Dating a crossdresser

Added: Demetrick Tokarz - Date: 11.09.2021 16:45 - Views: 39626 - Clicks: 9309

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? 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. 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. 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 t 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.

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 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.

He grinned at me in the bac kseat. 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! He did, and relaxed. He laughed, before grabbing my hand and dragging me toward the closest bar. 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. As we sat there, two girls walked over and complimented his dress, asking where he got it. This went on for a little while as he polished off two glasses of neat scotch and I nursed my whiskey and ginger ale. 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.

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. 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. 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. We sat for a few more minutes as I told him about a relationship, asking over and over for what I wanted, things I needed, only to be shot down and dismissed. 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. And just like that, the conversational part of the night was over. 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. Sticky Header Night Mode. My boyfriend, the cross-dresser As a member of the Dan Savage generation, I never ruled anything out.

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