Transgender Romance

Thin, chocolate skinned, thirty something. She came out of the apartment next door with a plump cairn terrier on a leash.

My heart pounded as I came up the sidewalk, nervously raising my hand. "Hi."

I thought I saw her smirk beneath her face mask when she waved back. "Hey."

She kept walking.

I opened my mouth to say something, but the words died in my throat. 

If only I had some excuse, some reason to grab her attention!

She turned a corner, walked up the street, not even giving me a second glance.

I sighed, returning to my apartment.

A bubble wrapped package lay on my bed. I nervously turned it over in my hands a moment before ripping it open.

Gray-pink party dress and stockings.

I slipped it on, admiring myself in the mirror. Cute.

Good fit. Didn't try to show off breasts I didn't have. Wouldn't be caught dead wearing it anywhere, but cute.

I blushed. What would the girl with the dog think?

Never mind. She wouldn't know. This is just for in here. I hung it up in my closet for tomorrow.

I didn't sleep that well that night. General insomnia and a swarm of weird looking winged ants around the ceiling light kept me too disturbed to lay down until very late, then when I killed a bunch of the insects, my sleep got further disturbed by the sounds of someone in the apartment upstairs having loud sex. I awoke very groggy the next morning.

Covid made my employer's dress code irrelevant. No webcam sat on my computer tower, so I didn't shave as much, I stopped wearing polo shirts and slacks. A couple times I worked a full shift in my underwear.

So hey, I got a little fancy.

I started small at first, a leotard, a catsuit, a wrestler's singlet that only kind of looked like a bikini. Then I got kilts, and full-on women's clothing. Counting the one I just unwrapped, I owned five dresses.

I kinda think they keep me focused. Maybe a little too focused.

At my nine o' clock work break, I groggily stepped out the front door of my apartment to get some air. I didn't think about how oddly comfortable everything felt until I noticed the girl with the cairn giggling at me.

"Hey! Nice outfit!"

I blushed, my face matching the color of my dress's frilly trim.

My eyes nervously traveled downhill, where a construction crew tore up a section of street. Some guy in a hardhat and orange vest pointed and laughed. "I...lost a bet!"

The girl lowered her mask. "What did you bet on?"

I was never a good liar. It took me a second too long to come up with an answer, and now the kinky haired girl had a grin on her face. "It's okay. We're in the two thousands. No one cares if you're gay anymore."

"But I'm not—!" I began to protest.

"Please." She gestured to my dress, and in a sing-song tone, "Actions speak louder than words!"

I thought she looked Tomboy-ish in her striped shirt and jeans, but nobody ever questioned a thing like that. "Look, I don't—"

"You don't have to make excuses. I don't judge...Any particular reason why you don't embellish your chest?" 

"I think fake boobs look stupid."

"Funny how we've lived next door in the same apartment for so long and never introduced ourselves." Up until this point, the girl had been social distancing, but her dog closed the gap to paw my nylons, and I guess she thought it okay to do the same. "I'm Ashley."

I wiped my sweaty palms on my dress, offered my hand. "Nick."

"Hey, you want to get on TV? I think you'd be perfect for the new contest I saw on Facebook."

I scowled. I knew there had to be a catch! "What, Ru Paul's Drag Race?"

Ashley shook her head. "It's called Red Shift. It's a video game themed reality show."

I paused a moment to consider it. Her dog relieved itself and kicked up leaves to signal he'd finished. The wind blew the dust of concrete and loose topsoil my way. When I heard the beeping of the Caterpillar backing up, I worried I might cause an accident...and temporary blindness.

"Red Shift?...That's a new one." I frowned at my skirt. "Wait, what did you mean when you said I'd be perfect?"

The girl looked a little embarrassed. "They like to put non-traditional couples on the show. Last week they had some Amish people, well, Mennonites. There's been lesbians, obsessed Star Wars fans..."

Now my face really matched my dress. "Look. I'm not gay. I'm not going on TV with some dude!"

Ashley giggled. "That's why it's perfect! We could pretend to be dating - nobody expects a crossdresser to like women!"

I swallowed hard, my pulse pounding at the thought. "We?...Dating?...You and me?"

She nodded. "Just for the show, of course...Are you any good at acting?"

Of course. Still, my eyes widened, realizing I wouldn't need to act at all. "Oh yeah!"

Ashley led me into an apartment on the other side of the building, down the musty carpeted hallway to her door. "You good at video games?"

"Actually, I just beat a Zelda game last night. The lack of sleep is kinda one reason why I walked outside like this..."

The girl glanced downwards. "You don't shave your legs either?"

The warmth that had gone from my cheeks now returned in full force. "It would raise some awkward questions at the pool."

She giggled. "You're really weird."

My heart beat faster when she led me into her bedroom, but our objective hadn't been that kind of rehearsal. Instead she opened a laptop on a bed with covers almost the same color as my dress. "We'll have to submit a two minute audition video. You just basically introduce yourself, and I'll make up the details about our relationship."

Ashley fixed her hair in front of a heart shaped mirror, gestured for me to sit on the bed with her.

