A Crossdressing Journey: Adjusting to Retirement

[Paula_56]

Hello everyone,

I've been coming to this site for a long time?I think I signed up back in 2009. What a ride it's been!

I had some really great times as a crossdresser, mostly during my 50s and into my early 60s. I traveled extensively for business, which allowed me to go out dressed in many different countries: Canada, the US, the UK, and Australia. I even hit almost every major city in the US dressed as a woman.

I went to therapy, talked to my therapist, and was able to get a lot of things out on the table and truly accept myself.

Then, COVID hit. My wife and I retired up to the deep woods of Maine. We've always had a "don't ask, don't tell" policy, and she knows I have women's clothes in my closet in my own office.

The trouble is, without the privacy to truly enjoy myself, I seldom dress up anymore. Going out and about?that's a thing of the past. Business trips were what I really loved because they allowed me to do that. My wife isn't supportive of me going to conferences or anything similar now.

So, I was just wondering, as you get into your later years (I'm about to turn 67), how did your cross-dressing habits change? How did you adjust to retirement?

I know there is a lot of experience and well-learned advice here, so I'm looking forward to your responses. I'll post a picture of me just for the heck of it?that always seems to get people's attention!

Big hugs, Your sister, Paula

[Joanie CD]

It is a real shame that you can't do something you've enjoyed for a long time. Of course it's important to keep a good relationship with your spouse. Maybe you could take some inexpensive mini-vacations where you can be Paula for a couple of days, without your wife having to be involved. You could go to a small town (or city) not too far away, find a cheap hotel, and have fun. I don't know your situation -- maybe this wouldn't work, but it really seems unfair that you can't do your hobby/true self/obsession, especially now that you have more time on your hands. I hope you can work out a good compromise for yourself and your wife.

[TheHiddenMe]

My wife knows I dress, and I'm retired. I started going out after I retired.

Perhaps my wife's and my relationship is different, but I don't own her and she doesn't own me. She can decide to do things--like stay extra time in Australia--and I can decide to do things--like going out dressed. I try to have enough positive qualities to offset the idea that she doesn't like me going out dressed.

The side benefit to me of her extra time is Australia is my freedom to dress more often when she is gone, although we have an adult son living with us so the opportunities are not unlimited.

I joined the St. Louis Gender Foundation so I could point to a meeting and say "I'm going" so that gave me opportunities to do out dressed (and there were times when I dressed without telling her, less so these days). That gives me two times a month to have a reason to go out. Other times I just tell her I'm going out, like Halloween. I will also go to concerts solo and don't tell her specifically I am planning to dress but if she asks I'll answer honestly. I went to Dee-Va Las Vegas and didn't ask for permission, I just told her I was going.

None of us know your relationship with your wife. But I don't feel I need to ask permission from my wife, much like she doesn't need permission from me to do things. It's how we have managed to survive a long distance relationship and 33 years of marriage. They are not easy conversations to be had, but telling your wife I want to go out of town for a weekend and making it clear without saying it what you are planning to do ought to be doable if your marriage is strong enough.

Just my two cents.

[krissy]

Hi im 68 my wife and i are still married 45 years but when it come to me dressing she is dadt,she knows i dress but now im home every day. i dont get to dress too so if she goes to her moms to help her i get 1 hour its not enough.lol i miss driving around cant see at night sucks. by the way you look Great when dressed .i just try to dress as much as i can and dress up some in bed i sleep in my own room we move too much to sleep together im not going any wheres just try to enjoy every minutes i know i do

[docrobbysherry]

Because you r so passable, Paula! At least in appearance!

Retirement gives me more time and energy for Sherry. Since I'm long divorced I have no idea how u should proceed with your non-accepting SO.

[Aka_Donna]

Youtube music videos, artist queen. There's a song where Freddie is wearing almost a Madonna cone bra and dancing up and down a staircase singing "I've got to be free". This might be a way to restart a discussion about dressing. My wife always comments on this scene: "there's Donna". The key here is to see if somehow youall can find a new agreement on what works for you. Ours has changed over the years and the key is her thinking well that just's him, but it's a good relationship. We don't know/remember what her concern was but perhaps if you shared it, someone might offer some insight on how to discuss this aspect with her.

