Annie Gets Blackmailed

by Anne Zvesteit

Part 3

 

So here I am, makeup in disarray, my lingerie and face covered in the dried cum of my office I.T. administrator. He raped my mouth and my ass last night, and I've got a date with him later today. God only knows what he has planned. But until I get that picture back from him, I have to play his game.

I'm late for work, so I jump in the shower for a quick soak under the scalding water, wondering where this is all going. I've been dressing in women's clothes all my life, but suddenly, within the last 24 hours, I've become a cocksucker ("You're a natural", he said) and a doggy-style assfucked slut ("You're not forgetting that amazing orgasm, are you?", my mind taunts me).

Out of the shower and cleaned off, I dress in 100% men's clothes for work today. I don't need any extra stress of being found out.

I've got to fight this. Surely there's laws to protect blackmail victims like me. Maybe I can bring him up on charges and have the evidence sealed by the court. I'll do some research online at lunch and check it out.

Luckily or by design, I don't see my blackmailing tormenter all day. Not that that's unusual, but considering what he did to me last night I've come to expect anything.

Not only do I not find anything helpful (it's as if laws were written by lawyers so that only lawyers can understand them), but as I'm sitting at the computer my e-mail pops up with a message. Subject: Our Date Tonight. Shit, shit, shit.

Annie,

Had a great time last night. Be ready tonight at 7 sharp. Wear a purse.

D.

A purse? I don't have one! Doesn't he fucking know that I'm a closet case? I don't have a fucking purse!

Until now I've bought all my girl clothes and accessories online. I've only ever been out as a woman once, and that was only in a hotel corridor. I can't be seen in the local mall buying a purse, for God's sake. It's Friday and the mall will be packed. Everyone who knows me knows I'm divorced and don't date. If I'm spotted shopping for a purse it will raise questions I don't really want asked. In any case, I need one by 7 tonight. What the hell am I going to do?

Think, Annie, think.

Think. Annie. Think "Annie".

That's it. The bastard is not content to turn me into a sex object. He wants me to go shopping as a woman. He wants to humiliate me more than completely. He wants me to go to the local mall and see someone I know. Maybe even him. He's probably waiting there now. The bastard.

All right, think. There's no time to drive to the next town, and even if I did I can't bring myself to shop for a purse as myself. And there's no way in hell I'm going to go down to the brightly lit, busy mall as Annie.

Think, Annie, think.

I've been practicing my makeup, my walk, my voice, my mannerisms for years now. It's time for the final test. But not the mall. Too dangerous. There's a secondhand thrift store on the way home. I've never been there, and I'm guessing none of my circle of acquaintances has either. Dave didn't say it had to be a Prada purse.

I've got to leave work a little early. There is much to do.

Rushing home, I jump in the shower for a quick leg shave. Luckily I'm not hairy chested, so legs is about all I have to worry about besides my face. Looking at my unkempt bush of pubic hair, I wonder briefly whether I should shave it into a nice, trimmed triangle. No, I'm not ready to make that jump. But I do shave my ass, inside the butt cheeks and out. I never knew my ass was so hairy.

Sighing, I put on my fleshtone bra and falsies. My legs don't see enough sun to be passable by themselves, so I'm going to have to wear hose. Jesus, 30 years of crossdressing and I don't have a single pair of pantyhose instead of stockings and garter belt. Once again my panties drawer fails to yield a single pair that's not sexy. Oh, well, this pair of green string bikini panties will do. God, they feel good caressing my ass.

I pick my least slutty skirt, a pleated A-line that drops to just below knee level, and a long-sleeved peasant blouse. I don't have any flats, but I do have some low heels that go with this outfit. This is one occasion I don't want to attract too much attention.

After applying my makeup, I admire myself in the full length mirror. Not bad, not bad. "It better be", my brain taunts me, "because you have to go out in public like this."

I don't have a purse (duh, that's why I'm going out like this) so I'm going to have to just hold my driver's license and cash in my hand for now. I get in my car, eternally grateful that I chose the tinted windows, and head down my driveway toward my certain doom. I'm more careful to obey all traffic laws now than I was on my driver's test. I've read the stories about what happens to transvestites if they get pulled over by the wrong cop.

