Poll of the Day > I'm cross-dressing in secret! AMA!

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Wowk01
05/23/19 7:21:05 PM
#1:


I'm as straight as an arrow. But the rise I get from a bra and panties from Victoria's Secret is damn intoxicating! I snuck into the store for the first time ever, and told the cashier I'm picking up some things for my "girlfriend." Spoilers: I don't have one! (Which I'm sure no one is surprised to hear.) I also took another hour to go to Walmart. Those asshole's return policy is the easiest to take advantage of, and they had some maternity items. See, I'm also waaaay into pregnant women, so I had to indulge that as well. Don't forget balloons from Party City! (I'll talk more about that experience if people ask. But the short version is that I filled the regular balloons with water, for breasts. Then the punch balloon was a huge-ass pregnant belly. It was so heavy!)

I took it all home, and stuffed it into a garbage bag, then threw it into my bedroom closet. I live in a duplex kind of near the southern US. I have to keep all this hidden from my dad and brother. They're in the apartment next to mine, and pop in all the time. Completely unannounced, might I add! They'd never accept me. Nobody here would. I'd be judged as hell!

I spent an hour in the shower, and shaved every part of my body that I could reach. (Extra tough because I'm a hairy bastard.) Razor burn hurts like a bitch, but when I finished my skin was soooooo smooth! If you've never shaved completely before...I highly suggest you try it! The tactile sensation is just the greatest! Much respect to women, for doing this on a regular basis! I can't imagine.

Once the shower was done, I grabbed white panties, a B-cup push up bra, and some flowery dress from walmart. Feeling the fabric across my fingers felt very special to me. I wish I knew how to tuck better. Kind of hurts, and I'm afraid the equipment will get stuck in some painful way.

Put together with the new snapchat female filter, and I actually looked like a woman! Kind of like my cousin, but different. I could easily catfish...but I won't bother.

One scary time I was grabbing some leftovers from my dad's fridge, and I didn't take off my bra. He was standing in his living room and staring at me. Apparently he wasn't gone, like I thought he was! I flipped out like crazy in my head! (Luckily, no one can ever see the panties hiding in my men's shorts.)

But he was on her bluetooth, and didn't notice the bulges in my shirt. I covered my chest with the leftovers and bolted out of there! I really panicked, my dudes.

Nobody in my life knows what I'm doing. And I'll never tell. But being anonymous is different. So AMA!
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Lokarin
05/23/19 7:26:36 PM
#2:


When I was transcurious - going out a few times as a girl is what helped me decide that I'm definitely happy as a man.

Of course, in my old age I'd never be able to pull it off, now.
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Wowk01
05/23/19 7:32:12 PM
#3:


Lokarin posted...
When I was transcurious - going out a few times as a girl is what helped me decide that I'm definitely happy as a man.

Of course, in my old age I'd never be able to pull it off, now.

Hell, dude. I could NEVER go out in public! Too many people know me! Unless you were open to everyone about being transcurious, I don't know how you'd pull that off...
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darcandkharg31
05/23/19 7:32:35 PM
#4:


This reads like a copy/pasta or some green text put into paragraph form.
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#5
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Nade Duck
05/23/19 7:43:28 PM
#6:


well, alright.
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RedPixel
05/23/19 7:44:14 PM
#7:


darcandkharg31 posted...
This reads like a copy/pasta or some green text put into paragraph form.

Zangulus posted...
Ok

Wowk01 posted...
If you've never shaved completely before...I highly suggest you try it!

Nah, I just feel up my wife.
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Lokarin
05/23/19 7:46:02 PM
#8:


RedPixel posted...

Wowk01 posted...

If you've never shaved completely before...I highly suggest you try it!

Nah, I just feel up my wife.


Fun fact, two spots of hair on my legs NEVER grew back... I found out later that these two spots are actually a form of male pattern baldness.
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Wowk01
05/23/19 7:46:17 PM
#9:


RedPixel posted...
Nah, I just feel up my wife.

