I Just Had to Try It On ! Riskiest Item you Snuck in & tried on when you were Young

[Robbiegirl]

You knew you shouldn't do it but it was so pretty and you were so curious how you would look in it that you took a big risk and went for it !

One of my sisters had a friend come over that had just finished a tennis lesson and was in a cute tennis dress with ruffle butt panties. Later they were out at our pool in bathing suits so I knew the dress had to be in my sisters room. Well With little time to spare I got up to her room and there it was on the bed. So fun and funny to see myself in the mirror doing poses and then swing her tennis racket to see my dress swirl and my ruffles become visible. Suddenly i heard my moms car pull into the garage. Was out of the dress in no time but what a fun memory !

High Risk but high reward

[MsEva]

I have posted in the past that I have dressed en femme on a car trip from Southern Virginia to Northern Pennsylvania. A glorious way to travel. Not sure how risky it was in a long broomstick dress and boots but it sure felt risky at the time. I did underdress a few times in a corset and panties to do errands, but no one would see that. It was under my coat.

[CrossKimmy]

I know these types of threads get some ridicule about stealing, but I think we?ve all done that in our adolescence.

We had a family friend staying with us for a while and we were around the same size. So when she left for work, curiosity came over me and I had to check what was in her closet. That?s when I came across her lingerie drawer, specifically her babydolls. I just had to try them on. Of course I felt guilty for snooping but I had little to no access to such things at the time and my pink fog was out of control due to the puberty and hormones.

[JuliaGirl]

Always felt guilty ... neighbours house babysitting. Must have been 14. Hormones and puberty. Small kids in bed, the couple was always really late (1AM) and she was, thinking back on it, a stunningly attractive woman. Early evening, snuck into the master bedroom, had a peek in the dresser ... and jackpot! To this day I remember the assortment of lingerie. Had to try on several bras and panties, and then this gorgeous peignoir and glimpse myself in their mirror. Careful to put it back exactly as it came out of the drawers.

[evadan]

My Mom and I stayed with my grandparents In Southern California for about 6 months when I was 13. It wasn’t long after I had tried on my Mom’s panties that I had to start sleeping in the garage because there wasn’t any room in the house. So my grandparents fashioned a bedroom out of all of our moving boxes and things temporarily stored in the garage. One night out of boredom (or was I looking for something.....) I was poking around in some suitcases and found a small one stuffed with lingerie of my mother’s. Babydoll nighties, teddies, panties, bras. Needless to say I had no problem going to bed after that. Although I did almost get caught a few times when someone came into the garage to do laundry.

[candice.aihara]

For me it was purple bikini panties with small white stars on them. So cute and the fit was so snug; it was heavenly.

[ShelbyDawn]

I was in Jr. High School, about 14 or 15, maybe and my mom had brought a collection of formal gowns home for my oldest sister to try on, I was home alone and modeled each in front of the mirror, they fit perfectly on my skinny body. It was magic. I heard my mom pulling into the driveway and wouldn't you now it, the zipper on the last gown got stuck. I was lucky enough to get out of teh dress just in time to not get caught red-handed, but it was obvious that someone had been at least admiring the dresses.

And a related side story, at the same time I had a habit of stealing my sister's panties and wearing them instead of my tighty-whities, my mom even caught me a few times. A couple of weeks after the incident with the gowns, I found all my tighty-whities gone and replaced with men's bikini briefs in various colors, I knew my mom knew and until she passed, neither of us ever said anything. I still stole my sister's panties, though. there's just something about panties, right... :)

[Stephanie47]

Not the first, but, probably the riskiest was my mother's nylon nightgown. I shared a bedroom with my brother. Next to the head of my bed was a closet door. Right inside was a laundry bag with dirty clothes. I loved the feel of the nylon fabric. No thoughts about being a girl or anything like that. Just the feel. I would wait for my brother to fall asleep in his bed across the room which was only separated from my bed by four feet. I would quietly open the closet door and fished out the nylon nightgown, slip it under the covers and wiggle into it. I'd wear it for awhile before replacing it back into the laundry bag. To my knowledge my brother saw me do it or at least he never said anything. If my parents had caught me I'm sure my butt would have beaten raw. Years later when I did develop more of an interest in my mother's clothing I went through her dresser and tried on slip, bras, girdles, panties and stockings. I'm sure she knew one of her sons was messing around since I snap the strap on her one and only black bra.

[Crissy 107]

When I was 11-12 I started to wear all of my Moms things. We had a walk in closet with a light up on the 2nd floor and I remember wearing her panties, bra, OBG and sometimes stockings. I was terrified about getting caught but fortunately never did.
I guess that is my earliest remembrance of, hello, being in the closet.

[alwayshave]

Robbie, I have three older sisters, so I have been there.