As I'm driving to the thrift store I feel a freedom I've never imagined before. Mixed with abject fear, of course, but the feeling of my legs under my skirt, the different way a woman's shoe hits the accelerator, the way the seatbelt bisects my breasts, the way my hair flips when I check my blind spot before merging, it all makes me feel very...well, womanly. I'm almost smiling as I turn in to the thrift store parking lot.

Parking at the back of the building where no one will see me, I find that I can't leave the car. I'm too scared. The only other time I went out "dressed", I was seen by a guy. True, he didn't seem to know what I was as he looked me over from head to toe (twice!), and in fact I'm almost sure he was checking out my ass after he passed me. I check my makeup in the vanity mirror. Luckily it's okay since I didn't bring any in my nonexistent purse. Okay, you can do this, Annie. You can do this. Now go.

Checking that the parking lot is empty of other people, I get out of the car, lock it, and walk to the front door. You can do this, Annie.

It's a glass door, and as I'm reaching it there's a college student, a guy, coming out. Before I know what's happening, he's holding the door for me and I'm going to have to interact with him. Shit, shit, shit.

I glance up and catch his eyes briefly in thanks, then in my best female voice (here goes!) say "Thanks". Does he know? Is he gonna beat the crap out of me? Or worse, laugh?

"Sure", he says with a flirty smile, and somehow I can feel his eyes checking me out as I go in the store. I did it. I passed.

As I had hoped, it's nearly empty on a Friday night. A single young bohemian-looking guy is in the paperback section, probably looking for biographies of Chè Guevara among the tattered romance novels. Heading to the purse section, I find a couple dozen mostly ugly and out of fashion offerings waiting. But a couple look nice and I try them on for size. They're only 5 bucks each, so I get both. There's even some female style wallets nearby and I grab one of those that strikes my fancy. Hell, this is going so well I may even shop for a dress.

"Excuse me", says the bohemian guy as he taps me on the shoulder, and I just about jump out of my panties in surprise. "Oh, sorry, I didn't mean to startle you. Can I get past you to the appliances section?"

"Sure", I mumble, moving out of his way. Okay, dress shopping can wait. I've got to get out of here.

The cashier is a young girl, probably still in high school by the looks of her. She rings up my merchandise and says, "That'll be $15.50, ma'am". She gives me a smile that wordlessly says "I know, and it's okay".

Shoving a twenty at her, I say "Keep the change" and gather up my bags. She looks at me and says, "Thanks. Come back anytime. We have several girls like you who shop here."

Girls like me? I manage to stumble out the door as my mind races. Girls like me? Girls like me? Then it hits me. Of course! It's the perfect shop for Girls Like Me. Cheap, lots of clothes to choose from, including lingerie, shoes, and purses, and anyone in my circle of friends wouldn't shop here in a million years. I wonder how many Girls Like Me there are, but I'm sure as hell not going back in to ask.

Reaching my car, I buckle in quickly and leave the parking lot as soon as I can. The relief is palpable that I've been shopping as a woman without dying of embarrassment.

However, it's not long before traffic slows to a crawl. What's going on? Oh, shit, it's a police sobriety checkpoint. At 6:30 PM? What the hell? I've got to get home. As I get closer I see I have a different problem. They're taking cars at random for sobriety checks. Please, please, please, please, please don't pick me.

I'm lucky. As I get to the front of the line, the officer waves me through. He takes a close look at me as I pass, but I don't know whether he thinks I may be drunk, or he spotted me as a crossdresser, or if he just thinks I'm hot. At this point, I don't care. I've got 5 minutes to get home.

Racing in breathlessly at 6:59, I half expect Dave to be waiting for me. But he's not. He's too smart to be caught breaking and entering. Moments later, however, the doorbell rings. It's Dave, come to keep our date. Shit, shit, shit.

"Hiya, doll", he says effortlessly as he breezes in the living room. "You look nice. Ready to go?"

"Go?", I ask. "You didn't mention anything about going anywhere!"

"Why do you think you'd need a purse?", he asks. He glances over to the coffee table where my recent purchases lay. "Is this it? It's pretty. Let's get going, Annie. You're going to be serving drinks for my poker buddies tonight."

"No way, Dave. Now you've gone too far. If you think you're going to embarrass me in front of all your friends for the whole evening, you're delusional."

