Careful what you ask for

[Jillian-TG]

Ok so here's my "problem" which I should be excited about yet it scares the living daylights out of me just thinking about it.

I'm still new on the forum but if you look at prior posts you will see I've mentioned that my wife and I cruise often and she's been ok with me dressing as a woman occasionally while on the cruises. I'm still somewhat confused on my own label - not sure if "cross dresser" sits well with me anymore and I've used the word "trans" a few times when chatting with my wife. My wife is what I would consider as "tolerant" of my feminine tendencies and she has said many times she prefers my masculine side. So she has not accepted my girly side but she tolerates it. I've embraced that tolerance as a compromise and we've been happily married for almost 30 years. As I've aged I've become more and more feminine. Definitely more trans than the CD that I thought I was. We love each other and my wife tries her best to understand. Our cruises are an escape and rest for us. We are best friends.

The most recent trip I dressed more often than usual and I was very happy and we had a blast as friends and as a couple. We chatted a lot about my femininity and her comfort level on me coming out the closet. I basically said that we were having a great time because I was finally being my true self and that she would actually prefer me and like me more if I was allowed to come out the closet and just be myself all the time.  For the first time ever she started to warm to the idea - just a little. We discussed the kids, family and the church.

We then discussed the need for her to experience me 24/7 as a woman rather than just some occasional dressing in the evenings while on a cruise. I casually suggested we do a full girls trip where I could be a woman fulltime. It would give her a chance to see the real me for an extended period of time. Surprisingly she agreed. So we booked a cruise for the end of March based on an agreement that I would present as a woman 24/7 while we are in the ship - from dinners to going to the pool. I was happy with the idea (obviously!!!) but truthfully I am also scared to death. Yes I've been out in public as a woman but it has been small outings that felt VERY controlled.  All of my outings are in the evening and I don't really interact with other people who are always at a distance. This time it's going to be 24/7 and more personal because it will include a lot of close face-to-face interaction with people especially in the restaurants. In terms of passing I would say that I definitely do not pass but I look ok in female mode.

I've struggled with my wife for 30 years to accept this side of me and never in a million years did I think she would ever be totally ok with it. Even after agreeing to a girls trip I still thought she would eventually land on it being more of a part time thing but maybe where I could dress more often than usual.

Nope. Yesterday she gave me a bikini outfit for the pool. I would have lost a bet on that one. For sure I was positive and expecting her to draw a hard line on a bathing outfit yet there she was casually discussing outfits and not fussed about the idea of me in a bikini next to her in the broad daylight. My head is still spinning but I acted cool about it while dying inside.

I desperately want to do this and experience a week as a woman. My motivation is that just maybe she will love the real me and say to heck with it - "come out the closet and live your truth"

I literally have an opportunity to get my wife onside with me coming out the closet. I know without a doubt that we would be so much happier if I could live my truth. I'm a much nicer person when I can be myself.

But I am so scared to do the cruise. I also have a solo cruise booked a few weeks prior to the March girls trip with my wife. On that solo trip I can first test the waters (no pun intended) so I will have to use that opportunity first I suppose.

As they say - be careful of what you wish for   

[Northern Star Girl ✅]

@Jillian
Dear Jillian:
Yes indeed, you have seemingly obtained what you were wishing for.
 
You perhaps should "consider" the solo cruise and be in 100% female attire...
...including the Bikini that your wife gifted you. 

Once out of the pool water you can put on a cover up over your bikini.

On your google search line put in "Women's Beach & Swim Cover Ups"
and you will find a wide variety of options.

Have fun exploring your feminine self.

HUGS, Danielle [Northern Star Girl]

[Pema]

I know nothing about cruises, so please forgive the naïveté of my questions:

• Is it required that you wear a bikini? If it is, weren't you anticipating that piece when you suggested the trip?
• Is it possible that your wife is testing your resolve?

