Cynthia's Visit (A Transwoman & Crossdresser Story)

Cynthia’s Visit

Waiting anxiously at the tube station entrance, I watch every face that walks past me. See, I’m picking up my friend Cynthia, who has finally agreed to come to visit all the way from Illinois!

We’ve been talking over the internet now for just over a year and this will be the first time the two of us have met in person.

I really hope it isn't awkward!

I do already know she’s going to be a…little annoyed at me.

She knows me as Katie, my female self. Right now, I’m not dressed that way at all! It’s such a busy underground station, I chickened out.

That’s when I see her!

Cynthia is an incredibly confident and fiery redhead. I can see she’s wearing black wedge heels, black leggings, and a lovely maroon dress.

I was stunned at how good she looked. Her transition must be going really well! She also looks like she’s dropped a dress size! Lucky thing

Feeling a slight hint of envy, I throw my hand up into the hair and call out for her.

“Cynthia!” I wail, with people walking past giving me dirty looks.

Catching her attention, she gives me the biggest smile and rushes over. Pulling her bags behind her, they make an awful racket as the wheels spin to keep up

“Katie!” she booms, pushing through a crowd of people.

As my female name is shouted across the entrance of the station, I feel my face go red. I act casual, trying to pretend she wasn’t talking to me.

“Hello!” Cynthia puffs, reaching me. “We….meet at last!”

“Hiya,” I awkwardly reply, knowing she’s already judging me for my drab male appearance.

Letting go of her bag, she throws her arms out and grabs me close.

“Where’s Kaite?” Cynthia asks, squeezing me tight. “I’m sad you haven’t let her out today.”

Letting me go, I rub at my face, and look anywhere but into her eyes.

“Sorry,” I respond, giving her a quick smile. “I….just didn’t have time today.”

Placing a hand onto my side, Cynthia nods.

“It’s ok Katie,” she says, adjusting her dress by pulling it down. “Don’t get me wrong, you are a handsome man, but I’d have much preferred to have met Katie.

“Shhh,” I respond a little frustrated. “People are looking at us. You keep calling me Katie when I’m dressed like a man!”

Looking around at the people scurrying past us, Cynthia looks at me unimpressed.

“Shall we…..go to your apartment then?” Cynthia then says, pointing in all directions. “Is It far?”

“Probably for the best,” I say, holding out a hand to help with her baggage. “It’s not far and it’s this way.”

Walking five minutes down the road, I could tell Cynthia was excited about being here. She was constantly asking questions about the area.

She had a great time pointing out how smaller everything seemed here.

We eventually reach my flat, and we stand at the entrance.

“You….live here…?” She asks, pointing at the front door which is down a small staircase. “In someone's basement?”

“It’s not a basement,” I groan, opening the door and letting her into my pokey little world.

“Make yourself at home!” I say, showing her the kitchen living area.

She spends a few seconds looking around the place. Especially interested in my bedroom.

“So…..,” she says, looking me up and down. “I saw a pub on the way here and I really want to go.”

“Okay,” I say with a smile. “We can go now if you want.”

“No….I want to go with Katie,” she continues, touching at my baggy male clothing.

“I….I…..,” I mutter, stumbling on my words. “I….don’t know if I’m ready for that!”

“Baloney!” Cynthia laughs. “I’ve seen those legs. Go put on a dress and we will head over.”

“I dunno,” I reply, rubbing my arm. “It’s ok for you. You’ve got the lovely long hair, the budding bosom, and the confidence to be your true self. I.. don’t have that.”

“Girl!” she laughs, snapping her fingers. “I’m confident because I’m finally happy that my appearance matches who I am on the inside. Don’t you want to feel like that too?”

“I do,” I answer, letting my head sag as I answer. “It’s just….”

“Just nothing,” Cynthia giggles, turning back to head inside my room. “I know you’ve got some cute outfits in here. Let's just play dress-up together and take it one step at a time!”

Not giving me a chance, she pulls out the box in the bottom of my cupboard and throws it on the bed.

“Crossdressers…,” she smiles, opening the box and pulling out some of my feminine underwear. “We’re all so similar. I used to hide my outfits in a box like this too before I started my transition!”

Blushing, I watch her pull out a pair of very lacey red knickers.

“Oh…,” she grins, holding them up. “For date night..?”

I don’t answer, I just blush and look away.

“So….that date the other night, didn’t go well then?” she questions, throwing the underwear in the box.

“Oh…..err…..,” I say, shifting nervously. “I….just couldn’t bring myself to leave dressed like I was.”

“Dang!” Cynthia gripes, looking at me disappointed. “I saw the pictures you shared that night, you looked a million bucks in that little black dress! Now you’re telling me you never went!?”

“Don’t,” I moan giving her a sour look. “I felt so bad I stood them up. I just didn’t dare to go out dressed like a woman.”