She filled up almost a minute talking about herself before throwing an arm around me, throwing the whole social distancing thing out the window. "And this is my boyfriend Nick. He's transgender but he totally digs me."

As shy as I was, I couldn't pass up the opportunity. I slipped my hand around her waist, leaning on her shoulder. I snickered a little when she tensed up.

I didn't have time to say much to the camera, just that I was a customer service rep, that nobody cared what I wore when I worked from home, and I usually didn't dress like this in public.

"What do you think about me?" she prompted.

"You're...very pretty...and, uh...cute."

Yeah, so my shyness didn't make for a compelling boyfriend story. Even that reach-around had been...difficult for me, and her displeased reaction didn't help. And wearing an outfit like mine seriously put my sexuality in to question.

Although my hesitancy made her relax, the girl still didn't seem pleased. She paused the recording.

"I apologize for this," she whispered in my ear. "But we really have to sell it."

When she pushed the red button again, Ashley kissed me full on the mouth.

Okay, well, since she volunteered, I pulled her close and let my lips and tongue show her how much I enjoyed it.

She'd just eaten McDonald's, and she didn't smoke.

Ashley's eyes bugged out. She stopped the video, pulled away really fast. 

"That was great!" she blurted. "Uh, maybe not so good with the talking, but..." She glanced down at my skirt.

I self consciously straightened the fabric, pretending to look elsewhere.

Her cairn climbed up on my lap, stomping my crotch as it licked me in the face, effectively killing my need to straighten my skirt. 

Ashley picked up the mutt, stroking its head. "You've...never...kissed anyone before, have you?"

I shrugged. "Nope!"

She kept staring at me, making me wonder if I should make a move or something. 

Nobody ever educated me on how to do that, though, so I ended up making her chuckle and relax once more, I guess under the impression I wasn't straight after all. "If we get on the show, I think I should be the one doing all the talking. You...don't sound so sure about yourself, but..." She cleared her throat, loosened her collar a little. "Anyways, I'm going to do some clean-up on this video. I just need to get some information from you before you go..."

I filled out my contact information, electronically signed the disclosure things. "You sure you don't want to hang out?"

Ashley only rolled her eyes. "Don't you have work?"

My face flushed when I noticed the time. "Shit!"

"I'll let you know if we get selected."

A few weeks went by. I'm used to losing contests, so I didn't think any more of it. I did my job, and since Ashley kinda used me anyway, I made sure to never wear a dress outdoors again.

Most the time I didn't see her because of work, but once or twice Ashley walked by me with her dog. She didn't ask about the dresses.

One day, though, as I neared the end of a long, tiresome shift, I heard a knock on my door. I put the phone on mute, and thinking it to be maintenance, called out, "Hold on just a second, I'm not decent."

A familiar voice replied, "Are we talking completely indecent, or just you afraid to be seen wearing a skirt?"

I sheepishly opened the door.

Ashley frowned at my humble surroundings. "Do you spend all your money on outfits?"

I reddened. "Maybe?"

"Next time you want clothes, ask me. There might be something that'll fit you...you're not that big."

"I'll try not to take that as an insult. So...what's up?"

She waved a stack of paper at me. "Remember that contest video?"

Swallowing hard, I tried to feign nonchalance. "Uh...kinda?"

Her slender brown hands pulled out a pair of plane tickets. "Got anything going on next week?"

I paled. "Oh God. Seriously?"

Ashley's features narrowed in disappointment. "You don't sound thrilled."

"I...I guess I didn't take it seriously. You're talking about me going on national TV...like this." I tugged on the hem of my skirt to illustrate.

"I dunno...I think it's cute."

A bright pink dress with princess puff sleeves...It was nice. "Um..."

"Did I mention that there's a five hundred thousand dollar cash prize?"

My stomach flip-flopped. I'd already been saying yes in my head, simply because I liked being her pretend boyfriend, now there was money. "I...I got work though."

"Can't you take time off? It's only a week!"

A week that will ruin my life, I thought. 

Still, there was the money, and...the girl. "Okay," I sighed.

"Do me a favor, don't pack any of those casual outfits I've seen you wearing outside. Someone at the airport might have cameras."

"That actually makes me want to pack them more."

She grabbed my hand, a gesture I unconsciously associated with romantic feelings. "Please. Don't. I want to make this look good."

I cringed, but still found myself muttering "Okay."

I returned to work, and thought everything would be fine until (ugh) the flight, but the day before the departure, she knocked on my door, asking about my clothes.

Ashamed of being seen in public as a tranny, I'd chosen a very long black dress to wear to the airport, but she didn't like it, said I should prepare myself for the show. She actually went through my closet, repacking my suitcase for me, and even brought over some of her own old stuff for me to try on.

For the plane, she picked out a dark purple mini dress. When I protested, she argued, "It was hanging in your closet!"

I again showed myself to be unmasculine by modestly changing in private. 

I don't know what it means when a girl refuses to ride with you to the airport. I assumed I was in The Friend Zone, but did that mean she didn't trust me? At any rate, I traveled alone.

June 09, 2021 01:46

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