How did you start cross dressing

[Guest Destiny Lynn]

Like Amber Mom wanted a girl. Dad joined the submarine service 1943 at 15 years old, did the war, 20 years on subs. No shore duty "floating a desk" the entire time. He was gone a lot. Mom dressed me as a girl too. I can't remember who deterred this, my uncle or all 3 I believe.

There was a clothes hamper in the bathroom. I'd take out Moms under things and wear them. Sis had some nice stuff but being 3 years younger they didn't quite fit. Arousal? Oh yea. "what are you doing in there so long?!"

Later thru life it was on and off. Depending on partner, circumstances, living quarters. Now, I do what I want and do it more often! That's full dress anytime I can. I haven't been out in public yet other than walking 250 yards to my mail box and even that feels so awesome. I'm looking forward to being out in public.

I also have full support from my wonderful SO, Candy. Without her I'd still be a bearded circus lady with my makeup done as nice as a circus clown. She shares her things with me, buys me outfits, makeup, purse and helps me act like a lady. Always so nice to me, never laughs when I mess up bad. Once I was putting on eye shadow and put some under my eyes. "honey, you don't need to do under your eyes"

Destiny Lynn

[gennee]

I started when I was fifty six. I never put on a woman's article of clothing as a child nor did I have any desire to. Lived life as your typical male. It was in 2005 that I got the urge to try on my wife's skirt. It was crazy because I never had such a desire before. After many days I relented and acted upon the urge.

I thought it would go away but instead it set the wheel in motion in which I couldn't stop. I purchased bras, panties and tops. My wife fond my stuff one day so I had to 'fess up. She was shocked when I told her. It took time for to accept this part of me. In time I found that my feelings ran deeper than wearing clothing. I learned through more research that I was transgender. I haven't looked back since that day of discovery.

[Guest Emmais]

Hi ladies

I am new here but I would like to tell you my about my journey. My marriage broke down and I met a girls at work who I took a fancy too.

A long story short. We chatted often and one day she mentioned she was wearing new silk underwear. I said jokingly, show me, well she showed me her panties and I said there very nice, do they feel nice, she said yes and out of the blue she said, would you like to wear them. Shocked at my answer to this, I replied oh yes please. The next day she brought them in for me, washed. She said go on get them on and show me. I did and they felt very nice. We linked up at lunch and she asked to see them, so I showed her, how do they feel, I replied very nice. She said I should wear them often. I told her I have only got the ones she loaned me, she said have those to start with then and we can go shopping at the weekend.

We did and bought several pairs she picked out. At 60 I had no idea I would take to wearing women's panties. Needless to say it did not stop with panties, then came the bra and boobs, skirts, nylons etc. she tends to dress as a man, which I have no issues with as she looks good. It is only in the past 6 months she has permitted me to go out en fem. we have been very happy now for 4 years.

She does not want me to go full fem but we are both happy as we are.

[Guest AllisonRae]

How did I start, well back somewhere when I was 9 to 12 I started trying on my moms bras and undies and putting on makeup. I had no sisters and a half brother that was 12+ years my senior. This kept on till my mud teens when I started getting scared of being caught. The next time was in my mid 20s, I collected my girlfriend's bras as kinda a gag, but I could not resist trying them on. My first full fledged crossdressing began with my first wife. Most of the women I have been with in my life are a similar size to me. She would pick clothes for me and do my makeup hair and nails. I was passable thanks to her. This is when I started hearing that voice saying go farther. I began investigating gender therapy, HRT and SRS. Even started working on my voice. Around this time my first wife turned on me, she left me for another and told friends and her family of my secret. I was completely devastated. I tried burying that part of myself. I married again, this time to a control freak and Christian fundamentalist. I dared not dress, though I did a couple times when she was out of town. I did purge my clothes and forms during this period. That marriage ended 3.5 years ago with me in therapy as a victim of mental abuse. I started dressing again about 2 months ago when my reality finally dawned on me, the reality that I am transgendered. My SO has tried to be understanding, even donated panties to me and has taken me shopping a couple times.

Hugs

Allison

[Guest Eve Caillard]

Oh Gennee I was exactly like you! 53, and apart form some sporadic cross-dressing as a teenager I never thought once of it over the years. Yet I still tried on the odd item of my wife's, thinking it harmless curiosity. But when it came to the fateful cold February that I decided some tights would be good against the cold, the floodgates opened. And once open - I could not stop. And do you know? I am so happy! I am so glad it happened! Like you, I never looked back and I also, finally, understood why I had so many issues over the years. I really know who I am and why. And it's great!

