My boyfriend, the cross-dresser

As a member of the Dan Savage generation, I never ruled anything out. But we'd never gone out in public, until now

Published November 3, 2014 1:00AM (EST)

  (<a href=''>SensorSpot</a> via <a href=''>iStock</a>)
(SensorSpot via iStock)

We arrived in Atlantic City one of the first Fridays of summer.

I pulled out the two dresses I'd brought with me — both of them sluttier than anything I'd wear at home, but AC seemed to call for it — and my boyfriend started unpacking his bags. His dress shoes and button-downs came out first but were quickly discarded. They were only there to keep the rest of the bag's contents out of view. He's a paranoid fucker; nobody would be going near that suitcase. But I didn't say anything about it.

Then he got to the reason we were here. Corsets, padded briefs and a pair of massive fake breasts  followed by a mess of black fabrics that untangled into three separate dresses. The stripper heels stayed in their box (which I carried up to the hotel room after being asked, "The box is hot pink, babe. Can you please hold it for now?") as did a carefully wrapped long, brunet wig.

I never pictured myself dating a cross-dresser, but as a member of the Dan Savage generation I also never ruled anything out. Before this guy came along I thought I was pretty kinky. I'd been asking boyfriends to tie me up, hold me down and hit me harder since high school, and my tastes had escalated at a pretty steady pace.

But when one of my best friends revealed to me that he had a hidden stash of makeup and panties, I was intrigued. When we started dating months later, I knew I wanted to see it for myself. But he wasn't ready. So when the opportunity to stay in a free hotel room came up, I talked him into it.

"We don't have to do it tonight," I told him. "We could save it for tomorrow and take it easy today.

"No way,” he said. “If we don't do it today, I'll lose my nerve. Now go into the other room. I don't want you to watch me getting dressed."

Let me get this out of the way first — my boyfriend isn't "girly." No, he doesn't watch sports and he sometimes spends more time on his hair than I do, but he's joked that he's like a cartoon character in that he wears the same outfit (jeans and a black T-shirt) pretty much every single day. He drinks beer and whiskey, doesn't dance when we go out, plays far too many video games, and all-in-all is a dude's dude. Which is why I was pretty surprised one night when, after leaving our friends at a bar to go smoke a joint on an East Village stoop, he pulled out his phone to show me pictures of a strangely familiar looking girl pouting at the cellphone's camera.

"That's me," he said, his other hand shaking as he clutched a cigarette. "Do you think I'm weird?"

"Not at all," I told him, and gave him a hug. "And honestly? You look good."

And he looked just as good when he came out of hotel suite's bedroom, dressed in thick black panties with inserts that filled out his hips and a corset that drew his waist in. The dress he'd settled on was one of mine. It had sheer sleeves that came down to his forearms, hiding both his bra straps and his shoulders, which he called one of the biggest "giveaways."

I raised an eyebrow. "Your boobs are bigger than mine.”

"Fuck yeah they are," he said, grinning broadly. "Go big or go home."

I helped him apply his makeup, paying extra attention to the foundation to mask the faint trace of stubble left from shaving that morning. He gravitated toward bright pink lip glosses and dark shades of eyeshadow, things I found too stripperish for my own regular use. As he fussed over his hair in the mirror I  put on my own clothes, a skin-tight black slip dress and knee-high leather boots that I lovingly refer to as my hooker shoes. I tried to fish for a couple of compliments but he was too nervous to pay attention. It was fine. Tonight wasn't about me.

When we finally left the hotel room he looked terrified. I held his hand as we walked through the lobby, only letting go to flag down a taxi.

"Where are you ladies headed tonight," the driver asked without any trace of a smirk. He grinned at me in the bac kseat. "Ladies!!" he mouthed, finally getting as excited as I was. When we got out of the car and stepped onto the two-story escalator leading up to the casino's main floor, we heard a wolf whistle come from above.

A group of frat boys was coming down the opposite side, and after a couple of lewd comments one of them yelled, "Wait, that one's a dude!" His face fell, and I could see him brace himself for an entire evening of those kinds of comments. "Just ignore them and kiss me," I said. He did, and relaxed. "Shit," I said a minute later, as I thought of the perfect comeback. "I should have said, 'Don't be mad that my girlfriend is hotter than yours.'"

He laughed, before grabbing my hand and dragging me toward the closest bar. "I'm gonna need a drink in my hand all fucking night, OK?"

We started the evening at an oval-shaped bar surrounded by poker, blackjack and roulette tables. I took the lead, flagging down the bartender and ordering for both of us while finding him an empty seat. He wasn’t quite used to his 6-inch shoes yet. As we sat there, two girls walked over and complimented his dress, asking where he got it. His eyes turned up to me — it was mine, after all — and after I answered they said, “You look great!” before walking away. “I’ll bet you they just wanted to come over and talk to the cross-dresser,” he said. “Stop it,” I replied. “I get asked questions about that dress almost every time I wear it,” and I kissed him again.

