Blackmail Saga

Lying about on my desk was a key, a sheet of paper and black lace garter belt, sheer black stockings and a very sheer black (and extremely skimpy) teddy; something like you'd expect to find in a Frederick's catalog – I knew this, because one of those catalogs came to my apartment every month or so. Jimmy had ordered the catalogue online in my name; no doubt, hoping I'd be inspired.

The sheet of instructions informed me that I was to go to an address printed at the top of the page – the key was for that apartment. I was to wear the 'clothes' provided, such as they were, and nothing else. Except, I could wear an overcoat until I arrived at the apartment. However, I was to shed the coat at the front door and enter the living room clad only in the get-up that the asshole, Ted, had provided. I was to wear an excessive amount of dark makeup and pure red lipstick; the missive Ted had written explicitly provided that I was to look like a 'street whore.' Last, I was to wear four inch, or higher, high heels; they had to be black.

"My god! I can't do this." I said aloud when I'd finished reading the instructions. I looked at my watch; it was nearly six thirty. I knew Jimmy would be getting home from work before I would; even if I left right away. There was no way I could go home and get ready for Ted's sick scheme without Jimmy knowing something weird was up.

I called Jimmy's cell and thankfully got his voice mail. I left him a message that there was a something going on at work and I would be home late; likely very late and for him to not wait up if I didn't make it home by bedtime. I had no idea how long Ted would keep me, but I was sure I had not been invited for tea and cake.

Next, I had to figure out how to prepare for Ted's demented assignation. First, I would have to go to the mall and buy shoes; I didn't even own a pair of four inch heels.

Hell, what sensible girl does? I thought.

I would also need to buy make-up, even at home I didn't think I had what I needed to comply with the instructions, if fact, I wasn't even sure I knew how to make myself look like a street whore. I also needed a lightweight overcoat; even though I had one a home. But, I was not going anywhere near the apartment, let alone to get my coat. Given the eight o'clock deadline and the fact that the address he gave was across town, I realized I'd have to hurry. I still had no idea where I'd go to change into his lewd costume; I would just have to deal with that later.

Fortunately, there was mall about five miles from the office and I knew there was a Frederick's of Hollywood store there; I had no idea where else I could find the sort of shoes I knew he wanted me to wear. Normal shoe stores don't carry such trash. The girl who waited on me was very helpful and kept giving me 'knowing' looks.

"It's a surprise for my husband." I finally felt compelled to explain.

I left the store with five inch heels; the only thing they had in stock in my size that met Ted's criteria. When I walked in them I felt like I was going to fall over; I have no heels over about three inches in my closet. They also hurt my feet; my toes were so crammed together by the obscene angle they entered the shoe, and gravity.

Next, I hurried to a department store and found the cheapest overcoat they had in my size – it still cost me over a hundred dollars – and then went to the cosmetic counter for makeup. I even asked the girl for advice; I told her my husband was dragging me to a costume party and I had to look like a 'tramp.' I think she was offended; you know, because I seemed to be suggesting that she would know.

All in all, I spent several hundred dollars on Ted's insanity. I still had to change and put the make-up on and drive across town. I looked at my watch and I was afraid I was going to be late; having no other real option, I went to the mall restrooms and into the handicapped stall to change. Wearing my obscene heels and the overcoat, with the lingerie underneath, I'd stuffed my office clothes and shoes into one of the shopping bags. I then went to the mirrors and started applying too much makeup to my face. I put thick lines of black eyeliner on my lids, as well as, under my lower eyes lashes. Then I applied bright blue eye shadow, long fake eyelashes and heavy mascara; along with heavy black eyebrows that finished the 'look' except for the bright red lipstick. As I was doing my lips a bunch of women entered and as soon as they saw me I heard muffled sounds of astonishment and whispers in the background. I collected all my stuff, grabbed my purse, and ran from the ladies room as fast I could.

I still had to run the gauntlet of waking through the mall in my five inch stilettos, and wearing 'street whore' makeup, to get to the parking garage where I'd left my car. After passing dozens of alarmed and disapproving people, the thought occurred to me that I could have worn my office shoes to the car; but it was too late and so I persevered.

I drove as fast as I dared. I was sure that if I were stopped for speeding, I'd be taken downtown and booked as a prostitute. Of course, that was ridiculous, but such was my state of mind that night.