Emmais - you seem to be in a great place. Well done!

Eve

[Guest Arinda]

Thank you for sharing such personal stories! It's touching that you care enough and are open enough to help others like myself learn and be supportive! I see that some people have not listed the state/ province they are in. Is there anyone in the Texas area? I think my husband could benefit from a local mentor. I am new to the site. So, please forgive me if that is not an appropriate question.

Arinda

[Guest Ellyssa]

Arlinda:

I am not in TX but travel there often. While I'm on the road, I have opportunity for some dress up and I found a place in the Grapevine area, a suburb of Dallas near DFW airport. She is closing up shop soon (this month) but might be able to help out with some clothes, makeup, etc. which she is disposing of. She was very accommodating for me and will probably be able to steer you in the right direction for further help. She also performs monthly in a girl band named CHIX, it looks like a fun 80s and 90s cover band. If you're both ready for going out, that would be a fun girl's night out. Here's an article:

http://www.dallasvoice.com/femme-service-people-learning-women-1074497.html

She has an incredible website too: You will need to use your search engine to find her.

She is moving on but I would have loved to have had the opportunity for a makeover and a girl's night out. I'm a little new at this myself and I still felt completely comfortable with her.

On the behalf of your husband, thanks for being accepting and investigating this for him. He will appreciate it so much!

Good luck.

Edited February 10, 2015 by Ellyssa
link removed as per terms and conditions

[Guest Ellyssa]

Mod: Sorry for the violation on the link, just trying to be helpful.

Arinda, if you'd like the link I can PM it but it's easy enough to find.

I'll be in Dallas in early March (after Nikki closes shop) but I'm also hoping to visit a salon in San Jose in mid-March, if logistics work out. Insert emoticon with crossed fingers here.

[Guest Lynnette Rae]

for me it started when I was 12 or 13. I helped with the laundry and stole a pair of my sisters panties and a bra. I would wear them every chance I got. as I got older I would get things from here and there I would even buy things for a girlfriend. I stopped for a while then I would go back to it. Then I stopped just before I met my wife I was 38 and it seemed like I was always angry and moody. I recently told my wife about Lynnette and she told me to be myself and proceeded to buy me my own things I now have several outfits, my own bras and panties she bought me my very first pair of heels, she went out and bought me some makeup and is teaching me to put it on. soon I will be getting breast forms and a wig and then we will be going out for a girls night out. we have been married for 10 years and I know I should have told her sooner and she said I could have. she is a wonderful and understanding wife. I now get to be the person I want to be. I am out of the closet and don't have to go back in.

[Guest Krysii]

Wow! I have read every post in this thread, my eyes are watering, my throat is tight. Lots of whiskey has slipped down my throat this evening, probably a good thing, as this is my first post here or anywhere else. I love the spellchecker.

Spent a long time the past twelve months pondering my life. I think I was about 5 years old when my parents were having a very opinionated conversation about the headlines regarding Christine Jorgensen. I probably don't need to say they were oppositional to the concept, and the person. I remember that I wanted to be her. I didn't follow her life, as I was into howdy doody, the lone ranger, etc. About 10 years old the girl Barbara (my first real crush) told the day camp leader that I was too cute to be a boy. Between then and now, a veritable plethora of collecting, purging. Hiding, hiding, hiding. So many times I have heard "I have never known any one like you", or "I've never met a man like you", or I don't know what it is about you." I have known a couple of women who wanted to dress me in women's clothes, or lingerie, but never felt I could really be free with the knowledge about me. Silly me, now I look back and see many people knew I was a sissy before I did.

I just put together a new wardrobe, wigs, makeup, shoes, lingerie, corsets, stocking tights, oh yessss Panties. I want to make my own custom panties/gaffs. I tuck and wear a bra daily, I am working through the paranoia of leaving the padding in the bras. I have the butt pads and the hip pads. Truly, very little in the way of men's clothing fits me. I love to wear tight jeans to work. I love wearing skirts and dresses at home even more. I can't wait to get changed most days. Even though sometimes I am delayed until I put on my night gown, nighty, or silky satin pajamas. I dream constantly about living full time as a woman. I can never do that until I disappear and show up in a place unknown to all my family. The posts I have read about family choosing to love them less or not at all, bring me close to tears, as I know that will be my fate. That has always been my fate, as I live with my secret, so it doesn't scare me. I have lived a lonely life, one that I would categorize as a solitary life, but in reality a life afraid to be me. Maybe this is the wrong thread for me to go on this long rant.

