Cathy was in her second year of college interning in the office where I worked. Short red hair, brown eyes, well muscled legs and ass, flat stomach and firm C sized breasts she nearly always displayed in low cut shirts and dresses.
I wasn't the only guy in the office interested in her and despite the fact she was out of my league I flirted and made tentative offers for nights out which she always gently turned down.
I figured I had a better shot than the forty and fifty year olds populating the office, having just finished college two years before. The only guy my age was Danny.
Danny was the boss's nephew and ever since he had started work in the office all of the credit for my hard work went to that asshole. Danny had a hot Latino girlfriend named Monica that I had seen at the last company Christmas party. She'd worn a tight red dress with a slit up to her hip and had all the eyes of the guys in the company on her all night.
After a couple of months I had given up on Cathy, she seemed uninterested in anyone in the office. Then the last Friday of October she knocked on the wall of my cubicle.
" Hey David!" She said with a smile that as I spun in my chair to face her, caused my cock to twitch.
" Hey Cathy, what's up?" I asked.
" Nothing much, I was just wondering, one of my college friends is having a Halloween party Saturday, wondered if you'd want to go?"
" Sure." I said with a smile trying to keep from sounding too eager. Even if this were only friendly for Cathy there would be plenty of hot chicks to see I was sure.
" It's a costume party, everyone has to wear a costume. Are you alright with that?"
" No problem, should I go as something in particular?"
" Most of the guys I know are going as classic movie monsters... I think the Wolfman is hot! So animalistic!" Cathy breathed out the last phases that caused my cock to harden instantly.
" Then Wolfman it is." I answered with a big feral grin trying to seem more animal like.
" Perfect! Meet me there, here are directions," Cathy handed me a sheet of paper with directions scribbled on it. " I'll be Catwoman. Nine o'clock, see you there!" Cathy says with a smile, before she turned to go.
I shot out of the office as soon as five o'clock rolled around. I flew to the nearest costume store and picked out the appropriate costume pieces. Fury-hand gloves, fake fur to fill in my nearly bare chest, and a Wolfman mask from the store, a pair of torn pants and a torn shirt from home would complete the look.
I could barely wait for the time to leave and had to keep myself distracted all Saturday until I could excuse myself for pulling on my costume. Then I hopped in my car and followed the directions.
The correct house was hard to miss; cars were parked filling the driveway and both sides of the street. I found a spot on an adjacent street to park and walked up to the door.
Just as I was about to ring the doorbell Catwoman greeted me.
" There you are!" An excited voice said from behind a cat mask. " Monica is in the pool area."
The music was pounding through out the house; I was wondering how a student could afford to stay in such a place as I was dragged up a set of stairs. I was pulled into a room with glow sticks hung around it, barely illuminating it.
Catwoman suddenly closed the door and pounced me pushing me back on the bed.
" I'm so fucking hot!" Catwoman said as she yanked at my pants.
Before I even had a chance to realize what was going on, she had my cock out and free. She immediately took my hardening cock into her mouth, and the things her tongue was doing reduced me to animalistic groans before I could say anything.
I just laid back and enjoyed the sensations Cathy was inducing in me, and faster than any woman had ever brought me off I felt the cum boiling up my balls and shooting through my shaft down her throat.
As I breathed deeply trying to recover I suddenly felt something shoved in my mouth. As I was still wrapping my mind around that both my hands were handcuffed to the headboard above me.
Effectively cuffed and gagged the lights were turned on dazing me for a moment.
There were three women standing at the foot looking down at me disdainfully. There was Catwoman who had just given me an amazing blowjob; there was a girl in an angel costume I didn't recognize, and one in a devil outfit that I recognized as Danny's girlfriend Monica.
" You fucking cheating bastard!" Monica yelled at me angrily. " You are such an asshole Danny!"
I tried to mumble around the gagging ball in my mouth my name; to say I wasn't Danny, anything, but nothing I tried to say came out understandable. I knew I was in trouble.
" I couldn't believe when Tami told me you had been hitting on her, so we set this up. Tami telling you she'd be Catwoman so you would tell her you were Wolfman. Then you came right in, and let her suck you off, you bastard!" Monica yelled.
I didn't know what to do, I could not defend myself, and I wasn't cheating on anyone! Let alone this hot Latino that I would die to have a chance with. I was pissed off at that asshole Danny. How the fuck did I keep ending up with his shit!
" Well we are going to punish you so that this is mistake you won't repeat ever again." Monica said with a sadistic grin.
The Angel, dark haired fair skinned vixen held up a box. She began pulling out various items in the box, which I couldn't see very clearly.
The Angel and Monica then each grabbed one of my legs and pulled them back over my head. With a click my legs were cuffed to the top of the headboard with some straps that held them up and spread.
The position is not one I would call comfortable, but it hurt less than I would have expected. The problem being of course I went from being quite helpless to being completely helpless and entirely vulnerable.
Catwoman removed her mask revealing an Asian face. The Asian girl, Tami, began setting up a video camera, and soon the red light was on recording my situation.
Another moment and I felt something cool pour down my ass crack. Realizing what was about to be my fate I started to try and yell and shake my head in refusal. This only elicited laughs from my captors.
" What Danny? Not was willing to take as you are to give?" Monica asked cruelly as she approached me.
Suddenly I felt something being pushed against my anus. In an instant it popped in and I screamed into the gag. It felt as if I were being ripped apart.
" Don't cry yet, Danny. That was only a medium sized plug, we are going to get the large one in you before we are done." Monica said with another laugh.
Then I felt a sharp sting on my ass cheeks as I was lashed with something, a whip I presumed. Time and time again I felt my ass punished with the sharp bite of it until it all faded into a dull fog of pain that didn't really hurt that much anymore.
Then the plug was pulled from my ass and the emptiness left behind was its own torture as much as it was a relief.
Monica stepped around wearing a strap-on that must have been nearly 8 inches long and an inch or inch and a half thick.
" If I didn't have to keep that gag in your mouth to keep you from yelling I would make you suck this like a little cock whore. I guess I'm going to have to settle for your next to virgin ass."
With that Monica came up on the bed, and I could feel her line the head of the cock up with my ass, then she pushed in. I felt filled and tight before she had gotten more than a little in me, but relentlessly she kept pushing in.
I began to yell again with my throat feeling raw, but still she pushed forward until her thighs touched the back of mine.
I was horrified to find my cock had hardened up during this, and even now was leaking pre-cum. This did not escape notice.
" Hey look Mon! He's getting off on this!" Tami said pointing, to my distinct embarrassment.
Monica looked down and as she pulled out and thrust back in looked angrier. " You fucking asshole! I've never seen your cock get that large! You are a fucking ass whore aren't you?!"
