Dont Bet on It

Published on Dec 26, 1997

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This is a transvestite story. It contains sexual scenes and forced crossdressing. If you are offended by this type of material... go stick your head back into your narrowminded life and leave us freethinkers alone. If you are under the legal age for adult material in your state or country... until there are enough flaming wax stubs on your cake, go away!

This is something I wrote a loooooooong time ago and had thought was lost on a encrypted disk somewhere. Imagine my surprise when I stumbled across it while cleaning directories. I even had the password to it remembered! Enjoy....

Don't Bet on It!

"Hah!Hah!" she laughed, placing her hands on her rather voluptous 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 ` stuningly 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 can'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 thier ten inch waists and over proportioned tits and hips. No, Sharon was a good sized woman, and I don't maen fat or overweight, either. Muscular, wiyhout 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 uder the soft waves of red hair. My hands caressed her back, working thier 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 pused 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 strangly 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 eminated 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 wether 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 anyways. 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 asscheek 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, buttonfront 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 layed 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 nevously. 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 ot think, as Sharon's gaze travelled down my femininly 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 murmmered 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 commision 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 cotten 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. Sharons 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 suprising 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 Sharons 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!"

tbc???

Continue the story if you'd like, I doubt I will...

As I do noty have direct Internet access, please make all replies and comments to ATTN: Sissy Demi on the alt.sex.stories.tg newsgroup. Thank You!

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