Wish I had a wife of my own to do that with. I imagine it must be wonderful. Now that I know what my own skin feels like, fully shaved. I was thinking really hard about that, once I was finished.
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Wowk01
05/23/19 7:47:11 PM
#10:


Lokarin posted...
Fun fact, two spots of hair on my legs NEVER grew back... I found out later that these two spots are actually a form of male pattern baldness.

Woah! Hope I don't have that problem. But I don't think I will. I'm hairier than Wolverine, lol
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FrozenBananas
05/23/19 7:52:32 PM
#11:


User Since: Feb 2017
Karma: 18

Did you just remember the password to your old alt?
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dancer62
05/23/19 8:01:59 PM
#12:


Yeesh! Man up and go to a drag bar.
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captpackrat
05/23/19 8:03:05 PM
#13:


If you tell the people at the store that the stuff is for you, they'll be glad to help you. They've seen it all, and they probably already figured out who it's for. Gee, he's the same size as his girlfriend? What. A. Coincidence.
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wwinterj25
05/23/19 9:28:16 PM
#14:


Pics or no care.
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SkynyrdRocker
05/23/19 9:31:46 PM
#15:


darcandkharg31 posted...
This reads like a copy/pasta or some green text put into paragraph form.

It really does.
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SkynyrdRocker
05/23/19 9:32:27 PM
#16:


Also if you're really hairy won't your brother and dad notice you being completely shaved?
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Wowk01
05/23/19 9:58:15 PM
#17:


dancer62 posted...
Yeesh! Man up and go to a drag bar.

Not sure if there are any nearby. Also, the sight of other men in drag is a huge turn-off to me.

captpackrat posted...
If you tell the people at the store that the stuff is for you, they'll be glad to help you. They've seen it all, and they probably already figured out who it's for. Gee, he's the same size as his girlfriend? What. A. Coincidence.

It's pretty conservative around here. I don't think they'd be that open about it. The cashier at Victor'a Secret made some off-hand comment about the items I bought being for my girlfriend. She assumed this naturally, without me having to lie first. I don't think they'd expect a guy to be buying bras, panties and yoga pants for himself in s town like this.

wwinterj25 posted...
Pics or no care.

I couldn't possibly risk that! Look at what happened to ProJared! I'm not crazy, I want to keep my life intact!

SkynyrdRocker posted...
Also if you're really hairy won't your brother and dad notice you being completely shaved?

It's a bit of a gamble, I admit. But it was long-sleeve and pants weather just a few days ago. By now some of the hair on my arms and legs is growing back. As long as I don't give them a chance to stare at me, I think I'll be fine.
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green dragon
05/23/19 10:22:46 PM
#18:


so are you attracted to pregnant women, or it just turns you on to dress up like one?
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synth_real
05/23/19 10:56:43 PM
#19:


Now that you've told all of us, it's not exactly a secret any more, now is it?

Also, when you stuff your bra with water balloons, do they have a nice jiggle to them?
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Wowk01
05/24/19 12:50:33 AM
#20:


green dragon posted...
so are you attracted to pregnant women, or it just turns you on to dress up like one?

A hardy yes to the first. A quiet yes to the second. (Dressing up pregnant might be more hassle than it's worth, idk.)

Pregnant women are the most beautiful women. Their hair has a nice sheen. Their skin glows. Their breasts swell to their biggest sizes. But the bellies are the best part!

synth_real posted...
Now that you've told all of us, it's not exactly a secret any more, now is it?

Also, when you stuff your bra with water balloons, do they have a nice jiggle to them?

It's a secret for anyone that personally matters to me.

If it's a small bra, with small balloons, its a small jiggle. But when I break out the triple DDDs, and fill the balloons to near-bursting, it's very nice jiggle.

