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Who would look good as a woman?

In one of the "Transbomer" threads someone wrote, "Yeah he doesn't look great as a woman honestly."

Which guys would look good and natural as a woman?

--Anonymous
replies 360Jun 13, 2017 2:08 PM +00:00

Young Leonardo DiCaprio- he even had the hips

s-media-cache-ak0.pinimg.com
--Anonymous
replies 1Jun 13, 2017 6:27 PM +00:00

The Biebs, of course

cdn01.cdn.justjared.com
--Baby Dykes Everywhere
replies 2Jun 13, 2017 6:28 PM +00:00

Hillary Clinton

--Anonymous
replies 3Jun 13, 2017 6:30 PM +00:00
The Biebs, of course

With those awful tattoos?

--Anonymous
replies 4Jun 13, 2017 6:38 PM +00:00

Candis looks good

upload.wikimedia.org
--Anonymous
replies 5Jun 13, 2017 6:48 PM +00:00
Who would look good presenting as a woman?

Fixed

--The XY chromosomes truth fairy
replies 6Jun 13, 2017 6:51 PM +00:00

Well hello!

static.buzznet.com
--Anonymous
replies 7Jun 13, 2017 6:55 PM +00:00

R7, Franco looks disgusting and dirty even as a woman.

--Anonymous
replies 8Jun 14, 2017 3:01 PM +00:00

Jude Law was stunning in drag in Sally Potters film.

--Anonymous
replies 9Jun 14, 2017 3:21 PM +00:00

Jason chaffetz is an ugly guy, but as a woman, he doesn't look half bad....

Imgur: The most awesome images on the Internet.
Imgur
--Anonymous
replies 10Jun 14, 2017 3:46 PM +00:00

My eyes! My eyes!

--Anonymous
replies 11Jun 14, 2017 3:49 PM +00:00

None of them. You can always tell. Even the lady boys from Thailand can't hide it, and they're the best you can get.

--Anonymous
replies 12Jun 14, 2017 3:51 PM +00:00

R12 = Jeremy Renner

--Anonymous
replies 13Jun 14, 2017 3:55 PM +00:00

James Marsden

--Anonymous
replies 14Jun 14, 2017 4:26 PM +00:00

The best, R13. Remember that. Forget I said that.

--Anonymous
replies 15Jun 14, 2017 4:28 PM +00:00

Timothée Chalamet makes a stunning woman based on these photos put through the FaceApp

s3.amazonaws.com
--Anonymous
replies 16Jun 14, 2017 4:37 PM +00:00

Been there. Done that.

--Chelsea M
replies 17Jun 14, 2017 5:40 PM +00:00

Miles Heizer and Paul Dano.

--Anonymous
replies 18Jun 14, 2017 5:52 PM +00:00

John Goodman.

--Anonymous
replies 19Jun 14, 2017 7:44 PM +00:00

John Goodman

--Anonymous
replies 20Jun 15, 2017 6:03 AM +00:00

None will look quite as good as me.

--Miss Lindsey
replies 21Jun 15, 2017 6:14 AM +00:00

You rang, OP?

68.media.tumblr.com
--C.
replies 22Jun 15, 2017 6:41 AM +00:00

Ken Burns

--Anonymous
replies 23Jun 15, 2017 7:48 AM +00:00

Ewwwwww, R23.

--Anonymous
replies 24Jun 15, 2017 8:26 AM +00:00

Rudy Giuliani

--Anonymous
replies 25Jun 15, 2017 9:00 AM +00:00

Who's that at r22?

--Bad hair.
replies 26Jun 15, 2017 6:31 PM +00:00

Miss Cillian Murphy, R26.

--Anonymous
replies 27Jun 15, 2017 6:33 PM +00:00

Thanks r27. Wow, he looks so twinkish in his that pic

--Anonymous
replies 28Jun 16, 2017 3:34 AM +00:00

Miss Cillian Murphy should transition. She doesn't look hot at all as "drag king."

--Anonymous
replies 29Jun 16, 2017 4:35 AM +00:00

Trey Gowdy - looks like a raging cunt. I don't know about attractive.

Brenton Thwaites - he's so pretty.

Barron Trump - looks androgynous, pouty lipped tranz somewhere on the spectrum. He's special..(needs)

--Anonymous in Kansas City
replies 30Jun 16, 2017 6:52 AM +00:00
Brenton Thwaites - he's so pretty.

He looks too manly.

--Anonymous
replies 31Jun 16, 2017 7:54 AM +00:00

Dave Foley always looked great as a woman.

--Anonymous
replies 32Jul 13, 2017 8:54 AM +00:00

Oh please, got this. ME!

--Caitlyn
replies 33Jul 13, 2017 9:05 AM +00:00

Mitch McConnell has the face of a kindly old grandmother.

--Anonymous
replies 34Jul 13, 2017 9:11 AM +00:00

Trump. All of them. Let's cut their dicks off now and get their balls rolling.

--Anonymous
replies 35Jul 13, 2017 9:15 AM +00:00
Mitch McConnell has the face of a kindly old grandmother.

He has the face of a turtle.

--Elaine Chow
replies 36Jul 13, 2017 9:21 AM +00:00

You, OP, you would look good as a woman. I can tell.

--Anonymous
replies 37Jul 13, 2017 9:26 AM +00:00

Tom Holland

i.ytimg.com
--Anonymous
replies 38Jul 13, 2017 9:41 AM +00:00

Jared Leto

s-media-cache-ak0.pinimg.com
--Thirty Seconds to Venus
replies 39Jul 13, 2017 10:19 AM +00:00

Melania has potential, with the right work undone.

www.omgblog.com
--Anonymous
replies 40Jul 13, 2017 10:22 AM +00:00

Please don't mention me.

topcelebrity2.free.fr
--Anonymous
replies 41Jul 13, 2017 12:08 PM +00:00

Rob Lowe

--Anonymous
replies 42Jul 13, 2017 12:10 PM +00:00

Tommy Haas, the over-the-hill tennis player. (Rumor has it he's a crossdresser.)

