Annie Gets Blackmailed
by Anne Zvesteit
Part 1
I should have known it would come to this. Dressed in sexy lingerie, made up like a whore, on my knees in my bedroom staring at a hard, throbbing cock just inches from my face.
But I suppose I should start from the beginning.
I've dressed in women's clothes ever since I could dress myself. I was five when it started. My sister's satin panties felt so good, I would sneak in take them from her drawer, and I always put them back after a few minutes of wearing them. Only later did it become a sexual obsession.
I had to keep it very, very hidden in high school. I was already a girlfriend-challenged geek, and to be found out as a crossdresser would have invited universal derision and frequent beatings. But I still wore them whenever I could.
I told myself I had quit when I got married, and I really meant it. Or thought I did. When I finally did tell my wife that the urges had always been there and always would be, she was actually relieved. Our marital problems hadn't been her fault after all. We divorced amicably, luckily before we had any children to fight over.
So here I am, a divorced 40'ish middle manager by day. No one suspects that almost every night when I get home, I dress up and play.
I'd had a rough day today, so I was in the mood for a release. Without telling us, the I.T. department had put in software that logged and analyzed employee web surfing habits. I guess they had a problem with productivity or something. Last week I had discovered the transgender writings of Michele Nylons, and today (at lunch, I hasten to say) I eagerly devoured her latest story. This one was about a middle manager who went to jail and became a tranvestite prostitute.
I knew it was probably technically against company policy, but it's not a porn site or anything. It's just creative writing.
As I finished reading the story, an e-mail popped in my Inbox. "Gotcha" was all it said. "Oh, no, I'm not opening that", I thought. You open the e-mail, and the spammers know it's a valid address. Delete. Ha. Nice try, spammer.
Then another e-mail comes in. "What are you wearing?", the subject asks. That's an odd coincidence, considering the story I was reading, but [Delete]. Nice try.
Then another. "Do you like panties?". Oh, shit. That's not a spammer. I've got an enemy. Shit, shit, shit. I could lose my job if this gets out. "So, Mr. Smith, why did you leave your last job?" "Well, they found out I like to dress in women's clothes." "Okay, buh-bye."
I risk a reply in hopes of quick damage control. "Whoever you are, please be aware that my brother just confided in me a very personal problem, and I was researching how to help him. Please let this drop." It sounded plausible. I hoped it worked. Shit, shit, shit.
Needless to say, I was useless the rest of the day worrying about my secret. As I passed people in the halls I imagined every one of them picturing me wearing silky panties under my suit. I didn't help that I actually was wearing silky panties under my suit.
When I got home, I immediately went to my room and shucked off my suit. My bikini panties (worn under my boxer shorts—I'm no fool) had ridden up into my ass, making my butt cheeks rub slightly together as I walked. God, I love that.
I live at the end of a long driveway, at the end of a long street, so I don't worry too much about passersby looking in the windows. The shutters are all closed anyway (as I said, I'm no fool), but in general I feel pretty safe in the house that no one will happen by and see me.
Slipping out of my daytime panties (into the laundry you go, my pink pretties), I look through my drawers for something comfortable, but feminine.
A simple slip will do, black satin with pretty lace, and enough room in the chest for my B-cup falsies. I start with a simple comfortable, flesh toned bra. Into each cup goes a water balloon wrapped in a kneehigh stocking. They are surprisingly realistic in shape and bounce, as long as you don't overfill the balloon. Adjusting the knots to the front, I admire my large, erect "nipples". Mmmm, nice.
Next for the wig. It's a brunette to match my eyebrows, with hair falling halfway down my back. I love the feel of it cascading over my shoulders. A quick brushing is all that's needed for walking around the house.
Now, the slip. Dropping it over my shoulders I feel an electric thrill as the soft fabric caresses my torso. Adjusting my breasts gives me an excuse to feel myself up, and I discreetly take it.
"Do I want to bother with stockings?", I ask myself. Yes, I need a thrill tonight. Luckily I already shaved my legs this morning. I choose some sheer black stockings, with a lacy black garter belt to hold them up. I love the look and feel of stockings.
As for shoes, nothing fancy tonight—just some one-inch heels with pointed toes that make my legs look longer and sleeker. Plus I love how they click-click-click on the hardwood floors.
You've forgotten the panties, I hear you say. No, I haven't. I save them for last. I have several pairs that match this slip, but tonight I choose the black satin flutter bikini panties. Sliding them slowly up my legs, I feel more and more feminine every second. As they reach their destination I revel in the silky caress of my pelvis.
The slip comes down just far enough on my thighs to hide the garter straps, unless I raise my hands above my head. I reach to check the dust on top of a picture frame, and am rewarded in the mirror with a view of my garter belt straps and just a hint of panties.