“Ah yeah….I understand,” Cynthia says, pulling out another pair of naughty underwear. “I’m lucky to have had Esme supporting me in the early days.”

“Oh yeah…!” I chirp. “How is she?”

“Super jealous,” Cynthia grins. “She’s been wanting to come to Europe for years! She was gutted when she found out she couldn’t come too.”

Looking extremely excited, Cynthia then pulls out the little black dress I wore the other night.

“Hot dog!” she cries, holding out to me. “I know it’s not the same as date night…., but…. will you wear this for girl's night…..?”

“I guess I can,” I answered giving her a dubious look. “Depends on what you are planning for us to do on a girl's night?”

“Katie,” Cynthia grins, wagging a single finger. “Stop worrying. Just know that getting all dolled up is the first step.”

Reaching to grab the dress, I lay it down neatly on my bed.

“It’s guna take me a hot minute to get all fem’d up,” I tell her. “What are you going to do in the meantime?”

“Well…..,” she says, clapping her hands together. “I brought something from home and as the guest in your place, I thought I’d make you dinner!?”

“Oh sweet!” I answer, sifting through my feminine clothing, looking for my forms.

“So next time I see you,” Cynthia points, smirking. “You’re going to be so very pretty…., you’ll be melting hearts on looks alone!”

“I doubt it,” I quip, taking off my t-shirt.

Following my usual routine, I have a shower and a close shave all over. Once that’s done, I moisturize my legs and face.

Having done that, I select a matching pair of underwear from my box and fill the bra with my forms. Slipping on my hip and bum shapewear, I grab my corset and do it uptight.

Wearing all this extra stuff was a little uncomfortable, especially the hip forms. Makes it a lot more of a challenge to wee.

It’s all worth it. With my waist compressed and my chest and backside looking more voluptuous, it helped me feel more like Katie…. and less like boring old vanilla me.

Sitting in front of the mirror for thirty minutes desperately trying to do my makeup to perfection, did make me feel a little bad for Cynthia. She’s a guest and I’m staring at myself redoing my eyeliner again and again.

After agonizing and still not getting it perfect, I fit my brunette wig on and brush it straight. I’d selected my favorite wig. I called it the Zoe Deschanel!

Pleased with my hair, I reach into my box and pull some black pantyhose out and a pair of black heels.

Easing my legs into the pantyhose, I’m soon ready to zip myself into my little black dress. It was a little creased from the other night, but being so tight to my body it didn’t seem to matter.

The poor dress really had to work to hold my male form in!

Slipping my feet into my heels next, I take a few nervous steps towards the living room where Cynthia is cooking.

As I stand at my doorway, I can smell the sweet, savory flavors wafting around my flat.

“W-what….do you think…?” I ask her, presenting myself.

Standing at the oven in my kitchen, she turns and her face lights up.

“Sweet honey biscuits,” she yells, clapping her free hand against the wooden spoon she holds in the other.

“Do I look ok…?” I query, anxiously trying to pull my dress down to cover more of my legs.

“I told you!” Cynthia boom. “You look a million bucks girl!”

Concentrating on my walking, shaking my hips, and stepping carefully in my heels, I’m curious about what she’s cooking.

“Mac and Cheese…?” I ask, looking into the pot.

“You betcha,” she cheerfully answers, stirring it with the wooden spoon.

“Is it ready?” I ask, holding onto my forms as I lean over to look.

Instantly telling me to sit, Cynthia dishes it out onto a plate. Giving me a single portion, she doesn’t do herself a plate. I give her a curious look as she sneaks off into my room.

“Katie….,” she giggles, knowing I’ve seen her trying to slip away. “I’m going to slip into something more fitting for our girl's night!”

“O…kay,” I reply, cautiously trying to eat without smearing my lipstick.

With her in the other room, I take bite after bite until I finish my plate. Hearing her crash about, I wonder what she’s up to.

Moments later, Cynthia busts into the room, throwing her arms up in delight.

“Well!?” she exclaims, presenting herself to me. “Do I look like a woman who means business?”

“Wow,” I answer, looking at her in a new light. She’d changed her outfit completely!

Her curly red hair was now arrow straight. Gone were her wedge heels, replaced by a bright red stiletto’s. Her dress was now also bright red, clinging to her newly forming feminine curves.

“It’s my girlfriend's lucky red dress!” Cynthia giggles, adjusting the fit slightly. “Do I wear it well?”

“You do,” I answer, looking slightly worried. “Is she ok with you borrowing that?”

“She doesn’t wear it anymore,” Cynthia flippant replies. “Would be a shame to waste the luck….don’t ya think…?”

“I see where you going with this. You wanna go out tonight……..don’t you?” I ask with my heart beating like crazy. “

“Sure do Hunny bun,” Cynthia answers, giving me a wink. “The people of London would be missing out if we didn’t!”