A slender male decides to win $200 for dressing as a girl for a day.
"Dude, I'm telling you, if you grow a beard,
no one will mistake you for a girl. It's that
long ass hair." John Said.
"Yeah, but I don't want a beard." I told him.
My hair is almost to the middle of my
back, it's black and straight. Apparently I
look like a flat chested girl, because
everyone calls me a lady. And, not to
tease, people who don't know me just
make a mistake.
"Alright Seth, but seriously... All you have
to do is put on a padded bra and a dress
and you're a chick." John said laughing.
"Fuck you, man. Even if I dress like a girl,
I'm more of a man than you are." I said
hitting his chest with the back side of my
hand and laughing.
"What the fuck ever, bro." We were both
laughing. "I bet you 50 bucks that if your
skinny ass threw on your girls dress and
walked the street, nobody would suspect
a thing! I dare you to, haha!"
"50 bucks, huh?" I said thinking it over.
"Make it a hundred and I'll fuckin do it." I
said, knowing he wouldn't put up a
"Alright." He said, and I stopped laughing.
"Do it, and I'll pay you a hundred bucks.
But, you gotta wear it for an entire day."
"Man, an entire day?" I said kinda bummed.
"Hey..." Tyler jumped in. "If you wear it
for an entire day, I'll throw in an extra
hundred." He said waving it in front of my
I couldn't turn down $200 just to wear a
stupid dress. No one would know it was
me. I am a very good impression artist and
voice actor, that's actually what I do for
a living. I could make myself sound like a
"Fine." I said blankly, snatching the hundred
from Tyler. "I'll do it, just so you fags
shut up, everyone will know I'm a guy."
"Okay, but we also have to see you do it."
John said, handing me his hundred in 20's.
"No problem." I said. "But you can't tell
anybody else about this shit."
"We won't, don't worry." Tyler said
starting to laugh.
The next day, at 6am before my
girlfriend went to work, I told her about
"I need to borrow one of your dresser
for it, if that's alright." I said
"That's fine, but only a dress?" She
asked. "You're gonna be one ugly ass girl,
and everyone will know it's you in a dress."
Gabby said laughing quietly.
"What the hell else am I supposed to do?" I said to her sort of giggling.
"I don't know..." Gabby started. "Put on a
bra and stuff it, and wear my panties so
it keeps all your junk from swinging and
showing out the bottom."
"Well, I was thinking of using a long dress,
and my shit doesn't swing that low." I told
"I only have above-the-knee high sun
dresses unpacked, the rest are in boxes in
the basement." She explained. "Just do
what I tell you, it'll be fine. And, we'll dye
your hair a light brown, we can dye it
"Dye my hair?" I asked skeptically.
"Do you want people to recognize you?"
She teased. "Because I promise, they will
if you have that hair."
"Fine." I gave in. I guess Gabby was right.
She dyed my hair a light brow color and
then curled it.
"I look like a girly headed fuck, already. Do I
need a dress?" I said, and she started
After my hair was done, Gabby painted
me with makeup. I even thought I looked
like a chick. I would probably fuck me.
Then, she put a bra on me, and stuffed it
with a fake breast implant she had for
testing. She said they were 38B.
When this was over, she gave me a light
red dress, almost pink, and white panties
to match the bra. I put on the panties,
and my dick was pressed up against me.
Gabby said I had a nice ass to be a girl, and
it fit perfectly inside her panties. I
slipped the dress over my head, and it
was tight around my fake boobs, and
stomach. Around my waist, it got loose,
and it hung around 4 inches above my
knees. This dress was really short. It had
no sleeves. I was a skinny guy, almost
hairless, and pretty tanned. My ass, back,
chest, and thighs were baby smooth.
"You have to wax your legs and arms, and
shave your face completely." Gabby told
And so I did. It hurt like a mother fucker,
but at least I didn't have too much hair.
"Okay, here." She said, handing me a pair
of flat, black shoes. "This is so you don't
have to walk in heels." She said smiling.
"But now you're ready to go, and you're a
pretty hot girl. I doubt John and Tyler will
know it's you. And, it's anti-smear
makeup, but don't cry or anything
because the mascara will run." Gabby told
me, but I never cry anyways.
