Why do young boys crossdress?

[Katie Russell]

I think that it is a common trait that many of us start our crossdressing at a young age. In many cases before puberty sets in. It then continues through puberty and maybe wanes during our twenties to mid thirties only to return again. This seems a common pattern although everyone will differ.

It seems to start with general curiosity in our early years and then develops into a 'fetish' during our teens. When it comes back it is more about the feelings in engenders.

I would be interested to find out when people started and the reasons they think it started. Was it an item of clothing, a desire to be like a girl, jealousy or something else.

Did your crossdressing become more of a fetish during puberty?

Did you have a period when it stopped? If it did why do you think that was?

When it came back was their a trigger such as stress at work, family or something else?

Is the pleasure you get from dressing different know to when you were a child or teenager? How is it different?

I have a theory that I wanted to test and answers here may help.

Katie

[Rayleen]

Katie,

It started as a fetish, never stopped to this day

Its helping stress for sure,

one question I ask myself: Why am I not born a female ? Wish I could have.

Rayleen

[Nikki A.]

As for me I guess it was trying to emulate mom, let's face it her clothing was much more interesting. More of a curiosity than a fetish. Later on there was a fetish (sexual) aspect to dressing.
As life progressed due to family and job the urges waned but never really stopped. Now the responsibilities are diminished, more time is available and there is more of an opportunity. The pleasure is now more of a comfortable right feeling

[Monique65]

What Nikki said.

[Jaylyn]

Katie mine began early in life as a baby when mom dressed me but I don't really think that's why I turned to it. I started messing with dressing around the age of ten to twelve when I started playing in moms hose, silk slips, heels and makeup. Loved her girdles and it seemed it always made me feel good when I was dressed. In my teens I dabbled some off and on and it was squally followed by masturbation. Around my high school years sports took my interests. Football track n such. Weight building and working at a job on the farm. College was all about the studies and girls and rock n roll bands I tried to play in. I still loved dating the girls though that wore lots of makeup and especially hose. Finally met one that took my breath away so we were married. I think during our marriage besides having kids, work, and trying to keep food on the table I lived my CD thru my wife. She did every now and then put red lipstick on and kiss me with it on. I'd try to leave it as long as I could before I left the house. I bought her hose and mini skirts n heels and she wore them for me. Thus I survived with limited playing in the CD field. I retired in my 50s and wow did the urge come back the kids were all gone. Wife was still working and I started playing dress up again just like I did in my early years and some teen years. I was under dressing all the time. Finally told my wife and she found this exciting. We even made Jaylyn a part of us. I guess Jaylyn tried to be too much of a family member that she ended up now as more of a DADT. Wife still knows I dress but really doesn't want me to embarrass the family or do my thing outside the house. It's ok with me I still underdressed at the farm as I work and still help her buy her clothes as Jaylyn gets a kick out of her wearing something Jaylyn also likes.
The pleasure I get now is that I'm satisfying something inside me that wants to be a kinder laid back person and the soft under dressing helps in mellowing my aggressive behavior. I don't worry as much and am more relaxed when dressed. I still have fantasies of one day meeting other CDs n going out but they can be controlled by lipstick, forms, bra, and skirts or sexy tops. Love my heels and keep my legs in shape so I can play in them. Stress can cause a deeper and longer CD session for me. If I was a female I would be dressed to the top daily.

[Pat]

Why do young boys crossdress? Because they haven't yet learned they're not supposed to. So they follow their natural instinct.

Why does it "develop into a fetish" during their teens. Because they've learnt they aren't supposed to crossdress and are perfecting their false presentation. However the amazing power of sexual energy in puberty drives them past the self-imposed blockade. They begin to believe their natural instinct is in fact a sexual deviation when it's really natural behavior that can only get past the filter with the aid of sexual energy.

Why does it eventually come back to feelings? Because the sexual energy damps down but the desire to follow their natural path remains and they start to listen.

Does that square up with your theory?

[GretchenM]

Go into the past editions of the New York Times and find the edition for August 8, 2012. Long time ago. There is an article in there about boys who want to wear a dress and how a parent should deal with that behavior. Reading that was a watershed moment for me and I haven't been the same since.

In general, this behavior, although unusual, is not uncommon. The crux of the advice is for a parent to play along with it, allow him to do that, but set boundaries. The thing not to do is probably what happened to many of us. Something to the effect of, "For crying out loud, what do you want to do that for? You're a boy!" It is a devastating moment that results in a need to deny your self to comply with the wishes. In so many words doing that has the possibility of screwing up your kid for life. It results in secrecy, depression, low self esteem, and a basket full of other possible problems, including eventual suicide.

