Dating as a CD?

[Maid_Marion]

I don't see a lot of posts on Dating as a Cross Dresser.

Since I've been wearing clothes often regarded as feminine I noticed that women are much more friendly and approach me.
My guess is that they are attracted by flashy outfits and the confidence it takes for a guy to wear a skirt out in public. Or tending the roses in his front yard.

I do know that when I dressed poorly as a short guy I was ignored in public. I was too small to buy clothes that fit properly. Boys sizes had much more fabric than an XS woman's top that I now wear.
An XXS men's shirt is purely hypothetical. Nobody actually makes that size. Nor did I have any luck on dating sites. My short height was a non-starter according to many opinions about match making.

As for being six months from being on HRT, I don't see the health risks as being worthwhile. It is likely that my big collection of tops won't fit properly if I gain a lot of bust size.
It is great being my size and shopping for clothes. I think they tease women with pretty XS clothes they can't possibly wear.
I can look at myself in the mirror wearing a bikini without any dysphoria. My wife couldn't pass that test.

Marion

[Marketa]

I don't have any experience with dating as CD (yet), but I have some experience from clubs and as a CD it's definitely much easier to get someone for...let's call it "happy times in bedroom". And I mean men just like women.

[Roxy]

I've been out of the dating seen for 18 year. Earlier this year my wife passed way and I find myself longing for female companionship. Other than online friends, my wife was the only one that knew of my crossdressing, I told her when our relationship was starting to get serious. She accepted it as part of me but wasn't fully supportive.
The thought of dating and going through the same awkward conversation again is not something to look forward to...even listing it in my profile on a dating app doesn't sound good.

[docrobbysherry]

Me dating men when CDing at age 80 No problem!

Me dating women when CDing? Ain't happenin!

I get plenty of support and attention when out clubbing from women. But, it's NOT because they have any interest in dating me!

[Sandi Beech]

I agree with the last post in that most women are generally supportive but only a small subset of them are interested in us. I had one woman tell me I would make the perfect husband, so there are some out there. I never wanted any relationships with people I met, but I know it would have been possible.

Sandi

[AmyJordan]

Roxy I'm so sorry to hear you lost your wonderful wife recently I'm not sure what I would do in a similar situation.

I've been feminised too much to easily forget everything and go back to being fully male and I'm only into women so what would the chances be of another woman taking me on I would say very very slim.

I don't envy anyone in the dating scene nowadays let alone those off us who may be slightly different.

Amy x

[JulieC]

Ever heard of the Drake Equation? You can use it to take a guess at how many planets there are with intelligent life in our galaxy. There are variables which successively divide the numbers of possible planets down until you arrive at a hypothetical figure.

There should be a similar calculation for dating. Imagine (these all take guesses);

1. How many adults within your preferred range from your physical address?
2. Are you hetero/bi/gay? Segment above population into what you are attracted to of the entire set.
3. How many adults are there within years above/below your age you are willing to date?
4. Estimate of what percent are not involved in a committed relationship and thus available
5. Estimate of what percent are interested in potentially dating someone
6. Estimate of what percent of those might be interested in you
7. <insert other segments>
8. Percent of people in your target population who would be cd accepting to a level you would accept

Running it for me; (1) oh, say 1 million, (2) hetero, so guessing that puts at about 425,000, (3) looking at national figures and calculating from that, I arrive at 14.85% so 63,112, (4) guessing 20%, so 12,622 (5) guessing 75% so 9,467 (6) say 1 in 20, thus 473, and for the segment, the cd segment, say 10% thus 47. 47 people out of 1 million in my general region whom I could potentially date that would be supportive of my crossdressing. Chances of meeting such a person? Hard to say, but not high.

There's lots of variables. But, the last one certainly has an impact on the potential pool. Are such people out there? Yes. Are they easy to find? Hard to say. Of the women (I'm hetero) whom I have dated who have known I crossdress (4), three have been supportive, and one was very, very non-accepting. A fifth found out many years after we dated, and has said it would not have caused us to break up. A sample set of 5 isn't a big set. But, 4 out of 5 is not too bad.

