Lesson Learned The Hard Way

Reader discretion is adviced, this story contain graphic content depicting violence and rape which may not be suitable to all readers. This is a fictional story and do not portray real events or real persons.

Friday afternoon arrived and I was called to Ross’s room.

I knew I was in for a rough night again, but there wasn’t anything I could do to stop it.

When I arrived at Ross’s room he was starting to set up the poker table, ready for tonight’s game.

Ross and I spent about an hour setting up.

When the room was ready he turned to me and said “time to prepare you”

I had no idea what that meant.

He ushered me into the bathroom and had me strip.

Then he proceeded to shave my hole.

“Can’t have a hairy arse on ya tonight. The guys will know you’re a dude as soon as they look at this black furry ring” Ross joked

When he was finally done he had me look at my shaved hole in the mirror.

While bent over looking at my hole he applied moisturiser to my freshly shaved hole, occasionally slipping a finger inside as he applied it.

Ross then presented a chastity device.

It was a fill pair of metal underwear, minus the rear end.

When fitted you couldn’t see I had a dick, only my exposed shaved hole.

Ross then filled my hole with a generous amount of lube and inserted a butt plug to hold it all inside.

As soon as he finished there was a knock at the door “coming” Ross yelled

“Better get your clothes on bitch” he chuckled as he walked towards the door.

I grabbed my pants and quickly pulled them on.

When the door opened in walked our three mates.

Jason quickly rushed me and said “glad you made it dude, Ross’s bitch will be here after the game tonight and we’re all gunna fuck her butt. It gunna be awesome”

We were all standing around chatting when Ross yelled “SHUT THE FUCK UP! Jesus! Anyone would think you’re all a bunch of women. Time to get our game on boys!”

We all sat down at the table and Ross said “rules for tonight are different than normal. As you all know my friends going to drop in later tonight, but she’s only expecting four guys.

I don’t want to piss her off so we need to eliminate one of you boys. The loser will go home to a solo night with their hand. The rest of us get our dicks wet in some bitches arse. If I lose, the person in second last goes home, she’s my bitch so get over it”

After a few rounds of poker I had won a few hands, winning by a decent margin.

Ross slipped a note to me under the table. It read:

‘You better start losing bitch. If you win none of the boys will be expecting to go home. If you lose you get to leave and return in the outfit I placed in my car and keep your secret safe. If you win I drag your arse out in front of everyone and rape your arse. Choice is yours’

FUCK…..!!

Now winning, but I needed to lose.

I needed to play this carefully, I don’t want anyone to know I threw the game.

Questions would be asked if anyone suspected that.

I wasn’t the type of person to bluff and the boys knew that.

So I needed to load up some bets on low hands and hope someone caught me out.

After a few more games I had lost half my chips.

“You’re not doing so well now Mark. Better pick up your game. You’re the only one who hasn’t had a piece of this slut” Jason joked

A few more losses, but also a few more wins under my belt and one of the boys was sitting in last.

The next hand he would need to go all in and I would need to lose against him or I was fucked.

He luckily ended up with two pair, aces and twos.

I ended up with two pair, twos and fours.

I was so relieved I lost that hand.

The boys were now calling for a break as they disappeared into the kitchen to grab dinks and chips.

While they were all gone, Ross leaned over and said “It’s time I stepped it up an notch”

I had no idea what he meant until the boys returned.

As I went to sip my beer my butt plug started to vibrate and it spat beer everywhere.

“You alright?” Jason asked as I fidgeted in my seat

“Yeah just choked” I said

From that point forward I couldn’t sit still.

The vibrating was intense and Ross kept changing the settings.

About an hour went by and Ross said “change of rules boys. She will be here in 30 minutes and we need to sort out our loser. The next hand decides the loser”

Shit….now everything was riding on this hand.

The cards were dealt out and I was so nervous when I turned them over.

Then instantly relieved when I saw low cards.