[Northern Star Girl ✅]

@Pema
Dear Pema:

No...... When cruising or any vacation, swimming, wearing swimwear, etc,  is  NOT A  REQUIREMENT

While I am not certain WHY that Jullian's WIFE offered her a Bikini....
...perhaps being nice and giving a feminine gift.? ?

Danielle

I know nothing about cruises, so please forgive the naïveté of my questions:

• Is it required that you wear a bikini? If it is, weren't you anticipating that piece when you suggested the trip?
• Is it possible that your wife is testing your resolve?

[Lori Dee ✅]

I have zero experience when it comes to cruises. I have been single and live alone since my transition, so take this with a grain of salt.

If I were in that situation, planning would be my priority. You are not just going out for an evening, you are going out for a week. So plan accordingly. What supplies will you need for the duration?

Plan for every day and part of a day.
What will you sleep in?
What will you wear in the mornings when you get up?
What will you wear if going for a walk on the deck?
What will you wear in the evenings, for dinner, dancing, or whatever?
You have the bikini for the pool. Are you comfortable wearing it as is? Or will you be more comfortable with a skirt or cover-up, as Danielle mentioned?

Once you have planned out every outfit, what happens if the weather changes? Will that still work, or do you need a backup outfit just in case?

I think you have a prime opportunity here. Just be yourself. I am most comfortable in jeans, a t-shirt, and tennis shoes, so that is what I wear. I would never be comfortable in a beautiful sequined dress, so I don't wear them. When you are comfortable, you can relax and enjoy yourself more. When you have a well-thought-out plan, that is one less thing to stress about. You are not trying to impress an audience; you are going to have fun.

Then, as suggested, use your solo trip to test your plan. Note what worked and what didn't. Tweak it as needed. Come March, you will be dragging your wife to the boat! Have fun with it. It should never be difficult to just be yourself.

Maybe your wife is just curious about how far you want to go. Will you wear fancy sequin and rhinestone formal gowns every day, all day? Or will the real you just want to hang out in comfy PJs when going for breakfast? She needs to see what the real you looks like to her. That is how she can make an informed decision about how she feels about all of this. The fact that she is open to trying it out speaks volumes about your love and bond.

That is special.

[Jillian-TG]

I know nothing about cruises, so please forgive the naïveté of my questions:

• Is it required that you wear a bikini? If it is, weren't you anticipating that piece when you suggested the trip?
• Is it possible that your wife is testing your resolve?

Lots of pools and hot tubs on the ships so most everyone is in swimming attire if the cruise is in a warm climate. Various types of bathing outfits from bland to riske.

I did think about whether my wife is testing me but she seemed genuinely invested in the process and appeared to want to be nice about it. After 30 years with her I would know if she was trying to push my buttons. This was sincere which has really taken me aback (in a positive sense).

[Jillian-TG]

I have zero experience when it comes to cruises. I have been single and live alone since my transition, so take this with a grain of salt.

If I were in that situation, planning would be my priority. You are not just going out for an evening, you are going out for a week. So plan accordingly. What supplies will you need for the duration?

Plan for every day and part of a day.
What will you sleep in?
What will you wear in the mornings when you get up?
What will you wear if going for a walk on the deck?
What will you wear in the evenings, for dinner, dancing, or whatever?
You have the bikini for the pool. Are you comfortable wearing it as is? Or will you be more comfortable with a skirt or cover-up, as Danielle mentioned?

Once you have planned out every outfit, what happens if the weather changes? Will that still work, or do you need a backup outfit just in case?

I think you have a prime opportunity here. Just be yourself. I am most comfortable in jeans, a t-shirt, and tennis shoes, so that is what I wear. I would never be comfortable in a beautiful sequined dress, so I don't wear them. When you are comfortable, you can relax and enjoy yourself more. When you have a well-thought-out plan, that is one less thing to stress about. You are not trying to impress an audience; you are going to have fun.

