Crossdressing thoughts and opinions!?

Question

I have been a crossdresser for many years, however I only dress and go out every few months on average. I am very passable as a female with my appearance...now speech is another topic...lol. I have done this for roleplay and excitement only, never to disrespect another female. I am not gay or bi-sexual and the places that I have attended are generally accepting of all alternative lifestyle people. This is to stay out of trouble. My question is: when is the right time to tell a woman you dating? You just don't walk up to someone in a club and say hi my name is "such" and I am a crossdresser. You need time but what is that time? Also, what are your true thoughts on crossdressing males?

Answer 1

I told my girlfriend at the time, now my wife, very early in our relationship that I was a crossdresser. You need your getting to know one another period, but the best time to say something is early in your relationship. I have heard so many stories of men hiding if from wives for many years, and tha is no way to live. When I told my wife we had only been dating a couple months, but I knew that she was the one I was going to marry, so I wanted to be up front with her. I am lucky she is accepting of me and I still get to do it. We have been together for just over 6 years now. So good luck to you, you will find someone.

Answer 2

It all depends on the woman. I've been married for 22 years and I know that my wife has negative feelings toward crossdressing men, so I have never told her. Now, I personally am quite happy. I'm fortunate that my work allows me to travel often enough to fullfull my crossdressing desires. The last thing I would want is to have a woman who is not excited by my dressing "tollerating it". I think that would be kind of selfish on my part, and since most woman are not turned on by it, I am very content to have a wonderful loving wife who fulfills all my desires (and they are many) except one.

On the other hand, if she seems positive about other crossdressers (maybe take her to a show to gage her opinion), then I agree with most, if you're going to tell her, tell her early, as it won't get easier with time.

Answer 3

I dont have that answer for you because I dont think most heterosexual women find a man who cross dresses that attractive or sexual.
I understand that you need this in order to satisfy some deep seated desire inside of yourself but to find a healthy hetero female turned on by being with a man that looks like a woman is what I would say a tough fit.
I feel for you man but dont know what to say but good luck!
I think you would have to win them over first with your manleness however telling them after the fact would surley set you up for failure.
Then again if you tell a woman up front she will probably pass you by.

Answer 4

i'd imagine when you're brazenly admitting some thing like this, you've already done dissimilar self-discovery and understand who you're. If this can be a center area of your self, and also you understand that you're not any further going to experience free in a relationship with a lady that can not settle for this, then you quite ought to tell her sufficiently early on in the relationship. that is not any longer honest to both of you to pop this out previous due into the relationship after anybody has invested dissimilar thoughts. some women folk can settle for this. some gained't. no longer on the first date, honestly. i'd imagine on the point on your relationship once you experience smooth and an believe her, which will be an proper time. If both of you met in an option venue, then per chance you are able to tell her a touch in the previous on. i do not fairly understand. i have not in any respect been in that difficulty. i'm basically writing how i trust. So take that with a grain of salt. As for my suggestions on it, i do not fairly understand. not in any respect had to confront that area of myself. the in trouble-free terms aspect that i can say is that an effective guy is fairly troublesome to discover. i understand that. If it is his carry-up and that i love each and everything else about him, then so be it. i can likely come across approaches to stay with it. solid success.

Answer 5

I have been with a guy that likes people to cross dress and have tried it. It is something that i'll probably never do again. But I think you have a finer appreciation for the opposite sex. but you identify with the gay community as well which is interesting.
I think anytime is right to divulge your a cross dresser although I think you would be better off to do it sooner than later due to the fact that the female may not be into it at all and you'll find out quick. for sure.....but she may want you to do it with her.
Is the time right? mabey not .but wouldn't you like to find the single person that is interested.

Answer 6

I think you should tell the person you are dating when you are feeling really comfortable with her, but not so far along in the relationship that serious emotions have come into play. It is not fair to either of you to not tell her though.

Answer 7

I suggest you did what Moe Green did. Singing Telegram. If you are both in the living room a knock on the door, a song, and depending on her reaction you do one of the following:
She freaks out, you beat the messenger and pretend its a joke
She accepts it thinks it cool then you share hose.
She inst sure then you show her your wearing her panties.

Win WIn WIn

Answer 8

If you are in a serious relationship you should tell her but if you have only been on a date or two you dont have to.

Answer 9

it sounds like something you tell someone after you have already been with them at least a few times.

Answer 10

tell her your into those diaper wearing adult fetishes. so when you tell her the truth (for once) it wont seem as strange