--Anonymous
replies 43Jul 13, 2017 2:02 PM +00:00

Chris Pine

--Anonymous
replies 44Sep 24, 2017 7:46 AM +00:00

No one can compete with Cillian Murphy, so they shouldn't even try.

bokunosekai.files.wordpress.com
--Anonymous
replies 45Sep 24, 2017 8:54 AM +00:00

Gael Garcia Bernal

--Anonymous
replies 46Sep 24, 2017 4:39 PM +00:00

Milo Yiannopoulos, or at least he'd look better as a woman

--Anonymous
replies 47Sep 24, 2017 4:42 PM +00:00

Mmmmmm tell me more

--Eddie M, revving up the van
replies 48Sep 24, 2017 4:46 PM +00:00

I used to think this guy did, but it's only the coyness and flirtation of the eyes. The nose is too prominent, and the inverted triangle of the high, defined cheekbones and pointed chin make the face clownish, which it's really meant to be rather than feminine.

Offsite Link
--Anonymous
replies 49Sep 24, 2017 4:51 PM +00:00

Trevor Donovan was born to be a woman.

--Anonymous
replies 50Sep 24, 2017 5:02 PM +00:00

I am dude and I don't even look good as a dude, but I would make one God awful looking woman.

--Anonymous
replies 51Sep 24, 2017 5:23 PM +00:00

It wouldn't take much, r47. He already looks like Alice Ghostley.

images.zap2it.com
--Anonymous
replies 52Sep 24, 2017 5:36 PM +00:00

Joan Crawford

--Bette Davis
replies 53Sep 24, 2017 5:55 PM +00:00

Ben Barnes

--Anonymous
replies 54Sep 25, 2017 4:15 AM +00:00

David Muir

--Anonymous
replies 55Sep 25, 2017 7:03 AM +00:00

Rob Lowe

--Anonymous
replies 56Sep 27, 2017 8:42 AM +00:00

James Marsden

--Anonymous
replies 57Sep 30, 2017 11:07 AM +00:00

Matt Dillon

--Anonymous
replies 58Oct 1, 2017 5:51 AM +00:00

Jared Kushner

--Senatrice Graham
replies 59Oct 1, 2017 6:03 AM +00:00

Guy Pearcce

--Anonymous
replies 60Oct 2, 2017 4:45 AM +00:00

I present for your inspection, Miss Mitch McConnell.

i.imgur.com
--Anonymous
replies 61Oct 2, 2017 5:55 AM +00:00

James Bradley

--Anonymous
replies 62Oct 2, 2017 10:48 AM +00:00
James Bradley

Why him? He has a very masculine face.

--Anonymous
replies 63Oct 2, 2017 10:57 AM +00:00

Michael Pitt

--Anonymous
replies 64Oct 2, 2017 11:07 AM +00:00

Josh Hartnett

--Anonymous
replies 65Oct 3, 2017 5:59 AM +00:00

Lucas Till (MacGyver)

--Anonymous
replies 66Oct 5, 2017 6:49 AM +00:00

None of them. Even LaVerne Cox still looks like a drag queen.

--Anonymous
replies 67Oct 5, 2017 6:54 AM +00:00

Good choice, R66. Pity about his neck mole.

--Anonymous
replies 68Oct 5, 2017 6:57 AM +00:00

Lucas Till almost looks like a woman without any makeup.

--Anonymous
replies 69Oct 5, 2017 7:03 AM +00:00

I don't know that it's good, but our president does look like an actual woman. His mother.

shawglobalnews.files.wordpress.com
--Anonymous
replies 70Oct 5, 2017 7:22 AM +00:00

Anyone that "Female" looking app? Want to run Lucas Till through it?

--Anonymous
replies 71Oct 5, 2017 8:11 AM +00:00

Dave Foley is the winner:

encrypted-tbn0.gstatic.com
--more feminine than average for a woman
replies 72Oct 5, 2017 8:46 AM +00:00

....

upload.wikimedia.org
--Anonymous
replies 73Oct 5, 2017 8:48 AM +00:00
Which guys would look good and natural as a woman?

Define "woman", OP.

--Curious
replies 74Oct 5, 2017 8:50 AM +00:00

Looking like a "woman" a straight guy would want to fck.

--Anonymous
replies 75Oct 5, 2017 9:32 AM +00:00

Mike Vogel would make a beautiful woman.

--Anonymous
replies 76Oct 5, 2017 8:12 PM +00:00

I can see that, R76.

mediamass.net
--Anonymous
replies 77Oct 5, 2017 8:34 PM +00:00

Billy Crudup made a pretty girl.

--Anonymous
replies 78Oct 5, 2017 9:12 PM +00:00

Jude Law

--Anonymous
replies 79Oct 5, 2017 10:46 PM +00:00

Ian Somerhalder. He's quite pretty in person, hence the scruff and the squint in more recent photos. This is an older one:

ewedit.files.wordpress.com
--Anonymous
replies 80Oct 5, 2017 11:07 PM +00:00

It's the jaw & the adams apple that gives away. Any pretty male actor who doesn't have a very strong jawline like Jared Leto, Eddie Redmayne, Jude law, Timothy Chalamet, the guy that Sam Smith is dating, Tom Holland....there are so many would make a pretty woman.

--Anonymous
replies 81Oct 5, 2017 11:22 PM +00:00

Johnny Depp

--Anonymous
replies 82Oct 7, 2017 7:43 AM +00:00

Despite the leathery appearance and bad wigs, Melania pulls off a woman... more or less.

--Anonymous
replies 83Oct 7, 2017 7:47 AM +00:00

the Senatrice!

--Anonymous
replies 84Oct 7, 2017 7:51 AM +00:00

Rafael Nadal

--Anonymous
replies 85Oct 7, 2017 1:11 PM +00:00

A young Pierce Brosnan

--Anonymous
replies 86Oct 8, 2017 5:57 AM +00:00

Ugh 🚨autogynophile circle jerk alert! 🚨

Anyway it’s not the jaw that’s the “giveaway”, there’s plenty of gals with big jaws (that tranny looking bitch who speaks for the president) and some have prominent adams apple (Maddow). No the ultimate tell is the brow riidge and how deep set the eyes are, along with how Jorge the eyes are relative to face (women have dramatically smaller faces/heads).

