Crossdressing Stories

My Initiation into Feminization (Part 2)

Crossdressing story - my initiation to feminization

Now dressed up, in girl’s clothes, my aunt Janet, cousins Miranda and Helen, could not believe how much of a girlie appearance it was for them. Without even make-up on.

Then aunt told the both to have fun, but I would like to see this girl, referring to me, with a little make-up on, before bedtime. Aunt vacated her bedroom, and both Helen and Miranda now set to work on my face and hair.

I was wearing a bra, knickers, slip and tights, but the dress and shoes would come later-on as they explained, girls make up, prior to donning their dress and shoes, so you will be knowing in future sweetie. I sat there, on the stool, in front of the vanity case, but my head turned away from the mirror, for the girls to see to my appearance.

Girl chatter between them, as they applied what would be best for my hair, eyes and complexion color. Once complete, Miranda caught my hands and said up girl, then on with the dress and shoes, warning me not to turn toward the mirror, or they would not only chide me, but chastise me. Well, I surely did not wish to be spanked by my girl cousins.

Then the dress as Miranda zipped me up, Helen telling me to step into my shoes, then baby, you can now turn around and see yourself. I gingerly did so, and to my surprise, not horror, I was looking at a teenage girl.

Oh my gosh, I uttered, is that really me?

Yes, that is you, a girl.

Oh gosh, this is too much, I never knew, I would look so good as a girl, and to tell you girls the truth, I like it.

Well babes, glad you do, as you will be looking like this until next Sunday, when your mom returns for you.

Next Sunday, but, have they departed without me?

Yes, came both cousins. I now realized I have to be in girl’s clothes for a whole week. Yes, you, as they both read my mind. Come on, let’s take some photos, for posterity.

No, no, no photos please.

Why not, came the girls? No one will see them, but us three here, not even mom.

The girls had me pose in various stances and squealed with delight looking at them, as some were of us three, with myself in the middle each time, as if to say, you’re going nowhere girl, without us.

Have you girls finished with our little girl, called out my aunt.

Yes, mom, we’re on our way down.

Aunt Janet was in the kitchen and when she turned around to view me, she was taken back at how good a girl I looked.

Oh my goodness, you’re beautiful Graham, but wait, you can’t be a boy, can you. No you will be our little girl Jane.

We all sat to take a light supper and yes, I really enjoyed the feeling as I there in girl’s clothes and my hair and face made up. I thought, well they have seen me naked , so to me, this is not an embarrassment.

Bedtime, I was undressed by my aunt, while the girls sat on the bed watching every move, then the pink nightdress over my head. You best pee, before bed now Jane, as all entered the bathroom to witness me sat to pee like a girl, in my nightie, then more photos were taken of me like that.

Once the girls were satisfied, they kissed me and thanked me for being such a sweet little girl. Then both were gone, as aunt and I now together in the boudoir, aunt began to undress in my presence.

There’s no reason to turn your head Jane, we are all girls in this house. I best end here, or it will be too erotic, to type what happens, when aunt and now her niece, slips into bed, and under the duvet.


Written by Miss Jane Wyn.