If allowed to express that way, most boys grow out of it by their teen years. If not allowed to satisfy their feeling then they may never outgrow it and it may be a problem for life because of the secrecy needed to avoid being "punished" for being the person they perceived and feel they are. Those who are allowed to express it may not grow out of it and those are the ones that are likely some kind of transgender form. Some of those who are denied and develop problems may also be transgender. I was one of those who were denied which resulted in 60 years of major misery in that part of my life. It was resolved by reading this article, seeking professional help, accepting myself as a type of transgender person, and partially coming out. What would have been my life if my mother had not denied my request to be a girl when I was 8? No way to tell, but it might have been much better. No hard feelings - it was 1953 and the word transgender hadn't even been invented. Nor was there any understanding of this behavior. But that still makes me wonder, what if ...?

Great article. Highly recommended for parents of young kids and for those who, ages ago, were tromped on after asking or getting caught doing.

[CONSUELO]

Many members of this site refer to their earliest experience of cross dressing involving someone, a sister or mother, dressing them in female clothing. That is what happened to me but was it the cause or did it just trigger something else inside me? I don't know.

[Robertacd]

I always kind of liked girs stuff growing up. But I do remember when I was like 10 one of the girls in my class started wearing a bra. I remember feeling that I should be or would soon be wearing one too. Probably like the rest of girls in my class.

I forgot to add, soon after that I tried on my first bra, and never looked back.

[docrobbysherry]

I'm sorry, Katie. But, your entire theory is incorrect. Young boys, for the most part, don't crossdress. I know, because I was a male with no gender issues until I was about 50 years old.

So, why do vanilla boys and men not try on women's things? Probably for the same reason I didn't.

Because it never occurred to me!:heehee:

[Ginni]

I started to crossdress in preteens. It is something I just started to do. I knew that it was not acceptable and considered weird. I felt I had to do it. I never fully dressed until I was an adult. It is something I instinctively did. I believe there is a women in me and dressing is a way she gets out.

[Teresa]

Katie,
We are all different as you say.

Mine started by being attracted to wearing a shapely swimsuit at the age about 8-9 , it was purely sexual , the swimsuit represented a female body and something I knew nothing about drove me to put it on , I've told my full story in the TS section but the outcome was I experienced my first orgasm .Because of my age and not knowing what had happened and why it was more traumatic , but what I didn't realise was it tied all the parts together , my male needs, the female needs I was born with , the connection with clothing and sex . I believe that's when my GD started and looking back when AGP did . It left me with a gut feeling I've lived with the rest of my life , CDing thoughts 24/7 no wax and wane . I've finally come to terms with it, going out socially has helped me come to terms with my GD and AGP , I finally feel comfortable and natural being out dressed . I don't believe I'm a fetish dresser , there is far more to the equation than that .

Sherry,
I think you'll find there are more members here who started at a young age than later onset Cders , maybe you'd like to post a thread to ask that question assuming it hasn't been asked already .

[JenniferMBlack]

I started out of curiosity of what it was like to wear a skirt. At age 12 I finally put one on and was hooked. Don't think I would call it a fetish. It never went away. Pleasure is still the same just more of it.

[Lea]

I started crossdressing partially because of my mother. She wanted a son and a daughter but ended up with two sons. I became the substitute daughter. She used to dress me up as a girl and would not cut my hair. She has told me that people always thought I was a girl and she always smiled when she said it.
Then when I was older and it was time to go to school she had to treat me as a boy. I was raised with strict guidelines on how girls were supposed to be treated and behave vs, boys. So when I was no longer treated as a girl I was more to be seen and not heard and handle my own problems.
In my teens my parents worked second shift so I would dress when they were at work. Many times I would feel guilty about dressing and swear I would never dress again. Then the next week I was back to dressing.
It was a struggle as it was pre internet days and living in a small town I felt I was the only one dressing. Then one day I saw Phil Donahue with crossdressers that were married and happy, Other people who dressed wow.
During puberty almost everything gest you excited but I never felt it was a fetish.
Except for leave I stopped dressing while in the Military but started up again when I got out.
While my father was dying I took a picture of my daughter in a dress to his hospital room. When I asked him if he knew who it was he said yes it was me, his son in a dress. He confirmed that mom used to dress me up. Years latter my wife and I took mom out for Halloween with me being dressed and mom enjoyed it and had a good time, She did not admit to dressing me up as a girl but did say she really wanted a daughter and talked about how people used to think I was a girl.
I let my wife know about my dressing before we got married and she accepted it over time and helps with shopping. With her help I have accepted myself as a person I am. I don't feel I am crossdressing but just wearing my clothing and expressing who I am.

