Crossdressing Stories

My Initiation into Feminization (Part 1)

Crossdressing story - my initiation to feminization

I have titled my story, ” My Initiation.” Why may you ask? Well it was the beginning of my feminization and the end to me, being an Alpha male. It was several weeks after my eighteenth birthday that I won a substantial amount of money on a lottery that I was doing, since my eighteenth. Not enough to go to the moon and back, but sufficient to treat my mom, sister, aunt and her daughters, who are my two girl cousins.

All arrangements had been made, so it was held in my aunt’s hamlet, a place about forty odd miles or so from our house. The Bell and Tower, a lovely restaurant there, with fine food. It was a lovely summer’s early evening and after the meal and everything paid for, we all walked back to my aunt’s.



Taking a different way, my cousins asked if they could go through the park, to show me where they hung-out, when younger. So my aunt and mom, carried on, the way we had come, but my sister Debbie, my cousins Miranda and Helen, plus myself, walked through the kissing gate to the park.

After a while, there they showed me a stream with an iron pipe across it, and told Debbie and myself, they used to dare other kids to cross on it, and then asked Debbie, do you wish to try?

No way, came her answer.

Well Graham, are you man enough, comes Miranda, looking right at me.

Yes, I’ll do it, to keep you girls pleased.

So gingerly, I began to walk across it, and half way, I began to show off, by standing on one leg. Not good, I lost balance and fell into the pool below, which was deep enough not for me to hurt, but only got soaked.

Well the girls laughed, at my misfortune, but now I was drenched and would have to ride home in mom’s car, all wet. When we got to aunt’s home, the girls ran ahead to enlighten their mom and our mom.

Don’t you dare venture in here Graham, mom’s voice hollered. Get those wet clothes off outside.

Mom please, I need a change of clothing.



Why on earth did you fool around, in the knowing mom has to return early, to be up for work in the morning. You’re not getting into the car like that.

I pleaded with mom, but aunt intervened, it’s alright Graham, take off all, but you can leave your pants on.

I did as told, and all watched me, as my aunt wrapped a towel around me outside the conservatory. Aunt held it, while mom, under it, pulled my pants off.

Please mom, I called out.

Oh don’t be silly, mom gave birth to you and has bathed you as a boy, I know what you have there and so does your aunt and the three girls here.

IN you go sweetie auntie saying, as she told my mom, she would see to my clothes for him.

You will do no such thing mom saying to aunt, just give me a bin bag and I will take them home.

Mom, what do I wear to go home?

I shall find something for you Graham, don’t fret babes, aunties voice.

My cousins ran a hot bath for me, and while waiting, unknowing to me, mom and my sister, bid a farewell to aunt and thanked her for such a lovely day.

Are you not waiting for Graham?, aunt now a little intrigued.

No, I am not, he can learn a lesson from this, if it is okay with you, Janet, mom said to her sister.

Of course, we shall love having him here.

Well if it is okay with you and the girls, I shall come for him on Sunday next, and mom pulled out cash from her purse and handed it to her sister.

No, no aunt saying to mom, but mom insisted, aunt take it, for my trouble.

All this was unknown to me, as I was now in the bathtub. I did not hear mom and my sister leave, and the car pulled away. I just wondered what I was wearing after my bath. After all, only my aunt and cousins there were female. Mm maybe a pair of slacks and a shirt. Oh well, aunt won’t have me naked going home.



Right young man as aunt entered the bathroom, we best get you all scrubbed-up.

Aunt please, I am not a little boy now.

Oh be quiet, or I shall take you out of that tub, and spank you hard.

Aunt shampooed my hair, commenting how good length it is to have a ponytail.

I heard Miranda and Helen call out, ” do you need help mom, to wash him?

Well, if you girls would like to prepare the bed for me please, like mom did for you, when you were little girls. I heard laughter and girl’s chatter.

What are they laughing for aunt Janet, as told me to stand in the bath.

Miranda and Helen entered the bathroom, and saw me stood stark naked.

Aunt, tell them to leave. Oh don’t be such a shy girl, we are all girls together here now.

Girls together, I asked, but I’m a boy aunt.

Not for much longer sweetie and the girls burst out laughing.

Now sweetie, into my bedroom, the girls have prepared everything for you. I had to lie on a beach towel, while aunt liberally shook talcum powder all over me. Then baby cream under my arms and down there, as she watched my reaction and so did Miranda and Helen.

Oh please aunt, I now knew, I would become aroused, and in front of all. I am so sorry aunt, but it’s so nice you are applying the cream, as aunt smiled and understood, by nodding an approval.



My cousins who were senior to me in age, just gazed at it, squealing with delight. Then came my shock, as aunt held up a matching pink bra and knickers. Miranda holding up the half slip and pantyhose. Helen, the polka dot dress, and shoes.

No please no, I can’t wear girl’s clothes, please aunt.

Oh well, stay in the nude, but I am having four women friends here tomorrow for tea, you will be seen by all of them. Do you wish to be seen naked ?

No aunt.

Well girl, we best get you dressed now. We have much work to do, in order to emasculate you, in the time we have left. You shall wear them until 10 P.M; then into your pretty little girl’s nightdress, you are going.

Where am I to sleep aunt?

Well girl, the girls have their own room and only three bedrooms here, so you are in with your aunt.

Continue to Part 2>> https://allaboutcd.com/my-initiation-into-feminization-part-2/

Written by Miss Jane Wyn.

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3 Comments

  1. I’m a cross dresser who wishes to permanently transition into a woman!

  2. I love you.

  3. i love to be dress as a woman

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