Stories Of Crossdresser

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Stories Of Crossdresser
In this week’s crossdressing stories series, I’m going to talk about how I started wearing heels!
I’ve mentioned on my YouTube channel that I discovered my passion for wearing heels by watching my mother strut in her’s, but never went in-depth .
You see, growing up my mother did her best to raise me in a Christian environment. Not only this, but she was adamant about raising me to abide by gender norms and expectations.
I feel like this was largely because she was raising me as a single mother, her only child, so she wanted to “protect” me. Little did she know, that restricting me from exploring my interests(like crossdressing) was hindering my confidence.
As any true cross dresser would do, I’d often sneak into my mother’s room(when she was at work) and try on every pair of high heels that she had. This was exciting for me because I got to feel what it’s like to wear heels for the very first time.
Each time that I got to wear a pair of her heels, the more empowered I felt to refine my skillset .
I can vividly remember wearing a pair of her black six inch stilettoes with a thin bow-tie around the toe opening. They had a small reflective platform and I was obsessed with platform heels as a kid, so needless to say I literally wore the shoes out .
My mother’s measly size eight shoe size compared to my thirteen at the time(fourteen now) eliminated her high heel’s chance of surviving my puberty saturated fierceness .
One day my mother came home and was getting dressed for bible study later that night. To my horror, she picked up the pair of black platform stilettos that I had stretched out with my feet the day prior and was about to put them on !
Of course I threw my PB&J sandwich across the room and ironically hid in the closet while she slipped on each heel. I knew that she would realize a mini sasquatch was in those shoes, and I was the only culprit .
Slowly but surely, her distressed realization to the misfitting of her heels came into fruition. Suddenly she screamed, “Was you wearing my heels boy?!”… my stomach sank accordingly.
I had nothing else to do but tap into my emergency store of creativity. I had to somehow convince her that a mini sasquatch was actually in her heels!
Fortunately, my ability to think quickly lead me to telling her a story about how I lost a dare and had to wear her stilettos. She believed me and said not to do it again.
I stayed away from her shoe collection up until the point she bought a pair of adorable platform wedges. These heels had a boho chic design and were sandals so I had enough wiggle room to walk in them without causing damage!
That was my short story about the time I started wearing my mom’s heels! It’s always fun to recount these stories along my high heel wearing journey, especially considering how far I’ve come(follow me on instagram) .
If you’re looking for some awesome heels, I got you covered! Check out my post 21 High Heels For Men You Can’t Find In Stores to see some of my favorite heels online with large shoe sizes. When I started my high heel wearing journey, I struggled to find heels for men. This is why I’m passionate about sharing my new findings with you!
Feel free to let me know how you started crossdressing in the comment section!
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Copyright © 2022 · HeHeels · Hello You Designs

Featuring the fabulous and stunning Theona Staind from Romagna, Italy as our CoverGirl of the ...
▶ Femme name: Alana Grant ▶ Location: Peru ▶ How long you have been crossdressing ...
▶ Femme Name: Kristy ▶ Location: Louisville, Kentucky. ▶ How long you have been crossdressing : ...
Charming crossdresser Sylvia Greene shares with us her 5 most favorite outfits & style ideas. Outfit ...
My name is Bert and one of the most embarrassing moment of my life transformed my whole life which I will cherish forever. It really opened my eyes to a whole new world for both me and my lovely wife. I have been married for over 3 years and I am a straight guy who always fancied women. But after this particular incident, I was completely transformed.
It was quite a normal day as usual. I woke up, had breakfast and took a shower. Then as I was getting ready to go to work, I heard a loud bang outside. I called my wife but she had already left for work. I got curious to check out what made such a racket outside.
I only had a towel wrapped around me and I proceeded to go the back yard. It was quite breezy outside and just as I got out to inspect what happened, the wind sucked the door closed catching my towel in the process. I tried to open the door but it was too jammed with the towel somehow.



So, here I was standing at my own backyard in all my glory and the door was completely jammed. I didn’t know what I was going to do to get out of it. Going around the front completely naked would be just to ridiculous as the street would be busy with people leaving for work. I started to get a bit nervous , standing there without any clothes on and just covering with my hands.
Then I started looking around and my eyes caught sight of my wife’s undergarments hanging on the line. I was quite nervous, so I rushed and grabbed one of her panties. I had to cover up with something as there was no other alternative. I put the panty on and just wished no one would see me like this. Then taking a deep breath, I ran for the front door as fast as I could. Luckily, I managed to get to the front door and finally inside the house without making any scene. When I got inside, I had a quick laugh and couldn’t believe what had really happened with me.
I went to the kitchen to get some coffee and for a moment I completely forgot I was still wearing my wife’s panty. I only noticed it after I started feeling a little aroused from the silkiness of the panty against my male parts. It was crazy but I was really enjoying how the panty felt on my body.
This really got me quite curious and I thought that maybe wearing my wife’s panties was turning me on somehow. The day was getting quite adventurous and I felt like skipping work that day, so I called in to work and said I was going to take a day off because I wasn’t feeling very well.
The rest of the day, I browsed through my wife’s wardrobe and tried a lot of her stuffs. I had no idea where it was coming from but the excitement was something I had never felt before. I tried on her pantyhose, bra, some more panties and few of her lovely dresses. I looked at myself in the mirror and I felt so feminine and my whole body was experience such a tingling sensation like I had never experienced before.



I completely lost track of time and only when I looked at the clock, I noticed how long I had been dressing up in my wife’s stuffs. I put everything back in her closet and went to the kitchen to get sometime to eat. I just couldn’t stop thinking about how lovely it felt to wear those things of my wife.
When my wife was back from her work, I told her about the morning incident where I got locked out without any clothes and how I put on one of her panties to get in. She really got a good laugh and asked me if I enjoyed wearing her panties. I admitted I did. I could see that her eyes had gotten bigger with excitement as I knew she enjoyed role playing a lot in the bed room.
She then asked if I wanted to put on one of her outfits for her and I said why not. She was super excited. She took my hand and we both rushed to the bedroom. Then she started taking out all these stuffs from her wardrobe, a bra, panty, pantyhose, a lovely blue gown and a pair of black heels. She told me to put them on. I got a little nervous as this was something I had never done before but she seemed to be really enjoying herself seeing me like that.
After my wife helped me to get dressed, she looked at me and told me I also needed some nice makeup to go with the outfit. She said she wanted me to have a full experience of being a woman from head to toe. Then she started applying makeup on me, which too was a completely new experience for me. She put on some foundation on my face, then applied some eyeliner and lastly added pink lipstick on my lips.
She also had a few hair wigs from Halloween and decided to make me wear it too. She went to the store room and was back with a nice long hair wig in her hands. She helped me put them on and flipped my hair to one side. Then she zipped the back of my dress all the way up and I was so excited to wear a gown for the first time.



When I looked into the mirror, I couldn’t believe it was me. She was surprised at how good I looked as well. Then she told me to put on the heels and I did. I was completely mesmerized by how I looked and how I felt dressed as a woman. It was quite wonderful and I felt totally different than my normal self.
My wife knew I was enjoying getting feminized as she could see my budge under the dress. She then held me near, kissed my lips and we both made love in the bed. It was one of the most intense love that we had ever made and she also noticed it.
After we were done, she then asked me to go in the living room. Walking in heels was not easy but I managed to go downstairs and in the living room. We then sat on the sofa, drinking some coffee and she asked how I felt being dressed like a woman for the first time and how it felt to walk in heels and so on. We just talked for hours.
She even joked that we should head out to town as girlfriends and see if I can pass. It was crazy how a simple incident completely lead to a totally different scenario and that is how I became a crossdresser. After that, my crossdressing journey started and it has been a wonderful experience since then.
I wonder when the strap on will come into play ?
I’m a sissy since i was 5 yo i’m start dresding with My mom and My sister clothes and My mom lingery and i.nevet Say nothig to My mom because i was afraid and in México was very homofobic in that times and never been hormonize and i’m alwas be have in a cirgury to chenge My frce in to a womens face and My body and have boobs anda beautiful ass but now i’m 48 and i don’t know how to make up and still look like a boy can You help me to look more femenin and look pretty and femenin
When the feminization and first time.out,. In my case, I always wanted to crossdress. My wife only word no.
My wife and her caregiver, she had a broken toe. They planned a Halloween three days get together. Friday through Sunday. Three couples
Thursday after work. I was ushered into the bathroom. She told me to strip.. Now you have what you wanted. I’m your dominant mistress and your my submissive whatever title I want wife, girlfriend.
She placed me in the shower. Got my body wet. She then told this would be last time I would have any male body hair. Ten minutes later totally bare.
She said,(” I’m glad, you have same size feminine body as mine. You can share my wardrobe. Think of all the nighties you bought me.”)
Lavender panties with maxi pad to make it more feminine. She slid them up my legs. Push my penis down and the pad held it. Padded bra pantyhose, Blue pants suit. Then makeup And finally blond wig.
I look in the full length mirror. No.sight of any manhood
She said How do you like the look Katie. I guess that’s my new name.
I was handed a black purse. Car keys, wallet, cards and lipstick.
She told me a Walmart.list is in your purse. She opened and handed it to me. I made sure I could read it
Six items. It covered.the whole store. Don, Lucy’s husband will there.
Carla said I wouldn’t be able to recognize her. It’s Donna now.
I left got there. Took a basket from the parking lot. No interaction with cart person.. Started on.list.
The clicking of my heels was annoying
Then from behind, (“Katie you’ll get use to it.”)
I turned around and, I said, (” Hi Donna,”).
We talked she.has been doing this six months. Donna thought my voice was better than hers. We went shopping like two girlfriends.
Paid for everything, got out. Donna said,(” One thing, take your lipstick out and compact out. Put more on and then you can go.)
Got home I thought 5pm home and now home again 9pm. Feminized, dressed and out in public.
I’d totally enjoy having a girls day at wall mart.. you’re soooooo lucky!
Well, why will readers be so surprised at this after all all, all men on this planet start their life as female and then a few get converted to male for the sole perpose of procreation.
Now, you not accept this so ask yourself these two questions, (A) why doe men have nipples we do not feed babies, (B) why is it that men can catch and die of breast cancer. It is that bit of female that we start off with that is in all of us in varying degrees and that is what governs who we are and what we turn out to be.
Education is what is needed so that a better understanding on the male condition in all its forms cant be understood by all.
I love dressing like a women, i love bra ,gaine , pantyhose, dress and i go in the street like this.i go to the lingerie shop and buy lingerie
Many years ago, my wife, out of the blue, started to put some makeup on my face and dressed me in her long slip with a towel covering my short hair. Then she took some pictures. Another time she painted my toenails red. They were red for 2 weeks – she didn’t know it but I actually touched them up where needed! She never did anything to take the polish off! Eventually, I unfortunately did this myself. Whenever she sees men dress up like woman on TV, she always laughs at them. I think that the cross dressing, etc., turns her on! So these stories that we are reading actually could be real!
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Featuring the fabulous and stunning Theona Staind from Romagna, Italy as our CoverGirl of the ...
▶ Femme name: Alana Grant ▶ Location: Peru ▶ How long you have been crossdressing ...
▶ Femme Name: Kristy ▶ Location: Louisville, Kentucky. ▶ How long you have been crossdressing : ...
Charming crossdresser Sylvia Greene shares with us her 5 most favorite outfits & style ideas. Outfit ...
Since childhood, I was always fascinated by women’s clothing. I used to secretly put on my step mother’s dress s and liked feeling pretty and girly. I tried to stop those urges but it only grew bigger.
As time went by, I started to sneak into my step mother’s room more often. I tried on her outfits, her makeup and shoes. So, every time I was going to be alone in the house, I would simply dress up. I started to buy outfits, lingerie, hair wigs from online stores and kept everything hidden in my closet.
One day my whole family was going on a trip to one of our relatives. I somehow managed to stay behind, saying I have a few tasks to finish. It was a great opportunity to take the whole house to myself. So my parents left and I was so excited to get dressed. I really wanted to wear a full make-up from head to toe and spend as much time as a girl.



I started getting ready without wasting time. I started with makeup, then undergarments and a pink bodycon dress that I recently brought in. I finished my transformation with a blonde wig, pantyhose and high heels. It was surprising to see my reflection in the mirror as a girl. I thought I looked cute.
After I was ready, I walked around the house in my new outfit. It felt really great. I took so many photos and videos that I did not understand how time passed. My parents were only coming back the next day, so I still had time to spend as a girl.
I had been out to the backyard several times dressed before, but it was only for a short time.
I walked into my backyard, feeling a little nervous if my neighbors saw it. So I looked around until I was comfortable. After confirming, I set up the camera and started shooting.



I noticed there was a boy looking after me from the neighbor’s house. I didn’t know how long he stayed there. I immediately panicked. My heartbeat got faster and faster. But I still tried not to overreact. I simply and slowly entered the house.
I was terrified that my cross-dressing secret would be exposed and my family would find out.
Soon the boy rang the bell and entered the house and kissed me. I was now a boy’s girlfriend.
Awesome story. I actually kind of liked that you ended the story with saying that you’d become his girlfriend and let the reader’s imagination fill in the rest of the story after you two disappear behind the closed door to experience intimacy in private. Loved it!
I loved it when he kissed me. It opened up a new world for me. Not only was I dressed as a girl, but now I was loved by a sweet little boy. Oh, what I could do for him! Mmmmmmm . . . . . .
Miss Roxanne Lanyon
I hope you DID do it for him. And he do it to you… Uh, for you.
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