Susan's Place Logo

News:

Please be sure to review The Site terms of service, and rules to live by

Main Menu

ever been caught crossdressing? how did it make you feel ?

Started by cc43, December 29, 2008, 09:50:47 PM

Previous topic - Next topic

0 Members and 1 Guest are viewing this topic.

billie

we need to be who we are and if that is somehow interfered with we become something that we are not.
  •  

Veronica Morph

here are my stories,
well never got caught 100% maybe were some alerts or very close wake up calls, needed to be less impulsive here how it went,

i started when i was 6 years old ...balablabla,
I remember at the age of 6 some times when I was trying  on and off my moms heels i was going around the house even in front of others brothers sisters etc, i even made my brothers wearing them as well even with hose etc, my mom one day got tired of it and forbid us to play with her stuff, mostly because we were breaking the heels and tearing off the nylons, i stopped for many years cding,


when i was 16 my sister caught me in the bath wearing a thong, --ouch that was embarrassing!!!-- i can remember i got out of trouble by making jokes and saying i was feeling super horny etc, im not sure if she forgot but it didnt matter to me and she felt it as a hormonal teen ager thing.

Another  one and very strong one was at work, it happened 10 years ago, i was at my office lunch time i though all the staff was out i was opening a package of new shoes i never ever do this in the open of my office, but that day i passed by the po box  and got my package of 6inch ultra high white pumps, i was so excited i couldnt wait for the end of the day so i went for it and open the package, i had all ->-bleeped-<- out in the open and I decided to put on my new shoes, of course those ones were my first 6inch high heel shoes, couldnt walk at all, i just sitted there admiring and enjoying the moment ....(picture this: i was seated at my chair infront of my desk which faces the entry door of my private, the door was half open so i though I could hear when somebody approaches) well this time a guy from the IT department came along very fast very silent i couldnt even know he was approaching to the office, i could hear him , until i was having him almost infront of me, like a ghost, ...->-bleeped-<- i said to my self, i suddenly asked him whats up? in a way to say to him stopp there!!, he said he needs to plug something on my pc for the network etc, .....i said ->-bleeped-<- this time he is going to discover me, ->-bleeped-<-...........(i felt i couldnt do anything to avoid the ->-bleeped-<-n problem , so i though fast, i better be rude and he know me as a rude guy than a weird fellow that wears fetish womens shoes at the offcie when noones is there.....i said to him ok so wait there where you are!!!, very imperative, he wondered why? people sometimes lack respect, this guy really invaded my privacy..........I looked around my shoes were at the oposit of the room, there fore i needed to be naked feet, but where on earth i will hide the shoes, which were having a ultra high metalic needle heel, ->-bleeped-<- under my desk? hell no!! he will discover there is where he was going, , on a drawer?, all were full, behind the pc cpu ? nah he may like to check something inside he is the computer guy, ...so where?    .....and there i was with my heels still on seated on my desk one guy staring at me what am i doing, and why he is waiting for me?, ...please give me a medal for the follwing.....  i told him demanding voice,   hey, you pass me that trash can, (which was at the entrance of the offfice, perfect size for him to pass it over my desk and him not to see what i will be disposing under my desk, ......i took of the shoes and i put them in the trash can i trashed a bunch of papers that were around and then i spit over it very disgustingly , these to seal that he wont check it over, ....what a freak!!!!!....well it worked, i told him sorry for that, i was not feeling ok and i needed to trash my desert which made a mess all over my place, be carefull for you not to spot your self with some.....he said no problem this will be fast........he went over my pc, install software, then check out the cpu he indeed rotated it to reconnect something, my guts were right and then he finnished and left, he even didnt notices i was naked feet, i was wearin a black hose underneath, that is nothing it could be very thin socks.

I still feel the embarrassment and the scare of that day, i was lucky to think fast and to mislead my fear into first arrogance and then into caring for others, or disgust i dont care what the heck this fellow ended thinking about me, but im certain he is not saying i wear 6inch white high heel metallic pumps at work, hahaha.

