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10 Button Dress

A lost bet changes everything
This is intended for adults 21 and over only. If you are offended by

graphic descriptions of a sexual nature, please, don't read this or

download it.

If this is illegal where you are reading this, stop now.

Copyright August 1998 Don Darkdom all rights reserved. Permission to read and download for non-commercial purposes is granted.

10 Button Dress

by Don Darkdom

The first time I played the game, I was wearing a blue silk, ten-button dress. My college roommate, Sonia was trying to convince me to stay home and study instead of going out to dinner with Jesse, my new boyfriend. What can I say, Art History was a bore. I wasn’t failing, but well you know, I wasn’t working up to my potential.

I had gone into Sonia’s room to ask her if I could borrow a belt that matched my dress. She was curled up on her bed in a long T-shirt, studying. (Sonia is smart, beautiful, and had begun to sound too much like my mother.) She challenged me to a quick quiz. If I won, I got the belt for keeps, if I lost I had to stay home and study. Every incorrect answer I had to unbutton one button on my dress, get ten correct with no open buttons on my dress I win. A correct answer and I could redo one button. Open all my buttons, I lose. Simple rules. So okay it wasn’t the greatest idea, but Jesse wasn't going to arrive for an hour and I wanted the belt.

I got the first two questions right, and then over the next half hour missed nine. Standing with my dress almost completely open, I was struck suddenly by the sexiness of the moment. it was a little disconcerting, I had never been attracted to women before. But, Sonia sitting on her bed, watching me, unbuttoning my dress. Wow. Under my bra, my nipples began to tighten and I could feel my panties getting damp.

Sonia jumped up from the bed. “You know you’re going to lose, Mai”, she said.

“A minor setback, nothing more”, I replied more confidently than I felt.

“Want to raise the stakes?”, asked Sonia.

“How?", I asked.

“After you lose the last button,"

“I won’t”

“Yeah, yeah. One bonus question if you get it right I follow your orders all weekend, get it wrong and you follow mine. Simple, right. So….. deal?"

If I’d been thinking clearly I probably would have stopped things right there.

“Okay. Let’s get finished before Jessie gets here”, I answered.

I missed the next two questions and found myself standing in front of Sonia with my dress completely open, my undies showing and about to be told what to do all weekend. What was I going to tell Jesse? My jumbled thoughts were finally pierced by the realizations that this was actually exciting and that Sonia was talking to me.

“First of all, I want you to keep your date with Jesse. I need some time to prepare. But here are the rules for the date: no sex, you can tell him about the bet you lost if you want, and bring him home with you by midnight”, Sonia ordered.

“Yes, Mom”, I sassed.

“No more back talk. You lost fair and square”, Sonia said evenly. “Oh, and lose the underwear.”


“You heard me! Panties and bra, off now!”

I was just able to hold her glare while my trembling hands removed first my panties, then my bra. We’d seen each other in various stages of undress before, but this was somehow different.

Now standing in front of her, naked except for my unbuttoned dress, I shivered in anxiety and excitement. I couldn’t hold her gaze any longer and looked down only to see my underwear staring back at me, confirming my humiliation.

“Pick them up and give them to me”, Sonia demanded.

I did as she told me and she smiled wickedly.

“Your panties are wet, Mai” she taunted.

I think I blushed from head to toe.

Sonia reached out and lifted my chin. She patted my hair and stroked my cheek.

“Don’t worry, Mai. Not only will you get a good grade on your test, but you’ll have great weekend and so will I”, she laughed.

She stroked a line from one shoulder to the other, several times, each time coming closer to my breasts. It was almost a relief when her finger finally brushed across my nipples. She noticed them tighten of course and smiled wickedly, again. She walked behind me. I could feel her body lightly pressed against my back.

“Don’t move, until I say you can”, she growled in my ear.

Even that sent a twinge of excitement through me. I could feel her nipples hardening against my back and pressed back against her.

“I said don’t move, Mai.”

She began again to stroke me, with both hands. First my arms then back to my breasts. This time she lightly scratched them with her nails. I could feel the wetness building inside me. The light scratching now roamed lower. Just before she reached my bush, she stopped.

