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Don't Bet on It!

by Sissy Demi

 

"Hah! Hah!" she laughed, placing her hands on her rather voluptuous hips, "You lost the bet and now you've got to do whaaaaateeeeever I want!" Sharon was positively exuberant at this prospect. In fact, she fairly glowed. I knew I was in trouble then. But still I had to try and get out of whatever my crazy lover had cooked up for me.

"But Sharon, sweetikins, darling lover o'mine," I started to say.

"Uh uh, buster," she said wagging a finger at me, "You made a bet and lost. You said if you won I had to be your 'stunningly sultry servile sex slave' and if I won that I could choose a task for you. And you lost!" Sharon fairly squealed that last part. She was just enjoying this too, too much for my liking. I could see the almost evil intent burning in her bright green eyes.

Well, I thought to myself as I eyed her tall yet shapely figure, if it involves sex with this gorgeous creature, it couldn’t be all bad. The sex with Sharon was always great. It was as if she were my perfect compatible playmate. Being just an inch or so shorter than me made kissing her fine featured face while doing the vertical bed-dance almost too easy. And she wasn't one of those Barbie girls either, with their ten-inch waists and over proportioned tits and hips. No, Sharon was a good-sized woman, and I don't mean fat or overweight, either. Muscular, without being bulky, was more like it. Like I said, my perfect sex partner and a hell of a conversationalist to boot.

She grabbed my wrist and pulled me up from the bed, breaking my reverie and making me realize my situation again. Gently, I pulled her close and nuzzled her ear under the soft waves of red hair. My hands caressed her back, working their way down to her ass for a firm squeeze or two. She started to relax and moan, and I thought I had her.

"No way! Thought you had me there, didn't you?" Sharon snapped as she roughly pushed me back onto the bed. "You're not getting out of this one that easily." I started to stammer a reply, but the look in her eyes told me to keep quiet. I did.

She stood looking at me strangely for a minute. Almost as if she were studying me, sizing me up. Then her eyes lit up and a slow, wicked grin spread across her face. A low chuckle emanated from deep in her throat, giving me the willies. A chill spread down my spine causing me to shiver involuntarily.

"Stand up," she commanded me. I obeyed with haste. "Start taking your clothes off, loser. And turn around and face the wall as you do. Oh, yeah, keep your eyes shut, too. That is if you know what's good for you!"

I pulled off my shoes and turned around, debating whether to peek at what Sharon was doing or not. I decided to continue removing my clothes. No sense in tempting fate. Or Sharon.

As I was taking off my shirt, I heard her open the closet door. The screech of metal on metal assaulted my ears, wire hangers scraping across a steel rod. She finished with whatever she was doing in the closet and started to rummage in the dresser drawers. I was getting nervous, but I finished undressing anyway. I stood quietly waiting a few moments as she continued looking in a drawer, muttering to herself.

"Finished?" she inquired sweetly. I said yes and started to face her.

A sharp smack on my bare ass cheek stopped me mid-turn. "I did not tell you to turn around. And keep your eyes closed, asshole." Another smack, harder this time, accompanied her remark. Not wanting to be swatted again, I did as Sharon told me.

"Very good!'" she praised, "Now turn around, keeping your eyes shut."

Meekly, I turned. "Ok, put your right arm up and make a loose fist." As I did, I felt a few hangers placed on my hand, the slight weight of them pulling it down a little.

"Ok, open your eyes," I was told.

I looked at what she had hung on my hand.

It was a white poet's blouse with a ruffled collar and long sleeves ending in a double ruffle at the wrist, along with a denim, button front crinkle skirt. A lacy, thong bodysuit hung from the third hanger. It was white, too.

My jaw dropped to the floor at the same time my heart leapt to my throat. She stood in front of me, arms crossed and legs wide, an expectant look on her face.

"Put them on."

I hesitated and tried to say anything that would change her mind.

"I mean it," she said. "Here I'll help you."

Sharon took the things from my hand and laid them on the bed save the bodysuit. She adjusted the shoulder straps, making them larger and motioned for me to step into it. I shook my head nervously. Her green eyes darkened and her jaw tightened. I swallowed and stepped into the offending attire, Sharon pulling it up around me as I did. Slowly she slid the straps over my shoulders and tightened them a little. I had seen this very same under garment on Sharon many times and always thought it was a very sexy thing for her to wear. I even told her so on numerous occasions, that usually culminating in a good lay. But now I didn't know what to think, as Sharon's gaze traveled down my femininely clad body to my crotch.

She reached down and carefully slid my cock and balls from the confines of the lacy garment so that they were hanging loose. Then she pulled the lower half of the bodysuit up a hitch. This caused the thong to ride up my ass crack and I told her this. A smug look appeared on her face and her eyebrows arched. She thought for a second as she appraised me again.

