1st Time Dressing Up for My SO

[jennifer215]

Hey everyone. My SO recently found out about my crossdressing (which is a whole other story for another time). She's opened up to me dressing up for her and I'm nervously looking forward to this opportunity. I got a whole new outfit (a cute dress from Nordstrom, matching bra and panties from VS, makeup, and even a new wig). This is definitely has the chance to grow a new level on our relationship, so I'm worried about getting doing this right. I feel like I have to get my look perfect, but I also know it's more than just the look. For you girls who've gone this before, what's your advice for me to make this chance both comfortable and fun for the two of us?

[Amanda22]

Hi Jennifer,

I would just make doubly sure that she's ready to see you all dressed up as a woman. If so, then just be honest with your presentation and ask for her honest feedback. In many cases (mine as well), my wife has been my best coach in dressing. She's helped me tremendously. I've asked her for her help and she gladly obliged. AS a result, crossdressing has brought us even closer together and added an exciting new dimension to our lives together.

Please keep us posted!

[angies GG]

a glass of wine.... make that a bottle!

I'm getting a little more used to him dressing. He still doesn't have a wig so the package is not complet yet, at least for him. I don't know if it makes it easier for me to see he is still my hubby with his regular short haircut or if it would be more comfortable with him having a wig. Looking more than a guy in a dress etc. Either way he is MY husband and I love him. But the wine did help me relax just a bit :-)

Good luck... and have fun!

[Jenniferathome]

Jennifer, I did something little unique, I made a video of me getting ready from total male to female and watched it with my wife. In this way, if she got nervous are wanted to stop she could (she didn't stop it by the way). I did it this way because her biggest fear was that once she saw me in girl mode, would she always see me that way? The anser to that was no.

[ReineD]

Jennifer, honestly just be yourself. If your wife is like most other GGs, she will want to be reassured that you are the same person she loves, no matter how you are dressed. Do go ahead and wear your new clothes since they will make you feel pretty and give you confidence, but your wife I believe is more interested in who you are inside.

The first time I met my SO dressed I admired her style and I thought she looked great, but I found my comfort when we were sitting on the sofa together, cuddling. She sounded the same, smelled the same to me (don't wear perfume the first time), and we talked about the same things. This is when I knew that we would be OK with having the CDing in our lives together.

Just relax and have fun. I'm sure everything will be OK.

[Shelly67]

Reine is spot on as usual . Perhaps there is another option or two , as could I be right in suggesting you'll both be very nervous on first seeing you dressed ? Why not firstly ask if she's really ready to meet your femme self , set up a time date ect , but then also ask her to help you . You never know , you'll prolly have a hoot discovering this new part of your lives together . After all , a womans advice on make up , looks , clothes ect is so invaluable .
Make it fun , make it easy on you both . And if it all goes well , next time you go shopping spoil the lady rotten .

[Cynthia Anne]

I could of replied in many ways until I read Renine's post! I quickly realized that Renine said it all! Hugs!

[anonymousinmaryland]

So far, some very nice posts.

[Tammy V]

Jennifer, I found my wife had an easier time accepting seeing me en femme at first dressed closer to how I do as a male. Female jeans and a female t shirt along with a wig and lighter than usual makeup worked well. Shee ven complimented me on my (cheap and costume) jewelry. It actually took her weeks to want to see me in a dress or skirt but now she is fine with that as long as its a classy outfit.

[kimdl93]

There's little more I can add. My one thought was that perhaps she would like to help you in getting ready. I always appreciate the help with make up and hair...things she's way better at than I am.

Other than that, just try to relax and be yourself.

[Tina B.]

Listen to Renee, the most important thing is relax, and just be yourself, don't try so hard that you are both uncomfortable. If you come across as comfortable, it will help, if you act nervous, you are both likely to suffer from it.Manly make it fun and not stressful.
Tina B.

[Chari]

Great advice from previous posts! Consider asking your SO if she would like to see you in phases, (1st-lingerie, 2nd-dress, shoes, next-makeup, wig) or would she prefer you suddenly become "Jennifer" wearing the whole ensemble. Ask her for an honest opinion of fit, color, texture, makeup, etc - get her involved, and listen to her ideas to make your "coming out" a relaxed enjoyable experience! You have to be comfortable and confident in whatever you are wearing. IMO, there is alot more to being feminine that just panties, heels, makeup, and a dress, but it is a wonderful start.

