Whips, Chains & Wicked Women, Slut-boy Stories – ebook

Excerpt

Tara’s Tale

 

Let’s trip back to 1986. That’s when this wonderful life of mine really started.

Even though we were only high school seniors, Eric and I were like an old married couple already. We’d been steady for nearly three years, and we’d even lived together for two months, having shared an apartment since we turned eighteen. Unfortunately, also like an old married couple we’d begun to bicker a lot, and our sex life had grown ever more unsatisfying. But finally I saw my chance to solve both those problems. Adroitly I maneuvered Eric to right where I wanted him. Then I began putting into play a plan I’d already devised with a few friends of mine on the cheerleading squad.

Actually, we were more than just ‘friends’. Unbeknownst to Eric, I’d been bisexual for six months, cheating on him with a growing assortment of lesbian lovers.

I really had no choice in the matter – as I said, our sex life had become supremely unsatisfying. Football hero that he was, Eric’s most important equipment was unfortunately junior varsity. Even worse, he’d developed an incorrigible problem with it: premature ejaculation.

I never blamed him personally for either of these deficiencies. After all, we are how we are made. And was I not the homecoming queen, and the hottest girl in school? My hair was then and still is a thick burnished bronze, my skin flawless and tanned and my eyes a dark cobalt blue. My body has always been effortlessly fit and my ass and tits the envy of everyone. What male in the world could possibly keep from coming at the sight of me unclothed and closing in on him?

Still, endless sexual frustration is intolerable – at least for me. For certain significant others it may be exactly what they deserve. Anyway, I eventually found I that could only get off properly by riding Eric’s face.

He learned to be good with his lips and tongue, no doubt. And even better was the overpowering thrill I felt at holding him down, burying my fists in his hair, grinding my crotch in his face and even fucking his outthrust tongue. Yet soon even this wasn’t enough. I needed a proper cock, goddamn it! Luckily I then learned of a certain cheerleader’s clique that had suffered similarly, and had henceforth discovered some amazingly fulfilling accommodation.

I met them, joined them, and despite my lifelong heterosexuality, I quickly discovered an unquenchable thirst for having my pussy pounded with a big old strap-on dildo. More surprising still, after a period of delighted experimentation, I developed an even more insane craving for doing the pounding myself. Soaking up my classmates’ feminist wisdom, I eventually became so dominant that I wanted nothing more than to forcibly feminize my supposedly stud-boy football player boyfriend. I’d teach him how to use a fucking cock! The more he annoyed and disappointed me, the more determined I became to turn him into my submissive little lifelong sissy slave she-male slut-boy. And finally he gave me the opportunity.

“Come on,” he griped. “We’re going to be late! Why does it always take you so long to get ready? Curling your hair, making up your face, dressing and undressing over and over again, it never ends!

“Not that I want to go to this party anyways,” he immediately averred. “Your friends are always making innuendos about my dick, and that other little problem I have. Did you really have to tell everyone? I can’t go anywhere without hearing about the alpha male ape with the sub-zed dick. If we have to go, I want to get it over with already.”

Pissed off at his badgering, I was opening my mouth to tell him so. But then inspiration struck, and opportunity blossomed.

It was time to put an end to such tiresome bickering – and so much else – forever. Casually, giving no hint of my duplicity, I laid my trap.

“It takes time for me to look my best. You should appreciate it Eric: who else has such a hot girlfriend? We are the best-looking couple in school. We have an image to maintain. But I’ll tell you what: if you really don’t want to go to this party, we can stay home tonight. But that’s only on the condition that you let me live out a particular kinky thrill of mine. Let me show you what an hour or more of proper female care can do. Let me curl your hair, and make up your face. I’ve always wanted to see how pretty you might be with the benefit of a woman’s professional touch.

“It’ll probably turn me on so much I’ll go nuts, and fuck your ever-loving brains out,” I purred, “And who knows? You might find it exciting too. So decide, Eric. It’s either that, or we go to the party, my friends all ridicule you mercilessly, and afterwards I cut you off completely: no more sex forever. What do you say?”

Utterly confounded, Eric gaped at me.

“You…you wouldn’t…use sex as a weapon?”

