Halloween Trick (M+/M-teen, 1st-gay exp, rp)
by Trickster (email@example.com)
Going in drag on Halloween proved to be a big mistake
when six guys give me the ride of my life.
had always heard that girls could drink with a fake ID
much quicker than a guy so I waited until Halloween to
put the theory to a test. Since I was only 17 and my
older sister was 22, I was sure that by using her
driver's license and a costume that covered my face
pretty good that I could pull it off.
Since I was on the swimming team I had a body that, when
clad in the harem costume, made me pass as a, albeit
flat-chested, girl. One thing I noticed when I put on
the costume was that I immediately got a hard on. I
jerked off but it did no good, I still had a hard on, so
I decided to use one of my mom's kotex's (I think she
used them because her "flow" was so heavy) to try and
cover the telltale sign.
There was a bar that I knew some girls at school always
got in pretty easily despite the fact they were underage
and I knew that they were having a Halloween party
When I arrived, I had no problem getting in with my
sister's driver's license. I could feel the eyes of the
guys on me as I went by and it felt cool. I was hoping
that Jenny, my girlfriend wasn't there ...and when I
looked around, it appeared that she wasn't. I knew that
she had bought a pirate's outfit and I didn't see one in
When I got to the bar I ordered a vodka and tonic as I
felt that went with the role best.
I hadn't had two sips of the drink when I felt a hand
rub my ass through the sheer nylon of the harem outfit.
I turned around and saw Mark Simpson smiling at me. At
first I thought he recognized me and my heart almost
stopped, but then he said. "Nice outfit, what's your
I moved a little away from him but he gripped the nylon
material and I thought it was going to rip, so I let him
pull me closer to him as he kept his hand on my ass.
"Ummmmm, Jenny," I said with as high pitched voice as I
could muster and pulling a name out of thin air.
I thought about punching him and running, but images of
police and handcuffs and laughing policemen discovering
who was under the costume prevented me.
Mark took my reluctance to pull away as encouragement
and slipped his fingers between the cheeks of my ass and
What happened next surprised me. I felt myself getting
hard against the kotex in my harem panties. I pressed
against the bar for fear that someone would see the
protrusion. In doing so I gave Mark further access to my
posterior and this only made him smile the more as he
took this as a further invitation.
He leaned over and whispered in my ear, "You have the
nicest ass I have seen in quite a while. What say we get
out of here?"
My mind raced for something to say and for the life of
me I could think of nothing to say to get him
disinterested. Finally, I heard the words, as if from a
stranger coming from my mouth. "You don't want to waste
your time on me tonight, I have my period."
From the look on his face, I thought that this stupid
blunder of a statement had worked, but I was wrong. He
just smiled and moved his fingers further into the crack
of my ass. He moved forward again and whispered in my
ear, "Oh, that's okay Jenny, there are lots of things we
My mind raced for something to say, but before the words
came out he said. "I'll be right back and then we can
Now was my chance. As soon as he turned to leave, I
fished in the little pocket of the panties that they
provide for almost nothing and pulled out a $20 bill and
waved it at the bartender to pay for my drink so I could
make a quick exit.
I turned to see if Mark had made it to the rest room as
yet and I saw him about thirty feet away talking to a
group of guys that also were not dressed in costume, but
that I didn't recognize. They were looking at me and
smiling. I started to get frantic and waved the bill at
the bartender who was busy making drinks for one of the
I finally got his attention and he took the $20 and went
to the register to ring up my tab. Every second seemed
like an hour before he came back with my change.
"You didn't have to do that," I heard Mark's voice over
my shoulder as I was taking the change from the
bartender, "I would have paid for your drink."
I turned around to see Mark standing there with five of
the guys that he had been talking to in the corner.
"I want you to meet a few of my friends, Rick, Tim,
Cliff, Dale and Gene. They have had a little too much to
drink so I promised them I would drop them off at Rick's
house which is just a couple of miles away from here."
I couldn't think of anything to say but let Mark guide
me out of the bar.
"Uh, how are we going to all fit into one vehicle?" I
asked trying to find an out.
"Oh, I've got a Dodge Ram 3500 van. There is plenty of
room for all of us."
"Yeah, I love the Ram." The one I think named Rick said.
The others laughed.
When we got to his van, I could see that it was not only
big enough for the six of us, but it could have fit
another 8 people in it. I climbed in the back and my
heart sunk as I saw the it looked more like a converted
RV then a van. There was a bed, a swivel chair, a TV and
"Where do you want to sit?" Mark asked me as he climbed
into the back of the van with me.