First time out as femme, 15 years old driving around in my mothers car with out her knowledge. One of the most delightful experiences in my life was recently going to walmart at midnight to buy cosmetics, dressed to the nines.

Thank you all for sharing your stories, Lizzy, your photo is just beautiful.

[Guest moderatemania]

No one has mentioned on this thread the one thing that I felt drove me most to try my first CD, and that was a lack of access to revealing female pornography. Wanting to see the female form but having no way of doing so, I modeled my sister's panties in the mirror, making my own body into a manequinized female image. Of course, I found it immediately arousing and by the third time the sheer turn-on of putting on panties had fully eclipsed the original motivation. I was no longer dressing to give myself homemade visuals in the mirror - I had started doing it to feel the way a girl would feel when she wore the panties on herself. At that point, I let go of the mirror. The feeling of the underwear on my body became the primary thing. It has taken me most of my adult life to come to terms with these early-onset crossdressing tendencies. This forum is the first and only place I've shared about any of this. I'm not sure what I hope to get from it, but I hope its not regret.

[Guest Jocelyn1975]

The very first time I was crosdressed was by my mother she put me in a strawberry shortcake nightgown, I was around age four and this was a punishment for setting my clothes. I liked it and as a teen I used to wear my mother's and sisters undergarments until my sister caught me with her panties. I didn't touch any more clothing till I was married.

[Guest Hal9003]

I remember my first time, almost 40 years ago, as if it was yesterday. I was in my early 20's, and was having an affair with my next door neighbor; she was my Mom's age. She wanted to keep doing it multiple times a day and she started off putting her panty hose on me; I responded immediately. Then she started to put more and more of her cloths on me and I began to feel more and more comfortable dressed as a woman. She started to take me out as a woman; we would shop for woman's cloths for both us. We would go to lunch, we were two woman enjoying each others company. We were still lovers, but it was different. It was incredible!

We were out one day and decided to go into a bar and have a drink; it was an event that caused me to have gender confusion for the rest of my life. We ended up getting picked up by two men and actually dated them for several months. i was a woman in a relationship with a man. It felt so natural and we looked like the perfect couple. My male side is still the most dominate, but I still dress when my wife is away, but age has been cruel to my passing.

[Guest lilygirl]

I started when I was around 10 or 11 with some of my mums pantyhose, and later a swimsuit, because I wanted to know how the skin hugging material would feel. I loved it and was surprised it also made me feel feminine and I liked that. So I started wearing her other clothes when she was out too, sometimes spending a whole evening in front of the tv or doing homework dressed up fully, which I found strangely relaxing. When I could sneak something away without being noticed I would sleep in it too. I found a pair of pantyhose in the school lost property and took them, feeling very bad like I was stealing but not knowing how else to get clothing because I didn't have much money and would have been far too embarassed to go into a shop anyway. Sometimes I would wear them under my jeans when I went out.

Another factor was similar to what moderatemania mentioned above, being able to look in the mirror and enjoy a femine form which I didn't otherwise have much access to. Almost like roleplaying the girl I wish I could be with, representing an image of something I was sexually attracted to. But then, discover I also identified with that image!

[Guest bobbiw]

Hi All,

My name is Bobbi. Wow, what a great question and so many compelling posts in response. I can't remember the exact date, but I can vividly remember the first time I dressed. It was in the summer when I 13 years old and sleeping over at a neighbor's house. There were three of us total. The other boys suggested a game of truth or dare. The neighbor hosting the sleep over had an older sister and during the game it occurred to me that a great dare would be to put on his sisters panties. We went to the laundry area in his basement and found panties and a bra.

That night wearing my first set of panties and a bra I felt so excited. In addition to the excitement, like many others here have mentioned it also made me feel closer to the girl I didn't believe I would possibly have a chance of dating.

Over the past 40 years I have dressed and purged in secrecy several times. Sneaking clothes when I could and always feeling ashamed. I was certain it was a phase I would just out grow. At first I thought the switch would flip off when I turned 30, then 40, then 50. I still don't know what drew me to dressing, but I've come to realize, for me, it is not a phase to be gotten over and I can finally say that I am comfortable with who I am. During the past few years, I have built a collection of panties, bras, skirts, tops, wigs and makeup.