Now, the belly, made from a full punch-balloon? Forget about it! The jiggle is insane! Almost broke the band on my maternity pants! Makes a nice smacking sound, too.
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JCvgluvr
05/24/19 1:20:06 AM
#21:


This guy is definitely repressed.
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TheWitchMorgana
05/24/19 1:23:20 AM
#22:


JCvgluvr posted...
This guy is definitely repressed.

i dont think this means he's secretly trans if that's what you mean. some people just enjoy the performance of feminine dress but don't feel the need to identify differently. same idea with drag really
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Smarkil
05/24/19 2:36:05 AM
#23:


oof not a good look
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Revelation34
05/24/19 5:05:16 AM
#24:


https://www.youtube.com/watch?v=prw2B_03IzY" data-time="

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SkynyrdRocker
05/24/19 7:37:51 AM
#25:


TheWitchMorgana posted...
JCvgluvr posted...
This guy is definitely repressed.

i dont think this means he's secretly trans if that's what you mean. some people just enjoy the performance of feminine dress but don't feel the need to identify differently. same idea with drag really

Yeah, crossdressing as a fetish is definitely a thing. Although I thought it didn't have to do with gender disphoria and the Wikipedia page said otherwise

https://en.m.wikipedia.org/wiki/Transvestic_fetishism
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captpackrat
05/24/19 10:48:33 AM
#26:


SkynyrdRocker posted...
Also if you're really hairy won't your brother and dad notice you being completely shaved?

My SO was a nudist and used to swim with dolphins and he always shaved his entire body... except his arms. He learned as a teenager not to shave his arms because that made it totally obvious. People won't notice if you shave your legs, chest, back and groin if you're wearing normal clothes, but unless it's the middle of winter, everyone will see your arms. And if you're nude, well lots of nudists shave so it won't be unusual.
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LeetCheet
05/24/19 11:40:50 AM
#27:


Aren't panties kinda tight for guys to wear though?
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captpackrat
05/24/19 11:50:24 AM
#28:


LeetCheet posted...
Aren't panties kinda tight for guys to wear though?

Women tend to have wider hips than men. And you can get panties in all sizes from kids up to BBW. Which is why I suggested telling the salesperson that it's for yourself, that way they can help you with sizing.
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-Komaiko54-
05/24/19 12:25:26 PM
#29:


captpackrat posted...
LeetCheet posted...
Aren't panties kinda tight for guys to wear though?

Women tend to have wider hips than men. And you can get panties in all sizes from kids up to BBW. Which is why I suggested telling the salesperson that it's for yourself, that way they can help you with sizing.


Sounds like that can be pretty embarrassing
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captpackrat
05/24/19 12:36:29 PM
#30:


-Komaiko54- posted...
captpackrat posted...
LeetCheet posted...
Aren't panties kinda tight for guys to wear though?

Women tend to have wider hips than men. And you can get panties in all sizes from kids up to BBW. Which is why I suggested telling the salesperson that it's for yourself, that way they can help you with sizing.


Sounds like that can be pretty embarrassing

I did it once, and the saleswoman said that men come in all the time to buy stuff for themselves. Then she helped me pick out a few items and she got the size just right too.
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-Komaiko54-
05/24/19 12:37:28 PM
#31:


captpackrat posted...
-Komaiko54- posted...
captpackrat posted...
LeetCheet posted...
Aren't panties kinda tight for guys to wear though?

Women tend to have wider hips than men. And you can get panties in all sizes from kids up to BBW. Which is why I suggested telling the salesperson that it's for yourself, that way they can help you with sizing.


Sounds like that can be pretty embarrassing

I did it once, and the saleswoman said that men come in all the time to buy stuff for themselves. Then she helped me pick out a few items and she got the size just right too.


Do you live in Thailand or something?
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captpackrat
05/24/19 12:39:21 PM
#32:


-Komaiko54- posted...
captpackrat posted...
-Komaiko54- posted...
captpackrat posted...
LeetCheet posted...
Aren't panties kinda tight for guys to wear though?

Women tend to have wider hips than men. And you can get panties in all sizes from kids up to BBW. Which is why I suggested telling the salesperson that it's for yourself, that way they can help you with sizing.


Sounds like that can be pretty embarrassing

I did it once, and the saleswoman said that men come in all the time to buy stuff for themselves. Then she helped me pick out a few items and she got the size just right too.


Do you live in Thailand or something?

It was a store in Oceanside, CA.
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-Komaiko54-
05/24/19 12:40:04 PM
#33:


captpackrat posted...
CA.


makes sense
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LeetCheet
05/24/19 2:43:23 PM
#34:


How comfortable are they to wear though? Asking for a friend.
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FrndNhbrHdCEman
05/24/19 4:42:22 PM
#35:


Wowk01 posted...
Lokarin posted...
When I was transcurious - going out a few times as a girl is what helped me decide that I'm definitely happy as a man.

