The Plight of the Single Crossdresser...

[GeminaRenee]

Sooooo, I've got a question for folks, although I've having trouble deciding exactly how I want to word it, I think the gist should come across. Anyhow, plz bear with me if I do ramble a bit! (:

This is largely for the single cxr, or the married dresser who was open about dressing with his SO prior to getting married...

I am at a point in my life where I have decided that I don't think I really want to keep my crossdressing bottled up, at least in terms of potentially forming romantic relationships. I'm not really keen on sharing this with family and friends, but it's obvious that withholding it from a partner is a recipe for disaster. And after coming to this board, story after story that I read reinforces that notion.

I suppose what I want to know is how do you single girls approach dating? How do you integrate it into your presentation of yourself with someone, so that it's not as if it's every thing about you, yet avoid it getting shoved on the back burner until it's too late? Can it be brought up as casually as "well, Philomine, I enjoy fly-fishing, wearing thigh highs, and potato chips. What are some of your hobbies?"

I'd also like to hear success stories that might be out there - I know there must be some.

I've back-searched some other threads in this vein, and gotten the impression that a lot of you single girls are just as happy as can be staying mostly single. Any words on the topic you have would also be greatly appreciated - since it seems that might be largely the flavor of my life for a while.

For that matter, I'd be happy to hear from GG's on the topic.

Finally, any other advice, humorous anecdotes, etc, etc?

I suppose I might just be looking for reassurance that it's all still possible, that I'm not just resigning myself to a life of romantic destitution. It's a daunting prospect, knowing that you're going to basically eliminate another 99.5% of the already slim dating pool, for reasons entirely unfair & silly - but nonetheless formidable and real.

Ok, enough from me - I'll turn the mic over to y'all. Thanks in advance for sharing!

(:

[Alice Torn]

Good question. At 57, still single, poor, and part time cd, I am not even looking for a date or ladyfriend now. At one time, i was desperate. I suppose telling them, after you get to know each other for a while, and like each other. But, it could be a deal buster, with anyone.

[AllieSF]

Well, I clearly understood your non-rambled post. I am divorced looking for woman partner. I was looking before I started dressing and have had several good relationships, but have had no real good fortune in finding someone since starting dressing almost 5 years ago. My advantage over most CD's is that I go out a lot, am extroverted and have no fear to walk up to that single woman to start a conversation when dressed en femme. I am also a member of several dating sites in male mode which get me occasional contacts, but no luck there either. So, I like many here am still single and looking.

I am hoping that just by being out dressed I will eventually meet a woman in whom I will be interested and she will be interested in me. I did meet one when I was en femme, but on our first kinda date I did the give TMI too soon and I know that I lost the opportunity at that moment. We have this tendency, at least I do, that when talking about this side of me, I feel compelled to give too much information too soon. Hopefully, I learned a lesson and will let the details come out over time as she comes to terms with me as a person and as a crossdresser. I always worry about how to tell a woman if she has no idea that I CD. That scares me a bit. I just need to test the waters and see what happens.

[Genifer Teal]

For me I decided there is no good (or easy) way to tell. Trying to describe or characterize myself is like comparing the description of a painting to actually seeing the painting. Everyone who meets me, likes my energy. People usually like hanging out with me. I do not know how to put who I am into enough words to get that across. All I would end up doing is feeding someone's own mistaken impression of who we are. I don't want that and I don't know how to avoid it. So for me, I find it best to make friends in person so they know all about me from the start. That way they can decide to like me (or not) and we can take it from there. I did explain this to a few people 15 years ago and it went well. Haven't had to do so since then - and I have made a fair share of friends.

[Jenniferathome]

As Sienfeld recapped to George, "We'll, I'm looking at an implied date on Friday and a semi-daily phone call. You have a girlfriend.". In other words, when it's trending toward serious, and we all know when that happens, tell her. The cross dressing you is not the only part of you. An intro on day one could be overwhelming. Good luck.

[stacycoral]

Kali, as a married CD for over 21 years, i told my future SO shortly before i asked the big question to her, so while i was dating,i did not bring it up, before her i did tell a girl or two that i was dating at the time, and they did not have any trouble with it, being a CD didn't them quit dating me quit. You will know when the time is right to tell her or not. good luck, enjoy being a girl it is so mcuh fun

[girlygirly]

I don't go way out of my way looking for women, but I do meet friendly ones and go out on dates. I tend to make more effort to get to know the ladies who are friendly to me when I feel like I am obviously dressed in womens clothing. I figure they might already have it partially figured out. So far, none have even asked me about it. I've even put panties back on after having sex, with no questions, she didn't say a word. Unfortunately, she was in town visiting friends for a month, and we haven't had a chance to reconnect since she left to go home. I just act normal, I never wear dresses outside the house or put on make up and try to pass, but I also don't own any guy clothing. I'm not looking to tell any of them I'm a crossdresser, but if any girl I'm dating ever finds out, I'm not going to lie. I'm not sure what else to say, I figure that if I'm always wearing girly undies and girl clothes, it isn't like I'm trying to hide anything.

