I Have Shared My Crossdressing With A Few Women

There are a few women that know about my crossdressing. My wife knows, of course, but there are a few others. Mostly ex-girlfriends. From the time I entered college, the girls I dated with whom I had somewhat serious relationships all learned of my crossdressing.

It's interestiing, because all of them accepted my CDing to some extent. A couple of girls found it "interesting" and were curious to see it. Of course, after seeing me in a dress, pantyhose and high heels once or twice, they got past the curiosity element, and were not exactly excited to see me dress up.

One girl I dated was a bit kinkier, and enjoyed it more. But she and I just didn't quite click, and so the relationship didn't last long.

My wife is understanding and accepting, but my CDing is not a turn on for her.

I have also shared my CDing with a few women that are friends.

Two of them were accepting. One friend is amused by it all. She likes seeing my legs in hose, and has even borrowed my heels a couple of times. Another female friend was curious to see me totally enfemme, but wanted to share that experience at a hotel room. The problem was that we're both married, and I was not interested in having sex with her and cheating on our spouses.

Two of my friends were less than acceptings. I was opening up to one friend and told her about the time I dressed as a girl for Halloween. She asked if I had worn pantyhose. I said yes I had. She then gave me a big, "Eeeeeewwwwww!" That was enough for me not to finish the story and fess up about my CDing. I shared the Halloween story with another friend, who told me in a very repulsed manner, "that is SOOOO gay!" She stopped talking to me after that, so we are no longer friends.

I know it's a tough thing for CDs to share their secret with people. It's something that we all wish we could be much more open about. But so many people can't handle it. It's a tactical thing to tell someone when you aren't sure how they will react. You hope they will accept it, but if they don't, you hope that they will honor your secret. It's not that I am worried about losing a friend by telling someone, as much as I fear what would happen if they began telling everyone else about it.
BizSuitStacy BizSuitStacy
56-60, T
9 Responses Sep 14, 2012

It can be very scary. I have two female friends who actually help me shop for what looks good. Beyond that, it's a dicey proposition telling someone about your innermost self

That's great you have friends to help.

I think crossdressing is somewhat unique in that you can never be truly sure how others (in most cases) will respond to an admission till you've done it. I suspect that the uncertainty is driven less by how THEY actually feel than by how others might view THEIR casual acceptance. Coming out as gay is easy by comparison; we've collectively got over the prejudice by and large, and it is well understood that to be seen as an anti-gay bigot will be to your detriment both socially, and quite possibly in the workplace where it may have legal implications for your employer. But although the same is theorectically true for TG (in the UK at least), society hasn't quite caught up and it still somewhat acceptable to laugh at crossdressers at least in social circles; perhaps because we come in so many apparent 'flavours' or because sometimes it just doesn't fit the social norm of 'decorative', particularly for the inexperienced. Yes, its shallow, but society is usually that. So, back to the thread, people perhaps fear being seen by peers as condoning something that is still something of an ignorance fuelled taboo, and fair game for a good laugh at the pub.

Yes Stacy; probably for those same reasons most of us hold those cards very, very close to our 42DDs. It still has the capacity to cause great damage to a life - more in probability than the person broadcasting it would ever realise.

An ex of mine who knew the lot twenty years ago (supplied some of it!), and with whom I parted quite acrimoniously, went to very great pains afterwards to reassure me that, she might loathe me, but she'd never breathe a word, and to my knowledge, she never did.

Excellent points. Particularly the bit on someone's uncertainty about crossdressing is less likely to determine how they really feel, than the perception others may have of them based on casual acceptance. Very perceptive of you, and of course very true. I know my own wife does not want anyone to see that I have on pantyhose/tights under my pants...not because it offends her, but instead because of what others may say. She is ok with it herself, but she's not ok with anyone else knowing. I'm quite many other CDs are in the same boat. Such is the life of a CD.

Like you, a few people know. the wife, of course, the sales ladies at the store, a motel clerk and the motel maid in another state, the girl working the McDonalds drive thru (in another state), and a ********.

At the motel, the maid was just finishing up my room when I returned. She said the manager would be speaking with me later, as I had rented the room for one, but she saw that I had a friend staying with me, as she glanced at the clothes hanging on the hangers in the room. I told her I was alone and she motioned to my clothes. When I said they were mine, she gave me a look and went to the room next door. I quickly changed into my hose and a short dress and went looking for the maid. When she saw me, she apologized and said I looked great. When I went to check out, I was wearing my spaghetti strap top and shorts. The clerk said, 'you look like you are ready for the beach'. I said could hardly wait and left.

In a separate outfit, at McDonalds, I got a nice smile from the drive thru girl.

But the ******** was the best as her brother was trans and she offered me places locally to shop and offered to help me get the right fit.

Very nice. Interesting how we can get different reactions from people. Getting caught by the housekeeping staff at a hotel is something of a personal fantasy of mine.

I am at the point where I sometimes go to the womens clothing stores to buy some items. I was at a mall where I bought some thongs. The sales lady rang me up. Later on she got off and and caught up with me and we were talking. She asked me who I bought the thongs for. I told her for me. She smiled and said she was glad to see a guy who is finally claiming the freedom of wearing what is comfortable. But there are others who want to make a negative scene about it. 2 people tried to do this about a crossdresser. I walked to him and said let's go. If they want to make a scene let them make fools of themselves and let them do it on their time. Then we talked and I told him about myself, he realized what I mean about it.

