How did you start and where are you at now?

[Jennifer2918]

Hello to all,

New to this site, but lerking for a long time just reading and getting more support than you realize.

To give you some perspective, I am nearly 55 years old.

I know there are other threads on this subject, but most seemed older; so I wanted to start a fresh one.

Anyways, I remember when I was7-9 years old and found a pair of my mothers pantyhose drying in the shower. I tried them on, ruining them of course as I did not know how to put them on correctly. I remember trying to put them on like a pair of pants, not good. I figured out how to put them on correctly rather quickly, and would do so every chance I got.

Then came high school and my pantyhose thing died down. At a high school halloween party, my girlfriend dressed me in her cheer leading outfit and I was in heaven all night. Then came college and joining the work force with little to no activity.

Then suddenly, about 20 years ago, it all came flooding back. It started by wearing the wife lingerie when home alone. Then, I became more daring and would wear it out under drab clothing, occasionally letting myself get caught by strangers.

About 10 years ago, I asked the wife if I could try on her used panties, which she agreed to. This lead to our purchasing of a few pair of panties for me. Then, one time shopping at a local thrift store, I picked up a pair of pantyhose and found they were a size that would fit. I showed them to her and her comment was, 'if you want them...' and into the cart they went.

Now, she is aware I enjoy crossdressing, but does know what I have as a wardrobe. On a day off of work where she had to work, I called her and asked if she minded if I went to a Good Will store in a neighboring community. She said go ahead.

At the store, I found a couple of skirts and dresses. The SA was very helpful and pleasant. I brought them home, but only had a small compartment to keep them in (out of sight, out of her mind).

This wardrobe has grown lightly over time (been purged once, but re-stocked later). She now has allowed me to hang my dresses (6) in the far end of my closet, allowing me more room in the compartment for additional clothing items.

We have an arrangement which allows me to go out one night a week (usually very early Sunday morning), for an hour or so, to do my 'running' around. She knows that I am dressing, but have to leave the house in drab mode and cannot change until away from home. I have asked her if she wants to come with me to see exactly what I am doing, but she has always declined. When I have asked if she has any questions, she says no and changes the subject. She has seen me dressed in womens pants, exercise shorts, and pantyhose, but nothing more than that.

I am hopeful that someday she will be more open for this and accompany me on an outing.

[Kendalli]

For me it started when I was 12 or 13. I was curious what panties felt like, so I snuck into the parents room and tried some on. That quickly led to me trying anything and everything she owned on. Heaven. In college things slowed down as I did not want to be outted but picked up shortly after.

Now I'm out to the wife. She has some major trepidations about all of it, but she is willing to let me explore where this will go. She has seen me in a few things and has been supportive so far, but trying to take it slow for her since this has been such a shock to her.

[alwayshave]

Jennifer, probably not an uncommon story about how you started. I'm glad your wife understands even if she does not want to see it. Started at 4 or 5 and now I have an accepting partner and go out dressed, she comes along.

[Elizabeth G]

I was about 11 or so when I started. I was at that age where interest in the fairer sex was beginning and so I found myself checking out the lingerie section of the Sears catalog (that's about as racy as it got around my house when I was a kid). Very quickly I realized I was was becoming just as fascinated with what the models were wearing as I was with the models themselves and the exploration began from there. I've been dressing sporadically ever since, although it seems to have become more of a permanent thing now. It began all those decades ago with mostly just lingerie but now I have a pretty full wardrobe and enjoy getting out fully en femme on the all too rare chances that I get to do so.

[Sabrina.K]

From about 14 or so, I constantly fantasised about trying on dresses. Mostly certain kinds, like maid uniforms and chinese-style dresses.

It wasn't until I got my first job at 17 when I could finally buy some stuff . I started with a black knee-length chinese dress. I spent many hours sat at my computer in it (With a wedge under my door in case a family member tried to burst in lol).

So I've been doing the same thing on and off since then. Other than cosplaying for fun, I've not gone out dressed, which I really hope to one day do.

[BillieS]

I started when I was 7 or 8, lured by my mother's shapewear! But I dressed only occasionally during my childhood and never as an adult until about 20 years ago. That's when my wife urged me to put on some makeup and, well, one thing led to another. I've been a dedicated dresser since then, tho with waxing and waning periods. This is a major waxing period now.

[Jean 103]

Thank you for sharing. I'm sure you know if you have been here very long, that the level of acceptance you enjoy is good. She must be very special.

There were signs but I really only started dressing a few years ago. My wife is not understanding at all. We've been separated for about three years.

I live openly as a transgender person. I represent as male at work. The rest of the time I'm Jean. I'm on my third roommate situation, all have been very understanding. I don't know where the road leads from here, but for now I'm in a good place.