Another time also at work, it was maybe 5 years ago, i changed jobs this time my desk was not in a private, was in the open, so i can see everybody who comes in and who comes out, my boss always leaves early and he is the owner of the company, i stayed until late and waited for the last guy to leave then as the last person to be in the office i needed to close behind so what i do regularly is to close all doors including the gate which is automatic, it takes 10 seconds to be open all the way for a normal person to crawl under safely and not hitting his head, so i normally take the time to dress up completely,
one day i was enjoying al long dress and my new high tight lace boots, 5inch high heel, i was walking around the office trying the support and see at my self thru the reflexions of the windows and the glass doors etc, and then suddenly......the door seems to open and the gate to go up ......oh ->-bleeped-<- i was not gonna make it i ran to my seat i though the boots will never be able to be taken off, so what do ai do? i put on my sweater on over everything and left my dress and the boots on, i seated on my desk in a way noones can see my feet, the dress was black so it was ok, it didnt shown any irregularity while i was seated, i took the fix phone and started to call a friend and started a chat in spanish, .......the person who was coming inside was my boss, ->-bleeped-<- i though ...he will see me like this...i have to have prepared my plan.......

Plan A, to keep talking and be very focused on my conversation, my boss knows nothing in spanish so he couldnt know to who or for what was the call about , he respected the privacy, he went directly to his offcie , and kept staring at me, he came to my desk and ask me ...wow you work late!!!, are you up for a dinner after-wards i will do something at my office and then i go, or you have plans i said to him well depends, i am in the middle of something very important and i need to do it today, i let you know if i can Finnish fast.....he was ok with that response but he was still wondering why i was having a small luggage in the middle of the way? hahaha , inside were my collection of high heels, nylons, dresses , corsets etc, i forgot to pull it under a desk or out of the way, luckily it was closed.

My plan A was to keep talking as long as i can until the guy is gone, ......it took very long, i needed to keep the conversation with my friend i explain do not hang on me i need to get rid of a guy who is waiting for me to go out, and i really dont want, my friend was supporting me but he needed to go after 20 min, so i only had 20 min left, .....i could fake the call because the little light of the phone will turn off and my boss will know, .....

If in the even my boss finds out i was cross dressed, which was unlikely i was not going to stand up for nothing, only by the ofrce and my boss needed two guys to do that, so i was quite sure i was fine and he wont see me in my dress and my boots, they were on all the time, i need to take them off with the lace and is very complicated, thats why i even didnt try to make the effort was gonna be useless.

So my plan B if incase i was busted anyhow, was to tell the boss i was dressing up for going to a stupid party that i was trying to get away from, but my friends where pushing me to go as all of them were there as fetish bdsm tgurls, and i was the only chicken not coming in, thats why i was talking so long at the office, dressed but not sure to go, embarrassing you (my boss) catching me like thise, well now you got me, tell me how bad do i look? shall i go ahead and make the ridicoulous or i let down my friends and say bye to this group of close firends i had been going out for years.? give me a sugestion please. by the way all this ->-bleeped-<- is too small for me and im very inconfrotable, so be quick on your opinion which i will follow.

So i have this ->-bleeped-<- on my head as i was talking to my friend on the phone watching my boss doing his things thru the crystal of his office, ....suddenly.....he stood up but didnt took his keys and his wallet and he started to walk away from his desk, i suddenly knew he was going to the restroom, ok how long it will take maybe one minute? so i told my friend wait hold on, i started to untie my boots, it took me forever, i was there fighting hard to take them of, finally i got hem of, i put my jeans over the dress, i didn't care, and then my shoes, i hide the boots on the luggage but didn't move it from the way, i look at my self to see if the dress was not showing from nowhere, it was fine, i kept talking to my friend and then my boss came back i said bye to my friend on the phone, very quick and then i told my boss if he is ready to go? he said nah im stock in this ->-bleeped-<-, i told him quickly ok dont worry we can do it tomorrow, suddenly i stood up put on my coat over already the sweater that was over a dress, and took my luggage slowly so the guy there could see it was nothing special, he asked, are you going somewhere? i said not really i got to take a bunch of shirts to the dry clean. he laugh.

phieuuuu, that one was close, i left.

The other thing was where i was going to change back my clothes for going home? then i stayed in a cafe and i took it very easy, i waited for two hours it was very late, i call my boss and asked him if he was still at the office because i couldnt find my wallet, (just checkin) he said he was already at home, ok i said , too bad i think i will go back to check as i have credit cards etc, he said to give him a call if i needed help, then i went back as i was not far, i walked in i changed up again i dressed another dress tried another boots and left peacefully,

What i can conclude is that no matter if we are or not caught, we will never stop, the embarrassment and the fear is not as strong as our willing to dress up again and again.