[Taylor186]

I started crossdressing at age eight or nine—mom’s stockings, girdle and swimsuits—and have a vague memory of trying to fashion a dress out of a towel as early as age six. Not sure why I started but I knew I liked it a lot. I also knew my buddies didn’t do it and I knew to keep it hidden from them and my family. I first dressed fully in my early thirties and didn’t even think of having a femme name until my late forties, and only then because of internet forums. While I felt a bit like an outsider compared to other boys growing up, I never felt like a women at any point, and still don’t, even when out and about fully dressed.

[Gillian Gigs]

It all started for me at the age of 4. For several years panties and girls clothes were a punishment for when I was being bad. This form of punishment stopped around 9 or 10. I started dressing on my own around the age of 12, I wanted to have the feel of wearing the nylon panties, which I vividly remembered. I would get dressed whenever I could get the chance, and I had plenty of chances. My sexual ignorance was huge and I had no idea what happened to me the first time I had an ejaculation while wearing lingerie. It took a couple of months until I heard a conversation in the boys locker room to realize what had happened to me. The desire to wear the clothes was greater than having to clean up any mess that now usually occurred. A new enjoyment grew and a fetish was born. Unfortunately there was now a strong need to get out of the of clothes once the deed was done. There has never been a period of time when it stopped, but there were times when it wasn't easy getting time to do anything. There were many triggers, but the biggest was probably stress and there seems to always be stress. Today the feelings of pleasure are very different than when I was a teen. I would be reasonable happy if there was less of a sexual component, so I could just enjoy myself without those's encumbrances.

[Princess Chantal]

It was definitely curiousity for me for when I put on my moms pantyhose. I was a leg hugger when I was young and always hugged legs when people were doing their good-byes. I was so fascinated with the silky feel of pantyhosed legs of the few women (mom and aunts) I leg hugged on rare occasions. My parents went to my father’s work’s Christmas party all done up in dressy clothing. Of course, my mom was wearing beige pantyhose to go with her dress that night. The following day I noticed them hanging on the shower curtain rod (drying from being washed I guess) and started fiddling with them as I was doing my business. It was a while before I even thought of putting them on and done so. About a minute or 2 of experiencing them on my legs, there was a knock on the door from dad asking if i was okay. So I slipped on my sweats and socks over top and went to watch tv. Not long after, my brother noticed me wearing them as we playfully wrestled and questioned about them. I showed him how cool the shade differs from my actual skin and how neat they feel compared to socks. I don’t recall him or anybody else shaming me for wearing them.
In my early teen years, seeing pantyhose on women (young or old, beautiful or not) always pleased my eyes probably thanks to experiencing that one childhood day. I did not sexually get off on them in those years, just admired people wearing them. However, I never put on the pantyhose or women clothing eventhough I had plenty chances at home. In my later teens and early adulthood (before crossdressing) I could say that pantyhose was a true sexual fetish. Was having dreams about being locked in a Sears or Hudson Bay store and trying the different pantyhose. I did not physically try on any women clothing until my girlfriend made me up for a Halloween. It was thanks to her researching that I came across a crossdressing social group on the internet that got me intrigued about crossdressing. I enjoyed being crossdressed and decided to take it up as an interest and get involved with socializing while doing it.
The early years of socializing with transgender folks, had me thinking that my crossdressing may be in fact something to do with GID or feminine expression like many others. I took to trying consecutive days of crossdressing and took advice on how to present more of a blend in appearance by not wearing pantyhose and other “women don’t wear anymore items”. After several months, I came to a conclusion that I was not enjoying it any more. I took on my crossdressing as an interest (hobby) and socializing activity without care of being seen as a crossdresser since and am enjoying my crossdressing to the fullest. Pantyhose on every crossdressing session is a must for me!

So to quickly recap probably my longest post ever,
first curiousity for pantyhose - non sexual adoration of seeing women wearing pantyhose - sexual fetish of pantyhose - coming upon and enjoying crossdressing - thoughts about gender stuffs - realization of being an activity for socializing purposes and hobbyish enjoyment.

[Asew]

My crossdressing didn't start until middle of puberty. It was definitely a fetish during puberity.

It stopped instantly when I went to college (threw out my stash since had no place to hide it since dorm roommates and only a few items left at home it could have easily been found).

It came back when my wife was out of the house several nights a week for about a years time. We were contemplating divorce and money was tight so it was definitely a stressful time.

At first it was more fetish but over time it was more like a comfort (such as just dressing and watching tv). Granted I am a simple dresser (skirt, bra, and shirt or a dress but no makeup or heels or nylons or wig) so it is pretty easy to put on be comfortable.