"Aww, that's too bad, Annie." He seems genuinely disappointed. "I had hoped to avoid embarrassing you in front of all your colleagues and clients. Besides, dressed like this I don't think anyone will know the truth."

"I...I...I...", I stutter, astounded at Dave's shocking lack of judgement. "I can't pass in front of your friends all evening!", I charge.

"You went shopping this evening, didn't you? In full daylight? Did you meet anyone?", he asks.

"That's different, Dave. I only said 5 words to anyone."

"And that's more than you'll have to say tonight. Plus, it'll be dark and you'll mostly stay in the kitchen." Once again he flashes the grin that he thinks is so charming, and he's right about that.

"It's nobody from work, right? Because if there is, I will seriously go murder-suicide on your ass. Don't shit me, Dave, this is my life you're fucking with."

"Nobody from work. I work there too, you know", he assures me. "Besides, I'm not that mean."

Yeah, just mean enough to rape my mouth and then my ass last night, and blackmail me into liking it. Okay, maybe the blackmail wasn't the reason I liked it, but I'm going to have to think about that some other time.

"You're a fucking bastard, Dave", I mutter to him as I gather my new purse. "Give me a minute to get some makeup and jewelry."

The purse is big enough to fit all my makeup, plus wallet and cell phone. I reapply my lipstick before closing up the purse, but other than that I'm still looking good. I add some dangly clip-on earrings to draw attention away from...well, everything else and return to the living room to find Dave waiting for me. At the last minute I trade my one-inch heels for one-and-a-half inch heels that are prettier. Taller heels, for some reason, force you to walk like a girl. I'm going to need all my tricks tonight if I'm going to pass for several hours in front of a bunch of guys.

Wordlessly we go out to his car, which to my chagrin turns out to be a Kawasaki motorcyle. It looks fast. Oh, this just gets better and better.

Dave climbs on and beckons to me to sit behind him. I can see the headline now: "Motorcycle accident claims two lives: one man, and one girly-fag wearing frilly lingerie". Guess which one is me.

"Come on, it's only ten minutes away", he says. I climb on, determined to use the handholds behind the seat rather than hugging Dave. Thirty seconds into the ride, however, I'm holding on to Dave so tight I can feel my breasts boring holes into his back. Ten minutes at these speeds could take us to the next county. Plus I can feel and see my skirt blowing back up my thighs, exposing my stockings up to the garter straps. A couple of cars honk their approval until I tuck the skirt between me and the chassis.

His apartment is nondescript but clean. He must be a trust fund child, though, because he's got every kind of expensive electronic device ever invented. Whatever buddies are scheduled as my personal hell tonight have not yet appeared. Dave pulls me into the kitchen and tells me the score. Apparently I'm his new girlfriend, and I lost a bet and have agreed to be his serving wench for the evening. Whenever anyone yells "beer wench" or "snacks" or anything similarly obnoxious, I'm to breeze in with the requested item and then leave. I'm not to speak unless Dave gives me the signal. At least I don't have to worry about my voice giving me away.

Soon the buddies arrive, pretty much all at once. I'm introduced to Steve, a thin white blonde in jeans and Nirvana t-shirt, Raj, an Indian with stylish glasses and dark hair, and Ty, a largish black guy in cargo shorts and an oversized jersey. They all give me a good looking over, and seem friendly enough. They seem to know the score, and don't expect me to do more than nod in hello. That's good. And there's been no pointing and laughing. That's better. Nor any beating-to-a-bloody-pulp. Best.

They're immediately laughing and joking among themselves, and it's not long before the "beer wench" calls come. The game room is dark except for the overhead lamp, which suits me fine as I bring them beer and snacks from the kitchen, then retreat for a few minutes between calls. At first I listen at the doorway to see if anyone mentions that, well, did you know, Dave, your "girlfriend" is a guy? But it's just poker and football talk, and I escape back to the kitchen open a beer for myself.

One hour and four beers later, I realize that in my anxiety I forgot to eat dinner and I'm rapidly getting sloppy drunk. Last time I delivered a beer to Steve I found myself flouncing out of the room to catcalls and hoots from the whole table. Get a hold of yourself, girl, before they start getting a hold of you!

After a couple hours, Steve is tapped out and leaves the game. He pops his head in the kitchen and tells me thanks, he had a great time, and I've been a really good sport. I smile and wave a goodbye to him. One down, three to go.

