Questions for all of my fellow crossdressers

[Adventurouscdm]

I've been dressing up for 20 years myself. At first it was just something I thought of while I was young and in my party stage. My wife was gone one night and I was horny and wanted to do something different. Been wearing her stuff ever since. Of course I buy my own heels, wig and fake tits and even outfits sometimes too but wearing her stuff is a real turn on for me. Do your wives / significant others know about your secret? Has anyone seen you dressed? In 20 years nobody has seen me dressed until last year. A neighbor from the street I used to live on has some kinks of her own so I knew it would be safe to fill her in on my secret and she has been turned on by it ever since. Does anyone go all out with makeup, jewelry, etc ? Another part of it that I find thrilling is both driving around at night dressed up and being outside at night dressed up. Both have that thrill of being caught out in the open but the safety of the darkness to help keep from being exposed. Curious to hear about how it started for other CD's and what part turns you on the most.

 

[drobert44]

I've been dressing up for 20 years myself. At first it was just something I thought of while I was young and in my party stage. My wife was gone one night and I was horny and wanted to do something different. Been wearing her stuff ever since. Of course I buy my own heels, wig and fake tits and even outfits sometimes too but wearing her stuff is a real turn on for me. Do your wives / significant others know about your secret? Has anyone seen you dressed? In 20 years nobody has seen me dressed until last year. A neighbor from the street I used to live on has some kinks of her own so I knew it would be safe to fill her in on my secret and she has been turned on by it ever since. Does anyone go all out with makeup, jewelry, etc ? Another part of it that I find thrilling is both driving around at night dressed up and being outside at night dressed up. Both have that thrill of being caught out in the open but the safety of the darkness to help keep from being exposed. Curious to hear about how it started for other CD's and what part turns you on the most.

I have a CD pal who helps him dress for men. He gets plenty of cock and so does she, quite the hotwife!

 

[Kellieskirt]

Yes oh so luv to go out nice night drive part of me hopes to get caught by the right type of guy lol

 

[HeatherMaureen8065]

Started dressing at 13. By 18 I was completely dressing femininely - make-up, hair, nails, fully shaven - and would venture out for late night walks. Very thrilling / scary / exciting, especially when I knew I'd been seen, even if only from a distance, Met a gay male when hitching a ride who played with my leg and might have successfully seduced me if a passing police car hadn't cooled things down that night.
I told him I'd need a ride from the same spot two nights later and he picked me up again. I got him to stop at a 24 hour gas station and used the washroom to finish transforming myself; I'd done more than half at my part time job earlier. Until I was walking out to his car in a short skirt, semi sheer blouse and three inch heels I'd never considered that he might not like the idea that I wanted to be dressed like a girl for him.
He introduced me to oral, both giving and receiving, anal and exhibitionism that night! Now for me the real thrill isn't just going out while sluttily dressed, tho that is still scary / exciting enough by itself, but to prance around in a nearby park in just my lingerie to flash others or stop to pose for the few I sorta knew from previous encounters.
I haven't been caught by anyone I haven't wanted to be caught by so far but have been seen by many!

 

[Subsy]

I've been dressing up for 20 years myself. At first it was just something I thought of while I was young and in my party stage. My wife was gone one night and I was horny and wanted to do something different. Been wearing her stuff ever since. Of course I buy my own heels, wig and fake tits and even outfits sometimes too but wearing her stuff is a real turn on for me. Do your wives / significant others know about your secret? Has anyone seen you dressed? In 20 years nobody has seen me dressed until last year. A neighbor from the street I used to live on has some kinks of her own so I knew it would be safe to fill her in on my secret and she has been turned on by it ever since. Does anyone go all out with makeup, jewelry, etc ? Another part of it that I find thrilling is both driving around at night dressed up and being outside at night dressed up. Both have that thrill of being caught out in the open but the safety of the darkness to help keep from being exposed. Curious to hear about how it started for other CD's and what part turns you on the most.

Drive thru’s offer opportunities anonymous……..by oneself or with ……?

