Lost the weight and need your help with the Final Talk

So I need some input on how best to talk about it and when to talk about it. Early in the first couple of years of marriage when crossdressing urges were low - my wife for whatever decided to wear a pair of my underwear one day and she showed me. So I thought, great opportunity - so I wore a pair of hers and showed her and then we talked about it. Some fun times wearing full lingerie together - wearing panties 24/7 - even one day when I purchased some things but found them not to fit me and she said she wished I had modeled them for her. Then comes kids and everything takes a backseat - understandably - I try and restart on several occasions - but shot down - then comes weight gain- weight loss- weight gain - I wore some tap pants on a vacation and she asked why and I said to look sexy and she said the sexiest thing you could do was lose some weight - sigh - still wearing panties 24/7 - they seem authorized - though have intentionally wore plain black nylon - to flash forward to almost empty nesters - and away on a trip and I bring the subject up of how beautiful I think some of the special things she wears are and how I would like to wear them, too - she says you would have to lose some weight - but not immediately negative - 3 or so years later - tried to lose weight - not successful to a great degree - but lightbulb moment - I need a goal- a reminder like a rubber band on your wrist - so I bought some nice chemises to wear at night and used them as my shiny object - now down 50 pounds - she even has noticed - and returning to the same place of 3 years earlier conversation - I want to bring up again - ask for acceptance to wear certain things - no bras - chemise/teddies/camisole/leggings around house/panties - mostly nightwear - an I would like to start on this trip which also happens to be my birthday - so the question is - do I talk to her 2 weeks before trip or a couple days before trip or on the way up in car or when we get there - I don?t want to wreck vacation getaway over this - its obviously important to me but my marriage is more important - so what do think I should do - when should I do it - how to do it - etc?Sorry for the overload here - I guess I am going for the final ?talk? and nervous on an amazing level - but at least I lost the weight and on track to lose more. All help appreciated!

It would be difficult for anyone else to know what your wife my think about all this. It seems you are unsure of how she will respond. So first consider how open your conversations are with your wife, generally. Can you safely bring up things that are important to you and have calm conversations about them?

She is open enough to listen to me and consider it- though not sure of her response - looking for advice on timing - thanks

I suggest having the talk before leaving on vacation. The stress of waiting, hoping and possibly ruining your trip won't help your cause in the future. Maybe a talk over coffee first thing in the morning, maybe shut off the TV turning to her and telling how you feel, what you would like or need. Quality conversation from the heart.

I suggest waiting until after the vacation. Don't risk spoiling the vacation.

Not sure what's best on timing, but congratulations on the weight loss! You must feel great about it!

The timing might ruin the vacation.

I would suggest waiting because it will take time for her to process your talk with her.

Read the link below in my signature on "how to tell your partner"

Firstly, congratulations on the weight loss.

Secondly, I second the notion of waiting until the end of the vacation, if you think it could ruin them.

50 lbs is considerably weight loss. but is it enough?

im a little bit overweight and i know lingerie does not good on my. while my wife and I still play when i am dressed, she says it does nothing for her. im not pushing it until i lose another 20 and stuff starts looking better.

like i said in another thread, lingerie does not look good on everyone

Wow! 50 lbs! That is an achievement!
I think you deserve a reward. Ask if you can buy nightgown or PJs for your birthday. Maybe something from Carol Hochman? They go up to 3X.

Losing fifty pounds is great for your health no matter the outcome of your intent. If you're going to throw the thought out to your wife, do it way ahead of the vacation. Give her sufficient time to change her mind if she says no. If she says no, then do not bring it up again before or during the vacation. Maybe, you'll luck out and get a sexy birthday present from her.

I guess I would come down on the opposite side of when. Let the vacation go by smoothly and without burdening her with some inevitable questions, questions that will not be resolved in one conversation. Consider that a gift of goodwill towards her, and perhaps you will get similar consideration when you bring the subject up later.

Whenever it happens, I can almost guarantee that it will not be the final talk. If it is, then there mayb be problems ahead.

My thought is certainly NOT as you are leaving. As others said, only you know your wife the best. If you feel it will be a difficult conversation and will cause angst, then certainly wait until after the vacation. If you think she is possibly open to more then a couple weeks earlier than the vacation and it may turn out the way you want and you can enjoy the vacation maybe even more. Based on what you have told us, it certainly won’t be the first time you have brought the subject up and I can’t tell for sure her reaction each time, but less negative and more reaffirming about the opportunity to pester you to loose weight.

Best of luck.

I see 2 issues, Paula, your dressing and your intimacy. Has your intimacy increased because of losing 50 pounds? If so, I would bring up your dressing issue after an intimate moment!:o

I have a friend who just lost 40 pounds and is down to 280. He's 5'11". He says he needs/wants to lose 50 more! Hopefully that's not your situation, too?:straightface:

So as to the weight loss - I'm 5'11" and 15 pounds away from my ideal weight according to various websites and the Betty Crocker cookbook. I walk 5 miles a day - I do 75% of the cooking - 95% of the house cleaning - when our first was born - I said I would take on these things to give her more time to relax - 27 years later - as to where I am at in career - my wife encouraged me to take a new job so we would have more time together and I would be happier - she also authorized a new convertible - to replace a car I could have gone longer with - this getaway is basically my birthday celebration and last when we went on this - they had a major storm and lost power - so we went home=no vacation - she has been concerned about my happiness lately - because my old job was horrible - so - if I don't talk to her now as opposed to waiting until after - I likely will just give up and never bring it up - as to the lingerie choices - I have put a lot of time and thought into finding things that look good on my body and are somewhat demur without highlighting the breast area - Rya collection a Wacoal chemises - basically I will always be a man in a dress - but I want to look my best - we all have a lottery ticket - if we never scratch it we will never know if we won or lost. Just looking for the when to talk - thanks -

Congratulations on your weight loss.