"Hmmmm," my tormentor murmured as she placed some padding in the bra cups and adjusted them. "That gives me an idea. But later, now I want you to get used to this." She lightly tapped my cockhead from side to side as she said this, watching as my member came to a semi-erection. I took a moment to glance in the wall mirror and noticed the bodysuit had nipped an inch or so from my waist and stomach. That, along with the padded bra, gave the illusion of at least B or C breasts. Sharon noticed me looking and answered my unasked question.

"It's a body briefer with a padded bra, dear," she told me, " To make a girls figure more girlish."

"B-but I...I'm not a girl," I stuttered out.

"Remember how you said I was going to be your sex-kitten, and do whatever, wear whatever you desired? Cater to your every whim?" Sharon asked. I gulped and nodded, seeing where this line of questioning was leading. "Well," She continued, "I thought I would let you feel how it would be. You are now my slave...all this holiday weekend. Wait. Your vacation starts Monday, too. I guess you'll be my little slave girl for the whole two weeks."

I nearly swooned at the idea. How did I get myself into this? All I wanted to do was have Sharon sexually satisfy me all weekend as my sex-slave. I was going to treat her good. Take her out dancing, to dinner, even shopping with my commission bonus. Just that during these times she was supposed to act like I was a god or something. I told Sharon this, figuring she'd drop this crazy notion and let me out of the lace encasement.

"Why, sweetheart, I didn't know all you had planned IF you had won," she stated, "I guess we could still do those things. With you in my place, of course."

I nearly fainted dead on the spot.

"Let's think of a name for you while we finish getting you dressed, shall we?" Sharon had me put my arms up as she pulled the cotton blouse over my head and primped the ruffles to fluff out. Then I put the denim skirt on. She fussed with a few details then stood back to look at me.

"You look like a proper girl, honey," she said, "All except that little tent in your nice skirt. But I know how to take care of that."

Roughly, I was pushed onto the bed. Sharon straddled me and ran her hands under my skirt reaching for my cock.

Visions of the Bobbits ran through my head.

Warm hands found my cock and balls. Softly they fondled them, increasing my erection to where I thought it would explode. Suddenly, she stopped. Slowly she slipped my cock through the hole between buttons on the skirt and wrapped her lips around the shaft.

"I think I'll call you Brianna," she whispered as she started to suck me off.

I felt strange looking over two breasts covered in ruffles, at a beautiful woman lapping my cock that was jutting out of a flowing skirt. A warm, tingling sensation spread from my crotch into my abdomen. It felt great and I was actually turned on by this. Sharon's red hair cascaded over her shoulders as she bobbed up and down on my swollen member, her hands creeping up my stomach to cup my makeshift tits. Her hands squeezed and massaged them, causing the pads to rub against my nipples. They sprung out and made the sensation even more enjoyable.

Without warning, my cock jerked wildly and I spasmed with an ejaculation stronger than I'd had in a while. Sharon sucked my rock hard bone dry then pulled herself on top of me. With surprising force, she jammed her lips to mine. I opened my mouth and forced my tongue into hers. Abruptly, my mouth was filled with a hot, salty gunk and Sharon's tongue swirled it around in my mouth.

"Swallow it, Brianna," she ordered. I did and almost gagged on it, but her gentle lips kept me from spitting it up. Her hand went my softening member as the other stroked my face.

"Bri, this is just the beginning of a great two weeks!"

--fin?--

 

 

Postscript: I wrote this short story quite some time ago. I believe it was back in early '93, about the time my ex-wife and I were contemplating divorce. The story deviates greatly from my usual teen-aged, "G" rated stories.

It reads well enough as a stand-alone story, leaving the continued adventures of the formerly nameless hero up to the imagination. I originally decided to leave the hero nameless, as it was just a fantasy involving myself that was being put to words. But the overall effect of having no nameable character as the main protagonist nicely allows the readers to easily place themselves into the scene.

As for the femme name Sharon gives him, if you really would like to see it as a different name, just do a find and replace using the name you like the best! (Oh come on now! You can't sit there and tell me you have never done that before. ::wink::). The same goes for Sharon, too. Change her name to another if it pleases you. It's easy to do and customizes a story for that added pleasure! WooHoo!

I also left the nature of the bet up to the reader's imagination. It's just a plot device to get the hero into feminine finery anyhow. I feel no need to have a drawn out explanation of what it was.

My current (and hopefully last! :) girlfriend and I have made numerous bets on anything and everything. They range from how many messages on the answering machine to what time the kids will walk in the door to the price of ground beef at the supermarket! And some of the consequences of losing were pretty steep for such inconsequential bets, I can tell you!

You'll also notice that I like to interject quite a bit of humor into the stories I write. Call it an inbred trait. There is little I do that is without humor, sometimes even too much of it... :/

Well, I seem to be rambling, and I thank all of you who have taken the time to actually read the 'Postscript' for "Don't Bet on It!" Happy reading and remember that this story is intended to perused with one hand only! ;>

Sissy Demi

 

 


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1993 by Sissy Demi. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.