Roxy, I'm very sorry your wife passed.

For my part, if my wife passed away or we divorced (extremely unlikely), I doubt I would ever date again. Like you Roxy, I don't know that I want to go through all of that again to find a woman who is not just accepting, but supportive. When I met my wife and started dating her, I felt I could marry someone who at least accepted, and crossdressing didn't cause problems. My wife is that and more. I wouldn't want to be with someone who wasn't at least as supportive as my wife anymore. Time is short, and I am who I am.

[Gi Gondin]

It’s hard to find someone that fully respects you. And i’m not talking about crossdressing.
Is it worthwhile to search and find? In my opinion, yes.

It took me 3 marriages.

[chrissy111]

Very sorry for your loss. Not sure how I would handle dating if something ever happened to my wife. I think I read that there are dating sites for us, so at least the women looking there are at least interested in us. Good luck.

[BiancaEstrella]

I'm on the other side of this situation - long-time crossdresser, out as trans now for several years, interested in dating crossdressers.

I struggle with three things, I'll get the first one out of the way quickly: there don't seem to be many crossdressers local to me

The other two are deeper issues, and the first one is on me. And it's that I don't know what the dynamic becomes once my sweetie is no longer presenting as a woman, since I've never been attracted to conventional, manly-man masculinity. I'm not entirely sure how my brain would process the shift. I think I could manage it, I just don't know that I could, and I wouldn't want to put someone I adore and cherish in a position where they felt they had to dress more to appease me. I'd obviously be open to seeing his more feminine side as much as he wanted to partake in it, and I'd certainly stay if it turned out she wanted to be full-time, but also I wouldn't want to feel like I ushered in, demanded, or overly influenced a transition. I believe in myself, and in my 41 years I've surprised myself at what I've been able to do in multiple ways, but the other issue is I'll be in conversation with a crossdresser online (again, can't seem to find any local to me) and they think I'm either a bot or that I'm a real person but I'm stringing them along, just saying what they want to hear instead of expressing sincere feelings. The threat of being catfished is very real, but it does hurt when I'm accused of doing it then the conversation that I was actually enjoying just shuts down. I'm a mess

[Fiona_44]

Women are much more likely to be respectful to MTF CD's and trans women. However, the percentage of women who would be okay with dating or marrying a CD is very, very small.

[Maid_Marion]

It is a numbers game. How do you meet women? And let them know you cross dress?
This seems to be the biggest issue is that many CDs only let a very small number of people know and aren't comfortable with telling their friends to tell everyone else that you are a CD.

My approach is to spend more time socializing dressed. Which isn't hard if you are confident enough to go full time in activities such as golf where you have an opportunity to practice talking about yourself so "the conversation"is no longer awkward.
Like everything else, constant practice is needed to become skilled at talking about yourself.

I've been giving away roses to give me more time for playing golf. I recently spent half a day with an accountant who is going to plant many of those roses in a historical house.
It turns out that I have great one on one teaching skills when it comes to growing roses.

I think it is important to avoid "bait and switch." Advertising yourself as "normal" when you aren't. I think folks should know up front that you dress.

When I was married we talked about everything and set boundaries. Labels aren't as important as discussing the how far you can go and what sort of relationship you expect to have.
I think to many women the functional difference between Cross Dressing and Transgender is HRT. If you are on HRT you are Transgender. If you aren't you are a cross dresser.
My wife and I set that as boundary. Dressing is OK but if I wanted HRT we needed another discussion.

There is a great scene in Crazy Rich Asians in which a couple separates because the guy can't deal with having a rich and powerful wife. She goes shopping and has to hide her purchases, some of which are worth more than a house.

[chrissy111]

I'm 100% with you on being honest and up front about our life style. It doesn't go away so if you want a serious relationship with someone it's imperative to start out honest.