Then, as suggested, use your solo trip to test your plan. Note what worked and what didn't. Tweak it as needed. Come March, you will be dragging your wife to the boat! Have fun with it. It should never be difficult to just be yourself.

Maybe your wife is just curious about how far you want to go. Will you wear fancy sequin and rhinestone formal gowns every day, all day? Or will the real you just want to hang out in comfy PJs when going for breakfast? She needs to see what the real you looks like to her. That is how she can make an informed decision about how she feels about all of this. The fact that she is open to trying it out speaks volumes about your love and bond.

That is special.

Good questions. I will definitely have to plan and I know that 95% of the time I will NOT be all glammed up. That's not how real women carry themselves. Most of the time it will be girly shorts, t shirts and flip flops. I will take some dresses for the evening. And yes my wife was already suggested a cover up for the bikini :-)

[ChrissyRyan]

I had my first experience with women's swimwear last year.  It was one piece, not counting the swim skirt, and it too was a gift.  I have never been on an ocean cruise but I did get to be on a small but very nice boat. Plus on beaches.  Perhaps I will mention this in my blog. 

I mention this as I am surprised that you got a bikini as a gift! 

There is a lot to present as a woman I would think on a cruise if you have not lived as a woman.  You may wish to ask Emma, see her blog. 

Plan this all out the best you can and perhaps most of the suggestions by other that post replies will be of help.

[Jillian-TG]

Fortunately I have some time to process all of this and to plan it out properly. And I have my solo trip prior to it to test some things out. As I mentioned I've only ventured out as a woman in situations where I've never really interacted with anyone. I've just been walking around and keeping my distance. This girls trip is going to be a lot of firsts for me interacting face to face with people. I'm scared but excited too. 

[Lori Dee ✅]

This girls trip is going to be a lot of firsts for me interacting face to face with people. I'm scared but excited too. 

On your solo trip, don't push yourself too hard. You are still testing to see how it goes. For interacting with others, you don't have to be the one starting conversations. Friendly greetings are always easy. But put yourself in a place where others have an opportunity to greet you and perhaps strike up a conversation. There may be others there traveling alone and would just like someone to talk to.

[Susan ✅]

First, let me say this clearly: what you're describing isn't a problem. It's a breakthrough!

Your wife — after 30 years of "tolerating" your feminine side — just handed you a bikini and started casually discussing pool outfits. She agreed to a full girls' trip where you present 24/7. She's not drawing hard lines. She's opening doors.

And you're terrified. That makes complete sense.

Here's what I think is happening: you've spent three decades managing expectations, negotiating for crumbs, and protecting yourself from disappointment. You learned to want small things because small things felt survivable. Now something big is actually possible, and your nervous system doesn't know what to do with it.

The fear you're feeling isn't a sign that something is wrong. It's a sign that something real is at stake. You're not scared of failing. You're scared of succeeding — and what that might mean for the rest of your life.

Let me address a few things:

On passing: You said you "definitely do not pass but look ok in female mode." Here's the truth — on a cruise ship, people are on vacation. They're relaxed, they're drinking, they're focused on their own good time. Most won't look twice. The ones who do notice will mostly mind their own business. And the handful who might have opinions? You'll never see them again. A cruise is actually one of the safest places to test extended presentation because it's a contained environment with a built-in exit date.

On the solo cruise first: This is smart. Use it. Test everything — the restaurants, the pool, the face-to-face interactions you're worried about. Figure out what works, what needs adjusting, what you're comfortable with. By the time the girls' trip happens, you'll have real experience to draw on, not just fear.

On your wife: She's not just tolerating anymore. She's participating. She bought you a bikini. She's discussing outfits. She agreed to 24/7. That's not a woman who's holding her nose and enduring something unpleasant. That's a woman who's genuinely trying to meet you where you are. Don't underestimate what she's offering.

On the label question: You mentioned that "crossdresser" doesn't sit well anymore and you've used "trans" a few times. That shift in language often reflects a shift in understanding. You don't have to have it figured out right now. But pay attention to what feels true when you say it. The words we reach for often know something before we do.