That's enough for now. I'm hungry.
Walking to the kitchen I'm very aware of the swish swish of the slip and the gentle bounce of my breasts. It feels glorious. I'll bet my ass looks great too.
Opening up a bottle of wine, I drain two glasses in quick succession. I needed that, and now that I'm a bit tipsy I don't really want to cook something. Leftovers go in the 'crowave while another glass of wine goes down my throat.
Having finished dinner, and now more than a little drunk, I start getting horny. Not just walking-around-in-women's-underwear-horny, but really horny. My body feels so soft beneath the slip, and running my hands from my breasts down to my legs I pass the tantalizingly thin strips of elastic caressing my hips. How easy it would be for them to break, and my panties to fall down around my ankles. I giggle to myself at the thought.
I've got to pee. Staggering into the bathroom I lift up my slip to reveal the pretty panties. God, I've got a nice ass. Then down to my ankles the panties go and I waddle over to the toilet to sit down.
I'm a hot babe, I'm thinking. The panties at my ankles are mesmerizing as I finish peeing, then dab at my privates with a bit of toilet paper. As I strut back to the bedroom I once again revel in the click-click of my heels on the floor and the swish-swish of my satin slip against my body. This is going to be good.
Turning on the stereo for some background music, I'm pleased to hear the opening chords of my favorite song, "Bad Boyfriend" by Garbage. I can't resist this. I run, click-clacking and boobs bouncing, to the open expanse of hardwood floor in my living room. Using the remote control as a fake microphone, I become the lead singer to a raucous, adoring audience.
Running my right hand over my forehead and down my face:
"I've got a fever, come check it and see..."
Knees together, both hands on microphone, hips grinding:
"There's something burning, and rolling in me..."
Turn around, bend over and sing through my legs:
"It may not last but we'll have fun to the end..."
Spin back forward and point to an imaginary guy in the third row:
"Come on, baby, be my bad boyfriend."
Hips swinging side to side for the power chords that follow, then I strut to Stage Left, feet kicking up behind me with every step:
"I wanna hear you call out my name..."
Legs wide apart, bending at the waist to sing to the front row:
"I wanna see you burn up in flames..."
Straighten up, left hand on hip and strut back to Center Stage:
"Keep you on ice so I can show all my friends..."
Legs apart, arm straight up, looking up in a power pose:
"C'mon, baby be my bad boyfriend."
Strut over to Stage Right, where I caress myself from shoulder to stomach sensually:
"So ripe so sweet, come suck it and see..."
Hands continuing down until I spank myself on the ass and stomp my foot:
"But watch out Daddy, I sting like a bee..."
Collapse into a crouch as the end of the line comes:
"I know some tricks I swear will give you the bends..."
Straighten up and hug myself across my stomach:
"Come on, baby, be my bad boyfriend."
Strut back toward center stage:
"My fever's rising, you ran into luck..."
Stop in mid stride, acting surprised:
"Say what, sugar, you wanna get what???..."
Hold my index finger seductively near my mouth:
"I wanna give you one hundred and ten..."
Take that finger and do a come-hither motion to an imaginary guy in the 5th row:
"C'mon, baby, be my bad boyfriend."
As the guitar solo wails, turn my back to the audience with legs spread and rub both hands up my legs to my waist, briefly lifting my slip up to show my panties, then letting it fall as I turn around for the chorus.
Swing my left arm in a wide circle with the power chords as I look down to the side:
"It's wild, the way you tease me..."
Another wide circle, this time looking down to the other side:
"It's wild, the way you free me..."
Continue the arm swing, stopping at the top of the circle, looking up:
"It's wild, the way you reach me..."
Both forearms held together as if tied with rope, slowly sinking down on my knees and leaning backwards as the last note stretches out 12 full seconds:
"Wrapped me up in your wire from the staaaaaaa-aaaaaaa-aaaaaart."
The front row has a great view of my panties as I lean way back, and it gets better briefly when I fall over backwards as the guitar solo wails, writhing on the stage.
Lying on my side at center stage, singing to the audience, not caring if my panties are showing:
"You've got the women waiting in line..."
On hands and knees, facing sideways, giving the folks in the front row either a cleavage or panty view, depending on where they're sitting:
"I'm not asking you to make up your mind..."
Crawling toward the center of the front row seductively:
"I could make you happy, at least now and then..."
In a stage whisper to an imaginary guy in front row center, as the concert hall goes silent:
"I've got something special for my bad boyfriend."
Jumping to my feet in one fluid move (not easy in high heels while singing, but what can I say—I've practiced):
"If you can't love me honey, go on just pretend..."