Very kind of you to support the other CD. And nice that the sales lady chatted with you after she got off work. Women who work in lingerie departments long enough eventually run across crossdressing customers. I suspect that some stores may even train their employees to address those situations. Many CDs have stories of receiving great customer service while buying articles of women's clothing for themselves. And of course, you also hear stories of women making fun of CDing customers. You really never know exactly how people will react.

Mostly I get good to great responses. Ones I run into are negative. They have their tactics down to a tee. They initiate, get someone to assault them so they can press charges or if they protest publicly they try to get the police to make a mistake and file lawsuits so they get money to do more.

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Once camping with a bunch of guys around Halloween I mentioned that I had gone to a costume party dressed in women's clothes. The negative response made me regret telling them. But a couple of months later on of the campers ( a long time friend) asked to see my outfit. We were at my home and alone. I laid the corset panties and nylons on the bed and hung my dress at the bedroom door. After seeing the lingerie he asked if he could try them on. It was easy to see that he got pretty excited about wearing them, but I nothing more came of it that night. About a year later he asked me if I still went to the annual costume party and I offered to dress for him to see. Shaved legs chest and underarms. Toenails painted red and fake red fingernails. He couldn't take his eyes off of my. After I sat down he kept getting up and looking up my skirt. And I gave him plenty to see. We eventually went into the hot tub, him naked and me in bra panties garter belt stockings makeup wig and jewelry. Finally ended upstairs in the bedroom for my first ever BJ. What a night

Oh my! You went into the hottub in your lingerie - including stockings? I find wet clothing ultra sexy. That would have given me a stiffy. LOL

I am good at writing erotica and would like to exchange some experiences with you , if you care to .

I have written some erotica too. Not sure how good it is but I enjoy it. I am sure I would enjoy yours too

I am a complete closet case, so much I don't do it that often anymore. My partner is not turned all at the thought, so I've never pressed the issue. If only we could all be free to be as expressive as we want.

It's most difficult for those with a partner who is unaccepting. And indeed, it can drive us even further into the closet.

I am a closet crossdresser. I told my wife that I used to do it, but she didn't like it, so I hide it from her, unfortunately. I also have never told friends or coworkers. I almost did one day, though.
I was walking to work early one morning when I saw a well-dressed woman walking toward me. As we approached each other, I saw that she was not a woman! I just smiled, but didn't say anything. At work, I told a coworker, who is a few years younger than me and attractive. She thought it was great! I asked why and she said, "Any guy who would do something like that has guts. I love crossdressers!" I asked her what she would do if she were to find out her husband is a crossdresser and she said it wouldn't bother her, but she wouldn't be turned on by it, either.
I decided I shouldn't tell her because of that, and because I knew she would probably tell other coworkers. But I sure did think about telling her!

I like your experience of seeing the "well dressed woman!" I had a similar experience at the airport. I had just gone thru the security line, and was putting my shoes back on. I noticed a woman in pantyhose putting her heels back on. I thought, "gee...nice to see a woman in pantyhose these days." Then, I got a closer look...not a woman. I smiled at her, but she just seemed uncomfortable. Maybe she knew I had figured her out.

Very few crossdressers seem to risk being in daylight . I remember only one - a supermarket cashier in Key West - and even he , tired and bored by the job felt the need for a quick searching glance to get a handle on my response to his appearance . I may have missed identifying really successful cross dressers ( which I wish I were ) , and those guys with hormone induced breasts often have somewhat feminine faces too , so they may escape identification , but for the most part I think crossdressers must have the fear I have of public humiliating encounters .
Is it , as I have heard , publicly acceptable in the Phillipines ?

I was completely secret untill 4 years ago. My marriage was a bit rough. Somehow I ended up in another womans apartment, wearing her heels. We were both drunk and couldn't quite remember how. She was really accepting, she was great about it. She gave me that little nudge I needed to have the confidence to tell more people.
My wife has been the tricky one, but I think she worries too much.
I have told 3 female friends and 2 of their partners. The girls were great, they want to dress me up and get me out there. One even donated some old shoes. The guys were less enthusiastic, but still kinda accepting in a funny masculine way.
The one person I really want to tell is my mummy, but how do you approach that one?

I'm not sure exactly. Mothers are very accepting for the most part. My recommendation would be to be very honest with her. Sit her down, tell her you have something important to talk about. If and when you tell her, be prepared for all the questions she is likely to ask (you know the standards..."are you gay? do you want to be a woman? etc.")

You are much braver than I. I've told no one except my therapist. My wife knows a little but not to the extent. At least she did not run out the room screaming.

That's a good start and as you said, at least your wife did run away from you.

You are so wright, though I told a few people I know that I wear dresses, I still find it difficult to tell. I fear the most of telling men about it, telling women is easier, they seem to accept it easier then men do. The ones I told didn't seem to matter about it, it was alright to them.

I've never told a man either. I feel more comfortable telling women. I'm not attracted to men, and would not want a guy to get the impression I wanted sex because I shared with him that I am a CD.