[Chickhe]

The experience I had was some minor experimentation with my wife early in our relationship, but she is still not exactly comfortable thinking of me looking more feminine decades later. Just the other day she was making a comment saying how its a good thing I don't have less body hair than she does (you could take it two ways I guess)... However, I have dressed up for Halloween and we both enjoy it. I guess she can understand in that context and she gets in to this 'serious mode' where adjusts stuff and tells me if I'm looking good or not. The last time we went out, I ended up passing for the entire night except for some people who noticed my voice, she really got a kick out of that. My suggestion is if you are going to dress with her, then do something fun where both of you can enjoy it...a costume party is good because you both have a costume (you can complement each other). Or arrange some special activity, dinner out, or in where you both dress up really nice. I think what could get boring for her is 'watching you' do it all and her just feeling like a spectator. Maybe bring her shopping with you first and she can help you find a certain look. One thing to watch out for is feeling too good about it and having her not want to spoil your mood by telling you what she really thinks... you may hear about it months later, so what I suggest is to go slow and let her talk a lot and listen to what she says and ask her what she feels etc.

[LolaDD]

Jennifer,

I would suggest baby steps to you. When I first discussed the idea of dressing up she was very supportive and gave me a budget for my first outfit. I had a great time purchasing the bras, panties, makeup, shoes and especially the breast forms. She was a little uneasy when the first time she saw me because it was such an extreme transformation. She didn't think I could come close to looking very passable but to my surprise I did a very nice job dressing up but she was very accepting anyways. The only thing she was very uncomfortable with was the tucking. We had a wonderful first evening together at home. We played a board game and watched a movie together. We discussed taking things slow and keeping our communication open. She even named me Lola.

I have only been dressing in front of her for about a month now but since that time I have worn my breast, panties and a nightgown around the house several time in front of her without makeup, hose and a wig. She is getting used to that appearance and has no issues with it. She even has encouraged me to wear some things cause it makes me feel very relaxed. The next thing I did was start an e-mail account for Lola and we e-mail each other on a daily basis to see how the other is doing and we chat as women on yahoo chat once in a while. Both help both of us open up on how we feel, especially me as a woman. Last weekend she even surprised Lola and bought her a new bra, panities and hose and we are talking about going out of town for a weekend as girls together.

I feel that I am the luckiest girl in the world and if you take the time to listen to her feelings you can have the same wonderful experiences that I am having right now. Good luck to you and please let me know how it goes.

Lola

[JamieG]

This is all great advice. I'd like to add this: be sure to give her a chance to change her mind right before you dress up for her; if she's had a bad day it may just completely ruin the experience for both of you. Also plan an activity that you can both enjoy together while dressed. But if she sees you and says she's seen enough, be prepared to go back to drab without getting moody.

[suchacutie]

What a great group of ideas! One of the strengths of this forum is the breadth of experiences to be shared.'

My wife and I started together from the very beginning of my dressing, so there was nothing that she didn't see right from the start. Having said that, even she was surprised at the difference the first time that Tina appeared wearing her new hair and breastforms. She thought it was fantastic and that started a whole series of conversations about just WHO Tina is.

And that is the emphasis I would like to add to this discussion. Reine touched upon it, but her experience is very different from mine. In my case Tina and my wife are girlfriends. There is no cuddling, and Tina definitely does NOT smell anything like a male . Heck, even the dog knows when Tina has arrived!

The range of just who Jennifer might be is immense. My wife and I talk about Tina all the time, and then she and Tina talk about me. For us, Tina is a third person in our relationship. Tina is fastidious to a fault, and loves dealing with detailed things like crochetting and organizing. Last time she visited she totally rearranged my side of our walk-in closet, and she was just ruthless about throwing things out...sheesh! There are so many times that Tina has suddenly asked my wife about an issue growing up, and how growing up as a girl in that sense affected her. Your SO has a wealth of experiences that you haven't had, and I'm sure she'd love to tell Jennifer about them! With us, the greeting is an air kiss. Do you know how you will greet each other for the first time? Also, you can expect that your SO will suddenly realize that she doesn't know Jennifer, and will probably have her own questions. My wife often asks Tina about what's happening in her life.

It may very well be like meeting someone for the first time, and it might have the aura of a blind date in many ways. I would suggest trying to talk about that "date" ahead of time and plan it out a bit. Will there be dinner. Will you make dinner together. Will it be something totally new so that that your SO and Jennifer start of a new experience, or do you both want it to be something you've done together in your male mode?

And lastly, the idea of letting her call it off, even at the very last minute, is a good idea. There is no rush, really, and if she does you'll have even more to talk about. If she does call it off at the last minute, ask her if she's ever experienced that situation from the other side. Converse, converse, converse

Let Jennifer be herself as best as she knows how. It's likely that after this first "date", Jennifer will begin to evolve as yet another link in your relationship is forged!

