So naive when young

Went to visit my parents yesterday, they are struggling with stairs and my mom asked me to get her a document in her upstairs bedroom that they don't use anymore. Of coarse I don't know why but they hide stuff, she told me the document was in the bottom drawer of her dresser. It didn't click at first but she said that I should find it because I'm very familiar with that drawer. I went upstairs and when I opened the drawer I seen all her slips I used to wear. My God the flash backs started flowing in like crazy and now that comment she made about me being familiar with that drawer made sense. All her slips were still there the way I remembered them, I couldn't help myself from picking some up and opening them and viewings them again.
When we left I explained to my wife what that comment my mom made meant and I told her how the past started flowing in and how naive I really was. I told my wife that my mom caught me once wearing her skirt and never really said anything. I used to work at a grocery store and buy pantyhose telling everyone they were for my mom. I told my wife I don't know why but I would masterbate in the pantyhose and leave them in my drawer thinking I was going to either throw them out or never wear pantyhose again. The funny thing was at times I would find them washed and folded nicely, never understanding if it was my grandmother or mom who would wash them but I never even gave it a second thought. I told my wife my parents would go away for holidays and I would stay with my grandparents and I would stay up late and fall asleep watching TV wearing pantyhose and a slip. I remember waking up in the middle of the night and someone put a blanket on me. I never thought about it back then that my grandmother seen me like that to put the blanket on me and she must have taken it to her grave. My wife almost pissed her pants when I told her about the time I was sharing room with my sister and I thought she went to school. My sister was a slob and there were a pair of pantyhose on the floor, I put them on under the sheets and started going to town with them, all at once my sister came in the room looking for those pantyhose. When she couldn't find them she must have known I wore her stuff because she insintly started pulling my sheets asking for her pantyhose back, I will never forget the look on her face when she finally got the sheets off me and seen me in her pantyhose fully erected. She just stood there frozen and then walked away making a comment like " there yours now". Thinking back now I wasn't as stealth as I thought, it sounds like with my moms comment she just lived with the situation that I was wearing her slips and never told me she knew what I was doing. I explained a dozen more examples of how stupid I was and thought I got away with it but thinking back of what I know now, there's no way they couldn't have known.
When we got home my wife opened a bottle of wine telling me after all those stories she needed a drink and almost wanted me to tell her more and have more laughs and in disbelief of the things I thought I got away with. Wow! how naive we really are when we are young. Just thought I would share some blast from the past anyone else have some.

What you are describing is a click or two beyond naive, but point well taken. We all did stupid things like this when young and honestly thought we were clever. Some of us still do!

Really its kinda nice that everyone in your family has known about your interest in womens clothes for decades. And if I recall correctly, that includes your sister in law and mother in law. So, I cant help but wonder if your mom was gently encouraging you to come a little farther out of the closet.

You do have a loving family Maria

I have to agree with Monica. That is beyond naive. I think our forays into a mother's, sister's, aunt's lingerie did not go unnoticed. All people to some extent are creatures of habit. I use to delve into my mother's undergarments. I always thought I replaced everything exactly as it was. Of course, when I snapped the strap on my mother's sole black bra I am sure she knew one of her sons did it. Nothing was ever said, but, my mother and father tried to catch me in the act. They were never able to confirm their suspicions. If I had been caught I think my ass would have been beaten to a pulp. Both my parents were homophobic. It took a very long time to overcome their hostility towards people like me.

Maria, I think most of us borrowed our mother or sisters dainties when we were younger. I know that my mother knew, she asked me once when I was an adult.

While I didn't have the opportunity a lot, when it presented itself I quite often put on mom's bras, girdles, and slips. I absolutely returned them to their proper place EXACTLY as I had found them - or, at least I thought I did. Naturally, we all know there is no way. My parents never said a thing; so, I always thought I got away with it. Of course, when my own children tried to get away with different things, upon catching them I always told them they couldn't fool me because whatever they were doing I had probably already done.

My mother found 2 new pairs of pantyhose I bought. When challenged I told her I had bought them for a fancy dress party . Never saw them again. Many years later when I came out to her. She confessed that she took them and used them herself as money was tight when I was younger.When my father found some fem clothing I had bought she lied to him and told him they were hers.Also ripped one of her slips she never said a thing.Hence she always knew but never told me at the time.

Maria, after reading your post I'm wondering if u know what "caught in the act" means? If u don't?