Me and Gabby switched cars, since my
friends have never seen hers. I went over
to johns at around 3:20pm. I pulled up
into John's driveway, and they were
sitting on the porch. He gave Tyler a: "who
the hell is that?" look, and then I stepped
out of the car.
"Yeah, can I help you?" John called out.
I disguised my voice and said
"Mmhmm, I'm looking for um..." I paused
and look at my hand, as if something were
written their "Johnny Samuels?" I said in
a questioned form.
"Yeah, just John.." John said. "Who are
I undisguised my voice now.
"What up bud?" I said smiling.
"Holy shit... Seth?!" He exclaimed.
Tyler was dying on the right side of him. I
was laughing my ass off walking over to
"Dude!" Tyler screamed. "You are fucking
He was still cracking up so hard, I could
barely understand him.
"Yeah." I said laughing. "I just wanted a
dress, and Gabby did this shit."
"Jesus Christ, I can't even tell it's you."
John said laughing.
"Yeah, just needed you to see." I told
them. "I'm gonna go to the mall to see if
anyone I know is there."
When I got to the mall, I didn't see anyone
I recognized. I walked over to the
cushioned bench they have along the wall
and sat in the corner. I pulled my phone
out of one of the small pockets this
dress had, and started to text John. Some
guy walked up and sat next to me.
"Hey." He said.
I looked up and realized it was some guy
from my english class in college. I didn't
know him at all, so I wasn't going to risk
letting him know it was me.
"How are you, girl?" He asked, putting his right hand on my right shoulder.
"Fine." I said in my disguised voice, smiling.
The guy's name was Andrew, he had
short, dark brown hair, and bright blue
"You looked kinda lonely, so I wanted to
know if you'd like to come hang out with
us." Andrew said softly, and looked over
at two more of his friends at the table.
I knew the girl, Becca, but I didn't
recognize the other guy. Andrew slid his
hand to the middle of my upper back.
"Sure." I said, still smiling, and he stood up.
"Cool... Let's go." Andrew said, helping me
up off the bench.
I took his hand to be nice, even though it
was a little weird.
"You have soft hands." He said smiling.
Andrew's voice was so nice and gentle.
"Thank you." I said back to him, still
"I was going to text my friend to meet
me here, but now I guess it's fine." I said
when we got in earshot of the table.
"Yeah, just chill with us, it'll be fun."
Becca directed t'wards me.
"I'm Sami." I said to her.
"I'm Andrew, by the way." Andrew told
me, while we both sat at the table.
"And that's Tim."
"Hi." He said holding one hand up to wave,
"Hey." I said smiling back.
They were both pretty broad, a lot
bigger than me. Andrew was more
muscular than Tim, and had to be 6'5 tall. I
was only 5'8. Tim has shiny black hair that
reached over his ears, and was wearing all
black, except for his neon green shoes.
Andrew had on a red shirt, with blue
jeans. Becca had long blonde, straight hair
that reached her lower back. It really
stood out from her dark red shirt. She had
on a lacey white skirt, and knee high red
and white striped socks. I saw her light
brown eyes almost immediately, because
blondes don't normally have that. We all
talked and had a nice time at the mall. I
forgot I was even being a girl, I was just
having a fun time. We were there for
almost 4 hours. I got there around 4pm
and it was 8:47pm. It was pretty dark
out, and the mall was closing at 9. Becca
went home 5 minutes ago, and now we
were leaving. We exited in the back side
of the mall, since it was closer. We had to
walk In between the mall and another
shop sharing the same parking lot. It was
a long walk, and no one else was back
there. Andrew wrapped his arm around
my waist and kissed me on the side of my
neck. I pushed him away gently.
"Stop it." I said.
But I was unknowingly smiling because I
forgot I was a "girl." He stepped t'wards
me again, and pushed me with his
shoulder. I stumbled to the side a couple
steps, but I was laughing kind of quietly.
He wrapped his arm around my waist
again and pushed me up against the brick
wall. I was short and scrawny compared
to him, but that's why I made a convincing
girl. I put my hands on his chest and tried
to push him off, but I couldn't get any
leverage. He pressed his lips against mine,
and forced his tongue inside my mouth. It
rubbed against my tongue, and the roof
of my mouth. My entire body was against
the wall, so I couldn't pull away. Andrew
lifted me, and my knees ended up around
his waist. I felt his hard cock through his
I put my forearms on his shoulders and
tried to pull my mouth off of his. I finally
managed to get his mouth off mine.
