Gettting Older, Retirement and crosssdressing How do you handle it?

I'm 65 years old and I've been cross-dressing my whole life. If I were to give you a rundown of my life, it would probably sound like so many others here: denial, suppression, acceptance, guilt, purging?all of those things. When I turned 50, I entered what I would call the golden era of my cross-dressing. I traveled on business, accumulated a wardrobe, lost weight, and went out and about in towns all over the United States, Canada, the UK, and even Australia. I was out and about as a woman, doing so many cool things: everything from going to concerts and museums to dining out and meeting friends. It was so much fun.

Now here I am, retired and living in New England with my wife, 65 going on 66. I haven't dressed in a while. I don't have an outlet, and my wife isn't accepting. I'm just wondering how others are handling this period of their life.

Hello Paula.
I will voice my thoughts, Of course you situation may vary.

My wife in the beginning was unaccepting as well. Over a period of time with some discussions.
She became more tolerant. I did not travel at all for work. So the only dressing time I had was when I was home.
I would sneak some time in the middle of the night when everyone was sleeping. When she became a bit more
accepting she would go shopping and take the kids. She would intentionally give me time.
She would always call before she came home so I could change back to guy mode.
Eventually we divorced and I now live alone. So I can dress whenever I like. (This is not for everyone)

I would recommend, If your wife knows, That you talk to her and make some sort of arrangement when you can dress.
Maybe when she goes shopping. or when she is out of the house, That way you will get some time and she will not have to see it.

Just my thoughts.......

Thanks for the advice, I need to get out and about, I miss those days, dressing up at home just doesn't do it for me. I live in a small town in Maine so I really need to get out to a conference or something

It's a difficult time for sure. I was fortunate enough to be able to underdress and to wear androgynous clothes, albeit just jeans & sweatshirts from the womens department. I just lived with it, adding pantyhose & bras on the odd occasion that my wife went out. It wasn't until she passed away 8 years ago, having developed the Big C, that I was able to dress fully. I think I am making up for lost time now, my wardrobe is filling up with my femme clothes and many of my old male clothes have gone to goodwill. I still keep a few bits of male clothing around, for the inevitable final journey, but otherwise, I am dressed every day now, because I can. Still in the closet, so family see me in clothes that resemble who I am supposed to be.

Actually I think I'm at my peak right now, but my backstory is different than most. I did not start crossdressing until I was 69 - three years ago. I fortunately missed the vicious guilt/shame cycle. I have never even considered purging - there is no reason to. I came out to my wife of 40 years about 2 weeks into my active period and she is accepting, supportive - even participatory up to a point. All that has allowed my femme persona to flourish and I have enjoyed going out, meeting and making friends, and going to CD/TG events. Lots of things I'm looking forward to as well, including developing my presentation to the best of my ability. I also do not regret missing out on my younger years - I'm having way to much fun now, and I find the whole experience quite "youthening".

I realize I'm one of the lucky ones, but I use my example to indicate that just because one is older I does not necessarily mean that all l is lost. For me, the best is yet to come!

"How are I handling it?"

Not well. My wife is not accepting, although she does not make snide remarks about it or search the house for my wardrobe. I retired when I was sixty with my wife still working at least several days a week. I have always felt more comfortable being an in-home cross dresser, so those full days were spent doing domestic chores, a la June Cleaver, 1950's look in dress, heels and hosiery and all the proper undergarments. On occasion my wife visited our daughter who was living in the mid-west. That afforded me up to ten 24/7 hour days. Then my wife retired and our daughter moved home; 35 miles away. Gone is alone time; June Cleaver, Harriet Nelson time. There have been several over night stays for my wife to stay over at our daughter's apartment. I would love to be able to be en femme for a prolonged period of time. For me, it's all or nothing. I am long past grabbing at some "crumbs of time," when she is out for several hours. We sleep apart of health/medical reasons which enable me to sleep in a nightgown with a bra and panty, and perhaps a full slip under the nightgown. She is a late riser in the morning so, like today, I can peck away on the keyboard still wearing my night clothes. It is better than nothing. Don't suggest a plan to chip away at her non-acceptance. "If I wanted to be married to a woman, I would have married a woman!" she has said. She has personal factors that engrain that position into her being that I understand and respect.