I have remained in the closet all this time while raising a family, being in a long term relationship and building a career. While there are many times now I wish I were out, I don't know what impact that would have on my family and I am not willing to risk hurting them. So staying in the closet is the choice I've made over all these years and I'm comfortable with that choice too.

Thank you all for listening, I didn't realize how much I had to say.

Hugs,

Bobbi

[Guest Ellyssa]

Wow, I looked at Mom's stuff with curiosity, what is it like to wear it, how does it feel, and thought over it for a long time before finally trying on some underthings when I was ten, fooling myself by thinking that I need to know how do you get these things off of a girl? But they felt good and I wanted to try on more things. I suppressed it for another long period of time before trying again, lying to myself that I wanted to know how my someday girlfriends would feel in it, to empathize with their foreign way of dressing. Eventually I stopped kidding myself and realized I like feeling that way but still felt guilty. Then it became more common, then I asked myself what the hell am I doing and stopped for a while. But they kept pulling me back in! Finally, I think I was 15 and dressed fully. It was great! I went through a period when I dressed every chance I got. Then I felt guilty and stopped. Then I was 17 and tried makeup. Garish attempt but it was fun too. And then I shut it down again, guilt and fear consuming me. It mostly went away in college, although I did try on a couple of girlfriends things when they were away and I had keys to their rooms. I graduated and was busy with grad school, then married, then kids and life was too busy then it hit me again, my wife's closet. I really haven't been able to put it aside since. I don't think I'm horribly abnormal and I'm not guilt-ridden anymore but it's only taken me 30+ years to get to this point. Slow learner!

[Guest DarlaVal]

I feel I was born to be a CD. I'm 67 now and have been wearing fem clothes since I was about 8 or 9. During my teen years I mostly I pinched stuff from my mom and sisters but started buying my own clothes after I got my first fulltime job in 1970. I would order by phone from a JCPenny or Sears catalog then go to the store and pick it up. After I got married in 1977, I hid my girly stuff from my wife until, after two kids, I camer out to her in 1983. She wore my size clothing (I am a wee sort of person) so I told her of my activity and where some of her missing lingerie could be found. After the kids went to bed that night, she asked me to model my outfits for her. I did and she became jealous that my clothes were nicer than hers. After that, I was open with her about my need to wear panties and bras during the day and night gowns at night. Surpsingly, we stayed married until 1996 when we divorced, (Within a few months, she came out as a lesbian and married her current partner a few years ago). I've chosen to remain unmarried and unattached to any SO.

I retired from fulltime employment 5 years ago, and extreme introvert that I am, stay home where I wear femme or androgynous clothing fulltime. The only times I go 'male' with the outer garments is on those few occasions when the grandkids visit or I go out to a restaurant with friends and family. This is my life and I would not have it any other way.

[Guest notsure2015]

For me it started when I was 6. I always wanted to try on my sisters dresses and panties and one day I tried on a pair of my sisters panties and it was amazing. I was so scared to be caught I stopped immediately. The urges came back in high school and I began trying on my sisters bras and panties on again and started going further with dresses and one piece bathing suits. Again I stopped and the feelings are back again for me. I don't have much privacy so I only get to dress on the rare times when I'm alone. I've been trying to work up the courage to start under dressing but haven't made it far. I've gone on a few short errands wearing panties but not often or long. I feel I need to explore under dressing more and I'm too worried to start wearing panties to work and school. There's times where I just feel too ashamed of myself and put everything away. I've been stressed out lately and I feel that under dressing may help to relieve the stress cause it feels good and I like wearing bras and panties but but there's still the shame that follows later. Right now I'm working on getting over the bad feelings, I got my bra, panties and thigh high stockings on under my jeans and shirt. I'm hoping to come to terms with my feelings soon.

[Rowan]