--Anonymous
replies 87Oct 8, 2017 6:15 AM +00:00

Jorge???? I meant LARGE

--Anonymous
replies 88Oct 8, 2017 6:16 AM +00:00

Jonathan Groff

--Anonymous
replies 89Oct 9, 2017 7:43 AM +00:00

Stephen Amell -- perfect heart-shaped face and full lips.

--Anonymous
replies 90Oct 10, 2017 9:01 AM +00:00

Matthew Gray Gubler -- even has the body-type of a female fashion model.

--Anonymous
replies 91Oct 11, 2017 9:22 AM +00:00

John Schneider

--Anonymous
replies 92Oct 12, 2017 2:43 AM +00:00

Maybe John Schneider YOUNG?

--Anonymous
replies 93Oct 12, 2017 7:19 AM +00:00

Thomas Gibson

--Anonymous
replies 94Oct 13, 2017 10:08 AM +00:00

Ben Hardy

--Anonymous
replies 95Oct 14, 2017 12:06 PM +00:00

Does Ben Hardy appeal to any DL trolls?

--Anonymous
replies 96Oct 14, 2017 12:13 PM +00:00

Steve Kornacki

--Anonymous
replies 97Oct 16, 2017 4:46 AM +00:00

Congressman Eric Swalwell would look beautiful as a congresswoman.

--Anonymous
replies 98Oct 17, 2017 12:27 PM +00:00

No he wouldn't, R98. He has a block face.

ballotpedia.s3.amazonaws.com
--Anonymous
replies 99Oct 17, 2017 4:28 PM +00:00

Stephen Colbert

--Anonymous
replies 100Oct 20, 2017 6:02 AM +00:00

Michael Fassbender

--Anonymous
replies 101Oct 21, 2017 6:06 AM +00:00

Matt Dallas

--Anonymous
replies 102Oct 23, 2017 5:51 AM +00:00

Fassbender has no lips and a skull like a cinder block; would NOT look good as a woman.

--Anonymous
replies 103Oct 23, 2017 5:53 AM +00:00

Jonathan Bennett

--Anonymous
replies 104Oct 25, 2017 5:33 AM +00:00

Colton Haynes

--Anonymous
replies 105Oct 26, 2017 12:14 PM +00:00

Merlyn Wood from Brockhampton

dazedimg.dazedgroup.netdna-cdn.com
--Anonymous
replies 106Oct 27, 2017 8:27 AM +00:00

****

www.famousbirthdays.com
--Anonymous
replies 107Oct 27, 2017 8:34 AM +00:00

Straight too (but gay friendly ) from what I can glean

www.famousbirthdays.com
--Anonymous
replies 108Oct 27, 2017 8:37 AM +00:00

The Triage Guy

--Anonymous
replies 109Oct 27, 2017 9:12 PM +00:00

Should be "The TRIVAGO Guy"

--Anonymous
replies 110Oct 27, 2017 9:13 PM +00:00

Ernest Borgnine

--Anonymous
replies 111Oct 27, 2017 9:19 PM +00:00

Stephen Colbert

--Anonymous
replies 112Oct 27, 2017 9:48 PM +00:00

Bruno Mars

i.pinimg.com
--He's so petite
replies 113Oct 27, 2017 10:30 PM +00:00

R113 Omg he really does! Always wondered why his face always seemed “off” to me

--Anonymous
replies 114Oct 27, 2017 10:36 PM +00:00

Teddy Geiger Obviously he/she thinks so.

--Anonymous
replies 115Oct 28, 2017 7:07 AM +00:00

Scott Disick

--Anonymous
replies 116Oct 29, 2017 7:40 AM +00:00

Gavin Newsom

--Anonymous
replies 117Oct 30, 2017 4:56 AM +00:00

Luke Norris -- "Dr. Dwight Enys" on Poldark

--Anonymous
replies 118Oct 31, 2017 5:21 AM +00:00

Tom Cruise

--Anonymous
replies 119Nov 1, 2017 4:35 AM +00:00

Do old dykes count as “women”...if so: Clay Aiken (owns this thread)

--Anonymous
replies 120Nov 2, 2017 3:10 AM +00:00

Max Theriot from Bates Motel

--Anonymous
replies 121Nov 2, 2017 7:37 AM +00:00

Lee Pace. His neck is too thick, but it's still pretty convincing.

--Anonymous
replies 122Nov 2, 2017 7:54 AM +00:00

Dylan Strawberry

--Anonymous
replies 123Nov 4, 2017 6:26 AM +00:00

Harvey Weinstein

--Anonymous
replies 124Nov 4, 2017 6:36 AM +00:00

Sebastian Stan

--Anonymous
replies 125Nov 6, 2017 1:26 PM +00:00

Luke MacFarlane

--Anonymous
replies 126Nov 7, 2017 5:59 AM +00:00

James Wolk -- Beautiful big eyes and lush full lips.

--Anonymous
replies 127Nov 8, 2017 4:42 AM +00:00

Jenny Thunder

68.media.tumblr.com
--Anonymous
replies 128Nov 8, 2017 4:56 AM +00:00

[R. 128] Who is Jenny Thunder? She looks familiar. TIA.

--Anonymous
replies 129Nov 8, 2017 6:33 AM +00:00

Donald Trump

--Anonymous
replies 130Nov 8, 2017 6:37 AM +00:00

Really?

--Anonymous
replies 131Nov 8, 2017 6:59 AM +00:00

Leonardo was surprisingly good in the lead role of THE JUDY ZiPPER STORY (1998).

media.fromthegrapevine.com
--Anonymous
replies 132Nov 8, 2017 7:34 AM +00:00

Jensen Ackles, R129.

--Anonymous
replies 133Nov 8, 2017 8:32 AM +00:00

Jensen Ackles -- next to Miss Cillian Murphy -- owns this thread.

--Anonymous
replies 134Nov 8, 2017 11:45 AM +00:00

A young Roger Taylor from Queen

i.pinimg.com
--Anonymous
replies 135Nov 8, 2017 12:34 PM +00:00

Lil Peep

i.pinimg.com
--Anonymous
replies 136Nov 8, 2017 12:37 PM +00:00

....

