Crossdressing on Chatroulette/Omegle

Have you ever crossdressed on sites like Chatroulette and Omegle? For the record, these are sites where you cam to cam with random strangers (all kinds, not strictly crossdressers), and you can start conversations. Personally, I love doing it! Yes, you do have to go through a lot of junk (men's junk if you know what I mean), but when you find the right person it was all worth it. There are two types of pleasant cam partners for me:

- women who are intrigued and interested in your crossdressing. I always ask if I can show off my outfit and they definitely like to give you compliments. Sometimes I even ask them to pick out on of their dresses for me.

- groups of multiple people who will start laughing at you. I tell them to give me tasks. These normally include dancing, posing, twerking, and saying phrases that they typed out loud ("I'm a pretty princess" etc.). I know some of you will find this ridiculous and/or degrading but I personally love the submission and the slight but pleasant humiliation. To see them having fun enjoys me as well.

Any thoughts on this? Have you ever tried something similar?

Not me. No interest.

Not yet, but it sounds intriguing... And I will definitely check out these sites, exploration is good for the sole. Thanks for sharing.

Is it like one on one type or group. You mentioned a group tells you what to do? Also can just any one come and chat or do you have to join a site. Like the old yahoo IM you had to have a password and then you'd get tons of guys looking for the GG showing her boobies and other things. Just wondering. How secure is it because in that old IM you could back trace them to their IP address and find out who they are, usually where they live and who they are friends with. I can't remember the name of it

Not those sites but I use to C2C on similar sites. I learned something from it and enjoyed the attention.

You like to humiliate yourself on camera for people but haven't posted a profile picture on a supportive site like this?

Things that make you go Hmmm....

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Originally Posted by Jaylyn

Is it like one on one type or group. You mentioned a group tells you what to do? Also can just any one come and chat or do you have to join a site. Like the old yahoo IM you had to have a password and then you'd get tons of guys looking for the GG showing her boobies and other things. Just wondering. How secure is it because in that old IM you could back trace them to their IP address and find out who they are, usually where they live and who they are friends with. I can't remember the name of it

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One on one, but sometimes of course there's a group of people sitting behind the camera. You dont have to join, just start camming. Check it out and you'll understand

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Originally Posted by Robertacd

You like to humiliate yourself on camera for people but haven't posted a profile picture on a supportive site like this?

Things that make you go Hmmm....

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They're just strangers all around the world who you'll never see again, and pics last longer, I don't like that. It's just what I prefer.

Not for me this forum works well for me

I have never done anything like that online. I would assume that all of that video could potentially be posted online by whoever you are chatting with?

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Originally Posted by Karen's Secret

I have never done anything like that online. I would assume that all of that video could potentially be posted online by whoever you are chatting with?

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It absolutely could! Something you should be prepared for should you decide to do this sort of thing.

Not for me, not ever, ok if you are young and want kinky stuff up to you in my opinion what you are doing and this forum do not go together, this forum is all I need I do not need to bare my body for others sexual gratification. After all you do not know what they are actually doing whilst you are displaying your self.
All sounds a bit sordid if truth be known.

It took me a very long time to get over self loathing and hatred for wearing women's clothing. It was years and years of lack of knowledge. I still don't know what led me down this road, but, I would not ever put myself in a position to be ridiculed. I think to seek out humiliation projects an uneasiness with cross dressing. It projects an image to me of a young boy forced to wear his sister's dresses as punishment. I would just want to be accepted as a man who enjoys appearing as a woman on occasion.

That being said, each to his or her own. Just keep in mind what Karen posted.

Jessica have fun with what you do but be very careful as some people out there are really nuts

Leann

Back years ago and I can't remember the site name but it was a cam 2 cam and old style chat room online I think it was on aol.
It was great fun at first then I ended up dealing with a stalker couple and that was why I left and had to get the state police involved.
I never understood humiliation or BDSM and if thats your thing then fine its just not interesting to me.

A big NO well for me anyway, if it works for you go at it I say it's very brave of you.

Thanks, no, I'll pass ...

Sounds like fun for you but not for me.

Sounds like fun. Except I'd worry about getting hit on a lot by guys like I do on FB, Jessica.:sad:

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Originally Posted by jessica_brink

They're just strangers all around the world who you'll never see again, and pics last longer, I don't like that. It's just what I prefer.

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LOL you really think nobody can save your cam session and upload it for all to see?

We are not supposed to link to porn here so you go to xvideos.com and search for Chatroulette or Omegle and you will see

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Originally Posted by Bobbi46

Not for me, not ever, ok if you are young and want kinky stuff up to you in my opinion what you are doing and this forum do not go together, this forum is all I need I do not need to bare my body for others sexual gratification. After all you do not know what they are actually doing whilst you are displaying your self.
All sounds a bit sordid if truth be known.

