Big, crazy step

[kaleyg]

Hi everyone. I've been quiet for a while. But something big is coming up -- without going into a lot of explanation, my wife and I are taking an overnight getaway where I will be dressed the whole time. She is not yet accepting, but for various reasons, we're going to try this out. We've been doing some shopping together online in preparation -- and she's picking out clothes that *she* wants! lol We're close to the same size, and she's hoping to get access to them after the weekend. I'll give more updates as we prepare -- the getaway is May 25. She's not keen on taking pictures, but I'm working on it. Pray for us if you pray.

[Julie Denier]

Wow, Kaley! I hope all goes well - please let us know how it turns out. Best of luck and have fun! ;)

[BLUE ORCHID]

Hi Kaley :hugs: , Now that the ball is some what in her court, Just go easy and don't overwhelm your wonderful:love:wife ..:daydreaming:...

[Dana44]

Best of luck Kaley. Hope your wife enjoys it and becomes more accepting.

[Judy-Somthing]

Wow that's sounds so cool, I hope everything goes well.

[Sarah Doepner]

Anticipation can be sweet, but don't let it build to such a level that things don't meet your expectations or you want to press for more than your wife is ready for as well. Communicate and set your boundaries so it turns out to be the best possible experience for both of you. I wish you the best of times.

[alwayshave]

Kaley, That sounds like a great opportunity. Don't push the pictures, let her come around in her own time.

[Rachael Leigh]

Kaley I hope it goes well for you, it's very difficult on our wives to see us dressed and we need to respect that so I wish you well and yes will pray that it goes well for you both.

[Mykaa]

Prayers and Positive thoughts for you both, sounds like a fun time, enjoy your getaway. Sounds like you are very lucky Kaley

[Shayna]

Hope it works out for the best!

[bridget thronton]

Hope it goes well for you both

[Helen_Highwater]

Kaley,

My advice would be to plan ahead as much as possible. If you've not been to the area you're going to before, check it out on Google street view. It may save you from going somewhere that's not "suitable" for a CD'er. Also have a backup plan, something to fall back on should your SO get to a point were she's really not comfortable. Showing her as much consideration as possible will pay huge dividends over time.

Wishing you both a great time.

Helen

[Linda E. Woodworth]

Hi Kaley,

I think this is wonderful and wish you the best on your adventure.

I want to second what Helen's said and add one other thing.

Your wife might secretly hope that doing this will "get it out of your system" and you won't want to do it again. From my reading, this isn't an uncommon thought among the wives. Mine was this way when I first went to Southern Comfort Conference in 2005.

All CD's know it doesn't work that way but that's what the women in our lives tend to hope.

I just want you to be prepared in case this is what she was thinking, especially since she's hoping to get "access" to the clothes after the weekends over.

Again, good luck and please let us know how it turns out.

Love,
Linda W.

[S. Lisa Smith]

Good luck and I hope that you and your wife have a wonderful time!!

[Fiona123]

I hope you and your wife have fun! Enjoy.

[Krisi]

Good luck with your outing (no pun intended) and I hope it all works out for the best.

My advice: Keep it low key. Dress like a woman would dress for the time and place. No six inch heels or mini skirts and keep the makeup to a minimum.

[Pat]

Sounds awesome! Good luck to both of you. Stay flexible. ;)

[Heidi Stevens]

Kaley, I'm so glad that your wife and you have reached a point in your relationship where this can happen! I know you'll have no problems in passing, (the photos of you with your mom are priceless!) so your wife should relax a little once you both are in public and she sees you can handle yourself. Krisi's advice is very good, keep it simple and blend with the locals. A rule I always use when I dress to go out in the "real world" is: would your wife wear what you have on to this?
Have fun, be yourself and Kaley should win over your wife's worries and show her how happy you can be!

