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Phillips Fantasy

Phillip is a boy who discovered my acceptance of boys dressed as girls
His joy is emense and especially when he feels caught ,
I could see this the first time I visited him he let me catch him , his shame
and embrassment seemed a little bit less than real to me ,yet I played along
and let him have full enjoyment of his situation.

Phillip continued to act surprised and shocked whenever I discovered him
in a dress or found him wearing pantyhose under his trousers.

I knew I had to do something to real make Phillip feel enjoyment, so I suggested to him this-
how bout I dress you up like agirl with make-up the whole works
some day when you are home alone, then when Mom comes home
she catches you in the bathroom

you then try to explain a girl did this to you ,and shes in your bedroom
I then appear and we go from there

Phillip was excited and willing to do this with me, I dress him up and applied
mae-up and even nail polish- put bows in his hair- he looked super cute
we waited for a car to come in the driveway , then Phillip dashed into the bathroom
and closed the door
I made his excitement further, instead of staying in his bedroom, I sneaked out the back door.

Phillip was left to explain his appearance without me there- I believe his
Dad came in the house and not Mom -
if he's able to I will let him tell us what happened then.
MissPenny MissPenny 18-21, F 11 Responses Jul 28, 2012

Your Response


Oh wow! I think you did a fantastic job at helping him :)

*goes all quiet thinking about Phillip's humiliation- shivers*

did you ever find out what happened? if you had stayed maybe you could have talked dad into a dress, too.

Thats a great humiliation story. I used to love doing that, My sister would get me all girlied up and we would sit on the coach and let mom come home and see me in my pretty dresses.
Mom just ask if I liked dressing that way, and I said yes, so she finally let my sister dress me everyday.

Omg you little devil you. I bet he was really embarrassed and do please find out.

oh, that is sneaky! so what happened?

Ms. Penny, I too, wish you had stayed, maybe you could have smoothed things out, and maybe helped his son, but, I was curious, if you knew it would be his father, do you think you would have stayed. I hope he was able to have this experience, long enough for his mom to see him, she probably would have had a clearer picture of the situation, the more I read your stories, the more impressed I am with your level of maturity. Have you been around much younger boys, that you were able to encourage to dress up?, please continue your amazing writing, I hope sometime you will share more photos of your successes, loving and caring,<br />

Hope he's all right and tells us what all happened

Well, you certainly made it real for him to be caught and not just playing around.<br />
I as well am wanting to know what happened.

Miss Penny, I also have a group along side andrea for having an opposite party. Maybe you and the girls could do this before school starts, have all the boys you know came to the party as a girl, in a dress or skirt. Ask Andrea about the group.

WE need to hear his story as to what happened. Maybe Dad dressed up with him.