Best,

Tina

[LolaDD]

Jamie, what great advice. Actually, her first date with Lola was supposed to be on a Saturday but she wasn't feeling very well and we moved it to Sunday. We had a great time.

Tina, Tess and I talk about Lola all the time as well. She is the third party in our relationship. One one occasion I was in a giddy mood and e-mailed her and asked if she wanted to have a girls night out and go to the Coach store. Lola needed a new handbag and wallet. She called me up and told me no way is that bitch going to have a more expensive purse than she does. Lola had to settle for a Vera Bradly bag on sale.

This is a great forum to have may I add. All you girls are helping me with being Lola. Thank you all very much. I just wish there was a way to get to know some of you and possibly exchange e-mails or even chat. Does anybody have any suggestions?

Lola.

[ReineD]

This is all great advice. I'd like to add this: be sure to give her a chance to change her mind right before you dress up for her; if she's had a bad day it may just completely ruin the experience for both of you. Also plan an activity that you can both enjoy together while dressed. But if she sees you and says she's seen enough, be prepared to go back to drab without getting moody.

My SO also did this, but for us it was after the first few months of our relationship, after we had done many things together dressed, on a night where it all became too much for me.

We had met in a city a few hours away where she had spent the afternoon getting her hair and nails done. She was wearing a beautiful new outfit and the plans were to have dinner, then attend a lesbian group's ballroom dancing evening. I arrived at the hotel closer to dinner time, somewhat harried because I had had difficult things to attend to at home. I saw just how much she was glowing after her afternoon of pampering and my heart sank because I thought she was more pleased about her transformation and the upcoming evening than being with me, as sad as this now sounds now. I didn't have a lot of time to get ready myself but I did, we went to dinner, and then when we walked into the place for the dancing my heart literally sank when I saw all these women there. They were playing a very romantic song from my past, "Lady In Red", and all of a sudden I felt an intense desire to be in my old life again with a man and not with a woman.

I've got tears in my eyes as I'm typing this, but the evening didn't progress well for me as I felt my SO was much more interested in how the lesbians were dancing together than anything else. I'm not by any means a drama queen, but I just became unraveled after having been there about 2 hours. I started to hyperventilate at one point when my SO was staring particularly intensely and this one lesbian couple doing a very sexy and sensuous tango together, and not wanting to create a scene I told my SO I just couldn't do this any more and I needed some air. I took my purse and went outside. She followed me and once outside everything came out. I was crying by then and I told her that I didn't think it would work because I wasn't the lesbian she wanted me to be, she was just with me out of convenience, and I thought she would be relieved if I broke up with her so that she could go ahead and have her relationships with lesbians. I was really quite beside myself.

By this time we were sitting in the car, she listened to everything I had to say, and it was then she told me that she valued me and our relationship more than being dressed, and if ever I didn't feel up to doing anything dressed I should just say the word and she would revert back to guy mode gladly, even if we had just spent a lot of time getting ready to go out.

I was floored because I had no idea she felt this way. I thought that nothing in her life compared to the pleasure she felt in being herself, not even being with me, and if she felt this way who was I to tell her to not be a woman, so therefore we had no future together because I was not a lesbian. And on her side, she had no idea of all the turmoil that had been building inside of me. As soon as she said what she had to say, all my angst disappeared and I've never, not once, ever felt the need to ask her to revert to guy mode when she was dressed.

Sorry for the long story, and I hope that reading this now won't make you more nervous than help. But I did want to show you a slice of what I went through and what I imagine many other GGs go through before they understand what this is all about.

[kimdl93]

....... I saw just how much she was glowing after her afternoon of pampering and my heart sank because I thought she was more pleased about her transformation and the upcoming evening than being with me, as sad as this now sounds now. I didn't have a lot of time to get ready myself but I did, we went to dinner, and then when we walked into the place for the dancing my heart literally sank when I saw all these women there. They were playing a very romantic song from my past, "Lady In Red", and all of a sudden I felt an intense desire to be in my old life again with a man and not with a woman :

My greatest fear remains that we reach some tipping point for my SO...that like Reine describes above, a point when my SO might feel that she is no longer important as dressing in my life. Whether its at the beginning or long into a stable relationship, its important to keep this in mind.

[ReineD]

My greatest fear remains that we reach some tipping point for my SO...that like Reine describes above, a point when my SO might feel that she is no longer important as dressing in my life. Whether its at the beginning or long into a stable relationship, its important to keep this in mind.

