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Image by SFC78767
I can't believe it myself, Amy, my girlfriend, dressed me as a girl for Halloween (I had agreed in a moment of weakness, we were in bed at the time, need I say more.) when she was finished she said,

"There, even your own mother wouldn't recognize you now Tom" (I hate to say it but it really didn't take much make up to change my boyish looks,)

Mascara, a little blush, eyeliner, and pink lipstick, and I was done.

I never should have doubted her, I told her,

"Don't be ridiculous,  of course she will, she will see right through this get up, I'm her son'',

(Famous last words) Maybe I should have looked in the mirror before I made the deal.

Amy said, "Ok, If she recognizes you, I will wash your car every week for a month" 

I said, "And if she doesn't?" 

"I have a new friend for a month from out of town" Amy answered, "What do you mean" I asked, "Just that, I get to dress you for a month" came the reply.

"Ok It's a deal, but when you clean my car you have to wear your cut off shorts and that short pink tank top of yours," I said. (I was too busy thinking of her bending over the hood of my car with those too short shorts of hers and her chest spilling out of her pink tank top)

Now, it was Halloween, so there were lots of people in fancy dress, but no one gave me a second look, I was getting worried, Amy was smiling like a Cheshire Cat, I was wearing a pure white blouse, royal blue sweater, a grey skirt, then Amy had me roll up the skirt at the waist, to make it short like all the girls do at my school, and white socks that came just below the knee, with flat Mary Jane shoes.


My hair was quite short, but just long enough that she could brush it into a fringe just above my eyelashes, she replaced my stud earrings with two small heart shaped gold earrings. I stepped out onto the street feeling eyes following my every step, as we got closer to my house I was hoping we would walk in and mom would see me and burst out laughing, but the closer we got, the more my legs were shaking, what if she didn't recognize me, and Amy could make me wear whatever she wanted, I was about to back out of the deal, when we were at my front door and Amy was ringing the bell.

When I looked through the frosted glass in the door, I breathed a sigh of relief, I couldn't make out who it was, but I could see it wasn't my mom, the door opened, I starred at the person in disbelief, it was Dave my best friend, first I was so glad it wasn't mom and then I started to freak out, IT WAS MY BEST FRIEND ARGGHH,

Amy didn't bat an eyelid, she stepped into the house and turned to Dave and said,

"Hi Dave this is !!!!!," she paused, we hadn't gotten as far as giving me a girl name, I hadn't asked Amy since I thought it would be all over in the few seconds it would have taken for my mom to see her own son, even dressed as a girl, Amy continued,

"This is Aleanne, she is an exchange student from Hong Kong"

Dave looked like a hungry wolf looking at a juicy steak,

"Hi my name is Dave, How are you Aleanne?"

"Hard luck Dave ha ha, she doesn't speak English" said Amy, before I gave the whole thing away with my less than girlie voice.

"How long is she staying here?" asked Dave.

Amy had a huge smile on her face, and said, "She will be staying at my place for a MONTH". "Anyway what are you doing here," 

Dave said, "I came over to see if Tom wanted to go swimming?" Does she have a boyfriend?

"Dave for goodness sake, you only just met her, give the girl a chance to settle in"

"Dave insisted, Well does she or doesn't she?"

"Not that I know of" "Where's Tom, do you know where he's gone?"

My best friend is hitting on me, What chance that my mom will see its me, her son, this looks bad, I've already fooled my friend, my BEST friend, and now he's asking if I'm free. OMG this is bad.

Just then I heard the front door open it was my mom, the time had come would she recognize me , would I be left to the descrestion of Amy's whims for a month.

"Hi Amy whose your friend?'' And with one foul swoop, I was totally in my girlfriends hands for a whole month.
Where will Amy take Tom/Aleanne? She has him for a month, she is a busy girl, where will she take him/her first?
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:iconcharlee718:
charlee718 Featured By Owner May 7, 2018
It sounds like Tom is going to be Amy's friend for a month that would be so much fun
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:iconsfc78767:
SFC78767 Featured By Owner May 9, 2018
Or maybe longer?
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:iconbluelakesitty123:
Bluelakesitty123 Featured By Owner Mar 6, 2018
Girls like dressing boys as girls. Minny Japan boys have rilly long hair , and now lezbeins in Japan want a third sex wird, not sissy , but sassy, 4 the male dawters of lezbeins ! 

If lezbeins  in space wanted a breeding coloney, with no boys, thay could razed males as girls , and declare male girls as real Wimin , so lezbein coloneys could be self substaining!

if boys are brave enough to go yo Skool as girls for 20 years , let them , 
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:iconjenniferliz1:
JenniferLiz1 Featured By Owner Jun 5, 2017
Should have know better.  I'm sure this will be a very interesting month, or more !
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:iconsfc78767:
SFC78767 Featured By Owner Jun 6, 2017
Maybe more you never know
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:iconcharlee718:
charlee718 Featured By Owner Mar 26, 2017
sounds like tom is in a panick
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:iconsfc78767:
SFC78767 Featured By Owner Mar 27, 2017
Yes its his first time as a girl
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:iconjaybird196:
Jaybird196 Featured By Owner Oct 7, 2016
Pretty girl :). I like Asian women. 