THEN, I'll agree that you're naive!:heehee:

Maria, Great post! When I was young I tried on all sorts of my Mothers things, especially panties, bras OBG then dresses and anything else. I was always was afraid of getting caught but to my knowledge I never did. After reading what you said I guess I am not so sure anymore. Oh well:)

I think my mother suspected but also never said anything. Well almost never. We had rented a room out to a female student teacher and I had found my way into her room a few times and tried on her bras and lingerie. Apparently she had complained to my mother who accused me of going through her underwear drawers. So I admitted it but told her I was looking for spare change. Apparently in my mind it was better to be a thief than a pervert! Lol.

A few years later we had another female teacher rent a room and I went and tried on her clothes only this time I was much more careful about putting them back. A couple years after she moved out she became my 10th grade English teacher. I use to daydream In her class about what she was wearing because I knew I had also worn them!

My mom knew all along. I thought I did a good job of hiding the times I would take pantyhose, panties and slips from her dresser. She could sniff out my hiding places in a heart beat. She never would mention a word to me, just gathered her things and went about her business. She was a very neat and tidy women. All of her things folded so neat and put away. We did not have a washer and dryer at home, and after I earned how to drive I would take the laundry to the laundromat. I had three older sisters and I was the one that she trusted with her laundry. I finally learned how to fold her panties and such just like her. She still would find her stuff and take it back. The only constant was that she always kept my secret. She was wonderful that way.

Naive, no not me...

Just not very smart. :-)

Yeah. When I was young I used to borrow my mother's clothes all the time. I only got caught red handed once, and I lied my way out of it. I thought. But in my old age, reflecting back on things that happened I’ve come to realize that my parents must have known what was going on all along. They were just too embarrassed to talk to me about it. My mother would have delegated that to my father. But my father was a secret cross dresser himself. I found his stash once and asked him about it. He lied his way out of it, but it was a pretty lame lie. I think that he was worried that if he brought up my crossdressing I would confront him right back. I wish he could have been more open about it. But it was the early 1960's and men just didn't admit that sort of thing back then.

I thinl we all thought we were getting away with something. But mothers know just about everything about us. We tried to be sneaky, but are bound to slip up. I am nearly 100% certian my mother knew.
I wish my mother was still alive, I would have love to share this with her. She would have been very supportive. Dad not so much, not that he would have been an SOB, but thats not the way boy are suppost be.
Sara

If only! I think I can still be pretty naive at time now!

Ya, ma knew I like to dress in her lingerie.
She was a big influence in my life.
Mom started using my closet, in my pre teen years, to put her things that were too small in storage, especially when I was growing breasts.
She would get some things from a cousin out of college that were my size and I often stayed in my room dressed in lingerie, dresses, and heels.
I had a barbie collection, colorforms, and a 45 rpm record player.
I was sickly and underdeveloped in grade school and spent a lot of after school time at home.
I had a lot of unisex looking clothes. Mom would allow me to walk around the house if I acted like a lady and she taught me how to sit and not get dirty.
I even had a Wendy Ward charm school book from my cousin Susie as she went there to be a model for catalogs.
I was also very nieve as I never knew what it was like to be a normal boy for the most part.
I think being nieve was a good thing...I would of died from all the embarrassing times I never knew I actually had.
It turned out to be special time in my life....we will surly never forget.

Hi Maria, great story!

What your post set me thinking about was mysteries. All the things in life we don't know, and would love to know, but will never know. "Ah, Sweet Mysteries of Life"--to adapt a well-known phrase. And Mystery Number One for me is the one Monica cited: How could you possibly have worn all these feminine clothes without a terrifying fear of being discovered, and of the horrified reaction that might be expected? That does go beyond "naivety," as Monica said.

However, I must admit I had one experience similar to yours. When I was maybe five years old, I did put my mother's nightie on. Maybe I wasn't even five. Anyway I wasn't in school that morning, I'd crawled into bed with my mother after my father left for work, and we were just playing, chatting and having fun. Then she got up, dressed and went about her usual chores, leaving me in bed with her nightie lying on it where she'd left it. Out of curiosity, I put it on. I honestly don't know why I did it. Was it just an experiment to see how it felt? Did I want to feel "close to my mother"? It was the "Oedipal" age, after all. Anyway she came up to the bedroom shortly after and said in surprise: "Oh, I didn't know you were wearing my nightie." That was all; no rebuke. I think I felt a little odd at her surprise, but other than that, strangely, I can't recall any special feelings about the experience. Unlike some of our members. It never triggered me into wanting to wear other female clothes in childhood.

So my motivation at the time was one mystery, but I don't attach any significance to it. I think it's normal for any small child to want to experiment in many ways, innocently and without embarrassment. It doesn't necessarily mean anything about "gender."