[Confucius]

Well, in my case I've been a crossdresser for as long as I can remember. Like others my mother wanted a girl when I was born. She already had a son and she hoped and prayed for a daughter when she got me. I was told that I was a very sensitive and clingy baby. Then when I was only six months old my mother found herself pregnant again. Was this going to be the daughter she hoped? So my sister was born when I was one year old, and my sister became my mother's pampered little princess. My mother would often recount how she prayed I would be a girl, and how my sister's birth was the happiest day of her life. How I wished I was born a girl! I knew my mother would love me more if I was a girl, and I would be pampered.

I grew up thinking that being a boy was a handicap. It was obvious that girls had it better in life than boys. I thought that all parents preferred daughters to sons because girls were nicer, smarter, prettier and never caused any trouble. I remember playing dress up with my mother's clothes and the funny thing about it was my next door neighbor (another boy) shared my interest in dressing in our mother's clothes. It got me in trouble because my mother feared we were ruining her clothes. At one point she made me a party dress, with a petticoat, and I loved it. However, my father objected, and my dress was given to a girl across the street. It also started a period of receiving negative feedback and warning every time I crossdressed. I knew crossdressing was supposed to be shameful, and I pretended that I agreed. When I started school I acted like all the other boys. However even then I thought that all boys were like me and just pretended not to like to wear girl's clothes.

I don't recall any time when there was no urge to crossdress, however I do remember that when puberty started, it changed my crossdressing. During puberty I would secretly try on some of my mom's old special occasion dresses, and when I did my whole body was shaking. I didn't understand what was happening.

I believe my early (pre-puberty) crossdressing was closely associated with gender dysphoria and a low self-esteem. It took me a long time to finally appreciate being a boy.

[MarinaTwelve200]

Its usually NORMAL in boys from about 2 to 4 or 5 years old---its some kind of stage they go through---Going to school, and facing ridicule or learning it just is NOT done, usually stops it. If it persists, especially publicly, then there is something else going on. There are many reasons older kids might do it--From identifying with the other gender, to something less complex like simply liking the feel of the fabric, or the BUZZ they might get from violating a social taboo. At puberty, sexual issues may further complicate things.---If they are doing it past age 7 or so, some counseling may be needed---and be careful who you consult.

[Stephanie Julianna]

I started at 4-5 years old. No sex in the early days until puberty which reared its ugly head. (Pun intended) Then diferent things about female clothes became sexually exciting by late teens and remain to this day, I'll be 69 next Tuesday. By age 30 I had an intense desire to dress to pass and that also still remains to this day. The pleasure that I get from dressing is derived from being recognized and accepted as female when out in the general public. It gives me a feeling of completeness. There were purges mostly in my teens and even one as late as 47. But I have come to embrace who I am and now only purge to make room for new stuff.

[ShelbyDawn]

I have no idea why I started. I remember as early as 5 or 6 wearing my mom slips because they were the closest I could get to wearing a dress that fit. As I got older, and as my younger sisters got older, I started borrowing dresses and underwear from them, especially their panties, and continued through high school. I'm pretty sure my mom knew but never said anything. At one point, with no conversation, all my tighty-whiteys disappeared from my drawer and were replaced with men's bikini briefs. Of course, I still borrowed from my sisters, they were just prettier. And there was/is just something intangible about them being "women's" clothes that matters.
When I got to college, I pretty much stopped because of lack of opportunity, not desire. Kinda hard to find private time in a dorm or with 5 roommates.
I did occasionally steal a pair of panties from a girlfriend or find a pair in the laundry(and once, I actually did find them) and would wear those. This lasted until about 15 years ago when my wife (now ex) started to get really abusive. I found relief and comfort in dressing and fortunately my ex was close enough to my size that I could borrow her stuff. It was kind of like finding that old favorite jacket or sweater in the back of the closet; something that had always been there, something that fits'just right' and has always been a source comfort that was yours again.
For me, dressing has never been sexual. I will admit to pleasuring myself while wearing panties while a teenager but at that point all it took was a light breeze to get me excited. Yeah, you remember that age, don't you? :)
I have done extensive counseling to deal with both the abusive relationship with my wife and my dressing and have come to the point that is just part of who I am and since it doesn't hurt anybody and it makes me feel better, there is nothing wrong with it. During the counseling, we actually did some past life regression stuff and I came across some very strong 'memories' of me as a young girl and then young lady. The feelings of completeness and of happiness associated with those memories is stronger than anything I have felt in this life. So maybe my soul is clinging on to those happy times and trying to recreate them.

Who knows.

Let us know what you figure out...

