Maybe it's because Christian Siriano is shouting "hot tranny mess" from every rooftop in New York, or perhaps we've been looking at more cross-dressers than usual with Heatherette's new M.A.C line and all, but this whole men-as-women thing seems a hot topic as of late. How else to explain the London Times essay by a straight cross-dresser who's struggling with how to reveal his affinity for ladieswear to his girlfriend of two years? They're about to move into an apartment they've bought together, and he's afraid she'll discover his habit, which began when he started sneaking into his sister's room at 15 to try on her clothes:
I'd put on her high heels and totter around the bedroom, catching glimpses of myself in the mirror. I particularly enjoyed the miniskirts. This gave me quite a sexual thrill … Then I graduated to her underwear. I loved squeezing into her knickers, especially the thongs. Also I would put on her bras; black was best. Sometimes I'd strut around the bedroom in bra, thong and high heels. I was always terrified that she would come in, but this added to the excitement.
Now 23, he's acquired his own stash of women's "gear," which will be difficult to hide in his new living situation. He's straight as an arrow and would like to come clean to his girlfriend but worries, naturally, she won't be so cool with it. He adds:
I don't want to change because I get so much pleasure out of cross-dressing. It complements the sex I have with Samantha, which I don't want to give up either. But nor do I want to keep a secret from the person I love. I'd hate to think that she had secrets from me.
…I'm also now feeling the urge to “dress up” away from home. I'd love to go out in women's clothes and I'm frightened that one day I'll give in to this desire.
Even in these open-minded times, a man in a woman's clothes brings out the judgment monster in a lot of people, especially in a girl who's unknowingly dating one. This will not go well.
Most Viewed Stories
Rob Kardashian and Blac Chyna Reportedly Broke Up
Donald Trump Spent the Morning After the Debate Fat-Shaming Miss Universe, Again
It’s Finally Possible to Understand What Happened to Amanda Knox
Hillary Clinton’s Sickest Debate Burns
Ask a Boss: My Co-worker Wants Everyone to Call Her Boyfriend Her ‘Master’!
2009 Called — It Wants Its Vogue-Versus-Bloggers Fight Back.
22 Intimate Lost Photos of Marilyn Monroe
Former Miss Universe Becomes U.S. Citizen So She Can Vote Against Trump
Area Woman Interrupted by Man 25 Times in 26 Minutes
Our Scowling Hero Breaks a Smile
From Our Partners
powered by PubExchange
Latest News from The CutChelsea Clinton Says She Didn’t Initially Know Her Mom Had Pneumonia Because She Was Trying to Power Through It
She says she found out when her mom showed up at her apartment.Men Who Protested Ryan Lochte’s Presence on Dancing With the Stars Are Charged With Misdemeanors
Two men were charged with two counts of misdemeanors on Monday.Serena Williams Refuses to ‘Stay Silent’ About Racial Inequality
“It’s not how far we have come but how much further still we have to go.”Young Girl Calls for End to Police Brutality in Heartbreaking Speech
It’s a devastating plea.The Y Has Returned in a Big Way to YSL
This is what Saint Laurent looks like post-Hedi.The Most Dramatic Backstage Photos You’ll See All Fashion Month
Preview the book Landon Nordeman: Out of Fashion.Even 100 Years Ago, People Were Worried About Technology Ruining Relationships
An old cartoon echoes some very modern anxieties.This Lipstick Was Designed by a Woman Who Can See 100 Million Colors
Maureen Seberg can see so many more colors than you.Brad Pitt Skipping Premiere to Focus on ‘Family Situation’
The actor may be gearing up to tell his side of the story in the tabloids this week.Please Help Wesley Snipes Find His Leather Jacket
He will be cold without it.
It signals how the candidates feel about women.YogaToes Cured My Lifelong Fear of Bunions
The stretch feels like a backbend—but for your feet.Amy Schumer Just Broke a Major Milestone for Women in Comedy
She’s the first woman to land on Forbes’s list of the highest-paid comedians.The Very Uncomfortable Experience of Rewatching Election in 2016
An ambitious woman and the angry men who want to stop her.Ivanka Trump Is Great for Women, Says Man Married to Ivanka Trump
Ivanka Trump is the perfect person to handle “women’s issues,” according to her husband.World’s First 3-Parent Baby Is a Healthy Boy
He was born in Mexico to Jordanian parents.Nation Recovers From Post-Debate Hangover With Mary J. Blige and Hillary Clinton Memes
“What will you do to fix the national epidemic of hateration in this dancerie?”The Hottest Party of the Year Is This 6-Year-Old’s Drake-Themed Birthday Party
It has everything: an OVO cake, Drake balloons, fake money.See Haute Couture’s Most Romantic Looks
Intricate pieces, out for a stroll around Paris.Rob Kardashian and Blac Chyna Reportedly Broke Up
TMZ reports that all the baby-shower drama stems from a breakup.