In my case I didn't start crossdressing until my early teens. And there's all the difference in the world between being five years old and innocent, and being an adolescent, when I was all too well aware of how "weird" people would think me for dressing in female clothes, and terrified by how they might regard me. So I was always downright paranoid, careful to avoid being discovered and to protect what I called "my security."

Still, I imagine that if I'd crossdressed from early childhood and never drew a horrified or punitive response, just quiet tolerance as you had, a family who discreetly and sympathetically covered up for you without ever embarrassing you by speaking openly about it, I might have grown accustomed to it too. I don't know how old you were when you started dressing, but I'd glad you enjoyed such a nice accepting family.

My circumstances were different. I had a nice family too, with lots of relatives, since my mother and father both came from large families with half a dozen brothers and sisters apiece. They were ordinary decent "working class" folks, though some did well in life. Although our relations were always cordial, unfortunately I didn't get to see as much of my relatives as many children did, because we were separated by geographic distance. Some were wanderers. One of my father's brothers went out to California; another went to Uruguay. One of my mother's sisters and her husband went to New Zealand, where we spent some time ourselves. And my parents moved with my father's job to a town some distance away from where most of our remaining relatives lived, about the time I was born. So I had no "overnights" with aunts and uncles, and no grandparents casually dropping in to take care of me. So your post set me pondering the mystery of how my relatives might have reacted to my crossdressing: something I shall never know. It can only remain a matter for speculation and fantasy.

Some of them might well have been sympathetic, had they known. My "Auntie Ell," for instance, my mother's eldest sister, a big, warm-hearted woman who loved kids, though sadly she never had any of her own. Had I ever stayed with her overnight, and dared to put on her clothes and go to sleep in a chair, would she have quietly put a blanket over me and left me there, just as your grandmother did? Perhaps she would.

Then there was my auntie "Laura" and her husband "Geoff": both pseudonyms. Laura was my mother's youngest sister, the only blonde one, and a bit different from the rest. She had gay and lesbian friends back in the bad old days when it wasn't considered "quite respectable," and had kinky tastes: she and Geoff were into what were then called "blue films." But at least she was openminded. What would she have thought of my crossdressing? I wouldn't have minded dressing in her clothes. She might have seen it as fun. Again, I shall never know.

But another factor in my extended family was large generation gaps. My parents married and had me late in life. Most of my aunts and uncles were considerably older. My "Auntie G," my father's eldest sister, was very kindly, but unlike some people with young aunts, I always remember her as a "little old lady," Three of my four grandparents died long before I was born. My father reminisced with sadness--there was clearly much love in the family--how "We buried Mom on Christmas Eve." That was in 1929. And my one remaining grandparent, my maternal grandmother, was born--believe it or not--in 1877! My ancestry was nearly all English. She was at quite an advanced age during my childhood. It wasn't until later in life, after she had passed away, that it staggered me to realize she was an eleven-year-old girl when Jack the Ripper was stalking London, just a few miles from where she lived at the time. There is so much I'd like to have asked her about--unfortunately these things don't occur to us until we're grown up--which includes her knowledge, feelings and impressions of those and other events of her time. (Not to mention another Great Mystery: Who was "Jack" anyway? one that obsesses a number of fanatics who will never know the answer. Though that's hardly relevant to this discussion!} But what would my own grandmother, a genuine authentic Victorian English lady, have thought of my crossdressing?

Again, I shall never know. She may have been shocked, or kind about it. Who knows? Victorians were not so ignorant about sexual variations as are sometimes believed. But generation gaps make a difference, and if your grandmother was far younger, we know that younger people are gradually becoming more accepting of things like crossdressing.

As for myself, I was left in the quintessential "nuclear family"--just my mother, my father and myself, since I had no brothers or sisters. I can't complain about that, since I had no inquisitive and potentially derisive siblings poking their noses into my predilection for crossdressing as a teen. A minor handicap was having no sisters to borrow trendy clothes from, so I was limited to my mother's wardrobe. But I certainly went to town on it! Being an only child with no-one around to call unexpectedly did give me some privacy. I was lucky insofar as my parents were both working during my teen years, and during school vacations--sometimes in their absence in the evenings--I could indulge myself. I wasn't just into lingerie..I was into everything. I loved spending whole mornings dressed completely in women's clothes and women's underwear, feeling like a girl in a skirt and blouse. So I raided her drawers, her closet and the laundry for her bras, girdles, nylons and panties, her slips, and her skirts, blouses and dresses.