Of course, in my old age I'd never be able to pull it off, now.

Hell, dude. I could NEVER go out in public! Too many people know me! Unless you were open to everyone about being transcurious, I don't know how you'd pull that off...

That's what Halloween's for. Excuse to wear heels.
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Disengaged
05/24/19 5:05:00 PM
#36:


Cross dressing? I'm not even allowed to do cross laundry anymore.
Or cross folding.

How are you even supposed to fold girl clothes? They dont make sense! They do not adhere to the laws of physics!

I go and make a nice neat fold of bras or little tube tops, or thongs, and turns out upon unfolding I just tie them in knots or some shit. Its madness.
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synth_real
05/24/19 5:10:21 PM
#37:


FrndNhbrHdCEman posted...
Wowk01 posted...
Lokarin posted...
When I was transcurious - going out a few times as a girl is what helped me decide that I'm definitely happy as a man.

Of course, in my old age I'd never be able to pull it off, now.

Hell, dude. I could NEVER go out in public! Too many people know me! Unless you were open to everyone about being transcurious, I don't know how you'd pull that off...

That's what Halloween's for. Excuse to wear heels.

I once went out on Halloween all dolled up, I walked into the washroom and there were three other dudes in there wearing dresses.
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TheWitchMorgana
05/24/19 6:16:13 PM
#38:


SkynyrdRocker posted...
TheWitchMorgana posted...
JCvgluvr posted...
This guy is definitely repressed.

i dont think this means he's secretly trans if that's what you mean. some people just enjoy the performance of feminine dress but don't feel the need to identify differently. same idea with drag really

Yeah, crossdressing as a fetish is definitely a thing. Although I thought it didn't have to do with gender disphoria and the Wikipedia page said otherwise

https://en.m.wikipedia.org/wiki/Transvestic_fetishism

it doesn't necessarily, but a lot of people can come into actual dysphoria through engaging in crossdressing. a lot of drag queens have gone on to transition

the distinction is important (you don't want to go calling trans people crossdressers for example) but they're not entirely unrelated
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Wowk01
05/24/19 6:17:42 PM
#39:


Here I started answering questions first, forgetting I had a new adventure to share today!

This morning I realized was the perfect opportunity to try my side-fantasy: pregnant in the car! I filled up 3 water balloons, put on a giant bra, regular panties, and maternity pants, and drove my brother to work. He stayed on his phone the whole time and didn't notice my slightly lumpy clothing under my normal leather jacket.

After I dropped him off, I parked behind a nearby financial facility and took off my shirt. Getting all those balloons into my clothes was a hell of a time! Kept getting stuck on the steering wheel! I was really scared some yahoo would come by and catch me in the middle of my perversion. But the coast was clear! I pulled the seatbelt over my giant tits, and strapped the belt above my belly (which was so huge, it was pushing on the steering wheel). Later I found out real pregnant women strap under the belly. Oh well! No baby for me to worry about.

Every bump and corner sent me jiggling like crazy! So hot! I kind of worried people would stare at me at stop lights. But I figured the heavy rain this morning would clear up the streets a bit, and I was right!

Walking back inside was the scariest part. Thought my dad might see me waddling in. But he didn't. Got back inside, and took more pictures with snapchat. Did you know it's easier to get full-body filter pictures if you use a mirror? I do now!
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Wowk01
05/24/19 6:20:57 PM
#40:


JCvgluvr posted...
This guy is definitely repressed.

Not gonna argue you, even if that sounded kind of condescending in my head. TheWitchMorgana basically covered where I'm coming from. This is one of the best thrills I've had since I discovered deviantart!

Smarkil posted...
oof not a good look

I look pretty ugly in the clothes, tbh. The snapchat filter kind of helps? The feeling is very pleasing, and that's the important thing for me.

captpackrat posted...
My SO was a nudist...