 

[AmiInDland]

Started dressing at 13. By 18 I was completely dressing femininely - make-up, hair, nails, fully shaven - and would venture out for late night walks. Very thrilling / scary / exciting, especially when I knew I'd been seen, even if only from a distance, Met a gay male when hitching a ride who played with my leg and might have successfully seduced me if a passing police car hadn't cooled things down that night.
I told him I'd need a ride from the same spot two nights later and he picked me up again. I got him to stop at a 24 hour gas station and used the washroom to finish transforming myself; I'd done more than half at my part time job earlier. Until I was walking out to his car in a short skirt, semi sheer blouse and three inch heels I'd never considered that he might not like the idea that I wanted to be dressed like a girl for him.
He introduced me to oral, both giving and receiving, anal and exhibitionism that night! Now for me the real thrill isn't just going out while sluttily dressed, tho that is still scary / exciting enough by itself, but to prance around in a nearby park in just my lingerie to flash others or stop to pose for the few I sorta knew from previous encounters.
I haven't been caught by anyone I haven't wanted to be caught by so far but have been seen by many!

Sexy pic

 

[CdKimMajick]

I've been dressing up for 20 years myself. At first it was just something I thought of while I was young and in my party stage. My wife was gone one night and I was horny and wanted to do something different. Been wearing her stuff ever since. Of course I buy my own heels, wig and fake tits and even outfits sometimes too but wearing her stuff is a real turn on for me. Do your wives / significant others know about your secret? Has anyone seen you dressed? In 20 years nobody has seen me dressed until last year. A neighbor from the street I used to live on has some kinks of her own so I knew it would be safe to fill her in on my secret and she has been turned on by it ever since. Does anyone go all out with makeup, jewelry, etc ? Another part of it that I find thrilling is both driving around at night dressed up and being outside at night dressed up. Both have that thrill of being caught out in the open but the safety of the darkness to help keep from being exposed. Curious to hear about how it started for other CD's and what part turns you on the most.

I have been married 3 times. They all knew but only 2 liked it. One liked it so much we would go out in matching outfits when we were out of town. All of my SOs as well know/knew.

I used to go out all the time but now that i am curvy and unable to pass I am nervous to do so but I was brave enough to try on a sundress at target yesterday.

I'm at the point that if I want to go out in public in the day time I will once I get that courage up.

I am always in panties though even in public. Every day. Today I went out with a teddy under my shirt.

 

[writerzblok92]

Started dressing at 13. By 18 I was completely dressing femininely - make-up, hair, nails, fully shaven - and would venture out for late night walks. Very thrilling / scary / exciting, especially when I knew I'd been seen, even if only from a distance, Met a gay male when hitching a ride who played with my leg and might have successfully seduced me if a passing police car hadn't cooled things down that night.
I told him I'd need a ride from the same spot two nights later and he picked me up again. I got him to stop at a 24 hour gas station and used the washroom to finish transforming myself; I'd done more than half at my part time job earlier. Until I was walking out to his car in a short skirt, semi sheer blouse and three inch heels I'd never considered that he might not like the idea that I wanted to be dressed like a girl for him.
He introduced me to oral, both giving and receiving, anal and exhibitionism that night! Now for me the real thrill isn't just going out while sluttily dressed, tho that is still scary / exciting enough by itself, but to prance around in a nearby park in just my lingerie to flash others or stop to pose for the few I sorta knew from previous encounters.
I haven't been caught by anyone I haven't wanted to be caught by so far but have been seen by many!

What a great story and you look super sexy in that outfit

 

[Dannicurious3]

Only been cd at home with wife but going out of town this weekend and i am going to dress up and go to a bar. I am a bigger curvy bodied CD, it is hard to do this but i have to try.

 

[Bisexguy70]

Ive responded to another post but I enjoy sharing my story. I tried it on a whim when I was staying out of town. I had a garter belt, panties, thigh highs and camisole top. Ive never masturbated so much as I did that night. Looking at tranny porn and feeling a connection, wanting so bad to suck cock and get fucked. I tried sharing it with my wife but she was turned off. Somehow I found this guy on CL and shared naughty pics of me dressed. Later I bought some crotchless fishnets and we met in private. He licked my ass good and wearing the lingerie made me feel like some dirty cheap slut. Whenever I wear lingerie I get the urge to please a man. I love feeling fem and submissive. Ive had many men tell me it was sexy as fuck wearing just my thigh highs, panties around my ankles and on my knees. The thing I love the most is how it transforms me into this lustful character and being able to relate somehow to being a female. I love how it makes a guy mad with lust and turns him on. Its really hard to explain but I also get super hard going into some retail store and buying some sexy outfits. I have wore some of my wifes stuff. My avatar pic is my wifes top.

 

[cuckoldbill]

Only been cd at home with wife but going out of town this weekend and i am going to dress up and go to a bar. I am a bigger curvy bodied CD, it is hard to do this but i have to try.