If this ever happens, Kim, all you need to do is reassure her, like my SO did. We grow up to believe that all men behave or are motivated in the same way as the men we see around us and this simply doesn't fit in with a CD's motives for doing things. It does take a while to change these fundamental beliefs, just like it takes a while for the average CD to stop rejecting his femme self. Even when we do learn enough about the CDing to stop feeling threatened (with the idea that we are not enough for our SOs and this is why they CD), even when we become totally supportive, these old beliefs will come to the surface once in awhile, especially when we feel vulnerable. Certain fundamental beliefs almost become hard wired, I think, especially beliefs about gender or dininity.

If the relationship or the marriage is in good shape and there isn't a slew of hidden resentments over other related or unrelated issues, it is simply a question of having a good, honest, heart-to-heart in order to push back the old beliefs again about how a man is motivated.

I also want to add that the reassurance also has to go hand in hand with a behavior that demonstrates to the wife that she is important to her husband. I've read stories here of CDs in pink fogs who get quite impatient with their wives when they share their insecurities, thinking that their wives should have "gotten it" by now, and who continue to do what they will covertly. This just reinforces a wife's belief that her SO's femme persona is like a mistress who is infinitely more important to her husband than she is.

[Misti]

1st Time Dressing Up for My SO
I'm worried about ... doing this right. I feel like I have to get my look perfect, but I also know it's more than just the look.

I've got tears in my eyes as I'm typing this.... because I was not a lesbian.... Sorry for the long story... [B]ut I did want to show you a slice of what I went through and what I imagine many other GGs go through before they understand what this is all about.

Reine, you are something INCREDIBLY SPECIAL, WHAT A JEWEL YOU ARE!
I, too, had tears in my eyes reading your post today. I left the "not a lesbian..." in there because "only just last night" my SO and I had an identical discussion about my dressing. She said she was not going to kiss me "when I get my wig," because she was "not a lesbian!" I said that is alright because, "Sex monts ago I cun't evn spell Letsbeone, now I are one!" (Pun Intended: Takeoff on an ancient U.S. Air Force bit of humor about becoming a "pylut!" (Pilot))

The significance of her statement is incredible because it tells me that her "total resistance till now" to my completing my 24/7 dressing (i.e., with makeup and wig) is now a near-certainty in her mind. I am nearing the final stages of being 100% female in my dressing after a humongous, long, stressful struggle! Hoorah!

So what this means to our "mutual interest" thread here, Jennifer, et al., is patience, love and trust in those beautiful SO's is so "INCREDIBLY SPECIAL" that we may oftentimes tend to overlook them in our complete joy, self-satisfaction, self-centeredness and selfishness throughout our marvelous, miraculous, stupendous transformation journey.
No way Jose! They are priceless and are definitely (our) "Keepers!"

Best of luck Jennifer, I hope to be the next in line when you throw your bouquet. Bon Voyage!

[LolaDD]

This post has taken one heck of a turn. L.

[ReineD]

This post has taken one heck of a turn. L.

Yeah, sorry if I took it to the next few steps after the first meeting, but I think these are all important considerations for a CD to keep in mind. I don't think it can hurt to read what his wife's thought processes might be, and perhaps avoid any pitfalls.

My issue is that I have a hard time relating my experiences in 25 words or less.

[AmyGaleRT]

No, no, please do keep talking, Reine. I, for one, am keeping this in mind, because, assuming I manage to put my fiancee in the picture (which is necessary, I merely have to grow brave enough to do it), she and I will need to deal with these kind of situations, and your first-hand experience is worth keeping in mind for dealing with analagous situations.

So talk all you want, I shall merely sit myself at your feet (carefully arranging my dress as I do so, of course, so as not to give out any "free shows" ) and learn.

[Kaz]

Reine, as usual your words are pure magic in our understanding of this from the SOs perspective.. and yes, this does inform the 'first meeting' scenario because everything that happens after that will stem from how this first one pans out.

Jennifer, I can't really add anything to the words of wisdom here other than saying that I truly admire what you are doing and I hope it all works for you. My thoughts are just these, and stem from my own desires and self-doubt... I would want to look my best and be the most convincing female I could achieve in order to show that I can do this...BUT.. would my SO want to see this? Or would she want to see something she could relate to better? As Kaz I am so unlike my drab mode self it does look like a different person... I guess this could be really wierd if I presented full on Kaz to her...

So all the comments are great... take them on board and do let us know how you get on!