Be careful guys and keep your beloved ones keeping a peace of mind, by thinking only nice, regular, common things about you, dont test no one, is non of their business as what you do and what you feel is only for you not for others.

Veronica Morph

 
Veronica Morph
  •  

Eva Marie

I got busted by my daughter for wearing clear nail polish at a restaurant. I laughed it off and kept my hands under the table for the rest of the meal, chipping away at the polish to try to get rid of it.

I got brave and went outside once wearing a small bra, and a friend i hadn't seen for years suddenly drove by and wanted to chat. I had on a thin cotton shirt, and i'm sure the bra was quite visible. So, i kept my arms crossed in front of me the whole time we were talking. I don't know if my friend noticed anything or not.

Another time when i was first experimenting with makeup i went to work early one morning, and later went to the bathroom where i discovered that i hadn't gotten all of the eyeliner off. It was smeared below my eye, and would have made for an embarrassing situation if anyone had seen me. Since I got to work early I hadn't yet talked to anyone, so i was able to scrub it off before anyone noticed.

I took all of these experiences as reminders to be extra careful when i dress up.
  •  

spacial

I don't know if this is quite in the spirit of the thread, but when I was about 7 years, I tried, as I was geting ready for bed, making myself up in such a way that I could imagine I was a girl.

I covered my ugly bit with a thick cloth and wrapped something around myself so I could imagine I was wearing a dress. I think I also covered my head because my hair was quite short.

Anyway, my father came in for some reason. He then left and the next I knew, both my parents and my older sister and brother were in. I was made to get out of bed and take all the stuff off in front of them. This was followed by some shouting. I do remember I tried to keep my eyes shut so I could pretend it was a nightmare. But I was made to open them.

After that I was the weakling girly who needed toughining up.

Hope that isn't too depressing. But it's nice to be able to say it.
  •  

Veronica Morph

SPacial,


you just made me feel the horrible feeling that i would be feeling if i were caught doing similar ->-bleeped-<- during my eraly days, it is a horrible horrible feeling im sure, im sorry it made me even laugh cause of the nerves, ......im sorry you had to pass that big embarassing moment,...... tell me...after that moment did your relationship with all your family was the same as it was a whatever thing? or everybody changed the way to talk with you as a weirdo or as a pervert? i always think if it were me when i was young i was to be seen my entire life in a very negative way. my family is too conservative.

sorry to hear that, i hope you didnt cared afterwards and it was one of those silly moments you are being caught on doing.
Veronica Morph
  •  

spacial

Quote from: Veronica Morph on September 28, 2010, 05:56:18 AM
SPacial,


you just made me feel the horrible feeling that i would be feeling if i were caught doing similar ->-bleeped-<- during my eraly days, it is a horrible horrible feeling im sure, im sorry it made me even laugh cause of the nerves, ......im sorry you had to pass that big embarassing moment,...... tell me...after that moment did your relationship with all your family was the same as it was a whatever thing? or everybody changed the way to talk with you as a weirdo or as a pervert? i always think if it were me when i was young i was to be seen my entire life in a very negative way. my family is too conservative.

sorry to hear that, i hope you didnt cared afterwards and it was one of those silly moments you are being caught on doing.

I'm sorry to say that it wasn't forgotten. My family's dynamics were quite complicated.

I spent a lot of time brooding over many things, but there is little to be gained from digging up the past.

I really feel we need to work to make society a better place for children. We hear so many positive things, parents being tolerant of their children's feelings and needs.

Today, in the news, there is a story of a young boy of 8 years who wet his bed. His father apprently spent 90 minutes spraying him with cold water from a garden hose. http://www.thesun.co.uk/sol/homepage/news/3155069/Hose-down-dad-facing-jail-term.html?OTC-RSS&ATTR=News

It's too easy to assume that things are improving. They are for some. rejennyrated had incredable parents. But even she will admit they were a minority and had a somewhat alternative lifestyle.

In my parent's case, they had lived through WW2. They were convinced that there would be another war and that their sons would go and fight. So trying to force us to be tough was a priority for them.
  •  

Deanna_Renee

I have only ever been caught once in my life. It just so happens that it was the first time that I had ever 'experimented' with women's clothes. I was maybe 8 or 9 and had been curious about my mom's and sister's panties and bras in the laundry for a little while, wondering how they would feel and how I would look in them. One day when my mother was out and I was home alone, I decided to try on my sister's red cotton panties. They felt oh-so-good and felt 'right', I was hooked. Then I heard the sound of the front door being unlocked and I scrambled to put something on before my mom reached my room. Unfortunately, I only got as far as putting on my white cotton briefs (over the red panties) by the time she got to my room (did not have a door). Her Mom radar immediately saw through the white briefs and picked out the details of the red panties beneath.

