Looking for some advice

[stephaniestilley]

As I've been exploring the world of cross dressing more, I've been finding myself becoming really open to the idea of being in a relationship with a man. I just think I'd feel much more comfortable in the feminine side of the relationship and I've started going on dates in drag. I've only come out of the closet fairly recently and I'm curious if anyone on here has any advice, this is all just such a new experience for me

[Tracy Irving]

Make sure he knows you are a dude in advance of the date.

[Jaylyn]

I'm sure there will be plenty of advice on here, many on here and I know somebody will help you. All I can say is just be yourself and enjoy what your doing.

[Beverley Sims]

Establish your boundaries and agree to them before you start.

The obvious one is to establish your true identity.

Do not try to pass as female if you are not gay establish your sexuality beforehand.

If you both agree on things you should have a good time.

Remember the relationship can escalate fairly quickly and become soured easily.

[Micki_Finn]

All I can say is that It seems to be not uncommon for CDs to experience bi/gay-curious feelings. Just remember fantasies are very different creatures from actual sex, which is a whole other thing than actually being in a relationship with the same gender. I’d recommend exploring your sexuality apart from the dressing before you just dive right in.

[emma30]

Good advice Micki

[Sherrii]

What Tracy said for sure or it could turn out very bad for you! Sherrii

[Krisi]

OK, if you are a man and want to have sex with another man, that makes you gay or at least bi-sexual. Not that there's anything wrong with being gay or bi-sexual, but strapping on a pair of boobs doesn't change anything. You are still a man.

As others have said, it's critical that your "date" knows that you are a man. It's also critical that he knows beforehand if sex is an option or not. When a man takes a woman on a date and spends money on her, the desire is sex. Maybe not on the first date but that' the end expectation in most cases. It's the same for a man dating another man. If you're not willing to provide some sort of sex for your date, you need to make this clear up font and should probably pay your own way.

[laura.lapinski]

Hi Steph, and welcome,

Good advice by all. Be careful, have fun. I'm sure you will become familiar with yourself more and live more relaxed as you self-actualize.

[sometimes_miss]

It depends upon what your goal is. If you're dreaming of the typical girl's life, with a lovely wedding, being a home maker, raising children, etc.? Probably not going to happen. If all you want is sex, then you might be able to get what you want. Men don't specialize in long term relationships.

[Stephanie Julianna]

For some of us, dating men is an eventual outcome. I used to frequent crossdresser bars in NYC around 1980 which had many crossdresser admirers. But it was Lee Brewster who played matchmaker with me and my eventual boyfriend, Sam. He started a relationship that lasted over 25 years. I will be honest and tell you that for me there was nothing like being the female half of a couple. I dressed as much for him as I did for myself. Like any young woman, I wanted him to be proud to be seen with me and that was all the incentive I needed to try and achieve a look that would allow him to take me anywhere he wanted without worry of my being read. It was a wonderful time to be a woman for me. Sam was the best boyfriend a girl could ever have. The only way you are going to know if that kind of relationship is what you need is to go for it. I just can't tell you how to meet people like that today.

[Tracii G]

I am not going to give advice but I will say wear a condom please.
Remember if you are just recently exploring there is a lot you don't know and what you think sounds like fun could very well turn out badly for you.
There are trans girls getting murdered everyday. We don't want you to be a statistic.

[Ronnie38]

As a bisexual male, i would like to offer my two cents. It sounds to me like you could quite possibly be gay or bisexual and there is absolutly nothing wrong with that. Explore it, and try new things. If dating a guy while in femme mode, just like with a girl, be open and honest. Be sure he knows you are a guy and that he is comfortable with that. Most guys, gay or not, want sex. Its hatdwired into us. Set boundarys. If you think you want to try something, play with toys first and see if youre comfortable with it. There are some guys out there who, when they get started, dont like to stop. Some manipulate, some use force. Set boundaries. If he cant respect those boundaries, get out quick. Most men ive dated are selfish. There are some very sweet guys out there as well. Dont settle. Also, its been said already, practice safe sex. Some diseases can be transfered orally as well. Explore, enjoy life and what it has to offer. Have respect for yourself and expect the same from any partner you may chose. I hope this is actually helpful. If not, dont hesitate to say so.

[docrobbysherry]

Meet strangers in public places the 1st time. Let someone know where u r going if u meet someone in private until u get to know and trust them! Break a leg!:)

[CONSUELO]

You might be interested in reading ALICE IN GENDERLAND by RICHARD PRINCE.

I suggest it because he talks a lot about why he wants to be dressed as a woman and be with his long-time boyfriend. It might help your thought process

My only concern would be one that has been expressed already; be safe and choose your dates with care and a lot of background checking.

[stephaniestilley]

Thanks everyone for the thoughtful replies, it's certainly given me a lot to think about! So far I've gone on two dates with someone that I've met recently and they've gone pretty well, nothing physical has happened yet but he's been really accepting and he's a super nice person. This may or may not end up being a relationship but either way I've at least made a new friend :)

[SHINY-J]

Be honest and up front about who you are and then just be safe and enjoy yourself. And don’t feel compelled to group yourself into a specific category.

In my “regular” life, I’m a straight hetero male. I have relationships and date only women. It’s all I honestly want. I would have no problem with admitting I was gay or bi if I was, but I truly only think of women when it comes to what I’m looking for in dating, relationships, or marriage.

However, when I dress, that does change. While I’m still attracted to women, I often imagine being with other CD’s and even men. However, it’s only when I dress. And in my particular dressing situation/circumstances, it’s really more of a desire to be dressed in front of someone else and being submissive. I won’t go into any more detail than that in order to comply with the rules of the forum. But, those same fantasies do not involve, going on dates with men, holding hands with men, being married or being in serious relationships with men, going to the movies with men, etc... it’s strictly sexual.

I’m sure some consider that bi or even gay and that’s fine. Categorize me however you like, but back to the subject.. you stated you only recently began dressing and as it’s normally a pretty new, emotional, and sometimes confusing time in your life, make sure to give yourself time to explore and find out what you truly love and enjoy and what you don’t.

But have fun, be safe, and be honest with others and yourself. I applaud you for having the courage to go out in public and live in this world openly as The individual you want to be. I wish I had that kind of courage!