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As much as this lifestyle is full of angst and anxieties, it can also be wonderful, exciting, and full of “Holy *%$#” moments. Can you imagine a television show like “America’s Funniest Videos” dedicated to all those moments of panic-stricken, hilarious mishaps, missteps, and running for your life when you are about to get caught, crossdressing escapades?
How many of us have done things for the sake of our fixation that we wouldn’t have done otherwise? I’m guilty…big time. I’ve had some close moments, scary ones, and each one laughable as I look back. I’m not sure if my mother was naïve or just not willing to “go there” when I was in my adolescence. She had a dress mannequin (The bust on a stand) for making clothes for my sister and her. I used her makeup on the Styrofoam head and put it in my sister’s room (she is 8 years older than me) complete with a long dress and shoes poking out. I was 10 at the time and infatuated with my sister’s clothes.
I even put a bra on the mannequin. My explanation was that I was trying to scare my mean sister. Later, in Jr. high, I got my friends to do a “Vampire Short” for my media presentation. I had my male friend dress in my sister’s clothes and wig to play the girl…I was the director, and very jealous. He looked really, really good. I got an A. In High school, my friend in the neighborhood had a divorced mother who liked to look good. She had a closet full of beautiful, silky dresses and pantyhose. I got to take care of their dog when they were gone, and I tried on every one of those dresses…even (I’m ashamed to say) nabbing two and bringing them home…stupidly putting them in my closet. I didn’t think my mother would snoop in there…she did.
I confessed…it was my friend’s fault. He wanted to run away and was going to hide out in disguise, so I was keeping them for him. Mom only told me to give them back. Did she, or does she know?
I used to hide a wig, pantyhose, a bra, and panties in a gym bag along with some other confiscated dresses and shoes. I had a tent set up across from my house on an island (grew up by a river). I could dress and hang out in the tent during one summer…until someone came along and found the bag. It was a neighbor scoping out potential deer stand placement. They took it to the police as it might be the clothes of a missing girl from a few years back. Luckily, nothing ever came from it. If there was gossip in our neighborhood, I never heard it.
The early years of marriage were an adventure in stealth. I’ve only been caught twice (You can read about what happened to me in my other articles). My ex went to work, I was home for the day, and I wanted to try on her prom dress. I could only zip it halfway and she came home to catch me. I ran to the bedroom and took it off but had to confess. From then on, I was much more careful as I solemnly swore to never, ever do it again. I hid a pair of high heels inside my workbench or in my golf bag. The shoes were a purchase that I had to have. I walked by them in a mall multiple times before mustering the courage to buy them. They were a size 10…I wear a 13, and I made them fit until I broke a heel and had to throw them away.
I was riding my bike and happened to pass by a car. The windows were down and in the backseat was a pair of clogs and a purple dress. Yep, I eventually nabbed them and neither of them came close to fitting. I always wondered what the girl must have thought. All those things that we can’t stop ourselves from doing to feed the need that burns in us. Thankfully, I saw the light and have made amends by donating thousands of dollars of clothing and accessories to thrift stores…much of which I wish I still had…Damn those purges.
Some of the more humorous moments… I once got “STUCK” inside a dress that was way, too small. My arm was pinned, the dress cutting off my air, and panic taking charge. I danced…more like flayed across the room trying to get it off. I couldn’t see and knocked a valuable knickknack off the shelf, fell on the floor, and couldn’t get back up. It couldn’t have been more than a few minutes at most, but it felt like forever until the seam gave way and I burst forth like the Hulk. I paid $2.00 for that dress at a garage sale. It would be years before I understood my size and that I wasn’t a pretty and petite girl.
I tried to run in spiked heels once when the dog started barking and the doorbell rang. I severely twisted my ankle and had to crawl to the safety of the bedroom. To make matters worse, I also popped a blood vessel on my finger, the one wearing my ex’s ring. I barely managed to get it off, and not without some major pain. The ankle became one of those “lies” we tell to cover up. I fell down the stairs, oh clumsy me. Okay, I did actually fall down the stairs once wearing heels. I was lucky not to have been hurt.
