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@sondra
@skippy1965
Good morning Cynthia, I have been playing around with cross dress sense my teens. You know mom’s panties and girdles when they were gone. The wife’s on my free days. To being single and having my own. The internet has made it easier to buy things and explore more. I have purged a few time. My issue now.
The lady I currently am in a […] View
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Sondra wrote a new post 2 years ago
Hello Girls, I got the biggest surprise on a recent vacation. A little over a year ago my girlfriend asked me to stop cross-dressing if I wanted to stay in a relationship with her. She had wanted this in our
I could only dream of a vacation like that.
Xoxo
We can still do similar…only very privately.
Good Morning Sondra,
My wife and I started dating 33 years ago because of my cross dressing. We started out as coworkers and became friends. I opened up to her about my cross dressing after about a year of being friends. My wife asked if I would consider dressing up for her. I invited her to my house for dinner. I modeled lingerie, dresses, and all kinds of different clothing that night.
My wife has always been supportive of my cross dressing. I under dress everyday. I have not worn men’s underclothes in over 30 years. I am still a closet and only dress up at home with the exception of Halloween.
Birthdays, Christmas, and our anniversary ,y wife always buys me either lingerie, a dress or a blouse and skirt. My 50th birthday I even got to go to David’s Bridal and try on and buy a Wedding Dress. It was a true pleasure spending 2 hours at David’s Bridal. A birthday I will never forget.
Love and (((HUGS))) to you Sondra
Dorothy
Xoxo
Wow! You are one lucky girl.
Xoxo
Very pleased for you
Liz
Xoxo
You certainly have quite the lady there. Most wives would have thought you had given it up for good, but she seems to recognize your need. Vacations now will be all the more special by the sounds of that!
I am one of the fortunate ones whose wife is extremely supportive of my dressing, and we do out together with me dressed up.
I never hid this from her, and she was always alright with my dressing but it wasn’t until a few years ago my dressing took on new dimension. I finally gave into the decades long desire to fully dress up and go out, this disconcerted her for a bit, but once she understood I wasn’t going anywhere in our relationship, it brought us closer together.
She puts no real limits on my dressing, but I do limit myself as I know she doesn’t want to see me dressed every day, so I don’t!
Thank you for your great article!
Im going to try to answer all three of your questions.
Mixed messages -Yes of course after the initial shock of finding my secret we would get dressed together and have some wine talking and I thought enjoying, after a couple months sadly my love broke down saying she couldn’t continue in a relationship like this so i completely purge. Sometime after that I came home to a cute sweater dress (black and red in one of my photos) on the bed and she explained she loved me to much to keep me from something i enjoy so much but i still feel she is not totally excepting of Connie so I keep it to a minimum.
Limitations- She doesn’t put any limits on my dressing and encourages my fetish on heals and under dressings I think she prefers i didnt totally shave and love being smooth.
Being positive- she has told me that when i have the time and ability to enjoy being a little more fem i also become and more loving and understanding person. I know she would like a combination of both.
Very different from any experience I’ve ever had…thx.
I would be so happy to have that vacation! What a dream!
Fantastic!
“Have you gotten mixed messages from your wife or significant other pertaining to your thrill of cross dressing?” Geez, Sondra, it’s like every day. She changes like the wind. One day, she can be very encouraging. The next, she’ll say that she hates me (as Dawn) & wants me out of our lives.
I have a similar story. I guess it was about 15 years ago that we went away, for the weekend, to the beach. Almost as soon as we checked in, she pulls a red, silk & lace, baby doll nightie out of the suitcase & said “This is for you.” I asked, “You want me to wear this?” As soon as I did, she was all over me. Keep in mind that she’s known about my dressing since shortly after we were married. She accepted, but was never a fan of it.
She’d tell you that we’ve had some of our best “bedroom adventures” when she’s allowed me to be me, but as of about a year ago, she will no longer allow me in her & her husband’s bed.
Anyway, we have a nail salon appointment, on Saturday (not our first time getting mani-pedis, together). Now, she says she has no interest in going unless I go in male mode. I told her that that would look ridiculous. Besides, I can be somewhat incognito as me. She says she’ll think about it.