[Helen_Highwater]

Paula,

I've been retired for over a decade and I must admit the prospect of both of us being at home all the time had me worrying that my dressing days were all but over. It turned out not to be the case.

We both have lives to lead. My SO goes out most days to fitness classes so I get a few hours Home Alone Time or HAT as I call it and while I can't fully dress I am to be found in hose, skirt, knickers, bra, forms and a top, heels or boots.

And like you, I'm in a DADT situation. Here's a typical day for me:

My SO uses a ventilator at night due to sleep apnea. The noise from the machine plus she's a duvet thief, is happy sleeping under the thinnest of duvets in the coldest of weathers means I sleep in a different room. So I get up and put on femme clothing, go downstairs, tidy the kitchen from last nights use, make my SO a breakfast tray, cover up and take her the tray. Then downstairs and back into femme attire, My SO will sit in bed doing puzzles, knitting, messaging the kids while I sit in the living room on my tablet doing daily puzzles and social media.

When it's time for her to go out I cover up and once HAT starts then back to femme. Before she gets home I cover up (CU). We make lunch, she sits watching TV, I retreat to my old home office and once again go femme. At some point I'll go drab to get those annoying chores done but after the evening meal I shower, and you guessed it, back to femme and time on the PC in the office. She goes to bed before me so I get yet more femme dressing time. As I say, I'm in a DADT relationship and she knows that I'm likely to be in femme clothing and acts accordingly

My out and about time is severely restricted apart from the odd times she might be away for a few days or I book an annual solo week away and go femme 24/7. That said I know that I'm fortunate to get so much time enfemme. I kept a spreadsheet of my dressing noting time with or without forms while dressed. Over a 2 week period I averaged 8.5 hours a day in femme attire and the with forms on by a margin of 3/1.

I guess the point I'm making is you never know just how things will turn out and how circumstance can deliver things in your favour.

[kimdl93]

Hi Paula,

I have followed and to some extent emulated your style and activities over the years, but I reached the retirement milestone and then failed at retirement a few years ago. After Jan 1, I will give it another shot!

My semi-retirement has been a bit less complicated than most, because I have been divorced for over a decade. Needless to say, I enjoy considerably fewer constraints on my habits than anyone with a less than supportive partner. That also means I haven?t much to offer in the way of advice. I hope that you and your wife can reach find some level of accommodation. Its a darn shame for such a lovely woman to be hidden away.

[missjoann49]

Hi Paula, I haven't been here in a while but do remember following you in the past and we had some conversations as well. You have always presented yourself as a beautiful woman. I wish I had an answer for your problem as I know how much dressing mas meant to you. All I can say at this point is I wish you the best and hope that something works out for you

[PaulaJeanette]

Hello Paula, like missjoann49, this paula recalls your presence on this site. You presented yourself as a model for many of us who enjoy this lifestyle. With regard to retirement, since I retired before my wife (she is 4 years younger), retirement gave PaulaJeanette more alone time. As a result, PaulaJeanette enjoyed femme time to the max, especially during the work week. However, those glory days came to an end 3 years ago when wife also retired. Now, the only femme time for PaulaJeanette is sparse and few between when wife leaves home.

I totally understand what you are reminiscing related to business and work travel. PaulaJeanette also indulged when in her hotels rooms across the country but never ventured out. One particular trip was to Las Vegas when PaulaJeanette stood in-front of the room window on the 23rd floor facing the Vegas Strip. With curtains wide open and wearing her lingerie with a flowing negligee, it was a thrill wondering if anyone saw or noticed the woman standing at the window.

So, my advice is to enjoy the opportunities when they arise. And, welcome back...hugs!

[JocelynJames]

This thread has a lot of insight, as I hope to retire in 3 years at 59 1/2. . I don?t go out much, but set that as one of my goals, but realize unless I?m actually going out to ?do things?, it may get old fast. I should be practicing and finding those hobbies now!

[JesseVF]

Wife and I now both retired for about a year. Luckily after I came out to her a few years ago she developed the attitude of it?s my house too so I can do what I want in it. I dress most evenings except wig and at times during the day also. Going out of the house was more dadt so that happens less now in retirement. I hope you can come to some kind of understanding with her that meets your needs.

