Chapter 4 - Bargaining

The Week I Turned Into Erin by Emily

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Synopsis: Aaron desperately tries to take control of his situation.


Content Warning: Chapter has Sexually Explicit Content.

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I woke up scrunched on the couch for the second morning in a row.  My neck and back are killing me.  I opened my eyes and saw Kathy sitting cross-legged on the floor looking at me. Watching me.  Petting Speckles.

“Babe?” I said, still groggy.  “What are you doing?”

“I’m watching you sleep.” she said.  “You looked so cute and peaceful.”


“Yeah, your face is much more feminine.” she said.  “I’ve been watching you breathe.  The way your… breasts... are going up and down.”

I sat up and I looked at my chest and realized I have real breasts now.  No more puffy nipples.  These are the real deal.  I rubbed my eyes and then cupped them.  They felt so soft.  This is crazy.

“May I?” she asked, holding her hands out.

“I… I guess.”  I said.  Kathy’s my girlfriend after all.  She can certainly grope my... breasts.

She cupped my breasts and tested their weight.  “This is amazing.” she said.  “They feel real.  I’d say about a B cup right now.”

I turned red.  I didn’t know what to say.  ”I need help.  I don’t know what I’m doing.  If I’m going to pull this off, I need help.”

“OK,” she said, standing up.  “Let’s get you an outfit for work.”

I got up from the couch.  I realized I was still naked after storming out of our bedroom after sex.  I kept the blanket draped around me.  We both walked to the bedroom.  I was now very aware of the weight of my modest boobs on my chest.

She opened one of her dresser drawers and shoved her hand in the back.  She pulled out a tan bra and looked at the size.  “Try this on.” she said.  “I have some older C cups in the back of my drawers.”

“Wait.” I said. “I want to wear MY clothes.  I was hoping you can help me cover all of this up so I look like myself again.  You know.. Compression bandages, masculine make-up, maybe lifts.”

“Yeah, no.” she said. “I don’t own a professional makeup studio here.  You look like a woman now.  There’s no covering this up.  It will be far easier to dress like one than to try hiding it.”

“What about work?  I’m really trying to regain control of this situation.”

She sighed.  “At some point you have to start telling the truth.  Hopefully they have a gender non descrimation policy.  Or something that protects transgender people.”

“But I’m not trans!”

“Babe.  Seriously.  The more you fight this, the harder it will be.”

“But I still identify as a man!”

“Well the world is going to see a trans-woman. Tomorrow they might see a cis-woman. What are you going to tell them?  That your stupid ass decided to transition into a woman for the money?”

I didn’t want to start an argument, so I let it go.  I don’t want to be a woman.  I don’t want to be trans.  I really just wanted to hide myself.  Hide my body until I can fix this.

She placed the bra on the bed.  She then pulled a women's cut polo shirt out of her closet and laid it next to the bra.  “This should be acceptable for your work uniform.”  Then she laid a pair of leggings next to it.

“I can’t wear that.”  

“Well you got my black pants dirty yesterday.  You have no choice.”

I groaned.

“Shower.”  she said.  “Use my shampoo, conditioner and body wash”

I groaned again.

Before I got into the shower, I looked in the mirror to see what Kathy was seeing. I looked like a woman.  My hair was now shoulder length and mostly dark brown except for the tips.  I clearly had defined breasts.  My torso with wider hips had the hint of an hourglass figure.  The fat that used to be around my gut seems to have shrunk or moved... elsewhere.  My face... My face looked like my sister’s face.  It was softer and lacked any masculine features.

The only thing that remotely looked like myself? My body hair. Legs, armpits, patches of chest hair just above my breasts.  I also still had hair on my stomach trailing down to my pubic area.

I got into the shower and did what Kathy had asked and used her shampoo and conditioner.  I used the body wash and cleaned everywhere. Except the place I saved for last. My chest.

I layered up some soap in my hands and started cleaning my breasts.  They were definitely sensitive.  It actually felt good.  My penis twitched from those sensations.  I noticed that it started to get hard.

I tried to focus on the task at hand and put those thoughts out of my head.  Maybe I could play with them later tonight.  After all, I’m a dude.  Dude’s play with breasts.  I just happen to have my own pair.  That’s not weird right?  I started to get harder.  Stop. Focus.

