks. That sounds somewhat like somebody on the rebound. If I were you I'd let the relationship "mature" a little before even considering anything further than a casual relationship. Finding out her take on cross dressing and alternative lifestyles? I guess you can play all the hint games; watching Tootsie and the like, going to see drag queens; taking in a gay pride parade. If I had denied myself for twenty plus years, I'd be darn sure my honey was accepting, if not participating, before I'd sign up for another twenty of cross dressing celibacy.

[Katie_Did GG]

Whoa there sweetie. You are trying to make a decision based in part on Vanilla's being Vanilla and you have just reconnected?! :lol: Trust me if you can look in the mirror and tell us you have not changed one bit in regards to what you do & think now verses +20 years ago then and only then can you assume others haven't either. Take things slowly with anyone you start seeing. This should be a time of discovery and fun: seeing what you have in common and if any sparks are still there. Time enough to think about marriage later. And you would be amazed what a Vanilla will try, and not only like, but love with the right partner.

[Rachelakld]

My thoughts are -
If you truly love her, you would give her a choice, otherwise you just want to "own" her or like to be "see being married to".
If your not willing to give her the opportunity to know you, she's not the right girl, move on and find one you are open to.

[bridget thronton]

Marriage is a relationship where you should be able to talk about anything - secrets are not appreciated

[Beverley Sims]

It is a bit of a dilemma, I advocate honesty and the longer the relationship goes the harder it will be to tell.
I would let it solidify a bit first and mention that as you got older things have changed.
Read the various coming out threads that are well documented here.
Good luck with it I am sure you will find a solution.

[Tracii G]

I don't know how long you have been divorced so I will ask this: are you one of those guys that feel he HAS to be in a relationship to whole in your mind?
If you know she will freakout over it why even bother getting into a relationship with her.I would think back as to why you broke up the first time.
You don't need to be thinking of marriage right after hooking up again get to know her all over again.
I started dating and old friend of 30 years and when she mentioned marriage I let her know that is not in the picture and I wasn't going to do that again.
I did tell her I was TG even before the first date and she was fine with it.She even enjoys that side of me but I don't push it on her.
My suggestion is take it slow and let her know you CD its best to get that out there.
If she bails you have lost nothing.Who wants to be with someone that can't accept you fully?

[Kate Simmons]

Sounds like you have to make a choice. Only you can decide what is more important to you. You have to make a choice you can live with.:)

[Vickie_CDTV]

At some point you have to tell, I'd hold off and pursue her and see how things go so you can at least get your foot in the door; if you tell her right off, she might turn and run away immediately. Of course, if you get into a relationship and it gets serious, you then have an obligation to tell her (you can read the painful consequences of not telling her all over this site.)

[Katey888]

Toni - I feel for both parts of you. If I was able to tell a potential SO from the outset I would - it's not as easy once the relationship develops and reactions are rarely fully rational. Strikes me you really have to decide whether you want the long-supressed Toni to be a long-term aspect of your future... that's not easy for any of us, but if you decide yes, then you would be fooling yourself and any potential SO if you weren't prepared to reveal this integral and intimate part of your personality.
Good luck :hugs:
Katey x

[Kagji]

They can in the right circumstances, but for this one... It sounds like you're gonna have to choose. Sorry, doll. Hope it goes well.

[Lacey New]

Not that I would advocate it - but Lacey lives in a small stash carefully hidden in the attic. She only comes out when the missus of 20 years is away or when Lacey gets to travel and buy new things. But Lacey has learned to live like this and it is her compromise.

[Erica Marie]

Omg. Sounds if you are reading my story. I honestly dont know what to say. I told my exgf after 3 yrs and It didnt go so well. But she had other motives besides not accepting my dressing.
Old flames are easy to reignite but hard to keep burning. I honestly wish you the best.

