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Why Do We Crossdress

ElaineCD51 said:
I was fourteen years old when I swiped one of my mother's bras and wore it under my sweater while the family hiked in the nearby mountains. I really enjoyed the pressure of the band on my chest and the thrill of getting away with doing something naughty and the fact that no one suspected a thing. It took many years for me to get to full cross dressing, when I was living alone amassing a bit of a wardrobe. I just feel so sexy when I dress up.
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Good for you !! I envy you !!
 
gunkboy said:
Very similar. Putting laundry away. Panties into her drawer. Thought...I'm alone. Why not ? Bit tight. But, felt amazing. Now when I have the house to myself I put on as much as possible. Totally unpassable. But, I love the feel...and look too. If I am luck enough to be alone overnight. I sleep.in one of her nighties ! I've learned about Woolite and a hair dryer after a "mistake".
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Gotta learn that woolite and hair dryer thing. Had to toss a pair of wife’s panties due to a whoops.
 
Here's how it began for me: My cousin stayed with my family for a month or so one summer. She'd been a runaway and in trouble with the law. She was a tough tomboy and looked a lot like Joan Jett (a true Runaway). She was very pretty but unapproachable. We got along but only because I kept my distance. She stayed in my room while I stayed in my brother's room. The day she left for the airport was bittersweet. I liked having her with us but was happy to be back in my bedroom. I peaked in the laundry basket. Beneath a towel was a pair of white satin panties. She left those behind. I was surprised her panties were so feminine. I'll never forget the black ivy outlines. I closed the door before pulling the treasure from the basket. I smelled her perfume (a fragrance I learned was called Anais Anais). The panties were clean by my standards but had little signs of white wear on the cotton gusset. No one knew the panties were left behind or were in my possession. I folded them and found a jacket pocket in my closet for storage. My mind kept wandering back to those panties throughout the days following her departure. One night I held them close in bed and finally got the courage to try them on beneath my pajamas. The fabric felt SO nice against my skin. Every night for several weeks I wore the panties until one morning I awoke with morning wood and needed to use the bathroom with an unusual urgency. I closed the bathroom door and for the first time ever wet my pants. Except this wasn't pee. What was happening?? I pulled out my member and spurted everywhere before reaching the toilet. I cleaned up the mess and washed the panties in the sink. I later dried them in my closet and was sad my cousin's perfume was no longer detectable. I still wore the panties at night and noticed I got hard from the sensation of satin against my skin. Soon after, masturbation in the panties became a nightly ritual and I found myself wearing beneath my regular clothes during the day. A month or two later at school I got a concussion while playing tag football and got to visit the clinic. The school nurse opened a few cabinets for something and a stack of neatly folded panties were on one shelf. Satin and cotton panties. I guess those were spares for females in need. Not long after that discovery I found myself in the clinic after hours. My ride was late after basketball practice and I wandered the empty school. I opened the cabinet and took two pairs of satin panties and put them in my bag. Pretty soon I wore only panties beneath my regular clothes. Over time I acquired a bra and nylons, stockings and a corset. Big secret. When my parents were gone for weekends I dressed up completely with my mom's clothes and makeup. I was a closet sissy. No one would have guessed. I had friends, girlfriends and gay friends yet this secret was all mine.
 
Ciceri said:
Here's how it began for me: My cousin stayed with my family for a month or so one summer. She'd been a runaway and in trouble with the law. She was a tough tomboy and looked a lot like Joan Jett (a true Runaway). She was very pretty but unapproachable. We got along but only because I kept my distance. She stayed in my room while I stayed in my brother's room. The day she left for the airport was bittersweet. I liked having her with us but was happy to be back in my bedroom. I peaked in the laundry basket. Beneath a towel was a pair of white satin panties. She left those behind. I was surprised her panties were so feminine. I'll never forget the black ivy outlines. I closed the door before pulling the treasure from the basket. I smelled her perfume (a fragrance I learned was called Anais Anais). The panties were clean by my standards but had little signs of white wear on the cotton gusset. No one knew the panties were left behind or were in my possession. I folded them and found a jacket pocket in my closet for storage. My mind kept wandering back to those panties throughout the days following her departure. One night I held them close in bed and finally got the courage to try them on beneath my pajamas. The fabric felt SO nice against my skin. Every night for several weeks I wore the panties until one morning I awoke with morning wood and needed to use the bathroom with an unusual urgency. I closed the bathroom door and for the first time ever wet my pants. Except this wasn't pee. What was happening?? I pulled out my member and spurted everywhere before reaching the toilet. I cleaned up the mess and washed the panties in the sink. I later dried them in my closet and was sad my cousin's perfume was no longer detectable. I still wore the panties at night and noticed I got hard from the sensation of satin against my skin. Soon after, masturbation in the panties became a nightly ritual and I found myself wearing beneath my regular clothes during the day. A month or two later at school I got a concussion while playing tag football and got to visit the clinic. The school nurse opened a few cabinets for something and a stack of neatly folded panties were on one shelf. Satin and cotton panties. I guess those were spares for females in need. Not long after that discovery I found myself in the clinic after hours. My ride was late after basketball practice and I wandered the empty school. I opened the cabinet and took two pairs of satin panties and put them in my bag. Pretty soon I wore only panties beneath my regular clothes. Over time I acquired a bra and nylons, stockings and a corset. Big secret. When my parents were gone for weekends I dressed up completely with my mom's clothes and makeup. I was a closet sissy. No one would have guessed. I had friends, girlfriends and gay friends yet this secret was all mine.
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What a story so do you approached your cousin
 