I was once asked if I had been wearing mascara because of how dark my eyes were. “Nope, had a bad night sleeping.” I’ve split more skirts and dresses trying to fit into the wrong size, broke straps on shoes, spilled all the birdseed out of my homemade nylon boobs--everywhere, scrubbed my lips raw to get off a staining lipstick, deodorized the house after using a strong scented perfume, forgot to put jewelry away and tried to ignore it while talking to someone (hoping they don’t notice it or my anxiety), dove for cover on the floor behind a couch when the nosy neighbor knocked on the door and looked through the living room window, lost an artificial nail and spent hours looking for it so no one else finds it (was inside my pantyhose), lost a bracelet and couldn’t find it, got mascara in my eyes, (cold crème too), put a run in the ex’s pantyhose and stained her dress with her own lipstick.
The list is endless…and priceless. Like women and girls, we have to learn from our mistakes. I found better hiding places, learned how to apply makeup, do spot treatments on garments, buy the right sizes, and eventually come to terms with who I really was and am. I’m more than a crossdresser and I deserve to be happy and content in that acknowledgment. Not me, and not everyone can be “Out”, so we have to find our own particular balance, our own means to survive.
I’d love to hear some of your stories. God knows we could all use a little laughter.
Be safe, be kind, and may you find a closet that is large enough to hold your wishes and one with good lighting…
Until next time….
Thanks for the laughs!! If only tik tok was around back then and your phone was filming every minute.... those experiences are priceless!!
I got stuck in a few dresses in fitting rooms. Always felt more panic and sweat kick in, but eventually escaped the dress. Ripped one once, hid it back on the rack.
Heard the distinct rip of a tight dress at home a few times. Snapped many spaghetti straps bulging under my manly chest.
And.... had a teenage boy moment trying on some tight fitting pants in a thrift store. Hid that on the rack, hope my DNA doesn't end up at a crime scene. That one I am ashamed for, but it is funny later.
You had me smiling:) We can scare ourselves more than any can. I'm glad I don't have to watch the clock or listen for the sounds of the garage door opening. Thanks for sharing!
Definitely true, embarrassing, and yes, funny. I enjoyed the article and had some great laughs, at your expense, thanks for posting
My biggest one was thinking my sons didn’t know about Bobbisue. When I finally admitted I was a crossdresser, my oldest son said he and brother knew. He had asked me for my old cellphone, which I gave him for his son, never thinking that I had a picture of me en femme on it. Ouch! Not smart...lol
Happy you enjoyed it. After my embarrassment, I had to laugh myself
Thanks for such great article Sabrina! Wow, what a time you have had with mishaps. I have nothing like the those stories to share.
Maybe, and this isn't an accident one. I used to work in the print business and for a time was in charge of a neat fabric printing machine, doing custom printing for various advertising promos. This one time we were doing a promotion for a Barbie launch of some kind, and my part was making yards, and yards, and even more yards of pink spandex! Well, one has to run tests and samples to get the colour correct, as it is a specific pink, so I collected the waste and brought it home and sewed myself a mini dress out of it.
When we moved of course we threw a lot of stuff out, but I just had to keep that! Not that I know where it is right now, or if I'd even wear it again.
My dressing has evolved so much since then.
I could see myself making all kinds of pink outfits or accessories. Half the fun of getting to that place where I can look decent was trying out all the looks that made me look comical. I have a great appreciation for women and those of us who know how to "shine" in their own element...
thanks for the story 🙂
Thanks Brina. One of my close discoveries ws when I was in high school. I am the oldest of 5 brothers, and one afternoon and was playing alone in my bedroom ( playing super heroine). I don't remember all I was wearing but I do remember mom's discarded pantyhose and an old towel for a cape. I think maybe I had an old top of her's and fake boobs (rolled up socks). As I was enjoying the look and feel I heard a couple of my brothers coming up the stairs toward my room. In a panic I slammed the door shut and pushed on the door to keep them out. They started yelling at me and pushing the door from the other side while I was panicing on the other side not being able to hold the door well because the pantyhose on my feet couldn't get a real hold on the wood floor. After a couple of minutes of nearly getting in they gave up and I was able to get out of the situation.
. . . .Cassie
Great one...had me laughing. I could really visualize it! Thanks for sharing 🙂
So many familliar experiences Brina. Had a few close calls that thinking about it now must have been suspicious. Usually items left out or not put back correctly.
Had the lost nail a couple of times. Luckily found them but couldn't imagine how I could explain that.
Traces of mascara once. Had to say rubbed eyes with oily hands.
List goes on and always very nervous still if been dressing around house to make sure all is tidy.
Jane,
Oh yes, the panic of being down on hands and knees searching for that allusive nail. How am I going to explain it? I believe we all find some really creative ways to hide our "stash".
