Date: Sat, 14 Mar 2020 11:27:24 +0000
From: whipped@protonmail.com
Subject: A Dare and the Frat House

Category:

HS/College. It is about a straight high school boy who dresses up in drag
and goes to a frat party, only to wind up having sex with a jock he had
played pranks on in high school. No blackmail, nothing non-consensual. Just
weird situational sex.

This is a total work of fiction. All characters are over eighteen and you
must be over eighteen to read it.

If you like this story or others, consider donating to Nifty.

Feedback is always appreciated and you can find my other stories in the
author section under the name "Whipped."

A Dare and the Frat House

My friend Tommy and I were known for our dares.

In junior high, we had started with super mild stuff. Then, we started
streaking. Then, in high school, kind of crazy and sometimes dangerous
stuff became the norm.

Like, really crazy stuff.

He dared me once to strip to my underwear and handcuff myself to a tree in
the gay park. That could have gone really sideways, but all that happened
is a dude playing with my junk and then setting me free.

I think he could tell I wasn't into it.

I dared him to climb the water tower and hang a sign that said Jared
Donnelly sucks big dicks.

It was super high, he almost got caught, and Donnelly would have beaten him
to a pulp.

We climbed crazy buildings and egged houses and cars and broke into houses
and caused chaos.

Some of the dares were less extreme and were just daily stuff. Slip a note
saying someone's girlfriend cheated on them or cellophane the teachers
lounge toilet.

Just pranks.

The only one we ever got in trouble for was changing the locks to the
school office. We were both suspended for three weeks.

Sudsing the school pool was pretty legendary, though, and I think everybody
knew it was us.

The reason all that matters is because these weren't just sudden
dares. Sometimes, they required planning and prepping and days of work.

So, while I knew this dare was crazy, I didn't really expect anything bad
to happen or go wrong.

I stood outside the frat house for about ten minutes. The dare was super
clear. I had to get into the party, walk the entire downstairs, walk the
upstairs, and then leave.

The catch was:

A: I was dressed as a girl.

B: I had to offer any guy who talked to me a blowjob.

Now, I didn't actually have to go down on anybody. I just had to offer to
suck their dick if they talked to me. I also didn't have to go into the
bathrooms, so I could leave as soon as I checked out the bedrooms and the
living rooms and kitchen.

I figured I could keep my head down and be in and out in ten minutes,
easy. Just a quick speed run.

I looked enough like a girl in all this stuff I could probably get away
with it. Tommy's sister was a cheerleader in Iowa and had left her
uniform. The frat party theme was Jocks and Sluts so it worked perfect.

My hair was short, but I had on a wig we bought at a garage sale. It was
curly and long and blondish brown and actually felt like people hair.

Tommy had used some of her makeup on me and helped me shave my body top to
bottom.

I didn't look pretty and it was hard to walk in the heels, but I mean I
didn't shout trannie or anything.

I guess the fact I was only 5'8 and skinny helped.  I almost made it out,
too.

The last bedroom was upstairs and the lights were off.

I walked in, checked it out, and heard the door push shut and a lock turn.

I turned and saw Jared Donnelly.

Blocking the door.

Jared Donnelly had had it out for us ever since the water tower prank. He
couldn't prove it was us, but he had made it clear if he ever found out it
was we were dead.

And he could kill us.

I was toned and everything, but his hand could wrap around my thighs. He
had gotten a rugby scholarship or he wouldn't be in college.

Jared Donnelly was HUGE.

Right now, his 6'5 and 250 pound ass was clearly drunk. His brown hair was
in his eyes and they were super bleary looking. He was holding a beer and
wearing nothing, but a jock strap. I hadn't been hairy even before I
shaved, but he had hair everywhere. Not just pits and a happy trail, but
all over. He had probably shaved before the party and I could already see a
five o clock shadow.

He growled at me, "Get over here."

I thought about running, but there was nowhere to go.

I walked over to him expecting violence and looked up. Then he grabbed my
ass and kissed me.

I could taste the alcohol on his breath. His tongue shoved itself deep in
my mouth like it was trying to go down my throat. I could feel the stubble
on his lips.

Part of me wanted to throw up or cry. The rest was in shock.

When he finally pulled his tongue out of my mouth and let go of my ass, he
spoke again.

He looked down at me and said:

The only reason an ugly slut like you comes to a party like this alone or
wanders off into a bedroom alone is because she wants dick. I'm just drunk
enough, baby, that I can fuck you real good, no matter how ugly you
are. Hell, if you do a good job I can probably get my buddies to pound your
pussy too.

Then he reached for my skirt and started trying to pull it down and said,
"Let me eat that pussy till you're real wet, baby. "

I froze. If the skirt came off, he might see the outline of my dick in the
leggings. If he tried to eat me out, he would definitely see it. If he
found out it was me and he just made out with a guy, who knows what he and
his frat brothers would do.

And then it happened, almost on autopilot.

I whispered, "Can I give you a blowjob instead?"

He didn't answer.

He just shoved down on my shoulders, until I was on my knees in front of
him.

And then the jockstrap was off him and his dick was in my face.

I stared at his hairy balls for a second before his dick fully
registered. His nuts were twice the size of mine.

His dick, though, was a monster.

He wasn't circumcised and even soft he had to be seven inches. He was
thick, too. I had never been this close to someone's else's cock and I
guess that made it seem even bigger.

Then I felt his fingers pry open my lips and his other hand feed his dick
into my mouth.

I gagged the second it hit the back of my throat.