After I was done I turned off the water and left the shower.  I grabbed a towel and dried off.  I looked at the mirror embarrassed at the loss of my masculinity.  Just a few minutes ago I was excited about it.  Now I’m embarrassed. I’m so confused.  I wrapped the towel around my chest to hide my shame.  Kathy and Speckles were sitting on the bed waiting for me.  

Kathy first handed me a pair of purple panties.  I pulled those on.  I blushed.  This was embarrassing.

She then handed me the bra.   I held it in my hand unsure what she wanted me to do.

She saw my reluctance.  “You were wearing my sports bra, and jeans yesterday, no problem.”

I sighed.  I then used one hand and pushed the cups up to my boobs as the other hand tried to wrap the hand around my back.

She laughed.  “This is too funny.  Keep going.”

“Come on babe.” I said.  “I’m struggling here.  I’ve only ever removed bras.”

“OK” she said.  “Put the bra backwards so you can see the clasp.  Hook them together.  Rotate the bra, put your boobs in the cups then pull the straps over your shoulders.  Adjust.”

I did as she said.  It was much easier.  My new boobs didn’t fill the cups completely.  “It’s too big.” I said.

“No one will notice since you’ll be wearing a shirt that doesn’t show off your cleavage.

My cleavage?

I pulled on the leggings.  Kathy helped adjust them since I had them bunched up every which way.

“Are you enjoying this?”  I asked

“I find it just a little amusing.” she replied.

She handed me the shirt.  At least a shirt is a shirt so that wasn’t so bad.  The sleeves were higher than I’m used to and the torso was more form fitting.

I asked Kathy to tie my hair into a ponytail.  I told myself I’d get a haircut later tonight.  I just wonder if it was too late.  Would a hair cut even make me look more masculine at this point?

“Listen Aaron.” Kathy said, looking at me.  Her eyes were watery.  She placed her hands on my shoulders.  “When you come home tonight, I won’t be here.  I’m going to stay with my parents for a bit.”

“But why?”  I asked.

“I just - I just need time.”

I feel like I’ve just been punched in the gut.

“But babe-”

“Please Aaron, don’t make this any harder than it needs to be.  Please respect my desire for time to work this out on my own.  I stayed long enough to help you this morning.  I just need time to myself.”

“Ok.”  I said.  My eyes were watering too.  

I walked out to the kitchen and Speckles followed me.  Kathy didn’t.

I took care of the dog’s breakfast and made myself lunch.  

I’m losing control of my life.  It’s spiraling out of control.  I needed help.  I needed help from a woman right now.  I really wanted that help to come from Kathy.  Maybe it will later, but right now she needs her space.

If this was 10 years ago, I’d just call up my sister, Emily.  There were many times I’d call her about relationship advice and we’d just talk for hours and have an honest conversation.  She was the first family member who I introduced Kathy to.  She never sugar coated anything and always gave me honest answers and advice.  I could really use that right about now.

I opened the door to leave the house.  “Kathy, I’m leaving.”  It hurt to say that knowing that she won’t be here to greet me tonight.  I really hope this isn’t the last goodbye.  I wiped a tear from my cheek, and I left the house.

I suppose it wouldn’t hurt to call Emily now.  What do I tell her?  That I’ve been changing into a woman for the past 3 days?  That’s crazy.  My situation is right out of a science fiction story. Maybe i’ll just give her the abridged version.

I sat down in my car, I picked up my cell phone and dialed Emily.  I hadn’t talked to Emily in months.  We certainly haven’t seen each other since before the pandemic.  She’s got her own family now to worry about.

She answered on the 2nd ring.  “Hi Aaron, what’s up?”

“Em, I need help.”

“What’s going on?”

“It’s a long story, but right now.. I’ve been..”  I was looking for the right words to use.  Maybe I should just stick to the story Kathy advised me to use.  “Transitioning...”

“Transitioning?  Transitioning to what?  A new house?  A new job?”

“Into a woman.” I said meekly.

She was silent for a moment.  “Into a woman?” she said in a surprised tone.  “Aaron, You’re trans and you didn’t tell us?  How long have you known?”

“It’s a longer story than that.”  I replied.  “I really need a woman’s help and advice right now.  I was wondering if maybe I could just sit and talk with you this evening.  I’m trying to get a handle on my life, and you’ve always been there for me when we were younger.”

“Absolutely” she said. “If my... sister needs my help, I’ll be there.”