Another half hour, left mostly to myself in the kitchen (it must be getting serious in there), and Raj pops in to say goodbye. And then there were two.

The calls for beer and snacks have subsided, so I'm left alone for another twenty minutes until the silence is broken by Dave loudly groaning and Ty whooping in triumph. I wonder if I should go check on them, but reason that it's better to minimize my chances of Ty noticing what I really am. After a few minutes, Dave comes into the kitchen.

"Game's over, Annie."

"You lost?"

"Yup."

"Too bad. So I can go home now, right?"

"Sure, just as soon as you do a little tonsil-dance on my cock, baby."

Sigh. I briefly ponder the idea of arguing, but after what I did last night to Dave I'm not really in a position to be virginal about it. I might as well get it over with.

This time, I take his hand and lead him back to the bedroom. As we pass the poker table, I notice that Ty has forgotten to take his money with him. If he's that drunk, I hope he got a cab.

In the bedroom, Dave stands at the foot of his bed. He seems to like me on my knees in front of him, and on the theory that whatever gets him off sooner gets me home sooner, I teasingly take off my blouse and skirt. He responds with a grin and a visible rise in his crotch.

Pulling his pants down as before, I see he's already semi-hard from the sight of me in panties, bra, garter belt and stockings. I waste no time in taking his cock slowly into my mouth. I've done this before, so I know what he likes and what he doesn't. Before he's fully hard and too large to fit, I take him all the way in my mouth and slowly pull back, sucking and swirling my tongue as I go. The way Dave is moaning, he's gonna come in about 30 seconds.

I'm getting into it too, feeling pride ("in your cocksucking abilities!", my brain taunts me) and feeling my own cock start to stiffen in my panties. I can feel Dave's hands, larger than I remember them from before, caress my hair, down to my shoulders and then on to caress my breasts. It feels wonderful, but I'm concentrating so much on Dave's cock that it doesn't occur to me that Dave can't reach my breasts in this position.

So if it's not Dave's hands, then whose hands are cupping my breasts? But it's too late to find out. Dave spasms and grabs my head, forcing my mouth over his cock as it stiffens and shoots his cum at the back of my throat. Once again, my efforts to escape only heighten his sensations. It feels like he shot a shot-glass full of cum into my mouth.

At the same time I feel a long, hard object pressing upward on the bottom of my panties. What the hell have I gotten myself into?

Disengaging myself from Dave's cock, I spin back to see Ty standing behind me. He's naked. He's erect. And from the looks of it, he's got at least three inches on Dave's average size organ.

"Man, Dave, that was awesome", he crows. "Best porn I ever rented. Will she do me that way?"

My indignant reaction is delayed by the giant glob of cum in my mouth, which I swallow with some difficulty.

"No! What the hell, Dave? I thought he went home. What am I, your personal whore to rent out to whatever...wait a minute." Turning to Ty, "Did you say 'she'?" Ty couldn't have missed the giant boner sticking out of my panties, and with most of my clothes off it's pretty obvious I'm not a real girl. But he called me "she".

"Yeah, baby. I knew all along. It's cool, baby. Hey, if you don't wanna do anything, that's okay. But damn, you make one gorgeous babe, and it looked like you really know how to suck a cock."

"It's only her second time", brags Dave.

"No shit?", replies Ty.

I realize that the situation is completely out of control. I'm sitting on the floor, wearing sexy lingerie, makeup and a wig, with a tummy full of cum. And I'm staring at Ty's enormous cock.

I know, I know, it's a cliche. I'm not gonna change what happened to make it more racially sensitive. He had a huge cock. Not John Holmes big, but big enough that he sticks out in a crowd. Sticks out in a crowd. In spite of everything that just happened, I laugh to myself at that mental image.

And as Dave and Ty discuss my cocksucking skills, it seems like they just ignore me, laying on the floor in my underwear. And I start wondering how much of Ty's cock I could fit in my mouth. A third? Maybe a half, if I push it to the gagging point.

He's not hard yet. If I'm going to get it all in, now's my chance.

Silently I crawl on the floor over to Ty. They both notice and stop their animated discussion. Kneeling on the floor in front of Ty, I look up into his eyes.

"Oh, baby", he croons.