He slapped me gently with his hand across my face when I pulled off and
then he tried to force it deeper again.

This time, I retched pretty loudly.

He gripped my head by the back of my wig and pulled it back so I was
looking up at him from my knees.

Then he said, "I ain't trying to be hateful, babydoll, but you can either
learn to deepthroat on your own or I can invite some buddies in to teach
you while I tear your pussy up."

This time, I didn't pull off.

If girls could deepthroat, why couldn't I? It couldn't be that hard.

I grabbed his ass for balance and forced his dick into my throat. My throat
started convulsing and trying to eject his dick and I just kept swallowing
until it relaxed and I realized something.

His dick was in my throat. All of it.

He was hard and his dick was buried to the balls in my throat. My lips were
mashed against his balls.

He held my head down until I thought I was going to pass out. I started
pounding on his butt, but it was so firm I don't even know if he felt or
heard it.

It was like hitting a brick wall.

Then he let go of my head.

And did it again.

And again.

And again.

I could feel my whole face turn sloppy as my throat opened and he started
to just pound it while I knelt and took it.

Then he lifted me up into his arms and brought me to the bed. He threw me
down on it on my stomach and pulled my legs down until they were off the
edge. I had a moment of total panic.

He sort of slurred, "Are you on birth control? I need to fuck."

I shook my head. I figured that was it and then he reached under the skirt
and slid my leggings down.

I was naked under them. I felt the air hit my cock and balls and panicked.

He brought his face close to me and said, "I don't have a condom, so I have
to assfuck you. I'll try and be gentle, but I'm drunk as fuck. Guide me in,
ok, baby."

He started petting my hair and I realized this was another moment. I could
get up and run out or tell him the truth or take it and hope nobody found
out.

All I had to do was say, "Stop."

I reached for his dick and brought it to my hole. It felt too big. I knew
this wouldn't work.

Then he shoved it in.

I felt an instant of incredible pain and I think I screamed into his hand.

Then I passed out.

I woke up to him deep inside me. I couldn't tell if I was unconscious for
five minutes or hours.

It felt like his whole weight was on top of me. His arm was around my
throat and I could smell his pits and sweat. His legs were wrapped around
mine too and his sweat was drenching the cheerleader dress and dripping on
my face.

I could feel his dick balls deep inside me. It felt like a crowbar shoved
up my ass, but on top of all the pain was this super intense feeling I
couldn't explain.

It was like his cock was punishing me, but also making my dick leak. Every
stroke, a little precum gushed out of my dick.

Then he pounded the right spot and I almost came.

I didn't have time to figure anything out, though. The second he realized I
was awake again, he spoke.

He told someone, "Bitch woke up. Try her throat, at least until I creampie
her ass."

Then I felt the bed creak. I looked up and a Hispanic guy was laying
back. He had dark brown skin, coal black eyes, and was just wearing soccer
shorts. He lifted his legs, pulled the shorts down, and threw them off the
bed.

His dick was already hard and I knew what to do.  I wrapped my lips around
his dickhead, licked the piss slit, and then took him to the balls.

He wasn't like Donnelly. Donnelly was just grunting and groaning and
fucking me.

This guy was talking dirty the whole time, saying things like:

Deepthroat that shit.... lick my balls Mami...you gotta work it if you want
me to shoot that shit in your mouth, baby.. you want that dick snot
flooding your tonsils don't you slut..gag on that big Latin dick you white
bitch...

My mind almost turned off. Then I realized something.

My dick was hard. Really hard. The hardest it maybe ever had been.

I wasn't sure if it was just the fucking or the grunting or the dirty talk
or the dick in my mouth too, but something was turning me on more than I
ever had been before.

I embraced the moment. I took the guy's dick in my mouth so deep I could
lick his balls. And I did, even as I gagged and choked.

I started pressing my butt up into Donnelly and his cock. I felt him
hitting the spot over and over and wiggled as he did to get it deeper.

Then I nutted.

My dick exploded and my whole ass shook and started squeezing Donnelly's
dick as I came. I felt him shake and then I felt him get bigger inside
me. He thrust so hard then it knocked the breath out of me. All I could do
was lay still as his balls unloaded up my ass.

The guy in my mouth wasted no time. He was jacking the base of his cock
while Donnelly was shooting and his dick throbbed and pulsed one load and
then another in my mouth. His cum tasted slimy and a little bitter, but it
wasn't as gross as I expected.

I tried to lift my head up and he held it down.

He looked at me and said, "You ain't done, baby girl, until you suck all
that nut up."

I looked at his junk. There were clumps of jizz in his pubes and milky cum
running down the side of his dick and his nuts. There was even globs on his
stomach.

I knew what he wanted. I brought my mouth back down and sucked and licked
it all up.

Donnelly pulled out of and off me while I was cleaning up his friend.

He slapped my ass hard and I felt it quivering.

Then he slurred, "Tell Tommy we're good now. I just expected pictures, not
ass. And either get out of here or expect a lot more dick."

Then he reached and grabbed my dick. It was soaking wet with cum and he
jerked it for a second.

He growled, "Fucking faggot."

Then he just left.

I laid there as the Hispanic guy stood up and got dressed. I watched him
slip on a shirt, his underwear, and put his shorts back on.

He smiled real big and said, "Pussy is pussy and a mouth is a mouth,
maricon, but unless you want about ten frat boys tearing up your boy cunt,
you need to get up and get the fuck out of here."

I tried standing and almost fell. Then I realized.

Maybe it was better if I stayed?