I arrived at the address Ted had given me and found an apartment building where I parked in the visitor area. It was a nice building but not particularly upscale. I rode up the elevator, thankfully alone, and found the apartment number I'd been given. Sure enough, the key fit the lock and I entered – three minutes late. There were hooks on the wall by the front and I removed my coat and hung it on one of the hooks. I walked into the living room expecting to find Ted waiting and maybe angry because I was late. Instead, there was no one there.

As soon as I entered, a cell phone sitting on the coffee table began to ring. I picked it up and looked at it, then flipped it open and put it to my ear. Before I could even say hello I heard Ted's voice.

"You're late – you came within seconds of being turned in, don't let it happen again, ever."

"Listen Ted, I'm sorry, I had to go to the mall and ..."

"Shut up and listen. First, outside of the office, you are to address me as 'sir' – you will never use my name, understood?"

"Yes, T... uh, I mean, sir." I stuttered.

"Next; in less than five minutes after I hang up, the door bell to the apartment will ring. You will answer it dressed as you are right now and greet the men who will be your guests for the evening. You will entertain them in whatever manner they choose; and I think you can guess what that will entail. If you refuse them anything, I will know; I have multiple cameras and microphones in every room and I am monitoring them as we speak. Got that?"

"Yes,"

"Yes, what?" He demanded.

"Yes, sir." I said, realizing at that moment that it was as much about control for Ted, as it was about sex.

"Before your guests arrive, you will go to the kitchen where you will find a well stocked bar. Select your favorite liquor; not wine, not beer – liquor. You will fill a whiskey glass with the liquor of your choice adding no mixers, and no more that two ice cubes, and you will make sure the drink is finished before the door bell rings. Remember, I am watching and my cell has the number for the police on speed dial. Also, before your guests leave, you will be sure to consume a minimum of three more full glasses of liquor; I want there to be the smell of alcohol on your breath. If you're smart you'll call a cab when you leave. Do you understand what I've just told you?"

"Yes, sir." I was on the verge of tears again.

"If you dare ruin your lovely makeup with tears, I ,will instantly hit my speed dial. Now, one last thing; you are to keep the cell phone you are holding with you every minute for the next two and a half months. I will give you instructions on this phone, and only on this phone. If you ever fail to answer, you know exactly what will happen. Acknowledge."

"Yes, sir, I understand, sir." I said, still unable to grasp the enormity of what was happening to me. I'd thought Ted was going to want to use me for his own sexual pleasure for a couple months; as loathsome as that was, I'd sort of come to the conclusion that it as something I could deal with until the ordeal was over. Then, I would quit my job and I would convince Jimmy we needed to move to another city; maybe on the west coast. Now, Ted had added a whole new dimension to the equation; not only was I to be his sex slave, but apparently, I was to be abused by whomever and whenever Ted's demonic whim decided.

And I was trapped. I could do nothing. I'd wasted precious seconds standing stunned in the living room coming to grips with what I had just fathomed from Ted's astonishing call. I went to the kitchen and found the booze. I pulled a bottle of bourbon off the shelf and poured a full glass as instructed and added two ice cubes. I took a long drink; draining nearly half the glass and almost choked. I coughed and sputtered; I was not accustomed to chugging my drinks, especially hard liquor which I rarely drank. In an act of defiance, I added two more ice cubes and took another long drink.

"I like my booze cold ... sir." I said aloud, and thought, so fuck you asshole – call the cops and see if I care.

I heard the doorbell ring and quickly downed the last of my drink. I felt tingly already as the warmth of the booze spread through me. I stumbled just a bit as I headed to answer the door. Whether it was from the booze on an empty stomach, or from the five inch heels; I didn't know, nor did I care.

I got to the door and opened it. My jaw dropped as I saw three very large men; they looked like they could be pro football players. Two were white and one was very black; I'd never dated a black man before, let alone had sex with one.

"Hello." I said meekly. "Won't you come in, please?"

"Wow, is she ever fuckin' hot!" One of the guys said as they entered the apartment. The black guy grabbed my ass very roughly as he went past.

"Now that's some nice shit, baby." He complimented me; a compliment I would gladly have died to avoid.