355 Likes, 2 Comments - LIL PEEP FAN PAGE (@lilpeepdaily) on Instagram: “????: @omgimwigs #lilpeep @lilpeep #comeoverwhenyouresober #gothboiclique”
Instagram
--Anonymous
replies 137Nov 8, 2017 12:41 PM +00:00

Daniel Radcliffe

www.comedycentral.co.uk
--Anonymous
replies 138Nov 8, 2017 1:02 PM +00:00

Rain Bi, Korean Pop singer

s3.amazonaws.com
--Yes, I'm a Rice Kween
replies 139Nov 8, 2017 1:06 PM +00:00

Ron Perlman

--Anonymous
replies 140Nov 8, 2017 1:16 PM +00:00

A young Peter Capaldi

i.pinimg.com
--Anonymous
replies 141Nov 8, 2017 1:24 PM +00:00

....

i.pinimg.com
--Anonymous
replies 142Nov 8, 2017 1:28 PM +00:00

Andreja Pejic

cdn.newsapi.com.au
--Anonymous
replies 143Nov 8, 2017 2:44 PM +00:00

Here's a picture of Andreja Pejic on the right before gender reassignment.

assets.rbl.ms
--Anonymous
replies 144Nov 8, 2017 2:48 PM +00:00

Here's another picture of Andreja Pejic when she was a man.

i.pinimg.com
--Anonymous
replies 145Nov 8, 2017 2:52 PM +00:00

Andreja Pejic, a transgender, who used to be a man, was originally hired as a male model. Because of her too girly face, designers started putting her in women's clothes.

oystercoloredvelvet.com
--Anonymous
replies 146Nov 8, 2017 3:24 PM +00:00

Noel Fielding, a British comedian

cdn-04.independent.ie
--Anonymous
replies 147Nov 8, 2017 7:19 PM +00:00

Katy Perry would be very pretty as a woman. Maybe some day we'll see that.

--Anonymous
replies 148Nov 9, 2017 6:13 AM +00:00

Chandler Massey

John Chandler (WNBC New York)

--Anonymous
replies 149Nov 12, 2017 10:11 AM +00:00

Jeremy Peters MSNBC Gorgeous with a long swan-like neck.

--Anonymous
replies 150Nov 16, 2017 5:23 AM +00:00

R149, Chandler may be cute but he doesn’t look like a woman.

--Anonymous
replies 151Nov 16, 2017 9:21 AM +00:00

Michael Jackson in the early 90s.

Found on Google from michael-jackson.wikia.com
goo.gl
--Jermaine
replies 152Nov 16, 2017 11:00 AM +00:00

Eric Bana

--Anonymous
replies 153Nov 18, 2017 10:39 AM +00:00

R59 ...Good one!

--Anonymous
replies 154Nov 18, 2017 12:23 PM +00:00

Taylor Hanson

--Anonymous
replies 155Nov 19, 2017 5:38 AM +00:00

Douglas Booth

--Anonymous
replies 156Nov 20, 2017 4:52 AM +00:00

Matt Barr -- a blond guy becomes a blonde beauty

--Anonymous
replies 157Nov 21, 2017 6:43 AM +00:00

Peter Jennings In fact, he was a crossdresser (convincing one) under the drag name, "Jennifer Peters."

--Anonymous
replies 158Nov 22, 2017 9:11 PM +00:00

Alex James, from Blur(in a video clip but I can't recall which song it was) and Johnny Depp passed pretty well, I think, in an episode of Jump Street.

--Back then, notsomuch now..
replies 159Nov 22, 2017 9:17 PM +00:00

Young East Asian male ‘idols’ (popular tv actors/musical stars/magazine models) can look utterly convincing as pretty girls.

Subtle crossdressing is also considered as an innocuous pastime over there, especially in Japan. A young Japanese man dressing as a girl has ‘cute’ or ‘sweet’ & wholesome connotations totally opposite to the expectations Westerners have. Perhaps it’s easier to do in certain Asian societies where the rigid social mores clearly define a limited female role of passivity.

For an example, actor Shogo Suzuki can pass (the first ‘girl’ in the clip below).

Video fragment of Miss Boys: Yuujo no yukue (traces of friendship) Subs on this video were done in a rush and therefor some translations aren't exactly perfe...
YouTube
--Anonymous
replies 160Nov 24, 2017 1:55 AM +00:00

R157 I would love to see that, I covet a cute andro blond and Matt looks pretty as sin clean-shaven & with longer hair.

Sadly though, I fear the window has closed on him passing as a cute young woman because he has gotten too muscular & wiry and his face has naturally aged too much. Wonder if he’d look as a more mature gal?

i.pinimg.com
--Anonymous
replies 161Nov 24, 2017 2:01 AM +00:00

Many male models would look good as women such as Mark Vanderloo. Perfect lush full lips.

--Anonymous
replies 162Nov 25, 2017 4:58 AM +00:00

Creepy tranny chasers ITT

--Anonymous
replies 163Nov 25, 2017 5:56 AM +00:00

Charlie Heaton

--Anonymous
replies 164Nov 27, 2017 4:14 AM +00:00

150 replies deep and no-one said Cole Sprouse yet. You all feeling alright?

And Dylan would make the prettier wench.

--Anonymous
replies 165Nov 28, 2017 2:35 PM +00:00

Greg Kinnear

--Anonymous
replies 166Nov 28, 2017 7:21 PM +00:00

[R. 165] Wow! The twin Spouse "SISTERS."

--Anonymous
replies 167Nov 29, 2017 5:34 AM +00:00

Why do gay men dress up as women? Why do drag queens look so ugly? Is it because of cunt envy?

--Anonymous
replies 168Nov 30, 2017 7:27 PM +00:00

R168, it’s because their mothers were all maids.

--Gore Vidal
replies 169Nov 30, 2017 7:35 PM +00:00

Most of the men on this thread look very pretty as women. In fact, a few even look better as women than as men!

--Anonymous
replies 170Dec 1, 2017 5:00 AM +00:00

R45 strange that Kitty of ‘Breakfast on Pluto’ looks just like Grace Burgess (played by Annabelle Wallis), who was the main female love-interest to Cillian’s character Tommy Shelby in ‘Peaky Blinders’...

i2-prod.birminghammail.co.uk
--Anonymous
replies 171Dec 1, 2017 5:48 AM +00:00

R171, Miss Cillian was prettier.