How did your trip go. Did you visit that bar fully dressed? X

 

[Dannicurious3]

I did. It was so hard at first but it got easier as the night went on. We went from the Hotel directly to the Bar and back. Overall it was a good experience but wouldn’t say that I felt released or free. Always a small uneasiness remained.

 

[bobsch703]

Started dressing at 13. By 18 I was completely dressing femininely - make-up, hair, nails, fully shaven - and would venture out for late night walks. Very thrilling / scary / exciting, especially when I knew I'd been seen, even if only from a distance, Met a gay male when hitching a ride who played with my leg and might have successfully seduced me if a passing police car hadn't cooled things down that night.
I told him I'd need a ride from the same spot two nights later and he picked me up again. I got him to stop at a 24 hour gas station and used the washroom to finish transforming myself; I'd done more than half at my part time job earlier. Until I was walking out to his car in a short skirt, semi sheer blouse and three inch heels I'd never considered that he might not like the idea that I wanted to be dressed like a girl for him.
He introduced me to oral, both giving and receiving, anal and exhibitionism that night! Now for me the real thrill isn't just going out while sluttily dressed, tho that is still scary / exciting enough by itself, but to prance around in a nearby park in just my lingerie to flash others or stop to pose for the few I sorta knew from previous encounters.
I haven't been caught by anyone I haven't wanted to be caught by so far but have been seen by many!

Smokin' hot!

 

[Smoothshavendad]

Extremely hot!

 

[Dannicurious3]

Yeah I’m not sure what my goals are long term. Been thinking through that some lately. But was a good experience for my first time overall. Probably will do it again at a later time. It took all my focus.

 

[sonjaluv]

Congratulations, Danni! That's a bold step. I'm wishing you the best and would love to hear more as you continue your journey. Luv, Sonja

 

[cuckoldbill]

I did. It was so hard at first but it got easier as the night went on. We went from the Hotel directly to the Bar and back. Overall it was a good experience but wouldn’t say that I felt released or free. Always a small uneasiness remained.

Well done. You have that first “terrifying” but awesome experience done and you survived it . Next one will be so much easier and you will be able to relax and enjoy it. So happy for you .

 

[EmberCD]

I've been dressing up for 20 years myself. At first it was just something I thought of while I was young and in my party stage. My wife was gone one night and I was horny and wanted to do something different. Been wearing her stuff ever since. Of course I buy my own heels, wig and fake tits and even outfits sometimes too but wearing her stuff is a real turn on for me. Do your wives / significant others know about your secret? Has anyone seen you dressed? In 20 years nobody has seen me dressed until last year. A neighbor from the street I used to live on has some kinks of her own so I knew it would be safe to fill her in on my secret and she has been turned on by it ever since. Does anyone go all out with makeup, jewelry, etc ? Another part of it that I find thrilling is both driving around at night dressed up and being outside at night dressed up. Both have that thrill of being caught out in the open but the safety of the darkness to help keep from being exposed. Curious to hear about how it started for other CD's and what part turns you on the most.

I started around 40 years ago, I’m 47 now. It was a curiosity that continued to grow, really long story. Yes, I have shared it with all of my romantic partners, and also a handful of non romantic friends. I’ve seen the full gamut of reactions from enthusiastic encouragement, to beratement & belittling. I don’t try to pass at 6’-2” I’m not blending in, the beard doesn’t help much either. For a long time it was mostly a kink/fetish, but it’s evolving into a comfort thing now as well. I wear panties under my clothes most days and I have lots of lingerie. But a few years ago I realized I’d really like to wear a skirt as opposed to shorts. I have no desire to transition, no desire to pass, I still want a partner that will engage in lingerie play, but I also like challenging the social norms and wearing a skirt. This is the lightest of explanations, and doesn’t even scratch the surface of 40 years of crossdressing experiences, but I’m pretty sure this ain’t the place for that. I’m just thankful that there are platforms like Lit where I can meet people with similar interests and experiences.

 

[SPARTAN047]

Only trans or TV friends have seen me dressed. Or naked.

I try not to be caught by anyone else. Not even my family.

Some of my work colleagues know, but I told them I'll be transitioning very soon and I'll probably go almost full woman (no surgery) everywhere. Dressing, makeup and everything, inducing HRT. I can't afford laser hair removal.

I hope to be on hormones by the end of this year or the beginning of the next.
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