Oh, yeah baby! In ways you can’t possibly conceive! Still, keeping this thought to myself I merely nodded.

“That’s right. Either let me give you a makeover tonight, or forget about ever getting laid or even kissed again until you finally give in.”

He stood there, several expressions competing for possession of his face.

Anger, dismay, embarrassment, worry; possibly even a deeply hidden yearning: which would come out on top? I was betting on the last, and after no more than half a minute I raked in my winnings: his masculinity, sexuality, mortal life and eternal soul. Within a minute he foolishly threw up his hands.

“All right already! I’ll do anything to get out of going to this goddamn party!”

“Excellent!” I gloated.

“Oh, baby, this is going to be the best, most momentous night of our lives! I’ll tell you what: you go into the bathroom and take off all of your clothes. Piss and shit, if you haven’t already. Then come back out here and sit in my chair.”

Without a demurring word he went to comply.

Wonderful! Oh, this had gone better than I’d ever dreamed…

As soon as his back was turned, I swiveled my inconspicuous webcam to cover the chair and vanity. With a few computer clicks I started it recording (and incidentally transmitting to the party we’d be missing), and then went into our walk-in wardrobe to choose three of my stoutest leather belts. When I emerged, Eric (or Erica, as he would be forever known after this) was sitting naked, ill-at-ease and fidgeting before the three-way vanity mirror.

“Excellent!” I soothingly crooned again.

“Hold still, sweetie. I’m going to belt you down now. There’s nothing to worry about. I just don’t want you changing your mind about this before you finally see how sexy and slutty and tasty you look as a lady.”

Eric squirmed a bit, but he remained properly docile as I positioned his hands in his lap and then used my first belt to strap his chest and shoulders to the back of the chair. The second belt likewise restrained his elbows and belly, and the last one passed around his spread thighs and under the seat.

He could still move his lower legs, feet, hands, and forearms, but not enough to escape or seriously resist me. And right according to plan, his hands immediately capitalized on their freedom by wandering down and beginning to stroke and fondle his tiny two-inch erection.

Aha!

Either bondage or the strange anticipation of everything else that lay ahead was turning him on despite his stupid male reservations – if even those weren’t a sham in the first place. Perfect. Under the guise of giving myself room to work I pulled his chair back a bit, allowing the recording camera to capture both his miniscule prick and what he was shamefully doing with it. Then I plugged in my curler and picked up my hairbrush.

I’ve always loved Eric’s hair.

Thick and full, shoulder-length, it’s still truly black, and not the deep dark brown that is often misidentified as such. Already clean and shining, I nevertheless gave it a good twenty strokes with the brush, more for my own enjoyment than anything else. Then I put down the brush, picked up my pick and curler, and began to professionally style those delicious locks.

Okay, true, I wasn’t yet a licensed professional. But I’d been learning on my own for years, and I intended even then to go on to cosmetology school right after graduation, despite the fact that I’d never need the money. Styling hair is just something I’ve always loved, and indeed probably the original seed that eventually drove me (along with the other above reasons) to finally sissify my man. I shit you not, since I first saw them I dreamed of getting my hands on those long, silken tresses. And once I finally did I enjoyed every second of it, making that cool hippy-hair into a true feminist work of art.

Remember, these were the late eighties. Big hair was in big-time. Over the course of an hour I used my curler, pick and hairspray to transform my nascent slut-boy’s locks into such a bushy, curly mass of decidedly slutty ringlets that he proved irresistibly attractive even to himself. Finally I pulled back, allowing him access to the mirrors.

“How do you like your new hairstyle, Erica?”

“I…I…I really do look like a girl!” he stammered. His breath was coming fast, and he continued to play with his pitiful little stub of a prick.

“Yes you do,” I teased.

“You look like a deliciously sexy little slut! So, are you getting in touch with your feminine side yet, Erica?”

“I…I guess so.” He was blushing almost purple, and squirming furiously against the restraining belts.

“Good girl,” I breathed. “Because I am just getting started on you! Now, let’s get that pretty face of yours all made up!”

I moved back around in front of him, blocking his view of the mirror again, but not the camera’s view of him, of course. Then I went joyfully back to work.

