Crossdressing

[Pantyhose971]

I know there are some topics a bit related to crossdressing, but I did not find anyone where experience are shared.

When was the first time you crossdressed, when did you start have a fantasy about it? How many time do you invest in it an many other stuff.

For me it started when I was around 8 years old, I already discovered that pantyhose was something I did fancy, but in shows I saw on tv I like the Girls clothes a lot more then the boys clothes many times. I had sometimes a fantasy about it but never telled and I try to forget.

At the time we had a serie in the Netherlands, called 'Onderweg naar morgen.' There was a lovely girl Who wears a lot of the time a pantyhose. When I was home alone I tried to look like her with my mothers clothes.

When I was older I had a few years a stepsister and I wear some of her clothes often.

Now I have a few outfits, and from time to time I like to do it.

[wannabetiedup]

I never really thought of cross dressing much at all, especially not as part of my bondage interests. However, about 20 years ago, my girlfriend at the time asked me to wear one of her dresses as part of a play session where she also tied me up. I did so, and I can't say it did anything for me at the time. It was a bit of fun, but wasn't quite sure what the purpose was.
From my own perspective, I try to understand for me what I am trying to experience by cross dressing. Like yourself, I grew up envious of the fashion options open to women compared to those for men. I guess I wanted to experience the feeling of the clothes, rather than "try to be/look like a woman" or be treated as a woman.
I know it's super complex, and everyone's motivation is different, but thought I'd give my honest response.

[illest]

I feel like for me mine started when I was in middle school/early high school. I was curious here and there and never really thought about it much. When I started finding bondage-related stories I would see stuff about being tied by other girls and being dressed up as one of them as a humiliation, and for some reason it intrigued me.

My mom unknowningly kind of fueled this as well, because my room was moved to the bottom part of tge house that had more room than the rest of the house. Because of this for a period she was keeping a collection of her old dresses in boxes and on racks in the back of my room! Not only that but in high school they for School Spirit Week a day called "Switch Day" where the guys dressed as girls and vice-versa. Being a nerd that got picked on by girls there on the regular I wasn't comfortable with participating to give them ammo. However that was fuel to try on a few of the dresses that were there at the time, and being someone already getting into the aearly stages of self binding it started something.

I was never able to actively go out and buy CD clothing but I was only really interested when it coincided with bondage. It's never been a freedom thing for me; it's always been the allure/mystique of looking in the mirror and seeing a different person bound. These last few years though it's taken on a new form. My wife pretty much has things like wigs and lipstick available that wasn't available to her before. To top it off she bought french maid lingerie that she used once and never uses again and outfits from Amazon that I bought(mostly ) for her from school girl outfits to thigh highs. Most of the stuff that fits her also fits me because though I'm taller she's pretty wide in the hip area. The only two things she had that I haven't a hope in hell of fitting are her bras and her heels/shoes. I did find recently she has one of those strapless bras that she hasn't used in years but our shoe sizes are vastly different. She made a joke a while back about her wearing her shoes and I told her it definitely wouldn't work. She has no clue it was because I've tried it before.

Even still though I only do it on special occasions. In other words when I have plenty of time to not only prepare but to properly remove all makeup residue and put everything back as it was. So usually it's about 3-4 times out of the year when she goes on a 2-day vacation with a couple of her friends. Sometimes I wind up ordering a couple of things from Amazon to experiment with. She's actually on one of those today so I had ordered some pink cotton rope and three sleep masks. I'll also buy a door mirror when I get off because I've never had a mirror large enough to see a full view of myself. As far as the bondage stuff I'm usually safe in that regard. She knows I'm into bondage and fantasize about tying her up though she's not really into being tied up so she does it occasionally to humor me. She knows I like being tied up as well and she knows I'm into femdom but I don't think she knows about the self bondage thing. I do have to be careful as I did have a close call when I left a errant piece of rope on the floor. Also had a more troublesome one earlier in the year with a crossdress bound session where in a hogtie I got a lipstick mark on the sheet! I'm sure she would have handled the truth better but it'd be far more embarassing on my part

[Pantyhose971]

[mention]illest[/mention] I know for sure how you feel cause I have the same issieu cause I am also still stuck at home. And I love her, to get me Wrong. But her closeth is boring. Really boring. So I bought some stuff myself but I have to hide it haha with my other toys...