This went on for a little while as he polished off two glasses of neat scotch and I nursed my whiskey and ginger ale. He’d think someone was looking at us strangely, I’d kiss him. The waitress did a double take when he ordered a second round, I’d kiss him. Finally, when we got up to leave, a man who had been circling the area said, “Are you ladies all done teasing the rest of us?” We looked at each other, smiled awkwardly, and got out of there. “That may have been the first time I was sexually harassed,” he said, smiling.

From there we went to another of the casino’s bars, and started talking about deep dark secrets we’d hardly shared with anyone. Something about him being dressed up and out in the world made us both more vulnerable and more able to be honest and open with each other about things we’d never discussed before. I revealed past experiences nobody knew about, toes dipped into worlds I’d kept from even my closest girlfriends, while he shared even more kinks he wanted to try. “This,” he said, indicating the dress, hair and heels, “is kind of the tip of the iceberg.”

This dimly lit, drunken conversation bled into the months following our weekend away, and opened doors in our relationship neither of us expected. We bought toys, planned vacations, and dirty-talked our way through how to make realities of scenes that both of us had accepted would always just be fantasies. We both knew that there were people out there who shared our kinks, but had only been brave enough to explore them anonymously over the Internet. For both of us to find out that our partner was not only willing to try these things, but excited to push boundaries and break new ground? It was nothing less than a revelation.

A little while later we went past the bar to a burlesque-themed nightclub, where we danced to Top 40 in between "Coyote Ugly"-esque dance routines backed by a hair metal cover band. He bounced on his heels, shaking his giant fake tits, as I gave him subtle tips on how to dance girlier. (“More hips, less shoulders.”) We made out furiously on the dance floor, ignoring everyone around us, and then I touched up his lip gloss.

The evening went on and we both got drunker, so a trip to the bathroom became necessary. This had been much-discussed before we left the hotel. “There’s no way I’ll be able to go into the men’s room like this,” he said. “And I can’t go into the ladies’ alone.” So off we went, hand in hand until we broke off into separate stalls. I was at the mirror making small talk with another drunken gambler when he came out, and when we saw him we both started laughing.

“Honey,” the stranger called out as he sauntered toward us without a care in the world, “you’ve got a little problem with your dress.” He looked down to see the front of his skirt tucked into the tops of his crochet-patterned tights, and started giggling along with us. He straightened himself out, and we gave our makeup another once-over before heading back into the casino to get another drink.

Eventually our feet were getting tired, so we sat down at some slot machines to take a break. He started gushing about how surprised he was the night had gone by without a hitch, that he had been expecting some sort of altercation that never came. But all of a sudden his voice cracked and he stopped, turning his long, mascaraed lashes up toward the bright flashing lights on the ceiling as his eyes filled with tears.

“I never thought I would ever be able to be this honest and open about who I am with anyone,” he said. “Let alone actually go this far with it and have them be into it too.”

“Of course you can be honest with me,” I told him. “I want you to be able to tell me anything, we can explore this stuff together.” He smiled and took hold of my hand, taking care to turn his bitten-to-the-quick fingernails underneath my palm and out of view. “Thank you for indulging me,” he started to say self-deprecatingly, but I interrupted.

“That’s not it at all,” I said. “I’m not doing this for you, I’m doing it with you.” He seemed startled by my distinction. “I am touched and honored that you felt comfortable enough to get dressed up in front of me at all, let alone come out in the real world. I’ve never had the chance to do something like this for anybody, and I’m not going to let you feel ashamed about who you are and what you want.”

We sat for a few more minutes as I told him about a previous relationship, asking over and over for what I wanted, things I needed, only to be shot down and dismissed. He opened up about getting bad reactions when people found out about his kinks in the past, stories I’d heard before but never when he was feeling this raw. I held his hand and stroked the side of his face, catching tears under his eyes before they fell.

Then, as abruptly as this heart-to-heart started, it stopped. He stood up, straightened his clothes, and wiped his cheeks, being careful not to smudge anything. “Let’s get out of here, I think we’ve had enough to drink.”

And just like that, the conversational part of the night was over. We’d said what needed to be said. Our truths had been told, our hidden secrets revealed, and neither of us wanted to unpack the evening any further. It never mattered that he was wearing my dress -- this was still my boyfriend, and when the serious talk was finished, so was he.

By Sarah Birch

Sarah Birch is the pen name of a writer who wants to protect the privacy of her boyfriend.

MORE FROM Sarah Birch

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