The following Saturday, she’s agreed to go with me to a Christmas party where I will present as myself. She’s cool with that. I just can’t figure her out. I think she loves me so much & wants me to be happy, but is afraid that if she gives me too much approval, I’ll keep wanting more.
Sounds like fun Sondra!
My wife has always encouraged me to wear girl things. Her one rule is that we keep it fun. She likes to pick out my outfits, I never know if I will be a boy or a girl for the day until I step out of the shower and see what she has laid out for me. I am M/F about 60/40% of the time. When we go away on vacation, she packs only girl things for me
What a fun turn! With her in control, you get to experience anticipation when you know a vacation is coming up and the fun of being girlfriends when you get there! Acceptance is something we all crave. Beyond that, her participation is a huge bonus! Let us know how it goes from here please.
Great thoughtful article, Sondra!!!
Vacations with you dressed the whole time…? Ah, have you gone to pink heaven…? Wonderful! So happy for you!
To answer your question, this is my second marriage (12 blissful years now!)- (During my first marriage of thirty years I was completely in the closet for many reasons, some real, and some just fear. Sadly, my first wife didn’t know. In hindsight she probably would have been accepting. But I just could not get my self to tell her; probably because at that time I wasn’t really accepting of my CD myself, I suppose.) and my wife knew of my CD before we tied the knot. She is very supportive, as well as her best friend. I’ve been out to dinner, shows and movies with my wife, as well as a few friends joining us a few times. The only issue is that while I’m out to our kids, a few relatives, neighbors, and a few good evolved friends, I’m not “out” to the community. Since my wife knows so many people in the area, most who don’t know, she is nervous being out with me as Jules. And I understand that and don’t push the issue. I’m General if we go out as girlfriends we go out of the local area of town. We share clothes, shoes, and accessories. And she often asks me for makeup and outfit advice, which I love to give.
On vacation by ourselves I often pack a small Jules suitcase. The most fun was a couple of days in Vegas together where we went to shows and dinner as girlfriends. We both enjoyed our time immensely, and talk of doing it again!
So, I am very blessed as well, and so grateful to have my wife’s understanding, support, and love. She loves ALL of me…
Hugs
Jules
So glad to hear of experience for you. I am very fortunate to have a spouse who fully accepts Winter and has even assisted me with makeup hair etc. I see this as a good starting point for you lovebirds. Do not push her, let it evolve naturally and it may come to a point where she is accepting of Sandra and even a regular friend for shopping or Girls night out.
Good Luck with her
Winter
Hi Sondra,
Your Girlfriend needs to understand this is not something you can turn oon and off like a faucet, at least not for me.
I am glad she is coming around I hope.
My wife started out supportive, even buying me my first pair of pumps.
However since seeing me have feminine mannerisms something has happened and she is barely tolerant.
It got fairly serious and we had a serious talk.
I had to tell her I couldnt stop if I wanted.
we still love each other but it has killed out intimacy. I do dress at home though she doesn’t want me dressing locally.
I hope your girlfriend comes around but if not I would make sure you can live without your feminine side.
I know I can’t
Huggs Patty
Hi Sondra,
My first thought on reading your article was- PERMANENT VACATION! – relaxing en femme with your SO is the definition of Dream Vacation.
That said, does my SO send mixed signals? oh yeah, like a Texas Twister.
She knows and has known for over a year when i took her to dinner dressed head to toe in a smart women’s business suit. Since then it’s been fairly casual between us. She’s seen me in various states of dress without any comment. Then on Thanksgiving my daughter came to visit and they were folding laundry and my wife gave her a pair of my panties. My daughter held them up and said they weren’t hers and my wife said they weren’t hers either and maybe they were mine.
And she knew they were. She’d done it on purpose. She pretty much confirmed that latter when i said i couldn’t figure out how a pair of my panties got mixed up with her stuff. She laughed and said the look on our faces was great and next time she’d have her camera ready. It didn’t bother me so much but a very awkward moment for my daughter who, until then, had no idea. So maybe it bothers her more than she let s on.