[Elizabeth G]

Hi Paula,

I understand your situation. My wife just recently retired and I am planning to do so at the end of 2026. My wife learned of my crossdressing some years into our marriage. I am one of the lucky ones. I did not end up in a DADT situation (as a matter of fact, she attended her (last) company Christmas party today wearing one of my tops!). This does NOT mean that she is totally accepting or supportive, but somewhere between DADT and supportive.

We haven't worked out any details yet, but since my wife prefers not to see me presenting female (though she has) in all likelihood, when I retire I expect I will be out and about, presenting female a couple of days per week. This way I get what I need (the chance to express my true self), while she gets what she needs (not having to actively participate or see me dressed).

[SaraLin]

Well Paula, my situation is a bit different and probably won't help much. Here goes anyway.

In my case, my time spent dressed feminine has actually increased.

When my wife and I first got together, I told her everything. I told her that I couldn't give everything up - and wouldn't even try.
If that was going to be a deal breaker, I'd understand and we could go our separate ways.

Well, I guess she thought I was somewhat of a keeper and we worked out a compromise.
Panties were fine. She didn't have to see me in them.
Nighties were OK - as long as they weren't too "girly". Lacy or sheer outfits, baby doll styles, or such things were too much for her and "freaked her out."

Anything more than that she didn't want to see.

I agreed that I could probably live with this. She's worth the compromise.
It's been difficult. I always want to do more, but I keep the majority of my Sara-ness away from her eyes.

Now comes the part where I dress more, lot less, after retiring...

I no longer have to jump out of bed, put on pants and rush off to work.
I can lounge around the house in my nighties until late morning. She doesn't object to this, and occasionally, I'll even "stay comfy" all day.

[Jillcder]

First of all I have to say I just love your black skirt suit you so feminine and 100% pass! The dreaded retirement for us crossdressers is very frustrating on one hand we get to enjoy our new freedom but our Crossdressing time takes a hit i also traveled for work allowing me to dress on many overnight trips but lost that dressing opportunity after retiring so frustrating.
I agree this forum has many great ladies with lots of experience I look forward to hearing how others deal with this.

[Stephanie47]

For me, retirement was great, at first. I retired at age 60 and my wife continued to work full days several days per week. Then she retired. It has always been "Don't Ask, Don't Tell." When I had those full days it was a day of domestic chores. On occasion she would visit our daughter out of state which gave me 24/7 times and time to go out for evening drives that always ended up with a stroll in a safe neighborhood of homes and shops. We sleep apart for medical issues and comfort, a lot of tossing and turning due to pain issues for both of us. I have the opportunity to sleep en femme in a nightgown with a full slip, bra and panty. Maybe, she knows I sleep en femme, but she has never said anything about it. I have been retired for 17 years now. Coming to this site and another particular one keeps my head in the game. All I can say is, if you're in a DADT marriage, it's going to be rough when your wife also retires.

[NancySue]

Hi Paula, I?m glad to see you back. You look fantastic, as usual. Always enjoyed your posts. My wife and I are both retired. She knows, helps and supports my extra curricular activity. Our retirement actually open up a door for me. That being frequency. I?ve dressed since the get-go, but carefully and discretely, small town and all. Mostly under. Since retirement, I dress pretty much every day. Mostly like your 2nd picture. I still dress mostly male mode when socializing, to eat out, etc. There are very few, if any, days I?m not underdressed, always hose. What a nice way to start each day.

[HollyGreene]

I'm not retired yet - a few years away.
My wife is 9 years younger than me, so when I retire, I'll have a few years of being home alone, 3 or 4 days a week, so I know how my opportunities to get dressed up will change. But I guess that will all come to a halt when she retires.

[Jenn A116]

Hi Paula,
First let me say that it's nice to see you here more frequently. I regularly follow your writings on Femulate.

As to your situation, I've been able to actually improve my femme presentation in retirement. How? By joining a local CD group and going out with them each month. Some outings are just at a secure, private location. But more of them are Girls Night Out events at local restaurants. Through this I've met other CD's and have benefited from their support, as has my SO.

[JulieC]

First off; Paula, you look GREAT!

