First time CD'ing with new friend not so successful

Hi everyone,

As some of you may know, I recently befriended a woman who is really supportive of me experimenting with crossdressing. It was something that was always in the background for me and a very closed, private affair.

I went to see her at her house today and she took me through some make-up; eyeshadow, eyeliner, skin care, mascara, lip gloss/stick/stain. She had some stockings for me to try on. At this point I was feeling very emotionally exposed but I went with it. She tried a corset on me but I began to feel quite scared.

It was quite a shock to see myself made-up. I don't know how I feel about the whole thing. I felt upset and a bit tearful on the way home; maybe embarrassed and wounded by it all. I told her I didn't feel great about it.

I feel pretty sad and upset now. It wasn't how I envisaged it to be. I guess it's about identifying my comfort level with the whole thing to know where it goes.

TO

I'm sorry you had that experience, but I can also relate to the sensation. Maybe not with regards to crossdressing, but I've been in other situations, where I've looked forward to something really bad and then it just didn't turn out as well as I had hoped and imagined in my mind. Luckily, so far I haven't had that experience with crossdressing, but maybe I will. I've not yet tried crossdressing with/in front of my girlfriend and maybe that'll turn out to be really awkward? I hope not, but I can see how it could be, so I (think I) understand what you experienced.

Not really sure what to advice you to, other than I don't think you should let this knock you out. I still think you should try crossdressing again, maybe alone next time? If you've come as far as you are, letting a woman help you get dressed, I don't think it's because you really don't like crossdressing. I'd say, give it another chance! But then again, I'm far from any expert.

Wow. It sounds like a fantasy to most of us. But in reality I wonder how it would really play out. I guess it was a little more than expected. I can certainly understand how it kind of took you by surprise especially the embarrassment. I would say talk to her about your feelings. Have you crossed dressed by yourself before. I mean makeup, wig and all the rest. Good luck with it. The rest of us will only dream about it.

I'm sorry that you had such a experience sweetie, but I do hope you don't give up on crossdressing because of it. Maybe you weren't too used to dressing in front of others, and it was too much to take in. So maybe try to dress up on your own for now and take it slowly and get more comfortable with your look.

To much to fast, Start over, just talk to her about all this, and as your comfort level increase so will your acceptance. It a slow process one that take years, sometimes, tell her not to give up on you, some of can't show our self to our wife, not because they are not accepting because we have a hard time accepting our self. Don't be up set at her or your self, it a process of accepting, talk to her and tell her how you feel.

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Originally Posted by Sallee

Wow. It sounds like a fantasy to most of us. But in reality I wonder how it would really play out. I guess it was a little more than expected. I can certainly understand how it kind of took you by surprise especially the embarrassment. I would say talk to her about your feelings. Have you crossed dressed by yourself before. I mean makeup, wig and all the rest. Good luck with it. The rest of us will only dream about it.

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I've crossdressed before on my own but it was a very long time ago and I only wore lingerie. I never was brave enough to do make-up, wigs etc so yes, maybe it was too much, too soon.

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Originally Posted by Annaliese

To much to fast, Start over, just talk to her about all this, and as your comfort level increase so will your acceptance. It a slow process one that take years, sometimes, tell her not to give up on you some of can't show our self to our wife, not because they are not accepting be cause we have a hard time accepting our self. Don't be up set at her or your self, it a process of accepting, talk to her and tell her how you feel.

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Yes, I agree. It seems like it was way too much, too soon. I'm not upset at her, she's been incredibly understanding and supportive. I just don't want her to feel bad about it all too. Once I think it over and let it all digest, we'll speak again.

TO

I think I can empathise with this, TO...

I believe I had similar feelings when I first began experimenting with wigs and then later, makeup... the real shock - as a closeted dresser and without ever dressing above the neck - was the first few times you have to view your face in a mirror where previously there was just something of a headless and anonymous body... if you've been doing this for some time or from some time back, this new imagery can take quite a bit of getting used to, I'd suggest - so yes, this is probably too much, too fast and you need some time to absorb this new feeling and perspective and make your progress more gradual. :)

You will get over feeling sad and upset - and the desires to dress will likely come back... perhaps just pace your progress a little more and you will find it easier to get used to those new feelings and gain self-acceptance...

I feel this is definitely a good time to Keep Calm & Carry On! :hugs:

Katey x

I've had that happen myself, I got offered a free makeover but I made all the excuses under the sun to not go..
Kind of regret that now.
i also had my friend give me 4 bags of her clothes and shoes because she had lost weight, we were supposed to dress up together but that hasn't happened yet.

Not to worry my friend. We hone our female skills as we go along. It takes a bit of time.I've been at it for some 55 years now and am still learning. :battingeyelashes::)

That creepy little voice in your head got to you. You know the one your parent or whatever told you it was "wrong". Don't sweat it. Also expect a post dressing "drop" where you feel a little low after the rush wears off. It is normal. :)

When I saw the heading I thought you had shown someone yourself and they were not over enthusiastic.
Reading your post I think you have to overcome the personal guilt feelings within yourself that have taken a lifetime to evolve.
Go with your friends suggestions and enjoy what she encourages you to do.

Hi TO,

It is one thing to dress in the privacy of your own home and another to share it with someone. Remember you are going from a position of control (your guy self) to a loss of control position as another person helps you transform. You stated later you have never done make-up, wig and so forth so I can see how the whole thing was emotionally draining. We all have a concept of what we expect to see the first time we don make-up and wig. Call her our "internal woman" and to us she is beautiful . . . However the first time you look in the mirror you don't see "her" you see a "dude with make-up" and that can be quite disconcerting. It took me awhile to actually stomach looking at myself in the mirror and I truly avoided them after I was dressed for some time. However, once you get more comfortable this feeling should wear off.