And that's all the encouragement I need. I take his cock with my hand and feed it past my lips. Immediately I push my mouth all the way toward his pubic hairs, but I'm already too late. He's hardening in my mouth, and I stop about an inch from the end, unable to take any more. I can feel him growing in girth, and soon my mouth is literally full of cock, and I have my answer. Half.

Taking the other half in my hand, I start sucking with my mouth and pumping with my hand. I can already taste Ty's pre-cum, and he's making noises like Dave did.

Pretty soon my knees start hurting from the hard floor, though, and I motion for Ty to kneel on the bed. I follow him, crawling on all fours to resume sucking the biggest cock I've ever seen in real life. It fills my world with its thick, veiny power. It waits to send its payload deep into me, and I am powerless to resist it.

Soon I feel motion at the other end of the bed, and my panties are pulled aside to expose my asshole. Dave is hard again, fully lubed, and probing against my tight sphincter.

My gasp of pleasure as Dave pushes his cock into my ass is muted by Ty's cock in my mouth. But I think they both heard it. Now they're both working me over, Ty from the front and Dave from the back.

My mouth is getting sore, and Dave's second orgasm hasn't come yet, so at some secret sign they send each other, they switch places. Flipping me over on my back, Ty pulls off my panties, leaving me only in garter belt, stockings, and bra. My God, he's strong! Putting my high-heel clad feet on his shoulders, he raises my ass off the bed and exposes it for his hard, hungry cock.

I don't know what I expected when Ty shoved his cock deep inside me, but I did my best to relax my sphincter. Even so, it felt like my muscles were ripping apart as he pushed his cock deep inside me. It took ten thrusts before he was in far enough to not be pushed back by my still-tender sphincter muscles.

Meanwhile, Dave is jacking off with his cock just inches from my face. I've seen this in dozens of porno movies, but I never imagined I'd be the girl.

As Ty pumps my ass with his telephone pole of a cock, I eagerly take Dave's cock in my mouth again. He's stroking the bottom as I suck the tip, and Ty spreads my legs wide as he pushes his cock all the way in. His balls are huge as they press against my ass, and I'm not sure but I think he's halfway up my small intestine. I caress Dave's dangling balls with one hand, while with the other I rub my own patch of pubic hair.

Ty begins pumping in earnest, and my own cock responds to the stimulation of my prostate. Then Ty grips my thighs tightly as he rams harder and harder and harder, groaning in pleasure as I feel his cum coat the inside of my ass. He pumps a few more times for good measure, and stays inside of me.

Dave moves his head down so we're in 69 position, and we suck each other's cocks greedily. It's only a few more moments until we both come into each other's mouth.

After a few moments of enjoying the afterglow, Ty pulls out with an audible "plop". Despite ourselves, we all laugh. My ass hurts like hell, though.

"Okay, beer wench, get your clothes on. You're going home.", says Dave.

That's fine with me. I'm tired, and I need to sort some things out. I've done a lot of strange things in the last 48 hours.

Dave and Ty leave the room as I get dressed and reapply makeup. It doesn't have to be great, just enough to last the motorcycle ride home. Luckily (I suppose) all the sticky cum went inside my mouth or my ass, so there's no mess in my hair. A quick brushing gets it back in shape. Wigs are made to be low maintenance.

Ready to go, Dave opens the door and I exit ahead of him. He says, "Thanks, and good luck."

I'm wondering what he meant by "good luck" when I hear the door close and lock behind me.

"You bastard!", I yell as I pound the door, but I know he's not coming back out. The more noise I make, the more attention I draw to myself. Shit, shit, shit.

"Dave, you're a fucking bastard", I mutter. At least I have my cell phone. We're a big enough city that taxis are available 24 hours. You just might have to wait a while. I call a taxi to meet me, giving a description of myself (I leave out the part about cum dripping out of my distended asshole into my panties), and look for a place to wait the 10 minutes until it gets here.

I can't just stand on the corner, unless I want to meet the vice squad up close and personal. I don't know if hookers ply this part of town, but I'm not going to be mistaken for the first. I decide to wait on the steps to the manager's office.

Shortly the taxi arrives, and I climb wearily in the back. I give the driver my address and slump in the seat.

"Long night, eh?", he inquires.

"You wouldn't believe me if I told you..."

  

  

  

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