[MrBind]

It's something I have an interest in.

[wannabetiedup]

Not wanting to hijack this discussion, but I'm curious about what drives the crossdressing desire. As I said earlier in the thread, is it about the feel of the clothes or is it to feel like a woman? I'm curious about the former, but not really interested in the latter.

But after this thread was started I decided to try out a pair of tights. It was an old pair of my wife's, which has been used as part of our restraints collection, but only used previously to bind rather than wear. I must admit the feeling was lovely and I could definitely be interested in wearing them whilst bound. But full scale cross dressing? If my wife asked me to do it, I'd probably indulge her, but I don't think I'd do it otherwise

[Pantyhose971]

[mention]wannabetiedup[/mention] for me it is just the clothes. I don't do wigs that much cause it inch my head and also no make up cause I have an allergic reaction with my skin on a lot off stuff.

But I really like the womens clothes and then not the jeans cause that almost never fits. But a nice skirt with a top, bloose or turtleneck or a nice dress with some nylons with it it just feel good.

When I look in the mirror crossdressed, to be honest. I feel me. This is me. It is a strange thing, you need to have that feeling inside to understand.

[wannabetiedup]

@wannabetiedup for me it is just the clothes. I don't do wigs that much cause it inch my head and also no make up cause I have an allergic reaction with my skin on a lot off stuff.

But I really like the womens clothes and then not the jeans cause that almost never fits. But a nice skirt with a top, bloose or turtleneck or a nice dress with some nylons with it it just feel good.

When I look in the mirror crossdressed, to be honest. I feel me. This is me. It is a strange thing, you need to have that feeling inside to understand.

Thank you for the candid response. I think you have summed it up really well. And I think I understand where you're coming from too. It's actually quite nice to hear it's about you and doing it for you. I commend that Do you go outside cross dressed or is it just a private thing for you?

[Pantyhose971]

[mention]wannabetiedup[/mention] for me it is private. But when it is Cold outdife I wear it under my own clothes. If I wear my jeans I sometimes wear a stockings with girdle underneath. Or wear a pantyhose underneath it.

But it is not that I go out in that clothes, cause I don't need to have all eyes on me.

[captured_prize]

I started crossdressing when I was a teenager. It started out as mere curiousity but I found that I really liked the feel of women's clothes. When I got older, I got more into wigs and makeup, trying to make myself more passable. For me, crossdressing is a way of expression and fulfilling the need to get out of my own skin sometimes.

[mention]wannabetiedup[/mention] Honestly, the desire to crossdress is pretty complex and you'll get a bunch of different answers for this. There is no one size fits all when it comes to crossdressing.

[wannabetiedup]

I started crossdressing when I was a teenager. It started out as mere curiousity but I found that I really liked the feel of women's clothes. When I got older, I got more into wigs and makeup, trying to make myself more passable. For me, crossdressing is a way of expression and fulfilling the need to get out of my own skin sometimes.

@wannabetiedup Honestly, the desire to crossdress is pretty complex and you'll get a bunch of different answers for this. There is no one size fits all when it comes to crossdressing.

I've no doubt it's complex, and definitely appreciate the expression part. We all need that certainly, however it manifests. I am curious about cross dressing though, and I imagine I would probably get similar feelings if I did dress up. Either way I'm happy for your insight

[MrBind]

Not wanting to hijack this discussion, but I'm curious about what drives the crossdressing desire. As I said earlier in the thread, is it about the feel of the clothes or is it to feel like a woman? I'm curious about the former, but not really interested in the latter.

I'm just curious. I guess it's because I love being tied up as well as to tie the ladies in my life, and I prefer the ladies be dressed as ladies. And I sometimes fantasize about being tied while wearing hose.

[WillHBonney]

I wouldn't really consider myself as a crossdresser as I don't it although I like the idea of it being forced upon me by my captor as a form of humiliation. I'm a reluctant crossdresser I suppose.

However, there is 1 particular style of woman's footwear that I've always liked the look of and used to own my own pair. Funnily enough the same product exists for men albeit slightly different in shape and they're definitely less common on the streets. I mention that because realistically I could buy a men's pair and wear them out and about without raising too many eyebrows. However the idea of owning a men's pair has never appealed to me, nor has wearing them (men's or women's) out in public.
When I used to own a pair of women's ones. I would wear them about the house when I was home alone, then shove them deep into my wardrobe when someone came home.