Grip the hem of my slip and pull it up in my fist to mid-stomach level, writhing in desire as I show the whole audience my garter belt and panties:
"I've saved something special for the very end..."
Drop the slip and send my arm out to the side in a wide arc ending at the top:
"If you can't love me honey, go on just pretend..."
Drop the arm down, going down to my knees along with it, close enough to touch the front row's extended hands:
"Come on, baby, be my bad boyfriend..."
Slutty:
"Oh, come on, baby, be my bad boyfriend..."
Sultry:
"Come on, baby, be my bad boyfriend..."
Pleading:
"Come on, baby, be my bad boyfriend..."
Pouty:
"Come on, baby, be my bad boyfriend."
As the song ends, I turn the sound down to normal, get up, take a bow to the imaginary standing ovation, and go "backstage" to my bedroom.
Laying on the bed, I begin to caress myself. Starting with the stomach, moving up briefly to my breasts, down to my shapely ass and the straps laying on my thighs holding my stockings up. Unable to control my lust, my legs rise and spread as my hands find the thin, silky fabric of my panties.
Gasping in pleasure, I begin to rub the panties with my first two fingers, then slide them underneath the fabric to find the little area between my balls where I imagine my pussy is. The movement of my fingers pulls the panties to and fro across my erect penis. As the two-finger massage goes faster and faster I can feel my orgasm coming and start to moan and whimper. My wife was a silent climaxer, but as a woman I am very expressive.
Finally the burst comes as waves of pleasure course through my body and my sperm shoots into my panties. I lay there for a few moments, enjoying the afterglow, then get up to go to the bathroom again.
Coming out of the bathroom I'm surprised by an intense flash coming from the direction of the bedroom. As I see the man sitting comfortably on the edge of the bed, looking relaxed and holding a camera, my reaction is the same as countless women through the ages caught naked or vulnerable: I scream like a girl and cover my chest and crotch with my hands.
As the realization strikes that he has just taken a picture of me, I'm struck numb with the implications. I don't even recognize him until he speaks.
"Well, well, well. What have we here? That was quite a show you put on."
It's Dave, the new guy in the I.T. department. He's young, a few years out of college, athletic, smart, and...sitting on my bed. Suddenly it dawns on me.
"You! You sent those e-mails!", I accuse angrily.
He smiles. "Yup. There are certain advantages to being the corporate internet administrator, and one of them is seeing what everybody downloads. You've got quite an interesting download history, you know?"
Now I'm angry. I forget what I'm wearing (funny, though, as I remember it later, that I kept my "girl" voice) and snarl at him, "How did you get in here? I'm calling the cops and you, my friend, are going to jail for breaking and entering." If I can intimidate him (Ha! You're going to intimidate this guy while standing in front of him wearing women's underwear???) I just might be able to salvage the situation. "Just give me the camera and I won't press charges."
But he's too smart for that. I knew it before I finished speaking. He's thought of everything. What am I going to do, waddle out in my high heels and lingerie, and "Yes, officer, he broke into my house and took these pictures of me and...yes, I suppose he would show you the pictures if you asked, but...no, this is not just a lover's spat, and I would appreciate it if...". If...if you would just not come at all. Shit, shit, shit.
"What do you want, Dave?", I ask (interestingly, I seem to be stuck in female voice when talking to him—why is that?).
"Just talk.", he replies. "Here, be a good girl and put this on. Meet me in the living room." He points to one of my simple dresses—short sleeved and high in the hem, nothing fancy but very pretty nonetheless.
I briefly consider calling the cops as he saunters out of the room, but it's no good. We're gonna play Dave's game for a while, he's gonna humiliate me and then leave. I put on the dress, change my cum-soaked panties for a fresh pair (dammit, all I have are sexy ones!), and click-clack out to the living room.
"Okay, I'm here, Dave. What do you want to talk about?" It's humiliating standing in front of him this way, but I'm determined to keep some semblance of self respect.
"Sit down, uh...what did you say your name was, sweetie?" God, he's enjoying this.
"Anne", I reluctantly reply.
"Aha!", his eyes light up, "as in 'Anne Zvesteit', eh?"
Underneath it all, I'm somewhat pleased that he guessed my little wordplay.
"Sit down, Annie. I want you to tell me all about your little hobby here. Your secret is safe as long as you cooperate completely." He smiles what I'm sure he thinks is a charming smile. He's kind of right about that.
If I'm going to do this, I'm going to do it right. So I sit down opposite him in my best girl pose, crossing my legs discreetly as I've practiced so many times before.
And I tell him everything. My sister's panties, the constant hiding, the several times I gave it up (for good this time, I always told myself), the divorce, and the freedom I now enjoyed to engage in "my little hobby" now that I lived alone. Truth be told, it actually felt good to finally tell someone about it.
