Close this search box.

The New Dilemma

We open up the floor for discussion....

By Cali

Let me first give a little background to this tale. I have dressed since pre-teen. My first wife knew about it since she came home unexpectedly one day. We divorced for completely different reasons. My second wife knew about it but I had little time for anything. Again, that marriage ended over (again) completely different reason. Towards the end of that relationship, my urologist suggested I wear ‘bikini style’ underwear. By chance my then wife put some of her underwear in my pile. Pick them up, put them on in the dark and … never wore male underwear again. I started to purchase women’s versions of clothing.

Since then, I now live alone, wear high heels, almost all women’s clothes, and have exquisite nails while working in a profession career. The heels, clothes, nails are here to stay. Besides I’m too far down the rabbit hole to change.

Now for the Dilemma. I’m starting to date and I debating in my head (over think it) the what, where, and whys(?). Then the HOW sisters: HOW much and HOW soon, to tell her.

The plan so far is ‘hoping she brings it up because of my long gel nails’ followed by ‘her asking more questions’. Great plan?

Any suggestions, any better plans.


18 Responses

  1. Cali, given the heels, clothes and nails, probably the only questions on her mind are ‘how far does this go?’ and ‘how far is this going to go?’. The only downside I can see to your plan is that the issue becomes the ‘elephant in the room’ – you’re not talking about it because you’re waiting for her to ask and she’s not asking because she’s worried about offending you.

    Given the obvious signs, I’d just start the conversation with ‘you’ve probably noticed….’ and not put off something that (a) is probably a non-issue for her and (b) gives you the opportunity to exploit things in common (possibly the contents of her wardrobe if you’ve gone for someone of similar build!).

    1. Thanks for you input Amanda. There are a lot of tales of married members and their triasl and tribulations with their wife, so I felt we needed to look at this from a different angle. I wrote this piece before the first meeting with a new potential partner a few weeks ago. I did bring it up first with that woman, but we were not a match for other reasons. So the search continues.

  2. Cali, Very good advice from Amanda. I have known you for a long time and you are not the shy type, I think, so just do it. The sooner the better.

  3. Cali,
    She definitely has noticed your nails and other feminine touches. Since she’s still around she appears to have some degree of tolerance for you being you! Definitely start a conversation. Maybe see if she wants to get her nails done with you??

    Good luck -Sherry❤️

    1. Hi Shery,
      This one was a blind date, we went out to do an activity. All she knew before we met was I wore 4 inch heels most of the time. My nails were obvious upon meeting, and much better than her’s.
      As for getting our nails done together (with anyone), it can’t happen at my nail salon. I have been with my nail salon for over 10 years, its a small 2 person independent contractor shop. They are currently booked out through August, accepting no new clients or walk-ins.

  4. So I’ve just gone through this most recently with a lady I’m dating, I knew as we got closer the conversation had to happen
    I just told her flat out I dress and that I’m mostly fluid at my job.
    So far it’s been good she had lots of questions and I gave her some suggestions on books to read about this lifestyle as it were.
    So if you do think it’s getting deeper yes it’s important to bring it up
    I wish you well

    1. Rachael,
      You are very lucky to find a woman who doesn’t turn and run at first sight. So many say they are open minded, etc. until it’s in their own backyard. I know this is who I am, and don’t want to live my life in the closet. Besides, I need the acrylic nails to keep my nails from splitting to the root bed and I need my heels for hip pain relief, so those things are non-negotiable.
      Thanks for the reply,

  5. Hi Cali,
    Well so far it appears that you have a consensus from us. I totally agree with the other girls. The sooner you bring this up to her and have the discussion the better it will be for both of you. You should be the one to start the discussion, don’t wait for your partner to. Good luck and best wishes that it all goes well girl.

    Trish ❤️

    1. Hi Trish,
      I don’t plan to throw everything at a potential mate at the same time, And I will answer any she ask. If she ‘runs’ because of the heels or nails, then it saves me time and money. I am encourage by the relationship some of the members here have. So, I an hopeful.

  6. Cali,
    I don’t feel you can go down the road of suggesting you wear heels and female underwear for medical reasons , there would be obvious alternatives for men with similar conditions .