I quickly sat in the swivel chair.
The van started and I noticed that the one named Dale
"I thought they had all had too much to drink?" I said,
"why is he driving?"
"Oh, uh, Dale, uh, he hasn't had too much to drink."
"Well, then why didn't he drive them home in his car." I
asked, now starting to panic and I could feel my voice
starting to crack.
Mark smiled and put his hand on my leg as he sat down
next to the chair.
"You got me, honey," he said, "we just want to have a
little fun, that's all."
I looked at them as they leered at me. I could catch
Dale's smile in the rear view mirror.
"So why don't we just get comfortable," Mark said taking
off his shirt. The others started to do the same.
"Don't be shy," Mark said, "these windows are tinted so
dark no one will see in here. Believe me, this ain't the
first party we've had back here."
They all laughed.
"Come on," Mark said, but he wasn't smiling anymore.
My mind was racing. I knew that if they found out that
they had been tricked by a boy that they would hurt me
badly, if not kill me."
"Uh, I told you," I stammered, "I have my period. Please
let me go."
"Awwwww, she's begging," Mark laughed as he pulled off
his pants. He was wearing no underwear and his erection
stood out and looked to be about 7 inches. I looked
around the van and saw that each of them had stripped
naked and were sporting erections.
"You don't want to get blood all over your van do you?"
Mark stood in front of me with his erection only inches
from my face. I had never even had my cock sucked but I
had seen many porno movies. I could see from Mark's
expression that he was about to grab my hair and shove
his cock in my mouth and when he did that the wig would
definitely come off in his hands and I would be a dead
"Okay," I hear myself say, "I will suck each of you off
on one condition."
They all looked surprised but didn't answer.
"I keep my clothes on."
They all nodded their agreement in silence.
Before Mark could change his mind I took his erection in
my mouth and tried to remember everything that I had
seen in the movies. I gagged but managed to get about
half of it in my mouth. I think I was more afraid of
them finding out who I was then I was of sucking six
I closed my eyes and concentrated on getting Mark off as
soon as possible. I wrapped my hands around his naked
ass and found myself cupping his balls. I tried
everything that I had seen in the porno movies.
"Oh, fuck!" Mark yelled, "she is fucking great."
I wrapped my hand around half of his cock and jerked him
off while I sucked the top half. I could hear his
breathing getting heavier.
"Oh, fuck, here I come," Mark yelled, "swallow it,
The way he said it, I knew I had better swallow it.
He spurted and spurted into my mouth and I swallowed as
quickly as I could. I had eaten raw oysters once and it
reminded me of that, except not cold but hot. I just
kept telling myself that I was eating raw oysters.
"Man, that was fucking the best blow job I have had in
my life," Mark said as he collapsed on the floor.
"Me, next," the one named Rick said as he stepped in
front of me. His cock was only about 5 inches long and I
felt relieved. I found that when I started sucking him
that I could actually get it all in my mouth. I put both
my hands around his ass and started pumping my mouth on
his cock. In two minutes he was coming in my mouth and I
thought of another plate of oysters as I swallowed.
Cliff was next but he made me lie down on the floor on
my back which worried me but then he straddled my face
and started to face fuck me. He was also about 7 inches
so I had to wrap my hand around the base of his cock so
that he wouldn't choke me as he plunged his cock into my
As he was pumping into my mouth, I felt a hand rubbing
my ass and starting to make it's way between my lets. I
wanted Cliff to hurry and come so that I could stop the
person who was about to uncover who I really was. I
found myself doing something that I had seen in the
porno movie which surprised me. I stuck my index finger
up Cliff's ass. He came right then.
"Oh, shit," he said as he was coming, "oh, shit...no
chick has ever done that to me before."
As he climbed off, I saw that Gene was the one that had
been trying to put his hand inside my pants.
"Man, I want to fuck this whore," Gene said. I could see
the glare in his eyes and knew this was going to be a
I waited for Mark to come to my defense, but he was
quiet. They were all quiet, waiting to see what my
"I told you, I have my period," I said.
"I don't give a fuck," Gene said angrily.
I looked at Mark pleadingly.
"You want blood in your van?" I asked Mark.
Mark just smiled.
I felt the van pull off the road and come to a stop.
Dale came to the back of the van and started to remove
Gene pushed me back down on my back and started to
remove my pants.
"Okay," I said, "how about this," I gulped.