Ciceri said:
Here's how it began for me: My cousin stayed with my family for a month or so one summer. She'd been a runaway and in trouble with the law. She was a tough tomboy and looked a lot like Joan Jett (a true Runaway). She was very pretty but unapproachable. We got along but only because I kept my distance. She stayed in my room while I stayed in my brother's room. The day she left for the airport was bittersweet. I liked having her with us but was happy to be back in my bedroom. I peaked in the laundry basket. Beneath a towel was a pair of white satin panties. She left those behind. I was surprised her panties were so feminine. I'll never forget the black ivy outlines. I closed the door before pulling the treasure from the basket. I smelled her perfume (a fragrance I learned was called Anais Anais). The panties were clean by my standards but had little signs of white wear on the cotton gusset. No one knew the panties were left behind or were in my possession. I folded them and found a jacket pocket in my closet for storage. My mind kept wandering back to those panties throughout the days following her departure. One night I held them close in bed and finally got the courage to try them on beneath my pajamas. The fabric felt SO nice against my skin. Every night for several weeks I wore the panties until one morning I awoke with morning wood and needed to use the bathroom with an unusual urgency. I closed the bathroom door and for the first time ever wet my pants. Except this wasn't pee. What was happening?? I pulled out my member and spurted everywhere before reaching the toilet. I cleaned up the mess and washed the panties in the sink. I later dried them in my closet and was sad my cousin's perfume was no longer detectable. I still wore the panties at night and noticed I got hard from the sensation of satin against my skin. Soon after, masturbation in the panties became a nightly ritual and I found myself wearing beneath my regular clothes during the day. A month or two later at school I got a concussion while playing tag football and got to visit the clinic. The school nurse opened a few cabinets for something and a stack of neatly folded panties were on one shelf. Satin and cotton panties. I guess those were spares for females in need. Not long after that discovery I found myself in the clinic after hours. My ride was late after basketball practice and I wandered the empty school. I opened the cabinet and took two pairs of satin panties and put them in my bag. Pretty soon I wore only panties beneath my regular clothes. Over time I acquired a bra and nylons, stockings and a corset. Big secret. When my parents were gone for weekends I dressed up completely with my mom's clothes and makeup. I was a closet sissy. No one would have guessed. I had friends, girlfriends and gay friends yet this secret was all mine.
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Did you ever get caught wearing???
 
No, but my girlfriend in college helped me crossdress for Halloween once. She commented on the satin panties. "Why are you wearing panties? No one would know you're wearing your own underwear beneath the dress." That was a valid question. I admitted I liked the way it felt. After the party we had sex and she said it was weird to get it on with me as a woman - so it didnt happen again :(
 
when I was younger and still living at home I tried on a pair of my mom's panty hose. I was rock hard and enjoyed the feeling of the nylon against my skin. Years later after I started playing with guys I figured out that I am submissive in a feminine way,

Outwardly I'm masculine, business owner, the "go to" guy for decisions. So much pressure to be the man! When I wear women's clothes all that goes out the window. I love being "taken care of" in many ways and I don't have the responsibilities that I have otherwise. I submit to my male partner and let them get their pleasure from me as a female.

Also part of that is looking sexy and feeling good and I suppose a little bit of taboo turns me on.
 
remington123691 said:
when I was younger and still living at home I tried on a pair of my mom's panty hose. I was rock hard and enjoyed the feeling of the nylon against my skin. Years later after I started playing with guys I figured out that I am submissive in a feminine way,

Outwardly I'm masculine, business owner, the "go to" guy for decisions. So much pressure to be the man! When I wear women's clothes all that goes out the window. I love being "taken care of" in many ways and I don't have the responsibilities that I have otherwise. I submit to my male partner and let them get their pleasure from me as a female.

Also part of that is looking sexy and feeling good and I suppose a little bit of taboo turns me on.
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I have been wearing since I can remember. I was 31 before I decided to date a man and see if my feminine side worked in a relationship. He didn't approve of my crossdressing and preferred a masculine partner. I never felt like that guy. I tolerated the sex and longed to be in lingerie. Hasn't happened since then
 
remington123691 said:
when I was younger and still living at home I tried on a pair of my mom's panty hose. I was rock hard and enjoyed the feeling of the nylon against my skin. Years later after I started playing with guys I figured out that I am submissive in a feminine way,

Outwardly I'm masculine, business owner, the "go to" guy for decisions. So much pressure to be the man! When I wear women's clothes all that goes out the window. I love being "taken care of" in many ways and I don't have the responsibilities that I have otherwise. I submit to my male partner and let them get their pleasure from me as a female.

Also part of that is looking sexy and feeling good and I suppose a little bit of taboo turns me on.
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It’s not strictly a man thing. I’ve a high pressure career as a woman and desire to stop making decisions and enjoy letting events happen around me and reacting passively.
 
remington123691 said:
when I was younger and still living at home I tried on a pair of my mom's panty hose. I was rock hard and enjoyed the feeling of the nylon against my skin. Years later after I started playing with guys I figured out that I am submissive in a feminine way,

Outwardly I'm masculine, business owner, the "go to" guy for decisions. So much pressure to be the man! When I wear women's clothes all that goes out the window. I love being "taken care of" in many ways and I don't have the responsibilities that I have otherwise. I submit to my male partner and let them get their pleasure from me as a female.

Also part of that is looking sexy and feeling good and I suppose a little bit of taboo turns me on.
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love this
 
I find it very exciting to talk about this.
I never considered myself a cross dresser.
But I guess I am and have been. It all happened quite naturally.
I do wear panties everyday and can't wait to get home from work and get comfy in something more feminine. I have a very nice collection of lingerie and other clothes that are far more feminine than masculine. I love all the feminine fabrics and colors. And of course, a matching bra and panty set is my favorite. Dresses and silk blouses, stockings and anything lace are also so sensual. Feel free to ask me what I am wear.
 
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