[ClosetED]

While this is the time you have dreamed of, it may also be time to consider making it very enjoyable for her, so she wants to do it again.
So splurge and suggest an outfit for only her that she likes (and you can see if she offers to see you in it).
Good luck!
Hugs, Ellen

[raeleen]

What an exciting step, Kaley! I wish you the best of luck on the trip and hope that you and your wife will be able to have some open and honest conversations about this side of you while you're dressed. Even if she isn't yet accepting, and whatever the reasons might be for this trip, it's at least a step in the right direction. Looking forward to hearing more about the trip!

[kaleyg]

Thanks so much for all the thoughts and well-wishes! My wife, who is the most awesome woman in the world, has been on a journey of her own in discovering feminism. I think this has positively impacted her views on transgender people. But I'm still willing to lay it all down for the sake of my marriage.

[Amy Lynn3]

Ellen and I are thinking alike. I know you will have a great time, but what a great time for YOU to make it a great time for your wife to. As Ellen said, buy your wife a surprise outfit and stop by some unplanned location, just because it will please her. Flowers delivered to the motel for her. Take her out for her special meal at an upscale restaurant. Make it one of the most enjoyable trips she has ever had. Your returns will be greater for sure.

[Jenn A116]

Wishing both of you well on this "Big, crazy step". It does sound exciting. There's much to be said for being nearly the same size as your wife. Its a great way to "hide" your femme stuff and to expand both wardrobes.

[reb.femme]

Only got one word for that, immense. This appears to be a major change of heart and I really hope it all works out fantastically.

I mentioned to my wife about going out dressed together last weekend. Her face was blank, not a word to acknowledge my question and she just carried on. So, no time soon then? :heehee:

Becky

[Tina_gm]

This sounds wonderful. She is definitely attempting to broaden her horizon with this. PLease don't overdo it. Be sure to praise her of course, but don't overdo that and smother her with it. Make sure the trip is as much about her as it is for you. I would also suggest bringing some guy clothes in case she does begin to get too uncomfortable.

[sara66]

Good luck, I hope you have a good time.
Let us know how goes.
Sara

[MissTee]

Bet of luck, Kaley. That trip sounds so exciting.

[Fiona123]

Big step, but not at all crazy. All the best.

[kaleyg]

Looks like we're postponing the retreat for June. But we've ordered a couple outfits online, along with a wig, forms, underwear, makeup, accessories, etc. She's ordering clothes that she likes and more in her sizes in hopes of expanding her wardrobe, but I'm not complaining. I would prefer to show some leg, but she likes maxi dresses and skirts. But she has AMAZING taste, so I feel like I'm getting a professional wardrobe consultant. I imagine that she may be thinking this will get it out of my system (someone suggested that), because we're not doing this half-way. When the forms came in the mail, and we tried them out, I think that was hard for her -- it was super awkward for me. I've never worn them before and certainly not with someone looking at me! I found myself crossing my arms to cover up like a girl would. But she helped me adjust the bra to fit with them. I will definitely shave my chest next time before adhering them! (using tapes) OUCH! Fortunately, my chest hair was really only 1/8 inch stubble, since I had shaved for a triathlon a couple weeks ago.
I am a little surprised at how much money she's spending -- she's ordering the make up from her Mary Kay lady (she gets it all at cost). I'm used to buying make up at Walgreens -- the cheapest I can find. I'm assuming the make up is in her colors, too, rather than mine. But we're not that different.
One thing she has made VERY clear is that we will not be leaving the hotel room. I'm hoping that after a bottle of wine, she'll send me down the hall or to the lobby for something. But she is absolutely TERRIFIED of us being recognized. So, I'm trying to come up with fun ideas for us to do in the hotel. I'm also assuming that I shouldn't make any attempt (even after a couple bottles of wine?) toward intimacy. I'm almost 100% sure she would FREAK OUT. But, I'll just see how things go.
Love your feedback and advice! Thanks girls! xxoo

[Diversity]

Good luck to you both, and I hope all goes very well!!! I hope to have such a weekend too, but it is doubtful, at this point in time.
Please post an update, as it would be interesting to hear how things went for you both. I'm sending positive vibes your way, Kaleyg!
Di

[kaleyg]

Ok, the retreat is back on for the 25-26th! We tried on some things yesterday and with the waist cincher and forms I can't believe my figure. The forms & bra are only 38B, but with my waist cinched, they look bigger. I keep wondering what she thinks when she looks at me like that -- is it the way I would feel if she were wearing a fake beard and had a sock in her pants? Or does she think I'm cute/attractive? I guess I'll ask at some point, though I think she would have a very hard time admitting any thoughts/feelings that might make her feel anything but pure heterosexual. And that's fine. Some dresses coming in the mail that I haven't seen yet. Looking forward to trying them on!