[jacques]

hello,
my dressing started when I was about 7 or 8 because I wanted to be like my hero Robin Hood who wore green tights!
Weird or what?
luv J

[NicoleScott]

Young boys know there are men's clothes and women's clothes. The first time we tried on anything feminine, we did it privately. We knew.

[Cherylgyno]

My parents announced that they were going out for a night the following week end. For the whole week allI could think was about putting on Mom's pantyhose and bodysuit. Time came my parents left instructions to call a neighbor before I went to bed. As soon as the car was out of sight I was in mom's dresser. Pantyhoseto then her red rib knit body suit. Something was missing. I unzipped the bodysuit, put on one of her bras (c cup) then ran to the kitchen and put grapefruits in my bra for boobage. I was feeling great, so great that I lost track of time. Mom and Dad were home. I quickly got into bed fully dressed. Mom came in checked the blanket and noticed the collar on the bodysuit, she felt under the covers and put her hand on my pantyhose legs, lifted the blanket a little and noticed that I had boobs. Nothing was said.
I fell to sleep knowing that I was caught, hoping I wasn't. A few hours later I had to go so I took off my girls clothes and went to the bathroom. I forgot about the clothes for a couple days. When I remembered I reached my hand under the bed and found bags of clothes similar but my size, bras were all C cup. I put the clothes back. A day or two later a dresser drawer was open. All of the clothes had been unwrapped and placed in my dresser. A note was on top that said that the clothes were mine. The guilty feeling was strong. Mom told me that we needed to have a serious talk before Dad got home the next day, I tried to avoid her. Mom caught me, I was fully expecting to hear it for wearing women's clothing. My mom repeatedly explained that the clothes were for me. I was to stay in my room when wearing the clothes. Now came what little lecture she had for me. She scolded me for having used my Dad's grapefruits for boobs. I was told never to take Dad's grapefruits from the fridge. For a few days I rolled up tshirts for boobs then Mom bought me a huge box of balloons to make boobs. I would get dressed every day and stay in my room. This went on for about 5 years.
I was 11 one evening mom informed me that dod wouldn't be home til late, we would eat dinner w/o him. Mom called me for dinner, I said that I had to get undressed. Mom said to throw pants and a t-shirt on and come to dinner. Mom saw my pantyhose under my shorts, she asked me to keep my legs under the table. Mom had me remove my t-shirt, she unzipped me and had me remove my boobs. We ate dinner mom told me to put my boobs back in my bra, she zipped me. I went back to my room. Dinners were like this when ever Dad worked late from then on.
Puberty hit like a ton of bricks. What simply felt good/right became a fetish of sorts. High school ended, I served my country. When state side I would buy clothes every liberty, get a motel room and stay dressed all weekend.
I got married, actually thinking that would "cure" my cross dressing. About 1 month after the wedding my wife caught me fully dressed and admiring myself in a full length mirror. I saw her reflection and panicked. Wife led me my hand to the edge of the bed. My wife was trying to talk to me about my dressing. I couldn't say anything. She decided to use 2 plans to get me to open up. She combined plan B with plan J. When she was done she made sure that everything was back in place. She remembered that a friend of hers was in the family room. She got her friend to leave and came to get me. I was getting undressed. Wife asked what I thought I was doing. I told her that I would purge everything. She read me the riot act telling me that she wouldn't allow me to. She helped me get everything done. She did my makeup for the first time ever. We went to the family room and talked the night away. She made sure that I understood that she wouldn't allow me to purge ever Here we are many years later, not 1 purge.
At 50 I was prescribed meds that gave me gynecomastia. I was blessed with D cup breasts. I now wear bra and panties every day. No way I could hide my breasts or my bra.
Is there blame to be handed out for me being a cross dresser? Hell no! Over the years I thanked my mom Many times for the way she handled my being a cross dresser. The only response s mom ever gave was Don't mention it. The latter years of her life she would answer Thank you for being the closest to a daughter.
I have left out others but I wanted to keep this a little shorter than War and Peace.

[Katie Russell]

Thank you all for your replies so far. It has made interesting reading. I have a few more questions:

1) If your crossdressing diminished after puberty what reason do you think the was? Was it girlfriends/wife/sex?
2) If you came back to crossdressing after a period of low/no activity was the feeling you get different? No longer sexual as it may have been during your teens?
3) If you came back to crossdressing do you feel that you now need to push boundaries. Where once it was a private issue you now feel the need to venture out and become more passable?

Katie

[Lacey New]

My crossdressing started in puberty. I guess I was fascinated by what girls had under their panties and putting on panties was my way of getting close to it. So it was a definite sexual fetish. From there, crossdressing sot of grew like a heroin addiction. Panties excited me, let's try panties and a bra - more excitement. Let's add a slip and pantyhose, etc, etc. So more feminine clothing became more fun and more exciting. And while now, I can wear panties, bra, etc for hours, there is still some excitement in shopping and buying, trying and wearing women's clothing. I don't think the sexual component of my crossdressing will ever disappear entirely.