[Jaylyn]

I suppose I started at birth. Mom just knew she was having a girl baby so much that she sewed out of flour sacks gowns and several little dresses for me. I used to have several baby pictures all black n white and small, of me dressed in the frill dress she made. She let me play in her stuff and even dabbed red lipstick on me even painted my toes nails n finger nails once. Dad put a stop to it and cut my curly locks off around three or four years of age. I dabbled in her stuff as a teen off and on. Then quit during high school and college. It came roaring back though after I married and my wife left her things out and we had a discussion about me enjoying wearing women's clothes she said she thought I loved makeup as I always wanted to to put more on. It has grown to now I have my own panties and a chest full of things I enjoy wearing. I had to promise the wife I'd never Embarrass or wear the things out in public. She has helped dress me many time teaching me makeup skills and such. She one day recently just quit liking it so much as to put me in a DADT type situation. So that's my story pretty much.

[NancySue]

As I recall, around 6-7, I was invited to join our next door sisters in their game of “dress up�. I didn’t see much fun in it until they suggested I try on a pair of pantyhose. I had no clue how to put them on, so they helped me. It was like a lightning bolt. I remembered it to this day. I couldn’t wait to go “exploring� in my Moms and sisters things. I’m pretty sure my sister knew what I was doing, but never said anything. Fast forward. I continued. I told my wife before the “I do’s�, thinking she’d run, but she didn’t. After many long talks, reading, patience, etc., she’s not only accepted my dressing, but also is supportive, especially with makeup. Priceless. I have my own complete wardrobe and freedom to dress whenever and whatever I want...but I never seem to have enough pantyhose or thigh highs. Lol. I usually wear underneath Monday to Friday, then dress more on weekends. We live in a smaller town, which inhibits going out, but I/we venture out of town occasionally.

[Sarah Doepner]

I had plenty of feelings I didn't understand and couldn't match up with the clothes as early as 6 or 7. By middle school I was starting to understand and began wearing my mothers things and that continued for a few years until I outgrew her things. During the last of high school, college and early career I was an opportunity dresser and didn't get the opportunity very often but it picked up as I began trying a few of my wife's things on. Eventually I got more and more of my own things, was caught by her, was told after a few days she would support me and I began getting more of my own things. I started going out, usually when out of town or very late at night. Eventually I joined a local support group and although my wife was fighting cancer, she went to meetings with me and when in Las Vegas we went out together as well. After she passed away my closet continued to fill and now I'm out to my grown children, a few other family members and a friend or two. I've seen a counselor and seriously consider the possibilities of seeing if hormones would help me quiet my mind. I may never fully transition but given the distance I've traveled I'll never say never. The limiting factor may end up being the number of years I have left to walk around rather than what I expect and plan for.

[DIANEF]

I was about 10-11 when I started with my sisters undies and swimming costumes, first dress at 15 and been doing it ever since. In terms of age I'm just a year or so behind you Jennifer, and welcome to the forum.

[Leann_M]

When I was 15 a friend of mine brought over a movie that had a crossdressing scene in it. My parents weren't home so after the movie we went in my moms lingerie drawer and put a couple of slips on over our clothes as a joke. After my friend went home I was curious so I stripped down and THEN pit on the slip. The feel of the material was wonderful and I liked how femine it made me feel. I've been hooked ever since.

[Stephanie47]

I don't remember exactly how old I was when the allure of women's clothing hit me. I know it was my mother's nylon slips. My family lived in an apartment. We had a washing machine, but, no dryer. My mother hanged the laundry to dry on a clothesline running down the hallway to the bedrooms and in the bathroom on a drying rack suspended from the ceiling over the bathtub. I loved the feel of the nylon slips. At first I would just fondle them in the hallway. After a while I decided to try one on in the bathroom. I loved the feel of nylon. It was unlike any of the little boy clothes I wore. I had no sexual motivations at that early age. I had no sisters or female cousins. I had no female playmates. It was purely the nylon. Later I tried on my mother's floor length nylon nightgowns. I guess those articles of clothing hooked me. I think it was entering puberty that my interests expanded into wearing my mother's girdles, stockings, bras and panties.

Why did this start? I wish I knew. I have some thoughts about it, but, it is sheer conjecture.