She asked what I was doing? nothing
Why are you wearing those? I don't know (honest answer)
How long have you been doing this? This is the first time
Don't let me ever catch you wearing these things again or I will send you to the same place your father went (mental hospital) and you won't come back.

I have made absolutely certain that she never caught me again - I didn't stop dressing, but never got caught. It was one of the most humiliating and embarrassing experiences in my life. It was around that time that the depressing really starting attacking me.

Deanna
  •  

Ani

When I was old enough to not need a babysitter, every time my parents went out and I knew they'd be gone for a couple of hours or more I'd head straight for the good stuff in my mom's closet  ;D (I didn't have any sisters or I'm sure I'd have been checking that out too ::) ).   One night they left and I went to get dressed up and opening a drawer I found a note that said something like: "go do the dishes, and then finish your homework, love mom".  I was obviously busted, but she never said anything, and neither did I.

Another time my secret stash disappeared, and I can only presume she found it.  Again, no comment by anyone.

Much, much later, while in college I was living in student housing with five other guys.  The previous tenants had apparently been female and there was a box of clothes that had been left in the basement - that included panties, bras and lingerie, in addition to some shirts (unfortunately no dresses or skirts!).  Before finding that I'd been avoiding the 'call to dress' for some time.  But just knowing it was there in the same house with me was too much to withstand and I soon brought some of it upstairs and hid it in the back of a drawer in my room.  One night, very late after a party, and very drunk, I was seen by some of my roommates dressed in a nightie.   I took quit a bit of ribbing after that - but in retrospect I don't think any of them really held it against me in any way.  We continued to live together in the same house and got along fine.  Although after many years I've not kept in contact with them, and I probably would have if I hadn't been detected.  I regret that, but can't seem to overcome it for fear it would be brought up again.  It's easy to be a coward.   :embarrassed:
  •  

Cindy

Quote from: ani on October 05, 2010, 01:42:21 AM
.  It's easy to be a coward.   :embarrassed:

I totally disagree.
I think that thought is what keeps people in closets. The hardest thing is to be a coward. The easiest thing is to stand up and be yourself.  Many people think it is easy to hide. Nope, the easy is to walk out and say hello world.
The more you do it the easier it is, the more you are a 'coward' the further the walk.

Love Life, Love You.

Cindy
  •  

spacial

  •  

Katelyn Alexandra

Had a few close calls, but never caught outright. Usually it was when I was sleeping in girls cloths and someone comes in and tries to get me to get out of bed. I usually just took my time and tried to get whoever to leave for a second (I'd often just claim I wasn't wearing anything). I was always worried what they would say, but I've since admitted cross dressing to my parents, so it wouldn't be a problem if that happened now.
  •  

cdalyssa

I started experimenting when I was about 9, by wearing my mothers clothes(no sister only an older brother). I enjoyed dressing up in her bras, dresses, pantyhose and heels, but always felt disappointed that I could never complete the look with make-up. After a year of closeted dressing and sure no one knew, because it was never discussed, I was stunned that when Halloween was approaching and I was deciding on a costume, my mother suggested I go as a girl. Even though I was 10, I did have a guilty conscience, so I was sure my mom knew something and was testing me. So, I did the typical thing and acted disgusted with the idea, thinking she would reveal that she knew my secret and confront me. She didn't. My mom used to make our costumes, so we always had our costumes picked out by mid September so she could make them. This talk happened in August. Well, after my refusal, I was dying inside wanting to accept my mom's suggestion, but scared that if I did my secret would be out.

Well, at this time my best friend was a girl who lived next door. One day we got to talking about Halloween and what we should go as. We always trick or treated together. I said I was undecided and she said she was going to go as a boy. She then said, "since we always T or T together, wouldn't  it be cool if you went as a girl. We could pretend to be dating or something." I replied with "are you serious?" However, I knew that's exactly what we would do. I now had a way to accept my mom's suggestion without accepting it. So, I got the courage and told my mom that I would dress up as a girl, since my friend was going as a boy.