[nikkiwindsor]

Kaley, What an amazing experience the two of you are planning! I know you don't take her for granted...from what you've shared w/ us she's someone very special! Nikki

[Beverley Sims]

I say all the best, you have had some good advice from others about not overwhelming the situation, so, play it carefully and let your wife lead.


Don't seek any opportunity to push the issue, I think you are on a winner here.

[Jenn A116]

Sounds like the whole package is coming together. Wishing both of you a very happy experience.

[kaleyg]

Ok need ideas!!! If she doesn't want to leave the hotel room, give your best ideas for a girls night in. ; )

[ClosetED]

You are so lucky!
I would definitely try to keep the interaction to two girlfriends/sisters, and not try any husband to wife actions, unless she initiates.
So certainly with many new clothes and makeup, you can do a fashion show and take along a camera to take pictures of HER and she can choose to take pictures of you. You can sit and have tea,and just talk. She is likely to want to know what thoughts go through your mind while dressed, so bring up some topics like that. Are they the same thoughts as her husband, or more girly? You can watch a chick flick and talk about that and then do a pillow fight at bedtime.
You can play act - pick a scene from the movies or TV and play it out for laughs.
You can be the French maid and let her direct your actions.
Be the masseuse and massage her, but that may be better for her husband to be the masseur.
Just some thoughts
Hugs, Ellen

[Jenniferathome]

Kaley, you need to discuss what she really fears. Is it being recognized only? Your safety? Hers? Something else?

staying in and watching a move is not going to be the same as at home in boy mode. No holding hands, sitting close, etc., right?

When my wife first went out with me she was so nervous for me, on constant alert, she couldn't enjoy anything. And we were in Hawaii! Once I spoke to her and understood her concern, I set her straight: I'm a big boy and can deal with whatever negative consequence may come (none have, of course). Now she has completely let go of any self imposed responsibility for my outing. In her words, "We are just two people out." She can enjoy herself now and see past the "costume." That kind of letting go is not immediate nor simple, but should be discussed.

Good luck

[Alice K]

A wonderful thing is happening to you both. For the hotel plan an exquisite dinner in your room. Table cloth, candles, champagne and wonderful meal. That and a deep and real conversation could be a perfect evening with nothing else planned. May you both have a beautiful evening. And maybe a stroll later in the evening, after dusk in a pretty area if she feels comfortable. Alice

[Diversity]

Good luck to you both. I hope that you both have a lot of fun and celebrate your time in doing this with all the love and mutual respect you each are demonstrating to one another.
Good luck, and I hope you post an update of this experience.
Di

[kaleyg]

We're doing a "dress rehearsal" tomorrow to see how things fit and practice with make up. (I really haven't let on how experienced I am.) Hopefully she is able to get the beard cover down! :heehee: I hope to have a pic of that tomorrow. Maybe even of us together!
Apparently she's read some things on sexual addiction and cross dressing and is hoping that doing this will help break the "addiction". But, in any case, it feels like progress.
I may look different because of the wig she ordered. It seems like she wants to be in control of things.

[Heidi Stevens]

Hey Kaley, as long as she's interested, let her control things this go round! Make adjustments when she's not looking.:heehee: See if she's up to doing a run to Sonic and interact with others. Tell her to watch others reactions. I got a feeling she's going to see every day life! Have fun on the trip.