Hearing Emily refer to me as her sister felt weird.  “Oh no - you don’t need to physically come here.”

“I’m coming Aaron.  I can get away this weekend.  Expect me Saturday.”

“Thank you Em.”

I didn’t want to interrupt her life, but hearing her say that she’ll be here in a few days made me feel better.

* * *

I walked into the grocery store and got straight to work.  I wanted to make sure I got as little interaction with my coworkers as possible.  Especially those workers who I was introduced to on Tuesday when I still looked like a man.

I wasn’t able to avoid Ben, who to his credit seemed genuinely happy to see me, regardless how I looked.

Mike pulled me over to the side at one point in the morning.

“Aaron, is there something you’d like to tell me?”

Not really.  “No.  I’m almost done with this section.  About to go for another cart.”  I said, pretending as if nothing was wrong.

“Well, you look like…”  I could see his gaze drift to my chest.  I didn’t like this guy before.  I certainly don’t like him now.  But he’s my boss.

“What do I look like, Mike?”  Come on, give me a reason to call you out.

“It’s nothing.”  he said.

Good.  Confrontation avoided.  My heart was beating fast.  I didn’t know what I was going to do there.

The rest of the morning went by without any more incidents.  At lunch time I walked into the lunch room with my sandwich.  Darcy saw me and waved me over.  She was chatting with some of the employees at the other table.

“Everyone, have you met Erin?” she said to the group at the table.  “She started Tuesday.”

Oh no.  She called me Erin again.  She called me “she.” 

“Hi Erin.” came a few greetings from the table.

I turned red.  No.  This is NOT how you get control of this situation.  Now everyone here thinks I’m a woman named Erin.  Do I correct them?

“Thanks for the warm welcome.”  I said in a higher octave.  Oh my god, I can’t believe I’m playing along with this.  I’m so embarrassed.

Clearly Darcy noticed my embarrassment.  She pulled me aside.  “I’m so sorry.  Did I embarrass you?”

“I’m just used to staying to myself.”  I replied to her.

“I’m so sorry.  I understand.” she said.  “If there's anything I can do, let me know.”

“Thanks Darcy.”

I found an empty table.  I was about to eat my sandwich when Ben came and sat next to me.  “Can I sit here?”  

“Sure.”  I said.  I really just wanted to be by myself.

“I noticed that you look a little down today.” he said.

“Yeah. It’s been a rough week.  Lots of... um… changes.  My girlfriend might be breaking up with me.  My world’s a mess.”

“Hang in there.”  he said.  “I want to let you know that what you’re doing is so cool.”  He then lowered his voice to a whisper.  “I envy you.”

That took me by surprise.  I scooted a little closer so I could whisper back.  “You envy me?”

“Yes.” he said.   “It’s so brave to transition like you’re doing.  You’re doing it with so much confidence.”

Ug.  Another person thinking I’m transitioning.

“I wish I had that kind of courage to do it myself.” he added.

I let those words sit for a second.  “Ben.” I asked.  “You’re trans?”

He smiled. “You’re the first person I’ve told - in real life.  I’m in a whole bunch of online support groups, but I haven't come out yet to anyone I know.”

I was speechless.  I barely know Ben, and he just shared something very personal with me.

“So when you wanted to hang out...”.

He laughed.  “I really wanted a friend.  Maybe someone I could have a um… girls night with.  I really need a friend where I can just be… myself.  I thought maybe I could be myself with someone who was just like me.  Like you.”

“Ben I’m not much of a girl.  I’m not sure how much I can help.  I’m struggling as is.  I’m a complete disaster.”

“Oh. I’m sorry for intruding then.”  he said looking disappointed.

“No no, Ben”  I replied.  “I mean.  I’m very new at this. I do need help.”  Sure, I didn’t know what I was doing, but surrounding myself with people who did sounded like a decent plan.  “I could use a friend too.  You suggested we hang out.  How about tomorrow?”

“I’d like that.”  Ben said smiling.

* * *

When I left work, I sat in my car.  I need to get control of my life. Slowly everyone around me is believing I'm either a woman or a transwoman.   Maybe Dr. Fry has made some progress.

I picked up my phone, scrolled through my recent calls and called Dr. Fry. 

There was no ringing.  Just a message. “This number has been disconnected.”

What?  Disconnected?  Should I drive straight to his office and give him a piece of my mind?