On what you're really hoping for: You said your motivation is that "maybe she will love the real me and say to heck with it — come out the closet and live your truth." That's not a small hope. That's the hope. And here's the thing — she's already moving in that direction. She may not be ready to say those words yet, but her actions are speaking. Listen to them.

You said you're "dying inside" while acting cool. Stop acting cool. Tell her you're scared. Tell her this means everything to you. Tell her you're grateful and overwhelmed and terrified all at once. Let her see what this is actually costing you emotionally. That vulnerability is what builds real intimacy — not the performance of having it all together.

You've been waiting 30 years for this door to open. It's open now. Walk through it scared if you have to. But walk through it.

The solo cruise is your practice run. The girls' trip is your real chance. And your wife is already more ready than you thought she'd ever be.

Don't let fear talk you out of the thing you've wanted your whole life.

With love!
— Susan 💜

[Jillian-TG]

First, let me say this clearly: what you're describing isn't a problem. It's a breakthrough!

Your wife — after 30 years of "tolerating" your feminine side — just handed you a bikini and started casually discussing pool outfits. She agreed to a full girls' trip where you present 24/7. She's not drawing hard lines. She's opening doors.

And you're terrified. That makes complete sense.

Here's what I think is happening: you've spent three decades managing expectations, negotiating for crumbs, and protecting yourself from disappointment. You learned to want small things because small things felt survivable. Now something big is actually possible, and your nervous system doesn't know what to do with it.

The fear you're feeling isn't a sign that something is wrong. It's a sign that something real is at stake. You're not scared of failing. You're scared of succeeding — and what that might mean for the rest of your life.

Let me address a few things:

On passing: You said you "definitely do not pass but look ok in female mode." Here's the truth — on a cruise ship, people are on vacation. They're relaxed, they're drinking, they're focused on their own good time. Most won't look twice. The ones who do notice will mostly mind their own business. And the handful who might have opinions? You'll never see them again. A cruise is actually one of the safest places to test extended presentation because it's a contained environment with a built-in exit date.

On the solo cruise first: This is smart. Use it. Test everything — the restaurants, the pool, the face-to-face interactions you're worried about. Figure out what works, what needs adjusting, what you're comfortable with. By the time the girls' trip happens, you'll have real experience to draw on, not just fear.

On your wife: She's not just tolerating anymore. She's participating. She bought you a bikini. She's discussing outfits. She agreed to 24/7. That's not a woman who's holding her nose and enduring something unpleasant. That's a woman who's genuinely trying to meet you where you are. Don't underestimate what she's offering.

On the label question: You mentioned that "crossdresser" doesn't sit well anymore and you've used "trans" a few times. That shift in language often reflects a shift in understanding. You don't have to have it figured out right now. But pay attention to what feels true when you say it. The words we reach for often know something before we do.

On what you're really hoping for: You said your motivation is that "maybe she will love the real me and say to heck with it — come out the closet and live your truth." That's not a small hope. That's the hope. And here's the thing — she's already moving in that direction. She may not be ready to say those words yet, but her actions are speaking. Listen to them.

You said you're "dying inside" while acting cool. Stop acting cool. Tell her you're scared. Tell her this means everything to you. Tell her you're grateful and overwhelmed and terrified all at once. Let her see what this is actually costing you emotionally. That vulnerability is what builds real intimacy — not the performance of having it all together.

You've been waiting 30 years for this door to open. It's open now. Walk through it scared if you have to. But walk through it.

The solo cruise is your practice run. The girls' trip is your real chance. And your wife is already more ready than you thought she'd ever be.

Don't let fear talk you out of the thing you've wanted your whole life.

With love!
— Susan 💜

Wow! Thank you so much for such amazing advice. I will read your post again to make sure I digest everything because you nailed it. Really - thank you.