How did you start down this road?

[cdinmd206]

Ever since I can remember I had a love of lingerie. When I was 7 or 8 the girl who lives across the street had a birthday party and one of her gifts was a package of nylon panties with the days of the week on them. I was admiring them and my mom asked if I liked them and I said yes. She then asked if I would wear them and I again said yes. Two days later she gave me my own day of the week panties. Unfortunately when my dad found out and that was the end of my panties plus a sore back end.

About a year later I was spending some time with an aunt who always wore a dress with stockings and heels. As I walked by her bedroom, the door was slightly open, and I peaked in. OMG I will never forget the sight of her removing her dress and slip. Underneath she had on white see thru frilly panties, white garter belt and a very lacy bra. Later that day I went into her bedroom and was looking thru her Chester drawers checking out her lingerie. I was holding a pair of her frilly panties when she walked in. I just knew she was going to whip my butt and tell my parents. She calmly told me to put her panties away and then asked why I was in her bedroom. I told her I had seen her changing clothes earlier and was fascinated by her lingerie. She told me it was wrong to go snooping around like that and to not do it again and she would not tell my parents.

About a month later my aunt asked my parents if I could spend the weekend with her to help with some yard work. I was dropped off Friday evening and Saturday I spent all day doing yard work. That evening my aunt told me take bath and when I walked into the bedroom in my robe my aunt was sitting on the bed and on the bed was some lingerie. My aunt said these are for you to wear inside my house and it will be our secret. I turned my back and slid on a pair of nylon panties. When I turned around my aunt was holding a training bra ad she fastened it on me. She then hooked the garter belt on me and when she slid those stockings up my leg and attached the garters to the stockings, I knew I was hooked on the feeling. She also bought me a very frilly dress. She said now you are my niece not my nephew and again it is our secret.

Up until I was 16 I would spend many summer days at her house. My parents thought it was a great idea to be helping my poor widowed aunt with all the yard work and upkeep to her house!!!!!

[GraceH]

My second grade teacher used to punish boys for misbehavior by making them wear a headscarf for the rest of the day, including outdoors at recess. I never received that punishment, but wanted to. So, one day, age 7, I put on one of my mom's scarves and headed out into the back yard, where I was seen by a neighbor. I never heard anything more about that, and it didn't daunt my curious explorations into my mom's stuff. The first time I put on lipstick, still age 7, I recall a huge rush of excitement, carried away by the feel, the fragrance and the appearance. I regularly wore her skirts and bras, and wasn't caught as far as I know. I know my dad would have violently disapproved, so I had to keep it hidden. After college, I acquired a full wardrobe, and except for a couple of purges that didn't last long, I've been dressing regularly ever since, 70 years total from that 2nd grade exploration.

[SaraLin]

I've always - ALWAYS knows I should have been a girl, so I took every chance I got to try to look the part.

Even as young as 4-5, I'd sneak something of my sister's to wear in secret. I also raided my grandmother's attic for some old outfits I found in boxes up there. I "liberated" some of these and took them to my "hideout" in the woods out back of our house.

But unlike so many others, I was less fascinated by the underthings. I wanted to LOOK like a girl and that meant that the outer things were what was important to me. Dresses, skirts, and tops were my thing. Panties and slips soon followed, simply because it was what a girl was supposed to be wearing underneath. It was only as I got older and the girls my age started developing their figures that I started thinking I needed to wear bras. Again, it was more to achieve the look (boobs) than any erotic element. Hose, girdles, etc. - same story.

[Giselle(Oshawa)]

Around age 10 or 11 yrs old, my parents were out and i went through my mothers lingerie door.
Before I knew it i had on one of her bra's, an obg(girdle) and nylons.
I did this for probably 2 or 3 months and I am certain my mother suspected.
She bought me a dress for Halloween( inside I knew she knew) I refused to
try it on and never raided my mothers drawers ever again.
If only i had tried it on maybe my mother and I could have had THE TALK?
I have regretted not trying on that dress ever since.

[Liz Jones]

Wife told me to put my name down for a ( men only ) beauty contest, i ended up dressed in leggings & a summer frock -- in the middle of a Scottish farmers field . This started the " itch " for which their is no known cure.......