[Alexis.j]

I would let her know asap, but thats just me. She might not accept it, but its better than telling her later when thing get too serious, then the whole lie/dishonesty/trust issue comes in, and its not nice...
I am not actively looking for a partner at the moment, it would be nice, but she would have to support my feminine side 100%.
There is an old 'girlfriend/good friend' from before my getting married days, that I am seeing quite a bit of lately. But she has always seemed a bit too 'vanilla' to me. Next step is to tell her, whatever happens, happens...

If someone does not like me for who I truely am, they are NOT worth having as a friend. And I will rather be alone than with someone that doesn't support me, period.

[Marcelle]

Hi Toni,

I guess my question for you is . . . Can you really give up Toni again? You indicated that you spend 20+ years without her but found her again. To me that is a strong drive to dress. So, if you move forward with the relationship and can pack Toni away then not an issue. However if you cannot, how long before Toni needs to get out again and how will that go over in your relationship.

In the end, it is a choice only you can make. If you feel you can successfully hide Toni or remove her all together then move forward. However, if you don't think you will be able to hide her well enough then . . . it might require some communication beforehand.

Hugs and good luck.

Isha.

[CarlaWestin]

How about, "Vanilla. I really have good feelings about you and me being together AND there is something I have to tell you. I'm a crossdresser." Unless it is out it becomes more of a betrayal the further into a relationship you get. Unless you think you could quit and not quietly obsess over every thing female you see, from now on.

Ooo! Wait! I know. How 'bout if you casually mention at the right time, "You know, I've dabbled in a little crossdressing before." Her immediate reaction would speak volumes. And I would seriously be aware of the faux acceptance early in the relationship turning into disapproval after the leash is on. I've been screwed by that one a few times.

Anyway, I say some level of disclosure is paramount unless you want to lurk in the shadows and be dishonest to her, and yourself.

YMMV

[Lynn Marie]

So you are already in a loving relationship with Miss Vanilla yet you have this secret you're afraid to tell her. How does that feel to you? Maybe like a wall you're hiding behind? You want to marry this sweet soul while keeping from her an extremely important part of who you've been and quite probably will continue to be. Sounds pretty selfish and deceptive to me. Do you really feel you're being fair to this "vanilla" person. How would you feel if you found out sometime down the line that she was really a boy who'd transitioned into a lovely vanilla girl!

[Lori Kurtz]

As often happens here, you're asking questions no one but you can answer. But since you asked, I'll add my response; I think it's smart for you to gather other opinions. You've been here long enough to know that there are CDers and TG people who are in successful relationship with aware and accepting GGs. There are not many such GGs, but they do exist. So it is not impossible that you could reveal the truth to Vanilla and continue in a relationship with her. Maybe not likely, but still not impossible. For me, as I stood at the crossroad where you are now--looking at the possibility of a new and wonderful relationship after my first marriage failed because of my CDing--I decided not to reveal that aspect of my past, and not to include CDing in my future. For me it worked--but I would never say that it could work for everyone. So I'd urge you to consider just two options, as you think about which way to go. You can reveal Toni to Vanilla, and hope that the three of you can find a way to live together (one of the risks of which is that Vanilla honestly thinks she can accept Toni, but discovers later on that she can't), or you can commit yourself to giving Toni up altogether (and the risk there is that you later on discover that you can't). The option that I'd urge you not to choose is to continue with both Toni and Vanilla in the hope that Vanilla will never find out about Toni. There's too much risk of pain for both you and Vanilla if you go down that road. That's like starting your relationship with Vanilla while continuing an affair with someone else. Now is the time to make a decision. The longer you wait, the harder it will be. Best of luck to you, whichever road you choose.

[Majella St Gerard]

If you know that she would freak out about the CDing then how could she be the one that you can spend the rest of your life with. You will just be making the same mistake again. CDing is not something you can just stop, as you well know. Don't set yourself up for a major fall. TELL her before anything goes any further, if she REALLY loves you, nothing that you wear will have any effect on that. But you MUST TELL HER, starting a relationship with this big of a secret hanging over your head is not the way to marital bliss. She WILL find out and then what? Keeping secrets did not work in the past and "killing off Toni" will not work cause Toni is one of the un-dead, she will always dig herself out of her grave and stalk you. You can bet on that. Tony can only be happy with Toni in his life, you know that to be true. Good luck and sorry for the rant.

