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Stories

11 Stories About Cross-Dressing

J. Edgar Hoover made cross-dressing big in the States, and now everybody’s doing it. Eleven stories on the ordinary lives of people in different clothing.

1

Caleb was standing in the kitchen, wearing a yellow organdy A-line shift with black velvet piping around the neck and hem, when he heard his wife’s key turning in the lock. He felt his panic rise as he watched the doorknob slowly turn. She wasn’t supposed to be home for another hour, at least. She was never home this early, ever, but that didn’t matter now. It was too late. There was nowhere to hide. He would never be able to undress in time. He would just have to stand there and own up to the situation. He stood by the sink, trembling in his round-toe pumps, as the door slowly opened.

June-May entered the kitchen. She looked up at Caleb and froze, staring at the sight of her husband standing there in a yellow dress.

‘You son of a bitch,’ she said finally.

Caleb raised his hands in a calming motion. ‘Now Junebug, don’t—’

‘You son of a bitch!’ she said, yelling now.

Caleb swiveled slightly, preparing to protect his body from the punches that were surely imminent.

‘I can’t believe you’re doing this to me! I thought we talked about this!’

‘Junebug, just give me a chance to explain, this is all a big misunderstanding.’

‘Did we or did we not already decide that I would wear the yellow dress tonight and you would wear the pink one. Did we or did we not.’

‘Okay. Yes. We did, but I just thought that maybe—’

Caleb’s sentence was cut off as June-May suddenly burst into tears. Caleb shuffled over to put his arm around her. She gasped to catch her breath in between her heaving sobs.

‘I’m sorry,’ she said. ‘It’s just that you’re so pretty and I’m so ugly.’

‘Oh now honey, come on now. That just ain’t true.’

‘Yes it is, you have such a nice petite figure.’

Caleb kissed her forehead. ‘Junie-May you are a vision and everyone knows it. What do you say we forget about the yellow dress. How ‘bout we head back to the closet and pick you out a nice outfit. Maybe that light-blue jumper with the pink bows? How ‘bout that. I never seen you look lovelier than when you wear that light-blue jumper.’

He stood back, waiting for her reaction. Slowly, she nodded, rubbing the tears from her eyes.

He put his arm around her and began walking her towards the bedroom.

 

2

A mother and her young son were clothes-shopping in the Boys’ section of McCloskey’s department store. The mother was hunched over the clothes racks, sliding the hangers down the metal rod. The boy was looking longingly at the girl’s clothes section.

‘Can I please go look at the girl clothes?’ he asked.

‘No,’ his mother said. ‘Jesus. Hell no.’

‘But I want to look at the pretty dresses.’

‘You’re getting a sweater with a football on it and that is final.’

‘But…’

‘FINAL, I said.’

They were silent. Everything went fine for the next 12 years. Then when he was 17 he dropped out of high school, moved out, and his mother never heard from him again.

 

3

Two women in their 20s were driving through downtown Boston, on their way to a party at a friend’s house. They were slightly lost, and happened to drive past Jacque’s, a drag club near Copley. There was a portly man in his late 30s standing outside and smoking a cigarette. He was wearing a wig of black shoulder-length hair, a sparkly silver tank top, a black miniskirt, heels, and fishnets.

A few minutes later, as they were stopped at a red light, one of the women spoke.

‘In theory, I’m all for it. But perhaps there are some men who just should not dress as women,’ she said.

‘At least not outside the privacy of their own homes,’ her friend added.

‘Agreed. Okay turn left at the next intersection I think.’ the first woman replied, looking down at her map.

 

4

Irma was the head of the Human Resources department at Crowell United Mfg. One day she was sitting at her desk reviewing some Excel spreadsheets when there was a knock on her door.

‘Come in,’ she said. Chris from Shipping & Receiving entered.

‘Hi Chris,’ Irma said. ‘Have a seat. What’s up?’

‘Look,’ Chris said, settling into a chair. ‘I know we’ve talked about this before, but I would really like you to reconsider the company’s dress code policy.’

Irma stared at him. It took every ounce of willpower she had to keep from rolling her eyes.

 

5

‘Wait, you’re single again?’ Louise asked. ‘When did that happen?’

‘Couple weeks ago,’ Josie said. ‘It just wasn’t going anywhere, so we just ended it. Mutually, pretty much.’

‘Wow,’ Louise said. ‘You guys seemed so happy the last time we all hung out.’

‘Yeah,’ Josie replied, nodding and wrinkling her nose. ‘It’s too bad it didn’t work out. I miss him sometimes. He was so much fun to go shoe-shopping with.’

 

6

When I was 18, I spent the summer working as an intern at an import/export company. My boss there was an older man named John Charleston, who began every sentence with ‘Hmmm,’ and used the word ‘penultimate’ to mean ‘beyond ultimate.’ (‘Hmmm, Kenneth, this is the penultimate cheesecake. Hmmm? Just try one bite.’)

On my last day there, before I began the fall semester at Dartmouth, he called me into his office. As he was thanking me for all my hard work I noticed a picture on the bookshelf behind his desk. It had obviously been taken decades ago; John was a great deal slimmer and less wrinkled in the photo. He was posed with a group of burly, muscled young men, and they were all wearing dresses and pearl necklaces. John noticed me staring at the picture and turned to look at it.

‘Hmmm, fetching, isn’t it?’ he said. ‘I think I’ve still got that dress tucked away, somewhere.’

