How sneaky when you were a child dressing up

[Raychel]

I guess I was fairly sneaky, I was never caught. My stash was found once by my mother. But I was never caught with anything on.

[Ozark]

I was around 9 years old.

My 15 year old cousin had moved in with us. It was a sad story, her mother had died, her father remarried, the typical wicked step mother, car wreck, her father died and the step mother went into a nursing home.

Somehow in my 9 year old mind, I thought she (the cousin) was getting favorable treatment from my parents. I wanted to get the same kind of treatment.

For some reason I thought if I wore her clothes, my parents and grandparents would shower me with affection also.

I put on a pair of her yellow big panties (this was about 1958) and a pair of her side zip jeans. Nobody even noticed. (In retrospect I don't see how they could not have known, but they didn't say anything to me at the time.)

One time when my parents went on a trip and the cousin was in charge of us. She was downstairs reading a book. I got on a pair of her panties and crawled into her bed. (In our house it was scandalous to sleep in anything but pajamas or a nightgown.)

The cousin came upstairs and turned on the light in her bedroom and saw me in her bed. I feigned being asleep. She came over and ever so gently lifted up the covers and saw me in her panties. The covers came back down, she turned out the light and went and got into my bed.

After a while, I went into my bedroom in just her panties. She was in my bed reading a book. I told her I was scared and wanted someone to hold me. She looked at me and told me to go back to bed and hold myself.

The episode was never mentioned again.

She eventually went away to college.

Fast forward about 5 or 6 years. I had developed a bedwetting problem. Wet beds and wet sheets were a real bummer.

My father insisted I was just to d*** lazy to get out of the bed to go to the bathroom. Lots of tears, spankings and wet pajamas. My mother eventually bought me several pairs of 'stay dry' incontinent pants that I was to wear under my pajamas. I was both embarassed and excited about them at the same time.

My father had remodeled our basement and turned it into a bedroom. I was down there by myself, had a tv and radio and my school desk where I did my homework.

I had progressed to buying my own panties by this time.---this was before walmart and kmart. Went to Kresgee's or Woolworths to get them.

One night I was in bed in a just a pair of panties.

My mother came downstairs to kiss me goodnight. My pajamas were lying on my desk, along with some laundry she had told me to put away earlier in the day.

She told me to get out of bed and put away the laundry like she had told me to do. I told her no, could I do it in the morning, I was tired.

Mother insisted I do as she told me to do. Then she saw my pajamas and wanted to know why I didn't have them on and did I have on my 'protection' (That was our code word for the incontinent pants and diapers I wore to bed....we would NEVER call them by their real names, only by protection.)

Mother than told me to get out of bed right now. I refused. She reached down to pull my covers off of me and I blurted out, "Mom, I'm naked!"

She went over to my desk and picked up my pajama bottoms, gave them to me and told me put them on and put away the laundry.

I put the bottoms on over my panties while still under the covers and got out of bed and started to put away my laundry. She then insisted I wear protection to bed and I was always to wear protection and pajamas to bed. Nice people didn't sleep without pajamas.

She then swatted my butt. She must have been able to tell I had something on under my pajamas because she pulled out the waistband and asked me what I was wearing.

I started crying. I told her it wasn't fair, I hated wearing protection, I hated having to wear big white briefs (JC Penny double seats--wish I had some now..she bought them for me) that looked like diapers, I hated wearing diapers to bed and I liked how these underpants felt. I told her I had bought them thinking they were boy's bikini underpants.

She hugged me and said she understood how I felt. But until I outgrew the bedwetting it was so much easier on her to have me wear protection. It was too much trouble to have to laundry everyday--we didn't have a dryer- and to wipe my face and put on my protection and go to bed.

And she stood there. I didn't know what I was supposed to do. I was too embarassed to pull of my pajama pants and have my mother see me in panties. I had only occasionally put on my protection in front of her, never in front of my father.

Finally I said the heck with it, sat on the bed and took of my pajama bottoms. I then walked over to my desk in my panties and turned my back, took off the panties and pulled on my protection.

This was very exciting to me and I didn't know why.

I started to get back into bed and my mother asked if I was forgetting something. I started to put on the pajama bottoms. No, my mother said, finish putting away the laundry.

I put away the laundry in my chest of drawers just wearing my protection. I was so embarassed and excited at the same time and didn't know why.

When I was done, my mother came over and kissed me and said, 'don't forget your pajamas." and went out the door and turned out the light.

Oh man, I knew I was in trouble. Not only was I a bedwetter, but my Mom had found out I wear panties. And she was probably going to tell my dad. I worried about that until I fell asleep. I think I cried myself to sleep that night. I wished I had on panties instead of protection.

The next day when I got home from school, I was in my basement room lying on my bed watching TV. My mom came downstairs with a bag from Sears.

She sat on my bed and said she loved me and was so proud of me for being a nice young man. She told me she was sorry that I struggled so much. She knew I was a good kid. Things will get better she said. Then, as she leaned over and hugged me, she said, "I understand boys need their privacy," and handed me the bag. "These are for you", she said.

