Crossdressing Stories

The Choice of Dress – My Crossdressing Story

choice of dress - crossdressing story

I had just finished washing the dishes, when a knock on the front door. So, dried my hands, and opened it. Not thinking, I was still wearing a floral print apron, with ruffles around the edge.

Oh Miss Lewis, how can I help you, I asked?

Is your mom at home sweetie?, smiling at my apron.

No, mom has just gone with my sister, to town, on a girlie shopping spree.

So you have not gone with them, I see.

No, I just stayed to tidy-up, before they return this evening.

Well I must say, you are a very good one, aren’t you?

Thank you, but can I help you, Miss Lewis.

Well, as you can see, I have a mail order catalog here, and I am in a dilemma, which dress to choose, for a party, with the women, of the village group, next weekend.

Oh never mind, I’ll call again.

No, wait, it maybe too late, by then, if you have not ordered the dress, and the day be next weekend. I can help you, to make up your mind, Miss Lewis.

Well, do you know anything about dresses, sweetie?

Well enough to choose for my mom and sister on times, as they also, ask my advice, as mom and sis, say, I have a good taste in women’s clothes.

Oh very well, I trust you, her now handing me the catalog.

Please come in and make yourself at home. Would you like a tea, coffee or wine?

Well thank you my girl, she answered, a wine please.

Red or white?

White please young lady.

That is twice now, Miss Lewis has referred to me in the female gender. Oh, well she must be teasing, me, with this apron on.

Would you like something to eat, with it?

Oh sweetie, you’re spoiling me. I wish you were living with me, or visit occasionally, and you would do well, as my maid. Have you a chocolate bar sweetie?

Yes, I shall take wine with you, if you not mind, and a bar each.

It’s your home my girl.

Miss Lewis, you are a tease.

Am I sweetie. In which way?

You, addressing me as a young lady, and a girl.

Oh, please forgive me, but you with that pretty girl’s apron on, I just had to.

I best take it off.

No, please, don’t. I like it on you, it suits you, with that blue top and those shorts, but tell me Graham. You are aware that everything on you, I have seen are ladies’ wear.

Yes, you are very observant Miss Lewis.

Can I ask you the reason why sweetie?

Well, when I am here, I like to dress up.

You mean, your mom and sister are quite oblivious to it.

oh no, on the contrary, they both know, and not only permit it, but encourage me to dress up.

My, this is so hot and I have read on this, but never have encountered a cross dresser before now. Well, it’s your home and your business, let me show you the two dresses.

She then turns to the catalog and shows me photos of  dresses. Miss Lewis, pointed to both, but I was not fussed on either.

If you wish to wear either, then this one I would choose, but if you like my opinion, this dress here, I pointed to, on the other page.

Miss Lewis, smiling at me, saying, I bet it would look good on you, shall I order it for you, my girl?

No, no, I cannot accept that Miss Lewis, I would pay for it myself. I shall order both dresses, one for me and this one you like, for you.

Now no more said, in a commanding tone, telling me. Well let me, do some work for you, and I will feel much better for it. oh, alright, if you persist.

You, are aware, that I am a seamstress.

Seamstress, Miss Lewis?

Yes, girl, a dressmaker.

Well, if you make dresses, why buy this one.

Occasionally sweetie, I too like to buy a pretty dress, for myself.

I understand, but how can I help you?

I need you, to model some dresses for me, just to sew the hem of each dress and see how it looks on the woman, that has asked me to make it for her.

Well, why not ask the woman?

Oh, on times, the woman, who wishes the dress, just has no time to visit, for that, but you my dear, are about the size and build of the women, that be my customers. It’s only a dress Graham. I am not asking you, to put your hand in the fire.

Yes, I will do it, Miss Lewis.

We ended up, drinking the whole bottle of wine, between us.

Now shall I open another bottle Miss Lewis, as we now had the taste for it, and it were a hot summers’ day.

Oh my, you are a very naughty girl, aren’t you, trying to get me drunk, to take me to your bed, and have your wicked way with me, as her hand rubbed up my thigh. My you are very pretty Graham, for a boy. It’s a real shame, you were not born a girl.

Tell me Graham, are you wearing knickers?

The wine now, hitting us both and making us tipsy.

Yes MA-AM, as now my voice were high, and excited.

I want to see your knickers, to see what color they are.

PINK, they are pink.

Yes, but still want to see them girl.

Take everything off, show me your girl’s knickers. NOW GIRL!!

I thought best to do it, as she would rip all my clothes off.

Do it like a strip-tease, your flats, ( shoes ) shorts, top, and now mm, lovely pink knickers, as she grabbed me, and threw me over her lap, as I were only like 5 foot three inches, and her a buxom woman, with strength.

I am going to pull your pink girl’s knickers down, so I can spank you, and oh my we have a little wriggler, as I attempted to liberate myself, from her grip.

To no avail girl, you are going anywhere, until you have had a very severe bottom warming.

No please Miss, I beg you, as she  ripped my knickers down.

My what a cute girl’s bum you have, very nice indeed, and SLAP, SLAP, SLAP.

I cried out, with her calling me a very horn-y naughty girl.

Once it were over, Miss Lewis, pulled them right off me, and stood me naked there.

Gripping my wrists, so not to cover my genital-ia, she told me, surely your not shy or embarrassed girl, we are all girls here.

Now sweetie, I need the bathroom, after all that wine, so you are accompanying me, and if I am right, you too need to pee. Once in the bathroom, told me to stand with hands on my head, and watch her. T

Then dropping her knickers to her heels, kicked them off, and ordered me to don them. My you look good in my knickers, which were a lemon yellow color.

I want you to wear them, when you arrive for the dress fitting.

Now girl, go and pee, and you had better sit.

I did as told, then wiped.

That’s my girl, her smiling, and we washed our hands, then she gripped my wrist and nigh-on dragged me to my bedroom.

Are you a virgin Graham?

Yes, Miss Lewis.

Good, because today, I am going to deflower you, of your innocence.

Miss Lewis threw me on the bed, and shut the bedroom door. Well, no need to continue, as we all know what happened to Graham, in there.

Written by Miss Jane Wyn Jones.

Facebook Comments

1 Comment

  1. I love that story like me in every way. By miss Jane wyn John’s. About miss Lewis

Leave a reply

Your email address will not be published. Required fields are marked *

You may also like