What would my father have thought? I'm sure he would have been shocked and seriously worried, although he was a good kind man and he and my mother had an excellent marriage. But my mother? My mother was a lovely woman, half Irish, with a great sense of humor and a wonderful imagination, the kind that saw "pictures in the fire," could make up stories and was playfully entertaining to any small child like myself. What's more, she often said what fun it was to her to see "men dressing up as ladies" (as she put it), typically in a theatrical performance. Would she have been unworried by my crossdressing? The sexual aspects of it are different, of course. Another mystery I can't remember is how I managed to "pleasure myself" without ever leaving marks on her clothes. I can't recall how I did this now, though I know I was always very careful.

The biggest mysteries of all are, first, did my mother ever suspect I was dressing in her clothes, and second, what would she have thought and felt if she knew? She might well have been sympathetic. But did she ever know? I was so careful of what I called "my security," and I was never discovered "in flagrante delicto"--a phrase that especially means "sexual" misconduct--in her clothes and underwear. But did she ever suspect? She gave me no clue, ever. And I was always so careful to put everything back just as I'd found it. But was I so perfect? Her bras and panties in those drawers, her slips and skirts: did she never notice anything amiss? Nor, as far as I know, did she ever find the few items of women's clothing that I later bought for myself and hid, once I had the money. Reading from other members of this forum, I have to wonder. Was she in fact like your grandmother, Maria, and did suspect, but was kind enough never to embarrass me by broaching the topic, or even hinting at it?

Again, I shall never know the answer to that mystery, since she has since gone to another world. But it doesn't matter. It's enough to know that she was a good mother to me. And that's all that counts. Never mind the naysayers, there are always good human beings around to love us and support us. I'm glad you had a good family too.

I’m certain my mother knew, but she never said anything. The closest I came to being caught was when I was in my sister’s room trying on her hose and heels. I heard my mother coming up the stairs and in a panic I clomped across the hall to my room, losing a heel in the process. I managed to get one of the stockings off and when she entered my room, I was sitting on my bed with the still stockinged leg tuck under it. She gave me a quizzical look but did’t say anything. I’m sure she saw the wayward heel and wondered.

Thanks for the reminder - my mum would do my washing without asking, when I was on leave (I did my own while on base) and she would just fold my washed stockings, bras, undies and place them neatly in my kit bag

Beautiful story, thanks for sharing.......
For myself, in younger years my clothing source came from the attic where mom kept the stuff that no longer fit.....
It was stored in a few cardboard boxes, I don't think anyone noticed that I was constantly trying it on.....
The selection was extremely limited, but I was instantly addicted to panty girdles.....
Their were no nylons / hose / pantyhose yet years later pantyhose became my addiction.
Near the end of my dad's life he told me he had a male friend that wore woman's hose, I didn't respond.
After some thought I wondered if he knew I was wearing pantyhose when ever I could get away with it...
I regret not 'fessing up' that I was hooked on pantyhose.....
Another: Over the years, I was constantly ordering from One Hanes Place, Frederick's of Hollywood, Ujena, Newport News, etc etc etc......
I was living with my long term girl friend, and would order for her and myself...... I had a note on my door and on the orders that if no answer
deliver to the neighbor across the street. After some time I noticed that the bottom of the boxes had been opened and resealed.....
My neighbors were old enough to be my parents, and treated me like their 3rd son. After I discovered their interest in my USPS / UPS boxes I
took note of how often (almost always) my packages were being inspected. I have no clue if they noticed that the orders were almost always for Small & XL...
Eventually I broke up with my GF (after 13 years) and for a while dated on and off. But the orders never decreased, only now all the items fit only me.
Few years later I ended up dating their daughter. Still the packages kept arriving, but only to fit me. And still every one was re-sealed on the bottom.
After a long relationship with their daughter I told her that I enjoyed 'dressing up' and that I thought her parents were inspecting my purchases.
Her response to my dressing was nothing but unbelievable, she encouraged me to try on and buy my first bra. She was constantly gifting me goodwill and clearance items.
When I asked if her parents ever mentioned that I was constantly receiving female clothing w/o a girlfriend she responded that they never 'said' anything.
I stayed extremely close with her parents long after we stopped dating. Considered them my 2nd parents..... They never let on that they knew I was constantly
receiving shipments of women's clothing. They have all passed, and I truly miss their friendship & Love.

Thanks for sharing.
LOL

Not only did both my parents know since pre-puberty, but I'm 99.44% positive my father saw quite a few en-femme pics of me on a personal website of mine (GeoCities, for those who remember) back in the late '90s, as I used to share their computer at that time.

Well, at least I seem to recall them being good/cute pics of me! :battingeyelashes:

Anyway, hope you felt I made a great daughter, dad! :wave2: