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I Remember My First Crossdressing Experience

I was 4 and my mother asked me to help my sister (who was 5 years older than me) with the laundry. In one basket I was carrying were several pairs of panties; some were my sister's. I know this because she told me that she had been asking for a long time when she could wear big girl panties (nylon) like mom and stop wearing those horrible little girl cotton ones and mom finally got her about 12 pair. She was so excited that she showed me every one!
"Ha-Ha! You have to wear dull, boring boys cotton underwear and I get to wear soft, pretty nylon panties!" she teased me. "I bet you'd like to wear these if you could." she said and said I could try them if I wanted. I said sure, they were pretty & soft, and she let me borrow 2 pair. I took them into my room and took off my boy clothes and put on a pair of panties ... I was hooked from that moment!
My formative years were filled with my sister loaning me her lingerie as she got older while I still "borrowed" mommy's panties every so often to help my budding libido!
Nylon is the best! I wear layers whenever I can. Panties, pantyhose, half-slip, bra, full slip, skirts & blouses. I sleep in nylon nightgowns or baby-dolls, pantyhose & bra whenever my wife is away visiting.
I am 63 & I have been a life-long crossdresser. I no longer consider it crossdressing, I have since changed my thinking to allowing my feminine side to emerge. My feminine persona is who I am most comfortable being. I don't understand why girls don't want to dress feminine, these clothes are so comfortable! IO would wear them 100% of the time if I could!
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Felt really great didn't it, it did for me too when I was home alone and tried my mom's pantyhose and mini skirt for the first time, I too was bitten hard by the cross dressing bug and never looked back!
Jessie407 · 70-79, M
@wtbwoman I take it you went the whole way & had the surgery to become a woman. I never wanted that, I am not into guys at all, I love everything about women, including their clothes.
@Jessie407 I haven't transitioned yet, I hope to start the journey sooner than later.
Jessie407 · 70-79, M
@wtbwoman If you're into girls then why not stay a guy & be a crossdresser and find a girl who supports that side of you?
However, I can understand your desire to become a woman if you're into guys.
If you're into both, well that leaves all options open, doesn't it? LOL!
cd4259 · 61-69, M
Hugs & kisses Jessie, I did not have a sister so always snuck Mum's or cousins etc. But like you have loved nylon since I was a kid & still wear nylon panties 24/7 today
Jessie407 · 70-79, M
@turbineman40 WOW! I just realized how long it's been since we last talked!
Forgive me, things have been absolutely crazy for me!
I have had several hospital trips (with cellulitis, seizures & covid) & in this time, I have gained about 100 pounds due to my inability to move freely.

But, to your question: No, I have not found a partner to crossdress with. My wife hates the idea & she refuses to accept it. I can only dress when she's out for several hours or away visiting family or friends for a week or longer.

Plus, we have a border who is in between losing their house & finding an apartment.
I have absolutely NO private time!
turbineman40 · 80-89, M
@Jessie407 well, it is good you can find some time for yourself. Sorry to hear about all that has happened to you. Hope things are getting better
Jessie407 · 70-79, M
@turbineman40 I would LOVE to find another guy to dress with, as long as that's all the further it went - dressing. I am not interested in sex with men.
My ultimate hope is to find a woman who understands & will help me dress & even shop for feminine clothing with me.
We could have a girl's night out shopping, dining & maybe even sex in the ladies room.
I was five when my cousins dressed me up in some panties. Loved them then and now.
SilkandLace2 · 46-50, M
Full nylon briefs are simply DEVINE, still my favorites!!❤️
SW-User
I never had a sister to share clothes with and so I'm quite envious of you. Your last part is so true women's clothing is so much more comfortable
runlikeanantelope · 26-30, M
So wonderful sounds a lot like me!
Majorsite · 61-69, M
Love Your honesty !
Ozdharma · 61-69, M
Randie · 61-69, T
I started with sneaking moms panties and pantyhose at about 5 or 6 and have been wearing every single.
Jessie407 · 70-79, M
@Randie I just wish my wife accepted my dressing. She doesn't have to help me (although that would be the best), but simply not condemn me for my female side.
Gentlemickey · 70-79, M
I really liked this story. I was a little older when I first slipped into a pair of sexy panties, and I was hooked for life !! Wearing layers really enhances the wonderful silky experience. Even when I going to bed I love rubbing my stocking covered legs together, and caressing my little penis through my nylon panties and my silky nightie !! I am straight, gut I enjoy seeing men and women wearing panties and lingerie !! ...🤭
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RemovedUsername821079 · 61-69, M
Jessie I love your story. I was 10 when I started wearing my mother's pantyhose.My first sexual experience was when a male friend masturbated me while I was wearing only nude pantyhose.

 
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