My wife and I are not retired (~5 years yet). We have discussed crossdressing in retirement though. It's nebulous so far. My wife is accepting and supportive, but somewhere in her there is a limit. We've discussed it, but she's not sure how much is too much. She's pretty certain that me being dressed 100% of the time is a non-starter. But, I've also spent considerable time around her fully crossdressed without any negative repercussions. We discuss the topic from time to time; it's kind of check-in sort of thing. She knows I want very much for her to keep communicating with me on this. I don't want to have her tolerate it, as that will eventually blow up. Our marriage in general is strongly based on wide open communication, so it's very important for both of us to discuss such things. For us, that's the key.

[Paula_56]

Paula,

I've been retired for over a decade and I must admit the prospect of both of us being at home all the time had me worrying that my dressing days were all but over. It turned out not to be the case.

We both have lives to lead. My SO goes out most days to fitness classes so I get a few hours Home Alone Time or HAT as I call it and while I can't fully dress I am to be found in hose, skirt, knickers, bra, forms and a top, heels or boots.

And like you, I'm in a DADT situation. Here's a typical day for me:

My SO uses a ventilator at night due to sleep apnea. The noise from the machine plus she's a duvet thief, is happy sleeping under the thinnest of duvets in the coldest of weathers means I sleep in a different room. So I get up and put on femme clothing, go downstairs, tidy the kitchen from last nights use, make my SO a breakfast tray, cover up and take her the tray. Then downstairs and back into femme attire, My SO will sit in bed doing puzzles, knitting, messaging the kids while I sit in the living room on my tablet doing daily puzzles and social media.

When it's time for her to go out I cover up and once HAT starts then back to femme. Before she gets home I cover up (CU). We make lunch, she sits watching TV, I retreat to my old home office and once again go femme. At some point I'll go drab to get those annoying chores done but after the evening meal I shower, and you guessed it, back to femme and time on the PC in the office. She goes to bed before me so I get yet more femme dressing time. As I say, I'm in a DADT relationship and she knows that I'm likely to be in femme clothing and acts accordingly

My out and about time is severely restricted apart from the odd times she might be away for a few days or I book an annual solo week away and go femme 24/7. That said I know that I'm fortunate to get so much time enfemme. I kept a spreadsheet of my dressing noting time with or without forms while dressed. Over a 2 week period I averaged 8.5 hours a day in femme attire and the with forms on by a margin of 3/1.

I guess the point I'm making is you never know just how things will turn out and how circumstance can deliver things in your favour.

I suspect this is the path I will take as I am kind of doing it now. Did you need to dress change as you got older how was it different

[SIZE=1]- - - Updated - - -[/SIZE]

Hi Paula,
First let me say that it's nice to see you here more frequently. I regularly follow your writings on Femulate.

As to your situation, I've been able to actually improve my femme presentation in retirement. How? By joining a local CD group and going out with them each month. Some outings are just at a secure, private location. But more of them are Girls Night Out events at local restaurants. Through this I've met other CD's and have benefited from their support, as has my SO.

You're lucky my wife would not go for that

[MsEva]

I found time to dress a lot before retirement, and since th 2022 rertirement tjha level has only increased. My DW know that I dress often and she has a lot of social events during the day. She even suggests that I might enjoy dressing while she is out. She also said that I can dress when she is hone but I always decline stating that if we are together that I might postpone that. Retirement has been so helpful I get to spend hours a week dressed. When I dress I like to be productive and do some housework. I do a lot of laundry and cleaning en femme. She is quite appreciative of that.

[CynthiaD]

Since I retired, I get up in the morning and put on a dress. Sometimes I have boy things to do. My male-mode outfit is embroidered jeans and a feminine top. I have moved all my female tops to my male-mode presentations. I get a few odd looks, but I don’t care.

[Fiona_44]

Paula,

I retired somewhat early but spent most of the time caregiving for my sick wife. Unfortunately, she passed away a little over 4 years ago. Fiona emerged around 6 months later. I was always a life-long, closeted crossdresser but circumstances now allow me to live as a trans woman. Funny, the twists and turns one's life can take.

[Monique65]

As others have said, my dressing time has increased since retirement. When we first retired she would volunteer once a week at a local non-profit and I would dress to do the housework. When Covid hit, that stopped. She came to accept my feminine side soon after, and now I wear panties, a bra, leggings and a soft night gown every night.