It's hard to say exactly what I got out of wearing them. I guess I just enjoyed owning something that I had admired on others many times in the past. And occasionally I would see someone wearing them with an interesting style and I'd try to copy that the next time I had them on.

[wannabetiedup]

What are the shoes called?

Also I think I could be a reluctant cross dresser too if the wife insisted I dress up. I might try to sow that seed so it makes her think it was her idea when she eventually does it lol

[illest]

It's complex. Like in my case I don't have a inclination unless it's bondage related. I think with me it's also the mental image of being bound. As a guy and as someone who has no attraction to the male body whatsoever, being bound as a guy doesn't do anything for me. However being able to imagine myself as a DID just for the moment is the complete opposite. If I still looked manly afterwards it'd be one thing but strangly my body type pulls it off eerily well. I'm tall but have hardly any muscles and virtually no hair on my legs and smooth hands. My wife is actually jealous of them. On the other hand my chest is hairy so I wear clothes that cover my chest fully. I can't deal without a gag anyway so I don't have to worry about my face too much anyway but I do shave usually if I'm planning a full blown session with makeup.

It's honestly something I played around with but the last couple of years I've experimented with more not only because I have access to the things to do so now but because I'm in my mid-30s so want to try it a few times while I still look pretty attractive. I live a clean lifestyle so I still look in my mid-20s to most people but I know that won't last forever. Also DeviantArt is definitely a factor. I wind up trying scenarios or variations of scenarios I see in art and a lot of the best ones I've seen lately involve forced feminization.

[illest]

What are the shoes called?

Also I think I could be a reluctant cross dresser too if the wife insisted I dress up. I might try to sow that seed so it makes her think it was her idea when she eventually does it lol

Sounds similar to what I'm trying to do. She makes jokes about our daughter if we ever have one dressing me up for tea parties and very occasionally shows me FaceBook vids of guys dressing flawlessly into women so I might one day pull her card and "dare" her to make me look like that.

[Raian]

Hey I hope its alright I join in, I started at a young age aswell about 9 years old with crossdressing although I never realized thats what I was doing and I was encouraged a lot by my sister, as she wanted a sister of her own and parents had no issue with it so it just continued, as was said already it was nice looking in the mirror and seeing someone different, had a weird comfort to it like in a spy show changing my identity type of thing and what added the bondage element was a friend of mine who added tying me up to basically every game we played which I always had fun with

[MrBind]

Great you had someone to help you.

[MrBind]

Great you had someone to help you.

[Raian]

thanks, I think it helps really if you can have someone know so you can see its accepted especially when your young and trying it

[captured_prize]

While my bondage and crossdressing were initially seperate, I eventually combined the two, finding a lot of fun in playing a damsel in distress. This motivated me to get better outfits, improve my makeup, and just make myself more passable. In return, making myself more passable further motivated me to continue crossdressing even if I didn't do bondage. Also, making myself more passable made my bondage sessions even more satisfying as I saw myself as the damsel in distress I thought I could be.

Has anyone else had this cycle where bondage motivates you to crossdress better, better crossdressing allows for more expression, and better crossdressing and feminine expression leads to better bondage sessions?

[Pantyhose971]

Have to be honest about that, but we discussed it before trough private messages [mention]captured_prize[/mention] that I am not so far with crossdressing as some others I speak over here are.

But in my mind, I think it is going to work together indeed. You can practice your rope work, or what ever you use. And then with imagination you can imagine what ever you are

[sami200456boyfriend]

My sister dressed me like a girl one time and it feel great. The dress and the makeup on my face felt pretty. I done sometimes over my high school days.

[captured_prize]

My sister dressed me like a girl one time and it feel great. The dress and the makeup on my face felt pretty. I done sometimes over my high school days.

Dresses and makeup certainly have a way of making someone feel pretty. I wish I had a sister who could have done my makeup and given me fashion advice. Oh well, I still figured things out

[BiancaBound]

Hello if I may add something to the discussion. Crossdressing and bondage can be connected. I feel that high heels and tight corsets are a sort of bondage as they restrict how you move.

I've always felt that a woman looked better in bondage than a man, there's more grace to it.

As for dressing up I've been with the same woman for the past 17 years and instead of imposing my tastes on her, I dress how I feel a feminine woman should dress. She cannot wear high heels so I wear them.