That Halloween, was the best ever. I got to indulge my secret in full view of everyone, without them knowing how much I was loving it. My mom obviously did my make-up, what she didn't know was that after she was done, I went to my room and wrote down the name of everything she used. I never wore make-up until that day, so I had no clue what eye shadow or blush or foundation was. I wore a white blouse with big ribbons that needed tying at the collar, a gray skirt, with blue tights and black ballet shoes, oh yeah and a ladies fedora. The clothes were borrowed from my older cousin who out grew them. The only thing bought was a training bra, which we stuffed with tissues. I ended up keeping the clothes even after Halloween. I remember my mom washing them and throwing them in a garbage bag with other clothes she was going to donate, since my Aunt said she didn't need the clothes back. I was tired of wearing my mom's clothes that never fit and the fear of her finally noticing clothes are misplaced, so I decided to take the clothes out of the donation pile. I hid them in the gym back that I kept my soccer equipment in. I was always nervous she'd notice the clothes missing from the bag, but she never did. I was always woke up early, so knowing that, each night I would go to bed in my Halloween costume.

The next time I feared being outed was when I was 15. My parents went to a Christmas party and my brother was supposed to be at a friends house for the weekend. My parents would always call when on their way home, so knew I would have time to change. I had the house to myself, and did what I always did, got dressed. By this point I was back to wearing my mom's clothes because I had out grown my Halloween costume and never considered buying clothes. Anyways, I was all dressed up(minus make-up, only attempted make-up once after Halloween, found it too difficult and time consuming). I was wearing a bra with matching panties, white cocktail dress, white hose, with white ankle high boots with 3" heels. I had longish hair, so I styled it as much as I could to look feminine. I was in pure heaven for about 2 hours, until it almost turned in to hell. Not expecting anyone home for another hour or so, I was frozen with panic when I heard the door that lead to the garage open. I had nowhere to hide and only seconds until the person would walk into the family room and see me as Alyssa. My reaction, I grabbed the blanket that was on the couch and covered myself. Just as I did my brother walked into the room. He questioned why I was covered up since I was sweating and the house was warm. I lied and said I felt sick and questioned why he was home. He forgot a piece of hockey equipment he was going to need the next day. He got what he needed and left again. Once he left I decided to get undressed because my parents could be home soon. Which was the case. I was just opening the door to my parent's room to get undressed when I heard my dad announce they were home. I changed direction and headed to the hallway bathroom. I was able to get undressed and back into my own clothes without any further incident. The only problem was that it took another day for me to have the time to return the clothes to my mom's closet.

It was the Internet that got me busted. Because of circumstances, I attended a local college and to save money stayed with my parents.  I had pretty much stopped dressing after the above scenario. I still had the urges, but felt the consequences were too severe. I grew up having a huge crush on Alyssa Milano(inspiration for my name) from the TV show "Who's The Boss?". Well, one day(I'm 21) a movie channel was showing a movie Alyssa did, where she plays a college student who falls in love with a guy who also happens to be secretly cross dressing as her BFF. Seeing this movie really reignited the "Alyssa" in me. Not feeling comfortable dressing in my mom's clothes anymore, I decided to go online. I had done some very brief CD research online before but never to shop. I found a site that specialized in clothing for cross dressers and with much apprehension, ordered my first outfit. I purchased a sexy navy blue mini-dress, fishnet stockings, a starter's make-up kit and a bra & thong set. The package arrived 2 weeks later. Our family's daily schedule guaranteed that I would be home alone to receive the package no matter what day it arrived. What I didn't consider, happened a week later. After coming home from school my mom said we needed to talk in a very serious tone. I had no idea about what. It turned out, that 2 days after the clothes arrived, my father had gone around the house to collect the garbage and in doing so happened to see the tags that I removed from the clothes in my bedroom garbage, which lead to them finding the clothes in a gym bag in my closet. It had taken my mom 3 days after their discovery to confront me, which she did by having everything I bought displayed on the kitchen table. In total shock I just froze and tried to come up with an explanation. I was still struggling with what I was feeling inside regarding my dressing, so when I unfroze I just revealed everything. I was expecting her to say she suspected something, but this caught her completely off guard. To understand cross dressing better and why I did it, I saw a psychologist for about 18 months. I convinced myself, the shrink and my family(I also told my brother) that it was a phase and that I had gotten it out of my system.

Which I did for about 5+ years. Now, I sleep in a baby doll nightie every night, wear panties and hose under my clothes almost daily, and fully dress about 2-4 times a month when my roommate is gone. To this day my family believes that I stopped over 12 years ago.