Retirement was the opposite for me.
I dress almost daily, we go out frequently and it's become the most natural thing, which is what I've always wanted.
Covid was the big push and that meant nearly full time for those 2 years.

Great topic. I retired 3-4 years ago. My wife still works part time. I currently enjoy more freedom to dress than I ever have. We are DADT, my wife knows when I dress, but I do not dress when she is home. What will happen once she retires fully, time will tell.

Paula, I am also in New England and, at 74, have been retired for 10 years now.

I am afraid a lot of this depends on your wife. In that 10 years of retirement, I lost my late wife to cancer, lived single for a few years and and have recently remarried. This sequence of experiences wave left me cognizant of just how much our personal relationships shape our personal expression and behavior. Not just cross dressing, but especially cross dressing.

My first wife knew I was a cross dresser before we married. Her acceptance and support was all over the map over the years. I loved her and respected her limits. She was fine with me going to Tiffany Club meetings and, in later years, dressing around the house, but she drew the line at going out in the general public. Mostly out of concern for my safety. She had permission to, and did, talk over our situation with her close friends.

After she passed, single again, I realized that untangling my personal issues, mainly gender dysphoria, ADHD, and sleep apnea, all of which have overlapping effects, was the most important issue in my life, overriding my bucket list. I started talking on the phone with friends from this site, got my ears pierced, went out in public dressed in daytime for the first times in many years. I started going to Fantasia fair. I was still , however, leading a double life.

The most bold thing I did, perhaps, was to bring in a housemate. I didn't advertise, but responded to ads looking for housing frankly and honestly. It took a lot of patience, but I did get responses and eventually a housemate, who I got along well with, from the start. So well that we got married a few months ago. She is a longtime supporter of the LGBT+ community, mother of a lesbian daughter, a licensed cosmetologist, and she likes to play dress up. I love her to pieces.

At this point I have come to realize that the only limits I have are ones in my own head. She has helped me overcome barriers that I couldn't get past on my own.

So I guess my advice to you would be; work something out with your wife!

It's great to know I'm in my golden era. I'll make sure I do everything I can before I turn sixty. Lol i'm sure you've heard of first event in boston. I don't know what version of it exists these days. Kept changing locations, and then they moved to the city, and I gave up. Driving and parking would be a hassle. That one was a staple for me for quite a while. If you're up for a little travel, there's keystone, guess where in pennsylvania bit of a trek, but if that's what you need to get out, it's there, I think it's february or march, look it up. There is triangles well friends of triangles now because triangles closed that was the bar in Connecticut. I know. It sounds like you're done with the club thing, but it's available. Just not all the time anymore used to be once a month.Now it's a few times a year. Not the same, but it can be a good crowd. I'm looking forward to retirement in a few years, so don't tell me it gets bad. I'd rather be bored and make stuff to do.Than be too busy to have time to do stuff.

I am also not far away from retirement and I am facing the same situation.

At the end of the day, I guess it is completely dependent on the level of acceptance from your wife. If it is near zero like mine, there are few options after retirement , at least for me, and that is kind of depressing really.

Hopefully you will find some path to compromise.

Sandi

@Sandi Beech

Do you have a plan though? I'm just hoping things will work themselves out.

Well, my wife and I parted ways.

Fully retired since covid. The usual morning private time before work just became the usual early morning private time until about 10:00.
Strict DADT and she doesn't pry or snoop. Too old for all that drama.

Paula, I fear that I will be in the same situation in a few years. I am not in a DADT but me dolling up 2 to 3 times a week with her home is going to be an issue.

I think a real serious conversation needs to happen in your life.