It sounds like you have the potential for a good friend in this thing we do. I would go back and discuss what you felt and perhaps agree to go a bit slower. Perhaps try a few make-up sessions and get immersed in learning, take a peek or two in the mirror and get used to seeing yourself in make-up. Progression normally stems from there.

Hugs

Isha

Hi TO, Isha makes a very good point I couldn't have said it better.
Please keep us advised of your progress with this lady.:daydreaming:

This is the kind of position that a lot of Crossdressers would love to be in.

Thanks Isha, what you said there means a lot and rings true. I tend to overinvest emotionally in things and when they inevitability don't live up to the ideal in my head, I get my heart broken. It takes me several days to get over stuff like this and I feel really down right now. I know it will pass.

I'm sure my friend will be understanding. I can struggle with setting boundaries and being honest with how I feel and I don't want to negatively impact the relationship with that.

TO

It takes a lot of nerve to let someone in like that, and it doesn't come easy the first time. Especially if you, like me, are a very introverted, shy person to start with.
The transformation process where I become Amy is very very personal. There are parts of that process that I am very self conscious about, and sharing that with someone else requires an extreme level of intimacy.

There is only one person in this world who has ever (and probably will ever) share that with me, and that's my wife. To this day, there are parts of it I still feel uncomfortable about ... I still don't like my wife to see me putting on my breastforms, tucking, etc. Now after it's all over and I'm lookin' good, I don't mind people seeing me, but the getting there is too personal.

I remember the first time I let my wife in like that. I had a plenty good time while it was going on, though I was a bundle of nerves. But afterward I was run over by a truckload of insecurity, like you're describing. After a week or so of my wife continually reassuring me (and getting sick and tired of my insecurity I think, LOL), I finally got used to the idea that it was ok to share this with her. After that, everything became a lot more fun.

From your post, I'm not sure how close you are with your new dressing friend, but I suspect if you give it some time and take it slowly that you'll warm up to it :-)

It's funny, I have problems with the SO being present for the transformation...

I'm not sure I could dress in front of someone under those conditions either. When I came out to my wife it took me quite a few times being seen dressed by her, much less dress if front of her. Someone that is just a friend, it would be even harder.
Dressing is such a personal thing, and one most of us have kept hidden from the world, it's hard to open up to someone, and expose your inter most vulnerable self to them. I'm sure a lot of it was just nerves, it sounds like you had the right lady, just need to get used to the idea of sharing that part of yourself, and that can be the hardest thing to do.

Hi The Opt, i tried the complete transformation with my wife and found that she gave me compliments and said i looked amazing...did your friend comment on anything during the process .. sometimes we need reassurance to wipe away the insecurities ..I hope you feel better and it works out for what makes you happy

She asked me what I thought of each process; the mascara, eye-shadow, eyeliner etc. I didn't really know what I thought of any of it. I didn't know what my
"colours" were. I was confused. She didn't stroke my ego or tell me I looked beautiful etc. As kind and supportive as she is, I don't get the impression that she would. She won't BS or sugar-coat things.

TO

I would take everyone's advice here. My advice is too not use much make up. I can sure relate to being overly invested emotionally, and super nervous, as I feel that that, before i seldom go out, or meet an admirer. I very seldom go out, and am super cautious about meeting any admirer.

When you feel like CD again maybe experiment with small steps before fully transforming and try it without anyone around

Wow, having a supportive (and maybe even an encouraging) SO is the enviable position of many CDers here. Regardless, since you were uncomfortable with the process/experience, then let her know. If she is open enough to dress you then surely she if open enough to understand it may have been too much too fast. Something to consider: perhaps she was simply giving you something she thought you wanted. If so, that's another data point along the trajectory that you've hit the jackpot in finding a desirable GG regardless of CD inclinations.
Best of everything to you Optimist!

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Originally Posted by SamanthaSometimes

Wow, having a supportive (and maybe even an encouraging) SO is the enviable position of many CDers here. Regardless, since you were uncomfortable with the process/experience, then let her know. If she is open enough to dress you then surely she if open enough to understand it may have been too much too fast. Something to consider: perhaps she was simply giving you something she thought you wanted. If so, that's another data point along the trajectory that you've hit the jackpot in finding a desirable GG regardless of CD inclinations.
Best of everything to you Optimist!

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Yes, for sure, I so appreciate what she does for me. It's a unique relationship, unlike anything else I've ever had. I've struggled greatly with intimacy and emotions all my life and I know how withholding how I feel and being evasive badly affects trust and closeness in relationships. I would be really upset if it meant she thought she'd have to censor herself or and adjust who she is around me. I have to be brave and be as honest as possible with her for she is very special indeed.

TO

To give up the control is one thing I really related to in this thread. We are conditioned as men never to seem vulnerable. To keep the stiff upper lip, to show people we're a man, to be brave and protect, not to feel or show emotion much less cry over something as beautiful as a newborn or when you child is hurt. Then to turn ourselves inward to the core person we've been told shouldn't be there but is so much a part of us. When we give up that control and someone actually see's us is the end of that control no matter how reassuring anyone can be. Guilt, paranoia, self ego shattering. But if your lucky enough to find a lady that goes along with you wow the fun you can have after you've grown into yourself would be unreal. I only wish I could find someone open minded enough to accept me as that!! Don't give up CONTROL is much mre over rated than it really is!! Have faith you'll make it!!

I'm going to share a sort of related issue.

My current SO, wanted to be really accepting. She would ask me to get dressed, but treated me as a different person. So much so that it really was uncomfortable for me.

Expectations VS reality can be a bit rough, no matter what remember you are a great person.