As we looked around the table it was apparent that I had lost.

“Sorry dude, you miss out again” Jason laughed

“Don’t worry Jason, Mark will be getting plenty tonight. Didn’t he tell you” Ross said leaving a pause at the end

I panicked thinking Ross was about to reveal everything when he continued “Mark’s been getting plenty of action recently. I’m sure he will get some.

“Wow….you didn’t tell us that” Jason probed

“Time to go” Ross said as he pushed me out the door.

I walked to his car and pulled out a bag of clothes.

Inside was a pair of tight jeans with a hole cut in the arse also a pair of women’s black boots.

There was also a note that read ‘you have fifteen minutes to get dressed and back to my room. Knock four times so I know it’s you’

I struggled to pull the super tight jeans over my legs and butt. After about five minutes of pulling and tugging I got them on. Then I slipped the boots on.

Looking at myself I looked like a woman, with big legs, from the waist down.

Ready I walked back to Ross’s room and knocked four times.

There was a bit of noise inside before the door opened.

Standing in front of me was Ross.

“They will know it’s me without something to cover my top half” I said

“Get inside slut. The boys are all in the bathroom waiting for me to get you ready” Ross said before smacking my exposed vibrating arse

I jumped from the shock and moved inside.

Ross then moved me to the lounge and bent me over the side, tying me down.

He then placed a box over me.

It had been cut out to cover my whole upper body.

Inside the box it was dark.

The only holes were small air holes poked in the sides.

“Time for the main event boys” Ross yelled as they all came rushing out of the bathroom.

“Fuck Ross this bitch has a damn sexy arse and she’s already full” one of the guys said as he tapped on the vibrating plug

Ross then chucked the remote around as they all played with the plugs vibrating settings.

Small moans escaped my mouth as they kept pressing buttons.

I was trying desperately to stay quiet, but it was so hard.

“Who’s first” Jason asked

“Well she’s lubed up already, so first dick in gets to cream the bitches hole first” Ross said

In an instant there was yelling pushing and lots of clothes being stripped off as all the boys attempted to get in first.

After only a few seconds the still vibrating plug was torn from my tightly gripping hole.

The pain was so intense I could feel my butt muscles spasm from the shock.

Before I had time to recover a dick was crammed inside, all the way to the base in one shove.

I cried inside the box and the guys could hear me.

“Fuck dude the bitch is crying. Did you hurt her with your big cock” one guy joked

“This bitch loves it rough. Smash her hole” Ross said

Fuck Ross was a cunt.

Not only was he forcing me to whore out my hole he was encouraging them brutalise me.

The dick inside instantly picked up pace slamming in and out over and over as hard and fast as possible.

I thought I was going to be bleeding.

I wanted to beg them to slow down or stop but couldn’t.

After a few minutes of fucking the guy said “Here it comes slut” then his dick erupted inside me.

It was so hot and almost seemed to sooth my pounded hole.

“Next” he called as he pulled his dick out

Instantly it was replaced by another dick.

This one was big, real big.

It had to be at least ten inches long and was as fat as the butt plug.

“Oh god” I moaned as it slit deeper and deeper

“Fuck….did you hear that. She likes my big dick” he laughed

“You should have gone last, you’re going to wreck her for the rest of us” Jason said, clearly angry

When he stopped pushing in and his pubes rested in my crack I felt full to bursting.

My eyes must have been bulging out of my head.

“No chick ever takes all my dick in her pussy, I’m going to start fucking them in the butt” he said

As he started to drag his heavy meat out to the tip I thought he would take my insides with it.

Then he pushed the whole thing back inside.

Little squeaks came involuntarily from my mouth “ah…..eh…..oh” over and over.

“She sounds like a dog’s chew toy, squeaking on the end of your dick” Ross joked

A few strokes and the guy fucking me said “Fuck she’s tight around my dick. I’m gunna blow soon”

Sure enough his dick hosed down my insides, shooting over and over.