So how does your SO feel about ‘stay -cations’?c
-joanne
Well, I first started to dress up in my mother’s lingerie when I was very young and fought with being a male and trying to suppress my inner voice to dress up and be a female. When I got married at a young age I always encouraged my wife to dress up sexy and show off her body and the things that she wore. This was ok till she found some of my own things and tried to understand. I suppressed my desire and it was a real fight and still is. Does she understand, not really! Does she support it, not at all. This has caused some friction throughout our marriage and raising kids well I backed off as much as possible and keep it a big secret. I am trying to be a good father and husband but this urge grows strong every now and then where I wear my lingerie under my work clothes. I do love the story and I feel that being on vacation and really expressing your true feeling is great for the marriage because she is part of your experience.
Good for you. And good for your girlfriend for adjusting, sharing her thoughts and feelings and even here suggesting you doll up on holiday and bringing the goods.
For your questions…
Yours is a very nice story. Thanks for sharing this.
Dani
Thanks for sharing your experience. I have definitely experienced some mixed feelings from my wife over the past years. At first, she thought it was odd that I would dress as a female, but didn’t come to the point of telling/asking me not to. Then, for a while she was ok with it, even to the point of going shopping with me and allowing me to wear skirts around the house when she was home. Then it turned around again to “I just wish you would stop!” We are now at a don’t ask, don’t tell stage where she knows about my dressing and my extensive wardrobe (she will occasionally go through my things when I’m not home), but she wants nothing to do with me presenting as female. It can get a bit confusing.
Mixed messages and limitations OH YES! I’m 74 now and we met as 15-16 year olds. The Viet Nam war took us apart and 34 years later we remade the connection. As teenagers we experimented with her dressing me as I encourages her to. FF to 2002 I told her right off as she noticed I was wearing panties. I shipped some of Lauries things to the other coast so we could enjoy the two of us rekindling the idea of having someone completely accepting my crossdressing. The result was a sort of a purge as she encouraged me to be more naturally feminine and so much less the hooker look. All new wardrobe, six wigs and a discovery that I could really be the girl I had always wanted. We shopped together made a new life and moved to a gated community to enjoy my and her retirement. Money was not an issue and I continued to acquire more things until more than 3/4 of my walk-in was all girl. The caveat was NO outside dressing and no one else was to know of our secret. As we reached a comfortable acceptance of Laurie in our lives the outside world began to close in on us. We became very visible and active in the community and civic demands began to intrude on my dressing that I was now doing just about every day in some way. She has informed me in certain terms that I need to back off the casual way I add something feminine to my self. Several weeks ago a friend noticed I failed to remove the small magnetic earrings when going out to golf. His wife mentioned it my wife and we had words regarding it. I have a Flickr account https://www.flickr.com/photos/lauriejp3/ and she has refused to take any more pictures of Laurie. She used to always style my wig and make comments when I looked especially nice. Now whenever I order from Amazon a snide remark like “really again” has been the response. I have found myself seriously putting off getting completely transformed, dressed, makeup, nails for sometimes weeks. Even I have noticed that I am more easily upset, angry and often not the calm person that was present when Laur came completely to me 4-5 times a week. So I would have to say, yes the thrill is now a mixed message.
wow what a vacation that was for you. yes i get 2 different waves of my wife with my cross dressing, she knows and tells me when i can dress up and she will not help me with make up, she has seen me getting dressed up, but will not let me sit in same room as her, she knows of all my female clothing, i have more then her and seem to wear them more then she does. i took over her dresses for she dont wear them any more and i fit into them just fine. she has gained a little more weight so she can not fit into them. i love dressing up all the way i feel happy and relaxed and look pretty thanks for sharing your story with us wish my wife would be that way to me
My wife is a little vague about where she stands with my dressing.
She is 100% ok with me wearing skirts so I wear them everywhere, every day.
Likewise underwear, all my “panties” are female, she is ok providing they aren’t overly frilly or floral. Tops too, as long as they have an androgynous look.
Tights and pantyhose are ok, too.
Ladies’ shoes, bras, makeup, dresses – all no-no’s.
I love wearing dresses and heels, and do when she isn’t around, or if I’m away.
It is my dream that she took positive action and led the way, or gave me clearer guidelines around her boundaries.
Hi Sondra!
It sounds like she is trying to keep you happy and understanding your needs and for that, you must always respect her wishes. I have been dressing since I was a little child, never stopping, always in secret and through several years of a relationship and marriage to my wife. Of course, a year afterwards I got “caught” when she found some pictures and thankfully she didn’t freak out too much.