[Beverley Sims]

Curiosity killed the cat.

Yep!
I played the part of the cat, like so many others.

[Rhonda Jean]

I have no idea why, except that it was just fun!

The clothes hamper was in our only bathroom. From my very earliest memories I'd go through the clothes hamper and find things to try on. I'd stand on the toilet so I could see myself in the medicine cabinet mirror. I don't remember having a penchant for any particular thing except full slips, because on me I thought they looked like an evening gown. I had long hair and I'd mess with my hair or pull it over one shoulder and just admire myself in the mirror. It wasn't sexual. I was way too young for that. I just liked pretending to be a "beautiful" woman.

I guess for some little boys a sports uniform excites their imagination. I think it was the same kind of thing for me, except with a different uniform.

[Allison Chaynes]

For me, I never did anything until age 12, when I was at a friend's house and his mom had just done laundry, leaving a basket of clothes sitting out overnight. I suddenly got this weird urge to wear her panties, and a fetish was born. It stated simply a panty fetish for years, then about 7 years after getting married, I realized other women's clothing was wonderful too. It's no longer just a sexual thing, in fact I wear women's jeans almost daily.

[Katie Russell]

I think that there is a trend among crossdressers. There will always be outliers who don't fit the norm but there does seem to be a vanilla pathway if you like.

I started young. I can remember swapping clothes with my sister for fun. I enjoyed it. Then one day saw some of my mum's lingerie ad had a desire to try it on. From that day on I was hooked. Don't know why I wanted to try it on just did. Curiosity maybe.

Anyway fast forward to puberty and any chance to put on knickers. They had to be a specific type, nice silky material, but it always had the same result. My fetish stage.

I then discovered girls and the desire and opportunities to crossdress waned. I guess I got my sexual needs satisfied elsewhere and so the need to crossdress.

Then life became settle, kids, job and stress. One day just decided to buy myself some lingerie, skirt and top. First time I'd owned any clothes of my own. Mid 30's.

From there on it developed. More clothes, make up , wig forms etc. I now have a desire to venture out. It is no longer sexual but relaxing, de-stressing.

Reading through the posts this seems pretty typical.

I do have a theory as to why we follow this pathway but want to do some more reading. I've just started a book which resonates so want to get to the end to understand if it all makes sense.

Katie

[Stephanie47]

I cannot remember the exact age I started dabbling in my mother's unmentionables. In our apartment the bedrooms were down a long hallway. My mother hanged clothes to dry after washing them on a clothesline which went down the hall. To get to the bedrooms I had to actually negotiate my way through the hanging laundry. That included her nylon white slips. I found the nylon was unlike any of my boy clothes. I loved the feel of the nylon. I would caress the slips. Finally I took one down and slipped into it in the bathroom. I had to feelings to be a girl. I did not have any sisters at the time. My mother did not dress me up as a girl. All my cousins were boys. All my playmates were boys. Later I progressed to trying on one of her floor length nylon nighties. There was nothing sexually stimulating at that time. Televisions shows were asexual. I did not have access to Playboy. I really did not think about sex. In junior high school if I thought a girl was cute it was not in a sexual way.

I think when puberty came along that led to self satisfying actions and wearing my mother's clothing was an enhancement. Of course, this desire to wear women's clothing conflicted with the male sterotype behavior expected of young males. This produced a lot inner turmoil. Basically, society in the 1950's and 1960's ascribed 'gayness' to men who wore women's clothing. Was I gay? I did not know what gayness meant.

Yes, there was a period of time I had absolutely zero interest in wearing women's clothing. That started in my late teens and early twenties, especially when I was in the military. There was no opportunity living in a totally barracks environment. But, I had no desires. Yes, I drooled over young women entertainers like any other guy. In Nam one had other things to hold one's interest....like staying alive.

It wasn't until after I married and I was drawn again to nylon. My wife was a drop dead gorgeous young woman (still so after almost 50 years) who wore slinky nighties. There ended up some 'bedroom play.' On occasion I wore a nightgown that was too big for her. Finally, we ended up buying several in my size. That kindled the desires for more. The fun stopped when we both discovered this way more than 'fetish sex.' We ended up in Don't Ask, Don't Tell. I always wonder if she had not been turned off by the prospect of living with a man wanting to wear women's nighties for reasons other than 'fetish sex,' if I would have just remained a 'fetish sex' guy. Now? It's a vast array of dresses, undergarments, hosiery and heels. Is it pleasurable? Not in any sexual satisfying sense. It just feels natural to wear women's clothing when the inner Stephanie calls.