[sometimes_miss]

It started when I was molested and dressed up as a girl for someone else's pleasure; it all started right after first grade. It continued because he convinced me that god had made a mistake, and that I was supposed to have been born a girl. It goes on to this day, I'm guessing, because for all that time, I really believed that I was supposed to be a girl, and was waiting throughout my adolescence for god to fix me, and perhaps due to that belief all through that stage of development, the feeling remains; I'm stuck feeling like a girl on the edge of puberty, waiting for my body to develop as a woman. As this feeling has been with me now for nearly 50 years, I guess I'm permanently stuck feeling like I'm supposed to be dressed as a girl basically all the time. Once I figured out that I wasn't gay or transsexual, I sort of wondered why I still felt the draw towards girl clothes and behaviors; our mental health professionals give us the subtle implication that if we only work through all out problems and discover why we feel the way we do, we'll somehow be 'cured'. Nope, doesn't work that way. Turns out the best we can hope for is to be able to understand it all, and be able to cope with it a little better. So anyone hoping for a cure will be pretty disappointed.
Anyway, it's not a crippling problem, as when I'm busy with work or something the desire to dress up as a girl isn't always up front and on my mind, but it's always there, lurking in my subconscious, waiting to come front and center once again. I can consciously suppress it, but after a time, I become irritable and short tempered. So, I dress up when I can, to keep the tension from building up.

So, where am I? I'm a closeted crossdresser. When I discovered just how rare it was to find a woman who would accept this in a man, I really had no choice. It was stay closeted or be alone all the time. The choice was a no brainer. Oh, I date, but I don't tell the women that I crossdress. I gradually ask them things regarding crossdressing, and see if there's any chance they might be accepting of it. So far, in 19 years, nope, not a single woman would be accepting of this. So I simply stay closeted, and enjoy what time I have with them until the 'where is this relationship going' conversation comes around, and then I wind up breaking it off. OH well. Better to have loved and lost, than to never have loved, at all.

[Ceera]

I have early memories of trying on some of my mom's slips, panties, bra and girdle as a kid. My bedroom was in the basement after I was bout seven years old, and that was where the laundry room was too. So it wasn't hard to examine laundry that had been left to run late the night before - or to run the dryer for a few minutes to warm up the clothes in it. Nothing really fit me, but I did like the way her slips felt against my bare skin - especially when they were warm from the dryer. Never tried to keep anything, and always returned the items to the laundry after a few minutes.

About the same age, 10 or so, I recall playing with moms lipstick a few times. It was fun seeing myself with it on, but I was lousy at applying it! Always washed it off again right away, and put the borrowed lipstick back.

By my teens I knew I was bi, but also knew my dad wouldn't accept that. So I spent a large part of my life in denial of my feminine urges. Married a nice girl and tried to 'play it straight'. She knew I was bi, but also knew I had agreed to be monogamous and only mate with her. My only 'feminine expression' for many years was that when playing games where I could pick my character's gender, I would, as often as not, choose a female character. Got so good at role-playing women that my on-line gamer friends believed my female characters were being played by a real-life gamer girl. I also wrote some erotic fiction that featured bisexual or cross-dressing or transgender characters.

Fast forward to 2012. A month or so before my 56th birthday, my father died. My mom had died the year before. While I was back in my home town to attend my dad's funeral, I decided that since I no longer had to worry about my parents 'finding out' my inclinations, I would at least try buying some panties and a corset to wear in private, to see how it felt. I brought them home with me, and hid them in a gym bag. After a month or so I had added a cheap wig, some panty hose, a blouse, a skirt and a heavily padded bra to my 'secret stash'. But I only wore them at home, when alone. Still had a full beard, and wasn't about to go outside and be seen, or even to admit to my wife that I was doing this much.

By 2013, I had switched to under-dressing with panties full-time, and my wife and daughter knew and accepted that I was wearing panties under my male clothes. I used the excuse that I preferred the bikini style briefs, but that they only sold them for women... Still pretty much doubted I would ever go outside while dressed...

Then at the start of 2014 I lost my wife to a heart attack. 57 years old and a widower, I decided to come out to my 18 year old daughter, and admit that I wanted to shave off the beard and try to explore the feminine urges I had been suppressing all my life. I already knew she had several gay and lesbian friends in her high school, and even had one high school friend who was going through MtF transition, living full time as a female, and accepted by my daughter and their school friends! She was 100% supportive. Even started going out shopping with me for women's clothes! I did not yet know if I was a bi crossdresser or actually transgender, but I was determined to find out!

By the end of 2015, I had been going out publicly as Ceera for a year and a half, going out several times per week. 75% of my social time was en-femme. I could pass for female even in a bikini! I had more friends who knew me solely as a woman than I had ever had as a male. Most of my new social friends were lesbians, who accepted me as part of their circle of friends. Most of my clothes and shoes were female. I knew by then that I was transgender, bisexual but still primarily attracted to women. That made me mostly lesbian while out en-femme. We moved to Oregon, where I live now, and I decided that in our new home, our new friends and neighbors would know me as both my male and female sides - that I would live openly as a trans-woman early in her transition.

And that is where I stand now. 95% of my social time is en-femme. 90% or better of my wardrobe is female. And it is likely that next year, I'll change the gender marker on my driver's license, birth certificate and other legal papers to female!