On and off over the years, I’ve going through times of hiding and being out in the open…for several months it was go ahead and dress…where is Maria? How is my Maria and then always stay inside. Then she would keep quiet and I wouldn’t dress for months. Suddenly in 2019 she found a group here close to home through MeetUp and a monthly party, which I did for a year, with her actually coming to the last one that we attended in December 2019! But sadly covid hit and it was bad here so I haven’t been back since, and the numbers are on the rise again, so Maria is staying home for everyone’s health and her own.
It is a rough road at times, but try to remember that she is the one that is bending and we have to respect her wishes. If it goes full negative and you start to realize more and more that you need to be Sondra, then you should consider a different lifestyle instead of “stringing her along”. We understand our arrangement and sometimes I have to remind her that I’m ok and happy the way we are….we have been together now for over 35 years now and I wouldn’t change anything. oh, and everyone in my immediate family knew about my dressing after getting caught a few times so maybe that helped her to accept as well
stay well and safe!
Everyone’s story is different and also the same in some ways. I am married 50 years and have accepted that my wife will never have anything to do with my femme side. I know if I had told my wife before we married she wouldn’t have married me. She knows 40 years. Balance is the keyword in my life.
I was drawn to women’s attire circa age 13… always felt guilty about it, tried to stop, and managed long stretches, thinking I was “cured”, so never said anything about it to my future wife. But urges came back ever stronger and I started hiding lingerie, which I’d take on trips. Ultimately she found my stash… thought I was seeing someone else. I eventually did a dumb thing and let her find me wearing an outfit she had put in the Goodwill bag. She just said “interesting”; neither of us dared talk of it. Then we hit a rocky patch in life where she determined to see folks I did not approve of, saying she’d rather be with them than me. That popped my cork and I decided if she was going to do as she pleased I’d resume dressing. That led to her moving out without a goodbye. I was devastated and nearly committed suicide. I decided to use my “free” time exploring my fem side, which opened up new, fantastic vistas and experiences. After nearly a year I met a lady and started to get serious so told her of my dressing. Amazingly, she accepted it and immediately started mending my dresses, buying me clip-on earrings and other fem items. My wife then decided to return, putting me in a dilemma. I decided to give the marriage another go on condition she could accept my dressing, which I knew by then was not something I could stop. She made a great effort and seemed very accepting over time, with boundaries I could accept. I thought everything fine until one day she insisted I find a cure as she could no longer handle it. I did all I could, but we all know where that led. Counseling did no good. We legally separated, then divorced. I resumed my relationship with the accepting lady. Things only got better. One day she told me “You really need to wear a bra.” Music to my ears and of course I complied. We’d enjoy ladies’ days out and just about everything two women could enjoy together. Recently my heart sank when she told me I was dressing too much and she didn’t like it. She especially wanted me to stop wearing a bra. For me, that’s the most important garment required to feel feminine, and I had long thought she fully approved. I told her I could tone down, but not to that degree. We are seeking a happy medium now. Sometimes she does not even realize I am wearing a skirt, perhaps asking in the evening when I put it on, only to be told “first thing this morning.” But it goes from being an unnoticeable event one day to something deeply disturbing to her the next.
Recently her Mom died and she asked me if I’d like any of her silky slips. Of course I said yes. She seemed ok with my wearing them to bed after I reminded her that they were not much different than the nighties she will usually allow. I then pulled out a bra slip I bought many years ago and wore that to bed. The bra seemed to bother her but she thought it was her Mom’s, which she had offered me, so that now seems to be ok. She mistook another sexy chemise for her mom’s also… something I had not dared show her before. So acceptance is a function of whether I have crossed a line, it seems, and while a bra is now something she’d rather I retire, I’m ok if she thinks I am wearing a gift from her.
I noticed that my men’s underwear has dwindled to only two briefs, both somewhat feminine, and she now wants me to get rid of my T-shirts, which she prefers I not wear under my men’s shirts. She realizes my vanities are too stuffed with lingerie and I need more room for fem items, so it is clear my men’s stuff must go. We’ve hit a sweet spot, I think. But I’ve learned from experience that it is unwise to count on remaining there.
I suspect this theme is common to many. I have known a great many crossdressers with very supportive wives who suddenly shut the door on dressing. This is always very hard on the CD and the relationship.