Let's see how this plays out.
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:iconsfc78767:
SFC78767 Featured By Owner Oct 7, 2016
Yes I find Asian men make great Asian women.
Reply
:iconjaybird196:
Jaybird196 Featured By Owner Oct 7, 2016
Well, a number of you have such delicate features. A favorite of mine is Ren, of K-pop fame. He, actually, did crossdress, and he was the most convincing!
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:iconsfc78767:
SFC78767 Featured By Owner Oct 7, 2016
Yeah it makes it easier if you can draw your own stuff, its hard to find a man in a dress online
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:iconjaybird196:
Jaybird196 Featured By Owner Oct 7, 2016
True. At least, a pleasant-looking one.
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:icondiverseauthor:
DiverseAuthor Featured By Owner May 31, 2016  Hobbyist Writer
This is Amazing!!!
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:iconsfc78767:
SFC78767 Featured By Owner Jun 1, 2016
Thanks that very kind of you.
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:iconcoag27:
coag27 Featured By Owner May 31, 2016
Hahaha! oh my gosh, i didn't realize this was a work of fiction at first. amazing! good work!
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:iconsfc78767:
SFC78767 Featured By Owner Jun 1, 2016
I wasn't expecting anyone to believe it, but thanks.
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:iconrichii06:
richii06 Featured By Owner May 31, 2016
I dont usually  comment but I cant wait to see where this goes 
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:iconsfc78767:
SFC78767 Featured By Owner May 31, 2016
It will go the usual route, but as in all my stories there will be a twist.
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:icontripx713:
tripx713 Featured By Owner May 31, 2016
this was a great story!
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:iconsfc78767:
SFC78767 Featured By Owner May 31, 2016
Thanks, how kind of you.
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:iconvanessaindressas:
vanessaindressas Featured By Owner May 31, 2016
Lovely start! Great to see you back!
A month? Like to see 'her' at the altar as a bride about to marry Dave (:
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:iconsfc78767:
SFC78767 Featured By Owner May 31, 2016
Yes been very busy with a friend.
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:iconqurion2:
Qurion2 Featured By Owner May 31, 2016  Hobbyist
Thank you! That lifted up my mood somehow.
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:iconsfc78767:
SFC78767 Featured By Owner May 31, 2016
So happy to help with your mood, but there will be a twist at the end.
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:iconlovelatex64:
LoveLatex64 Featured By Owner May 30, 2016
Lovely! This is the start of a series I hope? Can't wait to see where this is going 😄
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:iconsfc78767:
SFC78767 Featured By Owner May 31, 2016
I take suggestions if your willing, ha ha
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:iconlovelatex64:
LoveLatex64 Featured By Owner May 31, 2016
Hehe... Hope you will consider her in traditional Chinese dress when she goes out with Dave.
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:iconsfc78767:
SFC78767 Featured By Owner Jun 1, 2016
Don't jump the gun, but, Have you been reading my mind?
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:iconlovelatex64:
LoveLatex64 Featured By Owner Jun 1, 2016
Lol! I'd love to 😉😘
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:iconsfc78767:
SFC78767 Featured By Owner Jun 1, 2016
Long way to go.
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:iconlovelatex64:
LoveLatex64 Featured By Owner Jun 1, 2016
Don't tell me... 30 days?
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:iconsfc78767:
SFC78767 Featured By Owner Jun 1, 2016
So you are a mind reader, lol.
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(1 Reply)
:iconjohnfromjersey:
JohnFromJersey Featured By Owner May 30, 2016
Great story...  So where are all these girls who make bets like that??
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:iconsfc78767:
SFC78767 Featured By Owner May 31, 2016
In your dreams John, In your dreams.
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:iconjohnfromjersey:
JohnFromJersey Featured By Owner May 31, 2016
Sadly, yes
Reply
:iconsfc78767:
SFC78767 Featured By Owner May 31, 2016
Ha ha
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:iconchalkartist1216:
ChalkArtist1216 Featured By Owner May 30, 2016  Hobbyist Traditional Artist
Good start to what sound like a great story!
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:iconsfc78767:
SFC78767 Featured By Owner May 31, 2016
Thanks for the comment/feedback.
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:iconchalkartist1216:
ChalkArtist1216 Featured By Owner May 31, 2016  Hobbyist Traditional Artist
It was my pleasure!  :)
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:iconsfc78767:
SFC78767 Featured By Owner May 31, 2016
It's nice to have friends like you.
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:iconchalkartist1216:
ChalkArtist1216 Featured By Owner May 31, 2016  Hobbyist Traditional Artist
Aww, well thank you.  :)   Same here!  :D
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