New GF and my crossdressing secret!!!!!

[Tiffany29]

Hello All,
Ok so I need your advice, I am in a new relationship with a woman and she is extremely open minded, more open minded then I could ever imagine.
Anyway she knows about all my fetishes and fantasies but she doesn't know about my full crossdressing. She is very supportive of my pantyhose fetish and her fetish to see me in womans panties is stronger than mine. She wants me wearing womans panties all the time which is awesome.
I know crossdressing is an extreme and I haven't said anything to her because I want to take things slow and feel it out.
So we have been talking that she wants to roll reverse and we were watching porn the other night and I picked out a porn where roles were reveresed and the guy was wearing pantyhose and heels and we watched it and I asked for her feedback. She said it was hot but she said can I ask you something and I said of course. She said well does that mean you want to wear heels? I said well would you want me to wear them and her response was that it did nothing for her and she doesn't prefer it but if it was something I wanted to wear she would let me wear them. I told her that I never thought about wearing them before so I don't know and it was left there.

Just to give you a little back ground on my gf, like I said before she is extremely open minded and she said she would do absolutely anything to make me happy.

my thinking is to slowly build up to it. we are going to the porn store this weekend to get her something to help role reversal and start exploring with that and let her make love to me and that is her biggest fantasy is to role reverse with a guy and she already knows I want this to happen while wearing pantyhose and panties. So I was thinking of doing the pantyhose and panties first and then next time just tell her that my mind is interested in wearing heels and see what she says, She already knows our fetishes and fantasies will evolve because we talk about it all the time.
So do you all think that plan would work and slowly add pieces to the fantasy and see if I can someday get her to allow me to be fully dressed? Thoughts?

[Ariana225]

Sounds like she is really open to things. Only you can judge her personality when it comes to going slow or fast on the reveal. If you’re still fairly new to the relationship and already going this far you might as well go all the way.

What was the follow up situation with your wife? I got a refresh from your thread that you started a few months back about your wife finding your panties and pantyhose. If you split up I’m sorry for that. But it’s good that you’re starting your new relationship with little secrets. A lot of us wish we would have done that from the beginning of our relationships.

[Jaylyn]

It's not my thing but hey if it's yours then I'd say go for it. It really sounds like you are I an understanding relationship with a open minded GG. Roberta is right about being up front at the first. They say there is someone out there for every one and sounds like you've found what you may have been seeking. Enjoy and have fun.

[Dana44]

Nice girl friend Tiffany, Yeah I would keep it slow but I would ask her maybe one day you can fully dress me.

[Tamsin Secret]

There is obviously something stopping you saying what you really mean to her. Let's be honest from your description of the relationship so far it seems pretty no holds barred so what's the issue? Just ask. My intuition from the little I know is you fear rejection. Could this be from previous experience? :2c:

[NicoleScott]

You have the green light to wear heels if that's something you want to do. As for dressing fully en femme, you could ask her if there are other things that she would like you to wear, or might have no problem with you wearing if, like the heels, it's something she's not particularly into. Take advantage of conversations on such topics to introduce the idea of your full-on crossdressing.
My wife was reading a magazine article in which there was a crossdresser. When she mentioned it to me, I calmly replied "harmless fun". .....ah, the opening I needed........
She asked if I ever did it (yes), did I like it (yes) do you want to do it again (yes). I was ready to shut it down if I detected any negativity, but she said "So do it!!!". And I did.
You might never know the level of acceptance until you test it.

[Rachael Leigh]

Ok, I’m sorry why do we need to be involved here to answer this question?
I’m confused

[docrobbysherry]

I'm with Tamsin, Tiffany. I think u saying u, "Hadn't thot about heels", was a mistake. Both of u seem bent on satisfying your "fantasies" in the bedroom. That may work out well or it could just disappear if they don't work out consistently for u both.

Why r u afraid of telling her u want to dress up? What's the worst that could happen? It sounds like neither of u have much invested in your "relationship" so far. It sounds like just a sexual fling to this point. I'd suggest letting it all hang out and let the pieces fall where they may! At least, you'll both have some fun!:D

[Vickie_CDTV]

Given her personal desires and kinks, I doubt you wearing heels would be a deal breaker. She just might not have a thing for high heels (or men in high heels), even some women who like men in panties (as rare as they are) may not also be turned on by the idea of them in a bra or heels or whatnot.

[Elizabeth G]

Hi Tiffany,

You talk about parceling things out to her which I can understand. My only concern is that if she eventually realized that this was always your end goal and that you kept it from her she may interpret that as a deception, and trust, once lost, can be very hard to regain.