[DanielleDubois]

I'm sure in different thread I have said it all started for me at age 10 or 11 when I found a corset style girdle and a mohair sweter dress in a cedar chest in the basement of my parents house. Why those two items were the only things in the chest besides some old documents I have no idea. But I tried them on and found out I really enjoyed the look and feel. Never felt I was meant to be a girl but from that point on I enjoyed occasionally becoming one or at least looking like one.

[Lacey New]

Sometime in my early teens, I started to notice girls and the bumps on their chests and the bras under their blouses. Also, in the age of short skirts, offered a glimpse of panties now and then. Then there were the JC Penny and Sears catalogs that had many wonderful color pictures of women wearing bras, panties, slips and other pretty lingerie. As a young boy, I was fascinated with what could be underneath. Well, one day, home alone, I spied a pair of nylon briefs hanging out of the common clothes hamper. They were either my mothers or my sisters but they looked and felt soft and silky and I just had to try them on. You can probably guess what happened and you would be correct. I felt guilty and that maybe I was gay or somehow perverted and I vowed to never do it again . Until a few days later, I had another opportunity and did it again. From that point on, I would put on panties and ultimately bras and slips whenever I could. Eventually, when I got out of college and out in my own apartment, I acquired my own large collection of lingerie and some outerwear

[Debbie Denier]

Trying on my mums tights aged 10 or 11 was a game changer for me.

[Lacey New]

Very young but I think it was actually open bottom girdles I found in the laundry. Soon after that Moms bras stuffed with whatever I could find.
I?m jealous of those who were assisted in this pursuit. I remember putting on a dress over my clothes once when hanging out with my older sister trying to get her to take the hint but she pretty much ignored me.
And yes Bluesman I remember reading the Penthouse letters and always hoping there were more of the cd examples. Newspaper advice columns also once in a while included a cd example which of course I found fascinating.

I used to look for the ads for Michael Salems TV Boutique

[Raychel]

When I was young, My bedroom was next to the laundry.
With my mother and 2 sisters in the house, I had access to
many items that had been thru the laundry and on the folding table.
One time on a whim, I tried on a Girdle and other panties.
The rest is history

One thing leads to another..............
To where I am at today,

[KrissyTN]

<I used to look for the ads for Michael Salems TV Boutique>

I remember Michael Salems, Lacey! Seems to me I sent away for one of their catalogs once upon a time. I had to first get a PO Box so it didn't show up and arouse family suspicion.

I love the pen & ink drawings from those ads and I saw some work from the artist not too long ago on FB. Brought back some memories for sure!

Krissy

[Maid_Marion]

As I was approaching fifty my wife was worried about me getting laid off my job, so we watched What Not to Wear.
Problem was that I was too small to wear men's clothes.
Not only that, but we didn't know yet that she had ALS so her hands no longer worked well enough for altering clothes.
The solution was wearing women's clothes, primarily J. Crew tops purchased on eBay. Back when they were of higher quality.

[BobbiKay]

As a young'un I remember trying on my grandmother's heels. They didn't fit, of course, and I was told to stop that stuff immediately.
As a (pre?) adolescent, I would try on my mother's drawers, girdles, and hose.
There was the Spencer's and Sears catalogs -- many definitions of "the wish book"!
When I was on my own, Variations was a frequent purchase.
I switched from flyfront tighty-whities to Jockey "Elance", which as far as I can tell are unisex (but the ones in the men's department don't have a numeric size, just s/m/l).
I would sometimes "borrow" my (now) ex's pantyhose to wear under my suit to the office, and wear her leotards around the apartment.
Along the way there was a girl that I was attracted to, who was of similar stature and build to me. I remember thinking what fun it would be to share clothes with her. But alas, the relationship remained platonic.
In the last 10 years or so my dressing has taken a decided turn, ever since I discovered the joys of thrift (and thrift-store outlet) shopping, which doesn't break the bank.