[Mikaela]

I just celebrated my 6 month 'anniversary' with my girlfriend. I was not looking for anyone when it happened and that seems to be the best way.
She's a makeup artist and I met her en femme at a club, so there were no awkward coming-out conversations. Just the opposite, she had to get to know my boy side separately.

In the past, including my marriage, it never came out or came up. When married, I just didn't CD.

[Dana7]

I'm not single, but I can share my experiences.

Sharing intimate information about yourself, whatever it is, should be done gradually in any relationship. Whether it is about your personal finances, your faults and defects, or about your underwear preferences, you only share according to the depth of the level of trust that has already been built. Even with those lucky guys who find women who can accept CDing, it is still a good idea to be gradual about making revelations.

When I got together with my current SO, I didn't mention it at all for the first couple of months dating. And then when I knew we were getting serious, I tried to figure out a way to let her know about it gradually. I wanted to know where she stood, how she felt. I dropped a hint here, made a comment there. All the while, I was testing to see whether she reacted negatively.

Statistically speaking, from what I have read, about a third of women are strongly repulsed by CDing. That means if you get into a permanent relationship with someone in that category, you can look forward to hiding it forever or giving it up--or risk losing the relationship. Another third are fairly accepting of CDing. A small percentage are even supportive. And about a third are just generally ambivalent but not strongly opposed or supportive. Your task is trying to figure out which category she falls into before getting your heart involved in the relationship. And that is definitely a challenge. But if you don't do that in the beginning, you will be caught in a relationship where you have to hide something, and that is always a losing proposition, as many here have written.

I believe that being gradual in letting her know about the CDing is the best policy. I've read many horror stories about where a GG received a sudden shock and then retreated or abandoned the relationship. Not a good idea.

In my own experience, I was very incremental in my revelations, but I had let my SO know about it fully before three months had passed. I showed her pictures, etc., The full Monty. I was quite relieved that she wasn't strongly opposed to at least certain elements of it, and overall, she was willing to look at me as a complete person with different facets and interests. In the end, she didn't accept the full deal, but she completely accepted panties. Don't ask me why it worked out that way, it just did. And so I keep it low key when around her and it seems to work for both of us.

So I guess what I am saying here is to be gradual, but try to find out early where she stands. That way you can save yourselves heartache and pain later on.

[BRANDYJ]

I happen to be a man that can't even think about being single. I need to have a woman in my life in order to be happy. To live alone and not have that one special partner to me, is living a lonely no purpose existence. I know there are those that like being single. I don't get it and never will. I've told 2 past wives and my present SO. None of them had any issues with it. Well one did, but for a very short period of time. She died after 10 good years together. My response may not be a popular one for those that are that deep in the pink fog, but it really is a matter of what kind of a man you are. After all, that's what she is attracted to to begin with. To many make the CD issue way to big in the beginning. Sure way to push her away. But it should be told before the relationship moves into marriage or other long term partnership. Be all the man she wants and needs and she just might be able to handle the crossdressing on some level. But before you start getting serious, you need to feel her out about sexual and gender things in general. Is she non-judge mental, open minded and not bogged down with religious convictions that prevent her from accepting. I have always had some idea of how any woman I've told would take it long before I ever told them. I can honestly say, not one thought less of me. But they knew me, the man, long before they ever knew I had this other side. Choose wisely who you date. Get an idea how they feel about those that might be gay, bi or otherwise "different". Women in general are much more accepting and non-judge mental then men. If she is attracted to you, the man and the chemistry is there between you, she may very well accept it even if she does not want to see it or participate. My being a CD never stopped me from finding long term relationships. But like I said, I can't live without a love interest. The CDing would go first if I had to. Well, at least try.

[Veronica Lodge]

I don't think being a crossdresser requires them telling every detail of their crossdressing life to any prospective dating options. Dating someone is not the same as entering a longterm relationship. Dating is just social activities during a period of courtship.

If you aren't keen on sharing it with friends & family than you probably aren't really keen on sharing it with just anyone. Be sure of whether you actually want to bring it up with someone you're only starting to develop a relationship with...or else you may wake up and find that all those friends & family do know about it.