[kaleyg]

here's a few pics from the "dress rehearsal" today (completely un-doctored!). The one in the bathroom she took, the others I took. I thought the hair style would be fun, but I don't like it in the pics. The dress really seems to give me the inverted triangle -- broad shoulders -- yuk! Hip pads on the way! Probably need more makeup. : ) Not my usual look, but she did a good job. and OMG my eyebrows!!!! aaauugghh! I tried to get her to take a selfie with me, but nope. Maybe next week. ;-)
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[ClosetED]

Again, let her be in control and do what she feels comfortable with. You certainly look feminine, so she needs to be OK with that. She may not be ready for too girly.
Let her do it, then later, offer to make a change and see what she thinks of it.
Hugs, Ellen

[Jenniferathome]

...Apparently she's read some things on sexual addiction and cross dressing and is hoping that doing this will help break the "addiction". ..

Kaley, I am shocked that you wrote this and then followed that it felt like progress. If this is her understanding, cross dressing is like sex addiction and can somehow be "treated" she is a long ways from your understanding of your cross dressing. This is THE discussion you two need to have. What happens when you two return to your house and she thinks it's now over? That you've gotten it out of your system or is now under control? There is life after the weekend....


... I thought the hair style would be fun, but I don't like it in the pics...

The typical,problem with pulled back hair on cross dressers is that it highlights the male jawline. Not something we typically want.

[kaleyg]

Jennifer -- I think, for me, there are two sides to cross dressing: a sexual side and a non-sexual side. The sexual side does feel addictive, like the way other men use porn. I'd love to be rid of that -- it makes me obsess over dressing. and I'd rather spend my sexual "capital" on my wife. But there's a non-sexual side that is just expressing something feminine inside me, and I'm hoping she'll see that and how happy it makes me. once she sees that it doesn't have to be sexual, I'm hoping she'll be more open to it. And I wasn't about to turn down the retreat or her participation! : )

As for the hair, yeah, I'm keeping it down next time!

[Lorileah]

I think you look fine. So many here say you need to "blend" and the hairstyle is one that women would wear at least while driving, to keep the ends from tangling. Also, the shape of your body is fine. The pull to the side helps. Of course hip pads never hurt.

[Heidi Stevens]

I'm with Lorileah, Kaley, if you can round up some hip pads before you go, you'd be 100% to go in my opinion!

[kaleyg]

Hip pads are on the way! Friday night, as part of our "dress rehearsal," we decided I should sleep with my forms in my new cotton night gown. I know this sounds unbelievable, but again, I really think she's hoping this will *decrease* my desire to crossdress. I'm hoping that the retreat will help her become more comfy with the idea of me dressed. We ordered another dress on amazon that is super fun. I'm about 90% sure we'll have pics to share after the retreat.

I'd still love to hear activity ideas, or small ways I can be seen around the hotel without us "going out." I'm just about certain that's not happening.

[kaleyg]

Tomorrow is the big day! I can't wait. I'll start a new thread in the picture gallery on thursday, hopefully. Last minute tips or ideas?

[Linda E. Woodworth]

Good Luck on the great adventure and let us know how it turns out!

Of course we want to see pictures!!!

[kaleyg]

I can't wait! I don't know if the pics will be my best, since I'm not really in charge of makeup, etc. But we'll see!

[nikkiwindsor]

Kaley,

I think you look fantastic in all respects. I don't typically give advice and yet I would affirm what others have shared and let her take the lead and as difficult as it will be try to stay grounded and focused and sensitive to her feelings and what she communicates to you. I hope you have a lovely time together and I wouldn't push to go outside the room unless she floats the idea and even then I would be hesitant to accept the opportunity unless she's absolutely, absolutely ok with you doing it.

Hugs, Nikki

[Connie D50]

Have a great time

[kaleyg]

Good advice Nikki (and others)! I've decided not to push for going out of the room. Even though I'm DYING to show off and try to pass. Ugh! So vain!!
For those of you who pray, pray that we (especially her) would have FUN FUN FUN!!!! FUNNEst time ever!!!! If you don't pray, send some good vibes.