Chance to come out... Should I take it?

I would suggest that you take it very slow and carefully. Until you have the actual "Discussion", you will need to tread lightly. I had been underdressing in panties and bra for a while and was on the "men Wear Bras" website when I was clled away to the phone and my wife saw that site and my posts on it and really blew up. She was concerned that I was gay or wanted a sex change or whatever and, after I had overcome those fears (2 mos), she finally consented to my wearing panties. Later, after the world failed to collapse, i broached the idea of my wearing a bra and she finally consented. It took a long time (2 years), but she finally caught me wanking and insisted we buy a CB6000. That journey took a while but now we are finally in synch and enjoying my chastity!

 

I agree, taking it to fast will easily do more damage to your relationship than good.
Why not suggest it once and see what she says. There are plenty more Halloween party’s to come but maybe this girlfriend is here to stay.
I once told a former girlfriend of my high heel fetish, and I was all exited about telling it to her. At the moment she took it all in and didn’t seem to upset, but a few day’s later she broke up with me because of the shoes. It was WAY too much too fast for her.

This thing in your mind that you want to wear a dress is evolving in your head for 27/7 for a long time now, you can’t expect anyone else to make that step instantly.

If you want to keep this girl I suggest taking it very slow.

 

Humm well may be try to facilitate that event throw your own party or find another. It is quiet a good way to bring things out in the open.

Xx Wendy

 

that a shame cos haliween partys am lots of fun.

 

I'm going to throw this out there for you also.. Sometimes ppl really deep down inside are turned on by some things that they pretend to not like in everyday life. Example, my wife always talked bad everytime she saw trans or bi or gay guys anywhere but once we got deeper and deeper into making our darkest fantasties into reality, here I sit in panties that she bought me with painted nails she did for me and only wants me to be feminine.

 

Lol

I use to have a boss long time ago who was rather homophobic.
However use to employ some very good looking guys. Soon as the sun was out and the guys had their tops off washing trucks and kit he was not far behind down from the ivory tower.

Xx Wendy

 

Things are looking good for you.
About the piercings I have a frenum and a nipple piercing. I would start with the frenum. It's much less painful. I don't know about a prince Albert, still thinking about that.
Maybe you can ask her if she wants to put het finger up you ass when she is blowing or jerking you. Then go out and let her buy you a butt plug.

 

Hello OBL.
Boy, you certainly have a sensitive issue on your hands. My reply may be long, so my apologies ahead...not trying to hijack this thread! I say DO NOT use Halloween or anything of the sort to convey or disclose what is rolling around in your head. I made a VERY similar mistake many moons ago on the 2nd Halloween with my Wife/Mistress/Keyholder. She had unlocked a door in my psyche which had exposed my, for the most part latent, fetishes relating to crossdressing, lingerie etc and submitting to dominant female figures. By our first Halloween on her own volition she had stocked half a dresser she had set aside for me at her apartment and had filled several drawers in it with various types of lingerie and lacy undergarments,, stockings, body stockings, pantyhose, several boy cut leotards a long sleeve black minidress and had even purchased a pair of very high strappy, spiked heels to fit me. Our first year, she took me to 2 Halloween Fetish Masquerade balls as my scantily clad dominatrix and me in a black unitard, hose, chunky shoes, a small plug held in by a tight thong and various levels of costume bondage gear including a dog leash and collar. No masks, wigs or makeup to hide my identity...very unnerving. We went with another couple (a GF of hers and the BF) each time and to the seeming delight of my Wife/Mistress/Keyholder my attire was always a big hit with them, but rather
embarrassing to me especially in front of another guy dressed more manly and Gothic. We went to several other "off season" fetish masquerades between our
first and second Halloween with me dressed the same but having discussed the idea of me wearing my heels though I never did. I was beginning to feel less weird and more comfortable to experiment as our second Halloween approached. Now, add in the fact that she had a large collection of still photography lesbian erotica to go with her vibrator (though denying bi-sexual leanings when I would joke with her) I had been making the assumption I was fulfilling a proclivity of hers by the fact that I got the hottest sex and most passionate reactions from her when I was in women's clothing (no make up or wigs). I took it upon myself to dress for her and put on foundation, eyeliner and lipstick and videotape myself playing with a large dildo I would use on myself when we would masturbate together. I told her I rented an adult flick one night for us and she watched intently seemed to enjoy it by her reaction and energy afterward then proceeded to tell me she did not want me to "be a woman'" and that she "could do without the makeup"....ummmmm, OK, this the same woman who regaled me with how she made a guy up when she was in her late teens and could not believe the hot make out session afterward. Fast forward to that October and I was all over the idea of changing up my costume to that of a French Maid. She was excited by the idea until I strongly suggested a wig and makeup, shaving my legs (she already had me shaving my torso to mid thigh!) and Mardi Gras masks for both of us to be more "incognito" (and perhaps a wig for her too). Mind you, 25% of the time I spent at her apartment I was dressed to some degree cooking, eating, sleeping & "getting busy" MANY times at her behest. Well, KABOOM!!! It ALL blew apart. The comfort, the playfulness, the trust...all gone. Granted, I did want to see how sexy I would look AND I was looking forward to the rush of being out fully en femme WITH her...thought dinner together like 2 girlfriends at the nearby diner would've been hot...she completely flipped, I felt embarrassed and ashamed. I purged most of the clothing, toys etc.. We went through a total sexual "reset" , back to vanilla. So boring! How does one go back??!! That was a long time ago and it has taken us this long to get comfortable...I am always worried that the same thing will happen. We HAVE had several setbacks in the realm we are inhabiting now. I tend to communicate and want to talk and she wants me to "read her signs'. She tells me to stop worrying and not to ask so many questions. I just dont want to feel that same hurt and shame again. I dont fully "get" her but I make sure she knows I accept her identity and proclivities even if
they are veiled and unclear...maybe she suffered a similar embarrassing situation somewhere and does not want a repeat? I will more than likely NEVER know. I just keep hoping we keep status quo and stay fresh and move forward...so my advice again, don't do it. Go SLOWLY and let the woman who holds your key be the guide and ASK PERMISSION GENTLY. It is not worth upsetting a good thing. Rome was not built in a day. Hopefully you have a long future together to grow slowly and comfortably...TRUST ME...I have many ideas and would try to pass as the female of HER choice this Halloween or for some fun masquerade event if she would let me...but the big picture is how much fun we have together alone...the love and passion are deep and I want nothing to derail that. Best of luck to you and....HAPPY HALLOWEEN!

allaboutHer

PS...I hope the detail of my post paints the picture for you of where I was at and that it helps...it was not meant as a self indulgent "bragfest". ☺

 

It's the big difference between tv/cd ie dressing for pleasure and ts who dresses because it feels comfortable and natural with no sexual feelings as such .

The problem is trying to get partners to understand it's much deeper than the frocks and heels.

Most partners when the find out jump to the conclusion that its all gay sex and drag queens. Which ironically is the exact opposite, as most gay guys have no interest in the female form let alone guys in frocks.
Thus for some a fancy dress party or in this case Halloween can be a chance to bring things out in the open .

However for everyone it's such a difficult judgment call ,as to what to do.
I am glad to say as being TS is becoming much more main stream it's getting better as more people understand what a ts goes through and the unhappiness they can suffer.

Xx Wendy