--Anonymous
replies 172Dec 1, 2017 5:51 AM +00:00

Oh, don't mind me you cunts!

2.bp.blogspot.com
--Anonymous
replies 173Dec 1, 2017 5:54 AM +00:00

Tony Curtis in Some Like It Hot

--Anonymous
replies 174Dec 2, 2017 6:32 AM +00:00

Jared Leto. Michael Pitt.

--Anonymous
replies 175Dec 2, 2017 6:45 AM +00:00

When younger, Damon Albarn would have made a pretty Winona-esque gamine.

Now he’s in his late-40’s, husky & grizzled, not so much. Same goes for Alex James.

picture-cdn.wheretoget.it
--Anonymous
replies 176Dec 2, 2017 7:48 AM +00:00
Oh, don't mind me you cunts!

What’s that?

--Anonymous
replies 177Dec 2, 2017 8:48 AM +00:00

When younger, Lyle Wagoner, from The Carold Burnett Show, would have been much prettier than Carol.

--Anonymous
replies 178Dec 2, 2017 9:53 AM +00:00

Anyone would have been prettier than Carol.

--Vicki Lawrence
replies 179Dec 2, 2017 10:12 AM +00:00

Froy Gutierrez

--Anonymous
replies 180Dec 3, 2017 5:12 AM +00:00

Timothée looks like a young Camille Paglia but feminine

--Anonymous
replies 181Dec 3, 2017 5:20 AM +00:00

Toby Regbo

--Anonymous
replies 182Dec 3, 2017 3:21 PM +00:00

Adam Scott (golfer)

--Anonymous
replies 183Dec 4, 2017 9:25 AM +00:00

Billy Bush

--Anonymous
replies 184Dec 5, 2017 4:20 AM +00:00

Tyler Breeze is pretty cute like a girl, facially.

media.giphy.com
--Anonymous
replies 185Dec 6, 2017 3:38 AM +00:00

Colton Haynes-if he took drag seriously (the eyebrows gotta go) - would make a beautiful woman. He has the same basic bone structure/features as Angelina Jolie.

imageslogotv-a.akamaihd.net
--Anonymous
replies 186Dec 6, 2017 4:02 AM +00:00

Vince Neil.

i.pinimg.com
--Nikki Sixx, posting from the year 1985
replies 187Dec 6, 2017 4:31 AM +00:00

Josh Henderson

--Anonymous
replies 188Dec 7, 2017 5:33 AM +00:00
Josh Henderson

Why him?

--Anonymous
replies 189Dec 7, 2017 6:04 AM +00:00

Heart-shaed face, full lush lips and small jaw.

--Anonymous
replies 190Dec 7, 2017 6:47 AM +00:00

Thanks, R190.

--Anonymous
replies 191Dec 7, 2017 7:17 AM +00:00

Arnie Hammer

--Anonymous
replies 192Dec 10, 2017 12:25 PM +00:00

R192 He's ugly

--Anonymous
replies 193Dec 10, 2017 12:35 PM +00:00

Eddie Redmayne

images.indianexpress.com
--Anonymous
replies 194Dec 10, 2017 12:37 PM +00:00

Johnathan Taylor Thomas

--Anonymous
replies 195Dec 10, 2017 12:39 PM +00:00

Michael Jackson

mjvibe.com
--Anonymous
replies 196Dec 10, 2017 12:39 PM +00:00

Bon Jovi

--Anonymous
replies 197Dec 10, 2017 12:40 PM +00:00

Jon Bon Jovi and Richie Sambora

cdn-www.cracked.com
--Anonymous
replies 198Dec 10, 2017 12:40 PM +00:00

Simon Le Bon

i.pinimg.com
--Anonymous
replies 199Dec 10, 2017 12:42 PM +00:00

Bruce Jenner

--Anonymous
replies 200Dec 10, 2017 12:43 PM +00:00

I’m too tall, 6’2”.

--Anonymous
replies 201Dec 10, 2017 12:43 PM +00:00

Mick Jagger

pbs.twimg.com
--Anonymous
replies 202Dec 10, 2017 12:44 PM +00:00

R201 No problem I'm 6' 2¾"

pinthisstar.com
--Elizabeth Debicki
replies 203Dec 10, 2017 12:47 PM +00:00

Steven Tyler and Mick Jagger

--Anonymous
replies 204Dec 10, 2017 12:50 PM +00:00

David Bowie

--Anonymous
replies 205Dec 10, 2017 12:50 PM +00:00
Michael Jackson

Not any more.

--H.
replies 206Dec 10, 2017 1:05 PM +00:00

Robert Sean Leonard

--Anonymous
replies 207Dec 11, 2017 4:28 AM +00:00

Young Robin Zander from Cheap Trick

lastfm-img2.akamaized.net
--Anonymous
replies 208Dec 11, 2017 4:45 PM +00:00

Orlando Bloom

i.pinimg.com
--Anonymous
replies 209Dec 11, 2017 4:59 PM +00:00

Bret McKenzie, actor/comedian

78.media.tumblr.com
--Anonymous
replies 210Dec 11, 2017 5:04 PM +00:00

Finn Wolfhard. I guess more girl than woman.

Finn Wolfhard by Sacha Maric for Nylon Guys Magazine September 2017 - Stranger Things (1)
Minimal. / Visual.
--Anonymous
replies 211Dec 11, 2017 5:09 PM +00:00

Young David Sylvian, English singer/musician

media.gettyimages.com
--Anonymous
replies 212Dec 11, 2017 5:18 PM +00:00

Roy Moore

--Anonymous
replies 213Dec 12, 2017 8:09 PM +00:00

A young Alec Baldwin -- blue eyes, small jaw and lush-full lips.

--Anonymous
replies 214Dec 13, 2017 12:10 PM +00:00

Ms. Ryan PhiliPAY.

--Anonymous
replies 215Dec 13, 2017 1:35 PM +00:00

Chaz Bono

--Anonymous
replies 216Dec 13, 2017 1:42 PM +00:00

Tatum Channing

--Anonymous
replies 217Dec 13, 2017 1:43 PM +00:00

R194 looks like Carrie Brownstein.