Somehow I knew I had the upper hand. I just laid there and didn't return her hug or take the bag. She got up, left the bag on my bed, said supper will be ready when your father gets home and went upstairs. At the top of the stairs, she turned and said to me, "I am not going to mention this to your father."

After a while, I looked in the bag. There was a package of panties from Sear's. Three pair, blue, yellow and white.

[shirley1]

I was never caught, but looking back, I'm sure my mother knew. I raided her undergarment drawer and stockings with regularity. (She worked). I tried to put everything back exactly, but come on, we know that it's an impossibility! Someone found my personal things (bra, panties and makeup). It was thrown out, but not one word was said. Oh for the wonder of the 60's again. LOL

i was eventually caught wearing my younger sisters knickers and ankle socks at 14 - my mom gave me a bollocking and threatened me with what would you schoolmates say if they knew what would your granma think ect basically sent on a guilt trip - it has never been mentioned again to this day its funny how parents can brush things they would rather not talk about under the carpet ! yet they never let you forget drunken exploits ect !

[scherylnmke]

I had started to dress when I was 11 and a year later when I 'thought' everyone would be gone for the evening I dressed in my mothers nylons and a body-briefer(all in one) and a dress and her heels(a little small) and was walking around the house when the main door opened. Because we lived on the second floor I usually could hear someone coming. Not this night!! As I saw the door open I ran, and not quitely in heels to my mom's room, and hid behind the door with the lights off. My sister, who is 4 years older comes in then finds me hiding. She starts to laugh at me all the while I'm trying to ask her not to tell, luckly I realise she's drunk and she goes to her room and passes out on her bed. I quickly undress then go to check on her, she ask's if it is time for school!! I tell her no, and she says she feels like she has been asleep for hours. To this day nothing has been said to me from her, my Mom on the other hand I'm sure knew. One day I heard her talking on the phone to my aunt about her 'little transvestite', and then she saw me and changed the subject. Soon after that a friend was showing me his brothers Playboys and I saw an article about transvestites, making sure my friend didn't see me reading the articles, and I learned what I was. My mother never said a word about it, ever. A year later i ended up living with my dad and his girlfriend and her son(6 months younger). I had frequent chances to check out her lingerie as her son and I hung out with different groups, she had great nylons and lots of girdles. One evening while reading the paper my dad and his girl are chatting and she askes if anyone has seen a pair of her pantyhose that is missing from the clean laundry. Her son abruptly leaves and I'm interogated!! Turns out that him and his girlfriend took them to 'play', and he had her fess up a day later!!

[corrinediane]

I was sneaky. Loved wearing my moms bras. Late 60's. Had a really nice black bullet bra. Peekaboo panties. She had a mastectomy so I got to use forms then. They weren't the same shape though. Still felt great. Brings back memories. I would sneak into my older sisters room and get her nities. Lacey yellow one was my fav. Almost got caught loads of times. Maybe I should have been caught then I wouldn't have to worry about coming out. I would have been thrown out!

[KandisTX]

Was I sneaky? I suppose for the first several years I was sneaky about going into my mom’s and sister’s rooms and wearing their clothing, I would do it every chance I got. Mom and Dad both worked so when I was home from school due to illness I had the full day to dress up and have fun in their clothes. I recall one day where I almost got caught by my sister, I had decided that I needed to experiment with her make-up as well as wearing her clothes. I hadn’t thought about how to remove it though, I scrubbed and scrubbed and thought I had gotten it all off, but when she got home from school she saw trace of her blue eye shadow on my eyes. She never said anything about it, but I wish she had, it would have been nice to have an ally, then again, she could have become my worst enemy as well. I have since lost touch with her and really wish I could connect back with her so I could talk to her and maybe repair things between us. (What happened there is another thread entirely I won’t go into now).

Those first years of sneaking around became wonderful memories, but the time came when I wanted some items that were “mine” so I kept a watch on the laundry and their dressers to see what items were not worn EVER, and made my choices of some nice panties from my sister, a bra from mother, pantyhose, slip, and a body briefer from mom. I had never seen these particular items in the wash and they were always in the back of the dresser drawers so I figured they would be safe items to remove and keep as my stash. Well, I hadn’t put much thought into where I would keep them so I put them in the bottom of my pajama/underwear drawer. Mom worked for Johnson & Johnson Personal Products Division so there were always samples of items in the bathroom, so I took a sample package of Carefree Panty Shields, lightly scented for that more feminine feeling (still wear them daily now along with my panties and pantyhose), and had them stashed in the dresser drawer as well.