You can be sure that any person you start dating has their own peccadilloes, baggage, kinks & hobbies that they aren't volunteering right up front.

Just remember that your crossdressing shouldn't be a burden in your life. But you have to be realistic that making it open with a dating partner carries a chance of ending it on the spot. Just like a hundred other factors could if revealed. ie. police record, std's, a boatload of children from a previous relationship. Crossdressing, in my experience, is not the deal breaker that a lot of other things are.

I also personally avoid dating when the fog is rolling in. You end up making some very dubious decisions because of it.

[Babeba]

I think that the casual approach as you get to know a person would work quite well, if you are a person who is quite secure in your gender and your dressing is at a stable level. The flyfishing analogy is a good one! It's a pretty garden variety sort of hobby that some people just aren't going to like/be offended by - if they are very against any level of meat eating for example, or causing pain to other organisms for sport. Likewise, some women just aren't going to be able to wrap their heads around the dressing, if their upbringing/beliefs are incredibly stringent and black and white about male/female roles... they really aren't ideal SOs for you anyway, so it's good to figure that out earlier, right?

For my SO, he told me when he decided we had a chance of really getting quite serious (quite quickly - we'd known each other for about four months before dating, he told me after about a week). It worked pretty much perfectly for us, and we had a lot of very serious discussions very early on in our relationship that built a lot of closeness and trust between us. It didn't stop us from being all googly eyed and walking down the street holding hands, or anything!

As a rule of thumb, I would say that it's a talk that should be had before sex. Most women want to feel intimate mentally when they're intimate physically.

[DebbieL]

One of the wonderful things about online dating is that you have numbers working in your favor. This means that you can be incredibly honest, and have a really good response level, and with a number of movies that depict Cross-dressers in a better light (even though they are mostly about drag queens rather than cross-dressers and transgenders). In addition, more corporations are aggressively promoting "diversity programs" that address transgendered an a manner similar to women. Dealing with the issues of sexual harassment of both transgendered and women.

In my profile, I said I was a cross between Robin Williams, Jim Carey, Bill Gates, Shaun Connery, and Madonna. I was as nutty as Robin Williams, I was crazy like Jim Carey (in a fun way), I was as nerdy as Bill Gates, an old Geezer like Shaun Connery, and love to dress like Madonna. I included some picture of me in office attire, in some nutty poses, and several in my prettiest mode. I was not that surprised that hundreds of women looked at my profile and moved on, but there were several who stopped, expressed interest, and wanted to know more. Some moved on, but I ended up going on dates with 6 women. One was only submissive and wanted the dominatrix exclusively (I like to switch), another was dominant and masculine, but very interested and interesting. Another was very attractive and very interested, and had a son with autism, but realized that I might not quite be ready to commit to her son. Another was very nice and a bit of a tom-boy, but very much liked Debbie, however, she wanted to continue to live with and take care of her aging mother, while I was ready to settle down.

Lee sent a not saying "Honey, you're wearing a dress, what's that about". I told her that I was transgendered, had been since I was about 4, and that I had kept that secret from my first wife until after we had moved in together, but before we got married, and it didn't work out in the long run, so this time I wanted to be as honest as I could as early on as possible. We talked on the phone for about 2 weeks because I was working out of town. When we got together she was VERY interested in meeting Debbie, and once she did, she was VERY pleased.

When she lost her key to the room, while we were on a trip, and I cheerfully got some flashlights and helped her look for it, then offered to book another hotel, take her to my house and bring her back in the morning, or we could sleep in the car, she decided I was a keeper. When I decided she was a keeper, I invited her to an introduction to the Landmark Forum, and when the leader asked people to put something at stake, I asked her "Have you thought about getting married?". She registered for the Forum and I got her a "place-holder" - a CZ about 1 carat in size. She thought the stone was too big, so when I bought her the diamond ring, I bought one 1.75 carats. I also gave her Jewelry for Christmas when her parents and friends were watching, and went shopping together with her, and actively helped her pick things out, find different sizes in her styles, and learned her styles.

We got married in 2006 and the only time she ever gets concerned about Debbie is when I start contemplating transition. She also doesn't want me bringing Debbie to Church, so I can wear studs and 2 inch chunk heels, but not dangles, leggings, or 3 inch heels. She's been going to that church for 25 years, and didn't want to upset people who have been her closest friends for most of that 25 years.

Ironically, one of the things that pushed her forward on the first day she saw my profile, was when she showed the picture to her daughter (now our daughter), who thought it was great and that it would be nice that I didn't have to prove my masculinity or be all macho. Lee met her first husband in the army, he had a nasty and sometimes violent temper, and they often had nasty fights. He wasn't her daughter's father (for decades merely the "sperm donor").