[Maid_Marion]

Yes, the key issue is honesty. Women need a partner they can trust.

Woman can compromise better than men. They have to do that all their lives. Just read some romance novels about the tough choices they have to make. Wealth, power, sex. Pick any two. Guess which ones women normally pick?
Guys have a much different set of standards in selecting partners and make different compromises.

Health is also a big issue. When I brought my wife into hospice the nurse told me that a lot of husbands don't take as good care of their wives to the very end. She said I should be proud of what I was able to do for her.
Mental Health issues often have drugs with side effects that affect relationships.
I wore a skirt to a rose show and a woman approached me, looking for a "white knight" if I"d be interested in that sort of relationship to help her rebound out of a bad one.
Instead, I played a really bad but enjoyable round of golf.

[kellyanne]

My experience has consistent with Fiona's observation. I have dated women dressed but only behind closed doors and we were casual lovers w/o a public face as a couple.

My real lesson in this came when I dated my HS sweetheart after we finished university. She was the most liberal woman imaginable , basically a gay and trans rights activist before it became in vogue and to this day , I guarantee she would go to a pro gay, trans protest etc but in no way shape or form did she want her man to be anything but traditional in gender relations and financial success.

" As long as there is no role reversal"

I was overwhelmingly shocked by her dim view after so many years knowing and dating her and her " public face" as a staunch liberal.
Since then I have kept my cards close to my chest and resigned to being single since I cannot change who I am and knew the odds.

[sweetdreams]

I have a little experience dating and then revealing my crossdressing. None where I presented as a CD right from the get go. Generally it was discussed as things got serious. I've shared these before but it's been a couple of years. I thought I would share the abbreviated versions for anyone who hasn't seen them before.

At one point my wife and I hit a rough spot in our marriage after about 20 years. We ended up divorcing, but then three years later remarried to each other. In that 3 year break I did actively engage in dating and my CDing was a factor in any new relationship. I promised myself it would be on the table, in the open before anything serious happened.

I casually dated one girl who was very open minded. We never got far enough along to get really serious and it ended as quickly as it started. While we were getting to know each other, there was a Halloween and I was invited to her house for the evening. I decided to wear a skirt, top, and the appropriate under things and see the reaction. No wig or makeup, just a guy in a dress. She was surprised when she opened her door. Her initial response was "I wondered if you had a creative side to you". There was some pinch and tickle that went on. She felt my legs to try and figure out what brand of stockings I had on. She got one of her wigs and put it on me. She wanted me to strip down to my underwear, but I was too shy (foolish me). At the end of the evening she asked if I liked dressing up as a girl. I said I did. She told me to hang on to the underwear (stockings, garter belt, and panties) and we would have a girl's night out sometime. Shortly after this we just stopped seeing each other.

The second girl I dated during this period was a much more serious affair. We dated for several months. Then she asked me to move in with her (she had two kids at home as well). At this point I had to have the talk with her. I told her I crossdressed and it was and important part of me. She took that away to digest. She didn't freak, wasn't turned off by the idea. She thought about it for a few days, talked to her psychologist, and said she was fine with it. No problem! One night she was coming over to my apartment and I decided to put her to the test. I got dolled up and answered the door fully en femme. She smiled and was fine with it. Wouldn't you know it, the ex phoned right at this moment in time. There I am standing in front of the girlfriend fully dressed, phone in had, having a somewhat lengthy conversation with the ex. Finally got the ex to hang up and walked over the my new girlfriend. The first thing she does is slides her hand up my skirt to see what I had on underneath. Then she takes me by the hand and we go into the bedroom and let nature take its course. All is better than good. I did move in with her. The first night of me living with her, she laid out a nightie and panty set on the bed for me. The rest of our relationship was along these lines. She was actually turned on by my dressing and if I was all dolled up she couldn't last more than about half an hour before we were in the bedroom. She even shared clothes with me. We did break up. I moved to a different country and wasn't happy with some things in the relationship. After about a two year relationship it ended but not because of my CDing. I could go on with more things that happened in this relationship but I want to keep it short. Nothing was too girly for her and I never had to worry about her acceptance and participation.