"Ah.." I sighed. "Get off!" And Tim turned
He saw me pressed against the wall.
"Hey you two. Hold on for like five
minutes and get a room." He called down
"Stop!" I shouted, but Andrew and Tim
didn't seem to care.
"Tim, get outta here." Andrew said loudly.
"Oh, alright buddy." He replied laughing.
"Make sure she doesn't get away." And
then he walked away.
Andrew tried to kiss me again, but I
dodged my head to the side.
"Don't kiss me." I said. But, he did it anyways.
Then he started massaging my fake
breast, and I pulled his hand away.
"Stop touching me." I demanded.
But, Andrew continued. He reached down
and pulled the panties off a little ways,
only enough to expose my cock tip and
asshole. Andrew lifted my legs and my
ankles were just over his shoulders, and
the stayed there. My hole was wet with
sweat. He pulled me down and his cock slid
right into my asshole on the first try. I
screamed loudly in pain and tightened my
grasp on his forearms. Andrew started
bucking his hips back and forth, and
bouncing me up and down on his cock.
He put me down, but still had a hold on me.
He turned me and pushed my chest and
face against the wall. Andrew unhooked
his belt with one hand, and tied my hands
together, in front of me. He lifted my
dress over my ass. Then, I heard
footsteps. They were really close. And I
saw Tim coming back. I felt a thick warm
thing prod my asshole. It was Andrew's
cock. Andrew grabbed me on both sides
of my waist. He forced his cock into me,
deep. I took it all into my depths. It didn't
stop where it hurt to go into. Andrew ass
fucked me until my eyes started
watering. He pulled out and dropped me
to my hands and knees. Now Tim was in
front of me.
"Help." I pleaded.
"I'll help, don't worry." But I was worried
"I'll help you be a little slut." He said
unbuttoning his pants and getting on his
Tim tried to grab my head, but I jerked it
to the side. Then, he yanked me back into
position by my hair. I held my mouth shut
tight, but Tim slapped me really hard and
made me open my mouth. Right when I
did, he shove his cock in my mouth. I was
going to bite him, but he fucked my face,
going clear down my throat and back out
repeatedly. His balls were slapping me in
the chin. It was hard to breathe for a
while, but then I got a pattern. Drool was
running down my chin, and I felt strings of
it waving back and forth from the two
thrusting in me.
Tim was going fast, my mouth was wide
open and my tongue was hanging out.
Andrew was plowing my ass so hard that
it echoed when he hit me. It started to
feel good getting my asshole pounded so
nicely after about 10 minutes. And I didn't
mind getting my throat stretched either.
A few minutes passed the 10 minute
mark and both of them pressed into me
and didn't come back out. I felt Tim
shooting loads down my throat and into
my stomach. Andrew left a big pool of his
babies inside my asshole. Tim slid out
before he was done, leaving a line of jizz
trailing from inside my throat, along my
tongue to the tip, underneath my tongue,
over my teeth, and hanging in long strands
off my lips and chin. A huge sticky goop
of my slobber, along with smaller lines,
and long strands of cum were hanging
from my face. Tim lifted the huge goop
and rubbed it all over my face, first my
forehead. My mouth was still hanging open
with a cum trail to my throat on it.
Andrew yanked out a couple seconds
later. My asshole wouldn't close. Streams
of semen were pouring from my gaped
hole. I felt cum slipping down my throat
still, and some jizz dripping deeper into
my hole. I closed my mouth and swallowed.
Then I smiled at Tim when he smiled at
"Thanks." I said. "That was amazing."
Sitting up on only my knees and holding
out my hands to Andrew:
"Could you take this off now?" So he
took the belt off from around my wrists.
I stood up, still about 7 inches shorter
than Tim, 9 shorter than Andrew. Tim
rubbed some more of my goopy drool on
my face, and some lines of his cum. I still
had a ton of strings of drool and jizz
hanging off my chin. I smiled at him again.
Then I looked at Andrew.
"Thanks for the deposit in my ass."
I yanked my panties back over my ass as
the two walked away.
"By the way." Tim turned around. "You
were one of the best I've ever had."