The marriage has been amazing and wonderful. She loves that she doesn't have to be girlie all the time, and loves it when Debbie comes out, especially when Debbie starts going on a cleaning spree or does all the laundry. She also like going out to dinner with Debbie. She even gives fashion advice which has made it much easier for me to go for hours without getting read, because I'm not attracting too much attention. When I want to "**** up" for a party or a dance, I get read more, but Lee has fun with me on those occaisions. When Rex hit 315 lbs, Lee helped Debbie get on Weight Watchers, and encouraged Debbie to shop for girl's pants that were a size or two too small, providing an incentive to lose weight. Now, I've lost 80 lbs, she's lost 50, and I'm wearing 4-6 sizes smaller than she wears.

The one thing I would strongly recommend is to be really open minded about possible partners. If you have a woman who isn't exactly a fashion model, but can totally love both your male and female side, and can freely and happily express both her masculine and feminine side, you would both be far happier that you could imagine. Would you rather have a size 5 who is constantly trying to destroy your feminine side and blackmail your masculine side, and wants all your money but doesn't want sex with you, or would you rather have a size 14 who loves both your masculine and feminine side, honors both, and loves all kinds of wonderful sexual activities, and helps you build real wealth?

[DebbieL]

Let me bottom line this as best as I can. As a cross-dresser, you are highly desirable to certain people, especially bisexuals. If you told 10 people, not necessarily people you want to seduce or have sex with, but people you are willing to trust to "fix you up" or to share your situation with others who can fix you up, you could be less than 3 degrees of separation from someone who would introduce you to a woman who would fall in love with you BECAUSE you are a cross-dresser, because you are a little "kinky" and because you might be willing to share or relinquish some control in exchange for acceptance of your femininity.

Imagine getting into a relationship with a woman who actually WANTS to feminize you as much as possible, and wants you to be as beautiful as you can be. At the same time, if you don't want to transition, she can enjoy whatever masculine aspects you want to express, when you want to express them.

While you are single is also a really good time to decide where you REALLY want to go.
Imagine no constraints, no limitations, and unlimited resources.
Would you want to transition and become a woman full time?
Would you want to dress up every day? Or just once or twice a week?
Would you want to take permanent measures such as electrolysis, laser hair removal, or hormones?
Would you want to have real breasts you could hide, or real breasts you COULDN'T hide?
If you could trade a penis and male orgasm for a clitoris and multiple orgasms, would you make the trade?

If your wife or female lover wanted you to transition, would you want their help in making that transition?

Next, consider the possibility that ANYTHING could happen in 5 years, if you got into communication with the right people.

You could have a lover who wants to help you do everything you wanted to do in that ideal situation.
You could have a lover who could provide support and encouragement, as well as financial and/or medical help in the transition.
You could have a lover who wants you just as you are, and just as you aren't and also wants you to have what you really want and will love you all the way.

There is a catch: You have to be honest with yourself, your friends, your family, and the people in your life.
You also have to be willing to "suit up and show up" at social events, parties, fund raisers, and other social functions where you can meet people who can see you as a beautiful woman.

Don't dream it, BE IT!

[KellyJameson]

I have noticed that the attitudes and openness to alternative lifestyles varies depending on geographical location. Atlanta, Seattle, Los Angeles, Boston I have found to be very open and I'm sure there are other cities as well and this seems to help in meeting women who are open to crossdressing because they already have seen many of the different facets of human behavior.

In Seattle people like to ride their bikes naked and the way some of these guys look naked on a bike I'm sure makes crossdressing much more appealing to the general public.

Many of my interests and hobbies bring me into close contact with women, cooking classes at the local Sur la Table, evening college courses, volunteer work building sets at the local theater, ect..
so they see me in my element and once they seem confident that I'm not a axe murderer or sexual predator I slowly let them learn about my quirky ways (and there are many). This helps me learn about there lives, tastes,circumstances,attitudes,wants, ect...while learning about me and it is not long before I tell them "I crossdress" and "no I'm not gay" because that is when it gets to be really interesting. Of course I do not tell them I'm a woman trapped in a mans body there is only so much information a person can digest in one sitting.

Even in drab I dress very androgynous with no hair on my arms or face and clear nail polish with hair to the middle of my back so my appearance attracts a certain kind of women and this filters out those who want a very masculine looking man and all that is assumed to go with that look.