The ex and I did get back together. When I moved to the new country she realized she might never see me again and reached out to me. Over time we worked out the issues. She had to divorce someone she married. We remarried after about a 3 year break and that was over 20 years ago now. My CDing is part of our relationship and really not an issue at this point. All is good.

I'm sharing these stories with you to point out that there are girls who are OK with CDing, and sometimes even more than OK. Personally I wouldn't enter into a relationship where my CDing didn't have room to exist. I just wouldn't live that way. We all have our sets of values and what we are willing to live with. For me, CDing doesn't have to be kept in the closet.

[kimdl93]

After two long marriages the ended in divorce, and now in my 70s, I have little interest in dating. I figure I have made enough mistakes in 40 years of relationships for a lifetime.

[AngelaGA]

I'm in my late 30's and It has been hard for me to date as a CD. both male and females. Ive tried and paid for dating apps and still no luck. im on the verge of giving up.

[Philippa Jane]

I am still looking and being hopeful, however I am being a lot more guarded with my feelings.
I have a lot of female friends but none of them have that little spark.
I make no bones about what I am so there is no thoughts of deceit.
One woman who has read my story went out of her way to stress that we were Just friends.
That was OK by me but I did smile inwardly at how presumptuous her thoughts were.
One friend this weekend went so far as to say that I passed so well up until I spoke. My voice is the give away. This now has me thinking of a trachea shave.
I still don't think any of them would want to date me.

[Maid_Marion]

I was wearing a dress when I announced I was planning to retire in six months at the company dinner. I let the people I worked with for a long time know first. One lady half jokingly asked whether I'd be interested in her. She only a little bit taller than me but notorious for only dating really tall guys. She had a marriage that ended after only one month and she raised a daughter with the assistance of her mother. Would she now compromise her romantic interest in tall guys for a retirement funded by a large investment portfolio?

LastDay.jpg
These are the clothes I wore on my last day of work. I've now been retired for two years. I'm now playing golf three times a week, weather permitting.

I chatted with a black guy who mows the public golf course I practice at twice a week because it is cheap. I wear same expensive clothes I wear to the private country club once a week.
He told me he though I was a girl! He asked a couple of questions, including whether I had any interest in guys. I told him I was only interested in dressing because I liked shopping for clothes and men's clothes didn't fit.
I figure that is an honest answer since the I've been living alone for ten years and have yet to go on HRT. To me that is the dividing line between transgender and cross dressing without getting into the weeds that only we understand.
If your plumbing is intact and fully functional and not affected by HRT you count as a cross dresser.


I've had many conversations on the phone that suggest my voice is totally passable as female. Telemarkers don't have a clue as to whom they are speaking!

Marion

[OrdinaryAverageGuy]

I gave up on the dating scene years ago, and accepted the fact that I was going to be single the rest of my life. And then I met my now-wife. God willing, I'll never go on a first date again!!

[Mari]

I've had one relationship in my life, which was a long-distance relationship with a trans woman in another country. She was very supportive and encouraged me exploring my female side. After that relationship came to an end, I've had zero luck finding anyone who would even consider me relationship material even in male mode, let alone as a CDer. I'm pretty sure I will die alone at this point.

[TheHiddenMe]

I am married so I am not dating, but I will throw in my two cents.

I have met women who've had issues with men being jerks (I probably shouldn't use the word they use to describe men). I think if you bring enough positive qualities to the relationship, a woman might be open to dating a CD. If I were out in the dating pool, I think I'd be pretty upfront about my dressing, because you might as well know up front if it's going to be an issue or not, and they so know up front.

Tricia Lee seems to be doing ok on the dating front, so it's not completely hopeless.

But if you don't try, you're not going to get. You have to be willing to ask and get a no.

Just like when we 18 and working up the courage to ask a girl out. Only, that fear left me a long time ago. There are some benefits to age.