Aunt Gloria dresses me up as a girl.

[Pink5Frills]

Aunt Gloria, has many times told me, I should have been a girl. Then on my summer holiday there, aunt asks me to don a dress for her, as she needs to fix the hem, as aunt Gloria, is a seamstress and dressmaker, and many women visit her to have their clothes adjusted. Once aunt has bathed and shaved me, enlightening me, I had to be clean, as the dress belonged to a lady who is a school teacher in an all girl's school.

 

[AllenJames]

Perhaps offering a night gown in which to sleep as it will be cooler during the summer

 

[Pink5Frills]

Perhaps offering a night gown in which to sleep as it will be cooler during the summer

Where are your pajamas James, asks aunt Gloria? I have none aunt. Yes here, but at home. I shyly confessed that mom never bought me a pair of pajamas not even girl's pajamas, as mom tod me, a nightdress is cooler in summer and mommy has warmer nighties for you in winter. Aunt smiled, and telling me, as i stood stark naked before her, well sweetie, it seems you will continue to wear a nightdress here now, as aunt went to her room and returned holding a pink ankle length nightdress for me. I felt my penis become aroused and had a rampant erection right there in front of aunt Gloria. Aunt chuckled, saying well some little boy will enjoy wearing it, referring now to my erection. Gosh, I was twenty years of age, still a virgin and that would soon be rectified, when aunt would deflower me in her bed.

 

[ElliottEden]

I think you've got something here, especially if these items from your list are incorporated.

Perhaps then some changes? Your aunt remains a seamstress, and she has told you several times that you should have been a girl. An opinion that's also shared with your mother.

One of her clients, the head mistress of the local girls school has brought a dress in to be hemmed. Your aunt calls you into the room which acts as her shop, and suggests that you help out by donning the dress. That way it drapes properly and she can assure that the hem is even. The client is at first amused by the idea but soon agrees with your aunt.

You balk at the idea at first and after several moments the school mistress takes you by the hand and bends you over a worktable - then uses a sturdy ruler your aunt uses for cutting cloth and spanks your bottom. Shamed and cowed you submit, at which time both ladies bring you to your aunt's bathroom where you are bathed, shaved and prepared by them for the rest of the fitting.

From there the rest of your adventures can unfold.

 

[LupusDei]

One of her clients, the head mistress of the local girls school has brought a dress in to be hemmed. Your aunt calls you into the room...

Does this this organically lead to him being transferred to said all-girls school, for a great "secret" delight of the other students there?

 

[Pink5Frills]

Does this this organically lead to him being transferred to said all-girls school, for a great "secret" delight of the other students there?

Yes, he is enrolled in an all girl's school and has to wear the uniform of the girls there.

 

[LupusDei]

Yes, he is enrolled in an all girl's school and has to wear the uniform of the girls there.

But the sports hall showers there are old fashioned big room with multiple showerheads along the sides.

 

[Pink5Frills]

But the sports hall showers there are old fashioned big room with multiple showerheads along the sides.

You will take a shower in the communal school shower with the other girls he is told. Oh please, I am a boy, not a girl. Can I not shower after the girls have gone? No you can not, and why all this ado young lady? This is a nightmare, to be stark naked in the showers with the girls hockey or netball team. You will soon get used to it, after all you are a girl now.

 

[BrattyLinds]

You will take a shower in the communal school shower with the other girls he is told. Oh please, I am a boy, not a girl. Can I not shower after the girls have gone? No you can not, and why all this ado young lady? This is a nightmare, to be stark naked in the showers with the girls hockey or netball team. You will soon get used to it, after all you are a girl now.

Just so you're aware, you're not in the Sexual Role Play board...

 

[Pink5Frills]

Just so you're aware, you're not in the Sexual Role Play board...

Yes, I understand, and thank you. Do you wish to continue this scenario with me?