Something about the way he looked at the picture while he said that made it the saddest sentence I’d ever heard. I tried to explain it to my boyfriend later, but he didn’t get it, at all.

 

7

Beatrice was frantically searching through her underwear drawer. ‘Goddammit, Harold!’ she screamed. ‘Are you wearing my undies again? I’m late for work!’

Harold shouted back from the bathroom, where he was inserting a Q-tip into his ear. ‘Hey, tough nuts! I told you once I told you a thousand. If you can’t get off your ass and do some laundry around here, then I’ll just wear your underwear when I run out. End of discussion.’

‘Yeah, yeah,’ Beatrice replied. ‘My panties, fine. But what do you need my bras for?’

 

8

Mikey and Tony were Sigma Nu fraternity brothers. One Friday night they were pounding beers at Bart’s, a dive bar located just off-campus, when they spied a very attractive young lady playing a game of pool nearby.

‘Whoa,’ said Tony, putting down his beer. ‘Dude. Check her out.’ He tapped Mikey on the shoulder and pointed to her. She was wearing a very low-cut blouse, and leaning over the pool table to sink the 3-ball in the corner pocket. ‘Holy cripes.’

Mikey put down his beer. ‘Whoa. Yes. Yes indeed, my friend.’

They both stared, watching her prowl around the table in her thigh-high boots as she prepared to take her next shot.

‘Wait,’ Mikey said, after a few moments. ‘Is that a girl? Looks like it might be a dude, kinda.’

Tony squinted his eyes, trying to pierce the bar-room dimness. ‘Hey, you know what? You might be right. What the fuck? You want to go over there?’

‘Not yet. Let’s wait a minute,’ Mikey said. He motioned for the bartender to bring them two more beers. The boys stared in silence as the beers arrived.

‘Well, I’d still do her,’ Tony said, finally.

‘Make no mistake,’ Mikey said, reaching for his beer. ‘I would totally party with him-her-it.’

‘Amen.’

They clinked glasses in agreement and drank deeply. Mikey set down his glass and wiped his mouth.

‘Hey, is the phrase ‘party hardy,’ h-a-r-d-y, or is it ‘party hearty,’ h-e-a-r-t-y?’

‘Party hardy,’ Tony answered, after thinking for a moment. ‘Like the Boys.’

‘Hmmm. I always thought hearty. Like you’re putting your whole heart into the partying.’

Tony nodded, conceding Mikey’s point.

 

9

‘Glamour Couples!™’ is a national association for heterosexual cross-dressing couples. Local chapters hold informal meetings throughout the year, culminating in an annual gathering for all the chapters nationwide. In 2001 it was held in Provo. The year before that it was in Atlantic City. Typically the men are dazzling in their full-length gowns of taffeta or silk, while their wives sport fake mustaches and Armani tuxedos. The meetings offer a great opportunity to meet other married couples with similar interests, with whom they can then exchange beauty secrets and relax in an atmosphere of acceptance.

When couples are introduced at these functions, the husband can almost always be overheard to say something like ‘…And this is my wife, [name]. She wears the pants in the family…Literally!’ This joke never seems to gets old.

 

10

‘Oh how cute! What’s your cat’s name?’

‘Pam.’

‘Nice. And do you always dress her in a tutu?’

‘Him. He’s a he. And yes.’

 

11

During the spring of my freshman year at college I was completely obsessed with a girl in my Early American Lit class. All I knew about her was that her name was Anne and she didn’t much care for the poetry of Philip Freneau. I asked her out a few times after class, but my advances didn’t interest her. After a few rejections I didn’t bother anymore, but unfortunately I couldn’t get her out of my mind so easily.

I followed her, one day after class. I lingered back a bit so I wouldn’t raise suspicions, then traced her steps from a distance as she exited the English building, crossed through the Student Union, and continued out towards Greek Row. As I watched her ascending the steps to Alpha Omicron Pi, carefully noting the way her thighs moved beneath her gray tweed skirt, I suddenly realized that I didn’t want to date her at all: I wanted to be her.

After that, I used our class time to studiously transcribe the details of her wardrobe. The type of barrette. The shade of pantyhose. It was all grist for my mill. I spent hours combing the racks at Dress Barn and Fashion Bug, searching for ensembles that could even remotely do justice to her beauty and stylishness.

I lived for the weekends, when my roommate would leave to visit his girlfriend, who attended a college in another part of the state. I spent hours dressing and undressing, trying different combinations and admiring myself in the mirror. I fantasized that Anne would accidentally barge in to find me dressed this way. Her initial shock would melt away as she realized my dedication to her beauty. I would then take her hand and lead her to my futon, where we would engage in frottage, fully clothed, kissing as a fashion model might kiss her image in the mirror.

One day I bounced a check and I calculated that I had spent in the region of $1500 on clothes in just under a month. At this rate I would never last until summer.

As luck would have it, halfway through the semester I began auditing a linguistics class. There was a girl in the class named Honi. She was a natural beauty who eschewed make-up and favored cotton print dresses and colorful vests. I knew that I could find many outfits similar to hers at the consignment and used clothing stores in town, and my costs would decrease dramatically. I loved her instantly.

biopic

Kevin Fanning has been a TMN Contributing Writer since 2002. He writes about celebrities and relationships and internet culture and can be found online at @kfan. More by Kevin Fanning