[ChubbyLeahCD]

Katie,

That’s a good topic and I don’t think I’ve ever wanted to be a girl, still don’t. I want to live in that gray area where I can have my body prepped in a way that I can go either gender.

So here’s my story:
The first time I recall being mesmerized by anything female, I wasn’t maybe 5 and the pre-school owner was standing talking to someone and she had a shirt, skirt and t-strap sandals. She had her hands on her hips, legs apart and one foot in front of the other.
I remember standing there and trying to copy her pose and also wanting sandals like hers.
At the same school, the girls did ballet and I wanted a leotard for me, blue but I did want one.
My grandma was one of those ladies that would rinse her panties in the shower and let them dry and then wash them with the laundry. So whenever I would go spend the night I’d wear her granny panties in the shower.
As I got older I didn’t venture out much but would see articles of clothes that my mom had or other women and I’d wonder how it would feel to wear it.
In puberty, middle school, as I got more freedom and got to stay alone st home a lot, I started raising my mom’s closet.
I would memorize where things went and I would try them on. I didn’t know what it was but as I got older and got to college and I thought that was a fetish.
In college I used to go to a website where regular women would have their own amateur site and one of them sold her clothes and stuff. I got my very own first clothes from her. I would always feel guilt and shame afterwards.
That led to my downfall so to speak (I won’t get to it as I’ve already said that in my intro) but it took counseling for me to realize that while there is sexual excitement of me wearing women’s clothes, there’s also a lot of non-sexual pleasure and excitement. I realized that I’m gender fluid or bi-gender. I like male and female things. Gender roles shouldn’t apply to me.
Leah is part of me and I hope one day to be able to get her out.

[ginapoodle]

Very interesting to hear these stories. I fit the typical profile. In middle school I always wanted to be a girl--jr high stress was incredible. There is part of me that believes life is just better as female--

Lack of male role models early in life may have had a factor?

No idea why I tried that first pair of nylons at age 12.

I have had periods of many months with zero interest or dressing. I have also had periods of intense dressing activity and high gender dysphoria.

Thanks to all.

[Pumped]

I remember finding my mom's bra and stockings when I was 6-7 years old and locking my bedroom door and putting them on. Of course everything was too large but I loved it. I would stuff the bra and have HUGE boobs and stretch a t-shirt over the top. I remember getting a feeling in my groin but don't remember getting an erection or for that matter I didn't realize I had a penis until puberty. To this day I love big boobs, bras and nylons, stay ups, garter belt and stockings, panty hose are all fair game. It has been a fetish for me since puberty hit.

[StephanieCLT]

Young girls do it, too, but for them, it’s called “dressing.”

[RADER]

I remember trying on my mom's girdle when I was about 5 or 6 years old.
And My mom catching my stash of girdles I hid under the mattress; I was about 8 then.
I made a hidden compartment under the bottom dresses drawer. I hid about 5 diferent
girdles and long line Bra's.
Rader

[Georgina]

I don't really know why and I am not all that worried but I am glad they do. They have as much right to do so as young girls.

[JaniceP]

I was 5 when my mother caught me trying one of half slips. Didn't know what a fetish was, I just saw Girls wearing cute dresses with petticoats and wanted so much to look just as pretty as them.
I would go to bed at night thinking of a scenario where I would be put into a Girly machine, all my boy clothes would be taken off and I would emerge totally, from skin out, dressed in the most Feminine, prettiest, petticoated Pink ruffled Dress anyone had ever seen.

That's how it Started. Purged often as I got older< but my desire to dress totally always came back with a vengeance & the older I get the more I want to wear pretty skirts/blouses, frilly Dresses, Padded hip and butt control panties, lacy pastel colored Bra with a matching Long Leg Lace trimmed PantyGirdle with Garters to hold my sheer Stockings.:daydreaming:

[Marihanne]

My first time crossdressing is too much orgasm, just wear a bra on in any suit (even boy's suit), I am forced to say "OH MY GOD, WHAT IS THIS FEELING" *fap fap fap fap fap* ( sorry, I said I'm pervert)

If I can be reborn, I will crossdress as soon as I can :D

[NicoleScott]

I remember getting a feeling in my groin but don't remember getting an erection or for that matter I didn't realize I had a penis until puberty. To this day I love big boobs, bras and nylons, stay ups, garter belt and stockings, panty hose are all fair game. It has been a fetish for me since puberty hit.