Thanks for commenting 🙂
Hi Sabrina! That was a fun read! Thanks!
Oh, the thieving I did too as a youngster! Nothing major, just a few pairs on nylons, but I too have made many amends and continue to do so.
Many years ago, I got caught in my white pantyhose, matching babydoll, elevated slippers, and a hint of make up by a very masculine and aggressive uncle. I thought the house was empty, so I Ieft my bedroom door wide open. Duh! I thought he was going to beat me senseless knowing his fierce reputation. We both froze as we looked at each other. He broke the ice with a sincere smile and just walked away. We never spoke of it and his behaviour towards me to this day is as kind as any favourite relative can be! Who knew?
Barb
Wonderful story! I think it goes to show that we really don't know who might be inclined to be accepting towards us. It isn't suspect to think that many men have either wore an article of female clothing or really wanted to. How many husbands have resisted the urge to try on their wives ' bra and panties, negligee, or even their clothes and shoes? Maybe their lipstick, you know, just because...
Thanks for the comments 🙂
Such a great article and yes, I mimic so so many of your stories. I too could write a book. And yes, I've become quite adept in running in high heel shoes.
Hugs
Danielle
A practice that is important and necessary...lol. I always wanted to join in the high-heel race that I've seen posted online. Not sure where they hold it, but I think it's to benefit cancer.
Thanks for commenting 🙂
Hi Sabrina
I really enjoyed reading this article of yours it had me smiling, laughing, grimacing and at time all three at once
I really can’t match all your “experience’s” but one does spring to mind, It was over over 50 years ago when I was around 10, my mum had a wonderful pair of boots that I longed to try on so one day I had a rare opportunity to do just that, mum and dad had popped round to a neighbours for a cuppa and my brothers and sister were all out so I sneaked up to their bedroom and grabbed the boots put them on (Wow they fitted like a glove) so I take a walk around the house really enjoying the moment and of course I herd the back door opening so in a panic and struggling to get the boots off which, by the way, definitely seemed a lot harder to get off than put on! lucky I just got them off and shoved them under the sofa before mum came in the room. It was such a close shave but not the end of the story (sorry!) mum didn’t return to the neighbours so I couldn’t return the boots straight a way, I did get a window of opportunity a few hours later so I crept back to retrieve the boots from under the sofa but they weren’t there! And to cut a longer than planned story short, nothing has ever been said since about the boots and how or why they got to be under the sofa? One thing I do know is that mum certainly knew Who put them there!
Stephanie x
Aren't mother's wonderful? I always figured that mine knew but remained silent. She's never said a word and neither have I. It was my sister who had a pair of black Mary Jane shoes that held my fascination. Just when my feet grew enough to fit in them, she took them with her when she moved out for college. That was also during my really pudgy stage and I couldn't fit into any of her leftover clothes, or my mom's. My dreams were wishes as I looked through the Sears Holiday catalog.
Great story! Thanks for sharing 🙂
I think the most exciting part of crossdressing is the adrenaline rush of being outside the box and being at risk of being "caught".
In some situations I managed to avoid embarrassing situations.
One day at school I ran away so I wouldn't get a hug. The reason? I was wearing my sister's bra. I was afraid someone would touch the bra.
Ha! Love it. I know that feeling. I've been underdressed and encountered those I know. For me, along with the bra it was also the wearing of perfume (not freshly applied but the lingering scent) that had me worried. Thanks for the story 🙂
Thank you Sabrina
Your Stories are true too life events I think we all have experience.
Thank you again
Jennifer Ramirez
Another fine, fun, "slice of life" article. Thank you.
I also struggled through trial and error to find my sizes. I've heard the "pop" of a seam giving out and thought, "oh damn, I've done it now" but nothing ever came of it.
I've felt the panic of hearing a car door slam when I'm decked out to the nines.
I've been caught with pantyhose or lipstick in the grocery wagon, "now how on earth did that get in there?"
Let's not even mention the times my browser history has nearly outed me.
I guess it's all part of the crossdressing experience.
Hugs, Jillian
Girl, I can relate to all of those. Thank God for automated checkout at Walmart and other stores, not to mention the plain Amazon boxes for delivery. I once ordered from Fredricks of Hollywood and had to get to the mail before anyone else (so no one would notice the box.) Talk about anxiety. Now you can track it online.
I broke the strap on my wife's shoes and manipulated it perfectly so it would appear that she did it the next time she put them on. I even managed to sew up a tear in one of her sweaters with the right colored thread.
