Chapter 2

Wonderland by Emily

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I checked the Wonderland app to see what Ashley likes to wear to work. The Dress code of her office is business casual.  Ashley wears a variation of blouses and pencil skirts and slacks.  

I opened her closet to reveal a whole bunch of outfits I wanted to try. Dresses, blouses, skirts.  Unfortunately I only have 24 hours to do this.

I pulled out a pale blue blouse and a patterned pencil skirt.  I remembered the alarm saying it was going to be a warm day.  No tights.  I’m going to bare my legs like I’ve always wanted to do.

I turned on the shower and started removing the clothes that were on this body.  Under the t-shirt was no bra.  Ashley had what I would call perfect breasts.  Not too much, not too little.  Just enough.  Very cute pink areolas.  I took off the shorts to reveal pink polka dot panties. I slide those off too. Her hair down below was shaped into a heart.  Cute.

I felt my legs. A little prickly. I was going to need to shave them.

I walked into the shower and felt the hot water cascade off my head and shoulders.  This simulation is amazing.  It feels like the real thing. Granted my real body is currently submerged in a tank, yet I can feel everything in this environment.

I looked at Ashley’s selection of shampoos and conditioners and went to work washing my hair.  Next was the razor and shaving cream.  What nobody knows is that I‘ve actually been shaving my legs for 2 years, so this was easy.  Ashley’s legs were shorter and thinner than mine and her hair wasn’t nearly as thick so I was done quicker than usual.

I got out of the shower and dried off with a towel.  I wrapped my hair up in a towel and I draped a second towel around my chest like I’ve always wanted to do.

I found a matching  bra and panty set, put them on, and admired myself in the mirror for a few minutes.

I started brushing and blow drying my hair.  Looking at Ashley’s pictures shows she keeps her hair straight with a center part.  So that’s simple enough.

After my hair was dry, I put the blouse and skirt on and admired my reflection.  I had attempted to cross dress a few years back when I had a female roommate.  She never knew that I snuck into her room when she was out with her boyfriend.   I always looked like a dude in a dress.  But now - Ashley is hot.

Stupid Eric.  He chose some goofy celebrity to spend a day as.  I chose a hot woman and I am having zero regrets.

I looked at Ashley’s The Hub profile pictures and attempted to mimic her makeup.  My attempt wasn’t perfect but I think it was close enough.  The Wonderland app told me that her everyday look included eye shadow, mascara, and lip gloss.

Shoes.  I saw Ashley’s shoe rack.  Wow.  A lot of shoes.  Which ones will be good for work?  I saw a pair of black flats that looked like they were worn every day.  Ashley likely wears those to work.  I saw a pair of black heels.  But I’m going to wear those heels today.

I put the heels on and practiced walking around the room with them.  This is not the first time I’ve worn heels, but it has been a while.

I found a purse at the front door.  I examined the contents.  A wallet, keys, a brush, and chapstick.  I opened the wallet to reveal credit cards, cash, and a driver's license.  The attention to detail in this sim is amazing.

I dropped my phone into the purse and walked out the front door.  Outside was a neighborhood of rowhomes.  I locked the door behind me.

I pulled the phone and app out and let it lead me to the subway.

I found Ashley’s subway pass tucked into the back of her work badge.  I walked into the station and caught the next train heading in my directions.  4 stops later I got off the train and walked out of the station.  I was in the middle of a bustling city with skyscrapers lining the street.

I followed the app to Ashley’s office.

Ashley had some kind of analyst job and I spent the morning hours writing and compiling reports.  My mind was mostly distracted by being in a woman’s body.  Every sense was heightened.  I could feel my bare thighs rub against each other.  I could feel my breasts bounce when I walked.  I noticed each and every male walk by, look at me and smile.

The Wonderland app told me every colleague's name, so I managed to strike up conversation with everyone who the app told me I was friendly with.

Around lunch time a delivery came.  It was a bouquet of roses.  There was a message. “Happy Valentine's Day, Ash! Looking forward to our date tonight.  I’ll meet you outside Union Station. - Bill 

Oh shit.  Ashley has a Valentine's day date.  I didn’t know that when I picked her.  Now I have to go on a date with a guy.  I’m not gay and very much into women.  I’m sure I could cancel.  Bill wouldn’t mind right?”

I looked at my personal calendar in The Hub.  Sure enough, “VDay with Bill <3” was listed for today.  My feedback for Wonderland will include not giving me my avatar’s calendar for that day before selecting them.  Or maybe that was part of the allure.  Being surprised like this.

My phone vibrated.  It was the The Hub app.  Bill messaged me.  “Hey babe.  I just sent you flowers. I Love you!”

I started typing “I’m going to have to cancel” but didn’t hit send.  I've been given a unique opportunity here.  Sure Bill is a guy, but I’m currently a very attractive woman.  When in Rome, right?  I erased my message and instead typed back “Can’t wait.  Love you too!”  I hit send.  

I guess I’m going to have evening plans now. This gives me an opportunity to find and try a sexy outfit.