I remember as a boy (5-6 years old) being attracted to pretty women wearing high heels and heavy makeup, particularly deep red lipstick. Face-down on my bed at night and recalling these images, I got that feeling, and rubbing myself against the bed felt good. Then one time as a preteen/young teen, the first Big O happened. It was a game-changer.
I believe I had sexual experiences long before puberty, even not understanding what was happening and not being fully functional. But what I felt was a sexual response to those women's things that excited me. I think my fetishes began very young but only reached a peak after puberty. In some ways, long after puberty, as I learned through fetishistic crossdressing how to maximize pleasure.

[Jenny22]

As a young boy I was always disappointed by how plain my best boy clothes looked compared to the beautiful clothing (dresses, then) my two older sisters could and did wear. It wasn't fair! I once told my mom that I wanted to be as prettily clothed as my sisters, and she told me to forget about it! You are a boy! I often prayed at night that I could be a girl in the morning. My desires became an obsession. The clothes hamper in the bathroom became my source of the pretties I needed, and I explored same whenever I could.
I really believe that every boy has thought about or did try on some female clothing or underwear, if it was easily done, simply due to curiosity. After that, only the Shadow knows!

[HollyGreene]

When I was about 3 years old, the only other children I had ever met were boys. Then a family with a young girl moved into the street. I can remember being mesmerized by her. She was so pretty and wore pretty dresses. From that time I wished I was like her. I didn't know what the physical difference between girls and boys was until my sister was born later that year. It was several years later that I found that I could fit in some of my sister's clothes, which I did in secret as often as I could. When she reached her teens, my mother bought her some lacy, nylon knickers - the first pair she owned that weren't for 'kids'. But she hated them so pushed them to the back of her underwear drawer never to be worn again. Or so she thought, because I wore them on a regular basis throughout my teenage years, washing them by hand and returning them to the back of the drawer.
So for me, it all started in my head having seen that pretty girl for the first time, and then the wearing of clothes started as a teenager. Going to university was a turning point as I was able to get some of my own female clothes and spend time wearing them while locked in my room.

[ShyLibrarian]

My first time crossdressing is too much orgasm, just wear a bra on in any suit (even boy's suit), I am forced to say "OH MY GOD, WHAT IS THIS FEELING" *fap fap fap fap fap* ( sorry, I said I'm pervert)

If I can be reborn, I will crossdress as soon as I can :D

(laughs) I'm sure you're not bad at all. Your experience is quite common as far as I know. Good luck with your adventures!

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I don't really know why and I am not all that worried but I am glad they do. They have as much right to do so as young girls.

Wish I'd met you when I lived in Northern Ireland (a place that's too cold to spend much time cavortng in the garden in stockings and sussies). Like you, Georgina, I don't agonise about why I adore lingerie all about me, but just get on with it. Most of my g/friends have been fine with my cross-dressing (though YOU do it so much better than I do, Georgina) with some actively joining in my dressing me in bits of their frillies:)

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I started at 4-5 years old. No sex in the early days until puberty which reared its ugly head. (Pun intended) Then diferent things about female clothes became sexually exciting by late teens and remain to this day, I'll be 69 next Tuesday. By age 30 I had an intense desire to dress to pass and that also still remains to this day. The pleasure that I get from dressing is derived from being recognized and accepted as female when out in the general public. It gives me a feeling of completeness. There were purges mostly in my teens and even one as late as 47. But I have come to embrace who I am and now only purge to make room for new stuff.

Excellent post, Stephanie. I was relatively unaware of women's lingerie until puberty and, even then, didn't do much about it except occasionally put on panties with a male friend over at his house. However, in my late thirties when I was in the process of divorce it flared up very strongly and I started slipping into my wife's undies and - for the first time - buying my own panties, camiknickers, and even half slips.

I now live alone, in eastern Canada, just north of NY state, since my girlfriend passed away last year. She was very supportive of my cross dressing and from time to time would go shopping with me or let me have panties from her own collection. On occasion we wore his and her dresses. Since I have an acre of land I can go outside the house (in summer), just dressed in camisole and frilly panties but I am exposed to passing traffic for the first 10 yards or so, lol, so sometimes get a frisson of fear. The local rednecks are harmless (because obviously we don't carry guns here), but they are experts at ridicule. Since I haven't been caught yet, I haven't been the actual target of it:)

The most difficult part, I think, is not having one or more male (or, indeed, female) friends to chat with about cross dressing, whether in person, on the phone or in email. One of my male friends is very into it but trying to give it up, while another is married to a non-approving wife so no discussion - even in email - takes place, except on rare occasions when we meet outside the home.

Living in the country means one is always somewhat far from friends and acquaintances, rather than bumping into them on a daily basis.

I admire your courage and commitment in going out and about, dressed.