I want to finish by saying that I missed this place. I joined last month planning on being a regular contributor, unfortunately life got in the way. Everything is back in order again, so I will be a much more frequent visitor.
There is nothing I LOVE more than being able to express my femininity in the silkiest, softest, & frilliest clothes in my closet.  I owe a Thank You to Alyssa Milano for being such a great feminine role model any gurl could ask for. :eusa_naughty: :icon_kiss:
  •  

spacial

cdalyssa

That was a great story. I really feel for you, so many missed opportinities, missed because of lack of confidence.

Really hope you can find the courrage to come out to your family. They sound pretty good.
  •  

cdalyssa

Spacial, thanks for the encouraging words. That's what I love about this place. I'm still not sure about coming out to family. While I enjoy being Alyssa, I still enjoy being Rob. I plan to still live my life as Rob, so right now I see no need to come out. I'm single right now, but have told 2 of my most recent girlfriends about Alyssa. The 1st gf was fine with it, but the 2nd ended our relationship because of it. So, when I'm serious again about a girl, I will be honest.
There is nothing I LOVE more than being able to express my femininity in the silkiest, softest, & frilliest clothes in my closet.  I owe a Thank You to Alyssa Milano for being such a great feminine role model any gurl could ask for. :eusa_naughty: :icon_kiss:
  •  

Xakkun

When I was still living with my mom, two of the few blessings I had at that house was a door with a working lock and a bathroom built in. Mom would get pissed any time she came to barge in and the door was locked, but even though I always panicked whenever my door was being banged on whilst I was in a miniskirt, I was able to say I was just using the bathroom and didn't want to miss whatever was on TV.

Since I've been living with my dad, I've been limiting my dressing up to when I'm the only one home and when I'm the only one awake. Although there was one time a friend of mine nearly saw XD
  •  

Veronica Morph

Alyssa:

your story is very nice and i can remmebr on many of the moments i was also home alone and fully dressing up, i got a close call similiar that you got with your brother, i was also in the fist floor of my house (two story home) and heeling very nicely in the marble floor of the dinning room, soon after the door just open, i ->-bleeped-<- no place to hide no place to undress, the heels were having a strap around the ankle and i needed at least 30sec to unfasten it, so i needed to act fast and the blanket method helped well but I was inthere for quite good time with heels and hose and everything on not able to even move or go to my bedroom , the clicka of the shoes will uncover me athomatically, I decided no matters what will happen that blancket doesnt goes from me and i was supposed also not feeling ok, doing homework in the dining table, my mom was around for pretty long time in the kitchen preparing food etc, i couldnt go nothing i was stock there, and the only thing i could do was to remove the shoes swhen i could as the blanket was too small any moevement will show a leg and a shoe easily, so i needed to be careful.

Finally i did it and then when my mom was focused on soemthing i staood up and ran fast updtairs, saying i was going to the bathroom, i removed all the stuff and found it exciting the adventure, i remmber i even dare to keep the hose on and put on payamas and sock underneath, so it was not enought for me,

MAny ocasions i remember i couldnt return the stuff back to its place on time, some times when it was too obvious i disapearthem and kept them better said that is lost rather than i wore it, also i never used stuff that my mom use regularly only old and forgotten things, hose that were already thorn or cheap or she was having many the same style etc, i remember that a couple of times i broke zippers on skirts and dresses, i stayed hours repairing them etc, i learn to be much more careful afterwards.

By the way as Cindy wrote meaning that it is better to say the truth than live in a lie, well is right, but i dont call it to be coward action, everybody has their own reasons, and not sharing the same view of life in cross dressing, being out from the closet is not being coward. just wanted to pointed out, and no offense taken neither.
Veronica Morph
  •  

pebbles

There was a period when I was a teenager where I did this alot and even snuck out at night and when dressed like this I would occasionally take a photo so I could present as female online without raising suspicion it also felt nice when I was read as female from the photo.

However there were a couple of incidents.
Most memorably The time I snuck out one night out my window when I thought my mum had gone to sleep I wandered around abit and came back went to bed but apprently my mother was downstairs in the dark when she heard me coming in in the dark in the poor illumination and me having practiced a so-so female voice she thought I WAS female.
The next day she confronted me about it and accused me of sneaking girls into the house without permission at night and doing questionable things... The idea that I WAS that girl was completely unthinkable to her.