--Anonymous
replies 218Dec 13, 2017 1:53 PM +00:00

R217 forgot to post

i.ytimg.com
--Anonymous
replies 219Dec 13, 2017 1:57 PM +00:00

Troye Sivan in drag at 2:31

DAY 461 // 9TH MAY 2014 Go Subscribe to Alfie http://www.youtube.com/PointlessBlog Zoe http://www.youtube.com/zoella280390 Joey https://www.youtube.com/user/...
YouTube
--Anonymous
replies 220Dec 13, 2017 6:24 PM +00:00

A young Robert Redford

--Anonymous
replies 221Dec 16, 2017 8:39 AM +00:00

No, just no, R221.

--Anonymous
replies 222Dec 16, 2017 8:45 AM +00:00

Pitt

DiCaprio

--Anonymous
replies 223Dec 16, 2017 8:52 AM +00:00

Colton...

“@ColtonLHaynes This gender bender prefers you with black wavy hair.”
Twitter
--Anonymous
replies 224Dec 16, 2017 8:54 AM +00:00

Angelina Jolie and Jennifer Maniston

--Anonymous
replies 225Dec 16, 2017 8:54 AM +00:00

Brad Pitt

cdn.cnn.com
--Anonymous
replies 226Dec 16, 2017 8:55 AM +00:00

Leonardo DiCaprio!

cdn-wpmsa.defymedia.com
--Anonymous
replies 227Dec 16, 2017 8:58 AM +00:00

Chris Pine

pbs.twimg.com
--Anonymous
replies 228Dec 16, 2017 9:07 AM +00:00

Gael Garcia Bernal

i.pinimg.com
--Anonymous
replies 229Dec 16, 2017 9:07 AM +00:00

George Clooney

img.buzzfeed.com
--Anonymous
replies 230Dec 16, 2017 9:10 AM +00:00

Johnny Depp

i.pinimg.com
--Anonymous
replies 231Dec 16, 2017 9:11 AM +00:00

Benedict Cumberbatch

img.buzzfeed.com
--Anonymous
replies 232Dec 16, 2017 9:16 AM +00:00

Patrick Swayze

media.baselineresearch.com
--Anonymous
replies 233Dec 16, 2017 2:37 PM +00:00

All from R224 to R233 make damn ugly-looking women except Brad Pitt. He looks more beautiful than most women in the pic at R226.

--Anonymous
replies 234Dec 16, 2017 3:36 PM +00:00

Carter Oosterhouse

--Anonymous
replies 235Dec 17, 2017 6:04 AM +00:00

Thor

i.pinimg.com
--Anonymous
replies 236Dec 17, 2017 10:44 AM +00:00

Carter Oosterhouse is a real name? WTF!

--Anonymous
replies 237Dec 17, 2017 11:14 AM +00:00

Carter Oosterhouse's real name is Ezra Cohen.

--Anonymous
replies 238Dec 17, 2017 12:22 PM +00:00

Alexander Dreymon

--Anonymous
replies 239Dec 18, 2017 5:58 AM +00:00

Garrett Clayton would make a beautiful woman. In fact, he was born into the wrong sex.

--Anonymous
replies 240Dec 18, 2017 10:58 AM +00:00

Why do you say that, R240?

--Anonymous
replies 241Dec 18, 2017 11:02 AM +00:00

Jared Leto

--Anonymous
replies 242Dec 18, 2017 11:08 AM +00:00

Kate Winslet

--Anonymous
replies 243Dec 18, 2017 11:09 AM +00:00

R239 Dreymon would make a great drag queen or transverstite, but his jaw is too square. Beautiful eyes and mouth though

--Anonymous
replies 244Dec 18, 2017 11:12 AM +00:00

David Duchovny

--Anonymous
replies 245Dec 19, 2017 8:31 AM +00:00

James Norton

--Anonymous
replies 246Dec 20, 2017 4:33 AM +00:00

Jeffrey Donovan

--Anonymous
replies 247Dec 21, 2017 7:08 AM +00:00

1990s Liam Gallagher. [Yes, even with his eyebrow.]

--Anonymous
replies 248Dec 21, 2017 7:16 AM +00:00

Sam Heughan

--Anonymous
replies 249Dec 22, 2017 3:54 AM +00:00

Steven Pasquale

--Anonymous
replies 250Dec 23, 2017 5:18 AM +00:00

Steven Pasquale's bad nose job really makes him look effeminate. It's a good start to becoming a beautiful woman.

--Anonymous
replies 251Dec 23, 2017 1:39 PM +00:00

President Trump

Because he is THE BEST at everything he does and so if he wanted to be a woman he'd make a GREAT woman. Probably the BEST WOMAN EVER.

He'd Make Women Great Again, he would!

--Anonymous
replies 252Dec 23, 2017 1:41 PM +00:00

Billy Crudup

--Anonymous
replies 253Dec 24, 2017 6:59 AM +00:00

Elvis Presley

--Anonymous
replies 254Dec 24, 2017 8:34 AM +00:00

Santa. (A jolly fat woman.)

--Anonymous
replies 255Dec 25, 2017 6:48 AM +00:00

Garrett Hedlund

--Anonymous
replies 256Dec 26, 2017 6:00 AM +00:00

David Tennant.

images1.fanpop.com
--Anonymous
replies 257Dec 26, 2017 7:10 AM +00:00

Ryan Gosling Same shaped face as David Tennant

--Anonymous
replies 258Dec 27, 2017 6:34 AM +00:00

David Tennant is way more cute than Gosling.

--Anonymous
replies 259Dec 27, 2017 10:55 AM +00:00

Paul McCartney

--Anonymous
replies 260Dec 27, 2017 8:49 PM +00:00

Dan Stevens "Matthew Crawley" Downton Abbey

--Anonymous
replies 261Dec 28, 2017 3:29 PM +00:00

Gosling is ugly

--Anonymous
replies 262Dec 28, 2017 4:08 PM +00:00

Jon Bon Jovi looks super femme here, pretty even.

78.media.tumblr.com
--Anonymous
replies 263Dec 28, 2017 4:18 PM +00:00

Gossling is fug.