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Just for the record, I don't get naked, at most I lift my dress up when asked, and it's not to turn anyone on. The people I choose to cam with are groups of friends mostly, who have a good laugh at me and didn't come there to get turned on. People who are there with that reason, I simply skip, not interesting to me. And yes I do know what they're doing, as I can see them too. I really don't mind having to twerk or saying things and hearing them laugh at me, I like that.

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Originally Posted by docrobbysherry

Sounds like fun. Except I'd worry about getting hit on a lot by guys like I do on FB, Jessica.:sad:

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I instantly skip those. 99% of men alone on there are there for one thing... . I go for the nice women and especially the groups of people.

Have fun and I hope nothing bad happens.

I hate camming, it makes my big nose look gigantic. I also don't like to provide free adult entertainment to strangers, but that's every individual's choice.

I got on Chatroulette on occasion, especially when I’m out on business and I’m super bored. That’s where I like to practice my voice. I would say the men on there generally know that there are cd’ers on there as they’ll ask you to do things to prove that it is your real hair. About half of the time, I run into naked men and just skip them. None of the conversations I’ve been in are particularly interesting and no conversation has lasted more than 10 minutes. If I had to guess at the numbers, I would say that 25% I’ve run into are women (most are there to meet men, so they skip me), another 25% are couples or groups that are just looking for conversation, and 25% are naked men, and the remaining 25% are men looking to meet women.

Absolutely, positively, definitely not my thing, but if you enjoy it, feel safe, and nobody gets hurt, feel free to please yourself.

- Diane

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Originally Posted by Tracii G

Have fun and I hope nothing bad happens.

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I've sure had fun so far and no bad experiences either

Is there any financial benefit in this?

I spend a lot on makeup!

Stacy!

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Originally Posted by Stacy Darling

Is there any financial benefit in this?

I spend a lot on makeup!

Stacy!

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Absolutely not, it's not a peep show. It's for chatting to strangers

You know, I’m not really crazy about you reinforcing to the public the idea that we are objects of humiliation and derision. Wether you like it or not, you represent all of us.

Jessica,
No point really when you can go out the door and meet people for real and just openly talk to them . I wouldn't go lifting my skirt for anyone not unless a breeze caught me by accident, which it did on one occasion .

Sounds kind of fun but not sure I am ready for that kind of thing yet maybe one day

It does sound like fun to me !

Do you tend to wear fun outfits and costumes or are you just wearing a normal dress !

I would love to wear a vintage dress, and then take it off to reveal a very feminine and lacy full slip ?

So just out of curiosity I tried out Omegle, not en femme, just me with no shirt on. In about 30 minutes I watched an unending parade of generic dudes come sliding past my screen. I was using my DSLR and a virtual cam software so I had this big dumb logo on my screen which I think scarred people off. There was perhaps 3 women and one wanted to chat for a second, but she started doing a strip tease and it was so unexpected I laughed which I think ticked her off and she turned off the connect. I also encountered a group of children who called me old and and pedo, which I told them was rather inappropriate behavior and that they were too young to be using the service and should disconnect.

Ultimately I would call it a bit interesting, but I expected to see more weirdness and not just so many regular dudes. I might try dressing up and seeing what kind of reactions I get.

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Originally Posted by Robbiegirl

It does sound like fun to me !

Do you tend to wear fun outfits and costumes or are you just wearing a normal dress !

I would love to wear a vintage dress, and then take it off to reveal a very feminine and lacy full slip ?

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I usually just wear normal outfits, dresses etc. but fun outfits will definitely get you even more attention. Just remember to only pull up your dress when you're told to.

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Originally Posted by sarah_hillcrest

So just out of curiosity I tried out Omegle, not en femme, just me with no shirt on. In about 30 minutes I watched an unending parade of generic dudes come sliding past my screen. I was using my DSLR and a virtual cam software so I had this big dumb logo on my screen which I think scarred people off. There was perhaps 3 women and one wanted to chat for a second, but she started doing a strip tease and it was so unexpected I laughed which I think ticked her off and she turned off the connect. I also encountered a group of children who called me old and and pedo, which I told them was rather inappropriate behavior and that they were too young to be using the service and should disconnect.

Ultimately I would call it a bit interesting, but I expected to see more weirdness and not just so many regular dudes. I might try dressing up and seeing what kind of reactions I get.

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Definitely try doing it dressed up next time, you'll get more reaction and attention

I can't post any links here (due to occasional bad language), but go to YouTube and search for "YoutubableHD dressed up as a girl"


He's done several videos over the years of him all dolled-up while on Chatroulette & Omegle. Actually pretty funny stuff.

