Why do young boys crossdress?

[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.

[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

[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

(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!

[SIZE=1]- - - Updated - - -[/SIZE]

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

[SIZE=1]- - - Updated - - -[/SIZE]

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.