[jjjjohanne]

I am not sure, but the first thing I may have ever tried on was Barbie's panties. I put them on my big toe and I felt good. I fantasized about wearing a slip. I loved silky fabric. One day I tried on a slip. Eventually, I tried on pantyhose. They made everything feel like a slip. My mom had used some old stockings to tie up tomato plants one year. I saw them in the winter and untied them and kept them. The sun had bleached away the suntan color and left them looking tie-dyed. I found some old pantyhose that my mom had left in a storage room drawer for use to store onions or whatever. Those were "Silkies" brand. They had the sparkly panty section. I loved the sparkles! Eventually, I became old enough to be left at home and I started trying on whole outfits of hers or my sister's. For a while, I could move her slingbacks to the last hole and I could wear her shoes. But, that passed quickly as I grew.
I was out of college, driving home from work, when I got the idea to go to the store to buy some pantyhose. That was SOOOO scary. I bought $30 worth of groceries to mask the hosiery purchase. That was the first pair of new, pristine pantyhose. Eventually, I went to a dollar store and bought some panties. It wasn't until I moved out of my parent's house and got married that I acquired other garments. I still remember how it felt to go out in public in all women's clothing (but looked like menswear) and screaming inside, "I'm in all womenswear!!"
Eventually, I started going out for morning walks in womenswear including shorts and nude pantyhose. One day, I wore a sport skirt that had shorts built into it. I pulled up the skirt when I was around people and they couldn't tell. At some point, I did not realize someone was near and I the skirt was hanging down. The world did not end.
The next day, I wore the skirt, but did not pull it up. I just wore it in front of people. That progressed to me wearing a normal skirt on my morning walks. I passed some people and they said "hi". Nothing happened. Eventually, I realized that I could just wear women's clothing and present male and it did not matter.
Many years went by and I started owning clothes that actually make me feel pretty. I wore some rather atrocious outfits over the years!

[alwayshave]

I had been dressed in my sisters hand me downs, but the first thing I remember that was of my own accord was my mother's Merry Widow. That item was stored on the attic stairs which were located in my bed room.

[Christina89]

I remember I was about 12 years old when I discovered the "pre-teen" girl in me. I was home alone one day after school watching tv, I was watching a show called Totally Spies. The main characters were out and about buying clothes for themselves. As I was watching an old memory popped in my mind where I asked my mother why I couldn't buy some of the clothes the girls were picking out for back to school. I grew up with what we all call an extended family and at the time the family had 2 daughters. 1 was about 3 years older than me and the other was about 2 years younger than me. My mother told me I couldn't cause they were girls clothes and deep inside I was deeply disappointed cause I liked the way they looked. Fast forward back to watching Totally Spies and something awoken inside me. Without missing a beat I went upstairs to my mother's room and started looking around. I found one of her bikinis on top of a box going into storage for the fall and winter. I decided to start with those. I took them and went into my room since it was in the back of the apartment and away from the street, the street we lived on was the main road into our neighborhood. I started to strip down and as I was putting on the bottoms I felt the awaken getting stronger. Then I put on the top and tied it up and the awaken came fully out. Afterwards I went to the bathroom and checked myself out in the mirror. I loved the feel of it on my body and had to admit my male breast looked amazing in the bikini top. After seeing myself for a few minutes in the mirror I went back to my mother's room and found a skirt, bra and top in her room and grabbed them. I returned to my room, took of the bikini top and put the bra on. I didn't struggle cause for a short period of time when I was 5 or 6 my mother and I lived in a one bedroom apartment and at times I saw her put the bra on while waking up. After putting on the bra I put the skirt and top on. I returned to the bathroom and saw Christina looking back at me with a smile on.

[Lori Anne]

I was about 13yo, read an article in Playboy magazine, where a man had been put in panties, before sex; stole a pair of my sister's panties, and acted out the article. Years later, the sexual part of the equation had left, and I just started to feel more normal being at least underdressed.

[Teri Ray]

Well I hope this information will not become shocking to others............ but I too found my curiosity to try on my mothers things at a young age (I know quite different right?). I can't recall with absolute certainty but I figure I was around 6-8 years old. Found an old bra in the rag bin and tried it on. I liked it and soon found myself looking in my mothers dresser for panties and stockings. Gosh I found liked them a lot too (guilt sets in) I have been hooked ever since.

Does this mean I am a crossdresser?