"Hey slut, get us somethin' to drink. What'a you got to drink around here? You got any dope?" The biggest white guy said.

I went into the kitchen and rattled off the considerable list of various types of booze available and they each replied with what they wanted.

"Got beer?" One yelled from the living room. I checked the fridge and found six different bands, from Millers to several European brands I'd never heard of. The guy in the living room was happy with Millers.

I found a serving tray and walked into the living room and served each man with his drink choice which left a glass of bourbon on the tray for me; drink number two.

The guys circled around me as I stood there in my five inch heels; it gave me some inkling of how Custer must have felt during his last hours on earth. They started touching me as they moved in, one fondled a breast, one squeezed an ass check, one even grabbed my pussy and squeezed me there sending an unwanted thrill coursing through my tummy. I took a long hit of my drink; I was getting the feeling I was going to need it, and more.

The black guy stopped in front of me and turned to stand squarely in front of me.

"On your knees bitch, and do me, right now." He commanded.

"Yeah, Roy, great idea ... as good an ice breaker for a party as I ever heard." One of the others said, laughing.

I took another long drink and set my glass on the table as I went to my knees.

"Come on baby, unzip me and pull it out, let's get this show on the road, bitch."

I undid his pants and reached in and was utterly shocked by the size of his dick. Wrapping my hand around it in order to pull out it of his pants, my fingers tips didn't even come close to meeting; not to mention it was easily over eight inches long. It might even have been closer to ten. All I knew was that I could not imagine something so large entering me; at the same time, I knew he was eventually going to do his best to make sure it did. I shuddered at the thought.

"Come on baby get it in that pretty mouth o' yours."

"It's too big, I don't think ..." I tried to say; but I was cut off by him shoving his monster between my lips and trusting the thing down my throat. I almost threw up all over his cock.

"See bitch, it ain't to big for ya." Roy said. The other guys thought it hilarious and they laughed.

Roy put his hands of the back of my head and started pulling my head into him. Each time I felt the tip of his monster hit the back of my throat, it felt like I was gagging and I was sure I would toss my cookies. He must have sensed just what my limits were, because he took me to the edge, but never over.

While Roy ingloriously fucked my face, I felt hands slip under my teddy and they started groping my breasts; other hands found the opening in my crotchless teddy and these fingers were soon inserted inside me. Again, to my extreme horror, it was quite clear to me that I was extremely wet with sexual excitement. In fact, with the huge black cock in my mouth and my breasts being mauled and with someone finger fucking me; I was getting very turned on.

How I could be feeling that way; actually enjoying such abuse? I wondered. Being turned on no less, by being forced to have sex, was completely beyond me.

Regardless, I moaned on Roy's mammoth cock.

"I'm gonna fuck the bitch, OK, Roy?"

"Yeah man, go ahead, she ain't ready for me yet, she gotta be stretched some first." Roy said, giving the go ahead to his buddy.

I felt my hips being pulled up from the floor so that I was on my hands and knees; still sucking Roy's monster as he continued to pump his big black cock into my face. I briefly felt a cock press against my opening and then came pain and burning as it rammed home. The pain quickly subsided as my slippery pussy juices rapidly coated the guy's cock. I guessed that he wasn't as big as Roy, but his was still the largest penis I had ever taken in my life; though that would so change when Roy took me.

Where did Ted find these guys? I thought, as the cock fucking my pussy started to generate overwhelmingly delicious sensations.

My god, I thought, I'm going to cum again just like in the office with that creep Ted. And I did.

With Roy's huge cock stuffing my mouth it wasn't very obvious to any of the guys, but I knew it and felt betrayed by my own body again. I'm being coerced to have sex for christ's sake, my mind screamed as I came down from my orgasmic high. But I didn't remain lucid for very long; fingers connected with my clit and another tidal wave of bliss sent me crashing onto orgasmic shores a second time. As I recovered, I felt hot cum filling me and heard the guy fucking me groan mightily.

"Aw shit! I wanted to hold out longer bit she's too fucking tight." He complained.

"That's OK dude, I'll fix that right now." Roy said and lay down on the carpet on his back. "Put her on top o' me, you guys."

"Shit! Let me finish my drink first!" I said, grabbing my glass and downing what was left; about a third of it.

"Hey, dude, go out and bring that bottle in here so we can keep her glass filled ... least we can do for the little slut." Roy said, and he laughed.