“Is this exciting you, Mai are you very wet”, she asked?

“Not very”, I blushed.

“Liar!” she hissed.

She spun me around quickly and pressed her outstretched finger between my nether lips. I could feel the liquid drip onto to her finger. She raised her wet finger to my face then to her own, and I could smell my own arousal undeniably.

“Spread your legs wider, Mai.”

I did as Sonia bid and her finger returned to my pussy. She began to saw back and forth through my lips. Each stroke making me wetter, more excited and more ashamed. Sonia’s finger was driving me closer to a spectacular orgasm, yet she hadn’t touched my clit, yet. I began to lean into her finger to get her to touch my clit.

“I said don’t move, Mai.”

“Please”, I whimpered.

She pulled her finger away. I moaned in frustration.

“Mai, I want you to close your eyes and keep them shut.

I did and her finger returned briefly to my pussy. She traced a line through my lips, graced my clit, and I almost came. Then her finger continued slowly upward, finally coming to rest under my nose.

“Suck my finger like you do Jessie’s cock.”

I moaned again in frustration, humiliation and excitement. As I sucked on her finger, her other hand began to stroke across my clit. She stopped just short of my climax and pulled both fingers out. I moaned, again.

“Bend over and grab your ankles.”

“What are you going to do, Sonia?”

“I’m going to finger fuck your ass, then spank you till you cum, silly. Now bend over.”

When I was in position she jabbed her finger into my ass. She stroked in and out for a few minutes and soon had me on the verge again. I felt her finger slide completely out of my ass and then two very hard swats stung each cheek.

That was when the knock on the door announcing Jesse’s arrival sounded.

“Don’t move, Mai,” Sonia hissed. “Maybe I should just show Jesse in so he can see how you really want to be treated.”

All I could do was whimper.

She went to the door and I could just hear her tell Jesse I was finishing dressing and would be right out.

She returned and pulled me standing. She took my head in her hands and reminded me of the rules for my date with Jesse. I shivered in anticipation of what she had planned for the rest of the weekend. Then she kissed me hard on the lips and told me to button my dress. Which I did.

“One last thing before you go, Mai.”

She was sitting on her bed. Legs spread brazenly apart and rubbing her own pussy. She didn’t need to tell me what she wanted and I fell to my knees and began to lap at her. Her hands pressed me tightly against her and I felt her spasm against me quickly. I rose on unsteady legs to meet Jesse with Sonia’s taste still on my lips.


Still shaking with excitement I stepped out of the apartment. Jesse hugged me, put his arm around my shoulders and we headed out to his car. As he opened the door for me, he bent over and kissed me.

“You smell delicious, Mai. Is that a new perfume”, Jesse asked? Without waiting for an answer Jesse headed for the drivers side. Trying to collect myself I leaned across to unlock his door. As Jesse got in, started up, and pulled out of the spot, I noticed how high my dress had ridden on my thighs. Apparently, so had Jesse. He reached over and began to stroke my thigh lightly. He was talking softly, casually, as he continued to caress my thigh. I wasn’t really listening to his words; I was caught up in the sensation of his fingers brushing closer to my super heated pussy. He hadn’t yet realized that I wasn’t wearing panties, but it was only a matter of time. When his exploring fingers found my nakedness, we both gasped. I felt the wetness, again begin to build and realized that I had to do something or ruin my dress before we even reached the restaurant. I quickly lifted the dress so that my bare ass was on the cold seat. I shivered and spread my legs further for Jesse’s fingers.

“What’s gotten into you tonight, Mai.”

With his fingers driving me closer to an orgasm, I began to shake and ride his fingers. Just as I was about to cum he pulled his hand away. I moaned in frustration. I was about to take matters into my own hands when we pulled up to the restaurant.

“Jesse, how did you get us into Flash In The Pan? I thought they were booked till forever.