“Fuck the bitch is full, your cum’s leaking out around your dick” Jason said

I knew when he pulled out my hole would run like a waterfall.

I was full to bursting and it felt like it was going to star running from my nose if he came any more.

When he pulled out sure enough I felt torrents of cum run out.

“That’s fucking nasty, I’m outa here I don’t want to watch any more cum drip from this sluts gaping arse” one guy said

“I’m coming too” the guy who just pulled out said

Within a few minutes they were gone and Jason was fucking me.

“Her arse is so loose now” Jason complained

Jason was a constant complainer and it always pissed Ross off, and this was no exception.

“If you don’t like it fuck off” Ross said angrily

Jason fucked with long strokes pumping in and out over and over.

My battered hole still leaking around his dick.

“I’ll make you a deal” Ross said

“What’s the deal?” Jason quizzed

“Cream in her hole then I want you to lick all that cum out before I fuck her” Ross said

“Fuck no dude, that’s nasty. Why would you even say that” Jason said

“I don’t want to fuck a sloppy hole, that’s why. If you do it, I will let you fuck my bitch any time you want” Ross offered

“I’m not coming here to fuck some slut every time I want a shoot my load” Jason said still hammering my hole

I was so nervous, I knew Ross was up to something but didn’t know what.

“What if I show you her face, here tonight? Then you could fuck here any time you want without coming here. I would also give you her number so you can call her any time of the night” Ross added

“But I don’t want to eat some dudes load, that’s gross” Jason said

Ross was getting pissed off “Look Jason, you’re going to shove your tongue up her arse and eat it all out. It’s mostly going to be you’re cum anyway, the rest has already leaked onto the floor”

I had a suspicion Ross was setting him up, but I didn’t know why or what Ross would gain from this.

The room fell silent for a few minutes.

The only sound was my hole getting fucked.

“Fine I’ll do it, but only if you eat your load out her arse after you fuck her. I want us to be even. I don’t want you holding this over me and no telling anyone…..ever!” Jason added

Smart arse I thought

“No problem, I have done that before” Ross said cockily

“You serious” Jason asked

“Yep, it doesn’t taste great but sex is sex and when your girlfriend asks you to lick the cum from her snatch, you do it” Ross said

“Fuck I’m going to cum soon. You ready slut, I’m going to breed your hole. Here it comes….here it comes. AAAAAHHHHHHHhhhhhhh FUCK. Feel that blasting your insides slut. After tonight this holes going to be full of my cum…..permanently. Ready yourself to get fucked at least twice a day” Jason said between moans

Once his dick finished shooting he pulled out, my hole still hanging open and oozing with cum.

“On your knees and clean up your mess” Ross said pushing Jason down

“I’m not sure about this dude. It looks nasty” Jason said

“That’s why you need to clean up your mess. My dick aint going in that. Now get munching otherwise you’re not getting any more tail from her….ever” Ross barked

“Fuck dude this shits crazy” Jason said before starting to gingerly tonguing the cum from around my hole

When there was no cum left on the outside he said angrily “There it’s clean”

Ross walked up as fingers and jammed his fingers inside.

When he pulled them out he said “Not in there it isn’t. Now clean it properly. Get your tongue in deep” then he slapped his cum covered hand across Jason’s face.

I felt my cheeks being pulled apart and a tongue dart into my hole, probing around searching for cum.

“Squeeze it out for him” Ross said while patting my lower back.

I pushed too hard and cum squirted out of my hole and landed on Jason’s face.

Covered in the slime he stood up saying “Fuck you Ross I’m outa here. This is totally fucked up”

I could hear Jason walking towards the door.

“What’s fucked up Jason, is you’re going to come back and finish what you started. Then you will thank my slut for your creamy dinner. Otherwise this video gets sent to the boys”

Jason raced over to Ross’s phone seeing the video of him licking cum from my gaping hole.