Nine years into retirement! The first few years were horrid from a dressing perspective. After decades of dressing mainly in business trips and locally. But my wife?s heart condition and my prostate issues have forced us to sleep apart. I sleep downstairs and she stays upstairs. Any it has worked great for dressing, at least from 10pm to 7am I can dress all I want and she has not interfered or even ventured downstairs in that time. I am Uber happy that we have found something that works for both of use though she still does not talk about it. Fine.

I believe Jane G got it right, you need a plan. I was able to retire last year at age sixty. I was so convinced to do it and when the day came my wife asked me what I was planning on doing with all my time. I really had no answer, I just thought I would do nothing. It so sad that we pray for it all our lives and then when it comes we are caught lifted footed. For yourself you probably couldn't wait to retire and now you miss the business trips and probably didn't calculate how it would effect you dressing time. I'm on board with everyone else that a talk with your wife may be in order. Good Luck and let us know what you decide.

My life has been quite different. I didn't cross dress at all when I was 50 and married. My wife threatened to divorce me every time we got in a verbal fight and I ended up divorcing her after a short marriage.

Now I'm 71, semi-retired, single and have quite a bit of time to CD. But I still don't get out as much as you did when you were 50 and traveling. I've been going to CD support meetings for the last 14 years, 50 miles from home. Small town in Maine has to make it hard to get out...

Well, Paula, when I was your age I was just beginning to go out dressed. Attended big T events around the country. I still attend one or two every year and smaller local events every month. And, maybe dress in one foreign country every year, too.:battingeyelashes:

As far as retiring? I'm only 81 so I'm not ready for that yet. No idea what that's like? But, working for myself means I can take off when I want to!:thumbsup:

Not bad for a closet dresser, huh?:heehee:

well Paula, depends on where you think you are in the cycle of life, Im a healthy 66 and enjoying dressing and going out with m wifes concent , she doesn't come with me, but yes I insist I dress , told her what I am from day one before we got married. I reckon I have a good 10 years of amazing dressing and going out with friends to come, I travel the whole of the uk shopping , meeting peeps like us, Helen Highwater on this forum extends her amazing yearly offer to take us out into Manchester usually in November , but this year has been cancelled, but will be in March next year, but my thoughts on this, do you want to really sit back in your chair thinking I should have done this I should have done that ?, I dont I do it !!!!, No regrets !! just amazing memories, so when I do eventually sit back in my chair, I can smile and remember, morbid thoughts, do you think your going to die and come back for a second chance ?, nar grasp life by the hand enjoy your senior years, I AM Rant over love Debs

Retirement just means I don’t get paid for the work I currently do. It also means I don’t have nearly the opportunities to dress that I used to have. My wife is not happy with her husband’s feminine side. That said, I have been able to incorporate a few items from the other side of the aisle into my daily wardrobe, but none of them are cute nor even remotely girlish.

My background is in the natural sciences and so have had a few times where I have been able to take a weeklong class or seminar as Christie. Most everyone has been incredibly accepting and welcoming except for that one guy. This has kept the dysphoria away.

Are there places your wife likes to travel?

Send her.

Paula, that picture brings back so many good memories of Crossdressing in hotels on my overnight business trips. I also retired a few years ago at 61 and yes it definitely cut into my dressing opportunities but the urge continues I do not know if my wife is accepting or not I just can not find the courage to have the talk so I sneak in every opportunity when she is out of the house. Retirement is great I just need to figure out how to incorporate more dressing. Good luck

My past is very much like yours. I?ve followed and admired your posts and pictures. You?re quite attractive with excellent taste in ensembles. The big difference is I?m so fortunate to have an accepting, supportive wife. Before retirement, I often underdressed through the week with more on weekends. Now retired, I?m free to dress as I please, whenever I please and I do. Its wonderful. Is there any way you and your wife can reach some sort of compromise? Hopefully so. I fear denial will let the pink fog in and cause some anxiety. I?m wishing you the best.