[Rayleen]

Where do I start ?

In the 70's after married, So worked during the day, I worked nights. So my mind was trained by previous teens habit
of trying on garter belts with nylon, very addictive. shopping for panty ,bra .

As I was alone before our daughter arrived, I had started to explore my wife's clothing such as hot pants in the 70's
I tried a pair which she had put aside and wow did give me the chills.I had quite a few dressing session but was not out yet
to my wife.

The came summer and the beach. I wanted to try sunbathing in Buff. First attempt was in a wood lot I had and went alone one afternoon
It was amazing how the air was caressing every part of my body. So we have a 6 mile sand bar not far and its classified as visitors
friendly to walk and bathe in the nude. I went alone, SO was not wanting to come because of her family and religious belief .
This was great for a part of the summer and it was something I wanted to do for a long time. never done it after .

After the kid arrived, came responsibility and things cooled off quite a bit, with less occasion to practice my favorite hobby CD.

Only after she was gone from the house, I resumed acquiring stuff and learning a few technique of the trade. I knew I could not go on without coming out to SO and I did and slowly she tolerated me and she kind of liked it,cause I went shopping and she liked my
choices of clothing for her and told her stuff I liked and was very cooperative helping me. We always have a good communication
which is the success in being accepted .

[StephanieM]

For me it started as a dream, my grandmother had dressed me up in bra and panties, and when I woke all of a sudden I had an interest. The weird part is she had dressed my dad up as a girl when he was a small boy which caused him to become a CD. I had no idea of this until many years later.

[Alice B]

First of all, Welcome to this site. You will make friends here. The fact that your wife knows and has not screamed at you and allows you some freedom is a good thing. If your marriage is strong then with time she wil become more accepting. Be patient and don't push it. My wife does not wanty to participate in any fashion, but allows me to dress and go out. She has seen me fully dressed and just looks away. No screaamimg etc. I did not start until my 60's and never had any of the adventures you had in your earlier years

[Cassie38]

Like most, I remember first trying on my mother's clothing when I was young, probably around 7 or 8. That continued into my teens. I stopped in college, but was reintroduced to this world while I was in grad school by my girlfriend at the time. She suggested I crossdress because she loved my long hair. She even went out and picked up a few things at thrift stores for me. She helped me with my hair, makeup, and shaving (I have hairy legs, chest, stomach). I have to admit, she made me passable. Sadly, the photos she did take of me were on 35mm (this was early 00s when digital camera weren't mainstream too much). Sadly, those photos have been lost over the years.

[Becky Blue]

Well for me it started at age of 4 or 5 where I started a game I called 'pretend I am a girl' I even had my girl name Karen (An older cousin - clearly limited imagination in those days lol). I asked my mother to out a ribbon in my hair. I played the game on and off for about 3 years.. just one of quite a few games I played. I often wonder what would have happened if I had a sister, I am fairly certain I would have been trying on her clothes. I stopped playing the game when we moved cities when i was 8. At no stage can I recall wanting to actually be a girl.

Then at 12 I discovered how much of a turn on putting on items of female clothing could be... That phase lasted uuuuhhhh over 25 years before Becky emerged and the fetishtic hobby went away.

[sara66]

I was 4 or 5 putting on mom's bras. Today I am fully dressed and going out in the real world.
Sara

[binni101]

Since I can remember it started with pantyhose. The farthest I have gone in under dressing is pantys and hoisery to the local store. The farthest in dressing is underwear, hoisery, heels, dress and lipstick. Im a "closet case" in my crossdressing so I have not gone into makeup :/

[Beverley Sims]

Started about four until today about 90 percent of the time.

[ChubbyLeahCD]

Funny that the OP mentioned pantyhose drying in the shower. For me it was my grandma’s panties drying in the shower.
Remember as a child, 5 or 6, Seeing a pre-school teacher standing with hands on her hips, feet spread out and t-strap sandals and aÃ* wanted those sandals.
As middle school started I got more alone at home time and I raided my mom’s clothes every time.
When I moved out of my dorm and had my own apartment, I would go in my bedroom and dress. My roommates had no idea. My first outfits came from an amateur porn website where the lady sold her clothes worn on photo shots.
Now I have a hidden stash, wear it alone at home or when traveling for work and the wife doesn’t know :-(

[Confucius]

I don't recall a time when I wasn't interested in crossdressing. My mother wanted a daughter so my birth was a disappointment for her. When I was only six months old she because pregnant with my sister. When she was born it was the happiest day of my mom's life. My sister grew up as my mother's pampered little princess, and I grew up thinking that my mother would love me more if I was born a girl. I thought that all parents preferred girls and that girls were better than boys. By the time I was 3 years old I was already raiding my mom's closet and pretending I was a girl.