Mom usually did laundry and would, on occasion put our stuff away, either that or she was just a nosy person (not my real mom but technically my second cousin, her mother was my great grand-mothers sister and I was “adopted” by them for a brief period [10 years], of my life). Anyway, I had spent all day at school fantasizing about when I got home and would be able to put on my bra, panties, pantyhose, slip, and body briefer. When I got home from school, I immediately went to my room to change and when I opened my dresser, the clothing was gone. I went to see if I could find it again, sure enough it was all sitting on mom’s dresser. She never said anything to me about it, but eventually I got tired of sneaking and hiding and I wanted lingerie and feminine clothing of my own. I figured the best thing to do was to tell her, or rather allow myself to get caught with my pants down showing her panties and pantyhose.

I prepared myself as she and I were the only ones home, I went to the laundry room and took some of my sisters panties and a bra off of her stack of clean & folded laundry and snuck into her room and took a pair of pantyhose and put them all on underneath my sweat pants and sweat shirt. I went out to talk to her in the back yard and asked her some generic questions to get a feel for her mood and then we went inside. As we were walking into the house and heading upstairs, I was taking off my sweat suit and asked her if she ever wondered why I had her clothing in my dresser. She said “no”, I said “Well, this is why” and I tossed my sweats over her shoulder and stood there wearing nothing but a bra, panties and pantyhose. She of course over reacted and decided that I was sick and needed therapy and that was the end of that. Six months later I left there and moved back with my real father and mother and went back into hiding until I again decided that I wanted to have some stuff of my own. This time I would do it right, mom (my real mom) was much more understanding and open about things so this time it would be different. Once again I set myself to be caught. I knew that mom would be the first one to come home and so I went into her room and dressed myself in her bra, panties, and pantyhose underneath my bathrobe. I have very pale skin and my socks only came up to the mid calf range and my robe stopped about two inches above the knee. This means there was an area of about 5 inches of my legs exposed and the suntan pantyhose were QUITE noticeable. I heard her keys in the front door and timed my exit from her room with the moment she was in the apartment and closed the door behind her. She saw me coming out of her room and asked “What are you doing in my room”. “Nothing” I said, I can see her eyes move to my legs and she asks me with a knowing smile “What are you wearing? You have a box of your sisters bras in your closet (I was storing them there for her honest, [besides, they didn’t fit me]), and now this”. I smiled and said “No, I don’t have a box of bras, only one”, and I opened my robe exposing myself wearing her underwear. She smiled and said “Well, you know you can’t just walk around in a bra and panties, let’s find you something to wear over them.” With that, we went back into her room and she proceeded to find me something to wear over the top of the lingerie, and she gave me permission to wear her things until we could go shopping and buy me some of my own as long as I washed all of her things before I returned them. Now, she gives me lingerie and femme clothing as gifts, and she calls me her daughter as well as her son.

Kandis

[DonnaT]

I have four brothers, no sisters.

The house we lived in had two bedrooms upstairs, two of us in one, three others in the other.

NO DOORS.

I was never caught by my brothers. Came close once when I was in the kitchen getting a drink of water. I had to hide in a broom closet.

My mother found my stash after I left for the Army.

She also caught me once, but I was being very daring at the time. I'd have never been caught otherwise.

[BarbaraTalbot]

I could
dress as a girl pretty much when I wanted
at home.

Even before I realized I WAS a CD myself I had told the unhappy story f my experience at 3.5 and the same that was heaped on me for trying. My wife is so much healtheier and this is before as I daid I (Or she ) understood about me. Both boys and one of three girls have crossed in fun and were treated with respect. The youngest boy still does sometimes, and it is just fun for him and no gravity is place on it one way or the other. He borrows mom's highest heels (well actually the pairs he picks from 'mom's' now EXTENSIVE collection are usually actually mine, the boy has good taste!)

We found a pair of cute heels in a tiny size of maybe 5.5. We plan to add tat to the dress-up box the next time he asks for mom's shoes. We would just hand them to him, but I don't want to color his choices either way. Its fun to see his joy at dressing in sharp contrast to my violent mistreatment.

But way back when I was a child, what I did felt so dangerous.

FOr me it was dangerous. I did it anyway, bit only with the most secure privacy I could manage, locked door, every ne out of the house, locked bathroom. not healthy.

[Janis Edwards]

I am pretty sure I was never caught although there is a possibility our cleaning lady may have seen me dressed when I was about 10. She had a key for our house and arrived for work on an off day, scared the bejeebers out of me. The headlines might have read " 10 Year Old Boy Dressed as Girl Found Dead of Heart Attack". If she did see me, I don't think she ever told my parents. I actually remember what I was wearing that day, mothers black fishnet stockings, girdle, black velvet heels (they wear absolutely the best) and a black and white flowered dress. They all fit me perfectly at that time as we wrere both the same size.
Oh the memories!!!!!!!!!

[loki_uk]

I was sneaky enough, I never got caught except for the time in primary school they sent me home wearing the regulation blue girls knickers (it's a long story but I needed underwear and that's all they had he he)

I wonder whether my mum suspected though, as she did sometimes give me hand me downs till I was a teenager of her more neutral clothes like shirts et