Peace & Love

Majella

[Desirae]

Feel her out over a few months. What's the big hurry, anyway? "Steer" discussions with her towards crossdressing or even transsexualism. There are bound to be some shows coming up on TV that will be about one or the other, whether they are talk shows, movies, news, etc. You may see an article in the newspaper somehow related to CDing or similar. Start reading it in front of her. She's bound to ask "what are you reading, hon", or something like that, and you can gauge her reaction that way. If you don't see any kind of reaction from her while you are reading, viewing a TV program, whatever, let out a little chuckle, sigh, a "hmmm", whatever, in order to steer her into giving you an opening to see her reaction. Wait until you have an idea of what "she may think" about it before you broach the subject with her about your CDing.

It's a win-win for you. You either find out that she's OK with it or you find out she's not, in which case she isn't the one for you then, anyway. I don't think that trying to keep it hidden from her while pursuing a relationship with her is the way to go over the long term.

[Jenniferathome]

You are in a far better situation that most. As a "friend" she is far less likely to react strongly. She's just your friend. She may hate it, may find it curious, whatever, but it's outside of her. Once IN a relationship, the revelation will take on a new level of seriousness. She cane far more objective today, than after she moves in....

[Tina B.]

First, you don't say why you broke up the first time, and what's been going on for 20 years that you didn't dress, but with no more information than we have, I'll venture to say, I've seen more than one couple "get back together", just to find out they where both the same people that had been before, and why that had split up the first time.
Even and old love, is a new flame when you have reconnected, slow down and pay close attention, We know you can give it up, if you did for twenty years, but where you happy not dressing for all that time? I've gone as long as 5 years without dressing, but happiness had no part of it, that's why I dress now.
I told my wife many years ago, and she accepts me for who I am, so yes, it can work, and yes there are women out there that love and even protect their CD husbands.
Marriage if done right is a long term proposition, and not something that should be rushed into, when it works, nothing is better, but the other side of the coin, when it doesn't work, life turns into a loving hell.
Be careful when playing with an old flame, you could get burned.

[Karren H]

Present her with a Pre-nup.... that lays out just what rights you have and what your allowed to wear and when.... and who gets all the lingerie if you split up.... that should get the discussion going....

[UNDERDRESSER]

Several points here. How long has it been since the divorce? How well do you know this friend from old, when she has spent 20 years out of your life? You knew her then, but are you the same person of 20 years ago?

Here's the big one, can truly give up CDing? From what I've read on here, it isn't so easy. if you can't, and she finds out later, she will be even more upset that you have taken away a chance to be settled so late in life. Another question, why is she free now? Another divorce? What was behind that? My situation was slightly different, and I knew my GF was very open minded, but the risk was still there, but I couldn't go into it hiding this from her. But that's me, think carefully....

[Toni Citara]

I guess the background should have included "divorced since 2009", have dated several women, only three were serious. The particular vanilla was somebody I dated in 2010 but timing was wrong for both of us and she moved to another state for a job, we stayed in contact and talked quite a bit over the years. The last few weeks we discussed getting together and this past week I visited her and her family. Dinner at the parent's place, etc. All went well, just not sure I want to ruin this relationship. You all have given some good advice, and I'm thinking I need to have "the talk" with her. Probably something easy, like pics from halloween.

[5150 Girl]

Ya know what, This is an age-old story on this forum... You know deep down, if yu give up Toni, Tony is going to be miserable.
You have to tell her if you want to be happy.
Besides, she might surprise you! Sometimes a staunch "vanilla" appearance on the outside, is often a cover for a "kink monster" buried on the inside!

[Tracii G]

She does already know you to some degree so maybe this part of you won't change her opinion of you as a person.
I believe it helped in my case but we are more a good friend couple no sex involved.
She wants it to be more than that but she knows I don't and she accepts that.Yes we have had the long deep talks and she knows where I stand.

