Annie Gets Blackmailed

by Anne Zvesteit

Part 4

 

I thought it was all over after being forced to be the "beer wench" for Dave and his poker buddies. Dave and his friend Ty had their way with me, then cast me out into the night to find my own way home. Fine. It's finally over. I can go back to being a closet transvestite.

Then, bright and early Monday at work, I get a package via intraoffice mail. There's no return department listed, and it's about the size of a large chocolate Easter bunny. Ripping open the envelope, I find that it's not a chocolate Easter bunny. Unless they're making Easter bunnies out of latex in the shape of a man's sexual organs, that is.

There's a note, written in untraceable block letter writing:

Practice, practice, practice. You'd better put in some DEEP practice for the show you're putting on Friday night. Take care of your THROAT.

Shit, shit, shit. So it's not over. Dave can still cut my career off at the knees and make me a laughingstock with a single e-mail. He's got me by the short-and-curlies, and apparently I'm going to be kissing his short-and-curlies if I want him to keep quiet.

I'd never even touched another man's cock before last Thursday. Last weekend I learned that I'm a natural born cocksucker and I'm willing to take it up the ass. But deep throating? That's a whole different ballgame. And what's this about a show?

I remember how Ty paid Dave to watch me suck Dave's cock, and how afterwards I fucked them both silly. God, what's become of me? Am I still doing this because I'm being blackmailed? Or because I like it?

In any case, I can't very well leave a 7" flesh-colored latex dildo (with realistic balls, nice touch, Dave) lying on my desk. I take it out to my car and put it in the trunk where no one can find it. I'll think about what to do with it later.

Okay, it's later and I'm driving home and wondering how I can get out of this. How low will I debase myself before it's too much? How big is my audience going to be? Will any of them be as big as Ty? Cause his cock was just enormou...shut up, shut up, shut up!

I want...no, I need those pictures back. Dave may be calculating and sly, but so far he hasn't lied to me. I'll do his stupid little show if that's the end of it. Otherwise, I'll just have to kill him. I'm not sure yet if I'm serious about that last part. If I'm going to lose my career, he's going to pay too. Let's hope it doesn't come to that.

So I practice. The urge to gag is strong. You have to take it little by little. After an hour I was able to keep the dildo in for 3 seconds. Long enough to take a digital picture.

I set up the camera to just get my mouth and the dildo. Nothing that will identify me if it gets out. Set the timer and...gag,gag,gag,gag,FLASH! Spit the dildo out and check the picture.

It came out all right. I create a throwaway e-mail account, go down to a WiFi-enabled coffee shop and send my picture to Dave's work e-dress with this message:

Agreed. But this is the end. If you cross me, YOUr hold over me WILL end. I am BEing DEADly serious.

I'm taking a chance threatening him with murder, but between the coffee shop and the throwaway e-mail, I'm pretty anonymous. Dave, however, will know that two can play this game.

Almost immediately, I get a response from a similar throwaway account:

Agreed. Do a good show Friday and I will leave you alone.

So that's that. I've got to go home. I've got some practicing to do.

The gag reflex is surprisingly resilient. You can shove a dildo down your throat all night, and it still makes you want to gag. But with perseverance you can overcome it. By midnight I was able to keep it in for 10 seconds.

The next night I worked on thrusts. Dave will want to fuck my mouth like he did last weekend, and I'll be damned if I'll let him control my reaction to it. I'm in control this time, and I'm going to deep throat his cock until he begs for mercy.

Wednesday, a different position. Lying on the bed, head hanging off the edge. It has the advantage, I find, that it makes a pretty straight shot down the throat, with the disadvantage that you get testicles resting on your eyes. Or maybe that's a benefit. I've now mastered the art of breathing on the out stroke, holding my breath on the in.

Thursday, I give my sore and battered throat a rest. The dildo looks lonely, though, so I take off my panties and let it explore my ass. It finds my prostate and stimulates it, again and again and again, and my orgasm shoots almost three feet in the air.