If you really feel that there is a pressing need to bring up this topic before the trip, my suggestion would be sooner than later. You didn't specify when this trip is scheduled for. In keeping within the limits of your question, I would suggest 2 weeks before.

That said, I think waiting until after trip is a better choice. Not sure why having the talk before the trip is necessary.

If I were in your situation, I would broach that topic 2 weeks before your planned trip if that's one of the options you are considering. Give your wife ample time to digest this request so as not to potentially destroy the mood and sabotage your trip before even heading into it. No one likes surprises, especially potentially unpleasant ones.

This may also be an opportunity to pro-actively advocate for your own needs, especially since you have been so deferential to the needs of others in the past in sublimating your own crossdressing desires to avoid causing them undue distress. Time to give yourself a pat on the back in front of your wife and in relation to your marriage...not only for the success and perseverance you demonstrated with your weight loss (in part also to placate her), but also to frame this acceptance of your request as a "special" birthday gift that she would be hard pressed to simply blow off dismissively under the circumstances.

I would wait until after your vacation. Why take the risk of ruining it.

The vacation will be neutral ground and if she says yes but it goes sideways - visually it will not be associated with home and it can be put away. We have a good marriage and I can live with it regardless of the direction it takes.

I vote with Char. The sooner the better. To let her digest and ask questions well before your holiday. Which should be about your travel experiences and NOT back home issues!:doh:

Paula, I think your wife will react the same way, no matter when you bring up the issue. The time you bring it up will only add additional questions, such as "why did you wait until we were on vacation to address this issue". I think your last post nailed it, because you can leave it behind you, if things go south.
I am on the positive side that you will have some type of agreement you both can live with. If not, you are back to square one, which is not the worst thing for you.

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visually it will not be associated with home and it can be put away.

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I don't know you or your wife, however, I think this comment would not be true for many women. They will always remember. It doesn't matter when or where you bring it up.

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Originally Posted by char GG

That said, I think waiting until after trip is a better choice. Not sure why having the talk before the trip is necessary.

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I'm thinking that he's hoping that if she seems ok with it then he will be able to have this trip to dress in public away from home with no one knowing..
I really hope I am wrong but ... if thats whats in the plans , please don't.

I agree with Char and the others to just wait..
My first dresser was a Dutchman . I caught him for the first time dressed watching t-porn WITH another dresser online at the time 2 days before we had to fly back to the Netherlands to say goodbye to my mom in law who I adored.. I was in such bad shock that dont recall much of the trip at all other than crying the entire 2 weeks.. it was horrible and horrible for everyone else who could not understand why I could not stop crying and stayed in my room or hid behind my mother in law the entire time. I even attempted to leave back to the states but no one would help me to the train station.

I realize she will not be finding out this final phase like I did the first time, but Its going to be rough no matter what so just let her have this trip in peace. Maybe she will be into it may be not but for sure you can't talk someone into this if they just aren't.

"She said the sexiest thing y"...shou could do was lose some weight"
Remind her of that comment and the lengths you have gone to to lose the weight. Then begin the conversation. My suggestion is to do so as soon as possible. If the vacation is 2 weeks away and the conversation doesn't go well, 2 weeks should allow plenty of time for things to smooth over to allow for a nice vacation.

I'm always a pull the band-aid off quickly type person. Talk to her as soon as possible. Remember, while she may want you to loose weight, the weight may have been an excuse not for you to wear women's clothes. Be prepared for that outcome. Congratulations on the weight loss.

Wow what a dilemma.
Tell her beforehand and risk ruining the holiday or wait till after and have you stressing about what could have been.
I don't envy you at all.
However you know your wife best. How about a nice meal out somewhere and sound her out before committing to any drastic action.
Sorry not to be of more help.

Wow 50 lbs I am jealous so congrats on the weight loss.
I would not ruin the vacation and discuss it after the trip.

Paula, are the kids with you or are you going just together on this trip ?, that would make a big difference on when to ask

As an update to my earlier request for help after weight loss and having the final talk with my wife. I greatly appreciated all the advice given on how to approach this and end the end decided to tell her early and rip the band-aid off so to speak. I started off by asking for her help in getting my body toned back up and then I told her about my motivations for the weigh loss. It went well - baby steps as she said - i reminded her i told her about this a long time ago before we had kids and then we paused for kids - I told her about the things I would like to wear - she said so you want to dress like a girl - I said no - just on the inside and never outside the house - - she did admit I have female and male habits - I think she might have guessed my motivation for losing the weight - especially since she saw me and approved of me getting a tan while wearing a speedo or a bikini as she called it - so I will be wearing a nightgown on our vacation on a trial basis - she did say it may not have the desired outcome I am looking for - so we will see - Thank you all!

The last sentence about the desired outcome what did she mean by that ?

I originally told her way back when that I wanted to look sexy for her and then later I said I found her lingerie to be beautiful on her and I would like to wear something like that as well - hence you need to lose weight - so that was my motivation - so she was saying she might not see me as sexy in it and find it attractive on me - but she didn't say she won't like it all - so hope springs eternal

She hasn?t forgotten. Put her first and then she will see that you concern is for her. Otherwise it is likely to be perceived as selfish.