Flash In The Pan was the new chic spot, with entertainment rumored to be top notch no names with a bizarre twist, entertainers and customers were encouraged to show skin. The food was rated five star. As we were being seated I realized that I was dressed perfectly for this. I quickly unbuttoned the top two and bottom three buttons on my dress. I was immediately rewarded with an appreciative moan from Jesse and a laughing leer from the maitre-de.

The tables surrounded a circular stage. Our table was on the second of three levels. I realized that those on level one could look up and see Jesse and I, likewise we could look up and see the third tier. I spotted a man sliding his hand up a woman’s skirt, her hand appeared to be buried in his trousers. I thought about all that had occurred this day and tried to think how I would be able to not have sex with Jesse in this atmosphere.

I sat with my dress adjusted so that my bare butt was on the chair, with my legs slightly parted. Stimulated by all of the other diners, the entertainers, and Jesse’s roving hand, I was barely aware of dinner until dessert was served.

Tall men and women dressed in desert costumes served dessert. Thin, almost transparent linen dashiki’s open at the front, and billowing at the bottom. Men and women wore the same garment. Jesse was being served by a dark, almond eyed beauty, who was feeding him strawberries and cream, mouth to mouth. Jesse was still fingering my pussy. With his other hand he was reaching up and pinching the serving girl’s breasts. We were both moaning with excitement. My attention was suddenly pulled away from Jesse by the sight of the serving man lifting his own dashiki, revealing an enormous erection covered by the strawberries and cream. I practically dove on to his cock.

Sucking, licking biting, I grabbed his ass and pulled him closer to my face. When I had him completely engulfed, I began to suck him harder and was soon rewarded with a dose of his cream. He flipped me onto my back and using the cream and my juices, pressed his still hard cock deeply up my ass. I screamed once but then he began to stroke in and out and my excitement was raised to yet another fever pitch. Jesse’s hands were still busy with the other girl so I shuffled over and dove onto his cock with my mouth. As I stroked him with one hand and sucked him harder and harder with my mouth, I felt us both reaching another immense climax.

As we began to come back to reality, we shuddered together as our companions helped us to look more presentable. We could also hear applause from the rest of the room. Embarrassed, but satiated we headed for the exit.

In the back of my mind I was still worried about what Sonia had in store for when we returned.


On the drive back, I told Jesse about my bet with Sonia. He nodded and laughed when I asked him not to tell Sonia about our quickie in the restaurant. All too soon, we were standing in front of the apartment. I opened the door with some anxiety and not a little excitement. Candles dimly lit the living room, dance music played softly in the background and I could see Sonia stretched out on the couch.

She was dressed, or nearly so, in a red rubber mini-skirt and a white lace bustier. Her nipples poked out impudently. She looked hotter than I’d ever seen her. “Did you tell him?” Sonia asked. I nodded. Jesse snickered. I poked him with my elbow. A tactical error I realized as Jesse proceeded to tell Sonia the details of our adventure at Flash In The Pan.

“I knew you would break the rules, in fact I was counting on it”, Sonia laughed. “Are you ready for your punishment, Mai?”

Not really, I thought, but my body betrayed me again as I felt my head nod affirmatively.

“Jesse, would you rather spank her bottom or have your cock sucked?” Sonia asked?

Jesse paused to consider and decided to spank me. Sonia directed Jesse to sit on the couch; me across his lap with my face buried in Sonia’s delightfully soaked pussy. As Jesse spanked harder and harder, I licked and sucked Sonia harder and deeper. I could feel Jesse’s hard on pressing against me as he continued to pound my ass. Sonia came explosively and locked her legs around my face. Jesse suddenly stopped spanking and shoved a finger into my already sore asshole. Then two, three and soon it felt like he had his whole fist up my ass and I was coming despite the pain, or maybe because of it. Once a semblance of calm returned, Sonia directed Jesse to tie me to a chair with some rope she had handy. He followed her instructions and I was soon immobile. Sonia explained that my last punishment for the day would be to watch as Jesse used his cock on her. Tomorrow we would begin studying, and other punishments and delights awaited me. But that’s a tale for another time.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © Copyright 2013 Don Darkdom

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