Friday night. Last time he showed up at 7:00, and I assume tonight will be the same. I start with a long, hot shower and full body shave. I make sure to shave my ass as well, as it's likely Dave will be sticking his cock back there. Gazing at my bushy pubes, I have a sudden desire to clean them up. So I shave them into a nice, trim triangle. Except for the penis and testicles, it looks a lot like a pussy.

What to wear? I'm putting on a show, apparently, so I'll want to dress in my best. I have a matching bra/garter/panty set in Prostitute Red, with red nylon stockings to match. Add a red satin slip to complete the lingerie portion. Then a flouncy red dress, mid-thigh height (just enough to cover the garter straps, unless I want to show them) and low cut enough to give a glimpse of the lacy trim on my slip. As for shoes, it's time to break out the 2-1/2" Fuck Me pumps I've been waiting for a special occasion to wear. If this isn't a special occasion, I don't know what is.

Next, the wig and makeup. A few finishing touches with clip-on earrings and bracelets for ankles and wrists, and the woman staring back at me from the mirror is one hot, sexy piece of ass. Dave wants a show, he's gonna get a fucking show. I spank myself on the ass to prove it.

I think my panties are already riding up my ass. God, I love that.

It's almost seven, so I gather up my makeup, driver's license and cash into my clutch purse. And I wait.

But not for long. Promptly at 7:00 the doorbell rings. It's not Dave, it's Ty.

"Dave couldn't be here", he explains, "so he sent me to pick you up. Are you ready?"

My arrogance withers. Considering that just last week I had this guy's enormous cock shoved deep in my mouth and then in my ass, I think I did pretty well to blankly nod yes. We go out to Ty's car, which thankfully is actually a car rather than a two-wheeled death machine like Dave's.

We drive in silence for a while, then Ty glances at me and says, "Hey, uh, I'm sorry about kicking you out last Friday. I didn't know Dave was gonna do that."

"I made it home okay, Ty. I'm a big girl.", I answer. I'm still kinda pissed that Ty let it happen, but mostly at Dave.

"You look fine tonight", Ty says. The way he says "fine" makes me blush. "Thanks", I reply.

Am I ashamed that while he drove, I stole glances at Ty's crotch? Yes, I am. Did he notice me doing so? Yes, he did.

We drive on in silence until we get to a nondescript house in a quiet neighborhood. This is it? I guess I was half expecting a strip club or something, but I guess they're all busy now, aren't they?

Ty opens my door and holds my hand as I swing my stockinged legs out of the car. There's a skill there that you have to learn, how to get in and out of a car without showing your panties. I'm learning.

Tyleads me to the back door, then into a back bedroom to get ready. There's a girl in the bathroom putting on makeup. So it's gonna be a lesbian show, huh? Well, that'll be a change from my recent activities, which mostly seem to involve genitalia of the male type.

Ty explains the score to me. The crowd is waiting in the living room. It's about 10 guys, and they're all so-called "Admirers" of cross-gender girls, so there's no chance of a mass assault by an angry mob. Well, not much anyway. They're paying to see me and the girl (whose name is Dana apparently) have sex on stage. They're likely to tip, and tip well, if they like what they see. After the stage show ends, by prearranged signal they can ask one or both of the girls for special "favors", for which they will pay handsomely. Ty gets a small cut for being the bodyguard and making sure things don't get out of hand. He hands me an envelope. Inside is a small stack of $100 dollar bills that he says is my cut from the entrance fee. If I put on a good show, he explains, and get requests for afterward, I can make up to $500 or more per guy.

I'm shocked. Between the entrance fee and a couple guys afterwards, I can make more money in a couple hours than in a whole week at my job.

Dana appears from the bathroom. She's hot. Tall and leggy, wearing a sexy dress that gives tantalizing hints of gorgeous lingerie underneath, I think to myself that I'd gladly give my envelope of $100's to fuck her. Instead I'm being paid to do it. There's something familiar about her, though. She's not a business client, is she?

"Hiya, doll. Welcome to showbiz!", she says with a fetching smile.

Wait, I know that smile. "Dave? Is that you?", I ask incredulously.

"Yes, but tonight, dear, it's Dana. Are you ready to put on a show?"

I should have known it would come to this. "I'm ready, Dana. Let's go put on a show!"

  

  

  

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