I need to get control. Wait, I can control my hair.  So I drove straight to a salon to get my hair cut.  

After a COVID19 waiver and a temperature check, I was able to sit down. 

I stared at the mirror and saw a woman with a ponytail now past her shoulders.  I suddenly felt anxious.  Is this what I wanted to do?  Cut my hair back to the way it was?  I pulled the hair tie out and let my hair fall down.   I ran my finger through my hair to see what it looked like, down.   I look cute.  The girl in the mirror I mean.  Not me.  There was a part of me anxious to see how I would eventually turn out when this process was done.  The other half of me just wanted to cut it all off.

“What can I do for you?” the stylist said. “Wow, you have very thick and healthy hair” she said running her fingers through it. 

“I uh…”  I wanted to tell her to cut it all off.  I couldn’t push the words out of my mouth. “Just a clean up”  I heard myself say.

 “I see you could use some coloring.  Do you want to go back to your natural hair color?”

“Yes” I said, not realizing that she meant the dark brown roots.

“I can clean this up and add some layering.  It looks like you haven’t gotten a haircut in a long time.”

“Yeah”  I said.  “It’s been a while.”

I couldn’t bring myself to getting it all cut off.  I couldn’t do it.  The one thing I can control.  The one thing that could bring me closer back to Aaron, and I couldn’t do it.   I was letting her give me a woman's haircut.

She dyed my hair a shade similar to the new color that was coming in.  She trimmed my hair back to shoulder length again. 

When I turned back to the mirror I didn’t even recognize myself anymore.  The hair looked good.  I look like Emily’s sister.

* * *

When I got home.  The house was quiet.  Speckles was sitting on the couch eagerly awaiting dinner.

After I fed Speckles and myself I sat down on the couch.  

I pulled out my phone and texted Kathy. “Hey babe.  I was thinking of you.  I just wanted to let you know that I still love you.  I’m still the same person you fell in love with.”

I wanted to watch TV.  But I just wasn’t in the mood.  I was feeling an incredible pain in my groin.  It felt like blue balls.  Now granted, I haven’t had sexual release since Monday night, but I haven’t felt this way since I was a teenager.

Maybe I just need to rub one out.  I found a box of tissues and sat back down on the couch.

I slouched over and unzipped my pants.  I pulled out my dick.  It was looking thinner.  

I started stroking it, but it wasn’t getting hard.  I licked my fingers and played with the head.  That felt nice and my penis throbbed a little, but It wasn’t hard enough.

I looked down at my chest, and I felt a twitch of my penis.  That’s right, I’ve got my own breasts to look at!  

I pulled off my shirt and looked down at my cleavage, that got my penis’s attention. 

After a few minutes of stroking I realized I was having the same problem as last night.  I unstrapped my bra - I mean Kathy’s bra -  and pulled it off.  

I stroked while looking at my own breasts.  I still wasn’t able to get the release I desired.

I cupped my breast and rubbed one of my nipples, and suddenly my penis got rock hard.

I gasp.  “Oh shit. That’s it.”

I started rubbing my nipple as I jerked off.  It was nice.  It felt good, but I wasn’t near release yet.  In fact it was starting to hurt.

I reached down to my scrotum.  It felt like it was crushing my nuts.

Oh God - it was a mixture of pleasure and pain.  I feel like I’m just making it worse.  I just need release. I can’t stop.

I continued playing with my tits while stroking my penis.  Harder faster.  I wet my fingers as I pinched my nipples.

Oh God It’s coming.  Oh no it hurts so bad, yet it feels so good. Faster.  Faster.  It felt like my ball sack was crushing my balls.

I started to scream “Oh God!”  I heard my voice crack.

Faster.  Almost there. I felt something pop and fill my abdomen.  Was that my balls?  Faster.  As I climaxed, I heard a feminine scream.  Was that me?  Suddenly I had the largest ejaculation ever into my hand.

I slid off the couch  and onto the floor out of breath.  Still in mild pain.  

When I got my bearing I reached down for my dick and realized my scrotum was gone.  I ran to the mirror to look.  Just under my penis was a very contracted and empty scrotum.  

“Shit.  They’re gone.”  I said in a higher octave.  Wait.  That wasn’t my voice.  I looked at my neck.  My Adam's apple was gone too.  

“Oh fuck!” I said in a cute voice.



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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