Another incident during my teens, I mentioned the photographs well I let a friend borrow my laptop I thought I'd hidden all of those photographs however she somehow found one that I'd carelessly missed it wasn't provkative(It never was) just me pulling a face at the camera.

She did confront me and tell all my friends and it was a big laughing fuss with everyone around about it at first I told her "That isn't me she dosen't look anything like me that's just a friend" still they were doubtful of my claims I told the best lie I could and they brought it at face value.

In both cases I felt an incredible sense of dread and gut wrenching fear... You know that mortal social fear you feel light headed and want the world to swallow you and about but I equally knew it wasn't enough to make me stop.

And there was an incident in my childhood age7 or so whitch I recall in whitch I apprently crossdressed and didn't think anything was wrong with it I don't even know if it was gender motivated. But my mother found me and scathingly said to me "Oh what? You think your a girl now or somthing?" in a harsh tone whitch made me realize I wasn't permitted to do such a thing.
  •  

JoanneTV

I was caught repeatedly as a kid, and then "shamed". Boys shouldn't do this as I was always told, but my inner self always found a way to raise the bar. It was habit forming for awhile, but I got good at hiding it, in shame. Fast forward 15 years, I forgot to take off my make up one night before leaving the house, and was called out by a very passable tv gurl. That was very interesting to be in that situation and I was thankful that she was nice about it.
  •  

Amy85

I've had a few close calls. Most of them were due to the lack of a lock on the bedroom doors in the house I grew up in.

There were a few times my Mom would pop open my door in the morning to wake me up for school and I would be laying there under my blankets in my sister's "borrowed" undies, and a few times her one-piece swimsuit. (I maintain that a one-piece swim suit is one of the most feminine things I've ever worn, and I love the feeling of them.) Anyways, my mom would stand there and say "well... get up" because she knew that if she didn't see me get out of bed I would just roll over and go back to sleep, so I would just reach under the blankets and wiggle out of the bra and panties (or swimsuit) and into a pair of boxers which I wisely kept under the blankets just in case. She'd ask what I was doing and I would just tell her that I was finding my boxers, because they slipped down while I was sleeping. That trick saved me everytime thankfully.

I was kind of caught once by my sister. It was the olden days of the 90's when a family only had one computer, and it used a phone line to connect to the internet. It was a weekend tradition that whenever my sister or I heard each other start to wake up in the mornings that we would jump out of bed and race down to the dining room to secure that precious first turn to play on the family computer. Well, one morning I managed to win despite having to remove a "borrowed" bra of hers that I had slept in, I think I beat her to the computer because she went into the bathroom instead of going right to the computer as usual. When she came down to see what game I was playing she apparently noticed the clear and telltale marks of bra straps on both my shoulders. She went on and on about them, in an amused/disbelieving tone of voice. I tried to shrug it off and pretend it was nothing, maybe the bed sheets had wrinkled and made the lines but she was insistant that they looked like bra straps. Eventually she just said "weird..." and left me alone. A few minutes later I went back to my room and put on a t-shirt and vowed that I wouldn't go downstairs in just my pajama pants ever again.

Another time my Mom came in my room and just started going through my drawers. I was angry and protested a ton but she just made excuses and didn't stop. I knew that sooner or later she would come accross a few items I had stashed in the bottom of the bottom dresser drawer, and I just went downstairs and started watching tv, though I was freaking out on the inside. I never heard a word from her on the subject. I don't know if she suspected that I was doing a little crossdressing, or if she had just watched a "does your child do drugs?" special on tv or what, but the few clothes I had were gone. I never brought it up...
I like to think she rationalized it though. It wasn't a rare thing for people's clothes to get mixed up and end up in each others rooms. All our laundry was washed together and then sorted hastily by my father so I had a possible explanation even though she never confronted me about it.
  •  

Jessica Who

The closest I ever came to being caught was when I was a young kid and my parents and sister left for what was supposed to be a whole day excursion. Of course I took the opportunity to get dressed up in a cute bathing suit.

However, apparently they forgot something at the house and ended up coming back for it about 5 minutes later. I was totally caught off guard and as soon as I heard the front door open, I threw down my NES controller and shut my bedroom door as fast as I could!

My mother heard this and came straight to my door and knocked, asking me what was going on. I was holding the door shut and changing back into my boys' clothes. I hid the bathing suit under my seat cushion and then opened the door.

She was very confused but luckily I wasn't caught hehe. When I came out to her two Decembers ago she didn't recall that incident ;)
You know I dress for every situation
  •