5150 Girl makes a good point too Miss Vanilla may have another side as well .:)

[Cheryl T]

Be honest and upfront with her. Better she know now then "discover" you later and feel deceived.
If it's meant to be then it will be.

[DebbieL]

Don't begin a new relationship based on deception. You say she loves you, you say she is vanilla, you say she would not accept you if she knew.
How do you know? She might be attracted to you BECAUSE of your feminine aspects.

You really need to decide if you want to continue trying to keep presenting only your most masculine persona to women. If you are willing to show your feminine side, watch romances and romantic comedies, listen and share your feelings rather than trying to "fix it", and willing to share your gentle and softer nature, maybe even scratch her back around the bra line, she will begin to wonder, and even ask you.

Most women are terrified to ask us if we are CDs or TS because they don't want to threaten a fragile male ego. Some women actually seek out more effeminate women and are rejected when they suggest that their man might be feminine. Some men even become violent.

If you let her know up front, as early on as possible, you will either have a wonderful and loving relationship in which Toni is fully loved and accepted, or you can move on to meet women who actually WANT to meet a girl like Toni.

Shortly after my first wife moved out, I started going to dances and other social events as Debbie. I also told 12 women about being transgender. Pretty much I said "I'm a girl on the inside and a boy on the outside". It took about 3 months for a very small group of women to begin seeking me out. They wanted to be introduced to me BECAUSE they knew about Debbie. Even when I was out as Rex, women friends would introduce me to women who wanted to meet Debbie. I ended up in a wonderful relationship with a woman I loved for almost 2 years.

A few months after that one ended, I met another woman and we were together for 15 years. She didn't want to get married, but she loved Debbie. In fact, she loved Debbie and was less fond of Rex. Eventually we ended that relationship as well.

Eventually, I started thinking I wanted to get married again, so I put an ad in a few personal sites including Match.com. About a thousand women viewed my profile. about a dozen showed interest, and 6 resulted in dates. One of them turned out to be a great catch, and we ended up getting married. I might have gotten even more positives if my cover picture had been of Debbie, but I made it one of the extra pictures instead. Women would see an average looking man, and if they found HIM attractive, they would be less interested in HER. If I had gone the other way, putting the profile in "Men looking for women" with Debbie on the profile, there would have been more bisexual women who would have jumped at the chance to meet someone like me, and would have been reassured by the pictures of Rex that I was still male.

Consider taking a few subtle steps to show more of your feminine side with women you are dating. Have both of your ears pierced and wear CZ studs. Have your nails manicured and wear a near natural nail polish. Men might notice but won't say anything. Women will notice and will compliment you, to see how you react. If you thank them graciously and compliment them, they will often show more interest, maybe not for themselves, but perhaps they know another man like you, or even better, a woman who is looking for a man like you.

Many women actually WANT a more feminine man. They want someone who is softer, gentle, listens well, isn't afraid to share their feelings, doesn't have a fragile male ego, and will let them take charge - where they want to have the feeling of more control. This may be just in the bedroom, or perhaps even in the area of social calendar, finances, and security. In effect, they want many of the perks and privileges of being the "Man" in the relationship. At the same time, they want the stability and social acceptability of a heterosexual relationship.

Keep in mind that when I put out my ad, I was heavy (270 lbs), older (49), and had a nice income but by no means rich.

I was also more flexible about the women. I had been doing this long enough to realize that I could be much happier with a woman who was a bit heavier, maybe not as feminine, but really enjoyed Debbie, than I would be with a woman who looked and dressed the way Debbie wanted to look and dress, but didn't like Debbie and wouldn't go out with Debbie because Debbie had better legs.

Don't continue to build a relationship based on deception and secrecy. If she runs for the hills, she probably could never truly love you. Toni is part of who you are. She may not be your "True self" like with a transsexual, but she is still a dear and cherished part of who you are. If she can't love Toni it would be a risky relationship anyway. DADT is what couples do when the woman can't accept her husband for who he truly is. The girl is in there, screaming to come out and play, but the wife wants to keep her locked in a closet, hidden away from the world, hoping that she will die.