Wow, some great stories here. I guess the earliest instance I remember is being about 6 and sneaking into my mom's closet to try on her high heels. I remember walking around the room, pretending to be a woman. That happened a few times, but not many. Then, when I hit puberty, the urges to wear women's underthings hit me hard. Every chance I got, I'd borrow my mom's panties, bras, and especially panty hose. There were a few occasions I'd even borrow a dress, but I didn't usually have that much time. I thought I was being careful, but looking back, I'm sure my parents had their suspicions. There were a couple of times when I'd try out my mom's lipstick or mascara. But after my mom asked me if somebody had been using her lipstick, and I blamed it on my 3 year old little brother, saying that he had gotten a hold of it, that I decided to stop. I knew I was getting too reckless. It wasn't until my early 20s that the urges really started coming back. By then, I was married to my first wife. I think having all of her feminine clothes in the house is what triggered it. I knew I couldn't get away with borrowing my wife's clothes because of our size difference (though sometimes I did get desperate enough and risk it), so that's when I discovered the amazing eBay. I secretly got a post office box, and just went crazy. I bought all kinds of things. I had an amazing collection of panties, bras, tons of stockings, corsets, wigs, dresses, and makeup. I dressed as much as I could for about 2 years. Then, I did the usual guilt/purge thing. Man I miss that stuff. I then went a few years without dressing. Then I went through a divorce about 5 years ago, and it all started back up again. Except this time I was single, so I didn't have to hide it in my own home. It was so liberating. I had things delivered right to my front door. I shaved my legs. In my home, I could be as feminine as I wanted, and I loved it. But I was also very alone. I started dating again. That's when I found the love of my life. I continued to dress at home, but then I made the decision to give that up when I asked her to marry me. Before she moved in, I purged all of my things again. That was a little over a year ago. I haven't dressed since. But for awhile now, I've had the urge, and I know it won't go away. And I really don't want it to go away. I love my fem self, and I can't wait to see her/me again.

[Mayo]

I think I'm atypical for a CD in that mine is of late onset, though a few of the posters above (e.g. Gennee & Eve C.) had vaguely similar situations.

When I was in my late pre-teen years, as part of my sexual experimentation I tried on my mother's bra and panties, but apart from doing so a couple of times just to see what it was like I didn't pursue it and never really thought much about it afterwards. Although I engaged in sexual experimentation with both boys and girls during those years, I was fairly shy and in my teens got it in my head that if I'd been a girl it would have been easier to attract a partner. I think that stuck with me at an unconscious level through the boring cis/hetero years of my mid-20s to mid-40s and when I split from my wife I started having sex with both men and women again. I was also roleplaying a female character in an online role-playing game and discovered that I was very comfortable in that mindset. I've also generally been more comfortable around women than men. These factors, along with a resurgence of that teen thought about being female (and the discovery of trans porn ), opened my eyes to the possibility that one could be non-binary, and it was only then that I tried CDing as a way to express/experience the feminine aspect of myself.

I dress in private most days now but am still unsure of my exact position on the gender continuum - I'm currently identifying as non-binary because I think that I'm more than 'just a CD' but, while I occasionally experience some dysphoria, I don't have sufficient motivation to transition (though if I could wave a magic wand and turn into a fully-functional woman in an instant, I would almost certainly do that...).

[Guest Eve Caillard]

@Mayo - As one of your quoted folks (thanks!) I feel much the way you do. Discovering I am a CD has been a total shock to my system but if I could wave a magic wand for an instant transfer - I would do it. I think one of the most surprising emotions I discovered was jealousy. Jealousy? I was jealous of women who looked and lived like I wanted to be. And I feel way more comfortable in groups of women. Men scare me. I don't quite 'get' male company and I end up on the outside. It's a confusing world.

Eve

[Guest AshleighP]

Eve, I have those same feelings of jealousy. When I see someone in a cute outfit, I feel it's not fair! I want to be able to go out dressed like that too. I take advantage of every opportunity to dress now, even if it's only for an hour before I go to work.

As for how I started, my first memory of cross dressing is wearing a pair of my sister's tights when I was about 10 or so. I loved how they felt and looked. My dressing was sporadic for many years and at times I wished the desire would just go away. At this point in my life, I am very glad that it didn't. I love how I look and feel when Ashleigh gets to be herself.

[Rowan]

Hello chelseymichelle,

Your story is almost exactly the same as mine, my first wife was in a way the access to female clothes, she was very open in sex issues at first and I was able to dress her in the way I wanted to dress myself,

I used to try some things but there was a great difference is size, I also bought, hid and purged.Your needs will not go away,at some stage all will out, I am lucky now that with my second wife, after lots of stress, tears and understanding I am able to dress in the evenings two or three times a week depending on when it gets dark, but I have lost certain aspects of our marriage.

Do be careful and try to let her know before you start,

love and hugs,

vivianmichelle

Hi VivianMichelle! It's good to know other girls who have been in my situation. I've been speaking with a therapist for about 6 weeks now, who has been amazing. I've come to the point where I know telling my wife is inevitable, even if it might be a ways down the road. But it may be soon as well. It feels like it'll be sooner rather than later, but I'm taking it slow and careful.