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Auntie Knows Best

Aunt dressing up nephew as girl

Friday is the last day of college, before the summer break. I arrived home, and while mom was preparing dinner, I read the letter from aunt Joan, stating she would like to see me sometime in the summer holidays, as my aunt had not seen me for several years. So I chatted with mom, and she told me to go and spend some time with your aunt.

Saturday morning I was up early and caught the bus to the inter-station, then a bus all the way to my aunts. Aunt could not welcome me enough when she opened the door, and commented on how I had grown and what a good looking young man you are.



Well after the preliminaries, I took my aunt out to the local restaurant to wine and dine. On our return, I happened to notice a pretty pink sunray pleated skirt in the window of the Boutique. Oh aunt, that skirt is really nice, and if I were a girl, I would buy it now, one saying to aunt.

My dear James, you do not have to be a girl to wear a skirt. I looked at my aunt and there was a lovely smile on her face.

“If you would wear it, I shall buy it for you.”

“No aunt it’s alright, as I blushed a bright tomato red.”

We walked back and chatted on how wonderful it is to be out on such a summer afternoon, and the evening be just as pleasant.



We took tea and some cakes I had bought, on our return. The phone rang and my aunt answered.

“Oh my, well it can’t be helped, I shall try to do it without her” aunt speaking to whoever was on the line.

The phone replaced, I asked aunt was there anything wrong?

“No James, just that the girl who was supposed to be here Sunday, for her dress fitting, has gone down with a cold. I shall try to do it without her now.”



“Well aunt if I could help I would, but how can I?”

Aunt Joan, is a seamstress and dressmaker and looked at me.

“James, you are a wonder. Of course you can help. You look the same height as Susan, ( the girl who was supposed to be there ) and about the right figure. Oh sweetie you are a dear, I can do it without her and I bet it will fit her.”

“You mean you wish me to stand for you to take measurements and be the girl?”

“Yes please James. Oh thank you James.”

I had not even agreed, but now I could not upset my aunt and her disappointed.



“Go and strip off James, while I run a bath for you. I always insist the customer, be it a girl or woman to shower or bath before arriving for the fitting.”

I did so and not realizing that my aunt added some of her toiletries to the bath-water.

I entered the bathroom, and my aunt was there.

“James, do you usually bath in your underpants?”

“No aunt.”

“Well take them off boy.”

“Once you vacate the room aunt.”

“Don’t be silly, now I am your aunt” and she approached me and asked me is that a spider on the ceiling?



I looked up and with one swift move, my aunt took my pants to my feet and told me to step out of them now. I did so more in shock, as I was now stark naked. I went to cover my privates and my aunt stopped me, saying we are all girls here.

I felt my strength sapping away from me with those words.

“Into the tub you go Jane and be quick about it.”

“Jane, whose Jane?”

“You are my dear, you surely do not wish to be addressed as James, wearing a dress.”

“Now you soak there and I shall return in a while to wash you all over.”



Aunt picked my underpants up and took them with her. About fifteen minutes later, my aunt returned, and washed and shampooed my hair.

“I like your long hair Jane, it does become you my dear.”

I wanted to tell my aunt, I only agreed to stand for her to do the dress fitting, but now I was already being called Jane and I dare not protest, as I was naked in the bath.

Once rinsed down, dried and then to the bedroom.

“Now it is fortunate I do sell some underwear here for girls and women, so best measure your bust waist and hips girl.”

I stood nude as my aunt measured me for what would be girl’s underwear.

“Bra, you need a 36 B, waist is slim, and your hips a nice 36. Oh my gosh, you really have a nice figure, and many girls would like what you have” Aunt fussed over the lingerie, then brought forth a white lace bra and matching panties set.



“Now stand still please Jane, as I need your bust the same as Susan’s”.

The bra was put on me and fastened, and I felt trapped. These inserts shall do the trick, to a nice 36B Cup. Then I had to step into the white panties holding on to my aunt. I felt them drawing up my legs to my intimate parts. I shivered, but not with a chill, but with excitement.

Aunt gazed at me and smiled.

“You shall need the full set my love, that is garter-belt, stockings and a full slip.”

I could not believe it. Aunt found it all and placed it on me.

“Shoes, let me see, Susan is a size 5, and by luck so you are my sweet niece Jane.”

I wanted to flee, but how could I, not like this in women’s underwear.


“Jane, please walk around my dear, as you must get used to the heels.”

“Aunt, I am only standing for a dress fitting, I am not going to be doing this on a regular basis.”

Aunt smiled, saying, “we will see.”

Aunt did my hair and applied make-up, telling me, if anyone should visit now, you will look like a teenage girl and not a teenage boy wearing girl’s underwear. I twirled for her and my full slip billowed outward. It felt odd, but I liked it. Aunt was no fool and detected my liking for wearing girl’s intimates.

“Now sweetie, the dress”, and it fitted me without any alterations needed.



Aunt was pleased, and phoned Susan’s mom who was told that her nephew had helped out with the fitting, and he really looks like a girl in it. I could not believe it, when my aunt replaced the receiver, telling me she would take photos of me now, to send via email to Susan’s mom, who would surely show her daughter. I pleaded no, but somehow it was futile, as protesting wearing girls’ clothes seemed to weaken me.

I had in such a short time become emasculated. The dress was taken off me and my aunt thanked me.

“I have a pretty dress here for you Jane, so you are not walking around in your underwear girl.”

“Aunt, I cannot be like this all evening.”

“Why not? you look great as a girl.”

“I am going to change into my clothes”, and as I went to vacate the lounge, my aunt called out to me, “oh those clothes are with Mr. Terry across the road, if you wish to fetch them my dear”.

I stood in women’s undies and was helpless.

“Now Jane, we best get the dress on you that I have chosen for you this evening.”

Submitted by :~ Susan Jane Windford

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1 Comment

  1. that was a darn good story

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