So in short if you have the freedom to live your life as close to the natural expression it takes on when you can be completely free to be yourself than immerse yourself into the sea of humanity for the shear pleasure of experiencing people in all their splendor you will automatically attract your complement if your approach women not like you are going to the store to buy something off the shelf but as a feeling, thinking, unique human being who brings value into your life from the expression of her life force and not only for all that superficial stuff.

All the other posts are excellant but one stands out in my mind and that is DebbieL. This comes from hard won courage, passion for life and total acceptance of self. All necessary ingredients if you are going to get the most from life. She would make an excellant mentor if you can convince her.

[Ellyn]

I think your chance of starting a relationship after confessing to a your date that you are a crossdresser are just about nothing. Maybe some of the gender girls can chime in and give their opinion, but I am betting that a very high percentage of them will also tell you they would do only one thing upon learning that their new date was a crossdresser--run. From what I gather from reading views on this site, and on others is that most women when faced with such a senario express an opinion of crossdressers varying from "somewhat odd", through "too creepy" or, "too wierd",to "some sort of pervert", or "obviously a homosexual". That pretty well eliminates most women who are seeking a partner who might end up fathering her children. And who knows what thoughts that would bring. If you are looking for a mate, not just a date, you have a far better chance by keeping your cd'ing in the closet. Then "if" in time a relationship develops, then deal with it. You will have far better odds at that time.

[sissystephanie]

I have been a crossdresser since age 6 and I am now 79! There was some time off from CD'ing when I was in the military and also when I stopped for 5 years after our children were born. I started again because my wife begged me to. She knew that I was a CD when we married, because I told her when I proposed to her! I have always believed in honesty, so I followed that precept. She accepted me "as is", and we had almost 50 years together before cancer took her!!

If your girl runs when you tell her, she isn't for you anyway!! If there is really true love between you, crossdressing is not going to change things!! Unless you want to actually be a woman! If that is the case then you are talking a whole different story! And there are other women out there who do not mind crossdressing!!

[NicoleScott]

I enjoy fly-fishing, wearing thigh highs, and potato chips.

Maybe when you have this talk, just add: "but not necessarily in that order".

[GeminaRenee]

First, I wanted to say thank you to all who have taken the time to respond so far - your words have been helpful and encouraging, and I appreciate that.

It seems that some of you have been successful in dating, and sometimes in translating that into successful relationships, and that's reassuring for me to hear. I think the key might be to not view it as 'limiting the dating pool,' or whatever - but instead to think of it in terms of making it much more clear-cut who is or is not right as a potential partner.

I do know that there are women out there; one thing that I did not yet share about myself is that I once had a SO that was not only supportive, but also participatory. There was no science behind the way she found out - on a whim during an emotional discussion, I revealed it. There was a short period of mild distress while she came to grips with the idea, but overall it was relatively painless. At first, we got dolled up together and went out a few times, but like the water flowing out of a dam, the urge behind the act dwindled, and it became much more subtle - going out to the bar wearing guy clothes, except for girly jeans, or accessories, maybe a little eyeshadow, etc. Because we were living in a small town and my work pool overlapped significantly with my social pool, some issues arose, and I withdrew from the activity entirely. Unfortunately, life called, we grew apart, things happened, and our relationship was no longer reconcilable. For a long time, I viewed it just as some amazing anomaly of time and space and person that would never occur again. That could still be true, I suppose. But hearing from all of you has made me hopeful.

Thanks again, and anything anyone else has to add is appreciated!

(:

[sometimes_miss]

Regarding the 'Be Gradual' concept. One of the bad things about that, is that for a whole lot of women, crossdressing is a deal breaker, and it's not going to matter how slow you go about it. And, by that time, both you and she will have much more emotional feelings involved, so it's only going to hurt that much more when a split up happens.
If you have the courage, the best way I can think of would be to go out with some gay female to her clubs, and if asked, then explain why you're there. Gay people I've known for the most part have been if not completely understanding (most of them think we're also gay but just in denial), at least accepting of us. I've also known more than a few straight women over the years that went out for a drink after work with their gay friends, so perhaps that's another idea.

[docrobbysherry]

Since you're a "second time around" guy, you've had more experience at "dating" and with a serious relationship than unmarrieds.

If you become serious about someone, it may depend if she's an "unmarried", or, "second time around", girl on when or if u should tell her! I think it will have to be your call!

Just realize there's a good chance she'll never think about u the same way again after u tell her!

[Rogina B]

I think you need to edge a little closer to the "dark side" when you are searching for an accepting SO.At the very least,think about how and where you will find a "dating pool" of possibly open minded women in your area. I think T's loose way too much momentum trying to get a keeper out of the "vanilla" dating pool. Just my opinion.