Do you want Toni to die? Do you want to stop cross-dressing forever? Do you want to stop something that was so important to you even after 20 years she came back to life, demanding to be given life again?

You probably should see a counselor to try and figure out how much is Toni and how much is Tony. There is a whole spectrum on the transgender scale, from the fetishist who only wants to wear specific items and only for sexual stimulation to the type 6 transsexual who becomes self destructive, even suicidal when forced to conform to birth gender. You fit somewhere in the middle, and may shift to a higher level now that you no longer have the constraints of a spouse who could never truly love the real you.

If the relationship dies when you bring up the cross-dressing, it was dead before it started, and you just found out. Would you lie to a woman about your profession? Your assets? Your social status? Would you tell her you were the CEO of a $billion company when you were actually a respected professional with a modest income?

Being deceptive in the early stages of a relationship is normal, but too much distortion doesn't last long. She might wear the short skirts and heels for a few weeks, but if she is uncomfortable in them, you will be able to see it as you reach the end of the date and she seems to hobble back to the car and kicks them off the second she gets seated in the car. You will see it when you go shopping together and she keeps choosing the comfortable clothes instead of the flirty and sexy ones.

If you take her shopping for something pretty and she holds an item up to you, make sure you give her a really big smile. If she smiles back, you know you have the beginning of something wonderful. It the idea doesn't even occur to her, you are either being too deceptive or she doesn't want to acknowledge your feminine side.

[Lorileah]

In my opinion, if you start compromising yourself before you start the relationship, you will end up regretting it later when you are deep into the relationship. I would not keep any secrets that may, later in the relationship, come out. Maybe what I am saying is would you rather be sort of happy alone or miserable with her?

I would like a partner but I am at he point in my life that I am the one I know I will be living with forever. While I would do what I could to please her (or him) doing so at the expense of my happiness is no longer an option. I had two wonderful relationships with two wonderful women, and yes we compromised on some things (the last compromised a lot FOR me and I regret she had to do that), but both allowed me to be "me". No major changes in who I was.

[Debra Russell]

Just put on your big girl panties and "man" up you'll feel better and know where you stand.......................Debra

[mary something]

You'll never know if she could go for it if you don't try. If you guys are already being physically intimate then now would be a good time to mention it casually. I wouldn't show her pictures unless asked or go to far into details about it until she is ready. If your heart is starting to think she is the one then now is the time to disclose it before it gets too difficult to do later and the stakes are too high. She already knows you well as a person, make sure she understands that this is just a part of what makes you who you are and that it will always be at least a small part of you.

I told my partner when I knew that I liked her enough that I wanted to see if we could be intimate emotionally and physically. If she is into you then she will want to know all of you, and you know all of her. She will probably appreciate a partner that is sincere, honest, and emotionally available because she knows all of you.

My fiancee had no idea of the difference between a crossdresser, a transsexual, and a gay man three years ago and I would have described her as fairly vanilla at the time too. Now she is my biggest supporter and our relationship is better than I thought was even possible. Neither one of us is the bdsm type, but there is nothing vanilla about our sex life and it really works well for both of us.

Try not to assume that this will end the relationship, you don't want her picking up that vibe and thinking that you're trying to run her off. I think it was about a month or maybe two after I told my SO that we had our first trip together as two women. If she is really into you she will want to accept this if that is what it takes to have you with her. Good luck!

[ginger22]

I'd recommend listening/reading to Dan Savage (thestranger.com) if you haven't. He's addressed this a few times. My experience is that in the early days of a relationship, people are open and ready about their new boyfriend/girlfriend. This isn't a first date topic, but it can't wait a year either. For me, once we got physical, and started talking about sex, I shared that I LOVED the feelings of stockings. And that I'd always dreamed of stocking on stocking sex - that night became my first time for that.

If she's not open to that, you can do better.

[chrissy111]

I'm in full agreement with Alexis, you need to tell her right away. You owe it to yourself and her.