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  1. My mom and I went to my uncle Phil, Aunt Amy and cousin Debbie. They wanted to celebrate me starting Junior year. More uncles, aunt’s and cousins.
    Uncle Phil said some boys were playing football. Mom said go play, the other boy cousins moms didn’t want them to get dirty.. My mom would have me sit on towel. She was cool.
    One hour later my mom pulled in park. We were taking a break. We were playing tavkle, there was a little.drozzle. I was already.muddy. Do what your Aunt and Uncle say. I have to go to work now.
    My mom was a ssupervisor for a company that made work uniforms.
    My mom went back real quick to talk toy aumt.I guess. Two hours later my uncle came and got me. We walked back to his house. He jokingly said they’ll have to burn the clothes.
    He turned the hose on me. Got some of the mud My shoes were the best. They were the best cleaned. They were left outside to dry.
    My. Aunt handed a bag for my socks. I came in, she pointed to the laundry room. She had me put the rest in the bag,
    I said Where’s Debbie.? My aunt handed me a towel to wrap around me.
    She told to go to the bathroom..Debbie was sitting in the living room. She had this smile on her. Her mom handed the bag of clothes.Asked her to wash them.
    She replied anything for my favorite cousin. She was 19. She best looking of all my cousins. If she wasn’t my cousin I would have asked her out, even though she was three years older. Home from college.
    My aunt said my mom left me a message. It was on the sink. The bathtub was full of water and purple bubble bath.
    My message. said Do what you uncle and aunt say help them.
    The next part, I hope my aunt didn’t read. I had all my gym credits till grad two years. I told my mom I always wanted to shave my legs. She said Ok. The note do it now.
    I saw my aunt:s or Debbie:s razor it was pink. I took it. I shaved my body totallyMy aunt yelled do you need help shampooing
    No then I heard Debbie mom. I’m sorry I ruined Stevens clothes. I forgot the sheets were soaking in bleach. I threw his clothes on and started them.
    My thoughts what now. I could hide in the attic till my mom get me clothes after work.
    I got dried my hair. I haven’t had a haircut for thirteen months. I was letting it grow. It wasn’t cut short then.
    My aunt yelled towel up. She came in took me to her room.
    On the bed were girl clothes. My aunt said they were Debbie’s when she was sixteen. She said just till your mom gets here with some clothes.
    Get dressed and come down stairs, your uncle ordered pizza. Thirty minutes or less.
    Debbie knocked, I’m towel come on in.
    Can I help. Wouldn’t you want a nineteen year old girl dress you as a girl, for the first time.
    Let’s go to my room she said. I picked up the clothes towel dropped. She didn’t laugh or giggle. She put towel around me and held it.
    We walked to her She said,(‘ I think it’s sexy that you are completely shaved. I am totally bare also.,’)
    She put green panties on first. She picked up the padded bra. (” I got a better idea. She opened her top drawer took out two skin colored breasts. She put the on me pushed the edges and they stuck.
    Then the dress she zipped me up. Then she picked up the hose. She had me sit on the bed. She pulled the hose over my shaved legs. She told me I had sexy legs. Now the hair and light makeup.
    She asked me, (‘ One ponytail or two pigtails..)
    I said,( I trust you. We’re not just .cousins, we’re girlfriends.)
    Ponytail, a hug and kiss. Small amount of green eye shadow. I now have large eyelashes. Light pink on cheeks.
    One inch heels were my shoes. I asked Debbie,(‘On thing the truth. Was this planned or an accident. Truth.)
    Your mom and my mom. I just helped. She started to tear. I grabbed her now look at me. On girlfriend honor don’t tell anyone about what I’m going to say. I always wanted to wear girls clothes. My mom wouldn’t even for Halloween.
    I never thought s beautiful sexy nineteen year old. Would do it.
    She blushed.
    What name are you going to give me. She said Steven to Steffanie.
    We went downstairs. Debbie said and dad here is my new cousin Steffanie.
    Aunt Amy smiled, Uncle Phil looked like he was going to swallow that can.
    Aunt Amy said you girls come and get something to eat before bed.
    I sat in a chair and held my dress. Till I was all the way down. I had two pieces of pizza and a drink.
    Where do I put the roll away bed.for Steffanie. Uncle Phil said, (“If Debbie doesn’t mind she can sleep with her.”.)
    I thought Debbie stopped breathing.
    Debbie said, (“Let’s go Steff. We’ll a sleepover fun..)
    Aunt Amy told us girls layout our dresses for church in the morning.
    Debbie told her the church dresses are in the attic. We went to Debbie’s.
    room. The access to the attic was the
    I hotHerr room was bigger than her parents.
    There was a portable closet on rollers. There were eight dresses that we could fit into. We took all them down to her room
    We were going to have a dress trying on party. One thing before we get busy. Do want to stop girl, she and her.
    (” No, I want you to call me Steffanie or Steff even when I look like Steven. I want all our cousins, aunts uncles. I don’t ever what to forget anything for however long it lasts.,)
    . We need to find out size can walk in. Right now two inch heel. The.light and dark green are the.ones that will work.
    I asked Debbie can the pink one be worn to church.
    Four inch heels. I meant is pink acceptable
    . She handed me a black open toe pair
    I sat on the bed took off the shoes. I put the other ones on. I stood up. No nose on floor or body bounce
    I got.light green,. pink, white and red
    Debbie got dark green, blue, black, and red.
    We both had a pink nightie to wear
    We hung our dresses in the closet. The pink and red was.on the door.
    Debbie asked me to help get her nightie on. She wanted me to see her hairless body, One play time left. You paint my toenails and I’ll do yours She handed deep red bottle. I did hers.
    No mess. Great job Steffan She showed me four different pinks and lig
    I choose the brightest pink. We finished. bedtime.she said, (My turn pp. PThe truth and the whole truth. What did my dad you’)
    No way it wasn’t nice, I replied.
    I know it wasn’t. It look.likr you were going to hit him to the front door on the fly.
    I tell you on nicer language. If you.get a chance to make love go ahead.
    Don’t tell him I’m bisexual. He’ll bug me to make with on his friends son’s.
    We went to bed. We held each other and kissed for good thirty minutes.
    Next morning at breakfast. I got a smile from her dad. I didn’t know why
    I looked at Debbie, I knew why. Through the night dress we had on
    Her right shoulder near collar.bone was a hickey.
    My mom called Aunt Amy was the closest. We just finished breakfast and the girls just getting ready to get dressed for church
    She handed me the phone. My mom wanted to sleep today. The earliest she could come Tuesday after work. I’ll ask them.. The three of you. Can my mom come Saturday, spend the night and go to church with her daughter and sister with her family.
    That would be wonderful. I haven’t been to church with my sister forever.
    They both at the same time. Debbie you have three weeks left before you leave. Would you like Steffanie to stay a week with you,.
    Debbie said, (” That would be awesome. The way she looks. We’ll probably be asked out for a date or two.)
    Go girls get ready. You won’t make college Sunday school. Debbie said I’ll drive her and I. I’ll show her the high school group.
    If anyone wants to know about the week leave a reply..

    1. You need to rewrite this story and then have it checked by a proof reader.

  2. Nice story. I wish I could have some interaction like this.

  3. Just stumbled across these stories and so enjoyed reading them.
    I drool with envy.

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