The gif at R263 is very feminine.

--Anonymous
replies 264Dec 29, 2017 10:22 AM +00:00

Michael Vartan

--Anonymous
replies 265Dec 30, 2017 7:03 AM +00:00

John Travolta

dailypost.ng
--Anonymous
replies 266Dec 30, 2017 12:11 PM +00:00

Rudy Giuliani

i.ytimg.com
--Anonymous
replies 267Dec 30, 2017 12:15 PM +00:00

Matt Lauer

media1.s-nbcnews.com
--Anonymous
replies 268Dec 30, 2017 12:19 PM +00:00

Lauer is so unbelievably gross. Ick!!!

--Anonymous
replies 269Dec 30, 2017 2:11 PM +00:00

Lauer is gross in MANY ways!

--Anonymous
replies 270Dec 30, 2017 6:27 PM +00:00

Ryan Seacrest

--Anonymous
replies 271Dec 31, 2017 6:59 AM +00:00

Charlie Hunnam

--Anonymous
replies 272Jan 1, 2018 11:27 AM +00:00

Freddie Highmore

--Anonymous
replies 273Jan 2, 2018 3:56 AM +00:00

Jeff Ward. First saw him on SyFy, Channel Zero:The No-End house which was pretty good; he's also on Agents of Shield. Very pretty eyes and face.

Jeff Ward
IMDb
--Anonymous
replies 274Jan 2, 2018 9:44 PM +00:00

P. Allen Smith -- the gardener

--Anonymous
replies 275Jan 4, 2018 7:13 AM +00:00

Eddie Redmayne

--Anonymous
replies 276Jan 4, 2018 7:16 AM +00:00

James McAvoy

--Anonymous
replies 277Jan 4, 2018 7:16 AM +00:00

Simon Baker

--Anonymous
replies 278Jan 5, 2018 12:39 PM +00:00

Mangelina

--Anonymous
replies 279Jan 5, 2018 1:10 PM +00:00

Dylan Sprayberry

--Anonymous
replies 280Jan 6, 2018 7:09 AM +00:00

Gavin Newsom

--Anonymous
replies 281Jan 8, 2018 6:16 AM +00:00

Bobby Flay

--Anonymous
replies 282Jan 9, 2018 6:35 AM +00:00
i.pinimg.com
--Anonymous
replies 283Jan 9, 2018 3:31 PM +00:00

Chris Evans

pbs.twimg.com
--Anonymous
replies 284Jan 9, 2018 7:01 PM +00:00

[R 283] I don't recognize the beauty. Who is she?

--Anonymous
replies 285Jan 10, 2018 6:25 AM +00:00

R285 Hugh Laurie

--Anonymous
replies 286Jan 10, 2018 6:26 AM +00:00

Peter Scolari

--Anonymous
replies 287Jan 11, 2018 3:56 AM +00:00

Pat Robertson

--Anonymous
replies 288Jan 11, 2018 4:12 AM +00:00

.......Judge Judy

--Anonymous
replies 289Jan 11, 2018 4:15 AM +00:00

When crossdressed, 21y.o. Corey Haim (RIP) looked cute as a button in a sturdy Lilith-Fair lesbian way.

c8.alamy.com
--Anonymous
replies 290Jan 11, 2018 7:48 AM +00:00

Jim Carrey

--Anonymous
replies 291Jan 11, 2018 9:08 AM +00:00

James Franco

i.pinimg.com
--Anonymous
replies 292Jan 11, 2018 9:12 AM +00:00

Better than Angelina Ho

i.dailymail.co.uk
--Anonymous
replies 293Jan 11, 2018 9:13 AM +00:00

Shah Rukh Khan

www.bollywoodtabloid.com
--Anonymous
replies 294Jan 11, 2018 9:42 AM +00:00

Peter Gallagher

--Anonymous
replies 295Jan 12, 2018 8:47 AM +00:00

Just tried the Face App on Peter Gallagher -- he looks just like Jackie O.

(Anyone know how to post a photo?)

--Anonymous
replies 296Jan 12, 2018 9:07 AM +00:00

Peter Scolari

--Anonymous
replies 297Jan 13, 2018 6:48 AM +00:00

Keith Urban

--Professional beard Nicole
replies 298Jan 13, 2018 7:41 AM +00:00

Charles Busch

i.pinimg.com
--Anonymous
replies 299Jan 13, 2018 7:43 AM +00:00

Steve Buscemi

i.imgur.com
--Anonymous
replies 300Jan 13, 2018 7:45 AM +00:00

Stephen Dorff

www.listsworld.com
--Anonymous
replies 301Jan 13, 2018 7:46 AM +00:00

James Franco

www.listsworld.com
--Anonymous
replies 302Jan 13, 2018 7:51 AM +00:00

David Tennant

David Tennant As A Woman (Very Freeky and real) No copyright intended
YouTube
--Anonymous
replies 303Jan 13, 2018 7:53 AM +00:00

Some of these decidedly do not "look good as a woman".

--Anonymous
replies 304Jan 13, 2018 7:57 AM +00:00

David Tennant plays the Doctor's "gorgeous time traveling assistant.

A sketch on Friday Night Project... David Tennant plays the part of the Doctor's "gorgeous time traveling assistant." Not much to it, but hey, David in a dress.
YouTube
--Anonymous
replies 305Jan 13, 2018 7:57 AM +00:00

Max Theriot

--Anonymous
replies 306Jan 14, 2018 6:32 AM +00:00

Max is beautiful. Excellent choice.

--Anonymous
replies 307Jan 14, 2018 7:18 AM +00:00
pbs.twimg.com
--Anonymous
replies 308Jan 14, 2018 2:31 PM +00:00

Chelsea Manning

eviltwinbooking.org
--Anonymous
replies 309Jan 14, 2018 6:42 PM +00:00

Ken Burns

--Anonymous
replies 310Jan 15, 2018 7:04 AM +00:00

Michael Woods, BBC Presenter/Host

--Anonymous
replies 311Jan 16, 2018 12:51 PM +00:00

Neil Patrick Harris

i.pinimg.com
--Anonymous
replies 312Jan 16, 2018 7:05 PM +00:00

Patrick Dempsey

--Anonymous
replies 313Jan 18, 2018 1:42 PM +00:00

There used to be rumors on DL that Patrick Dempsey was a cross dresser and that he looked very attractive when so dressed.