Dave listened intently and made no threatening moves. Neither did he offer me the camera when I'd finished my confession.
"Fascinating", was all he said. Luckily he didn't do the Spock eyebrow thing when he said it, or I might have laughed. All geeks are the same.
"Do you wear makeup also?", he asked. I got the impression he was genuinely interested, but it may have been that winning smile he throws around so carelessly.
"Yes. I have some in the bathroom I use sometimes when I want to go the extra mile."
"Annie, I want you to go put your makeup on.", Dave said.
Now my guard was up again. "No way! Haven't you humiliated me enough?"
"Show me your best makeup job, and some prettier high heels, and you'll hear no more from me." Either he's a really good actor, or he's actually telling the truth. Shit, shit, shit.
"All right. Wait here. This will take about 20 minutes. Help yourself to a drink. I'll show you what you want, and then we're done." I must be fucking crazy.
"You have my word, Annie."
I click-clack back to the bedroom, thinking about what shoes to wear with this dress. My makeup routine is pretty simple. Good enough to fool the casual observer, but nowhere near the routine Michele Nylons talks about. I won't bore you with the details, but when I finished I saw a reasonably pretty girl looking back from the mirror.
Dave wants heels, I'll give him heels. I've got several pairs of black pumps (not easy to find in women's size 10, but luckily I'm fairly small for a guy) and I choose a sexy pair with a 2 inch heel and a little black bow on top. Any taller and they start to hurt your feet after a while, and I've got enough problems tonight without worrying about my feet. As it is I feel my cock start to stiffen as soon as I start walking in them. Stop it! This is no time for you to wake up.
Dave has taken my offer and fixed himself a drink. As he sees me, he looks surprised, as if he hadn't expected me to actually come back.
"Annie, you look gorgeous", he says. I don't know if he's mocking me or if he's actually serious, but either way a thrill goes involuntarily up my spine at the compliment.
He stands up, setting his drink down without taking his eyes off me. Against my will, I feel my cheeks blush at the attention.
"Do you ever go out like this?", he asks.
"Only once. On a business trip I walked down the hotel corridor to the ice machine. I was actually wearing this dress, and it was late enough I didn't think anyone would be up. In the hall I saw a drunk businessman coming back to his room. I couldn't avoid him, so I just kept going. He was looking me over from head to toe the whole time, and I'm sure he was checking out my ass too."
"Did that make you excited?", asks Dave.
"Yes", I admit. "I'm glad I didn't have to talk to him, but he obviously found me attractive. Which is what I was going for, I guess. But only for me, not other people."
"I see", said Dave. "So you like to be pretty, and it gives you a thrill to be attractive to men. Have you ever fantasized about having sex with a man?"
"No!", I start, but Dave interrupts me.
"Ever stuck a whole carrot in your mouth, just to see how far it would go? And compared it to your own cock size? Ever wonder what a cock would feel like in your mouth, just for a second? Ever bend yourself upside down on the bed to stare into the business end of your own cock? Ever tried to lick your own pre-cum off? Huh?" Dave is smiling, and I'm wondering whether he's a mind reader, or has been watching me for the last 20 years.
He knows the answer from my face. "Okay, Annie, I'm satisfied. I'll go now, but before I do I have an offer for you. You can take it or leave it, no strings attached."
"What is it?", I ask.
"You want the picture that's in my camera. I want a blow job. I think a trade is in order."
"No way, Dave, I'm not that kind of girl!" Jesus, where did that phrase come from? "What I mean is, I've never done that and I don't know if I can without puking." I can't look in his eyes, knowing what he wants me to do.
"Look," I plead, "how about if I just kiss it up and down both sides and then give you a hand job? I promise to make it good." God, what am I doing?
To my surprise, he agrees. He takes my hand tenderly (I dare not snatch it away, unless I want him to take his picture—and my sanity—home with him) and leads me back to the bedroom. Click-clack, click-clack.
"Now, if I kiss your cock and get you off, you'll delete that picture, right?". I have no choice but to trust him, but I want to make sure the deal is set.
"You have my word. Now, on your knees, you sexy vixen!"
Reluctantly I drop to my knees in front of him. Suddenly his crotch looks huge in front of me. I'm acutely aware of my garter belt and stockings, visible as my dress rides up my thighs, and of the gentle stretch of my panties between my legs. He's already stiff inside his pants, and my hands tremble as I undo his belt. Not wanting to prolong this embarrassment any longer than possible, I drop his pants and underwear to his ankles together.
And there it is. He's circumsized, average size (just a little bigger than mine), and—oh, God—throbbing expectantly.
I should have known it would come to this.
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