Plus he does a pretty decent chick-voice, and also has a knack for interacting with strangers, which makes it all the better. :D


He actually got his start while using just a mic while playing those real-time, male-dominated video games with other players over the internet. He'd talk like a GG, and have all these people believing that he was.

Finally, he took it one step further, and added the video aspect of it to those video chat-rooms.


Check it out! :thumbsup:

What a prankster Laurababe. I need to work on my fem voice!

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Originally Posted by laurababe

I can't post any links here (due to occasional bad language), but go to YouTube and search for "YoutubableHD dressed up as a girl He's done several videos over the years of him all dolled-up while on Chatroulette & Omegle. Actually pretty funny stuff. Plus he does a pretty decent chick-voice, and also has a knack for interacting with strangers, which makes it all the better."

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Yeah he's great and really pulls it off as a girl, his voice as well, he doesn't go as far as I like to go though

I have a lot of fun camming and I'm on Omegle quite a bit. Omegle lets you input key words to connect you with people that have similar interests. While I use terms like "crossdressing, transgender . . ." 95% of the people are admirers and very few are crossdressers. Still, admirers can be fun sometimes too. Of course my idea of fun would probably offend a few people on here. :devil:

I used to do Chatroulette but don't anymore. You never know who you are going to get.

There's no way to stop what thousands of others do. The net is filled with CDs that are exhibitionists. Jessica and others are gonna continue to do whatever they want on chat sites. If you think she misrepresents us all, that's something you'll just have to live with.

Yeah I’ve used omegle a few times, it’s fun to talk to other cds and admirers. I haven’t tried chatroulette in years though, I didnt find it much fun as it’s too random and didn’t like the people i was getting matched with

Well I tried this, using Omegle with no topics, just random stranger. in about 10 minutes had a lot of junk shoved in my face, and a lot of horny guys wanting to talk. I couldn't keep a straight face, but also just couldn't keep up the Charade. I may try again with the topic filter and try to find another TG, CD, or someone who wants to talk and not....

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Originally Posted by sarah_hillcrest

Well I tried this, using Omegle with no topics, just random stranger. in about 10 minutes had a lot of junk shoved in my face, and a lot of horny guys wanting to talk. I couldn't keep a straight face, but also just couldn't keep up the Charade. I may try again with the topic filter and try to find another TG, CD, or someone who wants to talk and not....

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If you really want a lot of junk shoved in your face, try the "unmoderated" section. It's about 100% junk. LOL Even if you do put in topics like "crossdressing", "transgender" . . . unless you get real lucky, be prepared for about 90-95% to be guys looking to have "fun."

I do dress up and chat on there and on crossdressingchatcity.com, there's also fruzo.com. I've had lots of great chats there. Men always wank to me (not gonna lie...I just pretend I'm a female and dance, show my legs etc, nothing crazy. Most women read me right away and skip or go "Trans" then skip or go "wtf" and skip me. Lesbians sometimes chat, I've gotten makeup tips on there too. I don't talk, I type and recall an awesome girl in Israel, another from Finland. I must've had good passing days. To,each their own.

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Originally Posted by jessica_brink

Have you ever crossdressed on sites like Chatroulette and Omegle? For the record, these are sites where you cam to cam with random strangers (all kinds, not strictly crossdressers), and you can start conversations. Personally, I love doing it! Yes, you do have to go through a lot of junk (men's junk if you know what I mean), but when you find the right person it was all worth it. There are two types of pleasant cam partners for me:

- women who are intrigued and interested in your crossdressing. I always ask if I can show off my outfit and they definitely like to give you compliments. Sometimes I even ask them to pick out on of their dresses for me.

- groups of multiple people who will start laughing at you. I tell them to give me tasks. These normally include dancing, posing, twerking, and saying phrases that they typed out loud ("I'm a pretty princess" etc.). I know some of you will find this ridiculous and/or degrading but I personally love the submission and the slight but pleasant humiliation. To see them having fun enjoys me as well.

Any thoughts on this? Have you ever tried something similar?

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Putting in interests helps.

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Originally Posted by sarah_hillcrest

Well I tried this, using Omegle with no topics, just random stranger. in about 10 minutes had a lot of junk shoved in my face, and a lot of horny guys wanting to talk. I couldn't keep a straight face, but also just couldn't keep up the Charade. I may try again with the topic filter and try to find another TG, CD, or someone who wants to talk and not....

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I looked at the OP's earlier posts and things don't add up for me. You never got back to us on how the 2 weeks a a housewife went and then there was the secret dressing to a help a friend in her clothes but no picks because it is a secret, now you are web-camming your image in women's clothes all over the net and lifting your dress up too, nice.
Sadly I think this thread may be your only true one.