[Tanya silk stocking]

Baby sitting at neighbours house and the lady was always a smart dresser so curiosity got the better of me and I had a look in her walk in wardrobe and there hanging up was a gorgeous ball gown with the ruffled underskirt and temptation got the better of me and had to try it on and fitted perfectly and since then I have had a think for buying them and last count had 20

[prettytoes]

I was about 14 and taking care of a neighbor's dogs. The daughter was a year younger than I, and I couldn't resist a peek into her closet. The pleated mini skirt just called to me...I just couldn't resist. I still remember how great it felt to wear that cute little skirt and prance around their house!

[Connie D50]

My mom was trouble about leaving thing's laying around in her bathroom. A blue teddy was just laying there I had to try it on with a house full of brothers and sisters (7). My older sister on the hand I think inventoried and organized her cloths. I still raided it I had to lol What i feel worse about my little sister sometime would get blamed for going into her stuff when it was me :heehee:.

[Robbiegirl]

For so many of us that started young it was virtually impossible not to try on a cute Babydoll if it was available ! Yes it was wrong but it was so fun !

Baby Blue Or Yellow were my favorite and of course they were so easy to fit into !

I doubt Girls have any idea how many of them had their babydolls modeled by boys !

[Kay J]

There was not a pair of nylons safe in a bathroom hanging up to dry in any house I was in just could not help myself!

[NancySue]

Like Kay J, my Mom?s nylon stockings hanging in the bathroom drove me crazy. I couldn?t resist. Mom thought I was sick because I spent so much time in the bathroom. I froze when I accidentally put a run in one of her stockings. Fortunately, she never said a word. I tried to avoid them, but like many of us...you know how long that lasts.

[Cheryl T]

In college I was dating this girl.
We were at her house and she had to go to work ... right next door.
Her parents were working and her younger brother in school. I was waiting in the house for her to come home for lunch.

Well I just had to try on her lingerie, so I did. Luckily I could see her work from her bedroom and I was just finishing changing back when she exited the building. A minute later she came in the house.
That was close...

[Cassidyjames]

When I was in my early teens my brother and sister-in-law moved back in to save for a house and she still had prom dresses and homecoming dresses and I could fit into all them! So when I had the house to myself I'd put on her panties and bras and model the dresses. I felt so amazing! Just so elegant feeling and that's when I knew I was a crossdresser and that I will always love dressing.

[Vicky_Scot]

The riskiest thing I did was when I went to my best pals house when i was in my teens. i went to the bathroom
and that was were the washing/laundry bin was. My nose got the better of me and had a look in and there was
one of his mums girdles in the washing bin. Without even thinking a stripped of and put on the girdle which was
so exciting and sexy.

Must have only been a couple of minutes before I took it off and got my clothes back on but it seemed a lifetime.
I stuffed the girdle back into the washing bin and left the bathroom. My friend never asked why I was so long or
anything thankfully. This became a regular occurrence when i went to his house and how I got away with it I will
never know.

X x x

[Teresa]

Robbie,
Guilty as charged on more than one occasion , I told some of the stories on the forum and got a real roasting so I'm saying no more !

[hosekid]

I see that people get a lot of negative feedback about stealing clothes, but I also know that it is a double standard. girls steal and wear their brothers and dads clothes all the time and no one says a word.

[Victoria_R]

For me it was my step mom's two piece bathing suit. I was young and my step mom was going to take me and my step sister to the beach to go swimming and I went to the bathroom to put on my swim trunks and there it was the bright pink bikini bottoms and top hanging. I put them on and model in the mirror I was so happy wishing I could wear this to the beach. Then my step mom knocked on the door asking what's taking so long and had to take them off really quick and hang them back up so she could get ready. I was so scared after that to see if she found out that it was not the same way she had it but she never said anything.

[April Rose]

When I was about seven, my mom, a war widow, remarried. Sometime after that, I discovered her wedding nightgowns in a box in the attic. Silky and gossamer, they were too much temptation for an already budding tranny to resist. I brought them down to my room and hid them under my mattress, intending to wear them in bed that night. Once in bed though, I panicked, thinking someone would come into my room at night and catch me. I got up and put them in the bottom drawer of my desk. Unfortunately, my new stepdad was in the bathroom next to my room, heard the drawer creak and came to investigate why I was out of bed. He looked in the drawer and found the nightgowns. To his credit, he didn't yell at me , but he just stared at me, and said, "son, I am very disappointed in you."


I remember to this day feeling like I'd done the worst thing in the world, and that my life was over.

My step dad left the room with the nightgowns, but then came back immediately and said, "do you want us to get you a dress and make you wear it outside for everyone to see?" He stared at me, but I couldn't even say no. I was frozen, too mortified to speak, completely lost in my shame. Then he left the room and nothing was ever said about the incident again.