[Snide_lobster]

Yeah, I wound up with panties, bras, nightgowns, swimsuit, a sundress, skirt and blouse almost right away (not to mention a couple pairs of shoes).

I don't know if I would have started without the help and encouragement of my mother. Being a kid it was hard to understand what her motivations might have been. Wasn't until I was talking to a therapist about it in my 30's that they pointed out that my mother hated my father after their divorce and I was a small version of him. Add to that mom was a raging narcissist, and it gets easier to see.

Not to say I didn't enjoy a lot of it, or that it didn't help me grow as a person.

I?m confused, the actions you describe just sound supportive, if perhaps not a little on the strong side, but far from immediately manipulative or narcissistic? I fail to see how your therapist comes to that conclusion about this aspect of your relationship. Obviously we only have a snippet here, and I?m not trying to pry, but do you feel that she was purposefully trying to emasculate you, because it sounds like you were exploring something you wanted to explore? Did the relationship change over time, become forceful or transactional, or was too encouraging/imposing her will on you? Idk, from the actions you?ve written it just seems like she let you dress up as a girl.

[AlicePetticoat]

I tried on pantyhose that belonged to my mother when I was in my teens. That rush when I slipped the nylon onto my legs made me more curious. I ordered my first petticoat a couple years later, and the rest is history.

[RichardTO]

I?m confused, the actions you describe just sound supportive, if perhaps not a little on the strong side, but far from immediately manipulative or narcissistic? I fail to see how your therapist comes to that conclusion about this aspect of your relationship. Obviously we only have a snippet here, and I?m not trying to pry, but do you feel that she was purposefully trying to emasculate you, because it sounds like you were exploring something you wanted to explore? Did the relationship change over time, become forceful or transactional, or was too encouraging/imposing her will on you? Idk, from the actions you?ve written it just seems like she let you dress up as a girl.

At first, it was just her letting me dress up as a girl, yes. It didn't take long for her to start pushing me to dress regularly, and it was made clear to me that this wasn't just something I got to do at home. Things like the first Christmas after I started, mom was choosing clothes for us to wear for dinner with extended family (she always chose them to look nicest for family photos) and she pulled out a blouse and skirt for me. I didn't necessarily want the extended family to know about it, but I was told I had no choice. I wasn't going to fight mom on it, I had learned growing up that she always got her way or life would be miserable. It certainly didn't help that my stepfather backed her up all the time.

I spent six years dressing regularly, and she pressured me to do it as much as possible, even pushing for me to transition to living as a girl full time when we moved across the state when I was 16 (I fought back and didn't). There was a lot of emotional manipulation in there--she would be affectionate and supportive of me anytime I was dressed, and dismissive and cold when I wasn't. I was punished for doing anything she deemed to be too much like my father and rewarded for being more feminine. I seriously cut back on dressing when I moved out and went to college because I didn't have a strong desire to do so.

There's a lot of stories I have that highlight just how narcissistic my mother was in other ways as well, how she tried hard to mold me into what she wanted me to be.

[Snide_lobster]

Yeah that?s horribly manipulative, sorry you had to go through all that.

[Petra1]

Honestly? When I was in seventh or eighth grade, I wanted to see what it would be like to have boobs.

[RichardTO]

Yeah that?s horribly manipulative, sorry you had to go through all that.

Yeah, this is the woman who, when she didn't get to have my kids visit her for their birthdays (because they always spent them with their mother and I), threatened to sue me for every penny I had. Then a couple weeks later when I calmed down enough to call her and try to work things out, she said, "I'm sorry I ever gave birth to you."

With all that said, I've tried to use my experiences to be a better person. Getting an idea of what it's like to live on the other side gave me a lot more empathy for my wife and women in general. I'm much more a champion of LGBTQIA+ issues and rights because of how nasty some people can be towards them just for existing.

[MsEva]

as others have said, the first truly fem items that I can remember dressing in was two Merry Widow Corsolettes that were left in a trunk in our attic by the previous owner. I think that was around the age of 15 but I always was attracted to fem items. I think that I tried on Mom's girgles and bras but not really clear on that timing. When I found the corsolettes I was in heaven. I had them for many years and would dress in the bathroom as often as I could.