So so so true

For me retirement has been awesome for my dressing. My wife has been retired for seven years, me for two. She has so many things she on her schedule that i get to dress many times a week. I so love that. She is very supportive and tries to give me time to dress. I try not to take advantage of it and dress when it is convenient. I don't want to be too overbearing but I dress several times a week and love it. Can't say enought how retirement has been so wonderful.

This is a very timely thread for me, as my wife and i both took early retirement in the last few weeks.
Fortunately she is accepting and encouraging so it will not change anything in the balance of home life. We go out as ourselves when we wish.
I hope that you will all find a good balance in your own retirement. :thumbup:

I agree with Nancy Sue. You two need to make adjustments for the good of your individual needs in this more recent and revised world. That may require finding a good counselor who can work with the two of you. She can help your wife see that total resistance is not an option and to recognize you have some unusual needs that cannot just be put on the back shelf and forgotten about. But also to help you see her position of not being comfortable with a mate that is a mixture of the male-like and the female-like when it comes to gender. You are each who you are, but there are many compromise positions where you can share a bit by altering your expectations to accept your differences that were there long ago, but were not apparent when together. She probably has some hurt, like my wife was, to discover that her man was also a bit of a girlfriend. We have been retired for many years now as we are each close to 80 and I don't fully dress anymore. But I always include something in my attire that carries an androgynous message. I have learned to be satisfied with that and she has learned to not only accept it but to support it. Not perfect, but we will soon have our 56th anniversary and we are still very much in love with each other. There is no sex anymore, but there is a lot of cuddling and we can talk and share most anything. I'm happy; she's happy; but it is not my perfect or her perfect.

I was fortunate to work from home for many years so had a lot of time to dress. I retired a year or so before my wife so again home alone time. When the SO retired I to wondered if all my dressing time was ended but it turned out not to be the case. We have our different interests, my SO going to exercise classes 4 days a week as well as out shopping and off to see her mom and sister.

So while not ideal, full on dressing difficult, I did find myself with several hours most days were I could at least put on a skirt, top, forms etc and spend some time dressed. And of course, I engineered an annual weeks walking holiday that allowed me to be enfemme 24/7. Things have a way of sorting themselves out. You may find yourself having to adjust your mode of dressing, going all in, makeup etc not being possible but you quickly learn to be grateful for those opportunities to be "casually" dressed and make the most of them.

I didn't know how far up in Maine you are, but there is an event in Marlborough Massachusetts in early January.
https://www.eventbrite.com/e/diva-so...dssbdestsearch

I wish I could say I was precisely in the same shoes as you Paula, so perhaps I could offer some more insightful advice. The only thing that I can think of is; you are who you are. Your wife fell in love with a man who is a crossdresser. It's not like she fell in love with all of you except being a crossdresser. It's part of you, whether you're dressed or not. It's part of what makes you tick, part of what makes you...you. So, she's not accepting but really...she's in love with the man who is a crossdresser, like it or not that's the reality. I think being a crossdresser brings positive things to the table that the non-crossdressing male just can't bring. Another way to view this is that it is important for a crossdresser to dress. Repressing it comes with a host of problems. Ok fine, your wife doesn't accept. Does that mean she has to control every second of your life to prevent you from crossdressing? If that's the case (as it is for some of us here, unfortunately) then I have no answers. If she only doesn't want to see it, but is aware of it, then perhaps some detente can happen as noted by others above in this thread.

Since you asked how others are handling this time period; I'm not retired just yet, but my wife and I get a ~6 month sample of being empty nesters recently. We talked before it happened, and I noted that I would likely prefer to be dressed 100% of the time when I could, at least initially. She was fine with that, and we made sure to touch base frequently to make sure things were and that it wasn't too much. As expected, once the time came, I was soooooo ready to be dressed 100% of the time when we were at home and I did. As soon as I got home, I would change. She was good with all of it. It was a watershed time for me; finally, after repression in one form or another my entire life, the feminine me was able to be an equal partner. I've never gotten her back into the pandora's box since we stopped being temporary empty nesters :) Anyway, after a month or so, the edge on the desire to dress all the time faded some; I achieved a balance somewhere around dressing 60-70% of the time we were home. I expect this will probably be the norm when we do retire.