Of course, the possibility that it would happen terrified me for weeks, and more and more ,as I approached puberty, became the stuff of masochistic sexual fantasies.

[JenniferR771]

My grandparents had a cottage with a old-time basement with doors to the lakeside. There were two rooms for changing to bathing suits--girls on the right and boys plus fishing tackle and outboard motors on the right. Adults upstairs, I found myself alone--and--I just had to try on my girl cousin's one piece blue bathing suit. Still damp--not dry since the last swim in the lake. So nervous--but loved it. Fit was roomy since my cousin was a bit wide in spots.

[Angela Marie]

My mother had a pair of blue tights (what today would be called leggings). I tried them on whenever she went out shopping, visiting neighbors, etc. I must have been 10 or 11.

[caitlyn louisa]

Live in GF was asleep one night and I went into bathroom and put on all clothes that she was wearing that evening. Tight black dress, lingerie, heels. Then i put on her makeup and hung out for an hour when she was asleep.

[Robbiegirl]

LOL ! Yes Jennifer there were rich friends that had the little pool houses and would nake old bathing suits available for guests ! Yes at least twice I took my time back there trying on the cute two piece foloral bathing suits ! So Fun ! Hey I was a guest so it was ok right ? LOL

[Ressie]

Anytime I apply makeup. The more makeup applied the bigger the risk because it can't be torn off quickly like clothes can.

[RainbowDash]

Once I went into my sister's room when she wasn't home. I took 1 of her bras and tried to put it on, with no success. I lost interest very quickly and thought to myself "Girls sure wear a lot of different things from boys." My crossdressing journey did not start until much later in life.

[Karmen]

Probably my mom's pantyhose. I was always afraid I would damage them and she would know she didn't do it.

[wendy]

I've borrowed a few article of clothing, but this is one of the riskiest :

I used to work as a student painter, and we would paint the interior of people's homes. At one house, the daughter was a real knockout, so when she was out and the parents were downstairs, I snuck into her bedroom and took a look at some of her clothing, I didn't take anything but she had a white see through body suit.

Another time, we were working on this person's house, and he stepped out. By chance I was the only one left in the house, so I went to the daughter's bedroom and found a really nice sexy one piece swimsuit. I quickly locked the front/back door, and tried it on. I saw a picture of her and was pretty good looking, a little heavy set though. Which meant her swimsuit was a little bit bigger on me.

One house we worked on, the g/f of the son moved in with his family. The son was not home, but the g/f was. She didn't unpack, and had all her clothes still in a white garbage bag. As luck would have it, everyone was in another part of the house, so I quickly went thru the garbage bag and found a really nice one piece swimsuit. I smuggled it home and tried it on. It was nice and tight, and felt really good. I had every intention on keeping it, but my conscience got the better of me and the next day I returned it. That was risky, as I noticed she dumped all her clothes from the garbage bag on the floor the next day.

back when I was young and stupid ...

[Alice Torn]

Risky things i put on were my sister's swim suit,and her panty hose, which i ruined badly. I am sure she must have noticed, and suspected me. My mom's nylons, too. Noone said what happened, but my mom did want me to go to a "shrink" about that time, and i would not go. I think they knew.

[penny lace]

I was very naughty as a child tried on most of my older sisters underwear, all of my mums nice underwear, dresses and skirts as well as quiet a bit of my aunties and cousins. Needless to say caught out numerous times and made to promise not to do it again.
But the most risky was when I was around 17 staying with a friend while his parents were away and had a bit of a party with friends. I got drunk early and went to bed early in his parents room. Inevitably went straight to find his mums underwear drawer and once found it pulled out a lacy little baby doll and so quickly in to that and in to his parents bed. Scared to death when my mate came to check on me never pulled a duvet so tight to my neck in my life!:o

[Ashlee]

Hmm. as a pre-teen and teen I only had my mothers clothes to wear, i never touched her undies however. I house sat for my friend and dressed up in his mothers clothing and had the run of the house for a week, it was glorious but riskiest I'd say....Aunt and Uncle asked me to house sit when I was a teen. I went about putting on a lot of her clothes when they were gone and stayed dressed for hours but when i had a moment alone and before they left I was able to put on her panties, bra and pantyhose from the hamper in the bathroom in anticipation of them leaving as I'd get down to business and dress including makeup. I had these items on and was watching tv when they came home to make sure I was all set w/the home etc. I was sitting on the couch in male clothes and rock hard underdressed waiting for the green light to dress, they sat feet away for what seemed like eternity. If they'd asked me to get up and hug it'd been game over as they'd feel the bra strap.

[Robbiegirl]

Ashlee the bra has always worried me when I thought about underdressing.

I wonder how many of us had trouble getting out of dresses when the zipper got stuck ? LOL