The video also had a close up of the cum squirting from my hole onto his face.

“The video has already been uploaded to my secure online storage. Your fucked not Jason” Ross laughed

“Why are you doing this Ross, we’re supposed to be mates” Jason said

“The only reason we’re friends is because you are mates with Mark and he’s already fucked…..literally” Ross laughed as he lifted the box off exposing me to Jason

“Dude, you let us fuck you” Jason said

“I didn’t have any choice. Ross caught me steeling from work and was going to rat on me. If I lose this job I get kicked out of Uni” I sobbed

“Ross your fucking crazy” Jason yelled

“Maybe, but now I have myself two bitches. Now start cleaning his hole before you really piss me off” Ross said as he jammed Jason’s face between my cheeks

Jason started to cry as he started to realise he was powerless to stop Ross

For the first time Jason was knowingly licking another man’s hole and it was filled with not only his cum but that of two other men.

After a few minutes of licking Ross walked up beside Jason and rubbed his dick on the side of his face.

“Move back and I’ll help get all the cum out” Ross said

When Jason moved Ross slit his dick inside my hole pumping a few times then withdrew.

“Now rinse and repeat” Ross laughed as he pushed his wet dick against Jason’s lips

Jason sat defiant, refusing to open his mouth.

“’Your pissing me off” Ross said kicking Jason in the nuts

Jason collapsed in a heap clutching his swollen sack as Ross added “You won’t like me angry, so you better start behaving. Now get up”

When Jason didn’t move Ross pulled him off the ground by grabbing a fist full of his hair, then slammed his dick inside his screaming mouth instantly gagging him.

Ross then proceeded to fuck his throat until his dick was clean, then jammed back inside me.

“Please don’t, I can’t take it, your dicks too big” Jason begged as Ross moved his sloppy dick back to him again

“You best get used to it then” Ross said before slamming in again

I cried as I witnessed the demise of a good friend.

After another twenty dips in my hole and back into Jason’s mouth, Ross was happy my hole was empty.

“Now to finish me” off he said as he grabbed Jason’s head and furiously started fucking.

I could see Jason was clearly struggling as tears streamed down his face and snot ran from his nose. “Slow down Ross you’re going to kill him” I pleaded as I watched Jason trying to escape.

I could see in his eyes, begging for help.

I thrashed against my bounds trying to get up but it was no use, I was tied down too tight.

I was watching Jason’s throat get smashed by Ross’s big dick over and over.

Ross pulled out yelling “bite my dick again and tie you up and I’ll fuck you in public toilet. Then leave you so the dirty old fags to rape you”

Gasping for air Jason said croakily “please Ross I can’t take any more”

“Your mouth or your arse? Make the choice. But either way I am not letting you go until I have finished” Ross said

Then Jason crawled over to Ross and took his dick into his mouth, but Ross pulled back.

“I want to hear you beg for it” Ross laughed

“Please use my mouth” Jason croaked

“I can’t hear you bitch, speak louder. Where do you want me to rape you?” Ross commanded

Jason yelled through sobs “Please rape my mou…”

Before he even finished saying it Ross slammed in deep holding Jason’s nose in his pubes.

Jason thrashed on the end of Ross’s dick almost turning purple before he was let up.

Then Ross repeatedly impaled Jason again and again.

“That’s it slut….I’m almost there” Ross moaned

Another four or five thrusts and Ross shot into Jason’s mouth.

“Swallow it. I don’t want to see one drop outside your mouth” Ross ordered

I could see Jason swallowing over and over.

Ross must have shot a huge load.

When Ross pulled out he said “welcome to the club fag” then disappeared into the bath room.

Jason quickly started to untie me, “we need to get outa here” he croaked

“We can’t he’ll ruin us” I said defeated

When Ross returned he ordered us into his bed telling Jason he expected to wake up with his dick inside his mouth. Poor Jason was going through what I had already.