--Anonymous
replies 314Jan 18, 2018 1:45 PM +00:00

^ that was Brad Pitt

--Anonymous
replies 315Jan 18, 2018 1:47 PM +00:00

Jeff Glor

--Anonymous
replies 316Jan 18, 2018 3:05 PM +00:00

R315, Brad Pitt dressed in drag for an edition of Rolling Stone. The rumors I read here were about Patrick Dempsey and Adam Scott, a pro golfer.

--Anonymous
replies 317Jan 18, 2018 3:08 PM +00:00

Rumoer about German tennis pro Tommy Haas being a crossdresser, too.

--Anonymous
replies 318Jan 18, 2018 3:25 PM +00:00

R315 if memory serves I think that rumor/blind was in fact about James Marsden.

--Anonymous
replies 319Jan 19, 2018 2:03 AM +00:00

Tom Hanks

i.pinimg.com
--Anonymous
replies 320Jan 19, 2018 2:08 AM +00:00

Taylor Lautner

Taylor Kitsch

Taylor Swift

Taylor Maydh

--Anonymous
replies 321Jan 19, 2018 2:26 AM +00:00

Alexander Skarsgard perhaps?

Offsite Link
--Anonymous
replies 322Jan 19, 2018 5:17 AM +00:00

Pretty actor Jordan Brower would make an interesting shy geeky lesbian.

www.teenidols4you.com
--Anonymous
replies 323Jan 19, 2018 5:52 AM +00:00

I always thought Jon Bon Jovi looked quite feminine.

mumfection.com
--Anonymous
replies 324Jan 19, 2018 6:01 AM +00:00

Trevor Donovan

--Anonymous
replies 325Jan 20, 2018 7:02 AM +00:00

Trevor had too much of a square masculine face.

--Anonymous
replies 326Jan 20, 2018 1:18 PM +00:00

Jeff Glor

--Anonymous
replies 327Jan 21, 2018 5:38 AM +00:00

Josh Duhamel

--Anonymous
replies 328Jan 23, 2018 12:42 PM +00:00

James Murray British Actor

--Anonymous
replies 329Jan 25, 2018 7:19 AM +00:00

Brad Pitt

mrwgifs.com
--Anonymous
replies 330Jan 29, 2018 2:10 AM +00:00

Jim Morrison of The Doors

img.wennermedia.com
--Anonymous
replies 331Jan 29, 2018 2:36 AM +00:00

Bob Barker when young

--Anonymous
replies 332Jan 30, 2018 8:06 AM +00:00

No one! Just another attempt by the transgenda Mafia to demasculinize men. No one who was born a man really looks great as a woman. It's the reason why drag queens are used for entertainment... because we're in on the joke. IT'S NOT MEANT TO BE TAKEN SERIOUSLY! Even RuPaul loves living as a man once his drag comes off!

--Anonymous
replies 333Jan 30, 2018 8:10 AM +00:00

Alexander Skarsgaard

--Anonymous
replies 334Jan 31, 2018 7:05 AM +00:00

John Leguizamo

--Anonymous
replies 335Feb 1, 2018 6:32 AM +00:00

The Ground Hog

--Anonymous
replies 336Feb 2, 2018 5:15 AM +00:00

Owen Campbell

pbs.twimg.com
--Anonymous
replies 337Feb 2, 2018 5:06 PM +00:00

Emanuel Moire, French singer/actor

--Anonymous
replies 338Feb 3, 2018 3:11 PM +00:00

Ralph Reed

--Anonymous
replies 339Feb 7, 2018 6:14 AM +00:00

Ryan McPartlin

--Anonymous
replies 340Feb 8, 2018 6:25 PM +00:00

Phillip McCracken

--Anonymous
replies 341Feb 8, 2018 7:03 PM +00:00

Hugh Dancy

--Anonymous
replies 342Feb 9, 2018 2:10 PM +00:00

Travis Fimmel

--Anonymous
replies 343Feb 9, 2018 8:51 PM +00:00

Matt Barr

--Anonymous
replies 344Feb 11, 2018 6:32 AM +00:00

Jeremy Brett

--Anonymous
replies 345Feb 14, 2018 6:06 AM +00:00

Model Jordan Barrett

--Anonymous
replies 346Feb 16, 2018 6:02 AM +00:00

Good one, R346.

--Anonymous
replies 347Feb 16, 2018 7:02 AM +00:00

Jason Morgan -- model.

--Anonymous
replies 348Feb 17, 2018 11:35 AM +00:00

Lulo

1,799 Likes, 40 Comments - ??Lulo?? (@itslulo) on Instagram: “???????? Hi! Meet my new best friends Maci & Squirt! ^.< thank u so much @animaltracksinc for having me…”
Instagram
--Anonymous
replies 349Feb 19, 2018 7:45 PM +00:00

John Ritter always looked good in drag

--Anonymous
replies 350Feb 19, 2018 7:59 PM +00:00

R349 Straight guys consider Lulo to be a trap.

--Anonymous
replies 351Feb 22, 2018 5:16 AM +00:00

David Hogg

--Anonymous
replies 352Mar 31, 2018 12:14 PM +00:00

Adam Brody

--Anonymous
replies 353Apr 15, 2018 2:30 PM +00:00

Ann Coulter

--Anonymous
replies 354Apr 15, 2018 2:59 PM +00:00

Bobby Flay

--Anonymous
replies 355Apr 16, 2018 4:05 AM +00:00

Travois Reinking

--Anonymous
replies 356Apr 24, 2018 11:44 AM +00:00

Dr. Ronny Jackson

--Anonymous
replies 357Apr 26, 2018 1:15 PM +00:00

a woman

--Anonymous
replies 358Apr 26, 2018 1:20 PM +00:00

A young Robert Sean Leonard

--Anonymous
replies 359May 29, 2018 8:06 PM +00:00

Jules Horn, male model.

--Anonymous
replies 360Jun 5, 2018 9:03 AM +00:00