Foundation, blush, eyeliner, mascara, lipstick, et cetera, I practically troweled on the cosmetics. Soon I had him so heavily made up he looked like a caricature of the prototypical prostitute. Then I applied long, dangling clip-on earrings and once again moved around behind him, letting him see the results.

His eyes popped wide in shock. He gasped, and then started breathing heavier than ever. His fondling took on a renewed urgency, as I leaned over him and began whispering dirty-talk into his ear.

“Look at you, you disgusting little slut!

“You are a slut now, aren’t you Erica? You’re a sexy, sleazy, sissy little slut-boy. And you’re incredibly turned on by it. Don’t even try to deny this. Your puny little penis is as big and hard as it can possibly get – bigger and harder than I’ve ever seen it before. So admit it for me, slut-boy! Tell me that you’re a slut and how much you love it!”

“I…I’m a slut!” he instantly moaned. “I’m a wretched slut and I love it!”

And with that he suddenly explosively groaned, wrenched against his bonds and ejaculated all over himself.

Fantastic!

Once again I couldn’t believe how easy it all was. I had expected whining, resistance, and a whole shit-load of pathetic male posturing. But this silly little slut-boy took to his transformation like a duck to water. I had him right where I wanted him then. And I lost no time letting him know it.

“Look over there at my computer table, slut-boy. Do you see it? Please notice that my webcam is on, and that it’s trained directly on you. I just got a recording of you made up like the lowliest slut, admitting that you are a wretched little slut, and then coming all over yourself as you make the admission. According to the time-honored tradition of blackmail, that means I own you now, doesn’t it? If you don’t want the whole school, and indeed the whole world to see that recording, and know what a disgusting sissy slut you are, then you had better obey me in absolutely everything from now on!”

Oh, his dismayed, appalled goggle was priceless!

“Are…are you serious?”

“You bet your slutty, sissy ass I am, Erica. You have just become my eternal slave. I now own you body and soul forever. And you have just begun your permanent transformation into a disgusting she-male. So admit it again! Say, ‘Yes, Mistress Tara, I am forevermore your personal property, a slutty little she-male sissy slave.’ Say it right now, or I’m going to go over there and email that recording to everyone we know, and then post it on the internet, for the entire world to see! And of course, it’s all password protected, and already uploaded to a secure server. Not even killing me and destroying my computer could prevent its eventual dissemination. I have planned for every contingency!”

Erica continued to goggle disbelievingly at me. But when I merely stared sternly down at her she at last swallowed hard, dropped her eyes and quietly husked out her acceptance.

“Yes, Mistress Tara. I am forevermore your personal property, a slutty little she-male sissy slave.”

“Louder, slut-boy!” I immediately shrieked. “Look straight at the camera and say it loud and proud for the record!”

Tears of shame were streaming from her eyes, but Erica clearly knew she had no choice. With one diabolical stroke I’d claimed ownership of her forever. She even willingly elaborated on her oath of service.

“Yes, Mistress Tara! I am forevermore your personal property, a slutty little she-male sissy slave. I will do absolutely anything you say for all eternity.”

“Good, slut-boy,” I mocked. “Now, I’m going to get you appropriately cross-dressed and into bed. Then as promised I’m going to fuck your slutty little brains out. So don’t you dare try to resist me in the slightest! Not only will I beat the shit out of you, I’ll immediately out you to the entire world!”

Of course, what Erica didn’t know was that all my cheerleader friends, and everyone else at the party, was still watching this entire scene live. Everyone in school would know about Erica’s transformation soon enough regardless. But even by tomorrow it would be way too late. Soon I’d have an even more implacable hold on her.

In any case, Erica remained docile and compliant when I released her from the chair and dressed her in my cheerleader’s uniform. She offered no resistance at all as I bound her wrists together, led her over to the bed and ordered her to lie flat on her back. I stretched her arms above her head, and tied them securely to the headboard. Then I adjusted the webcam to keep her in the picture.

“Be good now, Erica. I have to go change. But I’ll be back soon to make this all transformation worth it for you by fucking you absolutely senseless!”

Haughtily I turned my back on her then, marched into our shared wardrobe and slammed the door. She’d learn what (and who) was coming soon enough!