Crossdressing Stories


crossdressing story

It began in my late teenage years, when I use to go around the village, asking people, if they would like a job done around the garden, or something simple, that I can do in the house.

Miss Watkins looked at me, that morning, as if I were her favorite meal, but unaware, that women were so much like men, in need of satisfaction.

Come in, her beckoning me, and sit here, on the chair, in the conservatory. Now, what is it, that you do young man?

Graham: Well Miss Watkins, I usually do manual work, but leave the professional work, to the tradesmen.

Miss Watkins: Well, if you are prepared, I would like a tree stump, by the fish pond, pulled up. Miss Watkins, ushered me to the area, and I looked at it. I

Graham:  It will be a task, but I shall try Miss Watkins.

Miss Watkins: Good, all tools you may need are in the shed.

So off she went and I to work. I spent several hours at the stump, then wrapped a rope around it, and pulled. I assumed it would be a good few hard pulls, before it even shifted, but no, it suddenly came loose and up it came, making me land in the pond, and soaking wet.

Miss Watkins had seen it all, from her back door, then came running down the path, to see if I were hurt or injured.

Miss Watkins: Are you alright Graham?

I stood up in the middle of the pond, water dripping off me.

Miss Watkins: Come on, let’s get you out of there, and into a bath of warm water. I was led to the rear door, then told to strip off. Down to my underpants, then saying ready Miss Watkins, and she telling me, those also young Sir.

Graham:  Miss Watkins, I be naked.

Miss Watkins: Yes, she concurred, but you do not bath at home, in your underpants, do you?

Graham:  No, ma-am.

Miss Watkins: Well off with them.

Graham: I did so and she took me indoors and to her bathroom.

Miss Watkins: Now, there is no need to be embarrassed, just think of me as your aunt Hilda. In you go, as she patted my bottom, in a playful mode. Now you just sit there, and I shall wash you, all over.

Graham:  I cannot see the purpose of this maam, as I will have to don my wet clothes to go home.

Miss Watkins: No, you will not, I shall have them washed in my machine, so don’t vex, now, as she washed me. I think you are embarrassed, by me not seeing you naked, but that bush of yours, as her eyes indicated to my pubic hair.

I nodded a yes.

Miss Watkins: Well, no problem, I shall shave it all off, for you.

I attempted to protest, but to no avail, as I were in her home, in her bathroom, in her tub and naked.

Miss Watkins cleaned every part of my body.

Miss Watkins: Now a rinse off, and dry you.

I stood in the bathroom, on the mat, as she dried me.

Miss Watkins: I have just the clothes for you, and smiled at me. Into her boudoir, I ran to, as again tapping my bottom, her laughing. On the beach towel baby, as it were on her bed. Miss Watkins, and I knew, I was now in her power. Talk all over me, and making me smell, like a girl, as the talc, were of a feminine fragrance. Well, why should it be otherwise, as her daughter and her resided there.

Miss Watkins: Now you are fortunate to be the same dress size as my daughter, and Laura, has placed some clothes, in readiness, for the charity shop, so this dress, I have selected for you.

I stood naked, and bald down there, as she held a light colored leaf green dress up, and smiling.

Miss Watkins: What do you think Graham?

Graham: please I can’t wear a dress, to go home in.

Miss Watkins: Why not?

Graham:  I am a teenage boy.

Miss Watkins: Yes, you are, and many boys like to wear girl’s clothes.

Graham: The dress is lovely ma-am, with a plain bodice and a pleated skirt, I do like it. The full-length sleeves and is it lined, I asked?

Miss Watkins: Mmm, you seem to be well versed in ladies wear, Graham. Are you sure you have not worn girl’s clothes at home? I am aware that you have four older sisters and you are the junior. You must have worn it many times, the hand me downs, around the house, or your mom or sisters dressed you up.

I revealed all to her, by not words, but by blushing and becoming with my excitable voice, a tell-tale.

Miss Watkins: So you have worn girl’s clothes?

Graham:  Yes, yes, but please don’t tell anyone.

Miss Watkins: I shall not, and if you are a good girl now and let me dress you, you and I will possibly become good friends.

Laura, her daughter, were in her early twenties and at university, so it was only her mom and myself there, as she rummaged through her lingerie, to have a matching bra and knickers for me, plus a full slip. Garter-belt and stockings, sweetie, holding them up to me.

Miss Watkins: Do you think it is too warm for them?

Graham:  I was now mesmerized by all this and just yielded to her power over me.

Miss Watkins: Such a cute girl, you are going to look, as I sat in my undies, at the vanity table, while Miss Watkins applied a full make-up; to my face. The dress and it being zipped at the back, I felt now, in a cell. No way I could unzip it myself, and Miss Watkins, knew that. Then she slipped on a pair of heels. which were a white patent court shoe, my hair brushed in a feminine style as it was a good length.

Miss Watkins: Now Graham, look at yourself, as I turned to the full-length dress mirror.

Graham:  I cannot believe it’s me, Miss Watkins.

Miss Watkins: Oh it’s you alright my niece. I knew the moment I espied you at my door, you would look good as a girl.

Graham:  I do, don’t I, but cannot go home like this.

Miss Watkins: Well the only alternative is to walk home naked.

Graham:  My wet clothes ??

“Come here to the window” , as she indicated a black bin bag being taken away, by the council refuse collector.

Miss Watkins: Do you know what is in that bag?

Graham:  My clothes, surely not!!

Miss Watkins: Yes, those horrid boy’s things.

Miss Watkins, handed me a purse with a good amount of cash notes inside.

Miss Watkins: That is for you to buy new clothes, and come now, we are going out to lunch, as I have made arrangements, with my friends Beryl, Iris and Barbara.

What can I do? I cannot protest, not dressed as a girl, so I just went to the front door and into the car. We shall call ourselves, “Take Five Girls.”


Story sent by Graham Jones.

Facebook Comments


  1. I love it

    I would try it

    I wish the same happend to me!!!!!!! 😍😍😍😍

  2. I spent today as a housemaid and wearing a housemaid’s uniform and tabard. I have done it before many times and it makes no difference if there are visitors I still get on with my work unless I am serving refreshments

  3. I an sitting reading this story dressed in long hobble pvc dress with rubber underwear, I am also wearing a pvc apron and everything is locked on. I did enjoy the story and would love to have been put in the situation when I was younger.


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