Like others here, my wife and I sleep apart for health reasons (mainly having to do with my great difficulties in getting healthy, undisturbed sleep). My main outlet for crossdressing now is that I sleep in nightgowns, bra, forms, and pantyhose every night. It is a wonderful feeling, and I look forward to it every day.

Hi Paula. I am the same age as you. I have been retired for a number of years. When I want to go out I go to a city about an hour away. I pack my bag when my wife is out (not accepting as well) and put it in the car or garage when she is asleep. Sure I would like to dress more often but I seem to find some limited time when she is out visiting or doing an activity.

Hi Paula :hugs:, I am 82 and my:love:Wife of lmost 61 years we have a very workable DA/DT,

I can dress anytime that I want and Still wear my 4 & 5 " heels,

I so much my Dressing time, I don't go out dressed, >Orchid**O:daydreaming:O**

Very relevant and profound topic.
I'm retired, in my 60s, been a serious crossdressers for decades.
The profound joy and need to crossdress continues to accelerate as the years pass, for reasons I don't totally understand.
I told my wife before we were married, have had years of DADT, occasional discussions and told her I wanted to crossdress everyday while retired.
She wasn't too thrilled with that so we're somewhat DADT again, which I find confusing and stressful.
I hate to keep my crossdressing secret but in some ways it's the best approach.
My wife "accepts" and tells me to do what ever I want and need to do.
But being fully crossdressed when she's home and stressed is not optimal.
So, no easy answers, it's complicated...

Quote:

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Originally Posted by Paula_56

I live in a small town in Maine so I really need to get out to a conference or something

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I suggest that you check out First Event in Boston beginning January 29. I haven't been there but based on a friend's report, it very similar to Keystone, of which I'm an over 10 year veteran.

I just turned 60 this past November and I am getting close to retirement. Also, I will have more chances to crossdress.

Hi Paula, both of us are running in parallel paths, but I am ten years ahead of you. My offer for you right now is to find the right moment to work with your wife to find a solution. Our desires to explore the world of femininity are strong and we really can't suppress it. I don't know how far up in Maine you be ( being from NH, I am very familiar with ME) but maybe I can help with getting the chance to adventure out as Paula.

Two other writers made suggestions of opportunities in Massachusetts. They are the Diva Social in Marlborough MA on 1/10 & 1/11 and also First Event in Boston through the last week of January into February 1st and 2nd. I would be glad to describe them in more detail if you think that you might want to venture forth. From your photo, you would definitely fit right in!!! Personally I will be at the Social for the weekend and hopefully, I can do a day trip to FE just to meet with friends for a day. Over the years especially since retiring, I was lucky to gradually convince my wife that adventures away such as these were just what Sarah needed.

Hi Paula,
I am a few years older and I have never told my wife. She continued to work for a couple of years after I retired and that provided me with an opportunity ot dress. But when she retired, we made some moves which necessitated a fair.y major purge. As a result, my stash has trimmed down to a small collection of undies. And because I now get very little ?me? time, I simply look forward to and enjoy the few hours that I get from time to time. To be fair though, she keeps me busy so it?s not as if I have a lot of time to think about dressing and the urge is not as compelling as it was years ago. Just part of life I guess

When my wife and I retired ten years ago, she volunteered at a local non profit one day a week. This gave me ample time to dress and spend the day en femme. When Covid hit, she stopped the volunteer work so I began wearing panties full time, knowing she would find out. When she did, she asked why and I said I liked the way they fit. This opened the door a crack and began the conversation. She suggested that I get some panties of my own, and even helped me pick them out. Slowly, over time, this progressed to sport bras, leggings, and night gowns, all of which I wear regularly. I am content with this arrangement and have no desire to take it any further. My point is, go slow, be honest, and show her that you appreciate her acceptance. Hopefully, your wife will come to accept you as you are, like mine did.