Great comments 🙂
I broke the heel on a most lovely pair of thigh highs one night. They don't make the best running shoes.
I tried to fix my one great pair that I mentioned in the story. It was a disaster. I still wore them for a while (only one heel and the other glued in place without me putting weight on it) until I nearly twisted an ankle again. It was a sad day when I buried them unceremoniously in the trash.
Thanks for the comment 🙂
Thanks Sabrina for the fun article, I think it’s something we can all relate to.
I am completely in the closet, no one to my knowledge is aware of my feminine side, except a few cross dresser friends. I had an unusual close call that involved technology. My social media presence for my fem side is on Flickr and YouTube, and I occasionally post videos of Kelly on both. I have a few videos of me on the beach. The day before I had been broadcasting YouTube videos to our flatscreen TV from my IPad (nothing related to crossdressing, I know better than that). My spouse was watching TV, and I was in a bedroom on my IPad doing something on my YouTube channel. My finger accidentally brushed across something on my IPad, and I suddenly realized that a video was playing. But it wasn’t playing on my IPad, it was being broadcast to our large flatscreen TV my spouse was watching. I had forgotten to turn the broadcast feature off from the previous day. I tried stopping it but it didn’t respond. I looked out of the bedroom down the hallway and there I was, to my horror, on the screen in a one piece swimsuit (fortunately wearing sunglasses). I finally got it to stop, it must have run for about 10 seconds. I walked out and calmly apologized to my spouse for interrupting her TV (no pun intended), and explained that I was watching a video that was accidentally broadcast to our TV. She only seemed slightly annoyed that I had interrupted her program temporarily, and also probably didn’t appreciate that I was looking at videos of women on the beach. She resumed watching her program and that was the end of it.
I was relieved that nothing came of it. If it had happened to be a video with our furnishings in the background, I would have been outed. While I didn’t think there was anyway someone would recognize me in this particular video (the sunglasses helped), I am fairly positive she didn’t even realize it was a cross dresser she was watching.
I have had a few close calls in the past (who hasn’t), but they always involved something physical, like traces of makeup or almost running into some neighbors when out and about. Technology is amazing these days, but be careful when using it.
Hugs,
Kelly
Such a good story 🙂 Technology was my downfall. I ordered a pair of white platform 8-inch stripper shoes (back when I was married) and a babydoll nighty with white fishnet stockings. I was overweight, hairy, and took suggestive photos of myself. I copied them from my camera to the computer (into a special folder). I looked at them (they were awful) and deleted the folder, making sure to empty the trash. I rebooted and double-checked. They were gone. To my horror, the absolute worst picture somehow ended up being put in a folder where my ex pulled it up. She threw me out of the house.
Funny thing...was it an accident or divine intervention. We were headed to divorce sooner than later. This just became the catalyst that set me free...I only wish that it had happened much sooner.
Thanks for sharing!
I have tons of tales, many involving police. But a favorite is the time I was traveling to a crossdresser meeting and let my girlfriend drive in heavy Greenville I-85 rush hour traffic while I called others to say I would be late for the dinner I was hosting. It was stop and go traffic. They stopped. She went. The car was totalled. Police arrived to pull us to the other side of the highway. The wrecker arrived as the police were taking info from me. Traffic was at a standstill and all were gawking at me.. It was at that point that my skirt dropped to the pavement. I'm sure the eye in the sky reported it on the 6 o'clock news.
On another occasion I was driving a rental car in St. Pete en route to church on Palm Sunday. It was a 35 mph zone but my GPS said 45. I was going about 50. A copy facing me at a light made a quick u-turn and pulled me over. I had no license and no rental car papers with me. I figured he'd trace the car and find my male photo, deducing I was stealing the car and I'd be pulled into the slammer for grand auto theft. I could imagine the laughter when the arresting officer announced "Look what I caught today!" Unbelievably I got only a warning. That would NEVER have happened in male attire! A friend who works with the police later told me it was probably because they did not want to throw me into jail to be harrassed and assaulted.
My God, you've had some moments... I got my heel stuck on the accelerator once and was using the other foot to press on the brake to fight the acceleration. It was a scary moment and one of those lessons learned.
Great stories 🙂 Thanks for sharing!
I got my heel stuck in the space between elevator and the floor once. Elevator took off and I landed awkwardly. Fortunately the heel broke off. It might have been worse.Heels can be dangerous!