Shaving all but the arms? But hairy arms look so damn ugly when cross-dressing! Maybe it is better for hiding...
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Wowk01
05/24/19 6:38:18 PM
#41:


LeetCheet posted...
Aren't panties kinda tight for guys to wear though? How comfortable are they to wear though? Asking for a friend.

They move a lot. They ride into my leg tendons, and give me a wedgie. (That could be because I grabbed a cheap-ass polyester pack from walmart. See, they let you wear them and return them. Victoria's Secret doesn't. Trust me, I asked.)

Once I readjust the panties, they feel tiny and smooth. Almost like going commando, but better, because there's no seams to worry about!

-Komaiko54- posted...
captpackrat posted...
LeetCheet posted...
Aren't panties kinda tight for guys to wear though?

Women tend to have wider hips than men. And you can get panties in all sizes from kids up to BBW. Which is why I suggested telling the salesperson that it's for yourself, that way they can help you with sizing.


Sounds like that can be pretty embarrassing

Yeah it does. I won't try that shit in a million years!
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Lokarin
05/24/19 6:43:03 PM
#42:


Lol, on a lark I went into my old crossdress supplies - not sure why I kept them, but I found a pair of fake boobs!

heh
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Wowk01
05/24/19 6:46:44 PM
#43:


Lokarin posted...
Lol, on a lark I went into my old crossdress supplies - not sure why I kept them, but I found a pair of fake boobs!

If they still look convincing, maybe you should send them my way! Help a "girl" out. LOL

TheWitchMorgana posted...
SkynyrdRocker posted...
TheWitchMorgana posted...
JCvgluvr posted...
This guy is definitely repressed.

i dont think this means he's secretly trans if that's what you mean. some people just enjoy the performance of feminine dress but don't feel the need to identify differently. same idea with drag really

Yeah, crossdressing as a fetish is definitely a thing. Although I thought it didn't have to do with gender disphoria and the Wikipedia page said otherwise

https://en.m.wikipedia.org/wiki/Transvestic_fetishism

it doesn't necessarily, but a lot of people can come into actual dysphoria through engaging in crossdressing. a lot of drag queens have gone on to transition

the distinction is important (you don't want to go calling trans people crossdressers for example) but they're not entirely unrelated

Dysphoria? Shit...that actually kind of scares me. What if I'm doing permanent psychological damage to myself? I still have a faint hope I'll find a girlfriend someday. What if I'm causing "bedroom" problems for myself in the future?
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TheWitchMorgana
05/24/19 7:54:20 PM
#44:


Wowk01 posted...
Dysphoria? s***...that actually kind of scares me. What if I'm doing permanent psychological damage to myself? I still have a faint hope I'll find a girlfriend someday. What if I'm causing "bedroom" problems for myself in the future?

that's not how any of that works don't worry :P
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SkynyrdRocker
05/24/19 8:11:33 PM
#45:


Walmart lets you return worn underwear? Ew.
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Pus_N_Pecans
05/24/19 8:14:40 PM
#46:


TheWitchMorgana posted...
Wowk01 posted...
Dysphoria? s***...that actually kind of scares me. What if I'm doing permanent psychological damage to myself? I still have a faint hope I'll find a girlfriend someday. What if I'm causing "bedroom" problems for myself in the future?

that's not how any of that works don't worry :P

Yeah, this. You should be fine unless those feelings were already there.

Also, if you're genuinely interested, I have a pair of old breast forms that I don't need anymore, and if you wanted to pay for me to ship them to you I'd be willing to do it. I've wanted to donate them for a while now, but obviously I'm not gonna just give them to Goodwill or something.
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Revelation34
05/24/19 8:19:32 PM
#47:


Pus_N_Pecans posted...
I'm not gonna just give them to Goodwill or something.


Why not?
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Pus_N_Pecans
05/24/19 8:26:15 PM
#48:


Revelation34 posted...
Why not?

Because they're just gonna dump them in the trash, let's be honest.
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Revelation34
05/24/19 8:55:12 PM
#49:


Pus_N_Pecans posted...
Revelation34 posted...
Why not?

Because they're just gonna dump them in the trash, let's be honest.


You never know.
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synth_real
05/24/19 9:08:29 PM
#50:


Got any wigs, or considering it?
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