* * *

The rest of Ashley’s workday was rather quiet. It was a huge change from my busy work day where I would end up working late often.  I closed up my computer, grabbed my purse and headed back home through the subway.

When I got home I picked out a little red dress and matching red heels.  I also found black lingerie in the underwear drawer.  I took off my work clothes and slipped into the lacy underwear.  I danced sexily in front of the dresser mirror.

“Hub” I called to the phone.  “What’s tonight’s temperature?”

“This evening will be 70 degrees fahrenheit with a low of 62” the phone replied.

I could go bare leg again, but I really wanted to try out pantyhose.  I found a cute pair that had tiny hearts all over them. Perfect for tonight’s date.

I pulled the hose up each leg, smoothing it out.  God I felt so sexy.

I did a time check, then threw on the red dress.  I touched up my makeup and brushed my hair, grabbed my purse and headed back into the city.

I met Bill at Union Station like he requested.

Bill was taller than me - or rather taller than Ashley.  I’d say he was my height, but had a more athletic build than I did.  He was dressed in a suit and tie.

“Hey beautiful,” he said with a smile.  

He leaned in, and I decided to go with the flow as our lips touched. 

Kissing a man.  It was OK I suppose.  I was already turned on being in this body, but kissing him definitely turned me on more.  I felt his hands on my waist and it reminded me of how hot this body was that I kissed him more

He broke this kiss and chucked.  “Dinner first?”

“Let’s,” I said with a smile.

Bill led me two city blocks to a fancy restaurant that had a line of couples waiting outside the doors.  Bill walked us past the line.  We had a reservation and were seated within 2 minutes.

Bill ordered us drinks.  I ordered a special Valentine's Day cocktail that tasted like various rums.  I ordered a lobster tail.  Hey, if he’s paying, right?

The conversation was pleasant.  We talked about our day.  Apparently we’ve been dating for 6 months and met one day on the subway.  I could tell he was eager to get dinner over with.  It just occurred to me what I may have gotten myself into.  Ashley and Bill are likely sexually active.  Bill is going to expect sex tonight after all of this wining and dining.

I could feel my adrenaline kick in.  Just like all of the other crazy stuff Eric has made me too.  This might be the craziest.

Bill paid for our dinner.  We casually walked back to the subway holding hands.  We stopped at the station entrance.

The silence lingered there for a moment before he said.  “Your place or mine?”

I didn’t know what to say. Should I say “Not tonight?”  Instead I wanted more excitement and said.  “Mine.”

I led Bill back to Ashley’s place.  The moment we walked through the door, Bill threw himself at me.  I didn’t resist.  Instead I lost myself in the moment and gave myself to him freely.

Off came my red dress and heels.  Off came his suit, his tie.  I was lying in my bed in my sexy lace underwear.  We kissed. I could feel his hands on my bare skin.  I could feel his dick poking into my thigh through his boxers.  He cupped my breasts and I closed my eyes and smiled.  Off came my lace bra.  Bill started playing with my nipples.  First with his fingers.  Then his tongue.  I let out a moan.  I wanted more.

I ran my hand down to my groin.  I was wet.  I rubbed my clit for a few minutes while he was kissing me and attended to my breasts.  

I could tell he was waiting for something.  He was a gentleman and was waiting for the go ahead.

I looked into his eyes and told him “Take me.”

And he did.  Off came my lacy underwear. Off came his boxers. Before I knew it, I felt his member slide into my wet pussy.  

Oh my god this is amazing.  How is this possible? I’m a man in a simulation and I can feel everything.  I don’t have a vagina yet I can feel him thrusting into me.  

I came about 5 times.

Bill fell asleep spooning me. 

I was coming off an amazing high.  My 24 hours were just about up.  I kept having the same recurring thought.  I’m going to need to do this again.

* * *

The alarm from yesterday went off.  “Good Morning.  It’s 7 AM on Tuesday February 15th.  The current temperature is 65 degrees fahrenheit.  Today’s top new stores are..” 

I reached over and dismissed the alarm.  I looked to my side and Bill snoring next to me.  I expected to wake up in the tank.  What?  It’s been over 24 hours.  I shouldn’t still be in the simulation.

I jumped out of bed in a panic.  I searched for the Wonderland App.  It was gone.



Hi, I'm Emily and I'm writing Gender Transformation Fiction! This site is a place for me to keep all of my stories in one place. I'm also a software developer in the daytime, so this site will also be a proving ground of cool new features that pop into my head. Feel free to message me on Twitter or at my Discord Server! You can also find me on and

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OK, Ryan knows what Eric told him he was going to do - be someone famous and have a party - that doesn't mean he actually DID that. Eric could really be Bill and setting up Ryan for some kind of trap. So what is actually going on? Could Ashley be pregnant? Or just stuck in the simulation? And why is the Wonderland App gone? Great writing, and a great place to end the chapter. BTW, there is a word 'too' in this chapter that should be a 'do'. Good luck.

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