Elizabeth

[Rhonda Darling]

So, you have a girl friend who wants to "peg" you (Arghhh, Captain)? But, what about your wife of 10+ years memtioned in your earlier posts? Is she mysteriously gone? Is there a troll under this bridge? I'm not sure, but this story seems too over the top compared to your previous 3 posts. If I'm wrong, my bad. But I'm out of here, having no time for this salacious clap trap story that seems like bait for us.

Rhonda

[Aunt Kelly]

.
So do you all think that plan would work and slowly add pieces to the fantasy and see if I can someday get her to allow me to be fully dressed? Thoughts?

So... you mean, make her think that you kind of "grew into it", as a result of your fantasy play. Right? No. I think that's a bad idea, because it is not honest. You seem to value this relationship, so don't screw it up by introducing deliberate deception. Be open and honest about your TG nature, now. If she is as open minded and understanding as you say, you'll both find a way to make things work. Make sure to let her know that you value her understanding and appreciate her attitude for the rare thing that it is.

[Rachelakld]

I showed my girl, my full collection before we got into a serious relationship - highly recommended as it prevents a lot of issues in the future.

[DaisyLawrence]

Sorry to hear your marraige has ended recently. So pleased you've moved on to a new relationship so quickly. Did your wife leave you after she found your stash in the summer?

[Isabella Ross]

I'm with others on this thread: full disclosure! But as Rhonda points out, a couple of discrepancies in this thread...

[Tracy Irving]

I am in a new relationship with a woman and she is extremely open minded, more open minded then I could ever imagine.

She should be fine with your crossdressing if she wants both of you to enjoy your new relationship.

[Sherrii]

Just keep on the way you are. Add a little more now and then and make sure she has fun with it too. If you do things she wants, she will do things you want. Make sure you are open to her wants and have fun when she wants you to do or wear something. Just ease into more CDing. If she might be bi you could use the CDing here, "isn't this hot two women?" Good luck! Sherrii

[Tiffany29]

yeah I have a fear of being rejected and it ruining the relationship. I haven't been rejected before other than my ex wife finding my stash and instantly calling me gay without asking what or why I had them.

[mikayla1964]

As for me i believe in being honest. Sometimes it works out sometimes it doesn't. But staring of with not telling the truth can seriously hurt a relationship. But back to the heels i would offer up the thought of a skirt before i would the heels. And build from that. If she is wanting to take you then more than likely see is pretending your a woman. And dressing would go farther than the heels. But that is just my opinion sand you know what that is worth. But honestly it's something you need to decide for your self. But good luck. Let us know how it turns out.

[Tiffany29]

Sounds like she is really open to things. Only you can judge her personality when it comes to going slow or fast on the reveal. If you’re still fairly new to the relationship and already going this far you might as well go all the way.

What was the follow up situation with your wife? I got a refresh from your thread that you started a few months back about your wife finding your panties and pantyhose. If you split up I’m sorry for that. But it’s good that you’re starting your new relationship with little secrets. A lot of us wish we would have done that from the beginning of our relationships.

the wife and I are getting a divorce and its just about finalized. so onto new things

- - - Updated - - -


So, you have a girl friend who wants to "peg" you (Arghhh, Captain)? But, what about your wife of 10+ years memtioned in your earlier posts? Is she mysteriously gone? Is there a troll under this bridge? I'm not sure, but this story seems too over the top compared to your previous 3 posts. If I'm wrong, my bad. But I'm out of here, having no time for this salacious clap trap story that seems like bait for us.

Rhonda

my wife and I are in the final stages of the divorce and just figuring out the last few items that need to be divided. not sure why you think this story is over the top. I am just asking for simple advice.

- - - Updated - - -

sorry if you all think this thread has discrepancies, I am new to being open about my CDing and was just looking for advice is all from people who might have had a struggle in this as well. Didn't mean to upset people.

[Jenny22]

Tiffany, in your post you said, "but if it was something I wanted to wear she would let me wear them." SHE would LET you???? Be very careful with her taking this approach to anything you might want to do or wear. She's not your wife. We don't know how you two met and hooked up or if you are living together. She sounds like a great find, as you also said, "she is extremely open minded and she said she would do absolutely anything to make me happy."

So, tell her you like to and need to CD, NOW. If she's not accepting, its better to find out now, before the relationship deepens. Good luck, girl!

[CDPheobe]

Hello Tiffany and we come to these forums. I can relate to you because at the time when my wife was my girlfriend, she asked me if I had any fetishes. I told her straight out and she asked men to bring my panties, bodystockings, shoes, and pantyhose to the condo and i did very willingly. From there i asked if i may try wigs, makeup, dresses, the whole nine yards. My wife like yours, very open minded as well took to it. Today, i dress up fully and she lets me be myself. So in that sense you can say it worked out for me but every relationship is different. She needs to feel secure. I have told my wife many time i dont plan on being with a man or have a sex change. I have proved to her those very words to this day. Hope this helps. Add me so we can correspond.