    You need to ask yourself what the dressing really means to you if you have dysphoria then it’s a reasonable explanation but without that explanation most women would consider it a fetish . Consider for a moment how you would feel if your new partner started wearing male clothes for no apparent reason , OK I accept some women cannot wear heels for medical reasons .
    If you do have dysphoria then it should be explained to her before things go too far , she has the right to know before she commits to a relationship . I’m going to suggest from you saying the heels , nails and clothes are here to stay you do have dysphoria . Please consider these items aren’t the full picture to living as a woman , I’ve discovered there’s far more to the situation .
    If all the cards aren’t laid on the table then your looking at another failed relationship .

    I know and accept I have dysphoria , to deal with it I live happily as a woman , if I enter a relationship I’m faced with a similar dilemma because I’m still physically male . I’m seriously considering if I really need a close relationship at my age and come to the conclusion that reliable , close friends without complications is a less streesful choice .

    1. Teresa,
      I am held together with 7 three inch screws and metal plate. My injury damaged my bladder and other organs. The only other suggestion from my urolgist (head of urology at a major university hospital) was a mechanical device and diapers. I lived for 11 years in constant pain – like a constant hip pointer that would get worst throughout the day. After another injury, I had to raise my heels 4 inch for my calf to heel and to even be able to stand and do things like wash my dishes. Friends told me that I didn’t memtion my hip while in heels. After 5 months of not walking much, I tried to go back to flats and the pain came back in a week. If I do an activity that requires flats, such as deep sea fishing, then I pay the price that night and need pain (real strong) medication. So it doesn’t matter to me if she believes me or not, I have to live in this body. When you work hard and play even harder sh_t happens.

        1. Teresa,
          I have had several rare and/or uncommon injuries. So I can understand your suggestion that I have dysphoria.
          I have women’s shaped feet. The last fact I found out after many ankle reconstructions caused by wearing men’s shoes. I haven’t had an ankle problem since switching to women’s shoes. When I blow out my calf I was already wearing women’s shoes, so finding and wearing high heels was easy.

  7. Cali, the best thing to do is talk about it as soon as things get a little bit more serious. Open communication is the best solution, I wish I would have communicated better to my wife. I am not sure things would have changed, but It would have made me feel better even if we ended up in situation I find myself in now. Good luck girlfriend.

    1. Thanks Julie,
      I see so many people here live under different conditions/rules and I don’t want a relation like that. No disrespect to others, but I don’t want to hide ‘Cali’ to have a relationship. My heels and nails are here to stay. Some might say I want my cake and eat it to.

  8. I think early disclosure is the best course of action, and that means you bringing it up instead of the other person waiting to ask.

    Let’s face it; there’s over a 50% chance anyone you meet is going to be online, because that is dating today. You make contact, then start texting, kicking the tires or whether you want to meet. I think the earlier you disclose in the back and forth of texting the better. Explain your reasons as you’ve done here. Better to find out early and not waste either yours or her time.

    I have met women because I go out dressed. One of my GG friends tells me “men are assholes.” My answer was “true dat.”

    If you can prove that in addition to the nails and heels and dressing that you are a nice guy and a decent human being, you might have a shot with someone who IS tired of dating assholes. The dressing might be the price of admission for them to be with you, and they accept it because you bring other positive qualities to a potential relationship.

    I believe, based on my interactions with women I’ve met while dressed, that if I were on the market (I’m married, so I’m not), that I have enough positive qualities women would be interested in dating me, despite the dressing. And if they found me interesting BECAUSE of the dressing, bingo.

    In short, because of all the other creeps out there trying to date, by being honest they might give you a shot. You will never know unless you try. But I think telling early is the best action to take.

    Good luck.

    1. Dee,
      That’s why I ask you about your bestie Michelle’s opinion on men with nail color – because I wanted the opinion from a salon owner who was single and (I assume) looking.
      The only thing I could add here is that some women (men) keep going back to that asshole type.
      And my on-line dating profile does state I wear 4 inch heels and one of the photos shows fingers with color nails.

Leave a Reply

Your email address will not be published. Required fields are marked *

Featured Posts

Get The Latest Updates

Subscribe To Our Newsletter

Sign up for the first look at Kandi’s outfits, blog posts, and product recommendations.