I felt hands grab me under my arm pits and they lifted me up until my hips were aligned with Roy's organic miniature ICBM sitting on his launch pad waiting to launch. The other guy lowered the 'payload' over Roy and set me down; too quickly as it happened, because the pain of Roy entering me so abruptly was so intense that I thought it could only have been matched by child birth. Something I hadn't had the pleasure of; and after being tortured by Roy's cock that night, I'm no longer sure I'm capable of.

Needless to say, I screamed. No, it wasn't an orgasm; it was a red hot fireplace poker seemingly rammed up inside my pussy.

"Hey slut, keep it down!" The guy behind me cautioned.

"Dude, cut the bitch some slack. She just been split apart by the biggest hunk o' meat she's ever had; it's gotta hurt, dude." Roy said, defending me in a sick sort of way.

"Give the bitch another big drink. That otta help 'er." Roy told his buddy.

Someone put a glass in my hand – my eyes were still squeezed shut from the pain. I put the glass to my lips and drained it; they didn't know I like ice and I didn't much care either at the time.

As the burning of the bourbon reached my tummy, the burning in my pussy subsided. Roy's hips started to move up into me; gently at first, thank god. As severe as the pain had been when Roy entered me, I was totally astonished when his cock started to elicit stirrings of pleasure inside me. I was feeling very woozy from all the booze; I was sure of that. And, maybe the bourbon also acted as a bit of an anesthetic, too, because as Roy increased the tempo of his thrusts, the waves of ecstasy building inside me rose proportionately. I was soon screaming with bliss over Roy's cock; how long it lasted, I have no clue. I only know my orgasm continued for a very long time and did not end until Roy's enormous cock spasmed inside me and pumped a gigantic amount of cum inside me. When Roy was done, I rolled off him and gave the coffee table a glancing blow with my head; it didn't hurt anything like that first insertion of Roy's cock.

"Ooooow, that's gotta hurt." One of the guys said. I had my hand on my head, but it really wasn't that bad.

"Hey, bitch, we was told you supposed to eat all the cum we pump inside ya. You didn't do Red's when he came in ya, but the guy said he'd be watchin' so you better start eatin' that big load I just pumped in ya." Roy told me.

Shit, I thought, what an absolute cretin that asshole Ted is!

"Hey, Roy, here's her glass; let her squat over it - all that thick white goop will drip in the glass and then she can drink it. That'd be real hot, man." Red suggested.

Oh thank you Red, you're such a fucking gentleman. I thought, as they pulled me up into a squatting position and one of them positioned my bourbon glass beneath me.

By the way, ever squat wearing five inch stilettos? It's not easy; they had to hold me up to keep me from falling over. Or maybe it was the booze; hard to say.

"Ok, now drink it all up." Roy said. I did; I had no choice. Then Red filled my glass with bourbon – the glass which was still coated with a thin film of Roy's cum.

"Wash it down, bitch." They all laughed and shouted at the good fun I was having. The cum added a certain 'tang' to the bourbon and I made a mental note to order it that way next time I was in a bar.

"Hey, dudes, you both had a turn, now it's my turn, but I wanna fuck her in the ass."

"Oh god! I've never ..."

"Well, well, Howie you gonna get to take the little slut's anal cherry!" They all laughed; and I was getting a little tired of being the brunt of their sadistic jokes.

"Red, go check out the medicine cabinet in the bathroom and see if there's any lube. Being her first time, ya gotta be gentle with the bitch." Roy advised.

"Yeah, big bottle o' the stuff." Red said as he came back. Roy positioned me on my hands and knees and I felt cold liquid hit my rosebud.

"Shit! It's cold." I complained.

"Oh baby, don't you worry, we gonna warm you up, huh Howie?" More laughter.

I felt one, then two, fingers inserted in my ass. I knew I had to try and relax those muscles as much as possible – I'd never been fucked in the ass before, but I'd read about it when Jimmy hinted once he might like to try it sometime, though I was greatly relieved when he seemed to forget about the whole idea.

Roy was manipulating my asshole and I knew he was doing me a favor. When he finally told Howie to go ahead and take my cherry, it didn't hurt all that much; I guess it helped that Howie was the shrimp of the group, cock-wise, that is.