"How about if I bend over the chair, pull my pants
down... but not off... and you can... you can, uh..."
"I can what?" Gene snapped.
"You can fuck my ass," I murmured, lowering my eyes.
I saw Gene's jaw drop.
"Ok," he said quietly, almost in disbelief.
I got on the swivel chair and pulled my pants down,
petrified that they would fall too far and expose my
equipment despite the kotex.
I waited and I heard Gene spit. He rubbed the spit into
the crack of my ass and I felt his index finger enter my
anus. I gritted my teeth but it didn't hurt as much as I
anticipated it would. In fact as he started moving the
finger in and out, putting some more slobber on my hole,
I found it felt kind of good.
"Okay, bitch," Gene said leaving over me, "here it
I felt the tip of it inch in and thank God he did it
slow. In about 30 seconds I felt his stomach up against
my ass and I knew that he was in completely. I looked up
and saw everyone standing around sporting erections.
Gene started slowly and at first it hurt but after a few
minutes I found I was enjoying it. I closed my eyes and
when I opened them I saw Tim standing in front of me
with his cock at my face. I opened my mouth and he slid
his 6 inches into my mouth.
Suddenly I felt the most incredible orgasm building up
in my balls. The friction of the kotex rubbing up
against my cock together with Gene's cock, now, pounding
into my ass was enough to bring me off. For the first
time in my life I came without even touching myself. I
screamed, although it was muffled by Tim's cock that was
pumping into my mouth.
The sound of me coming was enough to bring Gene off and
I felt him spurt into my ass.
"Oh, shit," I heard him grunt as he unloaded.
Tim was just seconds behind him as I had another order
of oysters slip down my throat.
I was barely aware of Gene slipping out of me and Dale
slipping his cock into my ass as I was still panting
from the incredible orgasm that I had just had.
My ass must have been pretty well lubricated because
there was no pain whatsoever as Tim pumped into me. I
could feel myself getting another erection and was close
to coming when I felt Dale spurt into my ass.
"Shit," I heard Mark say, "this is too fucking hot. I
gotta have some of that ass."
I felt him slip easily into me and start pumping when I
heard Rick say, "Holy shit man! Look!"
I turned to see what everyone, with the exception of
Mark who was pumping away into me, was looking at. They
were all looking down between my legs. It was then that
I realized that in the excitement of my orgasm I had
lost concentration on keeping my harem pants around my
thighs. They had slipped down to my knees, the cum
filled kotex was laying on the chair and my balls were
flopping back and forth as Mark ploughed his cock into
Mark was oblivious to everything but his impending
orgasm and I felt him tense up as he spurted what felt
like a small amount of cum into my ass.
I saw the look of anger on the others face as they
realized that they had been fucking a boy instead of the
hot little teenage girl that they had thought.
"Move," Rick said, pushing Mark aside, as he brought his
fist back to hit me.
"Wait," Dale said, grabbing Rick's arm.
"What?" Rick asked, looking at him.
"Wait, a minute," Dale said, deep in thought.
Everyone looked at Dale and waited.
"Hey," I interjected, "I'm sorry. I swear I tried to get
out of this, but I didn't anyone in the bar knowing what
I had done and things just got out of hand."
"Yeah," Dale said, "but you liked it."
They all looked at me.
"No, no, I didn't," I stammered.
They all looked down at the cum filled kotex.
"Really?" Dale said.
I could feel my face turning red. I said nothing.
"Is that the first time you've ever been with a guy?"
I shook my head to the affirmative.
"Look, guys," Dale said, "I am not a faggot, but that
was the best blow job I have ever had."
"And the tightest ass I have ever had," Gene chimed in.
They were all quiet for a minute and I felt relief that
I wasn't going to get murdered.
"So now what?" Rick asked.
Mark moved to the front of the van and came back with a
"So now our little girl continues the party but has
nothing to be shy of now, right?"
I just nodded my head.
"Get back on the chair," Mark said.
I climbed back up with my, now bare ass, protruding.
"Who's next?" Mark asked as he held the camera to his
I felt my ass cheeks spread and an erection probing at
"Say cheese," Mark said as he snapped a picture.
"Hey don't get my face in that picture," I heard Gene
say from behind me.
"Don't worry," Mark said as he snapped another picture.
"This will just be used in case our little girlfriend,
Jenny, here decides she doesn't want to party with us
Tim came around to the front and started wiping the
makeup from my face so that my face would show up more
clearly in the photos.
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This story was written as an adult fantasy. The author
does not condone the described behavior in real life.